dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-a9eb8bf838c248b3ad5908714b48274f | CN1CCNCC1.COc1cc(Cl)ccc1I>>COc1cc(Cl)ccc1N1CCN(C)CC1 | COC1=C(C=CC(=C1)Cl)I.CN1CCNCC1>>CN1CCN(CC1)C2=C(C=C(C=C2)Cl)OC | [NH:10]1[CH2:11][CH2:12][N:13]([CH3:14])[CH2:15][CH2:16]1.I[c:9]1[c:3]([O:2][CH3:1])[cH:4][c:5]([Cl:6])[cH:7][cH:8]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([Cl:6])[cH:7][cH:8][c:9]1[N:10]1[CH2:11][CH2:12][N:13]([CH3:14])[CH2:15][CH2:16]1 | CN1CCNCC1.COc1cc(Cl)ccc1I | COc1cc(Cl)ccc1N1CCN(C)CC1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 75de53007ec0cb91435746fdefbf3b121f745fc71ddebd19c6e45a5212b3f56a | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#8:5]):[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[#8:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1):[c:2]:[c:3] | 0 | [{"value": 0.0, "product": "CN1CCN(CC1)C2=C(C=C(C=C2)Cl)OC", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | 1-methylpiperazine (0.021 mL, 0.19 mmol) was added to 4-chloro-1-iodo-2-methoxybenzene (50 mg, 0.19 mmol) and sodium 2-methylpropan-2-olate (35.8 mg, 0.37 mmol) in toluene (0.650 mL) and the solution degassed. rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (11.60 mg, 0.02 mmol) and Palladium II acetate (4.18 mg, 0.02 ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ccccc1 | c1ccccc1.C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1 | HI | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 80 | null | CN1CCNCC1.COc1cc(Cl)ccc1I>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>COc1cc(Cl)ccc1N1CCN(C)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-4ad2f7e2a41645bd9dba54aaef4fa989 | Cc1csc(N)n1.O=C1COCCN1c1cccc(Br)n1>>Cc1csc(Nc2cccc(N3CCOCC3=O)n2)n1 | C1COCC(=O)N1C2=NC(=CC=C2)Br.CC1=CSC(=N1)N>>CC1=CSC(=N1)NC2=NC(=CC=C2)N3CCOCC3=O | [CH3:1][c:2]1[cH:3][s:4][c:5]([NH2:6])[n:20]1.Br[c:7]1[cH:8][cH:9][cH:10][c:11]([N:12]2[CH2:13][CH2:14][O:15][CH2:16][C:17]2=[O:18])[n:19]1>>[CH3:1][c:2]1[cH:3][s:4][c:5]([NH:6][c:7]2[cH:8][cH:9][cH:10][c:11]([N:12]3[CH2:13][CH2:14][O:15][CH2:16][C:17]3=[O:18])[n:19]2)[n:20]1 | Cc1csc(N)n1.O=C1COCCN1c1cccc(Br)n1 | Cc1csc(Nc2cccc(N3CCOCC3=O)n2)n1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C1COCCN1c1cccc(Nc2nccs2)n1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7]1:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:1>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7]1:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:1):[c:4]:[c:5] | 80.02 | [{"value": 80.02, "product": "CC1=CSC(=N1)NC2=NC(=CC=C2)N3CCOCC3=O", "details": "", "is_desired": true}] | 115 | CELSIUS | null | null | **_September 24 2015_** 4-methylthiazol-2-amine (200 mg, 1.75 mmol), 4-(6-bromopyridin-2-yl)morpholin-3-one (450 mg, 1.75 mmol), 4-(6-bromopyridin-2-yl)morpholin-3-one (450 mg, 1.75 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (81 mg, 0.14 mmol) and cesium carbonate (685 mg, 2.10 mmol) in toluene (... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1cscn1.c1ccncc1.C1COCC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].CC1=CC=CC=C1 | 115 | null | Cc1csc(N)n1.O=C1COCCN1c1cccc(Br)n1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].CC1=CC=CC=C1>Cc1csc(Nc2cccc(N3CCOCC3=O)n2)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-3571e003ae98463b83eba103dff01204 | Cc1csc(N)n1.O=C1COCCN1c1cccc(Br)n1>>Cc1csc(Nc2cccc(N3CCOCC3=O)n2)n1 | C1COCC(=O)N1C2=NC(=CC=C2)Br.CC1=CSC(=N1)N>>CC1=CSC(=N1)NC2=NC(=CC=C2)N3CCOCC3=O | [CH3:1][c:2]1[cH:3][s:4][c:5]([NH2:6])[n:20]1.Br[c:7]1[cH:8][cH:9][cH:10][c:11]([N:12]2[CH2:13][CH2:14][O:15][CH2:16][C:17]2=[O:18])[n:19]1>>[CH3:1][c:2]1[cH:3][s:4][c:5]([NH:6][c:7]2[cH:8][cH:9][cH:10][c:11]([N:12]3[CH2:13][CH2:14][O:15][CH2:16][C:17]3=[O:18])[n:19]2)[n:20]1 | Cc1csc(N)n1.O=C1COCCN1c1cccc(Br)n1 | Cc1csc(Nc2cccc(N3CCOCC3=O)n2)n1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C1COCCN1c1cccc(Nc2nccs2)n1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7]1:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:1>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7]1:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:1):[c:4]:[c:5] | 66.55 | [{"value": 66.55, "product": "CC1=CSC(=N1)NC2=NC(=CC=C2)N3CCOCC3=O", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | **_September 16 2015_** 4-methylthiazol-2-amine (65 mg, 0.57 mmol), 4-(6-bromopyridin-2-yl)morpholin-3-one (146 mg, 0.57 mmol), 4-(6-bromopyridin-2-yl)morpholin-3-one (146 mg, 0.57 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (26.4 mg, 0.05 mmol) and cesium carbonate (223 mg, 0.68 mmol) in toluene ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1cscn1.c1ccncc1.C1COCC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].CC1=CC=CC=C1 | 120 | null | Cc1csc(N)n1.O=C1COCCN1c1cccc(Br)n1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].CC1=CC=CC=C1>Cc1csc(Nc2cccc(N3CCOCC3=O)n2)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-5053ba4582cb4771951a27c38d53fae2 | CC(C)(C)OC(N)=O.Clc1cnnc(Cl)c1>>CC(C)(C)OC(=O)Nc1cc(Cl)cnn1 | C1=C(C=NN=C1Cl)Cl.CC(C)(C)OC(=O)N>>CC(C)(C)OC(=O)NC1=NN=CC(=C1)Cl | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH2:8].Cl[c:9]1[cH:10][c:11]([Cl:12])[cH:13][n:14][n:15]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][c:11]([Cl:12])[cH:13][n:14][n:15]1 | CC(C)(C)OC(N)=O.Clc1cnnc(Cl)c1 | CC(C)(C)OC(=O)Nc1cc(Cl)cnn1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling | 4c5d738209ae8bdb7c23dd098be92f866dd8f7be026520a4929f129212fe99c8 | 23f4e0d8af1d86d8b907685b9e69e28ed17e2c9c83b8194f1d8a52eb89f58564 | c1ccnnc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.[C;D1;H3:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[#8:11]-[C:12](-[NH2;D1;+0:13])=[O;D1;H0:14]>>[C;D1;H3:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[#8:11]-[C:12](=[O;D1;H0:14])-[NH;D2;+0:13]-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1 | 100 | [{"value": 100.0, "product": "CC(C)(C)OC(=O)NC1=NN=CC(=C1)Cl", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | **_April 15 2016_** 3,5-dichloropyridazine (1 g, 6.71 mmol), tert-butyl carbamate (3.93 g, 33.56 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane) (0.583 g, 1.01 mmol), PdOAc2 (0.452 g, 2.01 mmol) and CS2CO3 (4.37 g, 13.43 mmol) in 1,4-dioxane (20 mL) was degassed through recharged with nitrogen, and wa... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Carbamic ester | Carbamic ester | c1ccnnc1 | c1ccnnc1 | c1ccnnc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 80 | null | CC(C)(C)OC(N)=O.Clc1cnnc(Cl)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CC(C)(C)OC(=O)Nc1cc(Cl)cnn1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-5911a740f60145b0bc355f2a886b772f | Clc1ccccc1Br.NCCN>>NCCNc1ccccc1Cl | C1=CC=C(C(=C1)Cl)Br.C(CN)N>>C1=CC=C(C(=C1)NCCN)Cl | Br[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[Cl:11].[NH2:1][CH2:2][CH2:3][NH2:4]>>[NH2:1][CH2:2][CH2:3][NH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[Cl:11] | Clc1ccccc1Br.NCCN | NCCNc1ccccc1Cl | CC(C)(C)[O-].[Na+] | CC1=CC=C(C=C1)P(C2=CC=C(C=C2)C)C3=CC=C(C=C3)C.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6] | 0 | [{"value": 0.0, "product": "C1=CC=C(C(=C1)NCCN)Cl", "details": "", "is_desired": true}] | 140 | CELSIUS | null | null | Ref: R2239 To a mixture of 1-bromo-2-chlorobenzene (0.824 g, 4.30 mmol), tri-p- tolylphosphine (0.262 g, 0.86 mmol), sodium 2-methylpropan-2-olate (0.414 g, 4.30 mmol), diacetoxypalladium (0.097 g, 0.43 mmol) in toluene (4 mL) was added ethane-1,2-diamine (1.293 g, 21.52 mmol). The mixture was heated with microwave at... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | CC(C)(C)[O-].[Na+].CC1=CC=C(C=C1)P(C2=CC=C(C=C2)C)C3=CC=C(C=C3)C.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 140 | null | Clc1ccccc1Br.NCCN>CC(C)(C)[O-].[Na+].CC1=CC=C(C=C1)P(C2=CC=C(C=C2)C)C3=CC=C(C=C3)C.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>NCCNc1ccccc1Cl |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-a6f7db18dd5949e09df857ba4df0f8b1 | C1CNCCN1.FC1(F)Oc2ccc(Br)cc2O1>>FC1(F)Oc2ccc(N3CCNCC3)cc2O1 | C1=CC2=C(C=C1Br)OC(O2)(F)F.C1CNCCN1>>C1CN(CCN1)C2=CC3=C(C=C2)OC(O3)(F)F | [NH:9]1[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]1.Br[c:8]1[cH:7][cH:6][c:5]2[c:16]([cH:15]1)[O:17][C:2]([F:1])([F:3])[O:4]2>>[F:1][C:2]1([F:3])[O:4][c:5]2[cH:6][cH:7][c:8]([N:9]3[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]3)[cH:15][c:16]2[O:17]1 | C1CNCCN1.FC1(F)Oc2ccc(Br)cc2O1 | FC1(F)Oc2ccc(N3CCNCC3)cc2O1 | CC(C)(C)[O-].[K+] | CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | db4f678b3752acc239e8fb20778308c8315d131f38efc26609b576f6811ef199 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cc2c(cc1N1CCNCC1)OCO2 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[#8:4]):[c:5]:[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[#8:4]-[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1):[c:5]:[c:6] | 50.68 | [{"value": 50.68, "product": "C1CN(CCN1)C2=CC3=C(C=C2)OC(O3)(F)F", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | 13-May-09 10:32:07 +0100 5-bromo-2,2-difluorobenzo[d][1,3]dioxole (0.500 g, 2.11 mmol), piperazine (0.182 g, 2.11 mmol) and BIS(TRI-T-BUTYLPHOSPHINE)PALLADIUM(0) (0.054 g, 0.11 mmol) and potassium 2-methylpropan-2-olate (0.349 g, 2.95 mmol) were suspended in dioxane (10vol) (10 mL) and heated to 90°C for 1 hour. LC-MS... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2.C1C[NH]CCN1 | c1ccc2c(c1)OCO2.C1C[NH]CCN1 | HBr | CC(C)(C)[O-].[K+].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.[Pd].C1COCCO1 | 90 | null | C1CNCCN1.FC1(F)Oc2ccc(Br)cc2O1>CC(C)(C)[O-].[K+].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.[Pd].C1COCCO1>FC1(F)Oc2ccc(N3CCNCC3)cc2O1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-055a4c71f284445f89aad15e03c56285 | C/C=C(/c1ccc(Cl)cc1)N(C(=O)NC)c1ccc(OC)cc1.COc1cccc(Br)n1>>C/C=C(/c1ccc(Cl)cc1)N(C(=O)N(C)c1cccc(OC)n1)c1ccc(OC)cc1 | COC1=NC(=CC=C1)Br.C/C=C(/C1=CC=C(C=C1)Cl)\N(C2=CC=C(C=C2)OC)C(=O)NC>>C/C=C(/C1=CC=C(C=C1)Cl)\N(C2=CC=C(C=C2)OC)C(=O)N(C)C3=NC(=CC=C3)OC | [CH3:1]/[CH:2]=[C:3](/[c:4]1[cH:5][cH:6][c:7]([Cl:8])[cH:9][cH:10]1)[N:11]([C:12](=[O:13])[NH:14][CH3:15])[c:24]1[cH:25][cH:26][c:27]([O:28][CH3:29])[cH:30][cH:31]1.Br[c:16]1[cH:17][cH:18][cH:19][c:20]([O:21][CH3:22])[n:23]1>>[CH3:1]/[CH:2]=[C:3](/[c:4]1[cH:5][cH:6][c:7]([Cl:8])[cH:9][cH:10]1)[N:11]([C:12](=[O:13])[N:1... | C/C=C(/c1ccc(Cl)cc1)N(C(=O)NC)c1ccc(OC)cc1.COc1cccc(Br)n1 | C/C=C(/c1ccc(Cl)cc1)N(C(=O)N(C)c1cccc(OC)n1)c1ccc(OC)cc1 | CC(C)(C)[O-].[Na+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Goldberg coupling | c3e9b5e88e70ea085ab3c4bfcb036b7f23a5295a2a4a0ed37fb9d51f344d671b | 4c2887f4c8bf37383c1643fa8c0d6572d6d560713e2566c5529210af209aa988 | [CH]=C(c1ccccc1)N(C(=O)Nc1ccccn1)c1ccccc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[NH;D2;+0:7]-[C:8](=[O;D1;H0:9])-[#7:10](-[c:11])/[C:12](-[c:13])=[C:14]\[C;D1;H3:15]>>[C;D1;H3:6]-[N;H0;D3;+0:7](-[C:8](=[O;D1;H0:9])-[#7:10](-[c:11])/[C:12](-[c:13])=[C:14]\[C;D1;H3:15])-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 71.95 | [{"value": 71.95, "product": "C/C=C(/C1=CC=C(C=C1)Cl)\\N(C2=CC=C(C=C2)OC)C(=O)N(C)C3=NC(=CC=C3)OC", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | (Z)-1-(1-(4-chlorophenyl)prop-1-enyl)-1-(4-methoxyphenyl)-3-methylurea (0.400 g, 1.21 mmol),2-bromo-6-methoxypyridine (0.292 ml, 2.42 mmol),SODIUM TERT- BUTOXIDE (0.349 g, 3.63 mmol),XANTPHOS (0.070 g, 0.12 mmol) and Pd2(dba)3 (0.055 g, 0.06 mmol) were dissolved intoluene (11.80 ml) and sparged under nitrogen for 1 hou... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Urea | Urea | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1ccccc1 | HBr | CC(C)(C)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 110 | null | C/C=C(/c1ccc(Cl)cc1)N(C(=O)NC)c1ccc(OC)cc1.COc1cccc(Br)n1>CC(C)(C)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>C/C=C(/c1ccc(Cl... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-47db17fde7b54b3497b21dd387d6839b | CC(N)c1cc(C(=O)N(C)C)cc2c(=O)cc(N3CCOCC3)oc12.N#Cc1cc(F)cc(Br)c1>>CC(Nc1cc(F)cc(C#N)c1)c1cc(C(=O)N(C)C)cc2c(=O)cc(N3CCOCC3)oc12 | C1=C(C=C(C=C1F)Br)C#N.CC(C1=CC(=CC2=C1OC(=CC2=O)N3CCOCC3)C(=O)N(C)C)N>>CC(C1=CC(=CC2=C1OC(=CC2=O)N3CCOCC3)C(=O)N(C)C)NC4=CC(=CC(=C4)C#N)F | [CH3:1][CH:2]([NH2:3])[c:13]1[cH:14][c:15]([C:16](=[O:17])[N:18]([CH3:19])[CH3:20])[cH:21][c:22]2[c:23](=[O:24])[cH:25][c:26]([N:27]3[CH2:28][CH2:29][O:30][CH2:31][CH2:32]3)[o:33][c:34]12.Br[c:4]1[cH:5][c:6]([F:7])[cH:8][c:9]([C:10]#[N:11])[cH:12]1>>[CH3:1][CH:2]([NH:3][c:4]1[cH:5][c:6]([F:7])[cH:8][c:9]([C:10]#[N:11])... | CC(N)c1cc(C(=O)N(C)C)cc2c(=O)cc(N3CCOCC3)oc12.N#Cc1cc(F)cc(Br)c1 | CC(Nc1cc(F)cc(C#N)c1)c1cc(C(=O)N(C)C)cc2c(=O)cc(N3CCOCC3)oc12 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1cc(N2CCOCC2)oc2c(CNc3ccccc3)cccc12 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8;a:6]:[c:7]:[c:8]-[C:9](-[C;D1;H3:10])-[NH2;D1;+0:11]>>[#8;a:6]:[c:7]:[c:8]-[C:9](-[C;D1;H3:10])-[NH;D2;+0:11]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 81.8 | [{"value": 81.8, "product": "CC(C1=CC(=CC2=C1OC(=CC2=O)N3CCOCC3)C(=O)N(C)C)NC4=CC(=CC(=C4)C#N)F", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | To a mixture of 8-(1-aminoethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide (300 mg, 0.87 mmol), cesium carbonate (1104 mg, 3.39 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (126 mg, 0.22 mmol) and 3-bromo-5-fluorobenzonitrile (382 mg, 1.91 mmol) in degassed 1,4-dioxane (2ml), was add... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2occcc2c1.C1COCC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 90 | null | CC(N)c1cc(C(=O)N(C)C)cc2c(=O)cc(N3CCOCC3)oc12.N#Cc1cc(F)cc(Br)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>CC(... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-87f8e3ca7c9b4c4884d79136750f7a54 | Clc1ccnc(Cl)c1.Nc1ncccn1>>Clc1ccnc(Nc2ncccn2)c1 | C1=CN=C(C=C1Cl)Cl.C1=CN=C(N=C1)N>>C1=CN=C(N=C1)NC2=NC=CC(=C2)Cl | Cl[c:6]1[n:5][cH:4][cH:3][c:2]([Cl:1])[cH:14]1.[NH2:7][c:8]1[n:9][cH:10][cH:11][cH:12][n:13]1>>[Cl:1][c:2]1[cH:3][cH:4][n:5][c:6]([NH:7][c:8]2[n:9][cH:10][cH:11][cH:12][n:13]2)[cH:14]1 | Clc1ccnc(Cl)c1.Nc1ncccn1 | Clc1ccnc(Nc2ncccn2)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncccn2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[#7;a:8]:[c:9]):[#7;a:10]:[c:11]>>[c:11]:[#7;a:10]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[#7;a:8]:[c:9] | 51.71 | [{"value": 51.71, "product": "C1=CN=C(N=C1)NC2=NC=CC(=C2)Cl", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Palladium(II) acetate (0.061 g, 0.27 mmol) was added to 2,4-dichloropyridine (0.500 g, 3.38 mmol), 2-Aminopyrimidine (0.321 g, 3.38 mmol), 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (0.235 g, 0.41 mmol) and Cesium carbonate (2.202 g, 6.76 mmol) in dioxane (15 mL) at 20ºC under nitrogen. The resulting suspension wa... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1cncnc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | Clc1ccnc(Cl)c1.Nc1ncccn1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>Clc1ccnc(Nc2ncccn2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-89c8603d021344778ef0d6ba16c5f635 | Clc1ccnc(Cl)c1.Nc1ncccn1>>Clc1ccnc(Nc2ncccn2)c1 | C1=CN=C(C=C1Cl)Cl.C1=CN=C(N=C1)N>>C1=CN=C(N=C1)NC2=NC=CC(=C2)Cl | Cl[c:6]1[n:5][cH:4][cH:3][c:2]([Cl:1])[cH:14]1.[NH2:7][c:8]1[n:9][cH:10][cH:11][cH:12][n:13]1>>[Cl:1][c:2]1[cH:3][cH:4][n:5][c:6]([NH:7][c:8]2[n:9][cH:10][cH:11][cH:12][n:13]2)[cH:14]1 | Clc1ccnc(Cl)c1.Nc1ncccn1 | Clc1ccnc(Nc2ncccn2)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncccn2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[#7;a:8]:[c:9]):[#7;a:10]:[c:11]>>[c:11]:[#7;a:10]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[#7;a:8]:[c:9] | 55.35 | [{"value": 55.35, "product": "C1=CN=C(N=C1)NC2=NC=CC(=C2)Cl", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Palladium(II) acetate (0.607 g, 2.70 mmol) was added to 2,4-dichloropyridine (5.00 g, 33.79 mmol), 2-Aminopyrimidine (3.21 g, 33.79 mmol), 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (2.346 g, 4.05 mmol) and Cesium carbonate (22.02 g, 67.57 mmol) in dioxane (15 mL) at 20ºC under nitrogen. The resulting suspension w... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1cncnc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | Clc1ccnc(Cl)c1.Nc1ncccn1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>Clc1ccnc(Nc2ncccn2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-a0aa244ac0f34a23886d9e4b9c227fa6 | CC(=O)Nc1cc(N)ccc1C.Cn1cnc(Nc2cc(Cl)nc3c(C#N)cnn23)c1>>CC(=O)Nc1cc(Nc2cc(Nc3cn(C)cn3)n3ncc(C#N)c3n2)ccc1C | CN1C=C(N=C1)NC2=CC(=NC3=C(C=NN23)C#N)Cl.CC1=C(C=C(C=C1)N)NC(=O)C>>CC1=C(C=C(C=C1)NC2=NC3=C(C=NN3C(=C2)NC4=CN(C=N4)C)C#N)NC(=O)C | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH2:8])[cH:27][cH:28][c:29]1[CH3:30].Cl[c:9]1[cH:10][c:11]([NH:12][c:13]2[cH:14][n:15]([CH3:16])[cH:17][n:18]2)[n:19]2[n:20][cH:21][c:22]([C:23]#[N:24])[c:25]2[n:26]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH:8][c:9]2[cH:10][c:11]([NH:12][c:13]3[cH:14][n:15]([CH3:16])... | CC(=O)Nc1cc(N)ccc1C.Cn1cnc(Nc2cc(Cl)nc3c(C#N)cnn23)c1 | CC(=O)Nc1cc(Nc2cc(Nc3cn(C)cn3)n3ncc(C#N)c3n2)ccc1C | CC(C)(C)[O-].[Na+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 6a0a0ea430a7870620c3d4d20fcc8903f46074a0b3c6c18ae32245490105a12e | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cc(Nc3c[nH]cn3)n3nccc3n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:2:[c:8](-[#7:9]):[c:10]:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#7:9]-[c:8]1:[c:10]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:1:2 | 12.78 | [{"value": 12.78, "product": "CC1=C(C=C(C=C1)NC2=NC3=C(C=NN3C(=C2)NC4=CN(C=N4)C)C#N)NC(=O)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | To a microwave vial containing N-(5-amino-2-methylphenyl)acetamide (0.096 g, 0.58 mmol), 5-chloro-7-(1-methyl-1H-imidazol-4-ylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (0.08 g, 0.29 mmol), sodium tert-butoxide (0.093 g, 0.96 mmol) and 2-Dicyclohexylphosphino-2',4',6'-tri-iso-propyl-1,1'-biphenyl (0.014 g, 0.03 mmo... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2ccnn2c1 | c1cnc2ccnn2c1 | c1ccccc1.c1c[nH]cn1.c1cnc2ccnn2c1 | HCl | CC(C)(C)[O-].[Na+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC(=O)N(C)C | 100 | null | CC(=O)Nc1cc(N)ccc1C.Cn1cnc(Nc2cc(Cl)nc3c(C#N)cnn23)c1>CC(C)(C)[O-].[Na+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC(=O)N(C)C>CC(=O)Nc1cc(Nc2cc(Nc3cn(C)cn3)n3ncc(C#N)c3... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-85b6b1948aa842f2a19dc52c1d84fd97 | CC(=O)Nc1cc(N)ccc1C.Cn1cnc(Nc2cc(Cl)nc3c(C#N)cnn23)c1>>CC(=O)Nc1cc(Nc2cc(Nc3cn(C)cn3)n3ncc(C#N)c3n2)ccc1C | CN1C=C(N=C1)NC2=CC(=NC3=C(C=NN23)C#N)Cl.CC1=C(C=C(C=C1)N)NC(=O)C>>CC1=C(C=C(C=C1)NC2=NC3=C(C=NN3C(=C2)NC4=CN(C=N4)C)C#N)NC(=O)C | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH2:8])[cH:27][cH:28][c:29]1[CH3:30].Cl[c:9]1[cH:10][c:11]([NH:12][c:13]2[cH:14][n:15]([CH3:16])[cH:17][n:18]2)[n:19]2[n:20][cH:21][c:22]([C:23]#[N:24])[c:25]2[n:26]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH:8][c:9]2[cH:10][c:11]([NH:12][c:13]3[cH:14][n:15]([CH3:16])... | CC(=O)Nc1cc(N)ccc1C.Cn1cnc(Nc2cc(Cl)nc3c(C#N)cnn23)c1 | CC(=O)Nc1cc(Nc2cc(Nc3cn(C)cn3)n3ncc(C#N)c3n2)ccc1C | CC(C)(C)[O-].[Na+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 6a0a0ea430a7870620c3d4d20fcc8903f46074a0b3c6c18ae32245490105a12e | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cc(Nc3c[nH]cn3)n3nccc3n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:2:[c:8](-[#7:9]):[c:10]:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#7:9]-[c:8]1:[c:10]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:1:2 | 29.32 | [{"value": 29.32, "product": "CC1=C(C=C(C=C1)NC2=NC3=C(C=NN3C(=C2)NC4=CN(C=N4)C)C#N)NC(=O)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | To a microwave vial containingN-(5-amino-2-methylphenyl)acetamide (0.120 g, 0.73 mmol), 5-chloro-7-(1-methyl-1H-imidazol-4-ylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (0.1 g, 0.37 mmol) ,sodium 2-methylpropan-2-olate (0.116 g, 1.21 mmol) and 2-Dicyclohexylphosphino-2',4',6'-tri-iso-propyl-1,1'-biphenyl (0.017 g, 0... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2ccnn2c1 | c1cnc2ccnn2c1 | c1ccccc1.c1c[nH]cn1.c1cnc2ccnn2c1 | HCl | CC(C)(C)[O-].[Na+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC(=O)N(C)C | 100 | null | CC(=O)Nc1cc(N)ccc1C.Cn1cnc(Nc2cc(Cl)nc3c(C#N)cnn23)c1>CC(C)(C)[O-].[Na+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC(=O)N(C)C>CC(=O)Nc1cc(Nc2cc(Nc3cn(C)cn3)n3ncc(C#N)c3... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-619d0fe2a4c84781a991f3b254737c7e | CC(=O)Nc1cc(N)ccc1N(C)CCO.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>>CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)ccc1N(C)CCO | C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl.CC(=O)NC1=C(C=CC(=C1)N)N(C)CCO>>CC(=O)NC1=C(C=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)N(C)CCO | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH2:8])[cH:24][cH:25][c:26]1[N:27]([CH3:28])[CH2:29][CH2:30][OH:31].Cl[c:9]1[cH:10][c:11]([NH:12][CH:13]2[CH2:14][CH2:15]2)[n:16]2[n:17][cH:18][c:19]([C:20]#[N:21])[c:22]2[n:23]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH:8][c:9]2[cH:10][c:11]([NH:12][CH:13]3[CH2:14][C... | CC(=O)Nc1cc(N)ccc1N(C)CCO.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12 | CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)ccc1N(C)CCO | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 6a0a0ea430a7870620c3d4d20fcc8903f46074a0b3c6c18ae32245490105a12e | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cc(NC3CC3)n3nccc3n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:2:[c:8](-[#7:9]):[c:10]:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#7:9]-[c:8]1:[c:10]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:1:2 | 50.94 | [{"value": 50.94, "product": "CC(=O)NC1=C(C=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)N(C)CCO", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | In a 40mL vial (t=g) was 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (120mg, 0.51 mmol), N-(5-amino-2-((2-hydroxyethyl)(methyl)amino)phenyl)acetamide (115 mg, 0.51 mmol), and cesium carbonate (335 mg, 1.03 mmol) in DMA (3.0 mL) (),Pd2(dba)3 (23.51 mg, 0.03 mmol) and (9,9-dimethyl-9H-xanthene-4... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2ccnn2c1 | c1cnc2ccnn2c1 | c1ccccc1.C1CC1.c1cnc2ccnn2c1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC(=O)N(C)C | 150 | null | CC(=O)Nc1cc(N)ccc1N(C)CCO.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC(=O)N(C)C>CC(=O)Nc1c... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-e6180464a6454b249422de6171dce6f3 | Brc1cccnc1.O=C(C1CC2(CCNCC2)C1)N1CCN(C2CCC2)CC1>>O=C(C1CC2(CCN(c3cccnc3)CC2)C1)N1CCN(C2CCC2)CC1 | C1=CC(=CN=C1)Br.C1CC(C1)N2CCN(CC2)C(=O)C3CC4(C3)CCNCC4>>C1CC(C1)N2CCN(CC2)C(=O)C3CC4(C3)CCN(CC4)C5=CN=CC=C5 | Br[c:9]1[cH:10][cH:11][cH:12][n:13][cH:14]1.[O:1]=[C:2]([CH:3]1[CH2:4][C:5]2([CH2:6][CH2:7][NH:8][CH2:15][CH2:16]2)[CH2:17]1)[N:18]1[CH2:19][CH2:20][N:21]([CH:22]2[CH2:23][CH2:24][CH2:25]2)[CH2:26][CH2:27]1>>[O:1]=[C:2]([CH:3]1[CH2:4][C:5]2([CH2:6][CH2:7][N:8]([c:9]3[cH:10][cH:11][cH:12][n:13][cH:14]3)[CH2:15][CH2:16]2... | Brc1cccnc1.O=C(C1CC2(CCNCC2)C1)N1CCN(C2CCC2)CC1 | O=C(C1CC2(CCN(c3cccnc3)CC2)C1)N1CCN(C2CCC2)CC1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 75377ac1e22f3738296927ba29d3f942a20b96a4f93f0c857f61f0541f1f6447 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=C(C1CC2(CCN(c3cccnc3)CC2)C1)N1CCN(C2CCC2)CC1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1)-[C:10]-[C:11] | 7.91 | [{"value": 7.91, "product": "C1CC(C1)N2CCN(CC2)C(=O)C3CC4(C3)CCN(CC4)C5=CN=CC=C5", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | cesium carbonate (123 mg, 0.38 mmol) was added to a solution of (4-cyclobutylpiperazin-1-yl)(7-azaspiro[3.5]nonan-2-yl)methanone (100 mg, 0.34 mmol), PdOAc2 (7.70 mg, 0.03 mmol), BINAP (42.7 mg, 0.07 mmol) and 3-bromopyridine (56.9 mg, 0.36 mmol) in toluene (2 mL). The reaction mixture was heated to 110°C for 18hrs. Th... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccncc1.C1CC2(C1)CCNCC2 | C1CC2(C1)CC[NH]CC2.c1ccncc1 | C1CC2(C1)CC[NH]CC2.c1ccncc1.C1C[NH]CC[NH]1.C1CCC1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 110 | null | Brc1cccnc1.O=C(C1CC2(CCNCC2)C1)N1CCN(C2CCC2)CC1>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>O=C(C1CC2(CCN(c3cccnc3)CC2)C1)N1CCN(C2CCC2)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-ca7fdadedf3340de8e255025b11294fe | CC(C)[C@@H]1CNCCN1C(=O)OC(C)(C)C.COc1ccc(Br)cc1OC>>COc1ccc(N2CCN(C(=O)OC(C)(C)C)[C@H](C(C)C)C2)cc1OC | COC1=C(C=C(C=C1)Br)OC.CC(C)[C@@H]1CNCCN1C(=O)OC(C)(C)C>>CC(C)[C@@H]1CN(CCN1C(=O)OC(C)(C)C)C2=CC(=C(C=C2)OC)OC | [NH:7]1[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[C@H:18]([CH:19]([CH3:20])[CH3:21])[CH2:22]1.Br[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:24]([O:25][CH3:26])[cH:23]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[... | CC(C)[C@@H]1CNCCN1C(=O)OC(C)(C)C.COc1ccc(Br)cc1OC | COc1ccc(N2CCN(C(=O)OC(C)(C)C)[C@H](C(C)C)C2)cc1OC | CC(C)(C)[O-].[Na+] | CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 75de53007ec0cb91435746fdefbf3b121f745fc71ddebd19c6e45a5212b3f56a | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | 36 | [{"value": 36.0, "product": "CC(C)[C@@H]1CN(CCN1C(=O)OC(C)(C)C)C2=CC(=C(C=C2)OC)OC", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | 21-Apr-09 08:58:54 +0100 4-bromo-1,2-dimethoxybenzene (0.068 mL, 0.46 mmol), (R)-tert-butyl 2-isopropylpiperazine-1-carboxylate (126 mg, 0.55 mmol) and 2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl (11.21 mg, 0.03 mmol) and Sodium tert-butoxide (63.9 mg, 0.64 mmol) and Tris(dibenzylideneacetone)dipalladium(0)... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ccccc1 | c1ccccc1.C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1 | HBr | CC(C)(C)[O-].[Na+].CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 150 | null | CC(C)[C@@H]1CNCCN1C(=O)OC(C)(C)C.COc1ccc(Br)cc1OC>CC(C)(C)[O-].[Na+].CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>COc1ccc(N2CCN(C(=O)OC(C)(C)C)[C@H](C(C)C)C2)cc1OC |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-8ac590d4cc01454e9f3c19a34317cb92 | CC(C)[C@@H]1CNCCN1C(=O)OC(C)(C)C.COc1ccc(Br)cc1OC>>COc1ccc(N2CCN(C(=O)OC(C)(C)C)[C@H](C(C)C)C2)cc1OC | COC1=C(C=C(C=C1)Br)OC.CC(C)[C@@H]1CNCCN1C(=O)OC(C)(C)C>>CC(C)[C@@H]1CN(CCN1C(=O)OC(C)(C)C)C2=CC(=C(C=C2)OC)OC | [NH:7]1[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[C@H:18]([CH:19]([CH3:20])[CH3:21])[CH2:22]1.Br[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:24]([O:25][CH3:26])[cH:23]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[... | CC(C)[C@@H]1CNCCN1C(=O)OC(C)(C)C.COc1ccc(Br)cc1OC | COc1ccc(N2CCN(C(=O)OC(C)(C)C)[C@H](C(C)C)C2)cc1OC | CC(C)(C)[O-].[Na+] | CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 75de53007ec0cb91435746fdefbf3b121f745fc71ddebd19c6e45a5212b3f56a | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | 60 | [{"value": 60.0, "product": "CC(C)[C@@H]1CN(CCN1C(=O)OC(C)(C)C)C2=CC(=C(C=C2)OC)OC", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | 21-Apr-09 08:58:54 +0100 4-bromo-1,2-dimethoxybenzene (0.135 mL, 0.92 mmol), (R)-tert-butyl 2-isopropylpiperazine-1-carboxylate (252 mg, 1.11 mmol) and 2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl (10.88 mg, 0.03 mmol) and Sodium tert-butoxide (128 mg, 1.29 mmol) and Tris(dibenzylideneacetone)dipalladium(0) ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ccccc1 | c1ccccc1.C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1 | HBr | CC(C)(C)[O-].[Na+].CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 150 | null | CC(C)[C@@H]1CNCCN1C(=O)OC(C)(C)C.COc1ccc(Br)cc1OC>CC(C)(C)[O-].[Na+].CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>COc1ccc(N2CCN(C(=O)OC(C)(C)C)[C@H](C(C)C)C2)cc1OC |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-dcac8bcfa5124a8baee8e28e5e992678 | CC(C)[C@@H]1CNCCN1C(=O)OC(C)(C)C.COc1ccc(Br)cc1OC>>COc1ccc(N2CCN(C(=O)OC(C)(C)C)[C@H](C(C)C)C2)cc1OC | COC1=C(C=C(C=C1)Br)OC.CC(C)[C@@H]1CNCCN1C(=O)OC(C)(C)C>>CC(C)[C@@H]1CN(CCN1C(=O)OC(C)(C)C)C2=CC(=C(C=C2)OC)OC | [NH:7]1[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[C@H:18]([CH:19]([CH3:20])[CH3:21])[CH2:22]1.Br[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:24]([O:25][CH3:26])[cH:23]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[... | CC(C)[C@@H]1CNCCN1C(=O)OC(C)(C)C.COc1ccc(Br)cc1OC | COc1ccc(N2CCN(C(=O)OC(C)(C)C)[C@H](C(C)C)C2)cc1OC | CC(C)(C)[O-].[K+] | CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.[Pd] | C1CCOC1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 75de53007ec0cb91435746fdefbf3b121f745fc71ddebd19c6e45a5212b3f56a | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | 90.52 | [{"value": 90.52, "product": "CC(C)[C@@H]1CN(CCN1C(=O)OC(C)(C)C)C2=CC(=C(C=C2)OC)OC", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | 22-Apr-09 09:56:23 +0100 4-bromo-1,2-dimethoxybenzene (0.068 mL, 0.46 mmol), (R)-tert-butyl 2-isopropylpiperazine-1-carboxylate (126 mg, 0.55 mmol) and BIS(TRI-T- BUTYLPHOSPHINE)PALLADIUM(0) (23.54 mg, 0.05 mmol) and potassium 2-methylpropan-2-olate (76 mg, 0.64 mmol) were suspended in THF (5 mL) and sealed into a mic... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ccccc1 | c1ccccc1.C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1 | HBr | CC(C)(C)[O-].[K+].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.[Pd].C1CCOC1 | 150 | null | CC(C)[C@@H]1CNCCN1C(=O)OC(C)(C)C.COc1ccc(Br)cc1OC>CC(C)(C)[O-].[K+].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.[Pd].C1CCOC1>COc1ccc(N2CCN(C(=O)OC(C)(C)C)[C@H](C(C)C)C2)cc1OC |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-849a1d763cb042f7907069ab25fe470c | CC(C)(C)OC(N)=O.Cc1nc(Cl)ccc1F>>Cc1nc(NC(=O)OC(C)(C)C)ccc1F | CC1=C(C=CC(=N1)Cl)F.CC(C)(C)OC(=O)N>>CC1=C(C=CC(=N1)NC(=O)OC(C)(C)C)F | [NH2:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12].Cl[c:4]1[n:3][c:2]([CH3:1])[c:15]([F:16])[cH:14][cH:13]1>>[CH3:1][c:2]1[n:3][c:4]([NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[cH:13][cH:14][c:15]1[F:16] | CC(C)(C)OC(N)=O.Cc1nc(Cl)ccc1F | Cc1nc(NC(=O)OC(C)(C)C)ccc1F | [O-]P(=O)([O-])[O-].[K+].[K+].[K+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Goldberg coupling | ed01b145192f9cffb3f3553513f8bbd15ca4f246fc1ccc0dad392a1f0f7069ce | 23f4e0d8af1d86d8b907685b9e69e28ed17e2c9c83b8194f1d8a52eb89f58564 | c1ccncc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[#8:10]-[C:11](-[NH2;D1;+0:12])=[O;D1;H0:13]>>[C;D1;H3:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[#8:10]-[C:11](=[O;D1;H0:13])-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 0 | [{"value": 0.0, "product": "CC1=C(C=CC(=N1)NC(=O)OC(C)(C)C)F", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | A mixture of 6-chloro-3-fluoro-2-methylpyridine (500 mg, 3.43 mmol), tert- Butyl carbamate (523 mg, 4.47 mmol), Potassium phosphate (1094 mg, 5.15 mmol), 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (99 mg, 0.17 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (79 mg, 0.09 mmol) were combined in a sealed vial whic... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Carbamic ester | Carbamic ester | c1ccncc1 | c1ccncc1 | c1ccncc1 | HCl | [O-]P(=O)([O-])[O-].[K+].[K+].[K+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 90 | null | CC(C)(C)OC(N)=O.Cc1nc(Cl)ccc1F>[O-]P(=O)([O-])[O-].[K+].[K+].[K+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>Cc1nc(NC(=O)OC(C)(C)C)ccc1... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-0986b91ec7734959810ebeac46571d3f | CN1CCNCC1.COC(=O)c1cc(Br)cc([N+](=O)[O-])c1>>COC(=O)c1cc(N2CCN(C)CC2)cc([N+](=O)[O-])c1 | COC(=O)C1=CC(=CC(=C1)Br)[N+](=O)[O-].CN1CCNCC1>>CN1CCN(CC1)C2=CC(=CC(=C2)C(=O)OC)[N+](=O)[O-] | [NH:8]1[CH2:9][CH2:10][N:11]([CH3:12])[CH2:13][CH2:14]1.Br[c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:20][c:16]([N+:17](=[O:18])[O-:19])[cH:15]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([N:8]2[CH2:9][CH2:10][N:11]([CH3:12])[CH2:13][CH2:14]2)[cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20]1 | CN1CCNCC1.COC(=O)c1cc(Br)cc([N+](=O)[O-])c1 | COC(=O)c1cc(N2CCN(C)CC2)cc([N+](=O)[O-])c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 75de53007ec0cb91435746fdefbf3b121f745fc71ddebd19c6e45a5212b3f56a | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]-[C:6](-[#8:7])=[O;D1;H0:8].[#7:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[#8:7]-[C:6](=[O;D1;H0:8])-[c:5]:[c:4]:[c;H0;D3;+0:1](-[N;H0;D3;+0:12]1-[C:13]-[C:14]-[#7:9]-[C:10]-[C:11]-1):[c:2]:[c:3] | 65.18 | [{"value": 65.18, "product": "CN1CCN(CC1)C2=CC(=CC(=C2)C(=O)OC)[N+](=O)[O-]", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | To the stirred suspension ofmethyl 3-bromo-5-nitrobenzoate (2 g, 7.69 mmol) , cesium carbonate (12.53 g, 38.46 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.111 g, 0.19 mmol) in Dioxane (12 mL) (degassed with N2) was added pd (dba)3 (0.176 g, 0.19 mmol) and cesium carbonate (12.53 g, 38.46 mmol... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ccccc1 | c1ccccc1.C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 110 | null | CN1CCNCC1.COC(=O)c1cc(Br)cc([N+](=O)[O-])c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>COC(=O)c1cc(N2CCN(C)CC2)... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-7a7d88bb15974f808c2ac9e73fb46a04 | C1CNCCN1.Cc1ccc(Br)cc1[N+](=O)[O-]>>Cc1ccc(N2CCNCC2)cc1[N+](=O)[O-] | CC1=C(C=C(C=C1)Br)[N+](=O)[O-].C1CNCCN1>>CC1=C(C=C(C=C1)N2CCNCC2)[N+](=O)[O-] | [NH:6]1[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]1.Br[c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:13]([N+:14](=[O:15])[O-:16])[cH:12]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([N:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]2)[cH:12][c:13]1[N+:14](=[O:15])[O-:16] | C1CNCCN1.Cc1ccc(Br)cc1[N+](=O)[O-] | Cc1ccc(N2CCNCC2)cc1[N+](=O)[O-] | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 1d452876efa46787ecd5eab4acf018720843b51fbe40244616ffd72f6a602335 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | 39.25 | [{"value": 39.25, "product": "CC1=C(C=C(C=C1)N2CCNCC2)[N+](=O)[O-]", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | palladium(II) acetate (0.065 g, 0.29 mmol), BINAP (0.144 g, 0.23 mmol) and CS2CO3 (0.943 g, 2.89 mmol) were added to a mixture of 4-bromo-1-methyl-2-nitrobenzene (0.5 g, 2.31 mmol) and piperazine (1.623 g, 18.84 mmol) . The suspension were heated to 110 °C for 24 hours, LCMS showed product mass [M+1]: 222.1 at retensio... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1ccccc1 | c1ccccc1.C1C[NH]CCN1 | c1ccccc1.C1C[NH]CCN1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 110 | null | C1CNCCN1.Cc1ccc(Br)cc1[N+](=O)[O-]>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>Cc1ccc(N2CCNCC2)cc1[N+](=O)[O-] |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-160ce7a57c0f456d8f6b62d0a7b77bc4 | C1CNCCN1.Cc1ccc(Br)cc1[N+](=O)[O-]>>Cc1ccc(N2CCNCC2)cc1[N+](=O)[O-] | CC1=C(C=C(C=C1)Br)[N+](=O)[O-].C1CNCCN1>>CC1=C(C=C(C=C1)N2CCNCC2)[N+](=O)[O-] | [NH:6]1[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]1.Br[c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:13]([N+:14](=[O:15])[O-:16])[cH:12]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([N:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]2)[cH:12][c:13]1[N+:14](=[O:15])[O-:16] | C1CNCCN1.Cc1ccc(Br)cc1[N+](=O)[O-] | Cc1ccc(N2CCNCC2)cc1[N+](=O)[O-] | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 1d452876efa46787ecd5eab4acf018720843b51fbe40244616ffd72f6a602335 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | 54.35 | [{"value": 54.35, "product": "CC1=C(C=C(C=C1)N2CCNCC2)[N+](=O)[O-]", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | palladium(II) acetate (0.390 g, 1.74 mmol), BINAP (0.865 g, 1.39 mmol) and CS2CO3 (5.66 g, 17.36 mmol) were added to a mixture of 4-bromo-1-methyl-2-nitrobenzene (3 g, 13.89 mmol) and piperazine (9.74 g, 113.04 mmol) in microwave. The suspension were heated to 110 °C for 24 hours, LCMS showed product mass [M+1]: 222.0 ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1ccccc1 | c1ccccc1.C1C[NH]CCN1 | c1ccccc1.C1C[NH]CCN1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 110 | null | C1CNCCN1.Cc1ccc(Br)cc1[N+](=O)[O-]>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>Cc1ccc(N2CCNCC2)cc1[N+](=O)[O-] |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-b55c5711f803482494d33a05fbba3389 | CC(=O)Nc1cc(N)c(F)cc1C.N#Cc1cnn2c(NC3CCC3)cc(Cl)nc12>>CC(=O)Nc1cc(Nc2cc(NC3CCC3)n3ncc(C#N)c3n2)c(F)cc1C | C1CC(C1)NC2=CC(=NC3=C(C=NN23)C#N)Cl.CC1=CC(=C(C=C1NC(=O)C)N)F>>CC1=CC(=C(C=C1NC(=O)C)NC2=NC3=C(C=NN3C(=C2)NC4CCC4)C#N)F | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH2:8])[c:25]([F:26])[cH:27][c:28]1[CH3:29].Cl[c:9]1[cH:10][c:11]([NH:12][CH:13]2[CH2:14][CH2:15][CH2:16]2)[n:17]2[n:18][cH:19][c:20]([C:21]#[N:22])[c:23]2[n:24]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH:8][c:9]2[cH:10][c:11]([NH:12][CH:13]3[CH2:14][CH2:15][CH2:16]3)... | CC(=O)Nc1cc(N)c(F)cc1C.N#Cc1cnn2c(NC3CCC3)cc(Cl)nc12 | CC(=O)Nc1cc(Nc2cc(NC3CCC3)n3ncc(C#N)c3n2)c(F)cc1C | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 6a0a0ea430a7870620c3d4d20fcc8903f46074a0b3c6c18ae32245490105a12e | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cc(NC3CCC3)n3nccc3n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:2:[c:8](-[#7:9]):[c:10]:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#7:9]-[c:8]1:[c:10]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:1:2 | 5.51 | [{"value": 5.51, "product": "CC1=CC(=C(C=C1NC(=O)C)NC2=NC3=C(C=NN3C(=C2)NC4CCC4)C#N)F", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | 5-chloro-7-(cyclobutylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (80 mg, 0.32 mmol), N-(5-amino-4-fluoro-2-methylphenyl)acetamide (58.8 mg, 0.32 mmol), and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (18.69 mg, 0.03 mmol) in DMA (5 mL) were added to a microwave tube. Pd2(dba)3 (14.79 mg, 0.02 mmol) a... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2ccnn2c1 | c1cnc2ccnn2c1 | c1ccccc1.C1CCC1.c1cnc2ccnn2c1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC(=O)N(C)C | 150 | null | CC(=O)Nc1cc(N)c(F)cc1C.N#Cc1cnn2c(NC3CCC3)cc(Cl)nc12>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC(=O)N(C)C>CC(=O)Nc1cc(... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-4224929cdb884295951cf91f4fb5b988 | CC(C)(C)OC(=O)N1CCNCC1.FC(F)(F)c1cnc(Cl)cn1>>CC(C)(C)OC(=O)N1CCN(c2cnc(C(F)(F)F)cn2)CC1 | C1=C(N=CC(=N1)Cl)C(F)(F)F.CC(C)(C)OC(=O)N1CCNCC1>>CC(C)(C)OC(=O)N1CCN(CC1)C2=NC=C(N=C2)C(F)(F)F | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:22][CH2:23]1.Cl[c:12]1[cH:13][n:14][c:15]([C:16]([F:17])([F:18])[F:19])[cH:20][n:21]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][n:14][c:15]([C:16]([F:17])([F:18])[F:19])[cH:20][n:21]2)[CH2:... | CC(C)(C)OC(=O)N1CCNCC1.FC(F)(F)c1cnc(Cl)cn1 | CC(C)(C)OC(=O)N1CCN(c2cnc(C(F)(F)F)cn2)CC1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 343e2e4205e268ef018e3d4960cb45b93370e1763fb33dc0e04e91f5357b5af3 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cnc(N2CCNCC2)cn1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[#7:7]1-[C:8]-[C:9]-[N;H0;D3;+0:10](-[c;H0;D3;+0:1]2:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:2)-[C:11]-[C:12]-1 | 21.41 | [{"value": 21.41, "product": "CC(C)(C)OC(=O)N1CCN(CC1)C2=NC=C(N=C2)C(F)(F)F", "details": "", "is_desired": true}] | 105 | CELSIUS | null | null | A 20 mL microwave vial was charged with 2-chloro-5-(trifluoromethyl)pyrazine (1 g, 5.48 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.341 g, 0.55 mmol), Sodium tert-butoxide (0.632 g, 6.57 mmol), tert-butyl piperazine-1-carboxylate (1.020 g, 5.48 mmol) and a mixture of toluene (25 mL) and DMF (5 mL). The re... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1cnccn1 | C1C[NH]CC[NH]1.c1cnccn1 | C1C[NH]CC[NH]1.c1cnccn1 | HCl | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 105 | null | CC(C)(C)OC(=O)N1CCNCC1.FC(F)(F)c1cnc(Cl)cn1>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>CC(C)(C)OC(=O)N1CCN... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-70ea34f4ab314aa093c5c77488bf98e8 | CC(C)(C)OC(=O)N1CCNCC1.Clc1ccc2ccccc2n1>>CC(C)(C)OC(=O)N1CCN(c2ccc3ccccc3n2)CC1 | C1=CC=C2C(=C1)C=CC(=N2)Cl.CC(C)(C)OC(=O)N1CCNCC1>>CC(C)(C)OC(=O)N1CCN(CC1)C2=NC3=CC=CC=C3C=C2 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:22][CH2:23]1.Cl[c:12]1[cH:13][cH:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[n:21]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][cH:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]3[n:21]2)[CH2:... | CC(C)(C)OC(=O)N1CCNCC1.Clc1ccc2ccccc2n1 | CC(C)(C)OC(=O)N1CCN(c2ccc3ccccc3n2)CC1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 9f69c5c4a4ea31f8d76ec3987be7bd40b9cb34092e5d3f4fe2f7075ca0afa5f4 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc2nc(N3CCNCC3)ccc2c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:10]-[C:11]-[#7:6]-[C:7]-[C:8]-1):[#7;a:2]:[c:3] | 46.36 | [{"value": 46.36, "product": "CC(C)(C)OC(=O)N1CCN(CC1)C2=NC3=CC=CC=C3C=C2", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | A 2.0-5.0 mL microwave vial was charged with tert-Butyl 1-piperazinecarboxylate (100 mg, 0.54 mmol), 2-Chloroquinoline (0.086 mL, 0.64 mmol), Sodium tert-butoxide (61.9 mg, 0.64 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (33.4 mg, 0.05 mmol) and toluene (3 mL). The reaction mixture was degassed for 10 minut... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1ccc2ncccc2c1 | C1C[NH]CC[NH]1.c1ccc2ncccc2c1 | C1C[NH]CC[NH]1.c1ccc2ncccc2c1 | HCl | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 100 | null | CC(C)(C)OC(=O)N1CCNCC1.Clc1ccc2ccccc2n1>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>CC(C)(C)OC(=O)N1CCN(c2c... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-96460abed19147c3abf8fef3ac794b48 | CC(=O)Nc1cc(N)ncc1C.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>>CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)ncc1C | C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl.CC1=CN=C(C=C1NC(=O)C)N>>CC1=CN=C(C=C1NC(=O)C)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH2:8])[n:24][cH:25][c:26]1[CH3:27].Cl[c:9]1[cH:10][c:11]([NH:12][CH:13]2[CH2:14][CH2:15]2)[n:16]2[n:17][cH:18][c:19]([C:20]#[N:21])[c:22]2[n:23]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH:8][c:9]2[cH:10][c:11]([NH:12][CH:13]3[CH2:14][CH2:15]3)[n:16]3[n:17][cH:18][c:1... | CC(=O)Nc1cc(N)ncc1C.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12 | CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)ncc1C | C(=O)([O-])[O-].[Cs+].[Cs+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CN(C)C=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 6a0a0ea430a7870620c3d4d20fcc8903f46074a0b3c6c18ae32245490105a12e | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cc(NC3CC3)n3nccc3n2)nc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:2:[c:8](-[#7:9]):[c:10]:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[#7;a:14]:[c:15]>>[#7:9]-[c:8]1:[c:10]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[#7;a:14]:[c:15]):[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:1:2 | 10.6 | [{"value": 10.6, "product": "CC1=CN=C(C=C1NC(=O)C)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | Ref: _Angew. Chem. Int. Ed._ **2006** , _45_ , 6523-6527 1\. To a microwave tube was added N-(2-amino-5-methylpyridin-4-yl)acetamide (43 mg, 0.26 mmol), 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (85 mg, 0.36 mmol), Cs2CO3 (254 mg, 0.78 mmol), Pd2dba3 (23.84 mg, 0.03 mmol), and di- tert-buty... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2ccnn2c1 | c1cnc2ccnn2c1 | c1ccncc1.C1CC1.c1cnc2ccnn2c1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CN(C)C=O | 90 | null | CC(=O)Nc1cc(N)ncc1C.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CN(C)C=O>CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)n... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-9afd80193ebe4d909351826d5e746d73 | FC(F)(F)c1cccc(Br)c1.OC1CCNCC1>>OC1CCN(c2cccc(C(F)(F)F)c2)CC1 | C1=CC(=CC(=C1)Br)C(F)(F)F.C1CNCCC1O>>C1CN(CCC1O)C2=CC=CC(=C2)C(F)(F)F | Br[c:6]1[cH:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]1.[OH:1][CH:2]1[CH2:3][CH2:4][NH:5][CH2:16][CH2:17]1>>[OH:1][CH:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]2)[CH2:16][CH2:17]1 | FC(F)(F)c1cccc(Br)c1.OC1CCNCC1 | OC1CCN(c2cccc(C(F)(F)F)c2)CC1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | ad5ec9c4592e4dee5877fc4f1309a503a378773e18ebc21adf780b709f6e28c5 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCCCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:9]-[C:10] | 43.09 | [{"value": 43.09, "product": "C1CN(CCC1O)C2=CC=CC(=C2)C(F)(F)F", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | A mixture of 1-bromo-3-(trifluoromethyl)benzene (6.13 mL, 44.44 mmol), piperidin-4-ol (5.608 g, 55.44 mmol), diacetoxypalladium (0.200 g, 0.89 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.553 g, 0.89 mmol) and cesium carbonate (18.10 g, 55.55 mmol) in dioxane (100 mL) was evacuated and backfilled with N2 three... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.C1CCNCC1 | C1CC[NH]CC1.c1ccccc1 | C1CC[NH]CC1.c1ccccc1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | FC(F)(F)c1cccc(Br)c1.OC1CCNCC1>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>OC1CCN(c2cccc(C(F)(F)F)c2)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-13cef69f8e724020954e5476c0d66794 | Brc1cccc(Br)n1.NC1CCOCC1>>Brc1cccc(NC2CCOCC2)n1 | C1=CC(=NC(=C1)Br)Br.C1COCCC1N>>C1COCCC1NC2=NC(=CC=C2)Br | Br[c:6]1[cH:5][cH:4][cH:3][c:2]([Br:1])[n:14]1.[NH2:7][CH:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1>>[Br:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][CH:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[n:14]1 | Brc1cccc(Br)n1.NC1CCOCC1 | Brc1cccc(NC2CCOCC2)n1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(NC2CCOCC2)nc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7](-[NH2;D1;+0:8])-[C:9]>>[C:6]-[C:7](-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5])-[C:9] | 0 | [{"value": 0.0, "product": "C1COCCC1NC2=NC(=CC=C2)Br", "details": "", "is_desired": true}] | null | CELSIUS | null | null | to 2,6-dibromopyridine (100 mg, 0.42 mmol), 4-Aminotetrahydropyran (42.7 mg, 0.42 mmol) in dioxane (3 mL) while bubbling N2 was added Xantphos (24.43 mg, 0.04 mmol), CS2CO3 (316 mg, 0.97 mmol) and palladium(II) acetate (9.48 mg, 0.04 mmol). This was heated in a microwave at 130 oC for 30 mins. A small peak correspondin... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.C1CCOCC1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | null | null | Brc1cccc(Br)n1.NC1CCOCC1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>Brc1cccc(NC2CCOCC2)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-ee0c75ae423d4c13a290870b1caf79ed | CC(=O)Nc1cc(N)ccc1C.N#Cc1cnn2c(NC3COC3)cc(Cl)nc12>>CC(=O)Nc1cc(Nc2cc(NC3COC3)n3ncc(C#N)c3n2)ccc1C | C1C(CO1)NC2=CC(=NC3=C(C=NN23)C#N)Cl.CC1=C(C=C(C=C1)N)NC(=O)C>>CC1=C(C=C(C=C1)NC2=NC3=C(C=NN3C(=C2)NC4COC4)C#N)NC(=O)C | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH2:8])[cH:25][cH:26][c:27]1[CH3:28].Cl[c:9]1[cH:10][c:11]([NH:12][CH:13]2[CH2:14][O:15][CH2:16]2)[n:17]2[n:18][cH:19][c:20]([C:21]#[N:22])[c:23]2[n:24]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH:8][c:9]2[cH:10][c:11]([NH:12][CH:13]3[CH2:14][O:15][CH2:16]3)[n:17]3[n:1... | CC(=O)Nc1cc(N)ccc1C.N#Cc1cnn2c(NC3COC3)cc(Cl)nc12 | CC(=O)Nc1cc(Nc2cc(NC3COC3)n3ncc(C#N)c3n2)ccc1C | C(=O)([O-])[O-].[Cs+].[Cs+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 6a0a0ea430a7870620c3d4d20fcc8903f46074a0b3c6c18ae32245490105a12e | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cc(NC3COC3)n3nccc3n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:2:[c:8](-[#7:9]):[c:10]:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#7:9]-[c:8]1:[c:10]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:1:2 | 16.54 | [{"value": 16.54, "product": "CC1=C(C=C(C=C1)NC2=NC3=C(C=NN3C(=C2)NC4COC4)C#N)NC(=O)C", "details": "", "is_desired": true}] | 145 | CELSIUS | null | null | In a microwave tube, was Cs2CO3 (0.522 g, 1.60 mmol), N-(5-amino-2-methylphenyl)acetamide (0.132 g, 0.80 mmol), Pd2dba3 (0.037 g, 0.04 mmol),5-chloro-7-(oxetan-3-ylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (0.200 g, 0.80 mmol),di-tert- butyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-2-yl)phosphine (0.034 g, 0.08 mmol)... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2ccnn2c1 | c1cnc2ccnn2c1 | c1ccccc1.C1COC1.c1cnc2ccnn2c1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC(=O)N(C)C | 145 | null | CC(=O)Nc1cc(N)ccc1C.N#Cc1cnn2c(NC3COC3)cc(Cl)nc12>C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC(=O)N(C)C>CC(=O)Nc1cc(Nc2cc(NC3COC3)n3ncc(C#N)c... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-453f34fcdc374f919797959874dcc393 | COc1nc(N)ncc1Br.Fc1ccc(C(F)(F)F)cc1I>>COc1nc(Nc2cc(C(F)(F)F)ccc2F)ncc1Br | C1=CC(=C(C=C1C(F)(F)F)I)F.COC1=NC(=NC=C1Br)N>>COC1=NC(=NC=C1Br)NC2=C(C=CC(=C2)C(F)(F)F)F | [CH3:1][O:2][c:3]1[n:4][c:5]([NH2:6])[n:18][cH:19][c:20]1[Br:21].I[c:7]1[cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15][c:16]1[F:17]>>[CH3:1][O:2][c:3]1[n:4][c:5]([NH:6][c:7]2[cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15][c:16]2[F:17])[n:18][cH:19][c:20]1[Br:21] | COc1nc(N)ncc1Br.Fc1ccc(C(F)(F)F)cc1I | COc1nc(Nc2cc(C(F)(F)F)ccc2F)ncc1Br | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncccn2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[#7;a:9]:[c:10]):[#7;a:11]:[c:12]>>[F;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[#7;a:9]:[c:10]):[#7;a:11]:[c:12]):[c:2]:[c:3] | 84.88 | [{"value": 84.88, "product": "COC1=NC(=NC=C1Br)NC2=C(C=CC(=C2)C(F)(F)F)F", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | To a microwave vial was added a mixture of 5-bromo-4-methoxypyrimidin-2-amine (0.520 g, 2.55 mmol), diacetoxypalladium (0.059 g, 0.26 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (151.8 mg, 0.26 mmol), 1-fluoro-2-iodo-4-(trifluoromethyl)benzene (0.89 g, 3.07 mmol) and toluene (17 mL) under inert atm... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1cncnc1.c1ccccc1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 100 | null | COc1nc(N)ncc1Br.Fc1ccc(C(F)(F)F)cc1I>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>COc1nc(Nc2cc(C(F)(F)F)ccc2F)ncc1Br |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-49d889221a9546a98e62a35726966f57 | COc1nc(N)ncc1Br.Fc1ccc(C(F)(F)F)cc1I>>COc1nc(Nc2cc(C(F)(F)F)ccc2F)ncc1Br | C1=CC(=C(C=C1C(F)(F)F)I)F.COC1=NC(=NC=C1Br)N>>COC1=NC(=NC=C1Br)NC2=C(C=CC(=C2)C(F)(F)F)F | [CH3:1][O:2][c:3]1[n:4][c:5]([NH2:6])[n:18][cH:19][c:20]1[Br:21].I[c:7]1[cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15][c:16]1[F:17]>>[CH3:1][O:2][c:3]1[n:4][c:5]([NH:6][c:7]2[cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15][c:16]2[F:17])[n:18][cH:19][c:20]1[Br:21] | COc1nc(N)ncc1Br.Fc1ccc(C(F)(F)F)cc1I | COc1nc(Nc2cc(C(F)(F)F)ccc2F)ncc1Br | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncccn2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[#7;a:9]:[c:10]):[#7;a:11]:[c:12]>>[F;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[#7;a:9]:[c:10]):[#7;a:11]:[c:12]):[c:2]:[c:3] | 80.85 | [{"value": 80.85, "product": "COC1=NC(=NC=C1Br)NC2=C(C=CC(=C2)C(F)(F)F)F", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | To a microwave vial was added a mixture of 5-bromo-4-methoxypyrimidin-2-amine (0.570 g, 2.79 mmol), diacetoxypalladium (0.059 g, 0.26 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (152.9 mg, 0.26 mmol), 1-fluoro-2-iodo-4-(trifluoromethyl)benzene (0.99 g, 3.41 mmol) and toluene (17 mL) under inert atm... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1cncnc1.c1ccccc1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 100 | null | COc1nc(N)ncc1Br.Fc1ccc(C(F)(F)F)cc1I>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>COc1nc(Nc2cc(C(F)(F)F)ccc2F)ncc1Br |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-dd547470ed614a60b02e180b7f0d2acd | Brc1ccccn1.O=C(C1CC12CCNCC2)N1CCN(C2CCC2)CC1>>O=C(C1CC12CCN(c1ccccn1)CC2)N1CCN(C2CCC2)CC1 | C1=CC=NC(=C1)Br.C1CC(C1)N2CCN(CC2)C(=O)C3CC34CCNCC4>>C1CC(C1)N2CCN(CC2)C(=O)C3CC34CCN(CC4)C5=CC=CC=N5 | Br[c:9]1[cH:10][cH:11][cH:12][cH:13][n:14]1.[O:1]=[C:2]([CH:3]1[CH2:4][C:5]12[CH2:6][CH2:7][NH:8][CH2:15][CH2:16]2)[N:17]1[CH2:18][CH2:19][N:20]([CH:21]2[CH2:22][CH2:23][CH2:24]2)[CH2:25][CH2:26]1>>[O:1]=[C:2]([CH:3]1[CH2:4][C:5]12[CH2:6][CH2:7][N:8]([c:9]1[cH:10][cH:11][cH:12][cH:13][n:14]1)[CH2:15][CH2:16]2)[N:17]1[C... | Brc1ccccn1.O=C(C1CC12CCNCC2)N1CCN(C2CCC2)CC1 | O=C(C1CC12CCN(c1ccccn1)CC2)N1CCN(C2CCC2)CC1 | CC(C)(C)[O-].[Na+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | fcc883ceeaa8f8240ae09dd6f213c06e7ad4d210adb9394510891d9617759001 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=C(C1CC12CCN(c1ccccn1)CC2)N1CCN(C2CCC2)CC1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5])-[C:9]-[C:10] | 26.61 | [{"value": 26.61, "product": "C1CC(C1)N2CCN(CC2)C(=O)C3CC34CCN(CC4)C5=CC=CC=N5", "details": "", "is_desired": true}] | 160 | CELSIUS | null | null | (4-cyclobutylpiperazin-1-yl)(6-azaspiro[2.5]octan-1-yl)methanone (100 mg, 0.36 mmol), Sodium tert-butoxide (34.6 mg, 0.36 mmol) and 2-bromopyridine (62.7 mg, 0.40 mmol) were weighted in a microwave vial. A solution of Palladium(II) acetate (4.05 mg, 0.02 mmol) and dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphi... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccncc1.C1CC2(CCN1)CC2 | C1CC2(CC[NH]1)CC2.c1ccncc1 | C1CC2(CC[NH]1)CC2.c1ccncc1.C1C[NH]CC[NH]1.C1CCC1 | HBr | CC(C)(C)[O-].[Na+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 160 | null | Brc1ccccn1.O=C(C1CC12CCNCC2)N1CCN(C2CCC2)CC1>CC(C)(C)[O-].[Na+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>O=C(C1CC12CCN(c1ccccn1)CC2)N1CCN(C2CCC2)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-c35b162a34bf408282b33e4af9af7634 | Brc1ccccn1.O=C(C1CC12CCNCC2)N1CCN(C2CCC2)CC1>>O=C(C1CC12CCN(c1ccccn1)CC2)N1CCN(C2CCC2)CC1 | C1=CC=NC(=C1)Br.C1CC(C1)N2CCN(CC2)C(=O)C3CC34CCNCC4>>C1CC(C1)N2CCN(CC2)C(=O)C3CC34CCN(CC4)C5=CC=CC=N5 | Br[c:9]1[cH:10][cH:11][cH:12][cH:13][n:14]1.[O:1]=[C:2]([CH:3]1[CH2:4][C:5]12[CH2:6][CH2:7][NH:8][CH2:15][CH2:16]2)[N:17]1[CH2:18][CH2:19][N:20]([CH:21]2[CH2:22][CH2:23][CH2:24]2)[CH2:25][CH2:26]1>>[O:1]=[C:2]([CH:3]1[CH2:4][C:5]12[CH2:6][CH2:7][N:8]([c:9]1[cH:10][cH:11][cH:12][cH:13][n:14]1)[CH2:15][CH2:16]2)[N:17]1[C... | Brc1ccccn1.O=C(C1CC12CCNCC2)N1CCN(C2CCC2)CC1 | O=C(C1CC12CCN(c1ccccn1)CC2)N1CCN(C2CCC2)CC1 | CC(C)(C)[O-].[Na+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.CC(=O)O.CC(=O)O.[Pd] | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | fcc883ceeaa8f8240ae09dd6f213c06e7ad4d210adb9394510891d9617759001 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=C(C1CC12CCN(c1ccccn1)CC2)N1CCN(C2CCC2)CC1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5])-[C:9]-[C:10] | 9.39 | [{"value": 9.39, "product": "C1CC(C1)N2CCN(CC2)C(=O)C3CC34CCN(CC4)C5=CC=CC=N5", "details": "", "is_desired": true}] | 160 | CELSIUS | null | null | Reagents were put in a sealed vial and heated in the microwave oven for 10 minutes at 160°C. According to LC-MS analysis, the conversion is >90%. The crude mixture was transferred to a round-bottomed flask and volatiles were evaporated under vacuum. The residue was purified on preparative HPLC using the long high pH (a... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccncc1.C1CC2(CCN1)CC2 | C1CC2(CC[NH]1)CC2.c1ccncc1 | C1CC2(CC[NH]1)CC2.c1ccncc1.C1C[NH]CC[NH]1.C1CCC1 | HBr | CC(C)(C)[O-].[Na+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.CC(=O)O.CC(=O)O.[Pd] | 160 | null | Brc1ccccn1.O=C(C1CC12CCNCC2)N1CCN(C2CCC2)CC1>CC(C)(C)[O-].[Na+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.CC(=O)O.CC(=O)O.[Pd]>O=C(C1CC12CCN(c1ccccn1)CC2)N1CCN(C2CCC2)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-e0d4157f08c0492097a16f50798a4aa4 | N#Cc1cnn2c(NC3CC3)cc(Cl)nc12.OCc1ccc2cc[nH]c2c1>>N#Cc1cnn2c(NC3CC3)cc(-n3ccc4ccc(CO)cc43)nc12 | C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl.C1=CC(=CC2=C1C=CN2)CO>>C1CC1NC2=CC(=NC3=C(C=NN23)C#N)N4C=CC5=C4C=C(C=C5)CO | Cl[c:13]1[cH:12][c:7]([NH:8][CH:9]2[CH2:10][CH2:11]2)[n:6]2[n:5][cH:4][c:3]([C:2]#[N:1])[c:26]2[n:25]1.[nH:14]1[cH:15][cH:16][c:17]2[cH:18][cH:19][c:20]([CH2:21][OH:22])[cH:23][c:24]12>>[N:1]#[C:2][c:3]1[cH:4][n:5][n:6]2[c:7]([NH:8][CH:9]3[CH2:10][CH2:11]3)[cH:12][c:13](-[n:14]3[cH:15][cH:16][c:17]4[cH:18][cH:19][c:20]... | N#Cc1cnn2c(NC3CC3)cc(Cl)nc12.OCc1ccc2cc[nH]c2c1 | N#Cc1cnn2c(NC3CC3)cc(-n3ccc4ccc(CO)cc43)nc12 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | OtherReaction | 48025c2763e0e3b48dbecc700d7fb3bbd37c460b1e39276d3b0985ae78de45ab | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc2c(c1)ccn2-c1cc(NC2CC2)n2nccc2n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:2:[c:8](-[#7:9]):[c:10]:1.[c:11]:[c:12]1:[c:13]:[c:14]:[c:15]:[nH;D2;+0:16]:1>>[#7:9]-[c:8]1:[c:10]:[c;H0;D3;+0:1](-[n;H0;D3;+0:16]2:[c:15]:[c:14]:[c:13]:[c:12]:2:[c:11]):[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:2:1 | 47.5 | [{"value": 47.5, "product": "C1CC1NC2=CC(=NC3=C(C=NN23)C#N)N4C=CC5=C4C=C(C=C5)CO", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | In a 40mL vial (t=g) was 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (50 mg, 0.21 mmol), [Reactants], and cesium carbonate (77 mg, 0.24 mmol) in DMA (0.5 mL) ([VOLUME]),Pd2(dba)3 (9.80 mg, 10.70 µmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (12.38 mg, 0.02 mmol) were adde... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide | null | c1cnc2ccnn2c1.c1ccc2[nH]ccc2c1 | c1cnc2ccnn2c1.c1ccc2cc[nH]c2c1 | C1CC1.c1cnc2ccnn2c1.c1ccc2cc[nH]c2c1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC(=O)N(C)C | 150 | null | N#Cc1cnn2c(NC3CC3)cc(Cl)nc12.OCc1ccc2cc[nH]c2c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC(=O)N(C)C>N#Cc1cnn2c(NC3CC3... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-a86dba2ccd9142e390883516f628700c | CC(=O)Nc1cc(N)ccc1N1CCN(C)CC1.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>>CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)ccc1N1CCN(C)CC1 | C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl.CC(=O)NC1=C(C=CC(=C1)N)N2CCN(CC2)C>>CC(=O)NC1=C(C=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)N5CCN(CC5)C | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH2:8])[cH:24][cH:25][c:26]1[N:27]1[CH2:28][CH2:29][N:30]([CH3:31])[CH2:32][CH2:33]1.Cl[c:9]1[cH:10][c:11]([NH:12][CH:13]2[CH2:14][CH2:15]2)[n:16]2[n:17][cH:18][c:19]([C:20]#[N:21])[c:22]2[n:23]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH:8][c:9]2[cH:10][c:11]([NH:12][... | CC(=O)Nc1cc(N)ccc1N1CCN(C)CC1.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12 | CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)ccc1N1CCN(C)CC1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 6a0a0ea430a7870620c3d4d20fcc8903f46074a0b3c6c18ae32245490105a12e | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc2nc(Nc3ccc(N4CCNCC4)cc3)cc(NC3CC3)n2n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:2:[c:8](-[#7:9]):[c:10]:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#7:9]-[c:8]1:[c:10]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:1:2 | 32.78 | [{"value": 32.78, "product": "CC(=O)NC1=C(C=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)N5CCN(CC5)C", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | In a 40mL vial (t=g) was 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (80 mg, 0.34 mmol), [Reactants], and cesium carbonate (145 mg, 0.45 mmol) in DMA (0.5 mL) ([VOLUME]),Pd2(dba)3 (15.68 mg, 0.02 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (19.81 mg, 0.03 mmol) were add... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2ccnn2c1 | c1cnc2ccnn2c1 | c1ccccc1.C1CC1.c1cnc2ccnn2c1.C1C[NH]CC[NH]1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC(=O)N(C)C | 150 | null | CC(=O)Nc1cc(N)ccc1N1CCN(C)CC1.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC(=O)N(C)C>CC(=O)... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-879a784e2da64b7f993840feec5d14ac | CC(C)(C)OC(=O)N1CCNCC1.COC(=O)c1ccc(Br)cc1Cl>>COC(=O)c1ccc(N2CCN(C(=O)OC(C)(C)C)CC2)cc1Cl | COC(=O)C1=C(C=C(C=C1)Br)Cl.CC(C)(C)OC(=O)N1CCNCC1>>CC(C)(C)OC(=O)N1CCN(CC1)C2=CC(=C(C=C2)C(=O)OC)Cl | [NH:9]1[CH2:10][CH2:11][N:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:20][CH2:21]1.Br[c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:23]([Cl:24])[cH:22]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([N:9]2[CH2:10][CH2:11][N:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:... | CC(C)(C)OC(=O)N1CCNCC1.COC(=O)c1ccc(Br)cc1Cl | COC(=O)c1ccc(N2CCN(C(=O)OC(C)(C)C)CC2)cc1Cl | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 75de53007ec0cb91435746fdefbf3b121f745fc71ddebd19c6e45a5212b3f56a | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | 90.88 | [{"value": 90.88, "product": "CC(C)(C)OC(=O)N1CCN(CC1)C2=CC(=C(C=C2)C(=O)OC)Cl", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | To a solution of palladium acetate (18.00 mg, 0.08 mmol) in dry toluene (16 mL) under nitrogen was added BINAP (100 mg, 0.16 mmol). The reaction was heated to 80 °C and stirred for 10 min. To the reaction was then added tert- butyl piperazine-1-carboxylate (299 mg, 1.60 mmol), cesium carbonate (261 mg, 0.80 mmol), pota... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ccccc1 | c1ccccc1.C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 80 | null | CC(C)(C)OC(=O)N1CCNCC1.COC(=O)c1ccc(Br)cc1Cl>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>COC(=O)c1ccc(N2CCN(C(=O)OC(C)(C)C)CC2)cc1Cl |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-a242bdcea6fd4820b97f40b83c063cc9 | CC(=O)Nc1cc(N)ccc1C1CC1.N#Cc1cnn2c(NC3COC3)cc(Cl)nc12>>CC(=O)Nc1cc(Nc2cc(NC3COC3)n3ncc(C#N)c3n2)ccc1C1CC1 | C1C(CO1)NC2=CC(=NC3=C(C=NN23)C#N)Cl.CC(=O)NC1=C(C=CC(=C1)N)C2CC2>>CC(=O)NC1=C(C=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4COC4)C#N)C5CC5 | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH2:8])[cH:25][cH:26][c:27]1[CH:28]1[CH2:29][CH2:30]1.Cl[c:9]1[cH:10][c:11]([NH:12][CH:13]2[CH2:14][O:15][CH2:16]2)[n:17]2[n:18][cH:19][c:20]([C:21]#[N:22])[c:23]2[n:24]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH:8][c:9]2[cH:10][c:11]([NH:12][CH:13]3[CH2:14][O:15][CH2... | CC(=O)Nc1cc(N)ccc1C1CC1.N#Cc1cnn2c(NC3COC3)cc(Cl)nc12 | CC(=O)Nc1cc(Nc2cc(NC3COC3)n3ncc(C#N)c3n2)ccc1C1CC1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 6a0a0ea430a7870620c3d4d20fcc8903f46074a0b3c6c18ae32245490105a12e | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc2nc(Nc3ccc(C4CC4)cc3)cc(NC3COC3)n2n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:2:[c:8](-[#7:9]):[c:10]:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#7:9]-[c:8]1:[c:10]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:1:2 | 6.96 | [{"value": 6.96, "product": "CC(=O)NC1=C(C=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4COC4)C#N)C5CC5", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | A 10 mL microwave reactor vial was charged with 5-chloro-7-(oxetan-3-ylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (80 mg, 0.32 mmol), N-(5-amino-2-cyclopropylphenyl)acetamide (67.1 mg, 0.35 mmol), Cs2CO3 (313 mg, 0.96 mmol), Pd2(dba)3 (14.67 mg, 0.02 mmol) and 2-Di-t- butylphosphino-2',4',6'-tri-i-propyl-1,1'-biphe... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2ccnn2c1 | c1cnc2ccnn2c1 | c1ccccc1.C1COC1.c1cnc2ccnn2c1.C1CC1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC(=O)N(C)C | 150 | null | CC(=O)Nc1cc(N)ccc1C1CC1.N#Cc1cnn2c(NC3COC3)cc(Cl)nc12>C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC(=O)N(C)C>CC(=O)Nc1cc(Nc2cc(NC3COC3)n3ncc(C... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-6ca5406ed1914cc08b2221358d36ecf3 | CC(=O)Nc1cc(N)ccc1C1CC1.N#Cc1cnn2c(NC3COC3)cc(Cl)nc12>>CC(=O)Nc1cc(Nc2cc(NC3COC3)n3ncc(C#N)c3n2)ccc1C1CC1 | C1C(CO1)NC2=CC(=NC3=C(C=NN23)C#N)Cl.CC(=O)NC1=C(C=CC(=C1)N)C2CC2>>CC(=O)NC1=C(C=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4COC4)C#N)C5CC5 | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH2:8])[cH:25][cH:26][c:27]1[CH:28]1[CH2:29][CH2:30]1.Cl[c:9]1[cH:10][c:11]([NH:12][CH:13]2[CH2:14][O:15][CH2:16]2)[n:17]2[n:18][cH:19][c:20]([C:21]#[N:22])[c:23]2[n:24]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH:8][c:9]2[cH:10][c:11]([NH:12][CH:13]3[CH2:14][O:15][CH2... | CC(=O)Nc1cc(N)ccc1C1CC1.N#Cc1cnn2c(NC3COC3)cc(Cl)nc12 | CC(=O)Nc1cc(Nc2cc(NC3COC3)n3ncc(C#N)c3n2)ccc1C1CC1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CN(C)C=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 6a0a0ea430a7870620c3d4d20fcc8903f46074a0b3c6c18ae32245490105a12e | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc2nc(Nc3ccc(C4CC4)cc3)cc(NC3COC3)n2n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:2:[c:8](-[#7:9]):[c:10]:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#7:9]-[c:8]1:[c:10]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:1:2 | 0 | [{"value": 0.0, "product": "CC(=O)NC1=C(C=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4COC4)C#N)C5CC5", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | Ref: _Angew. Chem. Int. Ed._ **2006** , _45_ , 6523-6527 1\. To a microwave tube was added N-(5-amino-2-cyclopropylphenyl)acetamide (0.038 g, 0.20 mmol), 5-chloro-7-(oxetan-3-ylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (0.060 g, 0.24 mmol), Cs2CO3 (0.196 g, 0.60 mmol), Pd2dba3 (0.018 g, 0.02 mmol), and di-tert-bu... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2ccnn2c1 | c1cnc2ccnn2c1 | c1ccccc1.C1COC1.c1cnc2ccnn2c1.C1CC1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CN(C)C=O | 90 | null | CC(=O)Nc1cc(N)ccc1C1CC1.N#Cc1cnn2c(NC3COC3)cc(Cl)nc12>C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CN(C)C=O>CC(=O)Nc1cc(Nc2cc(NC3COC3)n3ncc(C#N)... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-475c89db99fe4f418713bc4636a30c0a | CC(=O)Nc1cc(N)ccc1C1CC1.N#Cc1cnn2c(NC3COC3)cc(Cl)nc12>>CC(=O)Nc1cc(Nc2cc(NC3COC3)n3ncc(C#N)c3n2)ccc1C1CC1 | C1C(CO1)NC2=CC(=NC3=C(C=NN23)C#N)Cl.CC(=O)NC1=C(C=CC(=C1)N)C2CC2>>CC(=O)NC1=C(C=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4COC4)C#N)C5CC5 | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH2:8])[cH:25][cH:26][c:27]1[CH:28]1[CH2:29][CH2:30]1.Cl[c:9]1[cH:10][c:11]([NH:12][CH:13]2[CH2:14][O:15][CH2:16]2)[n:17]2[n:18][cH:19][c:20]([C:21]#[N:22])[c:23]2[n:24]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH:8][c:9]2[cH:10][c:11]([NH:12][CH:13]3[CH2:14][O:15][CH2... | CC(=O)Nc1cc(N)ccc1C1CC1.N#Cc1cnn2c(NC3COC3)cc(Cl)nc12 | CC(=O)Nc1cc(Nc2cc(NC3COC3)n3ncc(C#N)c3n2)ccc1C1CC1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 6a0a0ea430a7870620c3d4d20fcc8903f46074a0b3c6c18ae32245490105a12e | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc2nc(Nc3ccc(C4CC4)cc3)cc(NC3COC3)n2n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:2:[c:8](-[#7:9]):[c:10]:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#7:9]-[c:8]1:[c:10]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:1:2 | 8.66 | [{"value": 8.66, "product": "CC(=O)NC1=C(C=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4COC4)C#N)C5CC5", "details": "", "is_desired": true}] | 145 | CELSIUS | null | null | In a microwave tube, was Cs2CO3 (0.522 g, 1.60 mmol), N-(5-amino-2-cyclopropylphenyl)acetamide (0.152 g, 0.80 mmol), Pd2dba3 (0.037 g, 0.04 mmol),5-chloro-7-(oxetan-3-ylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (0.200 g, 0.80 mmol),di-tert- butyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (0.034 g, 0.08 mmol). a... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2ccnn2c1 | c1cnc2ccnn2c1 | c1ccccc1.C1COC1.c1cnc2ccnn2c1.C1CC1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC(=O)N(C)C | 145 | null | CC(=O)Nc1cc(N)ccc1C1CC1.N#Cc1cnn2c(NC3COC3)cc(Cl)nc12>C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC(=O)N(C)C>CC(=O)Nc1cc(Nc2cc(NC3COC3)n3ncc(C... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-6a2cb6eee4e6411fbe36a812955f2574 | CC(=O)Nc1cc(N)ccc1N1CCC[C@@H](N(C)C)C1.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>>CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)ccc1N1CCC[C@@H](N(C)C)C1 | C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl.CC(=O)NC1=C(C=CC(=C1)N)N2CCC[C@H](C2)N(C)C>>CC(=O)NC1=C(C=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)N5CCC[C@H](C5)N(C)C | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH2:8])[cH:24][cH:25][c:26]1[N:27]1[CH2:28][CH2:29][CH2:30][C@@H:31]([N:32]([CH3:33])[CH3:34])[CH2:35]1.Cl[c:9]1[cH:10][c:11]([NH:12][CH:13]2[CH2:14][CH2:15]2)[n:16]2[n:17][cH:18][c:19]([C:20]#[N:21])[c:22]2[n:23]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH:8][c:9]2[cH... | CC(=O)Nc1cc(N)ccc1N1CCC[C@@H](N(C)C)C1.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12 | CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)ccc1N1CCC[C@@H](N(C)C)C1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 6a0a0ea430a7870620c3d4d20fcc8903f46074a0b3c6c18ae32245490105a12e | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc2nc(Nc3ccc(N4CCCCC4)cc3)cc(NC3CC3)n2n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:2:[c:8](-[#7:9]):[c:10]:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#7:9]-[c:8]1:[c:10]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:1:2 | 7.29 | [{"value": 7.29, "product": "CC(=O)NC1=C(C=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)N5CCC[C@H](C5)N(C)C", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | In a 40mL vial (t=g) was 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (120mg, 0.51 mmol), (R)-N-(5-amino-2-(3-(dimethylamino)piperidin-1-yl)phenyl)acetamide (142 mg, 0.51 mmol), and cesium carbonate (335 mg, 1.03 mmol) in DMA (0.5 mL) (),Pd2(dba)3 (23.51 mg, 0.03 mmol) and (9,9-dimethyl-9H-xant... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2ccnn2c1 | c1cnc2ccnn2c1 | c1ccccc1.C1CC1.c1cnc2ccnn2c1.C1CC[NH]CC1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC(=O)N(C)C | 150 | null | CC(=O)Nc1cc(N)ccc1N1CCC[C@@H](N(C)C)C1.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC(=O)N(C... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-ef6fa44581ae45349778e22c890419e5 | CC(N)c1cc(C(=O)N(C)C)cc2c(=O)cc(N3CCOCC3)oc12.Fc1cc(F)c(F)c(Br)c1>>CC(Nc1cc(F)cc(F)c1F)c1cc(C(=O)N(C)C)cc2c(=O)cc(N3CCOCC3)oc12 | C1=C(C=C(C(=C1F)F)Br)F.CC(C1=CC(=CC2=C1OC(=CC2=O)N3CCOCC3)C(=O)N(C)C)N>>CC(C1=CC(=CC2=C1OC(=CC2=O)N3CCOCC3)C(=O)N(C)C)NC4=C(C(=CC(=C4)F)F)F | [CH3:1][CH:2]([NH2:3])[c:13]1[cH:14][c:15]([C:16](=[O:17])[N:18]([CH3:19])[CH3:20])[cH:21][c:22]2[c:23](=[O:24])[cH:25][c:26]([N:27]3[CH2:28][CH2:29][O:30][CH2:31][CH2:32]3)[o:33][c:34]12.Br[c:4]1[cH:5][c:6]([F:7])[cH:8][c:9]([F:10])[c:11]1[F:12]>>[CH3:1][CH:2]([NH:3][c:4]1[cH:5][c:6]([F:7])[cH:8][c:9]([F:10])[c:11]1[F... | CC(N)c1cc(C(=O)N(C)C)cc2c(=O)cc(N3CCOCC3)oc12.Fc1cc(F)c(F)c(Br)c1 | CC(Nc1cc(F)cc(F)c1F)c1cc(C(=O)N(C)C)cc2c(=O)cc(N3CCOCC3)oc12 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1cc(N2CCOCC2)oc2c(CNc3ccccc3)cccc12 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].[#8;a:7]:[c:8]:[c:9]-[C:10](-[C;D1;H3:11])-[NH2;D1;+0:12]>>[#8;a:7]:[c:8]:[c:9]-[C:10](-[C;D1;H3:11])-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6] | 83.02 | [{"value": 83.02, "product": "CC(C1=CC(=CC2=C1OC(=CC2=O)N3CCOCC3)C(=O)N(C)C)NC4=C(C(=CC(=C4)F)F)F", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | To a mixture of 8-(1-aminoethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide (350 mg, 1.01 mmol), cesium carbonate (1288 mg, 3.95 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (147 mg, 0.25 mmol) and 1-bromo-2,3,5-trifluorobenzene (470 mg, 2.23 mmol) in degassed 1,4-dioxane (2.2ml), was... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2occcc2c1.C1COCC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 90 | null | CC(N)c1cc(C(=O)N(C)C)cc2c(=O)cc(N3CCOCC3)oc12.Fc1cc(F)c(F)c(Br)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>CC... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-bcc19de9bb794d1ea8d67a62b78fce0d | CC(=O)Nc1cc(N)ccc1C.Cn1ccc(Nc2cc(Cl)nc3c(C#N)cnn23)n1>>CC(=O)Nc1cc(Nc2cc(Nc3ccn(C)n3)n3ncc(C#N)c3n2)ccc1C | CN1C=CC(=N1)NC2=CC(=NC3=C(C=NN23)C#N)Cl.CC1=C(C=C(C=C1)N)NC(=O)C>>CC1=C(C=C(C=C1)NC2=NC3=C(C=NN3C(=C2)NC4=NN(C=C4)C)C#N)NC(=O)C | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH2:8])[cH:27][cH:28][c:29]1[CH3:30].Cl[c:9]1[cH:10][c:11]([NH:12][c:13]2[cH:14][cH:15][n:16]([CH3:17])[n:18]2)[n:19]2[n:20][cH:21][c:22]([C:23]#[N:24])[c:25]2[n:26]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH:8][c:9]2[cH:10][c:11]([NH:12][c:13]3[cH:14][cH:15][n:16]([C... | CC(=O)Nc1cc(N)ccc1C.Cn1ccc(Nc2cc(Cl)nc3c(C#N)cnn23)n1 | CC(=O)Nc1cc(Nc2cc(Nc3ccn(C)n3)n3ncc(C#N)c3n2)ccc1C | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 6a0a0ea430a7870620c3d4d20fcc8903f46074a0b3c6c18ae32245490105a12e | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cc(Nc3cc[nH]n3)n3nccc3n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:2:[c:8](-[#7:9]):[c:10]:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#7:9]-[c:8]1:[c:10]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:1:2 | 33.24 | [{"value": 33.24, "product": "CC1=C(C=C(C=C1)NC2=NC3=C(C=NN3C(=C2)NC4=NN(C=C4)C)C#N)NC(=O)C", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | in microwave tube was 5-chloro-7-(1-methyl-1H-pyrazol-3-ylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (80 mg, 0.29 mmol), N-(5-amino-2-methylphenyl)acetamide (48.0 mg, 0.29 mmol), and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (16.91 mg, 0.03 mmol) in DMA (0.5 mL).Pd2(dba)3 (13.38 mg, 0.01 mmol) and c... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2ccnn2c1 | c1cnc2ccnn2c1 | c1ccccc1.c1cc[nH]n1.c1cnc2ccnn2c1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC(=O)N(C)C | 150 | null | CC(=O)Nc1cc(N)ccc1C.Cn1ccc(Nc2cc(Cl)nc3c(C#N)cnn23)n1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC(=O)N(C)C>CC(=O)Nc1cc... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-edbe9e3659f844c9af0347af857ae822 | CC(=O)Nc1cc(N)c(F)cc1C.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>>CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)c(F)cc1C | C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl.CC1=CC(=C(C=C1NC(=O)C)N)F>>CC1=CC(=C(C=C1NC(=O)C)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)F | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH2:8])[c:24]([F:25])[cH:26][c:27]1[CH3:28].Cl[c:9]1[cH:10][c:11]([NH:12][CH:13]2[CH2:14][CH2:15]2)[n:16]2[n:17][cH:18][c:19]([C:20]#[N:21])[c:22]2[n:23]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH:8][c:9]2[cH:10][c:11]([NH:12][CH:13]3[CH2:14][CH2:15]3)[n:16]3[n:17][cH... | CC(=O)Nc1cc(N)c(F)cc1C.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12 | CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)c(F)cc1C | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 6a0a0ea430a7870620c3d4d20fcc8903f46074a0b3c6c18ae32245490105a12e | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cc(NC3CC3)n3nccc3n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:2:[c:8](-[#7:9]):[c:10]:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#7:9]-[c:8]1:[c:10]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:1:2 | 16.17 | [{"value": 16.17, "product": "CC1=CC(=C(C=C1NC(=O)C)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)F", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | in microwave tube was 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (80 mg, 0.34 mmol), N-(5-amino-4-fluoro-2-methylphenyl)acetamide (62.4 mg, 0.34 mmol), and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (19.81 mg, 0.03 mmol) in DMA (0.5 mL).Pd2(dba)3 (15.68 mg, 0.02 mmol) and cesiu... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2ccnn2c1 | c1cnc2ccnn2c1 | c1ccccc1.C1CC1.c1cnc2ccnn2c1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC(=O)N(C)C | 150 | null | CC(=O)Nc1cc(N)c(F)cc1C.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC(=O)N(C)C>CC(=O)Nc1cc(N... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-6fb2cc503861494889cc8f39d864a898 | CC(C)(C)OC(=O)N1CCNCC1.Fc1cc(Br)ccc1C(F)(F)F>>CC(C)(C)OC(=O)N1CCN(c2ccc(C(F)(F)F)c(F)c2)CC1 | C1=CC(=C(C=C1Br)F)C(F)(F)F.CC(C)(C)OC(=O)N1CCNCC1>>CC(C)(C)OC(=O)N1CCN(CC1)C2=CC(=C(C=C2)C(F)(F)F)F | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:23][CH2:24]1.Br[c:12]1[cH:13][cH:14][c:15]([C:16]([F:17])([F:18])[F:19])[c:20]([F:21])[cH:22]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][cH:14][c:15]([C:16]([F:17])([F:18])[F:19])[c:20]([F:... | CC(C)(C)OC(=O)N1CCNCC1.Fc1cc(Br)ccc1C(F)(F)F | CC(C)(C)OC(=O)N1CCN(c2ccc(C(F)(F)F)c(F)c2)CC1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | d687b31bdda9f407fdde6ca57e67eee0681e173646c617afef7770c56d05bab9 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:10]-[C:11]-[#7:6]-[C:7]-[C:8]-1):[c:4]:[c:5] | 59.92 | [{"value": 59.92, "product": "CC(C)(C)OC(=O)N1CCN(CC1)C2=CC(=C(C=C2)C(F)(F)F)F", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | In a 50 mL round-bottomed flask, PALLADIUM ACETATE (0.014 g, 0.06 mmol) was treated with BINAP (0.077 g, 0.12 mmol) under nitrogen in degassed Toluene (12.35 ml). The reaction was heated to 80 °C and was stirred for 10 min. To the flask was then added tert-butyl piperazine-1-carboxylate (0.230 g, 1.23 mmol), cesium car... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 80 | null | CC(C)(C)OC(=O)N1CCNCC1.Fc1cc(Br)ccc1C(F)(F)F>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>CC(C)(C)OC(=O)N1CCN(c2ccc(C(F)(F)F)c(F)c2)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-b3fb1d017e3744dea3ab3e0ecb0c58d8 | CC(N)c1cc(C(=O)N(C)C)cc2c(=O)cc(N3CCOCC3)oc12.Fc1cc(Cl)cc(Br)c1>>CC(Nc1cc(F)cc(Cl)c1)c1cc(C(=O)N(C)C)cc2c(=O)cc(N3CCOCC3)oc12 | C1=C(C=C(C=C1Cl)Br)F.CC(C1=CC(=CC2=C1OC(=CC2=O)N3CCOCC3)C(=O)N(C)C)N>>CC(C1=CC(=CC2=C1OC(=CC2=O)N3CCOCC3)C(=O)N(C)C)NC4=CC(=CC(=C4)Cl)F | [CH3:1][CH:2]([NH2:3])[c:12]1[cH:13][c:14]([C:15](=[O:16])[N:17]([CH3:18])[CH3:19])[cH:20][c:21]2[c:22](=[O:23])[cH:24][c:25]([N:26]3[CH2:27][CH2:28][O:29][CH2:30][CH2:31]3)[o:32][c:33]12.Br[c:4]1[cH:5][c:6]([F:7])[cH:8][c:9]([Cl:10])[cH:11]1>>[CH3:1][CH:2]([NH:3][c:4]1[cH:5][c:6]([F:7])[cH:8][c:9]([Cl:10])[cH:11]1)[c:... | CC(N)c1cc(C(=O)N(C)C)cc2c(=O)cc(N3CCOCC3)oc12.Fc1cc(Cl)cc(Br)c1 | CC(Nc1cc(F)cc(Cl)c1)c1cc(C(=O)N(C)C)cc2c(=O)cc(N3CCOCC3)oc12 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1cc(N2CCOCC2)oc2c(CNc3ccccc3)cccc12 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8;a:6]:[c:7]:[c:8]-[C:9](-[C;D1;H3:10])-[NH2;D1;+0:11]>>[#8;a:6]:[c:7]:[c:8]-[C:9](-[C;D1;H3:10])-[NH;D2;+0:11]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 78.08 | [{"value": 78.08, "product": "CC(C1=CC(=CC2=C1OC(=CC2=O)N3CCOCC3)C(=O)N(C)C)NC4=CC(=CC(=C4)Cl)F", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | To a mixture of 8-(1-aminoethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide (350 mg, 1.01 mmol), cesium carbonate (1288 mg, 3.95 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (147 mg, 0.25 mmol) and 1-bromo-3-chloro-5-fluorobenzene (467 mg, 2.23 mmol) in degassed 1,4-dioxane (2ml), was... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2occcc2c1.C1COCC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 90 | null | CC(N)c1cc(C(=O)N(C)C)cc2c(=O)cc(N3CCOCC3)oc12.Fc1cc(Cl)cc(Br)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>CC(N... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-1beac9199051463f81c658e8f7cb9a0d | CC(C)(C)OC(=O)c1ccc(Br)cc1.CCOC(=O)C1CCNCC1>>CCOC(=O)C1CCN(c2ccc(C(=O)OC(C)(C)C)cc2)CC1 | CC(C)(C)OC(=O)C1=CC=C(C=C1)Br.CCOC(=O)C1CCNCC1>>CCOC(=O)C1CCN(CC1)C2=CC=C(C=C2)C(=O)OC(C)(C)C | Br[c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[cH:21][cH:22]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][NH:9][CH2:23][CH2:24]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][N:9]([c:10]2[cH:11][cH:12][c:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:2... | CC(C)(C)OC(=O)c1ccc(Br)cc1.CCOC(=O)C1CCNCC1 | CCOC(=O)C1CCN(c2ccc(C(=O)OC(C)(C)C)cc2)CC1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | ad5ec9c4592e4dee5877fc4f1309a503a378773e18ebc21adf780b709f6e28c5 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCCCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:9]-[C:10] | 0 | [{"value": 0.0, "product": "CCOC(=O)C1CCN(CC1)C2=CC=C(C=C2)C(=O)OC(C)(C)C", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | 1\. To a microwave tube was added tert-butyl 4-bromobenzoate (1.328 g, 5.16 mmol), ethyl piperidine-4-carboxylate (1.000 g, 5.16 mmol), Cs2CO3 (5.05 g, 15.49 mmol), Pd2dba3 (0.473 g, 0.52 mmol), and BINAP (0.643 g, 1.03 mmol). The mixture was dissolved in [Solvents] and sealed. The tube was de-gassed and inflated with ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.C1CCNCC1 | C1CC[NH]CC1.c1ccccc1 | C1CC[NH]CC1.c1ccccc1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 110 | null | CC(C)(C)OC(=O)c1ccc(Br)cc1.CCOC(=O)C1CCNCC1>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>CCOC(=O)C1CCN(... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-2d4ae739f81c45c1ab0faf1d764941ef | Brc1cccc2c1ncn2C(c1ccccc1)(c1ccccc1)c1ccccc1.C1CNCCN1>>c1ccc(C(c2ccccc2)(c2ccccc2)n2cnc3c(N4CCNCC4)cccc32)cc1 | C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)N4C=NC5=C4C=CC=C5Br.C1CNCCN1>>C1CN(CCN1)C2=CC=CC3=C2N=CN3C(C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6 | Br[c:22]1[c:21]2[n:20][cH:19][n:18]([C:5]([c:4]3[cH:3][cH:2][cH:1][cH:34][cH:33]3)([c:6]3[cH:7][cH:8][cH:9][cH:10][cH:11]3)[c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[c:32]2[cH:31][cH:30][cH:29]1.[NH:23]1[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]1>>[cH:1]1[cH:2][cH:3][c:4]([C:5]([c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)([... | Brc1cccc2c1ncn2C(c1ccccc1)(c1ccccc1)c1ccccc1.C1CNCCN1 | c1ccc(C(c2ccccc2)(c2ccccc2)n2cnc3c(N4CCNCC4)cccc32)cc1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C(Cl)(Cl)Cl.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 51055b9c270db59871f10d62065659cfd319691f340b2da1ac59faaa616887eb | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(C(c2ccccc2)(c2ccccc2)n2cnc3c(N4CCNCC4)cccc32)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6](-[C:7]):[c:8]:[#7;a:9]:[c:10]:2:1.[#7:11]1-[C:12]-[C:13]-[NH;D2;+0:14]-[C:15]-[C:16]-1>>[C:7]-[#7;a:6]1:[c:8]:[#7;a:9]:[c:10]2:[c:5]:1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:2-[N;H0;D3;+0:14]1-[C:13]-[C:12]-[#7:11]-[C:16]-[C:15]-1 | 42.82 | [{"value": 42.82, "product": "C1CN(CCN1)C2=CC=CC3=C2N=CN3C(C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | A 2.0-5.0 mL microwave vial was charged with 4-bromo-1-trityl-1H-benzo[d]imidazole (300 mg, 0.68 mmol), Sodium tert- butoxide (92 mg, 0.96 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (25.5 mg, 0.04 mmol), Piperazine (0.321 mL, 4.10 mmol) and toluene (5 mL). The reaction mixture was degassed for 10 minutes wi... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1cccc2nc[nH]c12.C1CNCCN1 | C1C[NH]CCN1.c1cccc2[nH]cnc12 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH]CCN1.c1cccc2[nH]cnc12 | HBr | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C(Cl)(Cl)Cl.[Pd].[Pd].CC1=CC=CC=C1 | 90 | null | Brc1cccc2c1ncn2C(c1ccccc1)(c1ccccc1)c1ccccc1.C1CNCCN1>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C(Cl)(Cl)Cl.[Pd].[Pd].CC1=CC=CC=... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-370c3c2e243949c9a11cec4ffc24deb1 | CC(C)(C)OC(=O)N1CCNCC1.Fc1ccc(C(F)(F)F)cc1Br>>CC(C)(C)OC(=O)N1CCN(c2cc(C(F)(F)F)ccc2F)CC1 | C1=CC(=C(C=C1C(F)(F)F)Br)F.CC(C)(C)OC(=O)N1CCNCC1>>CC(C)(C)OC(=O)N1CCN(CC1)C2=C(C=CC(=C2)C(F)(F)F)F | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:23][CH2:24]1.Br[c:12]1[cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20][c:21]1[F:22]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20][c:21... | CC(C)(C)OC(=O)N1CCNCC1.Fc1ccc(C(F)(F)F)cc1Br | CC(C)(C)OC(=O)N1CCN(c2cc(C(F)(F)F)ccc2F)CC1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | d687b31bdda9f407fdde6ca57e67eee0681e173646c617afef7770c56d05bab9 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[F;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:11]-[C:12]-[#7:7]-[C:8]-[C:9]-1):[c:2]:[c:3] | 42.75 | [{"value": 42.75, "product": "CC(C)(C)OC(=O)N1CCN(CC1)C2=C(C=CC(=C2)C(F)(F)F)F", "details": "", "is_desired": true}] | 105 | CELSIUS | null | null | A 250 mL round flask was charged with 2-bromo-1-fluoro-4-(trifluoromethyl)benzene (1.016 g, 4.18 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.260 g, 0.42 mmol), Sodium tert-butoxide (0.482 g, 5.02 mmol), tert-butyl piperazine-1-carboxylate (0.779 g, 4.18 mmol) and a mixture of toluene (25 mL) and DMF (5 mL... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1 | HBr | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 105 | null | CC(C)(C)OC(=O)N1CCNCC1.Fc1ccc(C(F)(F)F)cc1Br>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>CC(C)(C)OC(=O)N1CC... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-416cbc87161d4f439cd1f72049cd3191 | CC(C)(C)OC(=O)N1CCNCC1.FC(F)(F)c1ccnc(Cl)c1>>CC(C)(C)OC(=O)N1CCN(c2cc(C(F)(F)F)ccn2)CC1 | C1=CN=C(C=C1C(F)(F)F)Cl.CC(C)(C)OC(=O)N1CCNCC1>>CC(C)(C)OC(=O)N1CCN(CC1)C2=NC=CC(=C2)C(F)(F)F | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:22][CH2:23]1.Cl[c:12]1[cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20][n:21]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20][n:21]2)[CH... | CC(C)(C)OC(=O)N1CCNCC1.FC(F)(F)c1ccnc(Cl)c1 | CC(C)(C)OC(=O)N1CCN(c2cc(C(F)(F)F)ccn2)CC1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | fa523b05de53c4b0abc4cfee73617ebc93929b0985f4e85a4f5201b7c9df83f1 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:10]-[C:11]-[#7:6]-[C:7]-[C:8]-1):[#7;a:2]:[c:3] | 46.13 | [{"value": 46.13, "product": "CC(C)(C)OC(=O)N1CCN(CC1)C2=NC=CC(=C2)C(F)(F)F", "details": "", "is_desired": true}] | 105 | CELSIUS | null | null | A 250 mL round flask was charged with 2-chloro-4-(trifluoromethyl)pyridine (2.57 g, 14.16 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.881 g, 1.42 mmol), Sodium tert-butoxide (1.633 g, 16.99 mmol), tert-butyl piperazine-1-carboxylate (2.64 g, 14.16 mmol) and a mixture of toluene (25 mL) and DMF (5 mL). The... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1ccncc1 | C1C[NH]CC[NH]1.c1ccncc1 | C1C[NH]CC[NH]1.c1ccncc1 | HCl | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 105 | null | CC(C)(C)OC(=O)N1CCNCC1.FC(F)(F)c1ccnc(Cl)c1>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>CC(C)(C)OC(=O)N1CCN... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-8b2355aecdcf48e08035fb224a453205 | CC(C)(C)OC(=O)N1CCNCC1.O=S(=O)(Oc1ccc(Cl)c2cccnc12)C(F)(F)F>>CC(C)(C)OC(=O)N1CCN(c2ccc(Cl)c3cccnc23)CC1 | C1=CC2=C(C=CC(=C2N=C1)OS(=O)(=O)C(F)(F)F)Cl.CC(C)(C)OC(=O)N1CCNCC1>>CC(C)(C)OC(=O)N1CCN(CC1)C2=C3C(=C(C=C2)Cl)C=CC=N3 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:23][CH2:24]1.O=S(=O)(O[c:12]1[cH:13][cH:14][c:15]([Cl:16])[c:17]2[cH:18][cH:19][cH:20][n:21][c:22]12)C(F)(F)F>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][cH:14][c:15]([Cl:16])[c:17]3[cH:18][c... | CC(C)(C)OC(=O)N1CCNCC1.O=S(=O)(Oc1ccc(Cl)c2cccnc12)C(F)(F)F | CC(C)(C)OC(=O)N1CCN(c2ccc(Cl)c3cccnc23)CC1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | C1CCOC1 | Heteroatom Alkylation and Arylation | Alkylation of amines | fe74587a462c0e3c258cd303dd59887a8148b8ae255bfd0109e2b28450b36820 | 9a1a0c2e1b87bdf69534c723b7058cd90b31cce176c7a3bc658b2756600b117c | c1cnc2c(N3CCNCC3)cccc2c1 | F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:11]1-[C:12]-[C:13]-[#7:8]-[C:9]-[C:10]-1):[c:4](:[c:5]):[#7;a:6]:[c:7] | 24.34 | [{"value": 24.34, "product": "CC(C)(C)OC(=O)N1CCN(CC1)C2=C3C(=C(C=C2)Cl)C=CC=N3", "details": "", "is_desired": true}] | 75 | CELSIUS | null | null | A mixture of 5-chloroquinolin-8-yl trifluoromethanesulfonate (1.8 g, 5.78 mmol), Cesium carbonate (2.63 g, 8.09 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.180 g, 0.29 mmol), tert- Butyl 1-piperazinecarboxylate (1.291 g, 6.93 mmol) and Palladium(II) acetate (0.065 g, 0.29 mmol) in THF (30 mL) under a nitr... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Triflate.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1ccc2ncccc2c1 | C1C[NH]CC[NH]1.c1ccc2ncccc2c1 | C1C[NH]CC[NH]1.c1ccc2ncccc2c1 | TfOH.HO- | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].C1CCOC1 | 75 | null | CC(C)(C)OC(=O)N1CCNCC1.O=S(=O)(Oc1ccc(Cl)c2cccnc12)C(F)(F)F>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].C1CCOC1>CC(C)(C)OC(=O)N1CCN(c2ccc(Cl)c3cccnc23)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-f3666d844cbc446dba498aa63de90f9a | CC(=O)Nc1cc(N)ccc1N(C)CCCN(C)C.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>>CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)ccc1N(C)CCCN(C)C | C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl.CC(=O)NC1=C(C=CC(=C1)N)N(C)CCCN(C)C>>CC(=O)NC1=C(C=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)N(C)CCCN(C)C | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH2:8])[cH:24][cH:25][c:26]1[N:27]([CH3:28])[CH2:29][CH2:30][CH2:31][N:32]([CH3:33])[CH3:34].Cl[c:9]1[cH:10][c:11]([NH:12][CH:13]2[CH2:14][CH2:15]2)[n:16]2[n:17][cH:18][c:19]([C:20]#[N:21])[c:22]2[n:23]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([NH:8][c:9]2[cH:10][c:11](... | CC(=O)Nc1cc(N)ccc1N(C)CCCN(C)C.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12 | CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)ccc1N(C)CCCN(C)C | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 6a0a0ea430a7870620c3d4d20fcc8903f46074a0b3c6c18ae32245490105a12e | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cc(NC3CC3)n3nccc3n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:2:[c:8](-[#7:9]):[c:10]:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#7:9]-[c:8]1:[c:10]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[#7;a:2]:[c:3]2:[c:4]:[c:5]:[#7;a:6]:[#7;a:7]:1:2 | 29 | [{"value": 29.0, "product": "CC(=O)NC1=C(C=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)N(C)CCCN(C)C", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | In a 40mL vial (t=g) was 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (70mg, 0.30 mmol), N-(5-amino-2-((3-(dimethylamino)propyl)(methyl)amino)phenyl)acetamide (79 mg, 0.30 mmol), and cesium carbonate (195 mg, 0.60 mmol) in DMA (0.5 mL) (),Pd2(dba)3 (13.72 mg, 0.01 mmol) and (9,9-dimethyl-9H-xan... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2ccnn2c1 | c1cnc2ccnn2c1 | c1ccccc1.C1CC1.c1cnc2ccnn2c1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC(=O)N(C)C | 150 | null | CC(=O)Nc1cc(N)ccc1N(C)CCCN(C)C.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC(=O)N(C)C>CC(=O... |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-89aff4b1c18042e4bbb1f88ebba96f86 | CCCCCCCCOc1ccc(C(=O)O)cc1.O=S(Cl)Cl>>CCCCCCCCOc1ccc(C(=O)Cl)cc1 | S(=O)(Cl)Cl.C(CCCCCCC)OC1=CC=C(C(=O)O)C=C1.C(CCCCCCC)OC1=CC=C(C(=O)O)C=C1>>C(CCCCCCC)OC1=CC=C(C(=O)Cl)C=C1 | O[C:14]([c:13]1[cH:12][cH:11][c:10]([O:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:18][cH:17]1)=[O:15].O=S(Cl)[Cl:16]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])[Cl:16])[cH:17][cH:18]1 | CCCCCCCCOc1ccc(C(=O)O)cc1.O=S(Cl)Cl | CCCCCCCCOc1ccc(C(=O)Cl)cc1 | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccccc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | A large excess of thionyl chloride was added to 10 g of the p-octyloxybenzoic acid prepared in (1), and the mixture was refluxed for 5 hours. Excessive thionyl chloride was distilled off to give a crude end compound.
Conditions: See reaction.notes.procedure_details.
Workup: the mixture was refluxed for 5 hours; Excessi... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccccc1 | HCl | null | null | null | CCCCCCCCOc1ccc(C(=O)O)cc1.O=S(Cl)Cl>>CCCCCCCCOc1ccc(C(=O)Cl)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c218088b16c541088a933a7606f68c4c | CCCCCCCCCC(=O)Cl.O=C(O)c1ccc(O)cc1>>CCCCCCCCCC(=O)Oc1ccc(C(=O)O)cc1 | OC1=CC=C(C(=O)O)C=C1.C(CCCCCCCCC)(=O)Cl.N1=CC=CC=C1>>C(CCCCCCCCC)(=O)OC1=CC=C(C(=O)O)C=C1 | Cl[C:10]([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:11].[OH:12][c:13]1[cH:14][cH:15][c:16]([C:17](=[O:18])[OH:19])[cH:20][cH:21]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10](=[O:11])[O:12][c:13]1[cH:14][cH:15][c:16]([C:17](=[O:18])[OH:19])[cH:20][cH:21]1 | CCCCCCCCCC(=O)Cl.O=C(O)c1ccc(O)cc1 | CCCCCCCCCC(=O)Oc1ccc(C(=O)O)cc1 | null | null | O | Acylation | Schotten-Baumann to ester | 1cda078f55e64d9385e544d1067595d5e7672bbd1eff542e7a341817a2d8c4d5 | 6439fc27f97ee9ed7c11ef9b5032d9493d05f28a7bbb50d256a2d54d035fbfb2 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | 1 | DAY | 10 Grams of p-hydroxybenzoic acid and 15 g of decanoic acid chloride were stirred at room temperature, and 7.2 g of pyridine was dropwise added. After the mixture was stirred for 1 day, a reaction product was poured into water, and an organic layer was extracted with dichloromethane. The organic layer was washed with 1... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aromatic alcohol | Ester | null | null | c1ccccc1 | HCl | O | null | 24 | CCCCCCCCCC(=O)Cl.O=C(O)c1ccc(O)cc1>O>CCCCCCCCCC(=O)Oc1ccc(C(=O)O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d965967cbe69411f9fd760ac1f990dfb | CCCCCCCCCC(=O)Oc1ccc(C(=O)Cl)cc1.O=C(O)c1ccc(O)cc1>>CC(=O)Oc1ccc(C(=O)O)cc1 | OC1=CC=C(C(=O)O)C=C1.FC1=C(C(=O)O)C=CC(=C1)O.C(CCCCCCCCC)(=O)OC1=CC=C(C(=O)Cl)C=C1.OC1=CC=C(C(=O)O)C=C1>>C(C)(=O)OC1=CC=C(C(=O)O)C=C1 | CCCCCCCCCC(=O)Oc1cc[c:1]([C:2](Cl)=[O:3])cc1.[OH:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[OH:11])[cH:12][cH:13]1>>[CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[OH:11])[cH:12][cH:13]1 | CCCCCCCCCC(=O)Oc1ccc(C(=O)Cl)cc1.O=C(O)c1ccc(O)cc1 | CC(=O)Oc1ccc(C(=O)O)cc1 | null | null | null | Acylation | OtherReaction | 8d291b2714bb3db13892d8fa995e95ad4f4848b3aecf7f3d9cde4fffb759072f | 1bfcbfcc1f4d736b17b57b588aed0cf2896be14f9b320b05e5c0f0a6f56e9098 | c1ccccc1 | C-C-C-C-C-C-C-C-C-C(=O)-O-c1:c:c:[c;H0;D3;+0:1](-[C;H0;D3;+0:2](-Cl)=[O;D1;H0:3]):c:c:1.[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[CH3;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | p-Acetoxybenzoic acid was prepared in the same manner as in Example 1(2) except that the 2-fluoro-4-hydroxybenzoic acid was replaced with p-hydroxybenzoic acid. The p-hydroxybenzoic acid was chlorinated in the same manner as in the above (2), to obtain an acid chloride. 1.8 Grams of the acid chloride and 2 g of the (R)... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ester.Aromatic alcohol | Ester | c1ccccc1 | null | c1ccccc1 | HCl | null | null | null | CCCCCCCCCC(=O)Oc1ccc(C(=O)Cl)cc1.O=C(O)c1ccc(O)cc1>>CC(=O)Oc1ccc(C(=O)O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e8642ae0ecb248809067cd131fde0eed | Nc1ccc(NC(=O)c2ccc(N)cc2)cc1.S=C=Nc1ccccc1>>O=C(Nc1ccc(NC(=S)Nc2ccccc2)cc1)c1ccc(NC(=S)Nc2ccccc2)cc1 | NC1=CC=C(C(=O)NC2=CC=C(C=C2)N)C=C1.C1(=CC=CC=C1)N=C=S>>C1(=CC=CC=C1)NC(=S)NC1=CC=C(C(=O)NC2=CC=C(C=C2)NC(NC2=CC=CC=C2)=S)C=C1 | [O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([NH2:8])[cH:18][cH:19]1)[c:20]1[cH:21][cH:22][c:23]([NH2:24])[cH:34][cH:35]1.[C:9](=[S:10])=[N:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([NH:8][C:9](=[S:10])[NH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18][cH:19]1)[c:20]... | Nc1ccc(NC(=O)c2ccc(N)cc2)cc1.S=C=Nc1ccccc1 | O=C(Nc1ccc(NC(=S)Nc2ccccc2)cc1)c1ccc(NC(=S)Nc2ccccc2)cc1 | null | null | CC(=O)C | Aromatic Heterocycle Formation | OtherReaction | 4657a06de0e686005efd58d334f201a97f963b9090be78faee0e623ece0b42dc | 0637e0cdada8a138a7dcdc76ec37a67953d0823c443a113a9ec7f15ee9e61b75 | O=C(Nc1ccc(NC(=S)Nc2ccccc2)cc1)c1ccc(NC(=S)Nc2ccccc2)cc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8].[S;D1;H0:9]=[C;H0;D2;+0:10]=[N;H0;D2;+0:11]-[c:12](:[c:13]):[c:14]>>[#7:15]-[C:16](=[S;D1;H0:17])-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4].[S;D1;H0:9]=[C;H0;D3;+0:10](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 72.3 | [{"value": 72.3, "product": "C1(=CC=CC=C1)NC(=S)NC1=CC=C(C(=O)NC2=CC=C(C=C2)NC(NC2=CC=CC=C2)=S)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.3, "product": "C1(=CC=CC=C1)NC(=S)NC1=CC=C(C(=O)NC2=CC=C(C=C2)NC(NC2=CC=CC=C2)=S)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 55 | CELSIUS | 10 | MINUTE | 4,4'-Diaminobenzanilide (0.658 g, 2.5 mM) was dissolved in 20 ml of acetone, and 2 equivalents of phenylisothiocyanate (0.676 g, 5 mM) was added. The mixture was stirred at 55° C. for 10 minutes. After cooling, the reaction mixture was filtered, and washed with acetone/n-hexane to obtain 0.90 g (72.3% yield) of a color... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine.Isothiocyanate | Thiourea.Thiourea | null | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | Other | CC(=O)C | 55 | 0.166667 | Nc1ccc(NC(=O)c2ccc(N)cc2)cc1.S=C=Nc1ccccc1>CC(=O)C>O=C(Nc1ccc(NC(=S)Nc2ccccc2)cc1)c1ccc(NC(=S)Nc2ccccc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-83e2d9b7b08846c09e3e4e23f2dc9784 | Nc1ccc(NC(=O)c2ccc(N)cc2)cc1.S=C=NCc1ccccc1>>O=C(Nc1ccc(NC(=S)NCc2ccccc2)cc1)c1ccc(NC(=S)NCc2ccccc2)cc1 | NC1=CC=C(C(=O)NC2=CC=C(C=C2)N)C=C1.C(C1=CC=CC=C1)N=C=S>>C(C1=CC=CC=C1)NC(=S)NC1=CC=C(C(=O)NC2=CC=C(C=C2)NC(NCC2=CC=CC=C2)=S)C=C1 | [O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([NH2:8])[cH:19][cH:12]1)[c:21]1[cH:22][cH:23][c:24]([NH2:25])[cH:36][cH:37]1.[C:9](=[S:10])=[N:28][CH2:29][c:30]1[cH:31][cH:32][cH:33][cH:34][cH:35]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([NH:8][C:9](=[S:10])[NH:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19... | Nc1ccc(NC(=O)c2ccc(N)cc2)cc1.S=C=NCc1ccccc1 | O=C(Nc1ccc(NC(=S)NCc2ccccc2)cc1)c1ccc(NC(=S)NCc2ccccc2)cc1 | null | null | CC(=O)C | Aromatic Heterocycle Formation | OtherReaction | 92e30fdf20f957cf0aab5d28c6df929c58c27e29a4f2704fb3651f4eef461e1d | 0637e0cdada8a138a7dcdc76ec37a67953d0823c443a113a9ec7f15ee9e61b75 | O=C(Nc1ccc(NC(=S)NCc2ccccc2)cc1)c1ccc(NC(=S)NCc2ccccc2)cc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[c:6]1:[c:7]:[c:8]:[c;H0;D3;+0:9](-[#7:10]-[C:11](=[O;D1;H0:12])-[c:13]):[cH;D2;+0:14]:[cH;D2;+0:15]:1.[S;D1;H0:16]=[C;H0;D2;+0:17]=[N;H0;D2;+0:18]-[C:19]-[c:20]>>[O;D1;H0:12]=[C:11](-[c:13])-[#7:10]-[c;H0;D3;+0:9]1:[c:21]:[cH;D2;+0:15]:[c:6](-[NH;D2;+0:5]-[C;H0;D3;+0:17]... | 43.4 | [{"value": 43.4, "product": "C(C1=CC=CC=C1)NC(=S)NC1=CC=C(C(=O)NC2=CC=C(C=C2)NC(NCC2=CC=CC=C2)=S)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.4, "product": "C(C1=CC=CC=C1)NC(=S)NC1=CC=C(C(=O)NC2=CC=C(C=C2)NC(NCC2=CC=CC=C2)=S)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 55 | CELSIUS | 10 | MINUTE | 4,4'-Diaminobenzanilide (0.568 g, 2.5 mM) was dissolved in 20 ml of acetone, and 2 equivalents of benzylisothiocyanate (0.746 g, 5 mM) was added. The mixture was stirred at 55° C. for 10 minutes. After cooling, the reaction mixture was filtered, and washed with acetone/n-hexane to obtain 0.57 g (43.4% yield) of a color... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine.Isothiocyanate | Thiourea.Thiourea | c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | Other | CC(=O)C | 55 | 0.166667 | Nc1ccc(NC(=O)c2ccc(N)cc2)cc1.S=C=NCc1ccccc1>CC(=O)C>O=C(Nc1ccc(NC(=S)NCc2ccccc2)cc1)c1ccc(NC(=S)NCc2ccccc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-96af32b871984951b1483d8522037b06 | Nc1ccc(N)cc1.S=C=NCc1ccccc1>>S=C(NCc1ccccc1)Nc1ccc(NC(=S)NCc2ccccc2)cc1 | C1=CC(=CC=C1N)N.C(C1=CC=CC=C1)N=C=S>>C(C1=CC=CC=C1)NC(=S)NC1=CC=C(C=C1)NC(NCC1=CC=CC=C1)=S | [NH2:3][c:4]1[cH:7][cH:6][c:5]([NH2:11])[cH:10][cH:9]1.[S:1]=[C:2]=[N:19][CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>>[S:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[NH:11][c:12]1[cH:13][cH:14][c:15]([NH:16][C:17](=[S:18])[NH:19][CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[cH:27][cH:28]... | Nc1ccc(N)cc1.S=C=NCc1ccccc1 | S=C(NCc1ccccc1)Nc1ccc(NC(=S)NCc2ccccc2)cc1 | null | null | C(C)(=O)OCC | Aromatic Heterocycle Formation | OtherReaction | 92e30fdf20f957cf0aab5d28c6df929c58c27e29a4f2704fb3651f4eef461e1d | 0637e0cdada8a138a7dcdc76ec37a67953d0823c443a113a9ec7f15ee9e61b75 | S=C(NCc1ccccc1)Nc1ccc(NC(=S)NCc2ccccc2)cc1 | [NH2;D1;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[NH2;D1;+0:6]):[cH;D2;+0:7]:[c:8]:1.[S;D1;H0:9]=[C;H0;D2;+0:10]=[N;H0;D2;+0:11]-[C:12]-[c:13]>>[#7:14]-[C:15](=[S;D1;H0:16])-[NH;D2;+0:11]-[C:12]-[c:13].[S;D1;H0:9]=[C;H0;D3;+0:10](-[NH;D2;+0:1]-[c:17](:[c:18]):[c:19])-[NH;D2;+0:6]-[CH2;D2;+0:5]-[c;H0;D3;... | 61.6 | [{"value": 61.6, "product": "C(C1=CC=CC=C1)NC(=S)NC1=CC=C(C=C1)NC(NCC1=CC=CC=C1)=S", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.6, "product": "C(C1=CC=CC=C1)NC(=S)NC1=CC=C(C=C1)NC(NCC1=CC=CC=C1)=S", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 30 | MINUTE | p-Phenylenediamine (2.707 g, 25 mM) was dissolved in 20 ml of ethyl acetate, and 2 equivalents of benzylisothiocyanate (7.461 g, 50 mM) were added. The mixture was stirred at 80° C. for 30 minutes. After cooling, the reaction mixture was filtered, and washed with ethylacetate/n-hexane to obtain 6.26 g (61.6% yield) of ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine.Isothiocyanate | Thiourea.Thiourea | c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | Other | C(C)(=O)OCC | 80 | 0.5 | Nc1ccc(N)cc1.S=C=NCc1ccccc1>C(C)(=O)OCC>S=C(NCc1ccccc1)Nc1ccc(NC(=S)NCc2ccccc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-86468e176b4c448b95c93ea7f5a809d2 | Cc1cc(N)c(C)cc1N.O=C(N=C=S)c1ccccc1>>Cc1cc(NC(=S)NC(=O)c2ccccc2)c(C)cc1NC(=S)NC(=O)c1ccccc1 | CC1=C(C=C(C(=C1)N)C)N.C(C1=CC=CC=C1)(=O)N=C=S>>C(C1=CC=CC=C1)(=O)NC(=S)NC1=C(C=C(C(=C1)C)NC(NC(C1=CC=CC=C1)=O)=S)C | [CH3:1][c:2]1[cH:3][c:4]([NH2:5])[c:17]([CH3:18])[cH:19][c:20]1[NH2:21].[C:6](=[S:7])=[N:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][C:6](=[S:7])[NH:8][C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]([CH3:18])[cH:19][c:20]1[NH:21][C:22](=[S:23])[NH:24][C:... | Cc1cc(N)c(C)cc1N.O=C(N=C=S)c1ccccc1 | Cc1cc(NC(=S)NC(=O)c2ccccc2)c(C)cc1NC(=S)NC(=O)c1ccccc1 | null | null | C(C)(=O)OCC | Aromatic Heterocycle Formation | OtherReaction | 1556984abd9ba72e5a38a8abdee2fed857645267712dcc863406dc3bc834f951 | 1fa7f9c43773782a510e141cd673852c7e5eb3c12a184196d607595aaeadd64d | O=C(NC(=S)Nc1ccc(NC(=S)NC(=O)c2ccccc2)cc1)c1ccccc1 | [NH2;D1;+0:1]-[c:2]1:[c:3]:[c:4]:[c:5](-[NH2;D1;+0:6]):[c:7]:[c:8]:1.[O;D1;H0:9]=[C:10](-[c:11])-[N;H0;D2;+0:12]=[C;H0;D2;+0:13]=[S;D1;H0:14]>>[#7:15]-[C:16](=[S;D1;H0:17])-[NH;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[c:5](-[NH;D2;+0:6]-[C;H0;D3;+0:13](=[S;D1;H0:14])-[NH;D2;+0:12]-[C:10](=[O;D1;H0:9])-[c:11]):[c:7]:[c:8]:1 | 98.7 | [{"value": 98.6, "product": "C(C1=CC=CC=C1)(=O)NC(=S)NC1=C(C=C(C(=C1)C)NC(NC(C1=CC=CC=C1)=O)=S)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.7, "product": "C(C1=CC=CC=C1)(=O)NC(=S)NC1=C(C=C(C(=C1)C)NC(NC(C1=CC=CC=C1)=O)=S)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | 2,5-Dimethyl-p-phenylenediamine (0.340 g, 2.5 mM) was dissolved in 30 ml of ethyl acetate, and 2 equivalents of benzoylisothiocyanate (0.816 g, 5 mM) were added. The mixture was stirred at room temperature for 10 minutes. After cooling, the reaction mixture was filtered, and washed with ethyl acetate/n-hexane to obtain... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine.Isothiocyanate | Thiourea.Thiourea.Secondary amide.Secondary amide | null | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | Other | C(C)(=O)OCC | null | 0.166667 | Cc1cc(N)c(C)cc1N.O=C(N=C=S)c1ccccc1>C(C)(=O)OCC>Cc1cc(NC(=S)NC(=O)c2ccccc2)c(C)cc1NC(=S)NC(=O)c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d421bcbbd72f4cb18c2bcf8464545117 | Nc1cccc2c(N)cccc12.S=C=NCc1ccccc1>>S=C(NCc1ccccc1)Nc1cccc2c(NC(=S)NCc3ccccc3)cccc12 | C1(=CC=CC=2C(=CC=CC12)N)N.C(C1=CC=CC=C1)N=C=S>>C(C1=CC=CC=C1)NC(=S)NC1=CC=CC2=C(C=CC=C12)NC(NCC1=CC=CC=C1)=S | [NH2:3][c:4]1[cH:5][cH:30][cH:31][c:32]2[c:12]([NH2:11])[cH:13][cH:14][cH:15][c:16]12.[S:1]=[C:2]=[N:21][CH2:22][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1>>[S:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[NH:11][c:12]1[cH:13][cH:14][cH:15][c:16]2[c:17]([NH:18][C:19](=[S:20])[NH:21][CH2:22][c:23]3[cH:24... | Nc1cccc2c(N)cccc12.S=C=NCc1ccccc1 | S=C(NCc1ccccc1)Nc1cccc2c(NC(=S)NCc3ccccc3)cccc12 | null | null | C(C)(=O)OCC | Aromatic Heterocycle Formation | OtherReaction | 9254ca2572e7e45f3acfa83a580f1316a326c4e88bf0371351edea9e05242b8c | 0637e0cdada8a138a7dcdc76ec37a67953d0823c443a113a9ec7f15ee9e61b75 | S=C(NCc1ccccc1)Nc1cccc2c(NC(=S)NCc3ccccc3)cccc12 | [NH2;D1;+0:1]-[c:2]1:[c:3]:[c:4]:[c:5]:[c;H0;D3;+0:6]2:[c:7]:1:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:[c;H0;D3;+0:11]:2-[NH2;D1;+0:12].[S;D1;H0:13]=[C;H0;D2;+0:14]=[N;H0;D2;+0:15]-[C:16]-[c:17]>>[S;D1;H0:13]=[C;H0;D3;+0:14](-[NH;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[c:5]:[c;H0;D3;+0:6]2:[c:18](-[#7:19]-[C:20](=[S;D1;H0:21])-[NH;D2;+0... | 30.7 | [{"value": 30.7, "product": "C(C1=CC=CC=C1)NC(=S)NC1=CC=CC2=C(C=CC=C12)NC(NCC1=CC=CC=C1)=S", "details": "PERCENTYIELD", "is_desired": false}, {"value": 30.7, "product": "C(C1=CC=CC=C1)NC(=S)NC1=CC=CC2=C(C=CC=C12)NC(NCC1=CC=CC=C1)=S", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 30 | MINUTE | 1,5-Naphthalenediamine (0.791 g, 5 mM) was dissolved in 20 ml of ethyl acetate, and 2 equivalents of benzylisothiocyanate (1.492 g, 10 mM) were added. The mixture was stirred at 80° C. for 30 minutes. After cooling, the reaction mixture was filtered, and washed with ethylacetate/n-hexane to obtain 0.70 g (30.7% yield) ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine.Isothiocyanate | Thiourea.Thiourea | c1ccc2ccccc2c1 | c1ccccc1.c1ccc2ccccc2c1 | c1ccccc1.c1ccccc1.c1ccc2ccccc2c1 | Other | C(C)(=O)OCC | 80 | 0.5 | Nc1cccc2c(N)cccc12.S=C=NCc1ccccc1>C(C)(=O)OCC>S=C(NCc1ccccc1)Nc1cccc2c(NC(=S)NCc3ccccc3)cccc12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-178874a666824f65bd0ae92352c272a1 | O.O.OCC(O)CO>>OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)CO | OCC(O)CO.O.O>>OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO | [OH2:10].[OH2:6].[OH:1][CH2:2][CH:3]([OH:4])[CH2:7][OH:8]>>[OH:1][CH2:2][C@@H:3]([OH:4])[C@@H:5]([OH:6])[C@H:7]([OH:8])[C@@H:9]([OH:10])[CH2:11][OH:12] | O.O.OCC(O)CO | OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)CO | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | af9f976e0287eeebacaff9a038b93bbe86b430b5b6b2c801dc7ee3555121fb54 | c175b3a9e7b216547982ba07a5de78fbebd36e9f37c0d8442094cf68814acb5d | null | [O;D1;H1:1]-[C:2]-[CH;D3;+0:3](-[O;D1;H1:4])-[CH2;D2;+0:5]-[O;D1;H1:6].[OH2;D0;+0:7].[OH2;D0;+0:8]>>[C:9]-[C:10](-[OH;D1;+0:7])-[C@@H;D3;+0:5](-[O;D1;H1:6])-[C:11](-[OH;D1;+0:8])-[C@H;D3;+0:3](-[O;D1;H1:4])-[C:2]-[O;D1;H1:1] | null | [] | null | null | null | null | A gel vehicle containing about 25-28% water (apart from water provided as humectant solvent), about 10-12% of 99.5% glycerine solution and about 30-35% of 70% sorbitol solution can readily provide a refractive index of about 1.43 to 1.46 and permit formation of a clear gel dentifrice in which the refractive index of th... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Secondary alcohol | Primary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol | null | null | null | Other | null | null | null | O.O.OCC(O)CO>>OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)CO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c078782347f44c58bb85cd3aadab3128 | CO.O=C(O)c1cc(Cl)ccc1O>>COC(=O)c1cc(Cl)ccc1O | ClC1=CC=C(C(C(=O)O)=C1)O.S(O)(O)(=O)=O.CO>>ClC1=CC=C(C(C(=O)OC)=C1)O | [CH3:1][OH:2].O[C:3](=[O:4])[c:5]1[cH:6][c:7]([Cl:8])[cH:9][cH:10][c:11]1[OH:12]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Cl:8])[cH:9][cH:10][c:11]1[OH:12] | CO.O=C(O)c1cc(Cl)ccc1O | COC(=O)c1cc(Cl)ccc1O | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[OH;D1;+0:7]>>[C;D1;H3:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | 5-Chlorosalicylic acid was treated with one equivalent of 18M sulfuric acid in refluxing methanol for 20 h to give methyl 5-chlorosalicylate. After recrystallization from isopropyl ether the salicylate was treated with the sodium salt of N-chloro-p-toluylsulfonamide in dimethylformamide in the presence of an excess of ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1 | HO- | null | null | null | CO.O=C(O)c1cc(Cl)ccc1O>>COC(=O)c1cc(Cl)ccc1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e00a6267a6b742de87d3f8d8a6c2a5b7 | CC(C)=O.O=C([O-])CC(O)(CC(=O)[O-])C(=O)[O-]>>CC(C)=O.CO.O=C([O-])CC(O)(CC(=O)[O-])C(=O)[O-] | C(CC(O)(C(=O)[O-])CC(=O)[O-])(=O)[O-].CC(=O)C>>C(CC(O)(C(=O)[O-])CC(=O)[O-])(=O)[O-].CC(=O)C.CO | [CH3:1][C:2](=[O:4])[CH3:5].[O:6]=[C:8]([O-:9])[CH2:10][C:11]([OH:12])([CH2:13][C:14](=[O:15])[O-:16])[C:17](=[O:18])[O-:19]>>[CH3:1][C:2]([CH3:3])=[O:4].[CH3:5][OH:6].[O:7]=[C:8]([O-:9])[CH2:10][C:11]([OH:12])([CH2:13][C:14](=[O:15])[O-:16])[C:17](=[O:18])[O-:19] | CC(C)=O.O=C([O-])CC(O)(CC(=O)[O-])C(=O)[O-] | CC(C)=O.CO.O=C([O-])CC(O)(CC(=O)[O-])C(=O)[O-] | null | null | CO | Functional Group Addition | OtherReaction | 733abf7cda91f62c92d9337e4e44c10f136d738c0c99b9d91ee60be8b40aa640 | 6bfe6b99b543f13fdcb0625ef955e43d7516e1b7bdca4c733671900e8711c2f2 | null | [C;D1;H3:1]-[C;H0;D3;+0:2](-[CH3;D1;+0:3])=[O;D1;H0:4].[O;-;D1;H0:5]-[C:6](=[O;D1;H0:7])-[C:8]-[C:9]-[C;H0;D3;+0:10](-[O;-;D1;H0:11])=[O;H0;D1;+0:12]>>[C;D1;H3:1]-[C;H0;D3;+0:2](-[C;D1;H3:13])=[O;D1;H0:4].[CH3;D1;+0:3]-[OH;D1;+0:12].[O;-;D1;H0:5]-[C:6](=[O;D1;H0:7])-[C:8]-[C:9]-[C;H0;D3;+0:10](-[O;-;D1;H0:11])=[O;D1;H0... | null | [] | null | null | null | null | Add 18 ml Citrate solution, 27 ml Acetone, and 5 ml absolute methanol.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ketone.Methanol | null | null | null | Other | CO | null | null | CC(C)=O.O=C([O-])CC(O)(CC(=O)[O-])C(=O)[O-]>CO>CC(C)=O.CO.O=C([O-])CC(O)(CC(=O)[O-])C(=O)[O-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e1ac06e7bdc449a283a63a6a8683ed03 | CC(C)=O.O=C([O-])CC(O)(CC(=O)[O-])C(=O)[O-]>>CC(C)=O.CO.O=C([O-])CC(O)(CC(=O)[O-])C(=O)[O-] | C(CC(O)(C(=O)[O-])CC(=O)[O-])(=O)[O-].CC(=O)C>>C(CC(O)(C(=O)[O-])CC(=O)[O-])(=O)[O-].CC(=O)C.CO | [CH3:1][C:2](=[O:4])[CH3:5].[O:6]=[C:8]([O-:9])[CH2:10][C:11]([OH:12])([CH2:13][C:14](=[O:15])[O-:16])[C:17](=[O:18])[O-:19]>>[CH3:1][C:2]([CH3:3])=[O:4].[CH3:5][OH:6].[O:7]=[C:8]([O-:9])[CH2:10][C:11]([OH:12])([CH2:13][C:14](=[O:15])[O-:16])[C:17](=[O:18])[O-:19] | CC(C)=O.O=C([O-])CC(O)(CC(=O)[O-])C(=O)[O-] | CC(C)=O.CO.O=C([O-])CC(O)(CC(=O)[O-])C(=O)[O-] | null | null | CO | Functional Group Addition | OtherReaction | 733abf7cda91f62c92d9337e4e44c10f136d738c0c99b9d91ee60be8b40aa640 | 6bfe6b99b543f13fdcb0625ef955e43d7516e1b7bdca4c733671900e8711c2f2 | null | [C;D1;H3:1]-[C;H0;D3;+0:2](-[CH3;D1;+0:3])=[O;D1;H0:4].[O;-;D1;H0:5]-[C:6](=[O;D1;H0:7])-[C:8]-[C:9]-[C;H0;D3;+0:10](-[O;-;D1;H0:11])=[O;H0;D1;+0:12]>>[C;D1;H3:1]-[C;H0;D3;+0:2](-[C;D1;H3:13])=[O;D1;H0:4].[CH3;D1;+0:3]-[OH;D1;+0:12].[O;-;D1;H0:5]-[C:6](=[O;D1;H0:7])-[C:8]-[C:9]-[C;H0;D3;+0:10](-[O;-;D1;H0:11])=[O;D1;H0... | null | [] | null | null | null | null | Add 18 ml Citrate solution, 27 ml Acetone, and 5 ml absolute methanol.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ketone.Methanol | null | null | null | Other | CO | null | null | CC(C)=O.O=C([O-])CC(O)(CC(=O)[O-])C(=O)[O-]>CO>CC(C)=O.CO.O=C([O-])CC(O)(CC(=O)[O-])C(=O)[O-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0b3cb71fbde54da5a7c439131d7d2319 | CCNCCCOC.N#CN>>CCN(CCCOC)C(=N)N | C(C)NCCCOC.C(C)(=O)O.C(C)(=O)[O-].N#CN>>COCCCN(C(=N)N)CC | [CH3:1][CH2:2][NH:3][CH2:4][CH2:5][CH2:6][O:7][CH3:8].[C:9](#[N:10])[NH2:11]>>[CH3:1][CH2:2][N:3]([CH2:4][CH2:5][CH2:6][O:7][CH3:8])[C:9](=[NH:10])[NH2:11] | CCNCCCOC.N#CN | CCN(CCCOC)C(=N)N | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 131bc447e2a45686a827a0392fa9e1532bd854eade4de17f001468cae63a5a41 | b39fef59d38215d20d195d9087137855c50345bea6cabdfe224335a78705a12e | null | [C:1]-[C:2]-[NH;D2;+0:3]-[C:4]-[C;D1;H3:5].[N;D1;H2:6]-[C;H0;D2;+0:7]#[N;H0;D1;+0:8]>>[C:1]-[C:2]-[N;H0;D3;+0:3](-[C:4]-[C;D1;H3:5])-[C;H0;D3;+0:7](-[N;D1;H2:6])=[NH;D1;+0:8] | 50 | [{"value": 50.0, "product": "COCCCN(C(=N)N)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.0, "product": "COCCCN(C(=N)N)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | 3.00 g (25.6 mmol) of N-ethyl-3-methoxypropylamine and 1.54 g (25.6 mmol) of acetic acid were placed in a 50 ml two neck flask. While heating the flask in a 90° C. oil bath, 1.08 g (25.6 mmol) of cyanamide was added. After 12 hours of the reaction, the product was purified by a silica gel column chromatography (eluent,... | 10.6084/m9.figshare.5104873.v1 | null | Cyanamide.Secondary amine | Tertiary amine | null | null | null | null | null | 90 | null | CCNCCCOC.N#CN>>CCN(CCCOC)C(=N)N |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b22e751eea1540b88d656fbdc64a0e99 | COCCOCCN.N#CN>>COCCOCCNC(=N)N | COCCOCCN.C(C)(=O)O.C(C)(=O)[O-].N#CN>>COCCOCCNC(=N)N | [CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][NH2:8].[C:9](#[N:10])[NH2:11]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][NH:8][C:9](=[NH:10])[NH2:11] | COCCOCCN.N#CN | COCCOCCNC(=N)N | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | a0cbddf5d7d81fe92104447f1edef14329807abeadc66f8268b3c04bddc38ea2 | 9b168a0be416143e92b99e2902110a4569d3f9f31721e83b72aa42867628c64d | null | [C:1]-[C:2]-[NH2;D1;+0:3].[N;D1;H2:4]-[C;H0;D2;+0:5]#[N;H0;D1;+0:6]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:5](-[N;D1;H2:4])=[NH;D1;+0:6] | 28.5 | [{"value": 28.5, "product": "COCCOCCNC(=N)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 28.4, "product": "COCCOCCNC(=N)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | 5.96 g (50.0 mmol) of 2-(2-methoxyethoxy)ethylamine and 3.00 g (50.0 mmol) of acetic acid were placed in a 30 ml two neck flask. While heating the flask in a 90° C. oil bath, 3.10 g (73.7 mmol) of cyanamide was added. After 5 hours of the reaction, the product was purified by a silica gel column chromatography (eluent,... | 10.6084/m9.figshare.5104873.v1 | null | Cyanamide.Primary amine | Secondary amine | null | null | null | null | null | 90 | null | COCCOCCN.N#CN>>COCCOCCNC(=N)N |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-64d5f5dd2f664288acccc0452c5aa2a9 | N#CN.NCCOCCOC(=O)c1ccccc1>>N=C(N)NCCOCCOC(=O)c1ccccc1 | C(C1=CC=CC=C1)(=O)OCCOCCN.C(C)(=O)O.C(C)(=O)[O-].N#CN>>C(C1=CC=CC=C1)(=O)OCCOCCNC(=N)N | [N:1]#[C:2][NH2:3].[NH2:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][C:11](=[O:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[NH:1]=[C:2]([NH2:3])[NH:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][C:11](=[O:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | N#CN.NCCOCCOC(=O)c1ccccc1 | N=C(N)NCCOCCOC(=O)c1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | a0cbddf5d7d81fe92104447f1edef14329807abeadc66f8268b3c04bddc38ea2 | 9b168a0be416143e92b99e2902110a4569d3f9f31721e83b72aa42867628c64d | c1ccccc1 | [C:1]-[C:2]-[NH2;D1;+0:3].[N;D1;H2:4]-[C;H0;D2;+0:5]#[N;H0;D1;+0:6]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:5](-[N;D1;H2:4])=[NH;D1;+0:6] | 62.1 | [{"value": 62.0, "product": "C(C1=CC=CC=C1)(=O)OCCOCCNC(=N)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.1, "product": "C(C1=CC=CC=C1)(=O)OCCOCCNC(=N)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | 2.14 g (10.2 mmol) of 2-(2-aminoethoxy)ethyl benzoate and 0.624 g (10.4 mmol) of acetic acid were placed in a 50 ml two neck flask. While heating the flask in a 90° C. oil bath, 0.680 g (16.2 mmol) of cyanamide was added. After 6 hours of the reaction, the product was purified by a silica gel column chromatography (elu... | 10.6084/m9.figshare.5104873.v1 | null | Cyanamide.Primary amine | Secondary amine | null | null | c1ccccc1 | null | null | 90 | null | N#CN.NCCOCCOC(=O)c1ccccc1>>N=C(N)NCCOCCOC(=O)c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-84fae49193d148f395e8e28f50d554ab | CC(=O)OC(C)=O.N=C(N)NCCOCCO>>CC(=O)OCCOCCNC(=N)N | C(CCC(=O)O)(=O)O.OCCOCCNC(=N)N.C(C)(=O)[O-].C(C)(=O)OC(C)=O>>C(C)(=O)OCCOCCNC(=N)N | CC(=O)O[C:2]([CH3:1])=[O:3].[OH:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][NH:10][C:11](=[NH:12])[NH2:13]>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][NH:10][C:11](=[NH:12])[NH2:13] | CC(=O)OC(C)=O.N=C(N)NCCOCCO | CC(=O)OCCOCCNC(=N)N | null | null | C(C)N(CC)CC | Acylation | Transesterification | f81e513b7b512b10157c16426844efd8d88e34c97987c1347c6ba8a688351205 | fc27d67c790d5fb520ba5d49de1490661fa5b822b714863734ce7e3029dfa84f | null | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[C:4]-[C:5]-[O;H0;D2;+0:6]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | 40 | [{"value": 40.0, "product": "C(C)(=O)OCCOCCNC(=N)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.0, "product": "C(C)(=O)OCCOCCNC(=N)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 2.06 g (9.99 mmol) of 2-(2-hydroxyethoxy)ethylguanidine succinate, 8 ml of triethylamine, 0.122 mg (1.0 mmol) of 4-N,N-dimethylaminopyridine and 1.02 g (9.99 mmol) of acetic anhydride were placed in a 50 ml two neck flask and were stirred for 1 hour at room temperature. After the upper phase was removed by decantation,... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary alcohol | Ester | null | null | null | HO- | C(C)N(CC)CC | null | 1 | CC(=O)OC(C)=O.N=C(N)NCCOCCO>C(C)N(CC)CC>CC(=O)OCCOCCNC(=N)N |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a6fad661b27341e199b0050914752841 | CCCCCC.Cc1ccccc1>>CCCCCCCCCCCC | CCCCCC.C1=CC=CC=C1.C1(=CC=CC=C1)C>>CCCCCCCCCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C[c:12]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12] | CCCCCC.Cc1ccccc1 | CCCCCCCCCCCC | null | null | CC=1C=CC(=CC1)C | C-C Coupling | OtherReaction | 504486cf480112502d548fc82ef7c94ab889e09191c23e550c9e2e0304f1ad99 | 410ec9b1cc243569e4ff568c248f0b402403802e002b4018f576af3f6960507b | null | C-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C:7]-[C:8]-[CH3;D1;+0:9]>>[C:7]-[C:8]-[CH2;D2;+0:9]-[CH2;D2;+0:6]-[CH2;D2;+0:5]-[CH2;D2;+0:4]-[CH2;D2;+0:3]-[CH2;D2;+0:2]-[CH3;D1;+0:1] | null | [] | null | null | null | null | When the dispersion of the solid polymer electrolyte was added to organic solvents having a dielectric constant of less than 3, such as n-hexane, benzene, toluene, p-xylene and dodecane having dielectric constants of 1.89, 2.28, 2.38, 2.27 and 2.02, respectively, the solid polymer electrolyte produced a white precipita... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1 | null | null | Other | CC=1C=CC(=CC1)C | null | null | CCCCCC.Cc1ccccc1>CC=1C=CC(=CC1)C>CCCCCCCCCCCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ec57be9eb3044d5884323695460dbccf | CC[C@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)OCc1ccccc1)C(Cc1ccccc1)C(=O)O)[C@H](C)OCc1ccccc1)c1ccccc1>>CC[C@H](NC(=O)[C@H](NC(=O)[C@@H](N)CC(=O)O)[C@H](C)O)c1ccccc1 | C(C)[C@@H](C1=CC=CC=C1)NC([C@H](NC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C(O)=O)CC1=CC=CC=C1)=O)[C@@H](OCC1=CC=CC=C1)C)=O.C(C)(=O)O>>C(C)[C@@H](C1=CC=CC=C1)NC([C@H](NC([C@@H](N)CC(O)=O)=O)[C@@H](O)C)=O | O=C(OCc1ccccc1)[NH:12][C@H:11]([C:9]([NH:8][C@@H:7]([C:5]([NH:4][C@@H:3]([CH2:2][CH3:1])[c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1)=[O:6])[C@H:17]([CH3:18])[O:19]Cc1ccccc1)=[O:10])[CH:13](Cc1ccccc1)[C:14](=[O:15])[OH:16]>>[CH3:1][CH2:2][C@H:3]([NH:4][C:5](=[O:6])[C@H:7]([NH:8][C:9](=[O:10])[C@@H:11]([NH2:12])[CH2:13][... | CC[C@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)OCc1ccccc1)C(Cc1ccccc1)C(=O)O)[C@H](C)OCc1ccccc1)c1ccccc1 | CC[C@H](NC(=O)[C@H](NC(=O)[C@@H](N)CC(=O)O)[C@H](C)O)c1ccccc1 | null | [Pd].[C] | CO | Reduction | OtherReaction | 6440dad6ad55ca27c536b1a74b3a7df218bda98f17e8c82abfba270822c80d3d | 5d564b4d4eafa0dce2e347226de4767a41ecdc3d26cc0a9dc4ac1ef93c08f88d | c1ccccc1 | O=C(-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:1]-[C:2](-[C:3](=[O;D1;H0:4])-[#7:5]-[C:6](-[C:7](-[C;D1;H3:8])-[O;H0;D2;+0:9]-C-c1:c:c:c:c:c:1)-[C:10](-[#7:11])=[O;D1;H0:12])-[CH;D3;+0:13](-C-c1:c:c:c:c:c:1)-[C:14](=[O;D1;H0:15])-[O;D1;H1:16]>>[#7:11]-[C:10](=[O;D1;H0:12])-[C:6](-[#7:5]-[C:3](=[O;D1;H0:4])-[C:2](-[NH2;D1;+0:1])-[C... | 57.5 | [{"value": 57.5, "product": "C(C)[C@@H](C1=CC=CC=C1)NC([C@H](NC([C@@H](N)CC(O)=O)=O)[C@@H](O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 5.30 g (8.0 mmols) of N-benzyloxycarbonyl-β-benzyl-L-aspartyl-O-benzyl-D-threonine (S)-α-ethylbenzylamide in 150 ml of methanol were added 1.0 ml of acetic acid and 3.0 g of 5% Pd-carbon (water content 50%), and the mixture was reduced under hydrogen overnight at room temperature and then at 50° C. for... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether | Secondary alcohol.Primary amine | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccccc1 | HO- | [Pd].[C].CO | null | 8 | CC[C@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)OCc1ccccc1)C(Cc1ccccc1)C(=O)O)[C@H](C)OCc1ccccc1)c1ccccc1>[Pd].[C].CO>CC[C@H](NC(=O)[C@H](NC(=O)[C@@H](N)CC(=O)O)[C@H](C)O)c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a473542e2c91474d920bd8a0505e632c | CC[C@@H](C)[C@@H](NC(=O)[C@@H](NC(=O)OCc1ccccc1)C(Cc1ccccc1)C(=O)O)C(=O)O.CC[C@H](N)c1ccccc1>>CC[C@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)OCc1ccccc1)C(Cc1ccccc1)C(=O)O)[C@H](C)CC)c1ccccc1 | C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C(O)=O)CC1=CC=CC=C1)C(=O)N[C@H]([C@H](C)CC)C(=O)O.C(C)[C@@H](C1=CC=CC=C1)N.O.C=1C=CC2=C(C1)N=NN2O>>C(C)[C@@H](C1=CC=CC=C1)NC([C@H](NC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C(O)=O)CC1=CC=CC=C1)=O)[C@H](C)CC)=O | O[C:5](=[O:6])[C@H:7]([NH:8][C:9](=[O:10])[C@@H:11]([NH:12][C:13](=[O:14])[O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[CH:23]([CH2:24][c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1)[C:31](=[O:32])[OH:33])[C@H:34]([CH3:35])[CH2:36][CH3:37].[CH3:1][CH2:2][C@H:3]([NH2:4])[c:38]1[cH:39][cH:40][cH:41][cH:42][cH:4... | CC[C@@H](C)[C@@H](NC(=O)[C@@H](NC(=O)OCc1ccccc1)C(Cc1ccccc1)C(=O)O)C(=O)O.CC[C@H](N)c1ccccc1 | CC[C@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)OCc1ccccc1)C(Cc1ccccc1)C(=O)O)[C@H](C)CC)c1ccccc1 | null | null | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CNC(=O)[C@H](CCc1ccccc1)NC(=O)OCc1ccccc1)NCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7].[C:8]-[C:9](-[NH2;D1;+0:10])-[c:11]>>[C:8]-[C:9](-[c:11])-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7] | 33.1 | [{"value": 33.1, "product": "C(C)[C@@H](C1=CC=CC=C1)NC([C@H](NC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C(O)=O)CC1=CC=CC=C1)=O)[C@H](C)CC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 6.69 g (14.2 mmols) of N-benzyloxycarbonyl-β-benzyl-L-aspartyl-D-isoleucine and 2.04 g (15.1 mmols) of (S)-α-ethylbenzylamine in 200 ml of methylene chloride were added 2.73 g (14.2 mmols) of water-soluble carbodiimide hydrochloride and 1.92 g (14.2 mmols) of HOBt under cooling and stirred for one hour... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl | null | 1 | CC[C@@H](C)[C@@H](NC(=O)[C@@H](NC(=O)OCc1ccccc1)C(Cc1ccccc1)C(=O)O)C(=O)O.CC[C@H](N)c1ccccc1>C(Cl)Cl>CC[C@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)OCc1ccccc1)C(Cc1ccccc1)C(=O)O)[C@H](C)CC)c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b4a1a9f06c874053b3ad0f85aaa15884 | CC[C@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)OCc1ccccc1)C(Cc1ccccc1)C(=O)O)[C@H](C)CC)c1ccccc1>>CC[C@H](NC(=O)[C@H](NC(=O)[C@@H](N)CC(=O)O)[C@H](C)CC)c1ccccc1 | C(C)[C@@H](C1=CC=CC=C1)NC([C@H](NC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C(O)=O)CC1=CC=CC=C1)=O)[C@H](C)CC)=O>>C(C)[C@@H](C1=CC=CC=C1)NC([C@H](NC([C@@H](N)CC(O)=O)=O)[C@H](C)CC)=O | O=C(OCc1ccccc1)[NH:12][C@H:11]([C:9]([NH:8][C@@H:7]([C:5]([NH:4][C@@H:3]([CH2:2][CH3:1])[c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1)=[O:6])[C@H:17]([CH3:18])[CH2:19][CH3:20])=[O:10])[CH:13](Cc1ccccc1)[C:14](=[O:15])[OH:16]>>[CH3:1][CH2:2][C@H:3]([NH:4][C:5](=[O:6])[C@H:7]([NH:8][C:9](=[O:10])[C@@H:11]([NH2:12])[CH2:13]... | CC[C@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)OCc1ccccc1)C(Cc1ccccc1)C(=O)O)[C@H](C)CC)c1ccccc1 | CC[C@H](NC(=O)[C@H](NC(=O)[C@@H](N)CC(=O)O)[C@H](C)CC)c1ccccc1 | null | [Pd].[C] | CO.O | Reduction | OtherReaction | 2ae9c4180e6c8f22531653916ae16c5001520ba250f0cc322eed8d0036ef5c0b | 4e549866ec1acadec4c84aaf8495992a28ec78d8ea5ef1b9f44dd843b0dcb7d4 | c1ccccc1 | O=C(-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:1]-[C:2](-[C:3](=[O;D1;H0:4])-[#7:5]-[C:6]-[C:7](-[#7:8])=[O;D1;H0:9])-[CH;D3;+0:10](-C-c1:c:c:c:c:c:1)-[C:11](=[O;D1;H0:12])-[O;D1;H1:13]>>[#7:8]-[C:7](=[O;D1;H0:9])-[C:6]-[#7:5]-[C:3](=[O;D1;H0:4])-[C:2](-[NH2;D1;+0:1])-[CH2;D2;+0:10]-[C:11](=[O;D1;H0:12])-[O;D1;H1:13] | 72.3 | [{"value": 72.3, "product": "C(C)[C@@H](C1=CC=CC=C1)NC([C@H](NC([C@@H](N)CC(O)=O)=O)[C@H](C)CC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | To a suspension of 2.81 g (4.7 mmols) of N-benzyloxycarbonyl-β-benzyl-L-aspartyl-D-isoleucine (S)-α-ethylbenzylamide in 150 ml of methanol and 50 ml of water was added 2.0 g of 10% Pd-carbon (water content 50%). The mixture was reduced under hydrogen at room temperature for 5 hours. The catalyst was removed by filtrati... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | c1ccccc1.c1ccccc1 | null | c1ccccc1 | HO- | [Pd].[C].CO.O | null | 5 | CC[C@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)OCc1ccccc1)C(Cc1ccccc1)C(=O)O)[C@H](C)CC)c1ccccc1>[Pd].[C].CO.O>CC[C@H](NC(=O)[C@H](NC(=O)[C@@H](N)CC(=O)O)[C@H](C)CC)c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-39d7a85f6c0943d29b102f7ee592196e | CC[C@H](NC(=O)C(CC)(CC)NC(=O)OC(C)(C)C)c1ccccc1.O=C(N[C@H](C(=O)[O-])C(Cc1ccccc1)C(=O)[O-])OCc1ccccc1>>CC[C@H](NC(=O)C(CC)(CC)NC(=O)[C@@H](N)CC(=O)O)c1ccccc1 | O.C=1C=CC2=C(C1)N=NN2O.Cl.O1CCOCC1.C(C)[C@@H](C1=CC=CC=C1)NC(C(NC(=O)OC(C)(C)C)(CC)CC)=O.C(C)N(CC)CC.C(C1=CC=CC=C1)C([C@H](NC(=O)OCC1=CC=CC=C1)C(=O)[O-])C(=O)[O-]>>C(C)[C@@H](C1=CC=CC=C1)NC(C(NC([C@@H](N)CC(O)=O)=O)(CC)CC)=O | CC(C)(C)O[C:13]([NH:12][C:7]([C:5]([NH:4][C@@H:3]([CH2:2][CH3:1])[c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1)=[O:6])([CH2:8][CH3:9])[CH2:10][CH3:11])=[O:14].O=C([O-])[C@@H:15]([NH:16]C(=O)OCc1ccccc1)[CH:17](Cc1ccccc1)[C:18](=[O:19])[O-:20]>>[CH3:1][CH2:2][C@H:3]([NH:4][C:5](=[O:6])[C:7]([CH2:8][CH3:9])([CH2:10][CH3:11]... | CC[C@H](NC(=O)C(CC)(CC)NC(=O)OC(C)(C)C)c1ccccc1.O=C(N[C@H](C(=O)[O-])C(Cc1ccccc1)C(=O)[O-])OCc1ccccc1 | CC[C@H](NC(=O)C(CC)(CC)NC(=O)[C@@H](N)CC(=O)O)c1ccccc1 | null | null | null | C-C Coupling | OtherReaction | 2bea6d34df74879b5adbc15b9b68d5ec6c520d56804f794f7dd114edaa9d1e61 | adfb67fde63e0b1e1f69cfab03a62dd0c8c7aad5a4584ffa7e9af353c8701063 | c1ccccc1 | C-C(-C)(-C)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[C:4]-[C:5](-[#7:6])=[O;D1;H0:7].O=C(-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:8]-[C@H;D3;+0:9](-C(=O)-[O-])-[CH;D3;+0:10](-C-c1:c:c:c:c:c:1)-[C:11](-[O-;H0;D1:12])=[O;D1;H0:13]>>[#7:6]-[C:5](=[O;D1;H0:7])-[C:4]-[#7:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C@@H;D3;+0:9](-[NH2;D1;+0:8])-[C... | 29.3 | [{"value": 29.3, "product": "C(C)[C@@H](C1=CC=CC=C1)NC(C(NC([C@@H](N)CC(O)=O)=O)(CC)CC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 19 ml of 4N-HCl/dioxane solution were added to 1.31 g (3.76 mmols) of N-t-butoxycarbonyl-α,α-diethylglycine (S)-α-ethylbenzylamide, and the mixture was stirred at room temperature for one hour. The reaction mixture was concentrated under reduced pressure, 30 ml of ether was added to the residue, and this was again conc... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carbamic ester.Ether.Ether.Boc | Carboxylic acid.Secondary amide.Primary amine | c1ccccc1.c1ccccc1 | null | c1ccccc1 | HO- | null | null | 1 | CC[C@H](NC(=O)C(CC)(CC)NC(=O)OC(C)(C)C)c1ccccc1.O=C(N[C@H](C(=O)[O-])C(Cc1ccccc1)C(=O)[O-])OCc1ccccc1>>CC[C@H](NC(=O)C(CC)(CC)NC(=O)[C@@H](N)CC(=O)O)c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a2a351b69552484f9b0780b4d2a5b2e4 | CC[C@H](NC(=O)C(C)(CC)NC(=O)OC(C)(C)C)c1ccccc1>>CC[C@H](NC(=O)C(C)(CC)NC(=O)[C@@H](N)CC(=O)O)c1ccccc1 | Cl.O1CCOCC1.C(C)[C@@H](C1=CC=CC=C1)NC(C(NC(=O)OC(C)(C)C)(CC)C)=O.O.C(C)N(CC)CC>>C(C)[C@@H](C1=CC=CC=C1)NC(C(NC([C@@H](N)CC(O)=O)=O)(CC)C)=O | C[C:17](C)([CH3:16])[O:19][C:12]([NH:11][C:7]([C:5]([NH:4][C@@H:3]([CH2:2][CH3:1])[c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1)=[O:6])([CH3:8])[CH2:9][CH3:10])=[O:13]>>[CH3:1][CH2:2][C@H:3]([NH:4][C:5](=[O:6])[C:7]([CH3:8])([CH2:9][CH3:10])[NH:11][C:12](=[O:13])[C@@H:14]([NH2:15])[CH2:16][C:17](=[O:18])[OH:19])[c:20]1[c... | CC[C@H](NC(=O)C(C)(CC)NC(=O)OC(C)(C)C)c1ccccc1 | CC[C@H](NC(=O)C(C)(CC)NC(=O)[C@@H](N)CC(=O)O)c1ccccc1 | null | null | null | Functional Group Addition | OtherReaction | 105198afbc51ea3f60e76c995d03c882ac1f8f453751246db696160faebdac1f | 6216e62ee4606269ad256ad9420ad311b1674fee19876e3be7c90df244104ff1 | c1ccccc1 | C-[C;H0;D4;+0:1](-C)(-[CH3;D1;+0:2])-[O;H0;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[#7:6]-[C:7]-[C:8](-[#7:9])=[O;D1;H0:10]>>[#7:9]-[C:8](=[O;D1;H0:10])-[C:7]-[#7:6]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[C:11](-[N;D1;H2:12])-[CH2;D2;+0:2]-[C;H0;D3;+0:1](=[O;D1;H0:13])-[OH;D1;+0:3] | null | [] | null | null | 1 | HOUR | 10 ml of 4N-HCl/dioxane solution was added to 0.66 (1.97 mmols) of N-t-butoxycarbonyl-DL-isovaline (S)-α-ethylbenzylamide, and the mixture was stirred at room temperature for one hour. The reaction mixture was concentrated under reduced pressure, 30 ml of ether were added to the residue, and this was again concentrated... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Carboxylic acid.Secondary amide.Primary amine | null | null | c1ccccc1 | Other | null | null | 1 | CC[C@H](NC(=O)C(C)(CC)NC(=O)OC(C)(C)C)c1ccccc1>>CC[C@H](NC(=O)C(C)(CC)NC(=O)[C@@H](N)CC(=O)O)c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3d062dc2d8ab4e1391656e4f536498a8 | COC[C@H](NC(=O)OC(C)(C)C)c1ccccc1>>COC[C@H](N)c1ccccc1 | Cl.O1CCOCC1.C(C)(C)(C)OC(=O)N[C@H](C1=CC=CC=C1)COC>>Cl.COC[C@@H](C1=CC=CC=C1)N | CC(C)(C)OC(=O)[NH:5][C@@H:4]([CH2:3][O:2][CH3:1])[c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[CH3:1][O:2][CH2:3][C@H:4]([NH2:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1 | COC[C@H](NC(=O)OC(C)(C)C)c1ccccc1 | COC[C@H](N)c1ccccc1 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[c:4]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[c:4] | null | [] | null | null | 1 | HOUR | 60 ml of 4N-HCl/dioxane solution was added to 4.02 g (16.0 mmols) of N-t-butoxycarbonyl-(R)-α-methoxymethylbenzylamine, and the mixture was stirred at room temperature for one hour. The reaction mixture was concentrated under reduced pressure. 30 ml of ether were added to the residue, and this was further concentrated ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1 | HO- | null | null | 1 | COC[C@H](NC(=O)OC(C)(C)C)c1ccccc1>>COC[C@H](N)c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1b033c485fa54b2cb55a6e97a581a99c | COC[C@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)OCc1ccccc1)C(Cc1ccccc1)C(=O)O)C(C)C)c1ccccc1>>COC[C@H](NC(=O)[C@H](NC(=O)[C@@H](N)CC(=O)O)C(C)C)c1ccccc1 | COC[C@@H](C1=CC=CC=C1)NC([C@H](NC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C(O)=O)CC1=CC=CC=C1)=O)C(C)C)=O>>COC[C@@H](C1=CC=CC=C1)NC([C@H](NC([C@@H](N)CC(O)=O)=O)C(C)C)=O | O=C(OCc1ccccc1)[NH:13][C@H:12]([C:10]([NH:9][C@@H:8]([C:6]([NH:5][C@@H:4]([CH2:3][O:2][CH3:1])[c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1)=[O:7])[CH:18]([CH3:19])[CH3:20])=[O:11])[CH:14](Cc1ccccc1)[C:15](=[O:16])[OH:17]>>[CH3:1][O:2][CH2:3][C@H:4]([NH:5][C:6](=[O:7])[C@H:8]([NH:9][C:10](=[O:11])[C@@H:12]([NH2:13])[CH2:... | COC[C@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)OCc1ccccc1)C(Cc1ccccc1)C(=O)O)C(C)C)c1ccccc1 | COC[C@H](NC(=O)[C@H](NC(=O)[C@@H](N)CC(=O)O)C(C)C)c1ccccc1 | null | [Pd].[C] | CO.O | Reduction | OtherReaction | 2ae9c4180e6c8f22531653916ae16c5001520ba250f0cc322eed8d0036ef5c0b | 4e549866ec1acadec4c84aaf8495992a28ec78d8ea5ef1b9f44dd843b0dcb7d4 | c1ccccc1 | O=C(-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:1]-[C:2](-[C:3](=[O;D1;H0:4])-[#7:5]-[C:6]-[C:7](-[#7:8])=[O;D1;H0:9])-[CH;D3;+0:10](-C-c1:c:c:c:c:c:1)-[C:11](=[O;D1;H0:12])-[O;D1;H1:13]>>[#7:8]-[C:7](=[O;D1;H0:9])-[C:6]-[#7:5]-[C:3](=[O;D1;H0:4])-[C:2](-[NH2;D1;+0:1])-[CH2;D2;+0:10]-[C:11](=[O;D1;H0:12])-[O;D1;H1:13] | 70.1 | [{"value": 70.0, "product": "COC[C@@H](C1=CC=CC=C1)NC([C@H](NC([C@@H](N)CC(O)=O)=O)C(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.1, "product": "COC[C@@H](C1=CC=CC=C1)NC([C@H](NC([C@@H](N)CC(O)=O)=O)C(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | null | null | To a suspension of 6.20 g (10.5 mmols) of N-benzyloxycarbonyl-β-benzyl-L-aspartyl-D-valine (R)-α-methoxymethylbenzylamide in 200 ml of methanol and 50 ml of water was added 1.50 g of 10% Pd-carbon (water content 50%). The mixture was reduced under hydrogen under heat at 40° C. The catalyst was removed by filtration, an... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | c1ccccc1.c1ccccc1 | null | c1ccccc1 | HO- | [Pd].[C].CO.O | 40 | null | COC[C@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)OCc1ccccc1)C(Cc1ccccc1)C(=O)O)C(C)C)c1ccccc1>[Pd].[C].CO.O>COC[C@H](NC(=O)[C@H](NC(=O)[C@@H](N)CC(=O)O)C(C)C)c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ae03dc6af35144969588f144b56bba80 | CCOC[C@H](NC(=O)OC(C)(C)C)c1ccccc1>>CCOC[C@H](N)c1ccccc1 | Cl.O1CCOCC1.C(C)(C)(C)OC(=O)N[C@H](C1=CC=CC=C1)COCC>>Cl.C(C)OC[C@@H](C1=CC=CC=C1)N | CC(C)(C)OC(=O)[NH:6][C@@H:5]([CH2:4][O:3][CH2:2][CH3:1])[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[CH3:1][CH2:2][O:3][CH2:4][C@H:5]([NH2:6])[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | CCOC[C@H](NC(=O)OC(C)(C)C)c1ccccc1 | CCOC[C@H](N)c1ccccc1 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[c:4]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[c:4] | null | [] | null | null | 1 | HOUR | 12.5 ml of 4N-HCl/dioxane solution were added to 0.66 g (2.5 mmols) of N-t-butoxycarbonyl-(R)-α-ethoxymethylbenzylamine, and the mixture was stirred at room temperature for one hour. The reaction mixture was concentrated under reduced pressure, 30 ml of ether was added to the residue, and this was further concentrated ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1 | HO- | null | null | 1 | CCOC[C@H](NC(=O)OC(C)(C)C)c1ccccc1>>CCOC[C@H](N)c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-29bd294101a04d54b49813c6be393808 | CCOC[C@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)OCc1ccccc1)C(Cc1ccccc1)C(=O)O)C(C)C)c1ccccc1>>CCOC[C@H](NC(=O)[C@H](NC(=O)[C@@H](N)CC(=O)O)C(C)C)c1ccccc1 | C(C)OC[C@@H](C1=CC=CC=C1)NC([C@H](NC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C(O)=O)CC1=CC=CC=C1)=O)C(C)C)=O>>C(C)OC[C@@H](C1=CC=CC=C1)NC([C@H](NC([C@@H](N)CC(O)=O)=O)C(C)C)=O | O=C(OCc1ccccc1)[NH:14][C@H:13]([C:11]([NH:10][C@@H:9]([C:7]([NH:6][C@@H:5]([CH2:4][O:3][CH2:2][CH3:1])[c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)=[O:8])[CH:19]([CH3:20])[CH3:21])=[O:12])[CH:15](Cc1ccccc1)[C:16](=[O:17])[OH:18]>>[CH3:1][CH2:2][O:3][CH2:4][C@H:5]([NH:6][C:7](=[O:8])[C@H:9]([NH:10][C:11](=[O:12])[C@@H:13... | CCOC[C@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)OCc1ccccc1)C(Cc1ccccc1)C(=O)O)C(C)C)c1ccccc1 | CCOC[C@H](NC(=O)[C@H](NC(=O)[C@@H](N)CC(=O)O)C(C)C)c1ccccc1 | null | [Pd].[C] | CO.O | Reduction | OtherReaction | 2ae9c4180e6c8f22531653916ae16c5001520ba250f0cc322eed8d0036ef5c0b | 4e549866ec1acadec4c84aaf8495992a28ec78d8ea5ef1b9f44dd843b0dcb7d4 | c1ccccc1 | O=C(-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:1]-[C:2](-[C:3](=[O;D1;H0:4])-[#7:5]-[C:6]-[C:7](-[#7:8])=[O;D1;H0:9])-[CH;D3;+0:10](-C-c1:c:c:c:c:c:1)-[C:11](=[O;D1;H0:12])-[O;D1;H1:13]>>[#7:8]-[C:7](=[O;D1;H0:9])-[C:6]-[#7:5]-[C:3](=[O;D1;H0:4])-[C:2](-[NH2;D1;+0:1])-[CH2;D2;+0:10]-[C:11](=[O;D1;H0:12])-[O;D1;H1:13] | 50.3 | [{"value": 50.3, "product": "C(C)OC[C@@H](C1=CC=CC=C1)NC([C@H](NC([C@@H](N)CC(O)=O)=O)C(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.3, "product": "C(C)OC[C@@H](C1=CC=CC=C1)NC([C@H](NC([C@@H](N)CC(O)=O)=O)C(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | null | null | To a suspension of 1.20 g (1.99 mmols) of N-benzyloxycarbonyl-β-benzyl-L-aspartyl-D-valine (R)-α-ethoxymethylbenzylamide in 50 ml of methanol and 10 ml of water was added 0.30 g of 10% Pd-carbon (water content 50%). The mixture was reduced under hydrogen under heat at 40°C., 40 ml of water was added thereto, the cataly... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | c1ccccc1.c1ccccc1 | null | c1ccccc1 | HO- | [Pd].[C].CO.O | 40 | null | CCOC[C@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)OCc1ccccc1)C(Cc1ccccc1)C(=O)O)C(C)C)c1ccccc1>[Pd].[C].CO.O>CCOC[C@H](NC(=O)[C@H](NC(=O)[C@@H](N)CC(=O)O)C(C)C)c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f6a778234f084513ae50b4ca3b6875a0 | CC[C@@H](C)[C@@H](NC(=O)[C@@H](NC(=O)OCc1ccccc1)C(Cc1ccccc1)C(=O)O)C(=O)O.COC[C@H](N)c1ccccc1>>CC[C@@H](C)[C@@H](NC(=O)[C@@H](N)CC(=O)O)C(=O)N[C@@H](COC)c1ccccc1 | C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C(O)=O)CC1=CC=CC=C1)C(=O)N[C@H]([C@H](C)CC)C(=O)O.Cl.COC[C@@H](C1=CC=CC=C1)N>>COC[C@@H](C1=CC=CC=C1)NC([C@H](NC([C@@H](N)CC(O)=O)=O)[C@H](C)CC)=O | O=C(OCc1ccccc1)[NH:10][C@H:9]([C:7]([NH:6][C@H:5]([C@@H:3]([CH2:2][CH3:1])[CH3:4])[C:15](O)=[O:16])=[O:8])[CH:11](Cc1ccccc1)[C:12](=[O:13])[OH:14].[NH2:17][C@@H:18]([CH2:19][O:20][CH3:21])[c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>>[CH3:1][CH2:2][C@@H:3]([CH3:4])[C@@H:5]([NH:6][C:7](=[O:8])[C@@H:9]([NH2:10])[CH2:11][C... | CC[C@@H](C)[C@@H](NC(=O)[C@@H](NC(=O)OCc1ccccc1)C(Cc1ccccc1)C(=O)O)C(=O)O.COC[C@H](N)c1ccccc1 | CC[C@@H](C)[C@@H](NC(=O)[C@@H](N)CC(=O)O)C(=O)N[C@@H](COC)c1ccccc1 | null | null | null | Acylation | OtherReaction | fe1a4b0374f25b0ed4760d7d65c253df5c8960faebba6bf1475bd86a65cd06fd | 337ca72c0bb1979769aac1fc7825c6586b8e75bbb5702fd9212c320d1f1752db | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6](=[O;D1;H0:7])-[C:8](-[NH;D2;+0:9]-C(=O)-O-C-c1:c:c:c:c:c:1)-[CH;D3;+0:10](-C-c1:c:c:c:c:c:1)-[C:11](=[O;D1;H0:12])-[O;D1;H1:13].[C:14]-[C:15](-[NH2;D1;+0:16])-[c:17]>>[C:14]-[C:15](-[c:17])-[NH;D2;+0:16]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6](=[... | 22.1 | [{"value": 22.1, "product": "COC[C@@H](C1=CC=CC=C1)NC([C@H](NC([C@@H](N)CC(O)=O)=O)[C@H](C)CC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The same process as in Example 15 was repeated, except that N-benzyloxycarbonyl-β-benzyl-L-aspartyl-D-isoleucine was used in place of N-benzyloxycarbonyl-β-benzyl-L-aspartyl-D-valine and that (R)-α-methoxymethylbenzylamine hydrochloride was used in place of (R)-α-ethoxymethylbenzylamine hydrochloride, and α-L-aspartyl-... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Primary amine | Secondary amide.Primary amine | c1ccccc1.c1ccccc1 | null | c1ccccc1 | HO- | null | null | null | CC[C@@H](C)[C@@H](NC(=O)[C@@H](NC(=O)OCc1ccccc1)C(Cc1ccccc1)C(=O)O)C(=O)O.COC[C@H](N)c1ccccc1>>CC[C@@H](C)[C@@H](NC(=O)[C@@H](N)CC(=O)O)C(=O)N[C@@H](COC)c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-12a035e31d384b0d952ee7e106393c5e | COC[C@H](N)c1ccccc1.C[C@@H](NC(=O)[C@@H](NC(=O)OCc1ccccc1)C(Cc1ccccc1)C(=O)O)C(=O)O>>COC[C@H](NC(=O)[C@@H](C)NC(=O)[C@@H](N)CC(=O)O)c1ccccc1 | C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C(O)=O)CC1=CC=CC=C1)C(=O)N[C@H](C)C(=O)O.Cl.COC[C@@H](C1=CC=CC=C1)N>>COC[C@@H](C1=CC=CC=C1)NC([C@H](NC([C@@H](N)CC(O)=O)=O)C)=O | [CH3:1][O:2][CH2:3][C@H:4]([NH2:5])[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1.O=C(OCc1ccccc1)[NH:14][C@H:13]([C:11]([NH:10][C@@H:8]([C:6](O)=[O:7])[CH3:9])=[O:12])[CH:15](Cc1ccccc1)[C:16](=[O:17])[OH:18]>>[CH3:1][O:2][CH2:3][C@H:4]([NH:5][C:6](=[O:7])[C@@H:8]([CH3:9])[NH:10][C:11](=[O:12])[C@@H:13]([NH2:14])[CH2:15][C... | COC[C@H](N)c1ccccc1.C[C@@H](NC(=O)[C@@H](NC(=O)OCc1ccccc1)C(Cc1ccccc1)C(=O)O)C(=O)O | COC[C@H](NC(=O)[C@@H](C)NC(=O)[C@@H](N)CC(=O)O)c1ccccc1 | null | null | null | Acylation | OtherReaction | fe1a4b0374f25b0ed4760d7d65c253df5c8960faebba6bf1475bd86a65cd06fd | 337ca72c0bb1979769aac1fc7825c6586b8e75bbb5702fd9212c320d1f1752db | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6](=[O;D1;H0:7])-[C:8](-[NH;D2;+0:9]-C(=O)-O-C-c1:c:c:c:c:c:1)-[CH;D3;+0:10](-C-c1:c:c:c:c:c:1)-[C:11](=[O;D1;H0:12])-[O;D1;H1:13].[C:14]-[C:15](-[NH2;D1;+0:16])-[c:17]>>[C:14]-[C:15](-[c:17])-[NH;D2;+0:16]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7... | 57.3 | [{"value": 57.3, "product": "COC[C@@H](C1=CC=CC=C1)NC([C@H](NC([C@@H](N)CC(O)=O)=O)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The same process as in Example 15 was repeated, except that N-benzyloxycarbonyl-β-benzyl-L-aspartyl-D-alanine was used in place of N-benzyloxycarbonyl-β-benzyl-L-aspartyl-D-valine and that (R)-α-methoxymethylbenzylamine hydrochloride was used in place of (R)-α-ethoxymethyl benzylamine hydrochloride, and α-L-aspartyl-D-... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Primary amine | Secondary amide.Primary amine | c1ccccc1.c1ccccc1 | null | c1ccccc1 | HO- | null | null | null | COC[C@H](N)c1ccccc1.C[C@@H](NC(=O)[C@@H](NC(=O)OCc1ccccc1)C(Cc1ccccc1)C(=O)O)C(=O)O>>COC[C@H](NC(=O)[C@@H](C)NC(=O)[C@@H](N)CC(=O)O)c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d6db1ba811484e3384ed2f23fdfc613c | O=P([O-])([O-])[O-]>>O=P([O-])([O-])[O-].O=P([O-])([O-])[O-].[Ca+2].[Ca+2] | P(=O)([O-])([O-])[O-].[Na+].[Na+].[Na+].[Cl-].[Ca+2].[Cl-]>>P(=O)([O-])([O-])[O-].[Ca+2].[Ca+2].[Ca+2].P(=O)([O-])([O-])[O-] | [O:1]=[P:2]([O-:3])([O-:4])[O-:8]>>[O:1]=[P:2]([O-:3])([O-:4])[O-:5].[O:6]=[P:7]([O-:8])([O-:9])[O-:10].[Ca+2:12].[Ca+2:13] | O=P([O-])([O-])[O-] | O=P([O-])([O-])[O-].O=P([O-])([O-])[O-].[Ca+2].[Ca+2] | null | null | O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | [O-;H0;D1:1]-[P;H0;D4;+0:2](-[O;-;D1;H0:3])(-[O;-;D1;H0:4])=[O;D1;H0:5]>>[O-;H0;D1:1]-[#15:6](-[O;-;D1;H0:7])(-[O;-;D1;H0:8])=[O;D1;H0:9].[O;-;D1;H0:3]-[P;H0;D4;+0:2](-[O;-;D1;H0:4])(-[O;-;D1;H0:10])=[O;D1;H0:5] | null | [] | null | null | null | null | 78.6 Grams of sodium phosphate were dissolved in 300 grams of water. In a separate beaker, 45.3 grams of calcium chloride were dissolved in 300 grams of water. 200 Grams of each of the above solutions were added simultaneously to 200 grams of water, while being sheared at speeds of 12,000 rpm. This shearing was accompl... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | Other | O | null | null | O=P([O-])([O-])[O-]>O>O=P([O-])([O-])[O-].O=P([O-])([O-])[O-].[Ca+2].[Ca+2] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a5d5cdb2b6f74613b95722ef03582f33 | O=P([O-])([O-])[O-]>>O=P([O-])([O-])[O-].O=P([O-])([O-])[O-].[Ca+2].[Ca+2] | P(=O)([O-])([O-])[O-].[Na+].[Na+].[Na+].[Cl-].[Ca+2].[Cl-]>>P(=O)([O-])([O-])[O-].[Ca+2].[Ca+2].[Ca+2].P(=O)([O-])([O-])[O-] | [O:1]=[P:2]([O-:3])([O-:4])[O-:8]>>[O:1]=[P:2]([O-:3])([O-:4])[O-:5].[O:6]=[P:7]([O-:8])([O-:9])[O-:10].[Ca+2:12].[Ca+2:13] | O=P([O-])([O-])[O-] | O=P([O-])([O-])[O-].O=P([O-])([O-])[O-].[Ca+2].[Ca+2] | null | null | O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | [O-;H0;D1:1]-[P;H0;D4;+0:2](-[O;-;D1;H0:3])(-[O;-;D1;H0:4])=[O;D1;H0:5]>>[O-;H0;D1:1]-[#15:6](-[O;-;D1;H0:7])(-[O;-;D1;H0:8])=[O;D1;H0:9].[O;-;D1;H0:3]-[P;H0;D4;+0:2](-[O;-;D1;H0:4])(-[O;-;D1;H0:10])=[O;D1;H0:5] | null | [] | null | null | null | null | 78.6 Grams of sodium phosphate were dissolved in 300 grams of water. In a separate beaker, 45.3 grams of calcium chloride were dissolved in 300 grams of water. 200 Grams of each of the above solutions were added simultaneously to 200 grams of water, while being sheared at speeds of 12,000 rpm. This shearing was necessa... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | Other | O | null | null | O=P([O-])([O-])[O-]>O>O=P([O-])([O-])[O-].O=P([O-])([O-])[O-].[Ca+2].[Ca+2] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1486324d16694ddca5c93306441d16d7 | O=P([O-])([O-])[O-]>>O=P([O-])([O-])[O-].O=P([O-])([O-])[O-].[Ca+2].[Ca+2] | P(=O)([O-])([O-])[O-].[Na+].[Na+].[Na+].[Cl-].[Ca+2].[Cl-]>>P(=O)([O-])([O-])[O-].[Ca+2].[Ca+2].[Ca+2].P(=O)([O-])([O-])[O-] | [O:1]=[P:2]([O-:3])([O-:4])[O-:8]>>[O:1]=[P:2]([O-:3])([O-:4])[O-:5].[O:6]=[P:7]([O-:8])([O-:9])[O-:10].[Ca+2:12].[Ca+2:13] | O=P([O-])([O-])[O-] | O=P([O-])([O-])[O-].O=P([O-])([O-])[O-].[Ca+2].[Ca+2] | null | null | O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | [O-;H0;D1:1]-[P;H0;D4;+0:2](-[O;-;D1;H0:3])(-[O;-;D1;H0:4])=[O;D1;H0:5]>>[O-;H0;D1:1]-[#15:6](-[O;-;D1;H0:7])(-[O;-;D1;H0:8])=[O;D1;H0:9].[O;-;D1;H0:3]-[P;H0;D4;+0:2](-[O;-;D1;H0:4])(-[O;-;D1;H0:10])=[O;D1;H0:5] | null | [] | null | null | null | null | 78.6 Grams of sodium phosphate (TCP) were dissolved in 300 grams of water. In a separate beaker, 45.3 grams of calcium chloride were dissolved in 300 grams of water. 200 Grams of each of the above solutions were added simultaneously to 200 grams of water, while being sheared at speeds of 12,000 rpm. This shearing was a... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | Other | O | null | null | O=P([O-])([O-])[O-]>O>O=P([O-])([O-])[O-].O=P([O-])([O-])[O-].[Ca+2].[Ca+2] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-59691e7705044240a0b61a8537732528 | O=P([O-])([O-])[O-]>>O=P([O-])([O-])[O-].O=P([O-])([O-])[O-].[Ca+2].[Ca+2] | P(=O)([O-])([O-])[O-].[Na+].[Na+].[Na+].[Cl-].[Ca+2].[Cl-]>>P(=O)([O-])([O-])[O-].[Ca+2].[Ca+2].[Ca+2].P(=O)([O-])([O-])[O-] | [O:1]=[P:2]([O-:3])([O-:4])[O-:8]>>[O:1]=[P:2]([O-:3])([O-:4])[O-:5].[O:6]=[P:7]([O-:8])([O-:9])[O-:10].[Ca+2:12].[Ca+2:13] | O=P([O-])([O-])[O-] | O=P([O-])([O-])[O-].O=P([O-])([O-])[O-].[Ca+2].[Ca+2] | null | null | O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | [O-;H0;D1:1]-[P;H0;D4;+0:2](-[O;-;D1;H0:3])(-[O;-;D1;H0:4])=[O;D1;H0:5]>>[O-;H0;D1:1]-[#15:6](-[O;-;D1;H0:7])(-[O;-;D1;H0:8])=[O;D1;H0:9].[O;-;D1;H0:3]-[P;H0;D4;+0:2](-[O;-;D1;H0:4])(-[O;-;D1;H0:10])=[O;D1;H0:5] | null | [] | null | null | null | null | 39.3 Grams of sodium phosphate were dissolved in 150 grams of water (Solution A). In a separate beaker, 22.65 grams of calcium chloride were dissolved in 150 grams of water (Solution B). Each of the above solutions were added simultaneously to 200 grams of water, while being sheared at speeds of 12,000 rpm. This sheari... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | Other | O | null | null | O=P([O-])([O-])[O-]>O>O=P([O-])([O-])[O-].O=P([O-])([O-])[O-].[Ca+2].[Ca+2] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d6f09b988e0848769dd846f380d71108 | BrCCC1OCCCO1.O=Cc1ccc(O)cc1>>O=Cc1ccc(OCCC2OCCCO2)cc1 | OC1=CC=C(C=O)C=C1.BrCCC1OCCCO1.[I-].[K+].C([O-])([O-])=O.[K+].[K+]>>O1C(OCCC1)CCOC1=CC=C(C=O)C=C1 | Br[CH2:8][CH2:9][CH:10]1[O:11][CH2:12][CH2:13][CH2:14][O:15]1.[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[cH:16][cH:17]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][CH2:9][CH:10]2[O:11][CH2:12][CH2:13][CH2:14][O:15]2)[cH:16][cH:17]1 | BrCCC1OCCCO1.O=Cc1ccc(O)cc1 | O=Cc1ccc(OCCC2OCCCO2)cc1 | null | null | C(C)#N.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(OCCC2OCCCO2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3](-[#8:4])-[#8:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[#8:4]-[C:3](-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9])-[#8:5] | 100.2 | [{"value": 100.2, "product": "O1C(OCCC1)CCOC1=CC=C(C=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a 500 ml flask, 120 ml of acetonitrile, 13.8 g of 4-hydroxybenzaldehyde, 21.1 g of 2-(2-bromoethyl)-1,3-dioxane, 1.8 g of potassium iodide, and 35.8 g of potassium carbonate were placed and then, reacted at 80° C. for 5 hrs. Thereafter, 200 ml of ethyl acetate was added to the reaction mixture and washed once with a... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.C1COCOC1 | HBr | C(C)#N.C(C)(=O)OCC | null | null | BrCCC1OCCCO1.O=Cc1ccc(O)cc1>C(C)#N.C(C)(=O)OCC>O=Cc1ccc(OCCC2OCCCO2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7962a8e3cbfa49e3aabf54e37edc9672 | O=Cc1ccc(OCCC2OCCCO2)cc1>>C=Cc1ccc(OCCC2OCCCO2)cc1 | CC(C)([O-])C.[K+].O1C(OCCC1)CCOC1=CC=C(C=O)C=C1>>C(=C)C1=CC=C(OCCC2OCCCO2)C=C1 | O=[CH:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][CH2:9][CH:10]2[O:11][CH2:12][CH2:13][CH2:14][O:15]2)[cH:16][cH:17]1>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][CH2:9][CH:10]2[O:11][CH2:12][CH2:13][CH2:14][O:15]2)[cH:16][cH:17]1 | O=Cc1ccc(OCCC2OCCCO2)cc1 | C=Cc1ccc(OCCC2OCCCO2)cc1 | null | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | CCOCC | Functional Group Interconversion | OtherReaction | dd6fb167b4e71f3ea190d18ad4e87d18c641d879b83b47beb9dc06bc791584b1 | 6b3ec9b506a5bb4882685e77a1e07fcb518f891061dfbc2d36767289330c841e | c1ccc(OCCC2OCCCO2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[C;D1;H2:5]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 77.6 | [{"value": 77.6, "product": "C(=C)C1=CC=C(OCCC2OCCCO2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In another 2 liter flask, 57.2 g of methyl triphenylphosphonium bromide was placed. 500 ml of anhydrous ether was poured and then, stirred. To the resulting solution was slowly added 18.0 g of potassium tert-butoxide and reacted at room temperature for 3 hrs. 25.6 g of the above 4-(2-[1,3]-dioxane-2-yl-ethoxy)benzaldeh... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Vinyl | null | null | c1ccccc1.C1COCOC1 | null | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CCOCC | null | null | O=Cc1ccc(OCCC2OCCCO2)cc1>[Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CCOCC>C=Cc1ccc(OCCC2OCCCO2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ab767623531e408bb0c0320b5128145a | BrCCC1OCCCO1.O=Cc1ccc(O)cc1>>O=Cc1ccc(OCCC2OCCO2)cc1 | OC1=CC=C(C=O)C=C1.BrCCC1OCCCO1.[I-].[K+].C([O-])([O-])=O.[K+].[K+]>>O1C(OCC1)CCOC1=CC=C(C=O)C=C1 | Br[CH2:8][CH2:9][CH:10]1[O:11]C[CH2:12][CH2:13][O:14]1.[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[cH:15][cH:16]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][CH2:9][CH:10]2[O:11][CH2:12][CH2:13][O:14]2)[cH:15][cH:16]1 | BrCCC1OCCCO1.O=Cc1ccc(O)cc1 | O=Cc1ccc(OCCC2OCCO2)cc1 | null | null | C(C)#N.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 24613dad146d6f65990f4e10246ab7aa40915a0fa1bff65ca86c86d680144d71 | 17a5cb981f33d078202f898d6abaccae50e134a8471573b2aaa89065aa8f4efa | c1ccc(OCCC2OCCO2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]1-[#8:4]-[C:5]-[CH2;D2;+0:6]-C-[O;H0;D2;+0:7]-1.[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[c:10]:[c:9](-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[C:2]-[C:3]1-[#8:4]-[C:5]-[CH2;D2;+0:6]-[O;H0;D2;+0:7]-1):[c:11] | 104.5 | [{"value": 104.5, "product": "O1C(OCC1)CCOC1=CC=C(C=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a 500 ml flask, 120 ml of acetonitrile, 13.8 g of 4-hydroxybenzaldehyde, 19.9 g of 2-(2-bromoethyl)-1,3-dioxane, 1.8 g of potassium iodide, and 35.8 g of potassium carbonate were placed and then, reacted at 80° C. for 5 hr. Thereafter, to the reaction mixture was added 200 ml of ethyl acetate and washed once with a ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Aromatic alcohol.Acetal/Ketal | Ether.Ether | C1COCOC1 | C1COCO1 | c1ccccc1.C1COCO1 | HBr | C(C)#N.C(C)(=O)OCC | null | null | BrCCC1OCCCO1.O=Cc1ccc(O)cc1>C(C)#N.C(C)(=O)OCC>O=Cc1ccc(OCCC2OCCO2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-09284bc5f4434b24a76abcd1557a624c | O=Cc1ccc(OCCC2OCCO2)cc1>>C=Cc1ccc(OCCC2OCCO2)cc1 | CC(C)([O-])C.[K+].O1C(OCC1)CCOC1=CC=C(C=O)C=C1>>C(=C)C1=CC=C(OCCC2OCCO2)C=C1 | O=[CH:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][CH2:9][CH:10]2[O:11][CH2:12][CH2:13][O:14]2)[cH:15][cH:16]1>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][CH2:9][CH:10]2[O:11][CH2:12][CH2:13][O:14]2)[cH:15][cH:16]1 | O=Cc1ccc(OCCC2OCCO2)cc1 | C=Cc1ccc(OCCC2OCCO2)cc1 | null | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | CCOCC | Functional Group Interconversion | OtherReaction | dd6fb167b4e71f3ea190d18ad4e87d18c641d879b83b47beb9dc06bc791584b1 | 6b3ec9b506a5bb4882685e77a1e07fcb518f891061dfbc2d36767289330c841e | c1ccc(OCCC2OCCO2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[C;D1;H2:5]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 88.5 | [{"value": 88.5, "product": "C(=C)C1=CC=C(OCCC2OCCO2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In another 2 liter flask, 57.2 g of methyl triphenylphosphonium bromide was placed. 500 ml of anhydrous ether was poured and then, stirred. To the resulting solution was slowly added 18.0 g of potassium tert-butoxide and reacted at room temperature for 3 hrs. 23.7 g of the above 4-(2-[1,3]-dioxolan-2-yl-ethoxy)benzalde... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Vinyl | null | null | c1ccccc1.C1COCO1 | null | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CCOCC | null | null | O=Cc1ccc(OCCC2OCCO2)cc1>[Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CCOCC>C=Cc1ccc(OCCC2OCCO2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ddf67391f0ff4ca08b0e3124c9c5cf53 | C=O.Cc1cccc(O)c1>>Cc1cccc(O)c1C=O | CCOCCOC(=O)C.C1=C(C=CC=C1O)C.OCC1=CC(=CC(=C1O)CO)C.O.O.C(C(=O)O)(=O)O.C=O>>C=1(C(=CC=CC1O)C)C=O | [CH2:9]=[O:10].[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([OH:7])[cH:8]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([OH:7])[c:8]1[CH:9]=[O:10] | C=O.Cc1cccc(O)c1 | Cc1cccc(O)c1C=O | null | null | O | C-C Coupling | OtherReaction | 6bafee88871e7df55b2a6a706a8a62d4f54a2873abef1ac73ed67da72b977665 | 0102b88d9700d39435e06971744797a0ad3df95b36c61ce095d6702bc41b05ed | c1ccccc1 | [C;D1;H3:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5](-[O;D1;H1:6]):[c:7].[CH2;D1;+0:8]=[O;D1;H0:9]>>[C;D1;H3:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[CH;D2;+0:8]=[O;D1;H0:9]):[c:5](-[O;D1;H1:6]):[c:7] | null | [] | 70 | CELSIUS | null | null | A phenolic resin rich in alternating phenolic copolymer block segments was formed by reacting a mixture of 519.0 g of 99 percent pure m-cresol, 538.2 g of 97 percent pure 2,6-bis(hydroxymethyl)-p-cresol and 20 g oxalic acid dihydrate in a solvent mixture of 40 ml deionized water and 200 ml ethyl cellosolve acetate. The... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde | Aldehyde | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | O | 70 | null | C=O.Cc1cccc(O)c1>O>Cc1cccc(O)c1C=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3c799edf560b44e4b1b3a6fde9733781 | CCC(O)CC(CC)COC(=O)c1ccccc1.O=c1[nH]c(=O)n(C2CCCO2)cc1F>>CCCCCC(O)CCCOC(=O)c1ccccc1 | CCC1(CC[Se]C(=N1)C2=CC=C(C=C2)C)O.O.CCC1(CC[Se]C(=N1)C2=CC=C(C=C2)C)O.O.C1CC(OC1)N2C=C(C(=O)NC2=O)F.O.C1CC(OC1)N2C=C(C(=O)NC2=O)F.CCC1(CC[Se]C(=N1)C2=CC=C(C=C2)C)O.C(C1=CC=CC=C1)(=O)OCC(CC(CC)O)CC.CCC1(CC[Se]C(=N1)C2=CC=C(C=C2)C)O>>C(C1=CC=CC=C1)(=O)OCCCC(CCCCC)O.CCC1(CC[Se]C(=N1)C2=CC=C(C=C2)C)O | [CH3:17][CH2:18][CH:25]([CH2:24][CH:22]([CH2:21][CH3:20])[OH:23])[CH2:26][O:27][C:28](=[O:29])[c:30]1[cH:31][cH:32][cH:33][cH:34][cH:35]1.O=c1[nH]c(=O)n(C2CC[CH2:19]O2)cc1F>>[CH3:17][CH2:18][CH2:19][CH2:20][CH2:21][CH:22]([OH:23])[CH2:24][CH2:25][CH2:26][O:27][C:28](=[O:29])[c:30]1[cH:31][cH:32][cH:33][cH:34][cH:35]1 | CCC(O)CC(CC)COC(=O)c1ccccc1.O=c1[nH]c(=O)n(C2CCCO2)cc1F | CCCCCC(O)CCCOC(=O)c1ccccc1 | null | null | C(C)(=O)OCC | C-C Coupling | OtherReaction | 8aa343242f560868162bc4f061365910c862521d61784180f1ab2ce677652f9e | 649efb2c97ef6d79ca96edfb26bc2ec99d0c0f6512ddbe35dab89de84361ac0e | c1ccccc1 | F-c1:c:n(-C2-C-C-[CH2;D2;+0:1]-O-2):c(=O):[nH]:c:1=O.[C;D1;H3:2]-[CH2;D2;+0:3]-[CH;D3;+0:4](-[C:5]-[C:6]-[C:7]-[CH3;D1;+0:8])-[C:9]-[#8:10]-[C:11]=[O;D1;H0:12]>>[C;D1;H3:2]-[CH2;D2;+0:3]-[CH2;D2;+0:1]-[CH2;D2;+0:8]-[C:7]-[C:6]-[C:5]-[CH2;D2;+0:4]-[C:9]-[#8:10]-[C:11]=[O;D1;H0:12] | null | [] | null | null | 123 | HOUR | A comparison thermal solvent dispersion 4-hydroxy-(2'-ethylhexyl) benzoate (TS-1), a liquid at room temperature, is prepared by similar means. An aqueous solution of 10% (w/w) aqueous DA-9 (6 g), 8.3% aqueous gelatin (about 54 g), and water (74.9 g) is combined with 15 g TS-1, stirred, passed through a colloid mill 5 t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether | null | c1cncnc1.C1CCOC1 | null | c1ccccc1 | HF | C(C)(=O)OCC | null | 123 | CCC(O)CC(CC)COC(=O)c1ccccc1.O=c1[nH]c(=O)n(C2CCCO2)cc1F>C(C)(=O)OCC>CCCCCC(O)CCCOC(=O)c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bfcf42b524d14d69860f018538be3094 | O=C1OCCO1.Oc1ccc(C2(c3ccc(O)cc3)c3ccccc3-c3ccccc32)cc1>>OCCOc1ccccc1-c1cccc2c1-c1ccccc1C2 | OC1=CC=C(C=C1)C1(C2=CC=CC=C2C=2C=CC=CC12)C1=CC=C(C=C1)O.C1(OCCO1)=O.C([O-])([O-])=O.[K+].[K+].C1COCCOCCOCCOCCOCCO1>>OCCOC1=C(C=CC=C1)C1=CC=CC=2CC3=CC=CC=C3C12 | O=C1O[CH2:3][CH2:2][O:1]1.O[c:19]1[cH:18]c[c:22]([C:23]2([c:15]3ccc([OH:4])cc3)[c:5]3[cH:6][cH:7][cH:8][cH:9][c:10]3-[c:11]3[cH:12][cH:13][cH:14][cH:17][c:16]32)[cH:21][cH:20]1>>[OH:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1-[c:11]1[cH:12][cH:13][cH:14][c:15]2[c:16]1-[c:17]1[cH:18][cH:19][cH:20][cH:21][... | O=C1OCCO1.Oc1ccc(C2(c3ccc(O)cc3)c3ccccc3-c3ccccc32)cc1 | OCCOc1ccccc1-c1cccc2c1-c1ccccc1C2 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | df715ca0ba7df6936aaaacf4305fd1fcb0a820eaffbfaa54baaef378759297af | 5486a8ebfac0c59a8344ca19908d26f620466e6525fe4d82c7bb2294d03f8004 | c1ccc(-c2cccc3c2-c2ccccc2C3)cc1 | O-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c;H0;D3;+0:4](-[C;H0;D4;+0:5]2(-[c;H0;D3;+0:6]3:c:c:c(-[OH;D1;+0:7]):c:c:3)-[c;H0;D3;+0:8]3:[cH;D2;+0:9]:[cH;D2;+0:10]:[c:11]:[c:12]:[c:13]:3-[c:14](:[c:15]):[c;H0;D3;+0:16]-2:[c:17]:[c:18]):c:[cH;D2;+0:19]:1.O=C1-O-[CH2;D2;+0:20]-[C:21]-[O;H0;D2;+0:22]-1>>[OH;D1;+0:22]-[C:21]-[CH2;D2;+0:... | 970.1 | [{"value": 67.0, "product": "OCCOC1=C(C=CC=C1)C1=CC=CC=2CC3=CC=CC=C3C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 970.1, "product": "OCCOC1=C(C=CC=C1)C1=CC=CC=2CC3=CC=CC=C3C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | A mixture of 84.4 g (0.241 mol) of 9,9-bis(4-hydroxyphenyl)fluorene, 46.7 g (0.53 mol) of ethylene carbonate, 3.3 g (0.024 mol) of potassium carbonate, and a catalytic amount of 18-crown-6 in 400 mL of xylenes was heated at reflux with mechanical stirring for 6 h. The mixture was allowed to cool slowly to room temperat... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Aromatic alcohol.Aromatic alcohol | Ether.Primary alcohol | C1COCO1.c1ccccc1.c1ccccc1.c1ccc2c(c1)Cc1ccccc12 | c1ccccc1.c1ccc2c(c1)Cc1ccccc12 | c1ccccc1.c1ccc2c(c1)Cc1ccccc12 | HO- | null | null | 6 | O=C1OCCO1.Oc1ccc(C2(c3ccc(O)cc3)c3ccccc3-c3ccccc32)cc1>>OCCOc1ccccc1-c1cccc2c1-c1ccccc1C2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a9328cbc649c44739edcb5b4674d8842 | Brc1ccccc1.C=C.O=C(Cl)/C=C/C(=O)Cl>>Brc1ccc(-c2ccc(-c3ccc(Br)cc3)o2)cc1 | C=C.BrC1=CC=CC=C1.C(\C=C\C(=O)Cl)(=O)Cl>>BrC1=CC=C(C=C1)C=1OC(=CC1)C1=CC=C(C=C1)Br | [Br:1][c:2]1[cH:3][cH:4][cH:5][cH:18][cH:19]1.[CH2:7]=[CH2:8].O=[C:10](Cl)/[CH:6]=[CH:15]/[C:13](Cl)=[O:17]>>[Br:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9](-[c:10]3[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]3)[o:17]2)[cH:18][cH:19]1 | Brc1ccccc1.C=C.O=C(Cl)/C=C/C(=O)Cl | Brc1ccc(-c2ccc(-c3ccc(Br)cc3)o2)cc1 | null | [Zn].CC(=O)O.OS(=O)(=O)O | null | Aromatic Heterocycle Formation | OtherReaction | 6334e906b97dd553271dc6aadeb9b0d0834149b672afac9fad210958c43849a1 | 916dd7a2c34c815cfac9213e102e4c813c5c7b1101358c4708b31b0b3477f315 | c1ccc(-c2ccc(-c3ccccc3)o2)cc1 | Cl-[C;H0;D3;+0:1](=O)/[CH;D2;+0:2]=[CH;D2;+0:3]/[C;H0;D3;+0:4](-Cl)=[O;H0;D1;+0:5].[CH2;D1;+0:6]=[CH2;D1;+0:7].[c:8]:[c:9]:[cH;D2;+0:10]:[c:11]:[c:12]>>[Br;D1;H0:13]-[c;H0;D3;+0:4]1:[c:14]:[c:15]:[c;H0;D3;+0:1](-[c:16]2:[cH;D2;+0:7]:[cH;D2;+0:6]:[c;H0;D3;+0:2](-[c;H0;D3;+0:10](:[c:9]:[c:8]):[c:11]:[c:12]):[o;H0;D2;+0:5... | null | [] | null | null | 5 | MINUTE | A literature procedure as known in the art for preparation of trans-di-p-bromobenzoylethylene from bromobenzene and fumaryl chloride was employed. J. B. Conant and R. E. Lutz, J. Am. Chem. Soc. 47, 881 (1925). The ethylene compound was reduced with Zn-HOAc to prepare 1,4-di-p-bromophenyl-1,4-butanedione. E. Campaigne a... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Ethylene | Aromatic halide | c1ccccc1 | c1ccccc1.c1ccoc1.c1ccccc1 | c1ccccc1.c1ccoc1.c1ccccc1 | HCl | [Zn].CC(=O)O.OS(=O)(=O)O | null | 0.083333 | Brc1ccccc1.C=C.O=C(Cl)/C=C/C(=O)Cl>[Zn].CC(=O)O.OS(=O)(=O)O>Brc1ccc(-c2ccc(-c3ccc(Br)cc3)o2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-523a53f4b10c44568fb08b813772adeb | Cc1ccc(O)cc1.O=C(c1ccc(Br)cc1)C(Br)C(Br)C(=O)c1ccc(Br)cc1>>Cc1ccc(OC(=CC(=O)c2ccc(Br)cc2)C(=O)c2ccc(Br)cc2)cc1 | BrC(C(C(C1=CC=C(C=C1)Br)=O)Br)C(C1=CC=C(C=C1)Br)=O.CC1=CC=C([O-])C=C1.[Na+].CC1=CC=C(C=C1)O>>C1(=CC=C(C=C1)OC(=CC(C1=CC=C(C=C1)Br)=O)C(C1=CC=C(C=C1)Br)=O)C | [CH3:1][c:2]1[cH:3][cH:4][c:5]([OH:6])[cH:27][cH:28]1.Br[CH:7]([CH:8](Br)[C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]([Br:15])[cH:16][cH:17]1)[C:18](=[O:19])[c:20]1[cH:21][cH:22][c:23]([Br:24])[cH:25][cH:26]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][C:7](=[CH:8][C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([Br:15])[cH:16][cH:17]... | Cc1ccc(O)cc1.O=C(c1ccc(Br)cc1)C(Br)C(Br)C(=O)c1ccc(Br)cc1 | Cc1ccc(OC(=CC(=O)c2ccc(Br)cc2)C(=O)c2ccc(Br)cc2)cc1 | null | null | C1CCOC1 | Acylation | OtherReaction | 0c01c8d1b72d5246aee04cd6975436df9329b5c10637169f65d6189357d3c30c | 09cec239b0b6e49e0acb2e2466eb2c9a4619e2d6379c5e3c36cbb774978fd272 | O=C(C=C(Oc1ccccc1)C(=O)c1ccccc1)c1ccccc1 | Br-[CH;D3;+0:1](-[C:2](=[O;D1;H0:3])-[c:4])-[CH;D3;+0:5](-Br)-[C:6](=[O;D1;H0:7])-[c:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[O;D1;H0:7]=[C:6](-[c:8])-[CH;D2;+0:5]=[C;H0;D3;+0:1](-[O;H0;D2;+0:9]-[c:10](:[c:11]):[c:12])-[C:2](=[O;D1;H0:3])-[c:4] | null | [] | null | null | null | null | To a solution of 1,2-dibromo-1,2-di(4-bromobenzoyl) ethane (11.1 g, 0.02 mole) in 35 ml of THF was added a suspension of sodium 4-methyl phenoxide [prepared from 0.92 g (0.04 mole) Na and 4.32 g (0.04 mole) 4-methylphenol in 30 ml THF by refluxing for 4-5 hr]. The yellow mixture was refluxed for 2-3 hr (TLC followed) a... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary halide.Ketone.Ketone.Aromatic alcohol | Ketone.Ketone.Ether | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HBr | C1CCOC1 | null | null | Cc1ccc(O)cc1.O=C(c1ccc(Br)cc1)C(Br)C(Br)C(=O)c1ccc(Br)cc1>C1CCOC1>Cc1ccc(OC(=CC(=O)c2ccc(Br)cc2)C(=O)c2ccc(Br)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-67300f99f22241ef9811a9c1212c4492 | Cc1ccc(OC(=CC(=O)c2ccc(Br)cc2)C(=O)c2ccc(Br)cc2)cc1>>Cc1ccc(Oc2cc(-c3ccc(Br)cc3)oc2-c2ccc(Br)cc2)cc1 | C1(=CC=C(C=C1)OC(=CC(C1=CC=C(C=C1)Br)=O)C(C1=CC=C(C=C1)Br)=O)C.[K+].[Br-]>>BrC1=CC=C(C=C1)C=1OC(=CC1OC1=CC=C(C=C1)C)C1=CC=C(C=C1)Br | O=[C:9]([CH:8]=[C:7]([O:6][c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:27][cH:26]1)[C:18](=[O:17])[c:19]1[cH:20][cH:21][c:22]([Br:23])[cH:24][cH:25]1)[c:10]1[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][c:9](-[c:10]3[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]3)[o:17][c:18]2-[c:19... | Cc1ccc(OC(=CC(=O)c2ccc(Br)cc2)C(=O)c2ccc(Br)cc2)cc1 | Cc1ccc(Oc2cc(-c3ccc(Br)cc3)oc2-c2ccc(Br)cc2)cc1 | null | null | P(Cl)(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | 49d0736c2f39f4e2d7410e57509abd61f9e66cfc8dc92547450ae0db4b045714 | 5865ad957f95ca487bfea3ee689ff929d9283923f0f1cd9c13dc31f3e58c64be | c1ccc(Oc2cc(-c3ccccc3)oc2-c2ccccc2)cc1 | O=[C;H0;D3;+0:1](-[CH;D2;+0:2]=[C;H0;D3;+0:3](-[#8:4]-[c:5])-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12])-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16]:[c:17]>>[c:15]:[c:14]:[c;H0;D3;+0:13](-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[c;H0;D3;+0:3](-[#8:4]-[c:5]):[c;H0;D3;+0:6](-[c;H0;D3;+0:8](:[c:9]:[c:10])... | null | [] | null | null | null | null | A solution of 5.0 g (0.01 mole) 1-(4-tolyloxy)-1,2-bis-(4-bromobenzoyl)ethylene in 10 ml phosphorus trichloride was heated under reflux for 3-4 hr (TLC followed). The excess PCl3 was removed by distillation and the residue was triturated with ice/water (exothermic reaction). The solution was extracted with dichlorometh... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | Ether | null | c1ccoc1 | c1ccccc1.c1ccoc1.c1ccccc1.c1ccccc1 | Other | P(Cl)(Cl)Cl | null | null | Cc1ccc(OC(=CC(=O)c2ccc(Br)cc2)C(=O)c2ccc(Br)cc2)cc1>P(Cl)(Cl)Cl>Cc1ccc(Oc2cc(-c3ccc(Br)cc3)oc2-c2ccc(Br)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-68a4112e542d4a8cb9aa4b70a263e0cb | C[O-].O=C(c1ccc(Br)cc1)C(Br)C(Br)C(=O)c1ccc(Br)cc1>>COC(CC(=O)c1ccc(Br)cc1)C(=O)c1ccc(Br)cc1 | [K+].[Br-].BrC(C(C(C1=CC=C(C=C1)Br)=O)Br)C(C1=CC=C(C=C1)Br)=O.C[O-].[Na+]>>BrC1=CC=C(C(=O)C(CC(C2=CC=C(C=C2)Br)=O)OC)C=C1 | [CH3:1][O-:2].Br[CH:3]([CH:4](Br)[C:5](=[O:6])[c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]1)[C:14](=[O:15])[c:16]1[cH:17][cH:18][c:19]([Br:20])[cH:21][cH:22]1>>[CH3:1][O:2][CH:3]([CH2:4][C:5](=[O:6])[c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]1)[C:14](=[O:15])[c:16]1[cH:17][cH:18][c:19]([Br:20])[cH:21][cH:22]1 | C[O-].O=C(c1ccc(Br)cc1)C(Br)C(Br)C(=O)c1ccc(Br)cc1 | COC(CC(=O)c1ccc(Br)cc1)C(=O)c1ccc(Br)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 30d8fed98bdadd8b2a888383a3dab8de487d913ac5920589429ebf7ad7dcf3d9 | aa213320aa7a0778e9a94bb461e1c1cbb2a3ad614c6158a3cc6e0f665d6a4384 | O=C(CCC(=O)c1ccccc1)c1ccccc1 | Br-[CH;D3;+0:1](-[C:2](=[O;D1;H0:3])-[c:4])-[CH;D3;+0:5](-Br)-[C:6](=[O;D1;H0:7])-[c:8].[C;D1;H3:9]-[O-;H0;D1:10]>>[C;D1;H3:9]-[O;H0;D2;+0:10]-[CH;D3;+0:1](-[CH2;D2;+0:5]-[C:6](=[O;D1;H0:7])-[c:8])-[C:2](=[O;D1;H0:3])-[c:4] | null | [] | null | null | null | null | To a solution of 1,2-dibromo-1,2-di(4-bromobenzoyl) ethane (11.1 g, 0.02 mole) in 150 mL dry methanol was added a solution of sodium methoxide in methanol (0.92 g sodium in 50 mL methanol). The yellow brown mixture was refluxed for 1-1.5 hr. The solvent was removed by distillation, the residue was suspended in water an... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary halide.Ketone.Ketone | Ketone.Ketone.Ether | null | null | c1ccccc1.c1ccccc1 | Br- | CO | null | null | C[O-].O=C(c1ccc(Br)cc1)C(Br)C(Br)C(=O)c1ccc(Br)cc1>CO>COC(CC(=O)c1ccc(Br)cc1)C(=O)c1ccc(Br)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4d66dfcc15f145d887e1d654294844a8 | CN1CCN(c2ccc3[nH]c(-c4ccc5[nH]c(-c6ccc(O)cc6)nc5c4)nc3c2)CC1.N=C(N)c1ccc(-c2cc3ccc(C(=N)N)cc3[nH]2)cc1.c1cc(-c2ccc(-c3ccc(C4=NCCCN4)cc3)o2)ccc1C1=NCCCN1>>c1cc(-c2ccc(-c3ccc(C4=NCCCCN4)cc3)o2)ccc1C1=NCCCCN1 | N1C(=NCCC1)C1=CC=C(C=C1)C=1OC(=CC1)C1=CC=C(C=C1)C=1NCCCN1.C1=CC(=CC=C1C2=CC=3C=CC(=CC3N2)C(=N)N)C(=N)N.CN1CCN(CC1)C=2C=CC3=C(C2)N=C(N3)C=4C=CC5=C(C4)N=C(N5)C=6C=CC(=CC6)O>>N1C(=NCCCC1)C1=CC=C(C=C1)C=1OC(=CC1)C1=CC=C(C=C1)C=1NCCCCN1 | CN1CCN(c2ccc3[nH]c(-c4ccc5[nH]c(-c6ccc(O)cc6)nc5c4)nc3c2)[CH2:30]C1.N=C(N)c1ccc(-c2cc3cc[c:15](C(=N)N)cc3[nH]2)cc1.[cH:1]1[cH:2][c:3](-[c:4]2[cH:5][cH:6][c:7](-[c:8]3[cH:9][cH:10][c:11]([C:12]4=[N:13][CH2:14][CH2:16][CH2:17][NH:18]4)[cH:19][cH:20]3)[o:21]2)[cH:22][cH:23][c:24]1[C:25]1=[N:26][CH2:27][CH2:28][CH2:29][NH:... | CN1CCN(c2ccc3[nH]c(-c4ccc5[nH]c(-c6ccc(O)cc6)nc5c4)nc3c2)CC1.N=C(N)c1ccc(-c2cc3ccc(C(=N)N)cc3[nH]2)cc1.c1cc(-c2ccc(-c3ccc(C4=NCCCN4)cc3)o2)ccc1C1=NCCCN1 | c1cc(-c2ccc(-c3ccc(C4=NCCCCN4)cc3)o2)ccc1C1=NCCCCN1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 16fdd18051c08c59232736fc13e6ae53f0b55591fdcbe5ccb88d809a75eeb6bf | 2711c5bea920b1e97b6e459826f77141c3e4a17c18d9b13aa6a7b0e856cea35f | c1cc(-c2ccc(-c3ccc(C4=NCCCCN4)cc3)o2)ccc1C1=NCCCCN1 | C-N1-C-C-N(-c2:c:c:c3:[nH]:c(-c4:c:c:c5:[nH]:c(-c6:c:c:c(-O):c:c:6):n:c:5:c:4):n:c:3:c:2)-[CH2;D2;+0:1]-C-1.N-C(=N)-[c;H0;D3;+0:2]1:c:c:c2:c:c(-c3:c:c:c(-C(-N)=N):c:c:3):[nH]:c:2:c:1.[c:3]-[C:4]1=[#7:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[C:8]-[#7:9]-1.[c:10]-[C:11]1=[#7:12]-[C:13]-[C:14]-[CH2;D2;+0:15]-[NH;D2;+0:16]-1>>[c:3]... | null | [] | null | null | null | null | 2,5-bis[4-(1,4,5,6-tetrahydropyrimidin-2-yl)phenyl] furan (DB103), in comparison to the compounds DAPI and Hoechst 33258.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Primary amine.Primary amine.Secondary amine.Tertiary amine.Tertiary amine | Secondary amine | C1CNCCN1.c1ccc2[nH]cnc2c1.c1ccc2[nH]cnc2c1.c1ccccc1.c1ccccc1.c1ccc2[nH]ccc2c1.C1=NCCCN1.C1=NCCCN1 | C1=NCCCCN1.C1=NCCCCN1 | c1ccccc1.c1ccoc1.c1ccccc1.C1=NCCCCN1.C1=NCCCCN1 | HO- | null | null | null | CN1CCN(c2ccc3[nH]c(-c4ccc5[nH]c(-c6ccc(O)cc6)nc5c4)nc3c2)CC1.N=C(N)c1ccc(-c2cc3ccc(C(=N)N)cc3[nH]2)cc1.c1cc(-c2ccc(-c3ccc(C4=NCCCN4)cc3)o2)ccc1C1=NCCCN1>>c1cc(-c2ccc(-c3ccc(C4=NCCCCN4)cc3)o2)ccc1C1=NCCCCN1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a502aa411b624e959a294d1ade8139de | NCCCCC(N)C(=O)O>>NCCCC[C@@H](N)C(=O)O | S(=O)(=O)([O-])[O-].[Mg+2].Cl.NC(CCCCN)C(=O)O.S(=O)(=O)([O-])[O-].[NH4+].[NH4+].Cl.P(=O)(O)(O)[O-].[K+]>>Cl.N[C@H](CCCCN)C(=O)O | [NH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]([NH2:8])[C:9](=[O:10])[OH:11]>>[NH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]([NH2:8])[C:9](=[O:10])[OH:11] | NCCCCC(N)C(=O)O | NCCCC[C@@H](N)C(=O)O | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | 10 | MINUTE | Into a shaking flask having a volume of 500 ml was charged 100 ml of a medium (pH 7.0) comprising 2% of DL-lysine monohydrochloride, 0.2% of ammonium sulfate, 0.1% of potassium dihydrogen phosphate, 0.05% of magnesium sulfate and 0.02% of a yeast extract, and the medium was sterilized at 120° C. for 10 minutes. A loopf... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | null | null | 0.166667 | NCCCCC(N)C(=O)O>>NCCCC[C@@H](N)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bea45d3f17ff4aeeb2836945fd80d389 | NCCCC[C@H](N)C(=O)O>>NCCCC[C@@H](N)C(=O)O | Cl.NC(CCCCN)C(=O)O.N[C@@H](CCCCN)C(=O)O>>Cl.N[C@H](CCCCN)C(=O)O | [NH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@H:7]([NH2:8])[C:9](=[O:10])[OH:11]>>[NH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]([NH2:8])[C:9](=[O:10])[OH:11] | NCCCC[C@H](N)C(=O)O | NCCCC[C@@H](N)C(=O)O | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | 10 | MINUTE | Into a shaking flask having a volume of 500 ml was charged ml of a medium (pH 7.0) comprising 0.5% of DL-lysine monohydrochloride, 1.0% of polypeptone, 1.0% of a yeast extract and 0.5% of sodium chloride, and the medium was sterilized at 120° C. for 10 minutes. A loopful of Pseudomonas sp. ATCC 14676 was inoculated int... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | null | null | 0.166667 | NCCCC[C@H](N)C(=O)O>>NCCCC[C@@H](N)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9053e57f398646fcad52b73dfd0e8b51 | C[O-].Cn1ncc(Br)c(Br)c1=O>>COc1cnn(C)c(=O)c1Br | BrC=1C(N(N=CC1Br)C)=O.C[O-].[Na+]>>BrC=1C(N(N=CC1OC)C)=O | [CH3:1][O-:2].Br[c:3]1[cH:4][n:5][n:6]([CH3:7])[c:8](=[O:9])[c:10]1[Br:11]>>[CH3:1][O:2][c:3]1[cH:4][n:5][n:6]([CH3:7])[c:8](=[O:9])[c:10]1[Br:11] | C[O-].Cn1ncc(Br)c(Br)c1=O | COc1cnn(C)c(=O)c1Br | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | a9b48706c0031de50054078adf178cdb9c97933ae9a69eb837163dea0dd09084 | 51fd03eb6a688046e417b9ed09ea0e72062396d005af1318b9b5f376a97da959 | O=c1cccn[nH]1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[#7;a:4](-[C;D1;H3:5]):[c:6](=[O;D1;H0:7]):[c:8]:1-[Br;D1;H0:9].[C;D1;H3:10]-[O-;H0;D1:11]>>[Br;D1;H0:9]-[c:8]1:[c:6](=[O;D1;H0:7]):[#7;a:4](-[C;D1;H3:5]):[#7;a:3]:[c:2]:[c;H0;D3;+0:1]:1-[O;H0;D2;+0:11]-[C;D1;H3:10] | null | [] | 23 | CELSIUS | 3 | HOUR | 4,5-Dibromo-2-methyl-3(2H)-pyridazinone (20 g, Maybridge Chemical Company) was cooled in an ice bath and treated successively with methanol (200 mL) and sodium methoxide (12 mL of a 30% solution in methanol). The ice bath was removed and the reaction was allowed to stir at 23° C. for 3 h. The methanol was removed by ev... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Ether | c1ccnnc1 | c1ccnnc1 | c1ccnnc1 | Br- | CO | 23 | 3 | C[O-].Cn1ncc(Br)c(Br)c1=O>CO>COc1cnn(C)c(=O)c1Br |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-415b27028875405d86f41fbc30253639 | CN(C)C=O.Cc1cc(Br)c(C)c2c1SCCC2(C)C>>Cc1cc(C=O)c(C)c2c1SCCC2(C)C | Cl.C(CCC)[Li].BrC=1C=C(C2=C(C(CCS2)(C)C)C1C)C.CN(C=O)C>>CC1(CCSC2=C1C(=C(C=C2C)C=O)C)C | CN(C)[CH:5]=[O:6].Br[c:4]1[cH:3][c:2]([CH3:1])[c:10]2[c:9]([c:7]1[CH3:8])[C:14]([CH3:15])([CH3:16])[CH2:13][CH2:12][S:11]2>>[CH3:1][c:2]1[cH:3][c:4]([CH:5]=[O:6])[c:7]([CH3:8])[c:9]2[c:10]1[S:11][CH2:12][CH2:13][C:14]2([CH3:15])[CH3:16] | CN(C)C=O.Cc1cc(Br)c(C)c2c1SCCC2(C)C | Cc1cc(C=O)c(C)c2c1SCCC2(C)C | null | null | C(C)OCC | C-C Coupling | Bouveault aldehyde synthesis | ce4ffd3527e44cbe28d8e519bc97772f9181a7c488bf9935d273c01ecf55204f | afd09ced98f25d311f21cc04ba6a50fe7e5516de47e17484683ded13d323b1b2 | c1ccc2c(c1)CCCS2 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6].C-N(-C)-[CH;D2;+0:7]=[O;D1;H0:8]>>[C;D1;H3:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[CH;D2;+0:7]=[O;D1;H0:8]):[c:2]:[c:3] | null | [] | null | null | 1 | HOUR | 6-Bromo-3,4-dihydro-4,4,5,8-tetramethyl-2H-1-benzothiopyran (19.8 g, World Patent Application 95/04054) was dissolved in diethyl ether (350 mL) and treated with n-butyllithium (2.5N in hexanes, 42 mL). The mixture was stirred at room temperature for 1 h and then cooled in a dry-ice/acetone bath. Dimethylformamide (16 m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amide | Aldehyde | c1ccc2c(c1)CCCS2 | c1ccc2c(c1)CCCS2 | c1ccc2c(c1)CCCS2 | HBr | C(C)OCC | null | 1 | CN(C)C=O.Cc1cc(Br)c(C)c2c1SCCC2(C)C>C(C)OCC>Cc1cc(C=O)c(C)c2c1SCCC2(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bbaa547034cb4578bce2648d1c091a1f | C[S-].Clc1cc(Cl)nc(OCc2ccccc2)n1>>CSc1cc(Cl)nc(OCc2ccccc2)n1 | C[S-].[Na+].ClC1=NC(=NC(=C1)Cl)OCC1=CC=CC=C1>>ClC1=NC(=NC(=C1)SC)OCC1=CC=CC=C1 | [CH3:1][S-:2].Cl[c:3]1[cH:4][c:5]([Cl:6])[n:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[n:17]1>>[CH3:1][S:2][c:3]1[cH:4][c:5]([Cl:6])[n:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[n:17]1 | C[S-].Clc1cc(Cl)nc(OCc2ccccc2)n1 | CSc1cc(Cl)nc(OCc2ccccc2)n1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | c585a12a68e20c063c9140978e67b6bcb0ee4b45d1104487928020f382023d4a | 1813ae14fbd9cacead4dcfaf9efbd2467a19b3e216836766b78aa6647dcfb48a | c1ccc(COc2ncccn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#8:4]):[#7;a:5]:[c:6](-[Cl;D1;H0:7]):[c:8]:1.[C;D1;H3:9]-[S-;H0;D1:10]>>[#8:4]-[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[S;H0;D2;+0:10]-[C;D1;H3:9]):[c:8]:[c:6](-[Cl;D1;H0:7]):[#7;a:5]:1 | null | [] | null | null | null | null | Aqueous sodium thiomethoxide (15%, 2.75 g, 0.0059×1.0 mol) was added dropwise in 4,6-dichloro-2-(phenylmethoxy)pyrimidine (Compound No. II-26) (1.5 g, 0.0059 mol) dissolved in THF at room temperature. After allowed to react for 2 hours, the reaction solution was partitioned between ethyl acetate and aqueous saturated s... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Monosulfide | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | Other | C1CCOC1 | null | null | C[S-].Clc1cc(Cl)nc(OCc2ccccc2)n1>C1CCOC1>CSc1cc(Cl)nc(OCc2ccccc2)n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3d58caaef3e54ab9bff64df1e59b26f5 | CSc1nccc(Cl)n1.Oc1cccc(C(F)(F)F)c1>>CSc1nccc(Oc2cccc(C(F)(F)F)c2)n1 | [H-].[Na+].ClC1=NC(=NC=C1)SC.FC(C=1C=C(C=CC1)O)(F)F>>CSC1=NC=CC(=N1)OC1=CC(=CC=C1)C(F)(F)F | Cl[c:7]1[cH:6][cH:5][n:4][c:3]([S:2][CH3:1])[n:19]1.[OH:8][c:9]1[cH:10][cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18]1>>[CH3:1][S:2][c:3]1[n:4][cH:5][cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18]2)[n:19]1 | CSc1nccc(Cl)n1.Oc1cccc(C(F)(F)F)c1 | CSc1nccc(Oc2cccc(C(F)(F)F)c2)n1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 38da1e480b17968341fc50d07104da93d31f20765e3b36e5a0790cb6b1d88a10 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ccncn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#16:4]):[#7;a:5]:[c:6]:[c:7]:1.[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[#16:4]-[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11]):[c:7]:[c:6]:[#7;a:5]:1 | null | [] | null | null | null | null | In THF, a phenoxide was prepared from 3-(trifluoromethyl)phenol (4.54 g, 0.0187×1.5 mol) was mixed with NaH (1.12 g (ca. 60% in mineral oil), 0.0187×1.5 mol), and 4-chloro-2-(methylthio)pyrimidine (Compound No. VII-1) (3.0 g, 0.0187 mol) was added thereto and the mixture was refluxed for about 10 hours. The reaction so... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HCl | C1CCOC1 | null | null | CSc1nccc(Cl)n1.Oc1cccc(C(F)(F)F)c1>C1CCOC1>CSc1nccc(Oc2cccc(C(F)(F)F)c2)n1 |
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