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-c31cb9b44c404c10ba3aa533aa079e2b | ord-59347390abdc4841a5e6227ec895b081 | C#CCNc1nc(Nc2ccc(N)cc2)ncc1Br.Cn1cnc(S(=O)(=O)Cl)c1>>C#CCNc1nc(Nc2ccc(NS(=O)(=O)c3cn(C)cn3)cc2)ncc1Br | NC1=CC=C(C=C1)NC1=NC=C(C(=N1)NCC#C)Br.C(C)N(CC)CC.CN1C=NC(=C1)S(=O)(=O)Cl>>BrC=1C(=NC(=NC1)NC1=CC=C(C=C1)NS(=O)(=O)C=1N=CN(C1)C)NCC#C | [CH:1]#[C:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([NH2:13])[cH:23][cH:24]2)[n:25][cH:26][c:27]1[Br:28].Cl[S:14](=[O:15])(=[O:16])[c:17]1[cH:18][n:19]([CH3:20])[cH:21][n:22]1>>[CH:1]#[C:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([NH:13][S:14](=[O:15])(=[O:16])[c:17]3[cH:18]... | C#CCNc1nc(Nc2ccc(N)cc2)ncc1Br.Cn1cnc(S(=O)(=O)Cl)c1 | C#CCNc1nc(Nc2ccc(NS(=O)(=O)c3cn(C)cn3)cc2)ncc1Br | null | null | C(C)#N | Miscellaneous | Sulfonamide synthesis (Schotten-Baumann) primary amine | a86b0632821e188c0a5dc5a5a2aac298ab3eccaee8a52ba46078c3d5975a290d | 50f8fbf3d327483c3eeff8f6cbd4065e4c7600bb501fbe08958a5c79a0926428 | O=S(=O)(Nc1ccc(Nc2ncccn2)cc1)c1c[nH]cn1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4]1:[#7;a:5]:[c:6]:[#7;a:7](-[C;D1;H3:8]):[c:9]:1.[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C;D1;H3:8]-[#7;a:7]1:[c:9]:[c:4](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[#7;a:5]:[c:6]:1 | null | [] | null | null | null | null | N2-(4-Amino-phenyl)-5-bromo-N4-prop-2-ynyl-pyrimidine-2,4-diamine (100 mg, 0.3 mmole prepared in analogy to procedure 21) was dissolved in acetonitrile (10 ml) and triethylamine (1 ml) and 1-Methyl-1H-imidazole-4-sulfonyl chloride (120 mg, 0.66 mmole) was added at room temperature. The reaction mixture was stirred unde... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1cncnc1.c1ccccc1.c1c[nH]cn1 | HCl | C(C)#N | null | null | C#CCNc1nc(Nc2ccc(N)cc2)ncc1Br.Cn1cnc(S(=O)(=O)Cl)c1>C(C)#N>C#CCNc1nc(Nc2ccc(NS(=O)(=O)c3cn(C)cn3)cc2)ncc1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cc93809346c24ee095e924e7ae128999 | CI.O=C(O)C1CCC=CCCC1>>COC(=O)C1CCC=CCCC1 | C(=O)([O-])[O-].[K+].[K+].C1(CCC=CCCC1)C(=O)O.CC(=O)C.CI>>C1(CCC=CCCC1)C(=O)OC | I[CH3:1].[OH:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][CH:8]=[CH:9][CH2:10][CH2:11][CH2:12]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][CH:8]=[CH:9][CH2:10][CH2:11][CH2:12]1 | CI.O=C(O)C1CCC=CCCC1 | COC(=O)C1CCC=CCCC1 | null | null | O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 9474aa79a2adc7353c0c02444ca598a6f486ecdd7ed5edb9ae0645721ee50389 | badd4f82161bb0ee7acffd023ea4caae5d036bce7065c10ab0a06e83a6a6f119 | C1=CCCCCCC1 | I-[CH3;D1;+0:1].[C:2]-[C:3](=[O;D1;H0:4])-[OH;D1;+0:5]>>[C:2]-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-[CH3;D1;+0:1] | null | [] | null | null | 8 | HOUR | A 50 mL, 3-neck round bottom flask was charged with cyclooct-4-ene carboxylic acid (0.517 g, 3.35 mmol, prepared as described below in Example 35) and 30 mL reagent-grade acetone and vigorously stirred for several minutes. K2CO3 (1.15 g, 8.32 mmol) was then added, followed by an excess of methyl iodide (4 mL). A reflux... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | null | null | C1=CCCCCCC1 | HI | O | null | 8 | CI.O=C(O)C1CCC=CCCC1>O>COC(=O)C1CCC=CCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8e66687345bd482fa550c2174a31388a | CC(C)(C)OC(=O)C1CCC=CCCC1>>O=C(O)C1CCC=CCCC1 | C(=O)(O)[O-].[Na+].C(C)O.C1(CCC=CCCC1)C(=O)OC(C)(C)C.FC(C(=O)O)(F)F>>C1(CCC=CCCC1)C(=O)O | CC(C)(C)[O:3][C:2](=[O:1])[CH:4]1[CH2:5][CH2:6][CH:7]=[CH:8][CH2:9][CH2:10][CH2:11]1>>[O:1]=[C:2]([OH:3])[CH:4]1[CH2:5][CH2:6][CH:7]=[CH:8][CH2:9][CH2:10][CH2:11]1 | CC(C)(C)OC(=O)C1CCC=CCCC1 | O=C(O)C1CCC=CCCC1 | null | null | O | Deprotection | Deprotection of carboxylic acid | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | C1=CCCCCCC1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 69 | [{"value": 69.0, "product": "C1(CCC=CCCC1)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 6.9, "product": "C1(CCC=CCCC1)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | A 100 mL round bottom flask was charged with t-butyl cyclooct-4-ene carboxylate (1.0 g, 4.8 mmol) and trifluoroacetic acid (2 mL) and stirred at room temperature for two days. A 4:1 ethanol:water mixture (10 mL) was then added and the pH of the resulting mixture was adjusted to ˜4.0 with aqueous saturated NaHCO3. The m... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | C1=CCCCCCC1 | Other | O | null | 48 | CC(C)(C)OC(=O)C1CCC=CCCC1>O>O=C(O)C1CCC=CCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e0586bdcbf7f473a8af6a2419676ba4e | C=CCCCCCCCCCC(CCCCCCCCC=C)C(=O)O.CI>>C=CCCCCCCCCCC(CCCCCCCCC=C)C(=O)OC | C(CCCCCCCC=C)C(C(=O)O)CCCCCCCCCC=C.Cl.C(=O)([O-])[O-].[K+].[K+].CI>>C(CCCCCCCC=C)C(C(=O)OC)CCCCCCCCCC=C | [CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=[CH2:22])[C:23](=[O:24])[OH:25].I[CH3:26]>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]([CH2:13][CH2:14][CH2:15][CH2:16... | C=CCCCCCCCCCC(CCCCCCCCC=C)C(=O)O.CI | C=CCCCCCCCCCC(CCCCCCCCC=C)C(=O)OC | null | null | CC(=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 9474aa79a2adc7353c0c02444ca598a6f486ecdd7ed5edb9ae0645721ee50389 | badd4f82161bb0ee7acffd023ea4caae5d036bce7065c10ab0a06e83a6a6f119 | null | I-[CH3;D1;+0:1].[C:2]-[C:3](=[O;D1;H0:4])-[OH;D1;+0:5]>>[C:2]-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-[CH3;D1;+0:1] | 97.5 | [{"value": 97.5, "product": "C(CCCCCCCC=C)C(C(=O)OC)CCCCCCCCCC=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-(Dec-9-enyl)-tridec-12-enoic acid (63 mg, 0.18 mmol, Example 67) was added to a 100 mL three-neck round-bottom flask fitted with a reflux condenser (cooled with ice cold water) followed by 15 mL of reagent-grade acetone. The resulting solution was vigorously stirred and 0.062 g K2CO3 (0.45 mmol, 2.5 eq.) was added in... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | null | null | null | HI | CC(=O)C.C(C)(=O)OCC | null | null | C=CCCCCCCCCCC(CCCCCCCCC=C)C(=O)O.CI>CC(=O)C.C(C)(=O)OCC>C=CCCCCCCCCCC(CCCCCCCCC=C)C(=O)OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d51665ec66ee4cddb865a4238acfc063 | C=CCCCBr.CCOC(=O)CC(=O)OCC>>C=CCCCC(CCCC=C)(C(=O)OCC)C(=O)OCC | Cl.BrCCCC=C.C(CC(=O)OCC)(=O)OCC.[H-].[Na+]>>C(CCC=C)C(C(=O)OCC)(C(=O)OCC)CCCC=C | Br[CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11].[C:1]([CH2:6][C:12](=[O:13])[O:14][CH2:15][CH3:4])(=[O:18])[O:19][CH2:20][CH3:21]>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][C:6]([CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11])([C:12](=[O:13])[O:14][CH2:15][CH3:16])[C:17](=[O:18])[O:19][CH2:20][CH3:21] | C=CCCCBr.CCOC(=O)CC(=O)OCC | C=CCCCC(CCCC=C)(C(=O)OCC)C(=O)OCC | null | null | C1CCOC1 | Acylation | OtherReaction | 47e998103900e2ba5de9bdfc75a290cfb1eaaa16a40f5b05c77919f7ccebffa3 | 97b9fb4460955b20307c63f04080f1a444a3affd469d88816f6281a7c95d488e | null | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]=[C;D1;H2:5].[C;D1;H3:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:9](=[O;H0;D1;+0:10])-[CH2;D2;+0:11]-[C:12](=[O;D1;H0:13])-[#8:14]-[CH2;D2;+0:15]-[CH3;D1;+0:16]>>[C;D1;H2:5]=[C:4]-[C:3]-[C:2]-[CH2;D2;+0:1]-[C;H0;D4;+0:11](-[C:17]-[CH2;D2;+0:16]-[C:18]-[C:19]=[CH2;D1;+0:9])(-[C:12](=[O;D1;H0:1... | null | [] | null | null | 30 | MINUTE | Diethyl malonate (25 g, 156 mmol) was dissolved in 150 mL dry THF in a 3 necked round bottom flask, and NaH (18.74 g of 60% dispersion in mineral oil, 469 mmol, 3.0 eq.) was added portionwise. The suspension was magnetically stirred for 30 minutes. Subsequently, 58.1 g 5-bromo-1-pentene (390 mmol, 2.5 eq.) was added in... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ester | Ester.Ester.Allyl | null | null | null | Br- | C1CCOC1 | null | 0.5 | C=CCCCBr.CCOC(=O)CC(=O)OCC>C1CCOC1>C=CCCCC(CCCC=C)(C(=O)OCC)C(=O)OCC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b4a82f3da0c1476193e45f52501bf0d1 | C=CCCCCC(CCCCC=C)(C(=O)O)C(=O)O>>C=CCCCCC(CCCCC=C)C(=O)O | C(CCCC=C)C(C(=O)O)(C(=O)O)CCCCC=C.C(CCC=C)C(C(=O)O)(C(=O)O)CCCC=C.C(CC(=O)OCC)(=O)OCC.[H-].[Na+].BrCCCCC=C>>C(CCCC=C)C(C(=O)O)CCCCC=C | O=C(O)[C:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=[CH2:1])([CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH2:13])[C:14](=[O:15])[OH:16]>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH2:13])[C:14](=[O:15])[OH:16] | C=CCCCCC(CCCCC=C)(C(=O)O)C(=O)O | C=CCCCCC(CCCCC=C)C(=O)O | null | null | C1CCOC1 | Reduction | OtherReaction | 1dcdb0afd061fc08423f0103da81d9d30c22c6dc8004c40ee82cae1f931e4d18 | 292164ffdf89eeb341ee9424f24084b252a703a26bb77721b558b0f8a8528c45 | null | O-C(=O)-[C;H0;D4;+0:1](-[C:2]-[C:3])(-[C:4]-[C:5])-[C:6](=[O;D1;H0:7])-[O;D1;H1:8]>>[C:3]-[C:2]-[CH;D3;+0:1](-[C:4]-[C:5])-[C:6](=[O;D1;H0:7])-[O;D1;H1:8] | 13.6 | [{"value": 13.6, "product": "C(CCCC=C)C(C(=O)O)CCCCC=C", "details": "PERCENTYIELD", "is_desired": false}] | 205 | CELSIUS | 1 | HOUR | Using a procedure identical to that described in Example 58 for the synthesis of di(4-pentenyl)malonic acid, diethyl malonate (25 g, 156 mmol) was dissolved in 150 mL dry THF in a 3 necked round bottom flask, and was reacted with NaH (18.74 g of 60% dispersion in mineral oil, 469 mmol, 3.0 eq.) and 6-bromo-1-hexene (63... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | null | null | null | Other | C1CCOC1 | 205 | 1 | C=CCCCCC(CCCCC=C)(C(=O)O)C(=O)O>C1CCOC1>C=CCCCCC(CCCCC=C)C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4ef83791b27440f6aed4244de8eb74e9 | CC(=O)c1cccc(O)c1.CN(C)C(=O)Cl>>CC(=O)c1cccc(OC(=O)N(C)C)c1 | [Cl-].[Na+].OC=1C=C(C=CC1)C(C)=O.[H-].[Na+].CN(C(=O)Cl)C>>CN(C(OC1=CC(=CC=C1)C(C)=O)=O)C | [CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([OH:9])[cH:15]1.Cl[C:10](=[O:11])[N:12]([CH3:13])[CH3:14]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([O:9][C:10](=[O:11])[N:12]([CH3:13])[CH3:14])[cH:15]1 | CC(=O)c1cccc(O)c1.CN(C)C(=O)Cl | CC(=O)c1cccc(OC(=O)N(C)C)c1 | null | null | O1CCCC1 | Protection | Schotten-Baumann to ester | 76fc23af07d8d02fec539138b5d326dfd4e833212bae1d173120f54983c8b7d8 | 4c7d92b589147a4e2aa8407ff52bd0eb1be84bdb6595779d27beb0c5d6fdd0e2 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C;D1;H3:4])-[C;D1;H3:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:4]-[#7:3](-[C;D1;H3:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | 166.1 | [{"value": 166.1, "product": "CN(C(OC1=CC(=CC=C1)C(C)=O)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | Tetrahydrofuran (100 ml) was added to sodium hydride (1.94 g, 45 mmol) under an atmosphere of nitrogen. To the suspension was added a tetrahydrofuran solution of 1-(3-hydroxyphenyl)ethanone (5.05 g, 37 mmol) in an ice bath. After stirring the mixture for 15 minutes dimethylcarbamyl chloride (1.7 ml, 19 mmol) was added ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Aromatic alcohol | Carbamic ester | null | null | c1ccccc1 | HCl | O1CCCC1 | null | 4 | CC(=O)c1cccc(O)c1.CN(C)C(=O)Cl>O1CCCC1>CC(=O)c1cccc(OC(=O)N(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1b256bb1e6434c5aa777f586588f7455 | C=O.CNC(CCc1ccc(OC)cc1)c1cccc(OC(=O)N(C)C)c1>>COc1ccc(CCC(c2cccc(OC(=O)N(C)C)c2)N(C)C)cc1 | C=O.Cl.CN(C(OC1=CC(=CC=C1)C(CCC1=CC=C(C=C1)OC)NC)=O)C.[OH-].[Na+]>>CN(C(OC1=CC(=CC=C1)C(CCC1=CC=C(C=C1)OC)N(C)C)=O)C | O=[CH2:23].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][CH:9]([c:10]2[cH:11][cH:12][cH:13][c:14]([O:15][C:16](=[O:17])[N:18]([CH3:19])[CH3:20])[cH:21]2)[NH:22][CH3:24])[cH:25][cH:26]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][CH:9]([c:10]2[cH:11][cH:12][cH:13][c:14]([O:15][C:16](=[O:17])[N:18]([CH3:19])... | C=O.CNC(CCc1ccc(OC)cc1)c1cccc(OC(=O)N(C)C)c1 | COc1ccc(CCC(c2cccc(OC(=O)N(C)C)c2)N(C)C)cc1 | null | null | C(=O)O | Heteroatom Alkylation and Arylation | Eschweiler-Clarke Secondary Amine Methylation | deb0f39510ff32c3bd75ceaf7ece4070b1f686ff120d798ccd640765025dab3c | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | c1ccc(CCCc2ccccc2)cc1 | O=[CH2;D1;+0:1].[C:2]-[C:3](-[c:4])-[NH;D2;+0:5]-[C;D1;H3:6]>>[C:2]-[C:3](-[c:4])-[N;H0;D3;+0:5](-[C;D1;H3:6])-[CH3;D1;+0:1] | null | [] | 90 | CELSIUS | 2 | HOUR | Formic acid (10 ml) and 35% aqueous formaldehyde solution (10 ml) were added to 3-[3-(4-methoxyphenyl)-1-methylaminopropyl]phenyl dimethylcarbamate (500 mg, 1.4 mmol) obtained from Example 2 and the mixture was stirred at 90° C. for 2 hours. After cooling the reaction mixture to room temperature the mixture was neutral... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1ccccc1 | Other | C(=O)O | 90 | 2 | C=O.CNC(CCc1ccc(OC)cc1)c1cccc(OC(=O)N(C)C)c1>C(=O)O>COc1ccc(CCC(c2cccc(OC(=O)N(C)C)c2)N(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-72bd2770a33541b1b31746c0c8b803dd | CN.O=C(O)CC(=O)O.O=Cc1cccc(O)c1>>CNC(CC(=O)O)c1cccc(O)c1 | OC=1C=C(C=O)C=CC1.C(CC(=O)O)(=O)O.C(C)(=O)O.CN>>OC=1C=C(C=CC1)C(CC(=O)O)NC | [CH3:1][NH2:2].O=C(O)[CH2:4][C:5](=[O:6])[OH:7].O=[CH:3][c:8]1[cH:9][cH:10][cH:11][c:12]([OH:13])[cH:14]1>>[CH3:1][NH:2][CH:3]([CH2:4][C:5](=[O:6])[OH:7])[c:8]1[cH:9][cH:10][cH:11][c:12]([OH:13])[cH:14]1 | CN.O=C(O)CC(=O)O.O=Cc1cccc(O)c1 | CNC(CC(=O)O)c1cccc(O)c1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 029574ef26de21f885bdd45bc4c594df31907abcec9280dfb6bae6d8c823e790 | b3ae5256a03516152477e54cb65b2c8ce8e6de1b7a097a5a730c0f14a2ab31ca | c1ccccc1 | O-C(=O)-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[O;D1;H1:4].O=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8].[C;D1;H3:9]-[NH2;D1;+0:10]>>[C;D1;H3:9]-[NH;D2;+0:10]-[CH;D3;+0:5](-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[O;D1;H1:4])-[c:6](:[c:7]):[c:8] | 58.8 | [{"value": 58.8, "product": "OC=1C=C(C=CC1)C(CC(=O)O)NC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-Hydroxybenzaldehyde (25.7 g, 210 mmol) was dissolved in ethanol (70 ml), and malonic acid (25.7 g) and the acetic acid salt of methylamine (38.6 g) were added to the solution. The resulting mixture was heated under reflux for 3 hours. Crystals which precipitated in the reaction mixture were collected by filtration to... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Carboxylic acid.Primary amine | Secondary amine | null | null | c1ccccc1 | HO- | C(C)O | null | null | CN.O=C(O)CC(=O)O.O=Cc1cccc(O)c1>C(C)O>CNC(CC(=O)O)c1cccc(O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b897c681614b41c69f2c1fde9b55d1b8 | CCO.CNC(CC(=O)O)c1cccc(O)c1>>CCOC(=O)CC(NC)c1cccc(O)c1 | OC=1C=C(C=CC1)C(CC(=O)O)NC.C(C)O.S(O)(O)(=O)=O.C(O)([O-])=O.[Na+]>>OC=1C=C(C=CC1)C(CC(=O)OCC)NC | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])[CH2:6][CH:7]([NH:8][CH3:9])[c:10]1[cH:11][cH:12][cH:13][c:14]([OH:15])[cH:16]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]([NH:8][CH3:9])[c:10]1[cH:11][cH:12][cH:13][c:14]([OH:15])[cH:16]1 | CCO.CNC(CC(=O)O)c1cccc(O)c1 | CCOC(=O)CC(NC)c1cccc(O)c1 | null | null | null | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C;D1;H3:5]-[C:6]-[OH;D1;+0:7]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C:6]-[C;D1;H3:5] | null | [] | null | null | null | null | 3-(3-Hydroxyphenyl)-3-methylaminopropionic acid (24.1 g) obtained from Example 7a was dissolved in ethanol (200 ml), and concentrated sulfuric acid (10 ml) was added dropwise to the solution. The resulting mixture was heated under reflux for 8 hours. The reaction mixture was neutralized with saturated aqueous sodium hy... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1 | HO- | null | null | null | CCO.CNC(CC(=O)O)c1cccc(O)c1>>CCOC(=O)CC(NC)c1cccc(O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-09cd046db230433b8368956f66f69cbd | BrCc1ccccc1.CCOC(=O)CC(c1ccc(O)cc1)N(C)C(=O)OC(C)(C)C>>CCOC(=O)CC(c1ccc(OCc2ccccc2)cc1)N(C)C(=O)OC(C)(C)C | C(C1=CC=CC=C1)Br.C(C)(C)(C)OC(=O)N(C)C(CC(=O)OCC)C1=CC=C(C=C1)O.C([O-])([O-])=O.[K+].[K+]>>C(C1=CC=CC=C1)OC1=CC=C(C=C1)C(CC(=O)OCC)N(C)C(=O)OC(C)(C)C | Br[CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]([c:8]1[cH:9][cH:10][c:11]([OH:12])[cH:20][cH:21]1)[N:22]([CH3:23])[C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]([c:8]1[cH:9][cH:10][c:11]([O:12][CH2:13][c:14]2[cH:... | BrCc1ccccc1.CCOC(=O)CC(c1ccc(O)cc1)N(C)C(=O)OC(C)(C)C | CCOC(=O)CC(c1ccc(OCc2ccccc2)cc1)N(C)C(=O)OC(C)(C)C | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(COc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8] | 84.2 | [{"value": 84.2, "product": "C(C1=CC=CC=C1)OC1=CC=C(C=C1)C(CC(=O)OCC)N(C)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | N,N-Dimethylformamide and benzyl bromide (2.3 ml, 19 mmol) were added sequentially to ethyl 3-[N-(t-butoxy carbonyl)-N-methylamino]-3-(4-hydroxyphenyl)propionate (5.10 g, 16 mmol) obtained from Example 16a and potassium carbonate (3.27 g, 24 mmol) and the mixture was stirred at room temperature for 4 hours. The reactio... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HBr | CN(C=O)C | null | 4 | BrCc1ccccc1.CCOC(=O)CC(c1ccc(O)cc1)N(C)C(=O)OC(C)(C)C>CN(C=O)C>CCOC(=O)CC(c1ccc(OCc2ccccc2)cc1)N(C)C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b92fe907f400444cae424896cd8e1249 | CCOC(=O)CC(c1ccc(OCc2ccccc2)cc1)N(C)C(=O)OC(C)(C)C>>CN(C(=O)OC(C)(C)C)C(CCO)c1ccc(OCc2ccccc2)cc1 | S(=O)(=O)([O-])[O-].[Mg+2].[OH-].[Na+].C(C1=CC=CC=C1)OC1=CC=C(C=C1)C(CC(=O)OCC)N(C)C(=O)OC(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>C(C1=CC=CC=C1)OC1=CC=C(C=C1)C(CCO)N(C(OC(C)(C)C)=O)C | CCO[C:12]([CH2:11][CH:10]([N:2]([CH3:1])[C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])[c:14]1[cH:15][cH:16][c:17]([O:18][CH2:19][c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[cH:26][cH:27]1)=[O:13]>>[CH3:1][N:2]([C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])[CH:10]([CH2:11][CH2:12][OH:13])[c:14]1[cH:15][cH:16][c:17... | CCOC(=O)CC(c1ccc(OCc2ccccc2)cc1)N(C)C(=O)OC(C)(C)C | CN(C(=O)OC(C)(C)C)C(CCO)c1ccc(OCc2ccccc2)cc1 | null | null | O1CCCC1.O | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(COc2ccccc2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[C:4]>>[C:4]-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2] | 99 | [{"value": 99.0, "product": "C(C1=CC=CC=C1)OC1=CC=C(C=C1)C(CCO)N(C(OC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | Tetrahydrofuran (100 ml) was added to lithium aluminum hydride (1.02 g, 27 mmol) under an atmosphere of nitrogen, and a solution of ethyl 3-(4-benzyloxyphenyl)-3-[N-(t-butoxycarbonyl)-N-methylamino]propionate (5.56 g, 13 mmol) obtained from Example 115a in tetrahydrofuran was slowly added thereto at −78° C. After stirr... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.c1ccccc1 | HO- | O1CCCC1.O | 0 | 0.5 | CCOC(=O)CC(c1ccc(OCc2ccccc2)cc1)N(C)C(=O)OC(C)(C)C>O1CCCC1.O>CN(C(=O)OC(C)(C)C)C(CCO)c1ccc(OCc2ccccc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4865a31e56cf4b4aa01dcc9e2a2e5b03 | CN(C(=O)OC(C)(C)C)C(CCO)c1ccc(OCc2ccccc2)cc1.[C-]#N>>CN(C(=O)OC(C)(C)C)C(CCC#N)c1ccc(OCc2ccccc2)cc1 | C1COCCOCCOCCOCCO1.C(C1=CC=CC=C1)OC1=CC=C(C=C1)C(CCO)N(C(OC(C)(C)C)=O)C.C(C)N(CC)CC.[C-]#N.[Na+].CS(=O)(=O)Cl>>C(C1=CC=CC=C1)OC1=CC=C(C=C1)C(CCC#N)N(C(OC(C)(C)C)=O)C | O[CH2:12][CH2:11][CH:10]([N:2]([CH3:1])[C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])[c:15]1[cH:16][cH:17][c:18]([O:19][CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[cH:27][cH:28]1.[C-:13]#[N:14]>>[CH3:1][N:2]([C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])[CH:10]([CH2:11][CH2:12][C:13]#[N:14])[c:15]1[cH:16]... | CN(C(=O)OC(C)(C)C)C(CCO)c1ccc(OCc2ccccc2)cc1.[C-]#N | CN(C(=O)OC(C)(C)C)C(CCC#N)c1ccc(OCc2ccccc2)cc1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | a1e85c1b3a4aa1231f3779c2baa8b6951b270c05216d065e2aa7ce489240e0a5 | 1d32632fcc69ac04f0b8d96dc5305dd07d5339ab86bfe9a364cefb5e65c6d5b1 | c1ccc(COc2ccccc2)cc1 | O-[CH2;D2;+0:1]-[C:2]-[C:3].[C-;H0;D1:4]#[N;D1;H0:5]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[C;H0;D2;+0:4]#[N;D1;H0:5] | 92.6 | [{"value": 92.6, "product": "C(C1=CC=CC=C1)OC1=CC=C(C=C1)C(CCC#N)N(C(OC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | t-Butyl N-[1-(4-benzyloxyphenyl)-3-hydroxypropyl]-N-methylcarbamate (1.50 g, 4.0 mmol) obtained from Example 115b was dissolved in tetrahydrofuran (20 ml) under an atmosphere of nitrogen. To the solution was added triethylamine (0.84 ml, 6.0 mmol) and then methanesulfonyl chloride (0.37 ml, 4.8 mmol), in an ice bath. T... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Nitrile | null | null | c1ccccc1.c1ccccc1 | HO- | O1CCCC1 | null | 0.5 | CN(C(=O)OC(C)(C)C)C(CCO)c1ccc(OCc2ccccc2)cc1.[C-]#N>O1CCCC1>CN(C(=O)OC(C)(C)C)C(CCC#N)c1ccc(OCc2ccccc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6a53a751ab524748af8c6310aa31bddb | CN(C(=O)OC(C)(C)C)C(CCC#N)c1ccc(OCc2ccccc2)cc1>>CN(C(=O)OC(C)(C)C)C(CCCO)c1ccc(OCc2ccccc2)cc1 | [H-].C(C(C)C)[Al+]CC(C)C.CCCCCC.[BH4-].[Na+].S(=O)(=O)([O-])[O-].[Na+].[Na+].C(C1=CC=CC=C1)OC1=CC=C(C=C1)C(CCC#N)N(C(OC(C)(C)C)=O)C>>C(C1=CC=CC=C1)OC1=CC=C(C=C1)C(CCCO)N(C(OC(C)(C)C)=O)C | N#[C:13][CH2:12][CH2:11][CH:10]([N:2]([CH3:1])[C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])[c:15]1[cH:16][cH:17][c:18]([O:19][CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[cH:27][cH:28]1>>[CH3:1][N:2]([C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])[CH:10]([CH2:11][CH2:12][CH2:13][OH:14])[c:15]1[cH:16][cH:17... | CN(C(=O)OC(C)(C)C)C(CCC#N)c1ccc(OCc2ccccc2)cc1 | CN(C(=O)OC(C)(C)C)C(CCCO)c1ccc(OCc2ccccc2)cc1 | null | null | ClCCl.O | Functional Group Interconversion | OtherReaction | dfa6aab906f1cce8c060c3454d617eee54109b7fbe31f54f7240a7e17e9d9a0b | cfcea505f43817e62057efa9fa83f3ef47a11a99a8a6ad13903bd9b247dfd586 | c1ccc(COc2ccccc2)cc1 | N#[C;H0;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;D1;H1:4] | 82.8 | [{"value": 82.8, "product": "C(C1=CC=CC=C1)OC1=CC=C(C=C1)C(CCCO)N(C(OC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | t-Butyl N-(1-(4-benzyloxyphenyl)-3-cyanopropyl]-N-methylcarbamate (1.00 g, 2.6 mmol) obtained from Example 115c was dissolved in dichloromethane (20 ml) under an atmosphere of nitrogen. To the solution was added 0.95 M solution of diisobutylaluminum hydride in hexane (5.5 ml, 5.3 mmol) at −78° C. and the temperature wa... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary alcohol | null | null | c1ccccc1.c1ccccc1 | null | ClCCl.O | null | 2 | CN(C(=O)OC(C)(C)C)C(CCC#N)c1ccc(OCc2ccccc2)cc1>ClCCl.O>CN(C(=O)OC(C)(C)C)C(CCCO)c1ccc(OCc2ccccc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-29c0a67898714954aa642928cf67596e | CCOC(=O)C=C1NCCc2cc(OC)ccc21>>CCOC(=O)CC1NCCc2cc(OC)ccc21 | COC=1C=C2CCNC(C2=CC1)=CC(=O)OCC.[OH-].[Na+].C([O-])([O-])=O.[K+].[K+]>>COC=1C=C2CCNC(C2=CC1)CC(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[C:7]1[NH:8][CH2:9][CH2:10][c:11]2[cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17][c:18]21>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]1[NH:8][CH2:9][CH2:10][c:11]2[cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17][c:18]21 | CCOC(=O)C=C1NCCc2cc(OC)ccc21 | CCOC(=O)CC1NCCc2cc(OC)ccc21 | null | [Pt]=O | C(C)(=O)O | Reduction | Hydrogenation (double to single) | a2a16c1a99dc53e406de229794c537c379a76e9a646517a7c8ab052fadff31d4 | b586296faf9080b398947dcba4825d3daf71a75997a309df19187f20bff3e49d | c1ccc2c(c1)CCNC2 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D2;+0:5]=[C;H0;D3;+0:6](-[#7:7]-[C:8])-[c:9](:[c:10]):[c:11]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[CH;D3;+0:6](-[#7:7]-[C:8])-[c:9](:[c:10]):[c:11] | 64 | [{"value": 64.0, "product": "COC=1C=C2CCNC(C2=CC1)CC(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of ethyl (6-methoxy-3,4-dihydro-2H-isoquinolin-1-yliden)-acetate (7.56 g) obtained in step (b) of Example 187 in acetic acid (50 ml) was added platinum oxide (400 mg), and the resulting mixture was stirred for 3 hours at room temperature under a hydrogen atmosphere. After stirring, the reaction mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Enamine | Ester | c1ccc2c(c1)CCNC2 | c1ccc2c(c1)CCNC2 | c1ccc2c(c1)CCNC2 | null | [Pt]=O.C(C)(=O)O | null | 3 | CCOC(=O)C=C1NCCc2cc(OC)ccc21>[Pt]=O.C(C)(=O)O>CCOC(=O)CC1NCCc2cc(OC)ccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5eb99a98074542cdac0a1b8b4ef922f8 | CCOC(=O)CC1c2ccc(O)cc2CCN1C(=O)OC(C)(C)C.CN(C)C(=O)Cl.O>>CCOC(=O)CC1C2=C(CCN1C(=O)OC(C)(C)C)CC(O)(OC(=O)N(C)C)C=C2 | O.C(C)OC(=O)CC1N(CCC2=CC(=CC=C12)O)C(=O)OC(C)(C)C.C([O-])([O-])=O.[K+].[K+].CN(C(=O)Cl)C>>CN(C(=O)OC1(CC=2CCN(C(C2C=C1)CC(=O)OCC)C(=O)OC(C)(C)C)O)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]1[c:8]2[c:9]([cH:20][c:21]([OH:22])[cH:29][cH:30]2)[CH2:10][CH2:11][N:12]1[C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19].Cl[C:24](=[O:25])[N:26]([CH3:27])[CH3:28].[OH2:23]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]1[C:8]2=[C:9]([CH2:10][CH2:11][N:12]1[C:13](=[O:... | CCOC(=O)CC1c2ccc(O)cc2CCN1C(=O)OC(C)(C)C.CN(C)C(=O)Cl.O | CCOC(=O)CC1C2=C(CCN1C(=O)OC(C)(C)C)CC(O)(OC(=O)N(C)C)C=C2 | null | null | CN(C=O)C | Protection | OtherReaction | 6d2f16630df4090cd3c58cd2f34abacbdfcd8c38c0b22f845df91da04096e9d8 | 8113e1af9c36bbe7fed7499330e4e08640ab6a60502ef3feb1a2935ccf85500c | C1=CC2=C(CC1)CCNC2 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C;D1;H3:4])-[C;D1;H3:5].[#8:6]-[C:7](=[O;D1;H0:8])-[C:9]-[C:10]1-[#7:11](-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15](-[C;D1;H3:16])(-[C;D1;H3:17])-[C;D1;H3:18])-[C:19]-[C:20]-[c;H0;D3;+0:21]2:[cH;D2;+0:22]:[c;H0;D3;+0:23](-[O;D1;H1:24]):[cH;D2;+0:25]:[cH;D2;+0:26]:[c;H0;D3;+0:27]:2-1.... | 95 | [{"value": 95.0, "product": "CN(C(=O)OC1(CC=2CCN(C(C2C=C1)CC(=O)OCC)C(=O)OC(C)(C)C)O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.5, "product": "CN(C(=O)OC1(CC=2CCN(C(C2C=C1)CC(=O)OCC)C(=O)OC(C)(C)C)O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | To a solution of t-butyl 1-ethoxycarbonylmethyl-6-hydroxy-3,4-dihydro-1H-isoquinoline-2-carboxylate (1.70 g, 5.07 mmol) synthesized in step (d) of Example 187 in dimethylformamide (5 ml) were added potassium carbonate (1.03 g, 7.50 mmol) and N,N-dimethylcarbamoyl chloride (0.69 ml, 7.5 mmol), and the resulting mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Aromatic alcohol | Carbamic ester.Ether.Tertiary alcohol | c1ccc2c(c1)CC[NH]C2 | C1=CC2=C(CC1)CC[NH]C2 | C1=CC2=C(CC1)CC[NH]C2 | HCl | CN(C=O)C | null | 2.5 | CCOC(=O)CC1c2ccc(O)cc2CCN1C(=O)OC(C)(C)C.CN(C)C(=O)Cl.O>CN(C=O)C>CCOC(=O)CC1C2=C(CCN1C(=O)OC(C)(C)C)CC(O)(OC(=O)N(C)C)C=C2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5ee0d5ca84fa442b95a5077f94c19046 | CCOC(=O)CC1C2=C(CCN1C(=O)OC(C)(C)C)CC(O)(OC(=O)N(C)C)C=C2>>CN(C)C(=O)Oc1ccc2c(c1)CCN(C(=O)OC(C)(C)C)C2CCO | CN(C(=O)OC1(CC=2CCN(C(C2C=C1)CC(=O)OCC)C(=O)OC(C)(C)C)O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+].O>>CN(C(=O)OC=1C=C2CCN(C(C2=CC1)CCO)C(=O)OC(C)(C)C)C | CCO[C:25]([CH2:24][CH:23]1[C:10]2=[C:11]([CH2:12][C:7](O)([O:6][C:4]([N:2]([CH3:1])[CH3:3])=[O:5])[CH:8]=[CH:9]2)[CH2:13][CH2:14][N:15]1[C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:26]>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[O:6][c:7]1[cH:8][cH:9][c:10]2[c:11]([cH:12]1)[CH2:13][CH2:14][N:15]([C:16](=[O:17])[... | CCOC(=O)CC1C2=C(CCN1C(=O)OC(C)(C)C)CC(O)(OC(=O)N(C)C)C=C2 | CN(C)C(=O)Oc1ccc2c(c1)CCN(C(=O)OC(C)(C)C)C2CCO | null | null | O1CCCC1 | Reduction | OtherReaction | 3853f56c6f0ecde368d58bc22fc3494232d8f07bad3b0cd3580c749ca6f02671 | f97908a80f5a6be714b164c5d0248e40307dea320152935297423c15a42639b6 | c1ccc2c(c1)CCNC2 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[C:4]1-[#7:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C:13]-[C:14]-[C;H0;D3;+0:15]2=[C;H0;D3;+0:16]-1-[CH;D2;+0:17]=[CH;D2;+0:18]-[C;H0;D4;+0:19](-O)(-[#8:20]-[C:21](-[#7:22])=[O;D1;H0:23])-[CH2;D2;+0:24]-2>>[#7:22]-[C:21](=[O;D1;H0:23])... | 78.2 | [{"value": 78.0, "product": "CN(C(=O)OC=1C=C2CCN(C(C2=CC1)CCO)C(=O)OC(C)(C)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.2, "product": "CN(C(=O)OC=1C=C2CCN(C(C2=CC1)CCO)C(=O)OC(C)(C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 20 | MINUTE | To a solution of t-butyl 6-dimethylcarbamoyloxy-1-ethoxycarbonylmethyl-6-hydroxy-3,4-dihydro-1H-isoquinoline-2-carboxylate (1.97 g, 4.84 mmol) synthesized in step (e) of Example 187 in tetrahydrofuran (30 ml) was added lithium aluminum hydride (270 mg, 7.2 mmol) at −78° C., and the resulting mixture was stirred for 20 ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Tertiary alcohol | Ether.Primary alcohol | C1=CC2=C(CC1)CC[NH]C2 | c1ccc2c(c1)CC[NH]C2 | c1ccc2c(c1)CC[NH]C2 | HO- | O1CCCC1 | 0 | 0.333333 | CCOC(=O)CC1C2=C(CCN1C(=O)OC(C)(C)C)CC(O)(OC(=O)N(C)C)C=C2>O1CCCC1>CN(C)C(=O)Oc1ccc2c(c1)CCN(C(=O)OC(C)(C)C)C2CCO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1efe1a17e254476f9a9f287ffa575637 | COc1ccc2c(c1)CCN[C@@H]2CCO[Si](C)(C)C(C)(C)C>>COc1ccc2c(c1)CCN[C@@H]2CCO | COC=1C=C2CCN[C@@H](C2=CC1)CCO[Si](C)(C)C(C)(C)C.FC(C(=O)N)(F)F.F.O.C(O)([O-])=O.[Na+]>>COC=1C=C2CCN[C@@H](C2=CC1)CCO.FC(C(=O)N)(F)F | CC(C)(C)[Si](C)(C)[O:15][CH2:14][CH2:13][C@@H:12]1[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8][c:7]2[CH2:9][CH2:10][NH:11]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][NH:11][C@@H:12]2[CH2:13][CH2:14][OH:15] | COc1ccc2c(c1)CCN[C@@H]2CCO[Si](C)(C)C(C)(C)C | COc1ccc2c(c1)CCN[C@@H]2CCO | null | null | C(C)#N | Deprotection | Alcohol deprotection from silyl ethers | 6ff8c9c41093ab5237b871dd4689ba6431022d615e227d3774901a983c846e4b | 84d9f5b4e7757c58e584c26c7d52c9a3f594fbcb0c0d22f34765a93a932fcd5b | c1ccc2c(c1)CCNC2 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[OH;D1;+0:1] | 79 | [{"value": 79.0, "product": "COC=1C=C2CCN[C@@H](C2=CC1)CCO.FC(C(=O)N)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.3, "product": "COC=1C=C2CCN[C@@H](C2=CC1)CCO.FC(C(=O)N)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 6-methoxy-1-(R)-(2-t-butyldimethylsilyloxyethyl)-3,4-dihydro-1H-isoquinoline-trifluoroacetamide (1.14 g, 2.73 mmol) obtained in step (a) of Example 190 in acetonitrile (10 ml) was added dropwise 48% solution of hydrofluoric acid in water (0.5 ml, 13.67 mmol) gradually with stirring under cooling in a w... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Primary alcohol | null | null | c1ccc2c(c1)CCNC2 | Other | C(C)#N | null | null | COc1ccc2c(c1)CCN[C@@H]2CCO[Si](C)(C)C(C)(C)C>C(C)#N>COc1ccc2c(c1)CCN[C@@H]2CCO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-63b2bb6424aa48788cdfc3e41900a2da | COc1ccc2c(c1)CCN[C@@H]2CCBr>>Oc1ccc2c(c1)CCN[C@@H]2CCBr | C(O)([O-])=O.[Na+].COC=1C=C2CCN[C@@H](C2=CC1)CCBr.FC(C(=O)N)(F)F.B(Br)(Br)Br>>OC=1C=C2CCN[C@@H](C2=CC1)CCBr.FC(C(=O)N)(F)F | C[O:8][c:9]1[cH:10][cH:11][c:12]2[c:13]([cH:14]1)[CH2:15][CH2:16][NH:17][C@@H:18]2[CH2:19][CH2:20][Br:21]>>[OH:8][c:9]1[cH:10][cH:11][c:12]2[c:13]([cH:14]1)[CH2:15][CH2:16][NH:17][C@@H:18]2[CH2:19][CH2:20][Br:21] | COc1ccc2c(c1)CCN[C@@H]2CCBr | Oc1ccc2c(c1)CCN[C@@H]2CCBr | null | null | ClCCl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc2c(c1)CCNC2 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 75 | [{"value": 75.0, "product": "OC=1C=C2CCN[C@@H](C2=CC1)CCBr.FC(C(=O)N)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.9, "product": "OC=1C=C2CCN[C@@H](C2=CC1)CCBr.FC(C(=O)N)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 6-methoxy-1-(R)-(2-bromoethyl)-3,4-dihydro-1H-isoquinoline-trifluoroacetamide (390 mg, 1.07 mmol) obtained in step (c) of Example 190 in dichloromethane (5 ml) was added 1M solution of boron tribromide in dichloromethane (2.14 ml, 2.14 mmol) gradually at −78° C. with stirring. The resulting mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccc2c(c1)CCNC2 | Other | ClCCl | null | null | COc1ccc2c(c1)CCN[C@@H]2CCBr>ClCCl>Oc1ccc2c(c1)CCN[C@@H]2CCBr |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d1e44508a28c4bb09872267ad0a0e331 | CN(C)C(=O)Cl.Oc1ccc2c(c1)CCN[C@@H]2CCBr>>CN(C)C(=O)Oc1ccc2c(c1)CCN[C@@H]2CCBr | O.OC=1C=C2CCN[C@@H](C2=CC1)CCBr.FC(C(=O)N)(F)F.C([O-])([O-])=O.[K+].[K+].CN(C(=O)Cl)C>>CN(C(=O)OC=1C=C2CCN[C@@H](C2=CC1)CCBr)C.FC(C(=O)N)(F)F | Cl[C:4]([N:2]([CH3:1])[CH3:3])=[O:5].[OH:6][c:7]1[cH:8][cH:9][c:10]2[c:11]([cH:12]1)[CH2:13][CH2:14][NH:15][C@@H:16]2[CH2:17][CH2:18][Br:19]>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[O:6][c:7]1[cH:8][cH:9][c:10]2[c:11]([cH:12]1)[CH2:13][CH2:14][NH:15][C@@H:16]2[CH2:17][CH2:18][Br:19] | CN(C)C(=O)Cl.Oc1ccc2c(c1)CCN[C@@H]2CCBr | CN(C)C(=O)Oc1ccc2c(c1)CCN[C@@H]2CCBr | null | null | CN(C=O)C | Protection | Schotten-Baumann to ester | 76fc23af07d8d02fec539138b5d326dfd4e833212bae1d173120f54983c8b7d8 | 4c7d92b589147a4e2aa8407ff52bd0eb1be84bdb6595779d27beb0c5d6fdd0e2 | c1ccc2c(c1)CCNC2 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C;D1;H3:4])-[C;D1;H3:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:4]-[#7:3](-[C;D1;H3:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | 52 | [{"value": 52.0, "product": "CN(C(=O)OC=1C=C2CCN[C@@H](C2=CC1)CCBr)C.FC(C(=O)N)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.1, "product": "CN(C(=O)OC=1C=C2CCN[C@@H](C2=CC1)CCBr)C.FC(C(=O)N)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 6-hydroxy-1-(R)-(2-bromoethyl)-3,4-dihydro-1H-isoquinoline-trifluoroacetamide (270 mg, 0.77 mmol) obtained in step (d) of Example 190 and potassium carbonate (268 mg, 1.94 mmol) in dimethylformamide (3 ml) was added dimethylcarbamyl chloride (0.2 ml, 1.55 mmol) gradually with stirring under cooling in ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Aromatic alcohol | Carbamic ester | null | null | c1ccc2c(c1)CCNC2 | HCl | CN(C=O)C | null | null | CN(C)C(=O)Cl.Oc1ccc2c(c1)CCN[C@@H]2CCBr>CN(C=O)C>CN(C)C(=O)Oc1ccc2c(c1)CCN[C@@H]2CCBr |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-81666d7f3ef14453a6c682b08a4b2d3b | CN(C)C(=O)Oc1ccc2c(c1)CCN[C@@H]2CCBr.Cc1cc(O)ccc1Cl>>Cc1cc(OCC[C@H]2NCCc3cc(OC(=O)N(C)C)ccc32)ccc1Cl | C([O-])([O-])=O.[K+].[K+].[I-].[K+].ClC=1C(=CC(=CC1)O)C.CN(C(=O)OC=1C=C2CCN[C@@H](C2=CC1)CCBr)C.FC(C(=O)N)(F)F>>FC(C(=O)N)(F)F.CN(C(=O)OC=1C=C2CCN[C@@H](C2=CC1)CCOC1=CC(=C(C=C1)Cl)C)C | Br[CH2:6][CH2:7][C@H:8]1[NH:9][CH2:10][CH2:11][c:12]2[cH:13][c:14]([O:15][C:16](=[O:17])[N:18]([CH3:19])[CH3:20])[cH:21][cH:22][c:23]21.[CH3:1][c:2]1[cH:3][c:4]([OH:5])[cH:24][cH:25][c:26]1[Cl:27]>>[CH3:1][c:2]1[cH:3][c:4]([O:5][CH2:6][CH2:7][C@H:8]2[NH:9][CH2:10][CH2:11][c:12]3[cH:13][c:14]([O:15][C:16](=[O:17])[N:18]... | CN(C)C(=O)Oc1ccc2c(c1)CCN[C@@H]2CCBr.Cc1cc(O)ccc1Cl | Cc1cc(OCC[C@H]2NCCc3cc(OC(=O)N(C)C)ccc32)ccc1Cl | null | null | O.CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(OCC[C@H]2NCCc3ccccc32)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[#7:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[#7:4]-[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8] | 84 | [{"value": 84.0, "product": "FC(C(=O)N)(F)F.CN(C(=O)OC=1C=C2CCN[C@@H](C2=CC1)CCOC1=CC(=C(C=C1)Cl)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.7, "product": "FC(C(=O)N)(F)F.CN(C(=O)OC=1C=C2CCN[C@@H](C2=CC1)CCOC1=CC(=C(C=C1)Cl)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of potassium carbonate (115 mg, 0.83 mmol), potassium iodide (catalytic amount) and 4-chloro-m-cresol (65 mg, 0.46 mmol) in dimethylformamide (2 ml) was added a solution of 6-dimethylcarbamoyloxy-1-(R)-(2-bromoethyl)-3,4-dihydro-1H-isoquinoline-trifluoroacetamide (160 mg, 0.38 mmol) obtained in step (e) o... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccc2c(c1)CCNC2 | HBr | O.CN(C=O)C | null | null | CN(C)C(=O)Oc1ccc2c(c1)CCN[C@@H]2CCBr.Cc1cc(O)ccc1Cl>O.CN(C=O)C>Cc1cc(OCC[C@H]2NCCc3cc(OC(=O)N(C)C)ccc32)ccc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-29aa1a9678cd44989c0fb030e2ab7175 | CN(C)C(=O)Cl.O=Cc1ccc(O)cc1O>>CN(C)C(=O)Oc1ccc(C=O)c(O)c1 | [H-].[Na+].OC1=C(C=O)C=CC(=C1)O.CN(C(=O)Cl)C>>CN(C(OC1=CC(=C(C=C1)C=O)O)=O)C | Cl[C:4]([N:2]([CH3:1])[CH3:3])=[O:5].[OH:6][c:7]1[cH:8][cH:9][c:10]([CH:11]=[O:12])[c:13]([OH:14])[cH:15]1>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[O:6][c:7]1[cH:8][cH:9][c:10]([CH:11]=[O:12])[c:13]([OH:14])[cH:15]1 | CN(C)C(=O)Cl.O=Cc1ccc(O)cc1O | CN(C)C(=O)Oc1ccc(C=O)c(O)c1 | null | null | O | Protection | Schotten-Baumann to ester | 76fc23af07d8d02fec539138b5d326dfd4e833212bae1d173120f54983c8b7d8 | 4c7d92b589147a4e2aa8407ff52bd0eb1be84bdb6595779d27beb0c5d6fdd0e2 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C;D1;H3:4])-[C;D1;H3:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:4]-[#7:3](-[C;D1;H3:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | 30 | [{"value": 30.0, "product": "CN(C(OC1=CC(=C(C=C1)C=O)O)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 29.7, "product": "CN(C(OC1=CC(=C(C=C1)C=O)O)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of sodium hydride (5.74 g, 239 mmol), which was prepared free from mineral oil by washing with hexane, in dimethylformamide (100 ml) was added 2,4-dihydroxybenzaldehyde (15.0 g, 109 mmol) at 0° C. with stirring, and the resulting mixture was stirred for 30 minutes at 0° C. under a nitrogen atmosphere. S... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Aromatic alcohol | Carbamic ester | null | null | c1ccccc1 | HCl | O | null | null | CN(C)C(=O)Cl.O=Cc1ccc(O)cc1O>O>CN(C)C(=O)Oc1ccc(C=O)c(O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2dbee7a0197c46ba8a7ac5f01fbb9607 | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.CN(C)C(=O)Oc1ccc(C=O)c(OS(=O)(=O)C(F)(F)F)c1>>C=Cc1cc(OC(=O)N(C)C)ccc1C=O | [F-].[K+].FC(S(=O)(=O)OC1=C(C=CC(=C1)OC(N(C)C)=O)C=O)(F)F.[Cl-].[Li+].C(CCC)[Sn](C=C)(CCCC)CCCC>>CN(C(OC1=CC(=C(C=C1)C=O)C=C)=O)C | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH:2]=[CH2:1].O=S(=O)(O[c:3]1[cH:4][c:5]([O:6][C:7](=[O:8])[N:9]([CH3:10])[CH3:11])[cH:12][cH:13][c:14]1[CH:15]=[O:16])C(F)(F)F>>[CH2:1]=[CH:2][c:3]1[cH:4][c:5]([O:6][C:7](=[O:8])[N:9]([CH3:10])[CH3:11])[cH:12][cH:13][c:14]1[CH:15]=[O:16] | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.CN(C)C(=O)Oc1ccc(C=O)c(OS(=O)(=O)C(F)(F)F)c1 | C=Cc1cc(OC(=O)N(C)C)ccc1C=O | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C(C)(C)(C)C1=C(C(=CC=C1)C(C)(C)C)O | O1CCOCC1 | C-C Coupling | Stille reaction_vinyl OTf | 19b30501d1aaa5f5dd56b13112130366c0e45d6c2d2ca2c3e4e656b3de7ef26d | 22963776d86934928a954d267e6c7c5a64095fcc3303c473fde6e3c4d4878a47 | c1ccccc1 | C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[CH;D2;+0:1]=[C;D1;H2:2].F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6](-[C:7]=[O;D1;H0:8]):[c:9]>>[C;D1;H2:2]=[CH;D2;+0:1]-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6](-[C:7]=[O;D1;H0:8]):[c:9] | 79.5 | [{"value": 79.0, "product": "CN(C(OC1=CC(=C(C=C1)C=O)C=C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.5, "product": "CN(C(OC1=CC(=C(C=C1)C=O)C=C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5-dimethylcarbamoyloxy-2-formyl-phenyl trifluoromethanesulfonate (4.13 g, 12.1 mmol) obtained in step (b) of Example 192 in 1,4-dioxane (15 ml) were added tetrakis(triphenylphosphine)palladium (693 mg, 0.600 mmol), 2,6-di-t-butylphenol (5 mg), lithium chloride (1.54 g, 36.4 mmol) and tributyl(vinyl)tin... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Vinyl.Tin | Vinyl | c1ccccc1 | c1ccccc1 | c1ccccc1 | TfOH.HO-.Sn | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C(C)(C)(C)C1=C(C(=CC=C1)C(C)(C)C)O.O1CCOCC1 | null | null | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.CN(C)C(=O)Oc1ccc(C=O)c(OS(=O)(=O)C(F)(F)F)c1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C(C)(C)(C)C1=C(C(=CC=C1)C(C)(C)C)O.O1CCOCC1>C=Cc1cc(OC(=O)N(C)C)c... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-047ca800aac440949d4d9c975a0f411c | C=Cc1cc(OC(=O)N(C)C)ccc1C=O.CCOC(C)=O>>C=Cc1cc(OC(=O)N(C)C)ccc1C(O)CC(=O)OCC | CN(C(OC1=CC(=C(C=C1)C=O)C=C)=O)C.[Cl-].[NH4+].C(C)(C)NC(C)C.C(CCC)[Li].CCCCCC.C(C)(=O)OCC>>CN(C(=O)OC1=CC(=C(C=C1)C(CC(=O)OCC)O)C=C)C | [CH2:1]=[CH:2][c:3]1[cH:4][c:5]([O:6][C:7](=[O:8])[N:9]([CH3:10])[CH3:11])[cH:12][cH:13][c:14]1[CH:15]=[O:16].[CH3:17][C:18](=[O:19])[O:20][CH2:21][CH3:22]>>[CH2:1]=[CH:2][c:3]1[cH:4][c:5]([O:6][C:7](=[O:8])[N:9]([CH3:10])[CH3:11])[cH:12][cH:13][c:14]1[CH:15]([OH:16])[CH2:17][C:18](=[O:19])[O:20][CH2:21][CH3:22] | C=Cc1cc(OC(=O)N(C)C)ccc1C=O.CCOC(C)=O | C=Cc1cc(OC(=O)N(C)C)ccc1C(O)CC(=O)OCC | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 5c727118385c562f285df4622fd28beee54f2a6dc613daeca0713283cec89087 | 12ce375342f37362e14813852abaca485261821306a77d2d6bbedf8a6a5866f3 | c1ccccc1 | [C;D1;H2:1]=[C:2]-[c:3]:[c:4](-[CH;D2;+0:5]=[O;H0;D1;+0:6]):[c:7].[C:8]-[#8:9]-[C:10](-[CH3;D1;+0:11])=[O;D1;H0:12]>>[C:8]-[#8:9]-[C:10](=[O;D1;H0:12])-[CH2;D2;+0:11]-[CH;D3;+0:5](-[OH;D1;+0:6])-[c:4](:[c:7]):[c:3]-[C:2]=[C;D1;H2:1] | 99.8 | [{"value": 99.0, "product": "CN(C(=O)OC1=CC(=C(C=C1)C(CC(=O)OCC)O)C=C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.8, "product": "CN(C(=O)OC1=CC(=C(C=C1)C(CC(=O)OCC)O)C=C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of diisopropylamine (1.26 g, 12.5 mmol) in tetrahydrofuran (30 ml) was added 1.6M solution of n-butyllithium in hexane (7.20 ml, 11.5 mmol) at −20° C. with stirring, and the resulting mixture was stirred for 20 minutes at −20° C. under a nitrogen atmosphere. Subsequently, ethyl acetate (1.07 ml, 11.0 mmol... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Ester.Secondary alcohol | null | null | c1ccccc1 | null | O1CCCC1 | null | null | C=Cc1cc(OC(=O)N(C)C)ccc1C=O.CCOC(C)=O>O1CCCC1>C=Cc1cc(OC(=O)N(C)C)ccc1C(O)CC(=O)OCC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e4ed07f7214b4021a98263981ed2fc2c | C=Cc1cc(OC(=O)N(C)C)ccc1C(O)CC(=O)OCC>>C=Cc1cc(OC(=O)N(C)C)ccc1C(O)CCO | O.Cl.CN(C(=O)OC1=CC(=C(C=C1)C(CC(=O)OCC)O)C=C)C.[BH4-].[Li+]>>CN(C(OC1=CC(=C(C=C1)C(CCO)O)C=C)=O)C | CCO[C:18]([CH2:17][CH:15]([c:14]1[c:3]([CH:2]=[CH2:1])[cH:4][c:5]([O:6][C:7](=[O:8])[N:9]([CH3:10])[CH3:11])[cH:12][cH:13]1)[OH:16])=[O:19]>>[CH2:1]=[CH:2][c:3]1[cH:4][c:5]([O:6][C:7](=[O:8])[N:9]([CH3:10])[CH3:11])[cH:12][cH:13][c:14]1[CH:15]([OH:16])[CH2:17][CH2:18][OH:19] | C=Cc1cc(OC(=O)N(C)C)ccc1C(O)CC(=O)OCC | C=Cc1cc(OC(=O)N(C)C)ccc1C(O)CCO | null | null | O1CCCC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[C:4]>>[C:4]-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2] | 97.3 | [{"value": 97.0, "product": "CN(C(OC1=CC(=C(C=C1)C(CCO)O)C=C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.3, "product": "CN(C(OC1=CC(=C(C=C1)C(CCO)O)C=C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of ethyl 3-(4-dimethylcarbamoyloxy-2-vinyl-phenyl)-3-hydroxy-propionate (5.28 g, 17.2 mmol) obtained in step (d) of Example 192 in tetrahydrofuran (50 ml) was added lithium tetrahydroborate (544 mg, 25.0 mmol) at −20° C. with stirring, and the reaction temperature was raised gradually to ambient temperatu... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1 | HO- | O1CCCC1 | null | null | C=Cc1cc(OC(=O)N(C)C)ccc1C(O)CC(=O)OCC>O1CCCC1>C=Cc1cc(OC(=O)N(C)C)ccc1C(O)CCO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-96b15e8c18704f68b411a33d85a9e40c | C=Cc1cc(OC(=O)N(C)C)ccc1C(O)CCO.CC(C)(C)[Si](C)(C)Cl.CCN(CC)CC>>C=Cc1cc(OC(=O)N(C)C)ccc1C(O)CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C | O.CN(C(OC1=CC(=C(C=C1)C(CCO)O)C=C)=O)C.C(C)N(CC)CC.C(C)(C)(C)[Si](Cl)(C)C>>CN(C(OC1=CC(=C(C=C1)C(CCO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)O)C=C)=O)C | [CH2:1]=[CH:2][c:3]1[cH:4][c:5]([O:6][C:7](=[O:8])[N:9]([CH3:10])[CH3:11])[cH:12][cH:13][c:14]1[CH:15]([OH:16])[CH2:17][CH2:18][OH:19].Cl[Si:20]([CH3:21])([CH3:27])[C:33]([CH3:34])([CH3:35])[CH3:36].N([CH2:22][CH3:25])([CH2:29][CH3:30])[CH2:32][CH3:31]>>[CH2:1]=[CH:2][c:3]1[cH:4][c:5]([O:6][C:7](=[O:8])[N:9]([CH3:10])[... | C=Cc1cc(OC(=O)N(C)C)ccc1C(O)CCO.CC(C)(C)[Si](C)(C)Cl.CCN(CC)CC | C=Cc1cc(OC(=O)N(C)C)ccc1C(O)CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C | null | CN(C1=CC=NC=C1)C | ClCCl | Aromatic Heterocycle Formation | OtherReaction | 500aab33a5fdae74a8362d9d6c793395a5801abb4ca2c4d3e1d2b2517e0a3aef | 9209b2acefe19f140772464284a8330dc3debcbdc34c49c2add1f0a0e951600b | c1ccc(CCCO[SiH](c2ccccc2)c2ccccc2)cc1 | Cl-[Si;H0;D4;+0:1](-[CH3;D1;+0:2])(-[CH3;D1;+0:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[CH3;D1;+0:8]-[CH2;D2;+0:9]-N(-[CH2;D2;+0:10]-[CH3;D1;+0:11])-[CH2;D2;+0:12]-[CH3;D1;+0:13].[C:14]-[C:15]-[OH;D1;+0:16]>>[C:14]-[C:15]-[O;H0;D2;+0:16]-[Si;H0;D4;+0:1](-[c;H0;D3;+0:2]1:[c:17]:[cH;D2;+0:8]:[c:18]:[c:19]:[cH;D... | 139.6 | [{"value": 70.0, "product": "CN(C(OC1=CC(=C(C=C1)C(CCO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)O)C=C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 139.6, "product": "CN(C(OC1=CC(=C(C=C1)C(CCO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)O)C=C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | To a solution of 4-(1,3-dihydroxy-propyl)-3-vinyl-phenyl dimethylcarbamate (4.44 g, 16.7 mmol) synthesized in step (e) of Example 192 in dichloromethane (40 ml) were added triethylamine (4.18 ml, 30.0 mmol), t-butyldimethylchlorosilane (4.67 g, 17.0 mmol) and a catalytic amount of 4-dimethylaminopyridine at −0° C. with... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Tertiary amine.Silyl protective group | Silyl protective group | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | HCl | CN(C1=CC=NC=C1)C.ClCCl | null | 5 | C=Cc1cc(OC(=O)N(C)C)ccc1C(O)CCO.CC(C)(C)[Si](C)(C)Cl.CCN(CC)CC>CN(C1=CC=NC=C1)C.ClCCl>C=Cc1cc(OC(=O)N(C)C)ccc1C(O)CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-294bb25f02364fc6a9729d57a284d748 | BrC(Br)(Br)Br.C=Cc1cc(OC(=O)N(C)C)ccc1C(O)CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C>>C=Cc1cc(OC(=O)N(C)C)ccc1C(O)(Br)CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C | CN(C(OC1=CC(=C(C=C1)C(CCO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)O)C=C)=O)C.C(Br)(Br)(Br)Br.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>CN(C(OC1=CC(=C(C=C1)C(CCO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)(O)Br)C=C)=O)C | BrC(Br)(Br)[Br:17].[CH2:1]=[CH:2][c:3]1[cH:4][c:5]([O:6][C:7](=[O:8])[N:9]([CH3:10])[CH3:11])[cH:12][cH:13][c:14]1[CH:15]([OH:16])[CH2:18][CH2:19][O:20][Si:21]([c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)([c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1)[C:34]([CH3:35])([CH3:36])[CH3:37]>>[CH2:1]=[CH:2][c:3]1[cH:4][c:5]([O:... | BrC(Br)(Br)Br.C=Cc1cc(OC(=O)N(C)C)ccc1C(O)CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C | C=Cc1cc(OC(=O)N(C)C)ccc1C(O)(Br)CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C | null | null | ClCCl | Functional Group Interconversion | Bromination | 9f0ae5e83907ecc1fcfb1d88ad36f98595319ee8517fc263e77784e52e82e13b | f5672e6730ea422d01df5937ff46c934f5dfdf1d4fbf514db56d670518e21c21 | c1ccc(CCCO[SiH](c2ccccc2)c2ccccc2)cc1 | Br-C(-Br)(-Br)-[Br;H0;D1;+0:1].[C:2]-[C:3]-[CH;D3;+0:4](-[O;D1;H1:5])-[c:6](:[c:7]):[c:8]-[C:9]=[C;D1;H2:10]>>[Br;H0;D1;+0:1]-[C;H0;D4;+0:4](-[O;D1;H1:5])(-[C:3]-[C:2])-[c:6](:[c:7]):[c:8]-[C:9]=[C;D1;H2:10] | 78 | [{"value": 78.0, "product": "CN(C(OC1=CC(=C(C=C1)C(CCO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)(O)Br)C=C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.6, "product": "CN(C(OC1=CC(=C(C=C1)C(CCO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)(O)Br)C=C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | null | null | 1 | HOUR | To a solution of 4-[3-(t-butyl-diphenyl-silanyloxy)-1-hydroxy-propyl]-3-vinyl-phenyl dimethylcarbamate (3.00 g, 5.95 mmol) synthesized in step (f) of Example 192 and carbon tetrabromide (3.98 g, 12.0 mmol) in dichloromethane (20 ml) was added triphenyl phosphine (3.14 g, 12.0 mmol) at room temperature, and the resultin... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Secondary alcohol | Tertiary halide | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HBr | ClCCl | null | 1 | BrC(Br)(Br)Br.C=Cc1cc(OC(=O)N(C)C)ccc1C(O)CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C>ClCCl>C=Cc1cc(OC(=O)N(C)C)ccc1C(O)(Br)CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f25f9c42fcf341d0acb485d2c0b72893 | C=CCN.C=Cc1cc(OC(=O)N(C)C)ccc1C(O)(Br)CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C>>C=CCNC(O)(CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)c1ccc(OC(=O)N(C)C)cc1C=C | CN(C(OC1=CC(=C(C=C1)C(CCO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)(O)Br)C=C)=O)C.C(C=C)N>>CN(C(OC1=CC(=C(C=C1)C(CCO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)(O)NCC=C)C=C)=O)C | [CH2:1]=[CH:2][CH2:3][NH2:4].Br[C:5]([OH:6])([CH2:7][CH2:8][O:9][Si:10]([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[C:23]([CH3:24])([CH3:25])[CH3:26])[c:27]1[cH:28][cH:29][c:30]([O:31][C:32](=[O:33])[N:34]([CH3:35])[CH3:36])[cH:37][c:38]1[CH:39]=[CH2:40]>>[CH2:1]=[CH:2][CH2... | C=CCN.C=Cc1cc(OC(=O)N(C)C)ccc1C(O)(Br)CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C | C=CCNC(O)(CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)c1ccc(OC(=O)N(C)C)cc1C=C | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | 07af7d4c7984f572726ef942df12a89735b132164a86a1c8a3ba0c5326426194 | 1eca3e4a42a47a41a21e5d78efdcb9eebb24be6eecab751fa86ecd6c304b18a3 | c1ccc(CCCO[SiH](c2ccccc2)c2ccccc2)cc1 | Br-[C;H0;D4;+0:1](-[O;D1;H1:2])(-[C:3]-[C:4])-[c:5](:[c:6]):[c:7]-[C:8]=[C;D1;H2:9].[C;D1;H2:10]=[C:11]-[C:12]-[NH2;D1;+0:13]>>[C:4]-[C:3]-[C;H0;D4;+0:1](-[O;D1;H1:2])(-[NH;D2;+0:13]-[C:12]-[C:11]=[C;D1;H2:10])-[c:5](:[c:6]):[c:7]-[C:8]=[C;D1;H2:9] | 72 | [{"value": 72.0, "product": "CN(C(OC1=CC(=C(C=C1)C(CCO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)(O)NCC=C)C=C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.5, "product": "CN(C(OC1=CC(=C(C=C1)C(CCO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)(O)NCC=C)C=C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desir... | null | null | 8 | HOUR | To a solution of 4-[1-bromo-3-(t-butyl-diphenyl-silanyloxy)-1-hydroxy-propyl]-3-vinyl-phenyl dimethylcarbamate (2.62 g, 4.62 mmol) synthesized in step (g) of Example 192 in acetonitrile (20 ml) was added allylamine (1.87 ml, 25.0 mmol) at room temperature, and the resulting mixture was stirred at room temperature overn... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary alcohol.Primary amine | Tertiary alcohol.Secondary amine | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HBr | C(C)#N | null | 8 | C=CCN.C=Cc1cc(OC(=O)N(C)C)ccc1C(O)(Br)CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C>C(C)#N>C=CCNC(O)(CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)c1ccc(OC(=O)N(C)C)cc1C=C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-381171a6223d4c1aa1119c31b6d336b5 | C=CCN(C(=O)OC(C)(C)C)C(CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)c1ccc(OC(=O)N(C)C)cc1C=C>>CN(C)C(=O)Oc1ccc2c(c1)C=CCN(C(=O)OC(C)(C)C)C2CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C | C(C=C)N(C(OC(C)(C)C)=O)C(CCO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)C1=C(C=C(C=C1)OC(N(C)C)=O)C=C>>C(C)(C)(C)[Si](OCCC1N(CC=CC2=C1C=CC(=C2)OC(N(C)C)=O)C(=O)OC(C)(C)C)(C2=CC=CC=C2)C2=CC=CC=C2 | C=[CH:13][c:11]1[c:10]([CH:24]([N:16]([CH2:15][CH:14]=C)[C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH2:25][CH2:26][O:27][Si:28]([c:29]2[cH:30][cH:31][cH:32][cH:33][cH:34]2)([c:35]2[cH:36][cH:37][cH:38][cH:39][cH:40]2)[C:41]([CH3:42])([CH3:43])[CH3:44])[cH:9][cH:8][c:7]([O:6][C:4]([N:2]([CH3:1])[CH3:3])=[O... | C=CCN(C(=O)OC(C)(C)C)C(CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)c1ccc(OC(=O)N(C)C)cc1C=C | CN(C)C(=O)Oc1ccc2c(c1)C=CCN(C(=O)OC(C)(C)C)C2CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C | null | CC1=CC(=C(C(=C1)C)N2CCN([CH-]2)C3=C(C=C(C=C3C)C)C)C.C1CCC(CC1)[PH+](C2CCCCC2)C3CCCCC3.C1=CC=C(C=C1)C=[Ru](Cl)Cl | ClCCl | C-C Coupling | OtherReaction | 234a9f25d5c12ce6762f8b70a6ea1ebc56ad581f8e23f3c9a3e6209e4c8c40c9 | 7cc827c291e2a977a7a91dfb00752230897a77bed46038b3e1551b560ca4b6fc | C1=Cc2ccccc2C(CCO[SiH](c2ccccc2)c2ccccc2)NC1 | C=[CH;D2;+0:1]-[C:2]-[#7:3]-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C;D1;H3:10].C=[CH;D2;+0:11]-[c:12](:[c:13]):[c:14]>>[C;D1;H3:8]-[C:7](-[C;D1;H3:9])(-[C;D1;H3:10])-[#8:6]-[C:4](=[O;D1;H0:5])-[#7:3]-[C:2]-[CH;D2;+0:1]=[CH;D2;+0:11]-[c:12](:[c:13]):[c:14] | 96 | [{"value": 96.0, "product": "C(C)(C)(C)[Si](OCCC1N(CC=CC2=C1C=CC(=C2)OC(N(C)C)=O)C(=O)OC(C)(C)C)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.8, "product": "C(C)(C)(C)[Si](OCCC1N(CC=CC2=C1C=CC(=C2)OC(N(C)C)=O)C(=O)OC(C)(C)C)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERC... | 45 | CELSIUS | 3 | HOUR | To a solution of t-butyl allyl-[3-(t-butyl-diphenyl-silanyloxy)-1-(4-dimethylcarbamoyloxy-2-vinyl-phenyl)-propyl]-carbamate (360 mg, 0.56 mmol) synthesized in step (j) of Example 192 in dichloromethane (40 ml) was added tricyclohexylphosphine [1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene] [benzylidene] ... | 10.6084/m9.figshare.5104873.v1 | null | Allyl.Vinyl | null | null | C1=Cc2ccccc2C[NH]C1 | C1=Cc2ccccc2C[NH]C1.c1ccccc1.c1ccccc1 | Other | CC1=CC(=C(C(=C1)C)N2CCN([CH-]2)C3=C(C=C(C=C3C)C)C)C.C1CCC(CC1)[PH+](C2CCCCC2)C3CCCCC3.C1=CC=C(C=C1)C=[Ru](Cl)Cl.ClCCl | 45 | 3 | C=CCN(C(=O)OC(C)(C)C)C(CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)c1ccc(OC(=O)N(C)C)cc1C=C>CC1=CC(=C(C(=C1)C)N2CCN([CH-]2)C3=C(C=C(C=C3C)C)C)C.C1CCC(CC1)[PH+](C2CCCCC2)C3CCCCC3.C1=CC=C(C=C1)C=[Ru](Cl)Cl.ClCCl>CN(C)C(=O)Oc1ccc2c(c1)C=CCN(C(=O)OC(C)(C)C)C2CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a3532a4a42e944a4af8f8c4493acdd59 | CN(C)C(=O)Oc1ccc2c(c1)C=CCN(C(=O)OC(C)(C)C)C2CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C>>CN(C)C(=O)Oc1ccc2c(c1)C=CCN(C(=O)OC(C)(C)C)C2CCO | O.C(C)(C)(C)[Si](OCCC1N(CC=CC2=C1C=CC(=C2)OC(N(C)C)=O)C(=O)OC(C)(C)C)(C2=CC=CC=C2)C2=CC=CC=C2.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>CN(C(=O)OC1=CC2=C(C(N(CC=C2)C(=O)OC(C)(C)C)CCO)C=C1)C | CC(C)(C)[Si](c1ccccc1)(c1ccccc1)[O:27][CH2:26][CH2:25][CH:24]1[c:10]2[cH:9][cH:8][c:7]([O:6][C:4]([N:2]([CH3:1])[CH3:3])=[O:5])[cH:12][c:11]2[CH:13]=[CH:14][CH2:15][N:16]1[C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23]>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[O:6][c:7]1[cH:8][cH:9][c:10]2[c:11]([cH:12]1)[CH:13]=[CH:... | CN(C)C(=O)Oc1ccc2c(c1)C=CCN(C(=O)OC(C)(C)C)C2CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C | CN(C)C(=O)Oc1ccc2c(c1)C=CCN(C(=O)OC(C)(C)C)C2CCO | null | null | O1CCCC1 | Deprotection | Alcohol deprotection from silyl ethers | 5607047bc82bb27c5a65769b01ea0774767f4428c871f65da0b6352111d7a6e9 | 5c02ee98cb6b210a313993bea9e102110eb73637a50746f5457590f98613069b | C1=Cc2ccccc2CNC1 | C-C(-C)(-C)-[Si](-[O;H0;D2;+0:1]-[C:2]-[C:3])(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:3]-[C:2]-[OH;D1;+0:1] | 96 | [{"value": 96.0, "product": "CN(C(=O)OC1=CC2=C(C(N(CC=C2)C(=O)OC(C)(C)C)CCO)C=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.0, "product": "CN(C(=O)OC1=CC2=C(C(N(CC=C2)C(=O)OC(C)(C)C)CCO)C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of t-butyl 1-[2-(t-butyl-diphenyl-silanyloxy)-ethyl]-7-dimethylcarbamoyloxy-1,3-dihydro-benzo[c]azepine-2-carboxylate (1.82 g, 2.96 mmol) synthesized in step (k) of Example 192 in tetrahydrofuran (10 ml) was added 1M solution of tetrabutylammonium fluoride in tetrahydrofuran (6.0 ml, 6.0 mmol) at room tem... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | Primary alcohol | c1ccccc1.c1ccccc1 | null | C1=Cc2ccccc2C[NH]C1 | Other | O1CCCC1 | null | 1 | CN(C)C(=O)Oc1ccc2c(c1)C=CCN(C(=O)OC(C)(C)C)C2CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C>O1CCCC1>CN(C)C(=O)Oc1ccc2c(c1)C=CCN(C(=O)OC(C)(C)C)C2CCO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6cee12e455314b05a0df894b4946f502 | CN(C)C(=O)Oc1ccc2c(c1)C=CCN(C(=O)OC(C)(C)C)C2CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C>>CN(C)C(=O)Oc1ccc2c(c1)CCCN(C(=O)OC(C)(C)C)C2CCO | C(C)(C)(C)[Si](OCCC1N(CC=CC2=C1C=CC(=C2)OC(N(C)C)=O)C(=O)OC(C)(C)C)(C2=CC=CC=C2)C2=CC=CC=C2>>CN(C(=O)OC1=CC2=C(C(N(CCC2)C(=O)OC(C)(C)C)CCO)C=C1)C | CC(C)(C)[Si](c1ccccc1)(c1ccccc1)[O:27][CH2:26][CH2:25][CH:24]1[c:10]2[cH:9][cH:8][c:7]([O:6][C:4]([N:2]([CH3:1])[CH3:3])=[O:5])[cH:12][c:11]2[CH:13]=[CH:14][CH2:15][N:16]1[C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23]>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[O:6][c:7]1[cH:8][cH:9][c:10]2[c:11]([cH:12]1)[CH2:13][CH2... | CN(C)C(=O)Oc1ccc2c(c1)C=CCN(C(=O)OC(C)(C)C)C2CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C | CN(C)C(=O)Oc1ccc2c(c1)CCCN(C(=O)OC(C)(C)C)C2CCO | null | [C].[Pd] | CO | Deprotection | OtherReaction | c2fff42fb9a693441092f85389941ed8df04d25c6eaadf1cc5d271208c6c87e1 | 5c02ee98cb6b210a313993bea9e102110eb73637a50746f5457590f98613069b | c1ccc2c(c1)CCCNC2 | C-C(-C)(-C)-[Si](-[O;H0;D2;+0:1]-[C:2]-[C:3]-[C:4]1-[c:5]:[c:6](:[c:7])-[CH;D2;+0:8]=[CH;D2;+0:9]-[C:10]-[#7:11]-1-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15](-[C;D1;H3:16])(-[C;D1;H3:17])-[C;D1;H3:18])(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C;D1;H3:16]-[C:15](-[C;D1;H3:17])(-[C;D1;H3:18])-[#8:14]-[C:12](=[O;D1;H0:13])-[#7:11]1-[C... | 91 | [{"value": 91.0, "product": "CN(C(=O)OC1=CC2=C(C(N(CCC2)C(=O)OC(C)(C)C)CCO)C=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.8, "product": "CN(C(=O)OC1=CC2=C(C(N(CCC2)C(=O)OC(C)(C)C)CCO)C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of t-butyl 7-dimethylcarbamoyloxy-1-(2-hydroxyethyl)-1,3-dihydro-benzo[c]azepine-2-carboxylate (207 mg, 0.550 mmol) synthesized in step (k) of Example 192 in methanol (10 ml) was added 10% palladium carbon (27 mg), and the resulting mixture was stirred for 1 hour at room temperature. After stirring, the r... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | Primary alcohol | c1ccccc1.c1ccccc1.C1=Cc2ccccc2C[NH]C1 | c1ccc2c(c1)CCC[NH]C2 | c1ccc2c(c1)CCC[NH]C2 | Other | [C].[Pd].CO | null | 1 | CN(C)C(=O)Oc1ccc2c(c1)C=CCN(C(=O)OC(C)(C)C)C2CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C>[C].[Pd].CO>CN(C)C(=O)Oc1ccc2c(c1)CCCN(C(=O)OC(C)(C)C)C2CCO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-063195aff09549ee8e0feaf07aaf6768 | ClCc1ccccc1.O=Cc1ccc(O)cc1O>>O=Cc1ccc(OCc2ccccc2)cc1O | OC1=C(C=O)C=CC(=C1)O.C(O)([O-])=O.[Na+].[I-].[K+].C(C1=CC=CC=C1)Cl.Cl>>C(C1=CC=CC=C1)OC1=CC(=C(C=O)C=C1)O | Cl[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[cH:15][c:16]1[OH:17]>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15][c:16]1[OH:17] | ClCc1ccccc1.O=Cc1ccc(O)cc1O | O=Cc1ccc(OCc2ccccc2)cc1O | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(COc2ccccc2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4] | 56 | [{"value": 56.0, "product": "C(C1=CC=CC=C1)OC1=CC(=C(C=O)C=C1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.6, "product": "C(C1=CC=CC=C1)OC1=CC(=C(C=O)C=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2,4-dihydroxybenzaldehyde (50.0 g, 362 mmol) in acetonitrile (350 ml) were added sodium hydrogen carbonate (34.6 g, 412 mmol), potassium iodide (6.0 g, 36 mmol), and benzyl chloride (54.0 ml, 470 mmol), and the resulting mixture was refluxed for 24 hours under a nitrogen atmosphere. At the end of the r... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HCl | C(C)#N | null | null | ClCc1ccccc1.O=Cc1ccc(O)cc1O>C(C)#N>O=Cc1ccc(OCc2ccccc2)cc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-32bd1f0623724d6ab1dae36704536ed9 | COCCl.O=Cc1ccc(OCc2ccccc2)cc1O>>COCOc1cc(OCc2ccccc2)ccc1C=O | O.C(C1=CC=CC=C1)OC1=CC(=C(C=O)C=C1)O.C(C)(C)N(CC)C(C)C.COCCl>>C(C1=CC=CC=C1)OC1=CC(=C(C=O)C=C1)OCOC | Cl[CH2:3][O:2][CH3:1].[OH:4][c:5]1[cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][cH:17][c:18]1[CH:19]=[O:20]>>[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][cH:17][c:18]1[CH:19]=[O:20] | COCCl.O=Cc1ccc(OCc2ccccc2)cc1O | COCOc1cc(OCc2ccccc2)ccc1C=O | null | null | ClCCl | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 6e90ffbf0683e1a3ee55c5e3ea453aefc5ddd369c0150ed0150f9546d7e47f4f | efd670663709b79afcad1306da9f69b33a0147cfa3639ca4c0b54b35ef4b1852 | c1ccc(COc2ccccc2)cc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C;D1;H3:3].[O;D1;H0:4]=[C:5]-[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[C;D1;H3:3]-[#8:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:8]-[c:7](:[c:9]):[c:6]-[C:5]=[O;D1;H0:4] | 79 | [{"value": 79.0, "product": "C(C1=CC=CC=C1)OC1=CC(=C(C=O)C=C1)OCOC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.7, "product": "C(C1=CC=CC=C1)OC1=CC(=C(C=O)C=C1)OCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 4-benzyloxy-2-hydoxy-benzaldehyde (44.9 g, 197 mmol) synthesized in step (a) of Example 197 in dichloromethane (200 ml) were added diisopropylethylamine (52.0 ml, 300 mmol) and methoxymethyl chloride (20.5 ml, 270 mmol) at 0° C. with stirring, and the resulting mixture was stirred overnight at room tem... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Aromatic alcohol | Ether.Ether | null | null | c1ccccc1.c1ccccc1 | HCl | ClCCl | null | null | COCCl.O=Cc1ccc(OCc2ccccc2)cc1O>ClCCl>COCOc1cc(OCc2ccccc2)ccc1C=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4b39048c071d493d9559d5ce734b6843 | CCOC(=O)CP(=O)(OCC)OCC.COCOc1cc(OCc2ccccc2)ccc1C=O>>CCOC(=O)C=Cc1ccc(OCc2ccccc2)cc1OCOC | [H-].[Na+].C(C1=CC=CC=C1)OC1=CC(=C(C=O)C=C1)OCOC.O.C(C)OP(=O)(OCC)CC(=O)OCC>>C(C1=CC=CC=C1)OC1=CC(=C(C=C1)C=CC(=O)OCC)OCOC | CCOP(=O)(OCC)[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].O=[CH:7][c:8]1[cH:9][cH:10][c:11]([O:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[cH:20][c:21]1[O:22][CH2:23][O:24][CH3:25]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[CH:7][c:8]1[cH:9][cH:10][c:11]([O:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[c... | CCOC(=O)CP(=O)(OCC)OCC.COCOc1cc(OCc2ccccc2)ccc1C=O | CCOC(=O)C=Cc1ccc(OCc2ccccc2)cc1OCOC | null | null | O1CCCC1 | C-C Coupling | Wittig with Phosphonium | a86984aeb4a9963534e0b081b0ecca18455fda1775f36ce168d1ca4cf966df3e | 203dd34a20dceaf1737adbf20e01b43c2424e4e4b1722d942d1a796d895396e6 | c1ccc(COc2ccccc2)cc1 | C-C-O-P(=O)(-O-C-C)-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].O=[CH;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH;D2;+0:1]=[CH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 99.3 | [{"value": 99.0, "product": "C(C1=CC=CC=C1)OC1=CC(=C(C=C1)C=CC(=O)OCC)OCOC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.3, "product": "C(C1=CC=CC=C1)OC1=CC(=C(C=C1)C=CC(=O)OCC)OCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 55% sodium hydride dispersion in mineral oil (1.57 g, 36.0 mmol) in tetrahydrofuran (100 ml) was added ethyl diethylphosphonoacetate (7.17 g, 32.0 mmol) at 0° C. with stirring, and the resulting mixture was stirred for 30 minutes at 0° C. under a nitrogen atmosphere. Subsequently, a solution of 4-ben... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Ester | null | null | c1ccccc1.c1ccccc1 | HO- | O1CCCC1 | null | null | CCOC(=O)CP(=O)(OCC)OCC.COCOc1cc(OCc2ccccc2)ccc1C=O>O1CCCC1>CCOC(=O)C=Cc1ccc(OCc2ccccc2)cc1OCOC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6ab9d34cdbdb4a8fa75fc75df7f3247b | O=C(O)[C@@H]1C[C@@H](O)CN1.O=C=Nc1ccc(Cl)cc1>>O=C(O)[C@@H]1C[C@@H](O)CN1C(=O)Nc1ccc(Cl)cc1 | N1[C@H](C(=O)O)C[C@@H](O)C1.ClC1=CC=C(C=C1)N=C=O>>ClC1=CC=C(C=C1)NC(=O)N1[C@@H](C[C@H](C1)O)C(=O)O | [O:1]=[C:2]([OH:3])[C@@H:4]1[CH2:5][C@@H:6]([OH:7])[CH2:8][NH:9]1.[C:10](=[O:11])=[N:12][c:13]1[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]1>>[O:1]=[C:2]([OH:3])[C@@H:4]1[CH2:5][C@@H:6]([OH:7])[CH2:8][N:9]1[C:10](=[O:11])[NH:12][c:13]1[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]1 | O=C(O)[C@@H]1C[C@@H](O)CN1.O=C=Nc1ccc(Cl)cc1 | O=C(O)[C@@H]1C[C@@H](O)CN1C(=O)Nc1ccc(Cl)cc1 | null | null | [OH-].[Na+] | Acylation | Urea synthesis via isocyanate and secondary amine | 5098f6f2ef609d064ce90facf55c5845961063a83fbc6102544db855904309ec | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | O=C(Nc1ccccc1)N1CCCC1 | [O;D1;H0:1]=[C;H0;D2;+0:2]=[N;H0;D2;+0:3]-[c:4](:[c:5]):[c:6].[O;D1;H0:7]=[C:8](-[O;D1;H1:9])-[C:10]1-[C:11]-[C:12]-[C:13]-[NH;D2;+0:14]-1>>[O;D1;H0:1]=[C;H0;D3;+0:2](-[NH;D2;+0:3]-[c:4](:[c:5]):[c:6])-[N;H0;D3;+0:14]1-[C:13]-[C:12]-[C:11]-[C:10]-1-[C:8](=[O;D1;H0:7])-[O;D1;H1:9] | 90.7 | [{"value": 90.7, "product": "ClC1=CC=C(C=C1)NC(=O)N1[C@@H](C[C@H](C1)O)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -1 | CELSIUS | 1 | HOUR | 9.4 g (71.685 mmol) of L-hydroxyproline are dissolved in 71.68 ml of NaOH solution (c=1 mol/l) at from −2 to 0° C., a solution of 11.008 g (71.685 mmol) of 4-chlorophenyl isocyanate in 70 ml of IBMK is subsequently added, and the mixture is stirred at −1° C. for 1 hour. Conventional work-up gives 18.52 g of (2S,4R)-1-(... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1 | null | [OH-].[Na+] | -1 | 1 | O=C(O)[C@@H]1C[C@@H](O)CN1.O=C=Nc1ccc(Cl)cc1>[OH-].[Na+]>O=C(O)[C@@H]1C[C@@H](O)CN1C(=O)Nc1ccc(Cl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6dc50daf450343998cdcb2844ed06ef5 | CCCCCCCCCCCCCCCCCC(=O)CC(=O)OCC.N=C(N)NC(=N)Nc1ccccc1>>CCCCCCCCCCCCCCCCCc1cc(=O)[nH]c(NC(=N)Nc2ccccc2)n1 | C(C)OC(CC(CCCCCCCCCCCCCCCCC)=O)=O.C1(=CC=CC=C1)NC(=N)NC(=N)N>>C(CCCCCCCCCCCCCCCC)C=1N=C(NC(C1)=O)NC(=N)NC1=CC=CC=C1 | CCO[C:20]([CH2:19][C:18](=O)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:21].[NH2:22][C:23]([NH:24][C:25](=[NH:26])[NH:27][c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1)=[NH:34]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][... | CCCCCCCCCCCCCCCCCC(=O)CC(=O)OCC.N=C(N)NC(=N)Nc1ccccc1 | CCCCCCCCCCCCCCCCCc1cc(=O)[nH]c(NC(=N)Nc2ccccc2)n1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | e1086e09babe9a6eadacd25aedc6500fef83912c69ad4a008a7c15c97bbc10be | 65fdd7798538976255c7563b30d8ae7cc21639206d12c4373c064ac8a6ebaebc | N=C(Nc1ccccc1)Nc1nccc(=O)[nH]1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[C;H0;D3;+0:4](=O)-[C:5]-[C:6].[N;D1;H1:7]=[C:8]-[#7:9]-[C;H0;D3;+0:10](-[NH2;D1;+0:11])=[NH;D1;+0:12]>>[C:6]-[C:5]-[c;H0;D3;+0:4]1:[cH;D2;+0:3]:[c;H0;D3;+0:1](=[O;D1;H0:2]):[nH;D2;+0:11]:[c;H0;D3;+0:10](-[#7:9]-[C:8]=[N;D1;H1:7]):[n;H0;D2;+0:12]:1 | 58 | [{"value": 58.0, "product": "C(CCCCCCCCCCCCCCCC)C=1N=C(NC(C1)=O)NC(=N)NC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | In a 50 milliliter round-bottom flask, 3-oxoeicosanoic acid ethyl ester (2.25 grams, 6.60 mmol, prepared as described in Part B of this Example) was added at room temperature to a solution of 1-phenylbiguanide (1.17 grams, 6.60 mmol, prepared as described in Part D of this Example) in anhydrous ethanol (20 milliliters)... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary amine | null | null | c1ccncn1 | c1ccncn1.c1ccccc1 | HO- | C(C)O | null | 16 | CCCCCCCCCCCCCCCCCC(=O)CC(=O)OCC.N=C(N)NC(=N)Nc1ccccc1>C(C)O>CCCCCCCCCCCCCCCCCc1cc(=O)[nH]c(NC(=N)Nc2ccccc2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b67cd60a24074dd8b657e148f9a58d1d | CCCC(=O)CC(=O)OCC.N=C(N)NC(=N)Nc1ccccc1>>CCCc1cc(=O)[nH]c(NC(=N)Nc2ccccc2)n1 | C(C)OC(CC(CCC)=O)=O.C1(=CC=CC=C1)NC(=N)NC(=N)N>>O=C1C=C(N=C(N1)NC(=N)NC1=CC=CC=C1)CCC | CCO[C:6]([CH2:5][C:4](=O)[CH2:3][CH2:2][CH3:1])=[O:7].[NH2:8][C:9]([NH:10][C:11](=[NH:12])[NH:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)=[NH:20]>>[CH3:1][CH2:2][CH2:3][c:4]1[cH:5][c:6](=[O:7])[nH:8][c:9]([NH:10][C:11](=[NH:12])[NH:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[n:20]1 | CCCC(=O)CC(=O)OCC.N=C(N)NC(=N)Nc1ccccc1 | CCCc1cc(=O)[nH]c(NC(=N)Nc2ccccc2)n1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | e1086e09babe9a6eadacd25aedc6500fef83912c69ad4a008a7c15c97bbc10be | 65fdd7798538976255c7563b30d8ae7cc21639206d12c4373c064ac8a6ebaebc | N=C(Nc1ccccc1)Nc1nccc(=O)[nH]1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[C;H0;D3;+0:4](=O)-[C:5]-[C:6].[N;D1;H1:7]=[C:8]-[#7:9]-[C;H0;D3;+0:10](-[NH2;D1;+0:11])=[NH;D1;+0:12]>>[C:6]-[C:5]-[c;H0;D3;+0:4]1:[cH;D2;+0:3]:[c;H0;D3;+0:1](=[O;D1;H0:2]):[nH;D2;+0:11]:[c;H0;D3;+0:10](-[#7:9]-[C:8]=[N;D1;H1:7]):[n;H0;D2;+0:12]:1 | 72 | [{"value": 72.0, "product": "O=C1C=C(N=C(N1)NC(=N)NC1=CC=CC=C1)CCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.9, "product": "O=C1C=C(N=C(N1)NC(=N)NC1=CC=CC=C1)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | In a 50 milliliter round-bottom flask, 3-oxohexanoic acid ethyl ester (3.2 grams, 0.020 mol, obtained from Aldrich Chemical Co., Milwaukee, Wis.) was added at room temperature to a solution of 1-phenylbiguanide (3.5 grams, 0.020 mol, prepared as described in Part D of Example I) in anhydrous ethanol (15 milliliters). T... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary amine | null | null | c1ccncn1 | c1ccncn1.c1ccccc1 | HO- | C(C)O | null | 4 | CCCC(=O)CC(=O)OCC.N=C(N)NC(=N)Nc1ccccc1>C(C)O>CCCc1cc(=O)[nH]c(NC(=N)Nc2ccccc2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a7566352028a4f13b59e1667f01710b1 | CCOC(=O)CC(C)=O.Cc1ccccc1NC(=N)NC(=N)N>>Cc1cc(=O)[nH]c(NC(=N)Nc2ccccc2C)n1 | C(C)OC(CC(C)=O)=O.C1(=C(C=CC=C1)NC(=N)NC(=N)N)C>>CC=1N=C(NC(C1)=O)NC(=N)NC1=C(C=CC=C1)C | CCO[C:4]([CH2:3][C:2](=O)[CH3:1])=[O:5].[NH2:6][C:7]([NH:8][C:9](=[NH:10])[NH:11][c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[CH3:18])=[NH:19]>>[CH3:1][c:2]1[cH:3][c:4](=[O:5])[nH:6][c:7]([NH:8][C:9](=[NH:10])[NH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[CH3:18])[n:19]1 | CCOC(=O)CC(C)=O.Cc1ccccc1NC(=N)NC(=N)N | Cc1cc(=O)[nH]c(NC(=N)Nc2ccccc2C)n1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | e1086e09babe9a6eadacd25aedc6500fef83912c69ad4a008a7c15c97bbc10be | 65fdd7798538976255c7563b30d8ae7cc21639206d12c4373c064ac8a6ebaebc | N=C(Nc1ccccc1)Nc1nccc(=O)[nH]1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[C;H0;D3;+0:4](=O)-[C;D1;H3:5].[N;D1;H1:6]=[C:7]-[#7:8]-[C;H0;D3;+0:9](-[NH2;D1;+0:10])=[NH;D1;+0:11]>>[C;D1;H3:5]-[c;H0;D3;+0:4]1:[cH;D2;+0:3]:[c;H0;D3;+0:1](=[O;D1;H0:2]):[nH;D2;+0:10]:[c;H0;D3;+0:9](-[#7:8]-[C:7]=[N;D1;H1:6]):[n;H0;D2;+0:11]:1 | 68 | [{"value": 68.0, "product": "CC=1N=C(NC(C1)=O)NC(=N)NC1=C(C=CC=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.0, "product": "CC=1N=C(NC(C1)=O)NC(=N)NC1=C(C=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | In a 50 milliliter round-bottom flask, 3-oxobutyric acid ethyl ester (2.6 grams, 0.020 mol; obtained from Aldrich Chemical Co., Milwaukee, Wis.) was added at room temperature to a solution of 1-(o-tolyl)biguanide (3.8 grams, 0.020 mol; obtained from Aldrich Chemical Co.) in anhydrous ethanol (20 milliliters). The mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary amine | null | null | c1ccncn1 | c1ccncn1.c1ccccc1 | HO- | C(C)O | null | 4 | CCOC(=O)CC(C)=O.Cc1ccccc1NC(=N)NC(=N)N>C(C)O>Cc1cc(=O)[nH]c(NC(=N)Nc2ccccc2C)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8f6d1b8e87b54c30a12867320ad4f56d | CCOC(=O)CC(C)=O.N=C(N)NC(=N)Nc1ccccc1>>Cc1cc(=O)[nH]c(NC(=N)Nc2ccccc2)n1 | C(C)OC(CC(C)=O)=O.C1(=CC=CC=C1)NC(=N)NC(=N)N>>CC=1N=C(NC(C1)=O)NC(=N)NC1=CC=CC=C1 | CCO[C:4]([CH2:3][C:2](=O)[CH3:1])=[O:5].[NH2:6][C:7]([NH:8][C:9](=[NH:10])[NH:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)=[NH:18]>>[CH3:1][c:2]1[cH:3][c:4](=[O:5])[nH:6][c:7]([NH:8][C:9](=[NH:10])[NH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[n:18]1 | CCOC(=O)CC(C)=O.N=C(N)NC(=N)Nc1ccccc1 | Cc1cc(=O)[nH]c(NC(=N)Nc2ccccc2)n1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | e1086e09babe9a6eadacd25aedc6500fef83912c69ad4a008a7c15c97bbc10be | 65fdd7798538976255c7563b30d8ae7cc21639206d12c4373c064ac8a6ebaebc | N=C(Nc1ccccc1)Nc1nccc(=O)[nH]1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[C;H0;D3;+0:4](=O)-[C;D1;H3:5].[N;D1;H1:6]=[C:7]-[#7:8]-[C;H0;D3;+0:9](-[NH2;D1;+0:10])=[NH;D1;+0:11]>>[C;D1;H3:5]-[c;H0;D3;+0:4]1:[cH;D2;+0:3]:[c;H0;D3;+0:1](=[O;D1;H0:2]):[nH;D2;+0:10]:[c;H0;D3;+0:9](-[#7:8]-[C:7]=[N;D1;H1:6]):[n;H0;D2;+0:11]:1 | 74 | [{"value": 74.0, "product": "CC=1N=C(NC(C1)=O)NC(=N)NC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.0, "product": "CC=1N=C(NC(C1)=O)NC(=N)NC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | In a 50 milliliter round-bottom flask, 3-oxobutyric acid ethyl ester (2.6 grams, 0.020 mol; obtained from Aldrich Chemical Co., Milwaukee, Wis.) was added at room temperature to a solution of 1-phenylbiguanide (3.5 grams, 0.020 mol, prepared as described in Part D of Example I) in anhydrous ethanol (15 milliliters). Th... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary amine | null | null | c1ccncn1 | c1ccncn1.c1ccccc1 | HO- | C(C)O | null | 4 | CCOC(=O)CC(C)=O.N=C(N)NC(=N)Nc1ccccc1>C(C)O>Cc1cc(=O)[nH]c(NC(=N)Nc2ccccc2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-372f659a6cdc413fa9e9dd98cb986676 | COCc1ccccc1N>>COCc1ccccc1NN | [OH-].[Na+].N(=O)[O-].[Na+].COCC1=C(N)C=CC=C1>>COCC1=C(C=CC=C1)NN | [CH3:1][O:2][CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[NH2:10]>>[CH3:1][O:2][CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[NH:10][NH2:11] | COCc1ccccc1N | COCc1ccccc1NN | null | null | Cl.O | Miscellaneous | OtherReaction | c4079cd46dafde13b56adeac363106820ab4184dee8b1ca632594de2bba804bd | 5c8e4e590249a630a16b10bd7a77b27600fffbea367a0b585a920dd877e5471b | c1ccccc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]>>[N;D1;H2:5]-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 71 | [{"value": 71.0, "product": "COCC1=C(C=CC=C1)NN", "details": "PERCENTYIELD", "is_desired": false}] | -10 | CELSIUS | null | null | 6.86 g (50 m moles) of 2-methoxymethylaniline was dissolved in 50 ml of concentrated hydrochloric acid. The solution was cooled to −10° C. Thereto was dropwise added a solution of sodium nitrite (4.14 g, 60 m moles) dissolved in water (50 ml) while a temperature of −10° C. to 0° C. was being kept. Then, a solution of 4... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Hydrazine | null | null | c1ccccc1 | Other | Cl.O | -10 | null | COCc1ccccc1N>Cl.O>COCc1ccccc1NN |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d742d7a93779482eb57585ac353e1c56 | CC(C)=O.COc1cc(OC)nc(S(C)(=O)=O)n1>>COc1cc(OC)nc(CC(C)=O)n1 | CC(=O)C.[H-].[Na+].C1CCOC1.COC1=NC(=NC(=C1)OC)S(=O)(=O)C>>COC1=NC(=NC(=C1)OC)CC(C)=O | [CH3:10][C:11]([CH3:12])=[O:13].CS(=O)(=O)[c:9]1[n:8][c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[n:14]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[n:8][c:9]([CH2:10][C:11]([CH3:12])=[O:13])[n:14]1 | CC(C)=O.COc1cc(OC)nc(S(C)(=O)=O)n1 | COc1cc(OC)nc(CC(C)=O)n1 | null | null | O | C-C Coupling | OtherReaction | cb19a66d706bb959d7e5f15730f9b736c4d29916c0ab0003c0b4d3eef1a3e5a4 | e579149cef3e5a5fe1603dcc6e5770018d810af1f9af24a3b49a61f335f9d2dc | c1cncnc1 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C;D1;H3:6]-[C:7](-[CH3;D1;+0:8])=[O;D1;H0:9]>>[C;D1;H3:6]-[C:7](=[O;D1;H0:9])-[CH2;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | 22.4 | [{"value": 22.4, "product": "COC1=NC(=NC(=C1)OC)CC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 30 | CELSIUS | null | null | In a reactor were placed 16.0 g (0.4 moles) of 60% sodium hydride, 400 ml of THF and 43.6 g (0.2 moles) of 4,6-dimethoxy-2-methanesulfonylpyrimidine. The reactor contents were heated to 30° C. Thereto was dropwise added 39.4 g (0.68 moles) of acetone, followed by a reaction for 2 hours. After the completion of the reac... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Sulfone | Ketone | c1cncnc1 | c1cncnc1 | c1cncnc1 | HO- | O | 30 | null | CC(C)=O.COc1cc(OC)nc(S(C)(=O)=O)n1>O>COc1cc(OC)nc(CC(C)=O)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-401c4c5b9eb24e70afe9fcbdf091198d | CCc1ccccc1NN.COc1cc(OC)nc(CC(C)=O)n1>>CCc1cccc2c(-c3nc(OC)cc(OC)n3)c(C)[nH]c12 | COC1=NC(=NC(=C1)OC)CC(C)=O.Cl.C(C)C1=C(C=CC=C1)NN>>COC1=NC(=NC(=C1)OC)C1=C(NC2=C(C=CC=C12)CC)C | N[NH:21][c:22]1[c:3]([CH2:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]1.O=[C:19]([CH2:8][c:9]1[n:10][c:11]([O:12][CH3:13])[cH:14][c:15]([O:16][CH3:17])[n:18]1)[CH3:20]>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8](-[c:9]3[n:10][c:11]([O:12][CH3:13])[cH:14][c:15]([O:16][CH3:17])[n:18]3)[c:19]([CH3:20])[nH:21][c:22]12 | CCc1ccccc1NN.COc1cc(OC)nc(CC(C)=O)n1 | CCc1cccc2c(-c3nc(OC)cc(OC)n3)c(C)[nH]c12 | null | [Cl-].[Zn+2].[Cl-] | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | 100435ec2953aa65b16ed668d45eb4e5dc667892fed1592dbdc0dc96376e9936 | 1544c5676618f0f36e8bbf58b325093878e04c49fa9119d5ee93cb092dbc631d | c1cnc(-c2c[nH]c3ccccc23)nc1 | N-[NH;D2;+0:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6].O=[C;H0;D3;+0:7](-[C;D1;H3:8])-[CH2;D2;+0:9]-[c;H0;D3;+0:10](:[#7;a:11]:[c:12]):[#7;a:13]:[c:14]>>[C;D1;H3:8]-[c;H0;D3;+0:7]1:[nH;D2;+0:1]:[c:2](:[c:3]):[c;H0;D3;+0:4](:[c:5]:[c:6]):[c;H0;D3;+0:9]:1-[c;H0;D3;+0:10](:[#7;a:11]:[c:12]):[#7;a:13]:[c:14] | 81.3 | [{"value": 80.3, "product": "COC1=NC(=NC(=C1)OC)C1=C(NC2=C(C=CC=C12)CC)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.3, "product": "COC1=NC(=NC(=C1)OC)C1=C(NC2=C(C=CC=C12)CC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Into a reactor were fed 2.4 g (12.2 m moles) of 1-(4,6-dimethoxypyrimidine-2-yl)-2-propanone, 1.7 g (9.98 m moles) of 2-ethylphenylhydrazine hydrochloride, 1.4 g (10.2 m moles) of zinc chloride and 10 ml of toluene, followed by refluxing for 2 hours with heating. After the completion of the reaction, the reaction mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone | null | c1ccccc1 | c1ccc2[nH]ccc2c1 | c1cncnc1.c1ccc2[nH]ccc2c1 | HO- | [Cl-].[Zn+2].[Cl-].C1(=CC=CC=C1)C | null | null | CCc1ccccc1NN.COc1cc(OC)nc(CC(C)=O)n1>[Cl-].[Zn+2].[Cl-].C1(=CC=CC=C1)C>CCc1cccc2c(-c3nc(OC)cc(OC)n3)c(C)[nH]c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a3c8b03cb7b84446bcbdf136c3d61d34 | COCc1ccccc1NN.COc1cc(OC)nc(CC(C)=O)n1>>COCc1cccc2c(-c3nc(OC)cc(OC)n3)c(C)[nH]c12 | COC1=NC(=NC(=C1)OC)CC(C)=O.COCC1=C(C=CC=C1)NN.O.C1(=CC=CC=C1)C>>COC1=NC(=NC(=C1)OC)C1=C(NC2=C(C=CC=C12)COC)C | N[NH:22][c:23]1[c:4]([CH2:3][O:2][CH3:1])[cH:5][cH:6][cH:7][cH:8]1.O=[C:20]([CH2:9][c:10]1[n:11][c:12]([O:13][CH3:14])[cH:15][c:16]([O:17][CH3:18])[n:19]1)[CH3:21]>>[CH3:1][O:2][CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]2[c:9](-[c:10]3[n:11][c:12]([O:13][CH3:14])[cH:15][c:16]([O:17][CH3:18])[n:19]3)[c:20]([CH3:21])[nH:22][c:2... | COCc1ccccc1NN.COc1cc(OC)nc(CC(C)=O)n1 | COCc1cccc2c(-c3nc(OC)cc(OC)n3)c(C)[nH]c12 | null | [Cl-].[Zn+2].[Cl-] | C(C)(=O)OCC | Aromatic Heterocycle Formation | OtherReaction | 100435ec2953aa65b16ed668d45eb4e5dc667892fed1592dbdc0dc96376e9936 | 1544c5676618f0f36e8bbf58b325093878e04c49fa9119d5ee93cb092dbc631d | c1cnc(-c2c[nH]c3ccccc23)nc1 | N-[NH;D2;+0:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6].O=[C;H0;D3;+0:7](-[C;D1;H3:8])-[CH2;D2;+0:9]-[c;H0;D3;+0:10](:[#7;a:11]:[c:12]):[#7;a:13]:[c:14]>>[C;D1;H3:8]-[c;H0;D3;+0:7]1:[nH;D2;+0:1]:[c:2](:[c:3]):[c;H0;D3;+0:4](:[c:5]:[c:6]):[c;H0;D3;+0:9]:1-[c;H0;D3;+0:10](:[#7;a:11]:[c:12]):[#7;a:13]:[c:14] | 46.2 | [{"value": 46.0, "product": "COC1=NC(=NC(=C1)OC)C1=C(NC2=C(C=CC=C12)COC)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.2, "product": "COC1=NC(=NC(=C1)OC)C1=C(NC2=C(C=CC=C12)COC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Into a reactor were fed 6.2 g (31.6 m moles) of 1-(4,6-dimethoxypyrimidine-2-yl)-2-propanone, 4.8 g (31.5 m moles) of 2-methoxymethylphenylhydrazine, 4.76 g (34.9 m moles) of zinc chloride and 60 ml of toluene. Refluxing was made for 2 hours with heating. After the completion of the reaction, the reaction mixture was c... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone | null | c1ccccc1 | c1ccc2[nH]ccc2c1 | c1cncnc1.c1ccc2[nH]ccc2c1 | HO- | [Cl-].[Zn+2].[Cl-].C(C)(=O)OCC | null | 2 | COCc1ccccc1NN.COc1cc(OC)nc(CC(C)=O)n1>[Cl-].[Zn+2].[Cl-].C(C)(=O)OCC>COCc1cccc2c(-c3nc(OC)cc(OC)n3)c(C)[nH]c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-38b8c05896324093813bf0b9a1a53a4f | COc1cc(OC)nc(CC(C)=O)n1.NNc1ccccc1>>COc1cc(OC)nc(-c2c(C)[nH]c3ccccc23)n1 | COC1=NC(=NC(=C1)OC)CC(C)=O.C1(=CC=CC=C1)NN.C(C)(=O)OCC.O>>COC1=NC(=NC(=C1)OC)C1=C(NC2=CC=CC=C12)C | O=[C:11]([CH2:10][c:9]1[n:8][c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[n:20]1)[CH3:12].N[NH:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[n:8][c:9](-[c:10]2[c:11]([CH3:12])[nH:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]23)[n:20]1 | COc1cc(OC)nc(CC(C)=O)n1.NNc1ccccc1 | COc1cc(OC)nc(-c2c(C)[nH]c3ccccc23)n1 | null | [Cl-].[Zn+2].[Cl-] | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | 100435ec2953aa65b16ed668d45eb4e5dc667892fed1592dbdc0dc96376e9936 | 1544c5676618f0f36e8bbf58b325093878e04c49fa9119d5ee93cb092dbc631d | c1cnc(-c2c[nH]c3ccccc23)nc1 | N-[NH;D2;+0:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6].O=[C;H0;D3;+0:7](-[C;D1;H3:8])-[CH2;D2;+0:9]-[c;H0;D3;+0:10](:[#7;a:11]:[c:12]):[#7;a:13]:[c:14]>>[C;D1;H3:8]-[c;H0;D3;+0:7]1:[nH;D2;+0:1]:[c:2](:[c:3]):[c;H0;D3;+0:4](:[c:5]:[c:6]):[c;H0;D3;+0:9]:1-[c;H0;D3;+0:10](:[#7;a:11]:[c:12]):[#7;a:13]:[c:14] | 62 | [{"value": 62.0, "product": "COC1=NC(=NC(=C1)OC)C1=C(NC2=CC=CC=C12)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.0, "product": "COC1=NC(=NC(=C1)OC)C1=C(NC2=CC=CC=C12)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In 10 ml of toluene were dissolved 1.61 g (8.2 m moles) of 1-(4,6-dimethoxypyrimidine-2-yl)-2-propanone and 1.08 g (10 m moles) of phenylhydrazine. Thereto was added 1.36 g (10 m moles) of zinc chloride, followed by refluxing for 1 hour. The reaction mixture was allowed to cool, and ethyl acetate and water were added t... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone | null | c1ccccc1 | c1ccc2[nH]ccc2c1 | c1cncnc1.c1ccc2[nH]ccc2c1 | HO- | [Cl-].[Zn+2].[Cl-].C1(=CC=CC=C1)C | null | null | COc1cc(OC)nc(CC(C)=O)n1.NNc1ccccc1>[Cl-].[Zn+2].[Cl-].C1(=CC=CC=C1)C>COc1cc(OC)nc(-c2c(C)[nH]c3ccccc23)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1a9c4ecc38a444a3819090779b3e6868 | COc1cc(OC)nc(CC(C)=O)n1.Cc1ccccc1NN>>COc1cc(OC)nc(-c2c(C)[nH]c3c(C)cccc23)n1 | COC1=NC(=NC(=C1)OC)CC(C)=O.Cl.CC1=C(C=CC=C1)NN.C(C)(=O)OCC.O>>COC1=NC(=NC(=C1)OC)C1=C(NC2=C(C=CC=C12)C)C | O=[C:11]([CH2:10][c:9]1[n:8][c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[n:21]1)[CH3:12].N[NH:13][c:14]1[c:15]([CH3:16])[cH:17][cH:18][cH:19][cH:20]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[n:8][c:9](-[c:10]2[c:11]([CH3:12])[nH:13][c:14]3[c:15]([CH3:16])[cH:17][cH:18][cH:19][c:20]23)[n:21]1 | COc1cc(OC)nc(CC(C)=O)n1.Cc1ccccc1NN | COc1cc(OC)nc(-c2c(C)[nH]c3c(C)cccc23)n1 | null | [Cl-].[Zn+2].[Cl-] | C(C)(=O)OCC.CCCCCC.C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | 100435ec2953aa65b16ed668d45eb4e5dc667892fed1592dbdc0dc96376e9936 | 1544c5676618f0f36e8bbf58b325093878e04c49fa9119d5ee93cb092dbc631d | c1cnc(-c2c[nH]c3ccccc23)nc1 | N-[NH;D2;+0:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6].O=[C;H0;D3;+0:7](-[C;D1;H3:8])-[CH2;D2;+0:9]-[c;H0;D3;+0:10](:[#7;a:11]:[c:12]):[#7;a:13]:[c:14]>>[C;D1;H3:8]-[c;H0;D3;+0:7]1:[nH;D2;+0:1]:[c:2](:[c:3]):[c;H0;D3;+0:4](:[c:5]:[c:6]):[c;H0;D3;+0:9]:1-[c;H0;D3;+0:10](:[#7;a:11]:[c:12]):[#7;a:13]:[c:14] | 34.2 | [{"value": 34.0, "product": "COC1=NC(=NC(=C1)OC)C1=C(NC2=C(C=CC=C12)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 34.2, "product": "COC1=NC(=NC(=C1)OC)C1=C(NC2=C(C=CC=C12)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In 20 ml of toluene were dissolved 0.77 g (3.9 m moles) of 1-(4,6-dimethoxypyrimidine-2-yl)-2-propanone and 0.69 g (4.3 m moles) of 2-methylphenylhydrazine hydrochloride. Thereto was added 0.64 g (4.7 m moles) of zinc chloride, followed by refluxing for 2 hours. The reaction mixture was allowed to cool, and then ethyl ... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone | null | c1ccccc1 | c1ccc2[nH]ccc2c1 | c1cncnc1.c1ccc2[nH]ccc2c1 | HO- | [Cl-].[Zn+2].[Cl-].C(C)(=O)OCC.CCCCCC.C1(=CC=CC=C1)C | null | null | COc1cc(OC)nc(CC(C)=O)n1.Cc1ccccc1NN>[Cl-].[Zn+2].[Cl-].C(C)(=O)OCC.CCCCCC.C1(=CC=CC=C1)C>COc1cc(OC)nc(-c2c(C)[nH]c3c(C)cccc23)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4fdc6ef40e694658b59d4f1ba023267d | COc1cc(OC)nc(C(=O)CC(=O)Nc2ccccc2)n1>>COc1cc(OC)nc(C(=O)c2ccccc2N)n1 | COC1=NC(=NC(=C1)OC)C(=O)CC(=O)NC1=CC=CC=C1.Cl.[OH-].[Na+]>>COC1=NC(=NC(=C1)OC)C(=O)C1=C(N)C=CC=C1 | O=C(C[C:10]([c:9]1[n:8][c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[n:19]1)=[O:11])[NH:18][c:17]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[n:8][c:9]([C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[NH2:18])[n:19]1 | COc1cc(OC)nc(C(=O)CC(=O)Nc2ccccc2)n1 | COc1cc(OC)nc(C(=O)c2ccccc2N)n1 | null | null | CO | Functional Group Interconversion | OtherReaction | 23f7e35e2d856d68b88e5cbc135f7f8c4383aee611058ff9315205a580509534 | e633ca98aef6670ff2fb48de8c13eeeec91e37cd69a5b5492a6d1d045a74f271 | O=C(c1ccccc1)c1ncccn1 | O=C(-C-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[#7;a:4]:[c:5]):[#7;a:6]:[c:7])-[NH;D2;+0:8]-[c:9](:[c:10]):[cH;D2;+0:11]:[c:12]:[c:13]>>[NH2;D1;+0:8]-[c:9](:[c:10]):[c;H0;D3;+0:11](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[#7;a:4]:[c:5]):[#7;a:6]:[c:7]):[c:12]:[c:13] | null | [] | null | null | null | null | In a reactor were placed 0.57 g (1.9 m moles) of 2-(4,6-dimethoxypyrimidine-2-ylcarbonyl)acetanilide, 10 ml of methanol and 5 ml of 6 N hydrochloric acid, followed by refluxing for 1 hour with heating. After the completion of the reaction, the reaction mixture was made alkaline with sodium hydroxide, after which extrac... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amide | Ketone.Primary amine | c1ccccc1 | c1ccccc1 | c1cncnc1.c1ccccc1 | HO- | CO | null | null | COc1cc(OC)nc(C(=O)CC(=O)Nc2ccccc2)n1>CO>COc1cc(OC)nc(C(=O)c2ccccc2N)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e56f0fa679da49f997b3678573607a0e | COc1cc(OC)nc(-c2c(C)[nH]c3ccccc23)n1>>COc1cc(OC)nc(C(=O)c2ccccc2N)n1 | COC1=NC(=NC(=C1)OC)C1=C(NC2=CC=CC=C12)C.COC1=NC(=NC(=C1)OC)C1=C(NC2=CC=CC=C12)C.C(C)(=O)OCC.O=[O+][O-]>>COC1=NC(=NC(=C1)OC)C(=O)C1=C(N)C=CC=C1 | Cc1[c:10](-[c:9]2[n:8][c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[n:19]2)[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[nH:18]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[n:8][c:9]([C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[NH2:18])[n:19]1 | COc1cc(OC)nc(-c2c(C)[nH]c3ccccc23)n1 | COc1cc(OC)nc(C(=O)c2ccccc2N)n1 | null | null | O | Functional Group Interconversion | OtherReaction | 0d6596850467a81d710cadd8465fb5e063d0492af91f3d9eb2d3884bbc812c3a | 8ca0381f7ce1f1b377aa06c0e2d17e103e8360c43a71d76767a95464e88e866f | O=C(c1ccccc1)c1ncccn1 | C-c1:[nH;D2;+0:1]:[c:2](:[c:3]):[c:4](:[c:5]):[c;H0;D3;+0:6]:1-[c;H0;D3;+0:7](:[#7;a:8]:[c:9]):[#7;a:10]:[c:11]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4](-[C;H0;D3;+0:6](=[O;D1;H0:12])-[c;H0;D3;+0:7](:[#7;a:8]:[c:9]):[#7;a:10]:[c:11]):[c:5] | 46 | [{"value": 46.0, "product": "COC1=NC(=NC(=C1)OC)C(=O)C1=C(N)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | In a reactor were placed 0.60 g (22 m moles) of 3-(4,6-dimethoxypyrimidine-2-yl)-2-methylindole and 20 ml of ethyl acetate. Thereinto was blown ozone at 0° C. to 10° C. for 4 hours. Thin-layer chromatography was conducted to confirm the disappearance of 3-(4,6-dimethoxypyrimidine-2-yl)-2-methylindole and complete a rea... | 10.6084/m9.figshare.5104873.v1 | null | null | Ketone.Primary amine | c1ccc2[nH]ccc2c1 | c1ccccc1 | c1cncnc1.c1ccccc1 | Other | O | null | 1 | COc1cc(OC)nc(-c2c(C)[nH]c3ccccc23)n1>O>COc1cc(OC)nc(C(=O)c2ccccc2N)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ec94b331c19a429789e4a3c859c7e14c | COc1cc(OC)nc(CC(C)=O)n1.NNc1ccc(Cl)cc1>>COc1cc(OC)nc(-c2c(C)[nH]c3ccc(Cl)cc23)n1 | C1(=CC=CC=C1)C.COC1=NC(=NC(=C1)OC)CC(C)=O.Cl.ClC1=CC=C(C=C1)NN.C(C)(=O)OCC>>ClC=1C=C2C(=C(NC2=CC1)C)C1=NC(=CC(=N1)OC)OC | O=[C:11]([CH2:10][c:9]1[n:8][c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[n:21]1)[CH3:12].N[NH:13][c:14]1[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[n:8][c:9](-[c:10]2[c:11]([CH3:12])[nH:13][c:14]3[cH:15][cH:16][c:17]([Cl:18])[cH:19][c:20]23)[n:21]1 | COc1cc(OC)nc(CC(C)=O)n1.NNc1ccc(Cl)cc1 | COc1cc(OC)nc(-c2c(C)[nH]c3ccc(Cl)cc23)n1 | null | [Cl-].[Zn+2].[Cl-] | O | Aromatic Heterocycle Formation | OtherReaction | 100435ec2953aa65b16ed668d45eb4e5dc667892fed1592dbdc0dc96376e9936 | 1544c5676618f0f36e8bbf58b325093878e04c49fa9119d5ee93cb092dbc631d | c1cnc(-c2c[nH]c3ccccc23)nc1 | N-[NH;D2;+0:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6].O=[C;H0;D3;+0:7](-[C;D1;H3:8])-[CH2;D2;+0:9]-[c;H0;D3;+0:10](:[#7;a:11]:[c:12]):[#7;a:13]:[c:14]>>[C;D1;H3:8]-[c;H0;D3;+0:7]1:[nH;D2;+0:1]:[c:2](:[c:3]):[c;H0;D3;+0:4](:[c:5]:[c:6]):[c;H0;D3;+0:9]:1-[c;H0;D3;+0:10](:[#7;a:11]:[c:12]):[#7;a:13]:[c:14] | 84 | [{"value": 84.0, "product": "ClC=1C=C2C(=C(NC2=CC1)C)C1=NC(=CC(=N1)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.4, "product": "ClC=1C=C2C(=C(NC2=CC1)C)C1=NC(=CC(=N1)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To 80 ml of toluene were added 8.0 g (40 m moles) of 1-(4,6-dimethoxypyrimidine-2-yl)-2-propanone and 7.9 g (44 m moles) of 4-chlorophenylhydrazine hydrochloride. Thereto was added 6.54 g (48 m moles) of zinc chloride. Refluxing was made for 2 hours with heating. The reaction mixture was allowed to cool. Then, ethyl ac... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone | null | c1ccccc1 | c1ccc2[nH]ccc2c1 | c1cncnc1.c1ccc2[nH]ccc2c1 | HO- | [Cl-].[Zn+2].[Cl-].O | null | 2 | COc1cc(OC)nc(CC(C)=O)n1.NNc1ccc(Cl)cc1>[Cl-].[Zn+2].[Cl-].O>COc1cc(OC)nc(-c2c(C)[nH]c3ccc(Cl)cc23)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4835ac605a414fdbacc12aab68622979 | COC1=CC(Cl)(OC)NC(C(=O)CC(=O)Nc2ccccc2)=N1>>COC1=CC(Cl)(OC)NC(C(O)CC(=O)Nc2ccccc2)=N1 | ClC1(NC(=NC(=C1)OC)C(=O)CC(=O)NC1=CC=CC=C1)OC.[BH4-].[Na+].[Cl-].[NH4+]>>ClC1(NC(=NC(=C1)OC)C(CC(=O)NC1=CC=CC=C1)O)OC | [CH3:1][O:2][C:3]1=[CH:4][C:5]([Cl:6])([O:7][CH3:8])[NH:9][C:10]([C:11](=[O:12])[CH2:13][C:14](=[O:15])[NH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)=[N:23]1>>[CH3:1][O:2][C:3]1=[CH:4][C:5]([Cl:6])([O:7][CH3:8])[NH:9][C:10]([CH:11]([OH:12])[CH2:13][C:14](=[O:15])[NH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)=... | COC1=CC(Cl)(OC)NC(C(=O)CC(=O)Nc2ccccc2)=N1 | COC1=CC(Cl)(OC)NC(C(O)CC(=O)Nc2ccccc2)=N1 | null | null | C(C)O | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | O=C(CCC1=NC=CCN1)Nc1ccccc1 | [O;D1;H0:1]=[C:2](-[#7:3]-[c:4])-[C:5]-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[C:8]1=[#7:9]-[C:10]=[C:11]-[C:12]-[#7:13]-1>>[O;D1;H0:1]=[C:2](-[#7:3]-[c:4])-[C:5]-[CH;D3;+0:6](-[OH;D1;+0:7])-[C:8]1=[#7:9]-[C:10]=[C:11]-[C:12]-[#7:13]-1 | 68.6 | [{"value": 68.0, "product": "ClC1(NC(=NC(=C1)OC)C(CC(=O)NC1=CC=CC=C1)O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.6, "product": "ClC1(NC(=NC(=C1)OC)C(CC(=O)NC1=CC=CC=C1)O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | In a reactor were placed 1.00 g (3.0 m moles) of 4-chloro-2-(4,6-dimethoxypyrimidine-2-ylcarbonyl)acetanilide and 20 ml of ethanol. The reactor contents were cooled to 5° C. or less. Thereto was added 0.25 g (6.6 m moles) of sodium borohydride. The mixture was stirred at the same temperature for 1 hour. Then, the tempe... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | C1=CN=CNC1.c1ccccc1 | null | C(C)O | null | 1 | COC1=CC(Cl)(OC)NC(C(=O)CC(=O)Nc2ccccc2)=N1>C(C)O>COC1=CC(Cl)(OC)NC(C(O)CC(=O)Nc2ccccc2)=N1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e8396653ac5649f38ff675384758ab7f | COc1cc(OC)nc(CC(C)=O)n1.COc1ccc(NN)cc1>>COc1ccc2[nH]c(C)c(-c3nc(OC)cc(OC)n3)c2c1 | C1(=CC=CC=C1)C.COC1=NC(=NC(=C1)OC)CC(C)=O.Cl.COC1=CC=C(C=C1)NN.C(C)(=O)OCC>>COC1=NC(=NC(=C1)OC)C1=C(NC2=CC=C(C=C12)OC)C | O=[C:8]([CH3:9])[CH2:10][c:11]1[n:12][c:13]([O:14][CH3:15])[cH:16][c:17]([O:18][CH3:19])[n:20]1.N[NH:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:22][cH:21]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8]([CH3:9])[c:10](-[c:11]3[n:12][c:13]([O:14][CH3:15])[cH:16][c:17]([O:18][CH3:19])[n:20]3)[c:21]2[cH:22]1 | COc1cc(OC)nc(CC(C)=O)n1.COc1ccc(NN)cc1 | COc1ccc2[nH]c(C)c(-c3nc(OC)cc(OC)n3)c2c1 | null | [Cl-].[Zn+2].[Cl-] | O | Aromatic Heterocycle Formation | OtherReaction | 100435ec2953aa65b16ed668d45eb4e5dc667892fed1592dbdc0dc96376e9936 | 1544c5676618f0f36e8bbf58b325093878e04c49fa9119d5ee93cb092dbc631d | c1cnc(-c2c[nH]c3ccccc23)nc1 | N-[NH;D2;+0:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6].O=[C;H0;D3;+0:7](-[C;D1;H3:8])-[CH2;D2;+0:9]-[c;H0;D3;+0:10](:[#7;a:11]:[c:12]):[#7;a:13]:[c:14]>>[C;D1;H3:8]-[c;H0;D3;+0:7]1:[nH;D2;+0:1]:[c:2](:[c:3]):[c;H0;D3;+0:4](:[c:5]:[c:6]):[c;H0;D3;+0:9]:1-[c;H0;D3;+0:10](:[#7;a:11]:[c:12]):[#7;a:13]:[c:14] | 67 | [{"value": 67.0, "product": "COC1=NC(=NC(=C1)OC)C1=C(NC2=CC=C(C=C12)OC)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.5, "product": "COC1=NC(=NC(=C1)OC)C1=C(NC2=CC=C(C=C12)OC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To 80 ml of toluene were added 8.0 g (40 m moles) of 1-(4,6-dimethoxypyrimidine-2-yl)-2-propanone and 7.7 g (44 m moles) of 4-metoxyphenylhydrazine hydrochloride. Thereto was added 6.0 g (44 m moles) of zinc chloride. Refluxing was made for 2 hours with heating. The reaction mixture was allowed to cool. Thereto were ad... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone | null | c1ccccc1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1cncnc1 | HO- | [Cl-].[Zn+2].[Cl-].O | null | 2 | COc1cc(OC)nc(CC(C)=O)n1.COc1ccc(NN)cc1>[Cl-].[Zn+2].[Cl-].O>COc1ccc2[nH]c(C)c(-c3nc(OC)cc(OC)n3)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3efa0712dc2340ed91adc72ef5ec0cb8 | NCCCO.O.O=C1c2cccc(Cl)c2C(=O)c2cccc(Cl)c21>>O=C1c2cccc(NCCCO)c2C(=O)c2cccc(NCCCO)c21 | ClC1=CC=CC=2C(C3=C(C=CC=C3C(C12)=O)Cl)=O.NCCCO.O>>OCCCNC1=CC=CC=2C(C3=C(C=CC=C3C(C12)=O)NCCCO)=O | [NH2:8][CH2:9][CH2:10][CH2:11][OH:12].[OH2:25].Cl[c:7]1[cH:6][cH:5][cH:4][c:3]2[c:13]1[C:14](=[O:15])[c:16]1[cH:17][cH:18][cH:19][c:20](Cl)[c:26]1[C:2]2=[O:1]>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][c:7]([NH:8][CH2:9][CH2:10][CH2:11][OH:12])[c:13]2[C:14](=[O:15])[c:16]2[cH:17][cH:18][cH:19][c:20]([NH:21][CH2:22][CH2:23][... | NCCCO.O.O=C1c2cccc(Cl)c2C(=O)c2cccc(Cl)c21 | O=C1c2cccc(NCCCO)c2C(=O)c2cccc(NCCCO)c21 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 05ec3eecd5b7df847355b02ab91d17b3e17feb2ef9ab2cc1b2c86e9c17a738d0 | 71001d5587621f0ead4d5ce63004852d661b39664b02f5c0154590e6d86386f6 | O=C1c2ccccc2C(=O)c2ccccc21 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[C:6](=[O;D1;H0:7])-[c:8](:[c:9]-[C:10]-1=[O;D1;H0:11]):[c;H0;D3;+0:12](-Cl):[c:13]:[c:14].[C:15]-[C:16]-[NH2;D1;+0:17].[OH2;D0;+0:18]>>[C:15]-[C:16]-[NH;D2;+0:17]-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:8]1:[c:9]-[C:10](=[O;D1;H0:11])-[c:4](:[c:5]-[C:6]-1=[O;D1;H0:7]):[c;H0;D3;+... | null | [] | 130 | CELSIUS | null | null | 1,5-Dichloroanthraquinone (2.8 g; 10 mmol) is mixed with 3-amino-1-propanol (10 mL) in DMSO (50 mL) and heated to 130° C. for 4 hours. The mixture is cooled to ˜80° and added water (150 mL). When the mixture has reached RT the formed precipitate is isolated by filtration, washed with water (2×50 mL), boiled in toluene ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine | Primary alcohol.Secondary amine.Secondary amine | c1ccc2c(c1)Cc1ccccc1C2 | c1ccc2c(c1)Cc1ccccc1C2 | c1ccc2c(c1)Cc1ccccc1C2 | null | CS(=O)C | 130 | null | NCCCO.O.O=C1c2cccc(Cl)c2C(=O)c2cccc(Cl)c21>CS(=O)C>O=C1c2cccc(NCCCO)c2C(=O)c2cccc(NCCCO)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4c833a1722f14bb3875f575e13f03258 | O=C(O)c1ccc2c(c1)C(=O)c1c(O)ccc(O)c1C2=O>>O=C(O)c1ccc2c(c1)C(=O)C1=C(O)CCC(O)=C1C2=O | OC1=CC=C(C=2C(C3=CC(=CC=C3C(C12)=O)C(=O)O)=O)O>>OC=1CCC(=C2C(C3=CC(=CC=C3C(C12)=O)C(=O)O)=O)O | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[C:10](=[O:11])[c:12]1[c:13]([OH:14])[cH:15][cH:16][c:17]([OH:18])[c:19]1[C:20]2=[O:21]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[C:10](=[O:11])[C:12]1=[C:13]([OH:14])[CH2:15][CH2:16][C:17]([OH:18])=[C:19]1[C:20]2=[O:21] | O=C(O)c1ccc2c(c1)C(=O)c1c(O)ccc(O)c1C2=O | O=C(O)c1ccc2c(c1)C(=O)C1=C(O)CCC(O)=C1C2=O | null | [Zn] | C(C)(=O)O | Miscellaneous | OtherReaction | f199e0e1095ac78b0a5d1f0a95fcdf42f9f9512db1e1923f419e403c405cd04d | 9494a36d3f7cb35bc989c08aa1eb7c34d9c500b23979f96010df2c12329756db | O=C1C2=CCCC=C2C(=O)c2ccccc21 | [O;D1;H0:1]=[C:2]1-[c:3]:[c:4]-[C:5](=[O;D1;H0:6])-[c;H0;D3;+0:7]2:[c;H0;D3;+0:8]-1:[c;H0;D3;+0:9](-[O;D1;H1:10]):[cH;D2;+0:11]:[cH;D2;+0:12]:[c;H0;D3;+0:13]:2-[O;D1;H1:14]>>[O;D1;H0:1]=[C:2]1-[c:3]:[c:4]-[C:5](=[O;D1;H0:6])-[C;H0;D3;+0:7]2=[C;H0;D3;+0:13](-[O;D1;H1:14])-[CH2;D2;+0:12]-[CH2;D2;+0:11]-[C;H0;D3;+0:9](-[O... | null | [] | 100 | CELSIUS | 8 | HOUR | 1,4-Dihydroxy-anthraquinone-6-carboxylic acid (1.5 g) is mixed with Zn dust (3 g) in 300 mL glacial Acetic acid. The mixture is heated to 100° C. for 2 hours, filtered through Celite concentrated to half volume and added 250 mL water and placed at 5° C. overnight. The precipitate is collected by filtration. Yield: 1.1 ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Aromatic alcohol.Aromatic alcohol | Ketone.Ketone.Enol.Enol | c1ccc2c(c1)Cc1ccccc1C2 | C1=C2Cc3ccccc3CC2=CCC1 | C1=C2Cc3ccccc3CC2=CCC1 | null | [Zn].C(C)(=O)O | 100 | 8 | O=C(O)c1ccc2c(c1)C(=O)c1c(O)ccc(O)c1C2=O>[Zn].C(C)(=O)O>O=C(O)c1ccc2c(c1)C(=O)C1=C(O)CCC(O)=C1C2=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-713cfdb2f0bd488dbe98e499c9e656bb | Cc1ccc(N)cc1.O=C(O)c1ccc2c(c1)C(=O)C1=C(O)CCC(O)=C1C2=O>>Cc1ccc(Nc2ccc(Nc3ccc(C)cc3)c3c2C(=O)c2ccc(C(=O)O)cc2C3=O)cc1 | OC=1CCC(=C2C(C3=CC(=CC=C3C(C12)=O)C(=O)O)=O)O.NC1=CC=C(C=C1)C.O>>CC1=CC=C(C=C1)NC1=CC=C(C=2C(C3=CC(=CC=C3C(C12)=O)C(=O)O)=O)NC1=CC=C(C=C1)C | [CH3:1][c:2]1[cH:3][cH:4][c:5]([NH2:6])[cH:34][cH:35]1.O[C:7]1=[C:20]2[C:19](=[C:10](O)[CH2:9][CH2:8]1)[C:32](=[O:33])[c:31]1[c:23]([cH:24][cH:25][c:26]([C:27](=[O:28])[OH:29])[cH:30]1)[C:21]2=[O:22]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][c:7]2[cH:8][cH:9][c:10]([NH:11][c:12]3[cH:13][cH:14][c:15]([CH3:16])[cH:17][cH:18... | Cc1ccc(N)cc1.O=C(O)c1ccc2c(c1)C(=O)C1=C(O)CCC(O)=C1C2=O | Cc1ccc(Nc2ccc(Nc3ccc(C)cc3)c3c2C(=O)c2ccc(C(=O)O)cc2C3=O)cc1 | null | null | ClCCl.C1CCOC1.C(CCCC)O | Aromatic Heterocycle Formation | OtherReaction | c2cf30624fb310c10808db913a483df1d81f11991ae79c469209ebf4c880c476 | b54066a4670cbc38d840c3ab2bdee888f672614f7dc4f6d04fa81fe0e73112e5 | O=C1c2ccccc2C(=O)c2c(Nc3ccccc3)ccc(Nc3ccccc3)c21 | O-[C;H0;D3;+0:1]1=[C;H0;D3;+0:2]2-[C:3](=[O;D1;H0:4])-[c:5]:[c:6]-[C:7](=[O;D1;H0:8])-[C;H0;D3;+0:9]-2=[C;H0;D3;+0:10](-O)-[CH2;D2;+0:11]-[CH2;D2;+0:12]-1.[NH2;D1;+0:13]-[c:14](:[c:15]):[c:16]>>[O;D1;H0:8]=[C:7]1-[c:6]:[c:5]-[C:3](=[O;D1;H0:4])-[c;H0;D3;+0:2]2:[c;H0;D3;+0:1](-[#7:17]-[c:18]):[cH;D2;+0:12]:[cH;D2;+0:11]... | 72.2 | [{"value": 72.2, "product": "CC1=CC=C(C=C1)NC1=CC=C(C=2C(C3=CC(=CC=C3C(C12)=O)C(=O)O)=O)NC1=CC=C(C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | null | null | 1,4-Dihydroxy-2,3-dihydro-6-carboxy-anthraquinone (300 mg) Boric acid (300 mg) and p-Toluidine (1.8 g) is mixed in n-pentanol (5 mL) and heated to 110° C. for 4 hours, the mixture is co-evaporated with 2×50 ml of water. The residue is redissolved in dichloromethane/THF (1/1) 200 ml washed with water (3×100 mL) dried (N... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Enol.Enol.Primary amine | Ketone.Ketone.Secondary amine.Secondary amine | C1=C2Cc3ccccc3CC2=CCC1 | c1ccccc1.c1ccc2c(c1)Cc1ccccc1C2 | c1ccccc1.c1ccccc1.c1ccc2c(c1)Cc1ccccc1C2 | null | ClCCl.C1CCOC1.C(CCCC)O | 110 | null | Cc1ccc(N)cc1.O=C(O)c1ccc2c(c1)C(=O)C1=C(O)CCC(O)=C1C2=O>ClCCl.C1CCOC1.C(CCCC)O>Cc1ccc(Nc2ccc(Nc3ccc(C)cc3)c3c2C(=O)c2ccc(C(=O)O)cc2C3=O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5f48bf5a11d14a35a148d2be9dc00330 | Cl>>Cl | Cl.CN(CCCN=C=NCC)C.ON1N=NC2=C1C=CC=C2>>ON1N=NC2=C1C=CC=C2.Cl.CN(CCCN=C=NCC)C | [ClH:12]>>[ClH:12] | Cl | Cl | null | null | ClCCl | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | 5 | MINUTE | The acid (1.2 eq.), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.2 eq.) and 1-hydroxybenzotriazole (1.2 eq.) were dissolved in 20 volumes of dichloromethane and the solution stirred for 5 min at room temperature. A solution of the amine E (1 eq.) in 10 volumes dichloromethane was added to the mixture,... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | ClCCl | null | 0.083333 | Cl>ClCCl>Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-00fdc7451a7341299f677beb99af8ad6 | Cc1ccnc(S)n1>>CSc1nccc(C)n1 | Cl.SC1=NC=CC(=N1)C.C(C)(C)N(CC)C(C)C.COC(N(C)C)OC>>CC1=NC(=NC=C1)SC | [SH:2][c:3]1[n:4][cH:5][cH:6][c:7]([CH3:8])[n:9]1>>[CH3:1][S:2][c:3]1[n:4][cH:5][cH:6][c:7]([CH3:8])[n:9]1 | Cc1ccnc(S)n1 | CSc1nccc(C)n1 | null | null | C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | c0ae86859e4fe7d5090f82c7f1a16dde8df89659d0067c6301e7c852d1b2f7d9 | 576827748e0e5c16fea243bf3b7ba1f3406597e1bbf9247211b12bce17183ba5 | c1cncnc1 | [SH;D1;+0:1]-[c:2](:[#7;a:3]:[c:4]):[#7;a:5]:[c:6]>>[C;D1;H3:7]-[S;H0;D2;+0:1]-[c:2](:[#7;a:3]:[c:4]):[#7;a:5]:[c:6] | null | [] | null | null | null | null | A 22 L round bottom flask equipped with an air stirrer, heating mantle, thermometer, and reflux condenser was charged with toluene (12 L), 2-mercapto-4-methylpyrimidine hydrochloride (1) (900 g, 5.53 mol), diisopropylethylamine (1.07 kg, 8.30 mol), and N,N-dimethylformamide dimethyl acetal (1.61 kg, 12.7 mol). The reac... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic thiol | Monosulfide | null | null | c1cncnc1 | Other | C1(=CC=CC=C1)C | null | null | Cc1ccnc(S)n1>C1(=CC=CC=C1)C>CSc1nccc(C)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2045dab18e114bea8b0f18ec60021110 | CS(=O)(=O)c1nccc(-c2c(-c3ccc(F)cc3)nc3cc(CC#N)ccn23)n1>>CS(=O)(=O)c1nccc(-c2c(-c3ccc(F)cc3)nc3cc(CCN)ccn23)n1 | [H][H].C(C)O.FC1=CC=C(C=C1)C=1N=C2N(C=CC(=C2)CC#N)C1C1=NC(=NC=C1)S(=O)(=O)C.[H][H]>>FC1=CC=C(C=C1)C=1N=C2N(C=CC(=C2)CCN)C1C1=NC(=NC=C1)S(=O)(=O)C | [CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[n:6][cH:7][cH:8][c:9](-[c:10]2[c:11](-[c:12]3[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]3)[n:19][c:20]3[cH:21][c:22]([CH2:23][C:24]#[N:25])[cH:26][cH:27][n:28]23)[n:29]1>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[n:6][cH:7][cH:8][c:9](-[c:10]2[c:11](-[c:12]3[cH:13][cH:14][c:15]([F:16])[cH:17]... | CS(=O)(=O)c1nccc(-c2c(-c3ccc(F)cc3)nc3cc(CC#N)ccn23)n1 | CS(=O)(=O)c1nccc(-c2c(-c3ccc(F)cc3)nc3cc(CCN)ccn23)n1 | null | O=[Pt]=O.O=[Pt]=O | C(Cl)(Cl)Cl | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | c1ccc(-c2nc3ccccn3c2-c2ccncn2)cc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[C:3]-[c:4]>>[NH2;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[c:4] | null | [] | null | null | 12 | HOUR | A 300 mL pressure bottle containing nitrile 22 (980 mg, 2.41 mmol) was charged with ethanol (18 mL), chloroform (2 mL), and then PtO2 (200 mg, 0.881 mmol). The pressure bottle was then sealed, then charged with 50 psi hydrogen, and the reaction mixture was allowed to stir at room temperature for 12 hours, after which a... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1cncnc1.c1ccccc1.c1ccn2ccnc2c1 | null | O=[Pt]=O.O=[Pt]=O.C(Cl)(Cl)Cl | null | 12 | CS(=O)(=O)c1nccc(-c2c(-c3ccc(F)cc3)nc3cc(CC#N)ccn23)n1>O=[Pt]=O.O=[Pt]=O.C(Cl)(Cl)Cl>CS(=O)(=O)c1nccc(-c2c(-c3ccc(F)cc3)nc3cc(CCN)ccn23)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0e54cd889301404c9d9d917959710da3 | C=O.C=O.NCCc1ccn2c(-c3ccnc(N)n3)c(-c3ccc(F)cc3)nc2c1>>CN(C)CCc1ccn2c(-c3ccnc(N)n3)c(-c3ccc(F)cc3)nc2c1 | C=O.[BH3-]C#N.[Na+].NCCC1=CC=2N(C=C1)C(=C(N2)C2=CC=C(C=C2)F)C2=NC(=NC=C2)N.NCCC1=CC=2N(C=C1)C(=C(N2)C2=CC=C(C=C2)F)C2=NC(=NC=C2)N.C=O.[BH3-]C#N.[Na+]>>CN(CCC1=CC=2N(C=C1)C(=C(N2)C2=CC=C(C=C2)F)C2=NC(=NC=C2)N)C | O=[CH2:1].O=[CH2:3].[NH2:2][CH2:4][CH2:5][c:6]1[cH:7][cH:8][n:9]2[c:10](-[c:11]3[cH:12][cH:13][n:14][c:15]([NH2:16])[n:17]3)[c:18](-[c:19]3[cH:20][cH:21][c:22]([F:23])[cH:24][cH:25]3)[n:26][c:27]2[cH:28]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][c:6]1[cH:7][cH:8][n:9]2[c:10](-[c:11]3[cH:12][cH:13][n:14][c:15]([NH2:16])[n:1... | C=O.C=O.NCCc1ccn2c(-c3ccnc(N)n3)c(-c3ccc(F)cc3)nc2c1 | CN(C)CCc1ccn2c(-c3ccnc(N)n3)c(-c3ccc(F)cc3)nc2c1 | null | null | C(C)(=O)O.CO.C1CCOC1 | Heteroatom Alkylation and Arylation | Eschweiler-Clarke Primary Amine Methylation | 2089c0246e2f6d7fbf558363c9d5627bdf3f2974020c9cc0a6ebeeaee70ebc72 | 1137f8c4babb36e1409b79e98d0a5baa06f8e4a5b6a5f9ed168643657079f5a4 | c1ccc(-c2nc3ccccn3c2-c2ccncn2)cc1 | O=[CH2;D1;+0:1].O=[CH2;D1;+0:2].[C:3]-[C:4]-[NH2;D1;+0:5]>>[C:3]-[C:4]-[N;H0;D3;+0:5](-[CH3;D1;+0:1])-[CH3;D1;+0:2] | null | [] | null | null | null | null | A 28 mL Pyrex-Plus tube containing the product of Example 1, Step 9 (30 mg, 0.086 mmol) was charged with methanol (1.0 mL), then acetic acid (33 □L), then formaldehyde (28 mg of a 37% aqueous solution, 0.34 mmol), then NaBH3CN (431 □L of a 1.0M solution in THF, 0.431 mmol), and stirred at room temperature for 12 hours.... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Formaldehyde.Primary amine | Tertiary amine | null | null | c1cncnc1.c1ccccc1.c1ccn2ccnc2c1 | Other | C(C)(=O)O.CO.C1CCOC1 | null | null | C=O.C=O.NCCc1ccn2c(-c3ccnc(N)n3)c(-c3ccc(F)cc3)nc2c1>C(C)(=O)O.CO.C1CCOC1>CN(C)CCc1ccn2c(-c3ccnc(N)n3)c(-c3ccc(F)cc3)nc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9d2d6b95e52b4676820828501ae92e52 | CC(C)(C#N)c1ccn2c(-c3ccnc(N)n3)c(-c3ccc(F)cc3)nc2c1>>CC(C)(CN)c1ccn2c(-c3ccnc(N)n3)c(-c3ccc(F)cc3)nc2c1 | NC1=NC=CC(=N1)C1=C(N=C2N1C=CC(=C2)C(C#N)(C)C)C2=CC=C(C=C2)F.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>NCC(C)(C)C1=CC=2N(C=C1)C(=C(N2)C2=CC=C(C=C2)F)C2=NC(=NC=C2)N | [CH3:1][C:2]([CH3:3])([C:4]#[N:5])[c:6]1[cH:7][cH:8][n:9]2[c:10](-[c:11]3[cH:12][cH:13][n:14][c:15]([NH2:16])[n:17]3)[c:18](-[c:19]3[cH:20][cH:21][c:22]([F:23])[cH:24][cH:25]3)[n:26][c:27]2[cH:28]1>>[CH3:1][C:2]([CH3:3])([CH2:4][NH2:5])[c:6]1[cH:7][cH:8][n:9]2[c:10](-[c:11]3[cH:12][cH:13][n:14][c:15]([NH2:16])[n:17]3)[... | CC(C)(C#N)c1ccn2c(-c3ccnc(N)n3)c(-c3ccc(F)cc3)nc2c1 | CC(C)(CN)c1ccn2c(-c3ccnc(N)n3)c(-c3ccc(F)cc3)nc2c1 | null | null | C1CCOC1 | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | c1ccc(-c2nc3ccccn3c2-c2ccncn2)cc1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[c:4])-[C;H0;D2;+0:5]#[N;H0;D1;+0:6]>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[c:4])-[CH2;D2;+0:5]-[NH2;D1;+0:6] | null | [] | null | null | 45 | MINUTE | A 100 mL round bottom flask containing nitrile 27 (700 mg, 1.88 mmol) in THF (25 mL) was charged with lithium aluminum hydride (285 mg, 7.52 mmol). After stirring at room temperature for 45 minutes, the reaction mixture was poured into an 1.0 L Erlenmeyer flask and quenched with 200 mL ethyl acetate, 10 mL water, sodiu... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1cncnc1.c1ccccc1.c1ccn2ccnc2c1 | null | C1CCOC1 | null | 0.75 | CC(C)(C#N)c1ccn2c(-c3ccnc(N)n3)c(-c3ccc(F)cc3)nc2c1>C1CCOC1>CC(C)(CN)c1ccn2c(-c3ccnc(N)n3)c(-c3ccc(F)cc3)nc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f394c6fe0aa74eea8704dbc923d9f2c6 | C=O.CC(C)(CN)c1ccn2c(-c3ccnc(N)n3)c(-c3ccc(F)cc3)nc2c1.CO>>CN(C)CC(C)(C)c1ccn2c(-c3ccnc(N)n3)c(-c3ccc(F)cc3)nc2c1 | NCC(C)(C)C1=CC=2N(C=C1)C(=C(N2)C2=CC=C(C=C2)F)C2=NC(=NC=C2)N.[BH3-]C#N.[Na+].C=O.CO>>CN(CC(C)(C)C1=CC=2N(C=C1)C(=C(N2)C2=CC=C(C=C2)F)C2=NC(=NC=C2)N)C | O=[CH2:1].[NH2:2][CH2:4][C:5]([CH3:6])([CH3:7])[c:8]1[cH:9][cH:10][n:11]2[c:12](-[c:13]3[cH:14][cH:15][n:16][c:17]([NH2:18])[n:19]3)[c:20](-[c:21]3[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]3)[n:28][c:29]2[cH:30]1.O[CH3:3]>>[CH3:1][N:2]([CH3:3])[CH2:4][C:5]([CH3:6])([CH3:7])[c:8]1[cH:9][cH:10][n:11]2[c:12](-[c:13]3[cH:1... | C=O.CC(C)(CN)c1ccn2c(-c3ccnc(N)n3)c(-c3ccc(F)cc3)nc2c1.CO | CN(C)CC(C)(C)c1ccn2c(-c3ccnc(N)n3)c(-c3ccc(F)cc3)nc2c1 | null | null | C(C)(=O)O.C1CCOC1 | Heteroatom Alkylation and Arylation | Eschweiler-Clarke Primary Amine Methylation | d29df11c9c5ffd147cc1e60c079c2c51e4089a3e26b676bc79a2c949c420be78 | 67f5c6bf96e3775f98c4f864e32b898adbfa022155e63e5a2bc1c0626513b036 | c1ccc(-c2nc3ccccn3c2-c2ccncn2)cc1 | O-[CH3;D1;+0:1].O=[CH2;D1;+0:2].[C:3]-[C:4]-[NH2;D1;+0:5]>>[C:3]-[C:4]-[N;H0;D3;+0:5](-[CH3;D1;+0:2])-[CH3;D1;+0:1] | null | [] | null | null | 1 | HOUR | A 28 mL Pyrex-Plus tube containing amine 28 (Example 3, 170 mg, 0.452 mmol) was charged with methanol (2.0 mL), then acetic acid (170 □L), then formaldehyde (110 mg of a 37% aqueous solution, 1.35 mmol), then NaBH3CN (2.26 mL of a 1.0M solution in THF, 2.26 mmol). After stirring at room temperature for 1 hour, the reac... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Primary amine.Methanol | Tertiary amine | null | null | c1cncnc1.c1ccccc1.c1ccn2ccnc2c1 | HO- | C(C)(=O)O.C1CCOC1 | null | 1 | C=O.CC(C)(CN)c1ccn2c(-c3ccnc(N)n3)c(-c3ccc(F)cc3)nc2c1.CO>C(C)(=O)O.C1CCOC1>CN(C)CC(C)(C)c1ccn2c(-c3ccnc(N)n3)c(-c3ccc(F)cc3)nc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e52defd2a44444dfab7e49ae98a8d258 | CON.O=C(CBr)c1ccc(F)cc1>>CON=C(CBr)c1ccc(F)cc1 | FC1=CC=C(C(CBr)=O)C=C1.CO.Cl.CON.[Br-].[Li+]>>CON=C(CBr)C1=CC=C(C=C1)F | [CH3:1][O:2][NH2:3].O=[C:4]([CH2:5][Br:6])[c:7]1[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]1>>[CH3:1][O:2][N:3]=[C:4]([CH2:5][Br:6])[c:7]1[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]1 | CON.O=C(CBr)c1ccc(F)cc1 | CON=C(CBr)c1ccc(F)cc1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 3d7a74a3d1c5abb5292963d4a3067f1fb8a89aead752dc9bb1d63522c4c0bd5c | 6b0edeaa66853687109d0d530554f76edf36b01a8ec084e7ae9c709f0949a6b9 | c1ccccc1 | O=[C;H0;D3;+0:1](-[C:2]-[Br;D1;H0:3])-[c:4](:[c:5]):[c:6].[C;D1;H3:7]-[#8:8]-[NH2;D1;+0:9]>>[Br;D1;H0:3]-[C:2]-[C;H0;D3;+0:1](=[N;H0;D2;+0:9]-[#8:8]-[C;D1;H3:7])-[c:4](:[c:5]):[c:6] | null | [] | 60 | CELSIUS | null | null | A 2.0 L round bottom flask was charged with 4-fluorophenacyl bromide (97.6 g, 450 mmol), then methanol (750 mL), then O-methylhydroxylamine hydrochloride (75.1 g, 899 mol), and the mixture was heated to 65° C. for 2 hours. The reaction mixture was then concentrated under reduced pressure, charged with acetone (750 mL),... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | null | null | null | c1ccccc1 | HO- | CC(=O)C | 60 | null | CON.O=C(CBr)c1ccc(F)cc1>CC(=O)C>CON=C(CBr)c1ccc(F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-834fce27d77a4e8384f0597fd5038b28 | O=C(Cl)OCc1ccccc1.c1cc(C2CCNCC2)ccn1>>O=C(OCc1ccccc1)N1CCC(c2ccncc2)CC1 | C(=O)(O)[O-].[Na+].N1CCC(CC1)C1=CC=NC=C1.C(C)N(CC)CC.C(=O)(OCC1=CC=CC=C1)Cl>>N1=CC=C(C=C1)C1CCN(CC1)C(=O)OCC1=CC=CC=C1 | Cl[C:2](=[O:1])[O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1.[NH:11]1[CH2:12][CH2:13][CH:14]([c:15]2[cH:16][cH:17][n:18][cH:19][cH:20]2)[CH2:21][CH2:22]1>>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[N:11]1[CH2:12][CH2:13][CH:14]([c:15]2[cH:16][cH:17][n:18][cH:19][cH:20]2)[CH2:21][CH2:22]1 | O=C(Cl)OCc1ccccc1.c1cc(C2CCNCC2)ccn1 | O=C(OCc1ccccc1)N1CCC(c2ccncc2)CC1 | null | null | null | Protection | N-alkylation of secondary amines with alkyl halides | c6eb958652ca8104567d61601fc03a9cfee33fb7bb328952993831b03fec41c4 | d86dc1e6d0e089b3444b62ddfcf4c4822bdac4b60e628553036562518c29adcd | O=C(OCc1ccccc1)N1CCC(c2ccncc2)CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4])-[C:8]-[C:9] | null | [] | null | null | 12 | HOUR | A 10 mL round bottom flask was charged with piperidine 32 (500 mg, 3.08 mmol), and then triethylamine (314 mg, 3.10 mmol), and then CbzCl (529 mg, 3.10 mmol), and the reaction mixture was allowed to stir at room temperature for 12 hours. The reaction mixture was then poured into 50 mL of an aqueous solution saturated w... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Secondary amine | Carbamic ester | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccncc1 | HCl | null | null | 12 | O=C(Cl)OCc1ccccc1.c1cc(C2CCNCC2)ccn1>>O=C(OCc1ccccc1)N1CCC(c2ccncc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6ca4f6d6afc34f95b1150242e1d90c51 | CON=C(CBr)c1ccc(F)cc1.O=C(OCc1ccccc1)N1CCC(c2ccncc2)CC1>>O=C(OCc1ccccc1)N1CCC(c2ccn3cc(-c4ccc(F)cc4)nc3c2)CC1 | N1=CC=C(C=C1)C1CCN(CC1)C(=O)OCC1=CC=CC=C1.CON=C(CBr)C1=CC=C(C=C1)F.C(=O)(O)[O-].[Na+].CC(C)([O-])C.[K+]>>FC1=CC=C(C=C1)C=1N=C2N(C=CC(=C2)C2CCN(CC2)C(=O)OCC2=CC=CC=C2)C1 | CO[N:28]=[C:20]([CH2:19]Br)[c:21]1[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]1.[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[N:11]1[CH2:12][CH2:13][CH:14]([c:15]2[cH:16][cH:17][n:18][cH:29][cH:30]2)[CH2:31][CH2:32]1>>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[N:11]1[CH2:12][CH2:13]... | CON=C(CBr)c1ccc(F)cc1.O=C(OCc1ccccc1)N1CCC(c2ccncc2)CC1 | O=C(OCc1ccccc1)N1CCC(c2ccn3cc(-c4ccc(F)cc4)nc3c2)CC1 | null | null | CC(=O)C | Aromatic Heterocycle Formation | OtherReaction | 062b88bab18fc87005350b7d10a53ba2e17eb3797ee31fd4c6762f0185e460d9 | bba2945f18bbb88e48f2c5641704d2237fa5a07400e9b29e8d58901a4d971dcb | O=C(OCc1ccccc1)N1CCC(c2ccn3cc(-c4ccccc4)nc3c2)CC1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=[N;H0;D2;+0:3]-O-C)-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8].[c:9]1:[c:10]:[c:11]:[n;H0;D2;+0:12]:[cH;D2;+0:13]:[c:14]:1>>[c:6]:[c:5]:[c;H0;D3;+0:4](-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[n;H0;D3;+0:12]2:[c:11]:[c:10]:[c:9]:[c:14]:[c;H0;D3;+0:13]:2:[n;H0;D2;+0:3]:1):[c:7]:[c:8] | null | [] | null | null | 12 | HOUR | A 500 mL round bottom flask was charged with crude pyridine 33 (8.20 g, 27.7 mmol), acetone (300 mL), and O-methyloxime 30 (6.8 g, 27.7 mmol), and the reaction mixture was allowed to stir at room temperature for 12 hours, after which thin-layer chromatography testing suggested that pyridinyl salt formation was complete... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccncc1 | c1ccn2ccnc2c1 | c1ccccc1.C1CC[NH]CC1.c1ccn2ccnc2c1.c1ccccc1 | HBr | CC(=O)C | null | 12 | CON=C(CBr)c1ccc(F)cc1.O=C(OCc1ccccc1)N1CCC(c2ccncc2)CC1>CC(=O)C>O=C(OCc1ccccc1)N1CCC(c2ccn3cc(-c4ccc(F)cc4)nc3c2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d22e45b0d2c44cec96c70cd36581360c | CC(=O)OCc1c2ccccc2c(COC(C)=O)c2ccccc12.O=C(OCc1ccccc1)N1CCC(c2ccn3cc(-c4ccc(F)cc4)nc3c2)CC1>>CC(=O)c1c(-c2ccc(F)cc2)nc2cc(C3CCN(C(=O)OCc4ccccc4)CC3)ccn12 | FC1=CC=C(C=C1)C=1N=C2N(C=CC(=C2)C2CCN(CC2)C(=O)OCC2=CC=CC=C2)C1.CC(=O)OCC1=C2C=CC=CC2=C(C3=CC=CC=C31)COC(=O)C>>C(C)(=O)C1=C(N=C2N1C=CC(=C2)C2CCN(CC2)C(=O)OCC2=CC=CC=C2)C2=CC=C(C=C2)F | CC(=O)OCc1c2ccccc2c(CO[C:2]([CH3:1])=[O:3])c2ccccc12.[cH:4]1[c:5](-[c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[n:13][c:14]2[cH:15][c:16]([CH:17]3[CH2:18][CH2:19][N:20]([C:21](=[O:22])[O:23][CH2:24][c:25]4[cH:26][cH:27][cH:28][cH:29][cH:30]4)[CH2:31][CH2:32]3)[cH:33][cH:34][n:35]12>>[CH3:1][C:2](=[O:3])[c:4]1[c:5](-... | CC(=O)OCc1c2ccccc2c(COC(C)=O)c2ccccc12.O=C(OCc1ccccc1)N1CCC(c2ccn3cc(-c4ccc(F)cc4)nc3c2)CC1 | CC(=O)c1c(-c2ccc(F)cc2)nc2cc(C3CCN(C(=O)OCc4ccccc4)CC3)ccn12 | null | S(O)(O)(=O)=O | null | C-C Coupling | Friedel-Crafts acylation | 882c8fe1fe8226dd3c6cd527c5e3c7a9ef4a9c898a69a6019005ffc85bc84009 | 53456c3e87e97f512921684f59b54573df1eee9d8c313db55cd612727f50bb31 | O=C(OCc1ccccc1)N1CCC(c2ccn3cc(-c4ccccc4)nc3c2)CC1 | C-C(=O)-O-C-c1:c2:c:c:c:c:c:2:c(-C-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]):c2:c:c:c:c:c:1:2.[c:4]:[c:5]1:[#7;a:6]:[c:7](-[c:8]):[cH;D2;+0:9]:[#7;a:10]:1:[c:11]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[c;H0;D3;+0:9]1:[#7;a:10](:[c:11]):[c:5](:[c:4]):[#7;a:6]:[c:7]:1-[c:8] | null | [] | 140 | CELSIUS | null | null | Imidazopyridine 34 (290 mg, 0.675 mmol) was dissolved in acetic (50 mL) in a 250 mL round bottom flask. Three drops of sulfuric acid were then added, and the reaction was heated to 140° C. for 24 hours. The reaction was then concentrated under reduced pressure, then diluted with both ethyl acetate and saturated sodium ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Ketone | c1ccc2cc3ccccc3cc2c1.c1ccn2ccnc2c1 | c1ccn2ccnc2c1 | c1ccccc1.c1ccn2ccnc2c1.C1CC[NH]CC1.c1ccccc1 | HO- | S(O)(O)(=O)=O | 140 | null | CC(=O)OCc1c2ccccc2c(COC(C)=O)c2ccccc12.O=C(OCc1ccccc1)N1CCC(c2ccn3cc(-c4ccc(F)cc4)nc3c2)CC1>S(O)(O)(=O)=O>CC(=O)c1c(-c2ccc(F)cc2)nc2cc(C3CCN(C(=O)OCc4ccccc4)CC3)ccn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8d9e4fd23fab4936add64df3c80e7f2e | CC(=O)c1c(-c2ccc(F)cc2)nc2cc(C3CCN(C(=O)OCc4ccccc4)CC3)ccn12.N=C(N)N>>Nc1nccc(-c2c(-c3ccc(F)cc3)nc3cc(C4CCN(C(=O)OCc5ccccc5)CC4)ccn23)n1 | Cl.NC(=N)N.C[O-].[Na+].C(C)(=O)C1=C(N=C2N1C=CC(=C2)C2CCN(CC2)C(=O)OCC2=CC=CC=C2)C2=CC=C(C=C2)F.CN(C)C(OC)OC.CN(C)C(OC)OC>>NC1=NC=CC(=N1)C1=C(N=C2N1C=CC(=C2)C2CCN(CC2)C(=O)OCC2=CC=CC=C2)C2=CC=C(C=C2)F | O=[C:6]([CH3:5])[c:7]1[c:8](-[c:9]2[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]2)[n:16][c:17]2[cH:18][c:19]([CH:20]3[CH2:21][CH2:22][N:23]([C:24](=[O:25])[O:26][CH2:27][c:28]4[cH:29][cH:30][cH:31][cH:32][cH:33]4)[CH2:34][CH2:35]3)[cH:36][cH:37][n:38]12.[NH2:1][C:2](=[NH:3])[NH2:39]>>[NH2:1][c:2]1[n:3][cH:4][cH:5][c:6](-[... | CC(=O)c1c(-c2ccc(F)cc2)nc2cc(C3CCN(C(=O)OCc4ccccc4)CC3)ccn12.N=C(N)N | Nc1nccc(-c2c(-c3ccc(F)cc3)nc3cc(C4CCN(C(=O)OCc5ccccc5)CC4)ccn23)n1 | null | null | C1(=CC=CC=C1)C.CO | Aromatic Heterocycle Formation | OtherReaction | 033592cf85bde1eecf5df9a935388df53853b5e27177177b6d392deee27485d9 | 8182c33d66a1c51620dac2e3d5b839c3fec60d5b5668262efc6be8b10c115a58 | O=C(OCc1ccccc1)N1CCC(c2ccn3c(-c4ccncn4)c(-c4ccccc4)nc3c2)CC1 | O=[C;H0;D3;+0:1](-[CH3;D1;+0:2])-[c;H0;D3;+0:3]1:[#7;a:4](:[c:5]):[c:6](:[c:7]):[#7;a:8]:[c:9]:1-[c:10].[N;D1;H2:11]-[C;H0;D3;+0:12](-[NH2;D1;+0:13])=[NH;D1;+0:14]>>[N;D1;H2:11]-[c;H0;D3;+0:12]1:[n;H0;D2;+0:13]:[c;H0;D3;+0:1](-[c;H0;D3;+0:3]2:[#7;a:4](:[c:5]):[c:6](:[c:7]):[#7;a:8]:[c:9]:2-[c:10]):[cH;D2;+0:2]:[c:15]:[... | null | [] | 100 | CELSIUS | null | null | A 28 mL Pyrex Plus tube was charged with ketone 35 (420 mg, 0.89 mmol), DMFDMA (530 mg, 4.45 mmol) and toluene (10 mL). The reaction was heated to 100° C. for 7 hours, after which more DMFDMA (530 mg, 4.45 mmol) was added, and the reaction was allowed to heat at 100° C. for 12 more hours. The reaction was then concentr... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | null | null | c1cncnc1 | c1cncnc1.c1ccccc1.c1ccn2ccnc2c1.C1CC[NH]CC1.c1ccccc1 | null | C1(=CC=CC=C1)C.CO | 100 | null | CC(=O)c1c(-c2ccc(F)cc2)nc2cc(C3CCN(C(=O)OCc4ccccc4)CC3)ccn12.N=C(N)N>C1(=CC=CC=C1)C.CO>Nc1nccc(-c2c(-c3ccc(F)cc3)nc3cc(C4CCN(C(=O)OCc5ccccc5)CC4)ccn23)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3aced184e76142c7b010866d410568c4 | Nc1nccc(-c2c(-c3ccc(F)cc3)nc3cc(C4CCN(C(=O)OCc5ccccc5)CC4)ccn23)n1>>Nc1nccc(-c2c(-c3ccc(F)cc3)nc3cc(C4CCNCC4)ccn23)n1 | NC1=NC=CC(=N1)C1=C(N=C2N1C=CC(=C2)C2CCN(CC2)C(=O)OCC2=CC=CC=C2)C2=CC=C(C=C2)F.[Si](C)(C)(C)I>>FC1=CC=C(C=C1)C=1N=C2N(C=CC(=C2)C2CCNCC2)C1C1=NC(=NC=C1)N | O=C(OCc1ccccc1)[N:23]1[CH2:22][CH2:21][CH:20]([c:19]2[cH:18][c:17]3[n:16][c:8](-[c:9]4[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]4)[c:7](-[c:6]4[cH:5][cH:4][n:3][c:2]([NH2:1])[n:29]4)[n:28]3[cH:27][cH:26]2)[CH2:25][CH2:24]1>>[NH2:1][c:2]1[n:3][cH:4][cH:5][c:6](-[c:7]2[c:8](-[c:9]3[cH:10][cH:11][c:12]([F:13])[cH:14][cH:1... | Nc1nccc(-c2c(-c3ccc(F)cc3)nc3cc(C4CCN(C(=O)OCc5ccccc5)CC4)ccn23)n1 | Nc1nccc(-c2c(-c3ccc(F)cc3)nc3cc(C4CCNCC4)ccn23)n1 | null | null | CC#N | Reduction | Hydrogenolysis of tertiary amines | ce0208fabe82d1244d7db7b6f7627b1b39a8cf3492e02720426849e93718e81c | 20c36f41eeb07c3ba4437b51ba72e8ff3c22d0b27e7197b0e9af3127f331149f | c1ccc(-c2nc3cc(C4CCNCC4)ccn3c2-c2ccncn2)cc1 | O=C(-O-C-c1:c:c:c:c:c:1)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | null | [] | null | null | 2 | HOUR | Benzyl carbonate 37 (190 mg, 0.36 mmol) was slurried in CH3CN (5 mL) in a 28 mL Pyrex Plus tube. TMSI (720 mg, 3.6 mmol) was then added, and the reaction was allowed to stir at room temperature for 2 hours. The reaction was then concentrated under reduced pressure. The crude product was then dissolved in 10 mL CH2Cl2, ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Secondary amine | c1ccccc1.C1CC[NH]CC1 | C1CCNCC1 | c1cncnc1.c1ccccc1.c1ccn2ccnc2c1.C1CCNCC1 | HO- | CC#N | null | 2 | Nc1nccc(-c2c(-c3ccc(F)cc3)nc3cc(C4CCN(C(=O)OCc5ccccc5)CC4)ccn23)n1>CC#N>Nc1nccc(-c2c(-c3ccc(F)cc3)nc3cc(C4CCNCC4)ccn23)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-efcc27b145fc4b6dbfe3817357eba0c9 | C=O.CNCC(=O)O.CSc1nccc(-c2c(-c3ccc(F)cc3)nc3cc(C=O)ccn23)n1>>CSc1nccc(-c2c(-c3ccc(F)cc3)nc3cc(C4CN(C)CO4)ccn23)n1 | FC1=CC=C(C=C1)C=1N=C2N(C=CC(=C2)C=O)C1C1=NC(=NC=C1)SC.N(C)CC(=O)O.C=O>>FC1=CC=C(C=C1)C=1N=C2N(C=CC(=C2)C2CN(CO2)C)C1C1=NC(=NC=C1)SC | O=[CH2:22].O=C(O)[CH2:25][NH:23][CH3:24].[CH3:1][S:2][c:3]1[n:4][cH:5][cH:6][c:7](-[c:8]2[c:9](-[c:10]3[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]3)[n:17][c:18]3[cH:19][c:20]([CH:21]=[O:26])[cH:27][cH:28][n:29]23)[n:30]1>>[CH3:1][S:2][c:3]1[n:4][cH:5][cH:6][c:7](-[c:8]2[c:9](-[c:10]3[cH:11][cH:12][c:13]([F:14])[cH:15][c... | C=O.CNCC(=O)O.CSc1nccc(-c2c(-c3ccc(F)cc3)nc3cc(C=O)ccn23)n1 | CSc1nccc(-c2c(-c3ccc(F)cc3)nc3cc(C4CN(C)CO4)ccn23)n1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 7f7cbfa9a185fd583016cf0f17d937d619fcd56a64b89863dc4a2dfbb7b15285 | 3ec86f7094fbdf34185ff9b9e9c85d24640471054d91effa718f24c58aa7ef95 | c1ccc(-c2nc3cc(C4CNCO4)ccn3c2-c2ccncn2)cc1 | O-C(=O)-[CH2;D2;+0:1]-[NH;D2;+0:2]-[C;D1;H3:3].O=[CH2;D1;+0:4].[#7;a:5]:[c:6]1:[#7;a:7]:[c:8]:[c:9]:[c:10](-[CH;D2;+0:11]=[O;H0;D1;+0:12]):[c:13]:1>>[#7;a:5]:[c:6]1:[#7;a:7]:[c:8]:[c:9]:[c:10](-[CH;D3;+0:11]2-[CH2;D2;+0:4]-[N;H0;D3;+0:2](-[C;D1;H3:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:12]-2):[c:13]:1 | null | [] | null | null | null | null | A 250 mL round bottom flask equipped with a Dean Stark trap was charged with aldehyde 40 (1.44 g, 3.95 mmol), toluene (120 mL), sarcosine (710 mg, 7.97 mmol), and paraformaldehyde (600 mg, 20.0 mmol), and the reaction was heated under reflux for 12 hours, then concentrated under reduced pressure, dissolved in a minimum... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Formaldehyde.Carboxylic acid.Secondary amine | Ether.Tertiary amine | null | C1COC[NH]1 | c1cncnc1.c1ccccc1.c1ccn2ccnc2c1.C1COC[NH]1 | HO- | C1(=CC=CC=C1)C | null | null | C=O.CNCC(=O)O.CSc1nccc(-c2c(-c3ccc(F)cc3)nc3cc(C=O)ccn23)n1>C1(=CC=CC=C1)C>CSc1nccc(-c2c(-c3ccc(F)cc3)nc3cc(C4CN(C)CO4)ccn23)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a94a29055fb04529b500a0bdbee6977b | CSc1nccc(-c2c(-c3ccc(F)cc3)nc3cc(C4CN(C)CO4)ccn23)n1>>CSc1nccc(-c2c(-c3ccc(F)cc3)nc3cc(C(O)CN(C)C)ccn23)n1 | FC1=CC=C(C=C1)C=1N=C2N(C=CC(=C2)C2CN(CO2)C)C1C1=NC(=NC=C1)SC.[BH4-].[Na+]>>FC1=CC=C(C=C1)C=1N=C2N(C=CC(=C2)C(CN(C)C)O)C1C1=NC(=NC=C1)SC | [CH3:1][S:2][c:3]1[n:4][cH:5][cH:6][c:7](-[c:8]2[c:9](-[c:10]3[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]3)[n:17][c:18]3[cH:19][c:20]([CH:21]4[O:22][CH2:26][N:24]([CH3:25])[CH2:23]4)[cH:27][cH:28][n:29]23)[n:30]1>>[CH3:1][S:2][c:3]1[n:4][cH:5][cH:6][c:7](-[c:8]2[c:9](-[c:10]3[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]3)[... | CSc1nccc(-c2c(-c3ccc(F)cc3)nc3cc(C4CN(C)CO4)ccn23)n1 | CSc1nccc(-c2c(-c3ccc(F)cc3)nc3cc(C(O)CN(C)C)ccn23)n1 | null | null | C(C)O | Reduction | OtherReaction | 4cfddb114f56f37340a594a080229eadec6ec6d7905fdefe83d09df04f9d7864 | 7198fae1b68de0a7b3cad42fd2e176cc1d426019158d5ea9d2333b476668381b | c1ccc(-c2nc3ccccn3c2-c2ccncn2)cc1 | [C;D1;H3:1]-[#7:2]1-[C:3]-[C:4](-[c:5])-[O;H0;D2;+0:6]-[CH2;D2;+0:7]-1>>[C;D1;H3:1]-[#7:2](-[CH3;D1;+0:7])-[C:3]-[C:4](-[OH;D1;+0:6])-[c:5] | 78 | [{"value": 78.0, "product": "FC1=CC=C(C=C1)C=1N=C2N(C=CC(=C2)C(CN(C)C)O)C1C1=NC(=NC=C1)SC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A 100 mL round bottom flask was charged with oxazolidine 41 (1.65 g, 3.91 mmol), ethanol (50 mL), and sodium borohydride (450 mg, 11.9 mmol), and stirred at room temperature for 3 hours. The reaction was then quenched with 16 mL of a 20% NH4Cl aqueous solution and concentrated under reduced pressure, then diluted with ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Secondary alcohol | C1COC[NH]1 | null | c1cncnc1.c1ccccc1.c1ccn2ccnc2c1 | null | C(C)O | null | 3 | CSc1nccc(-c2c(-c3ccc(F)cc3)nc3cc(C4CN(C)CO4)ccn23)n1>C(C)O>CSc1nccc(-c2c(-c3ccc(F)cc3)nc3cc(C(O)CN(C)C)ccn23)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fcab5d554e6f420f8f6d1c0ac68e61c5 | CSc1nccc(-c2c(-c3ccc(F)cc3)nc3cc(C(O)CN(C)C)ccn23)n1>>CN(C)CC(O)c1ccn2c(-c3ccnc(S(C)(=O)=O)n3)c(-c3ccc(F)cc3)nc2c1 | CC(=O)C.FC1=CC=C(C=C1)C=1N=C2N(C=CC(=C2)C(CN(C)C)O)C1C1=NC(=NC=C1)SC.CO.OOS(=O)[O-].[K+]>>FC1=CC=C(C=C1)C=1N=C2N(C=CC(=C2)C(CN(C)C)O)C1C1=NC(=NC=C1)S(=O)(=O)C | [CH3:1][N:2]([CH3:3])[CH2:4][CH:5]([OH:6])[c:7]1[cH:8][cH:9][n:10]2[c:11](-[c:12]3[cH:13][cH:14][n:15][c:16]([S:17][CH3:18])[n:21]3)[c:22](-[c:23]3[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]3)[n:30][c:31]2[cH:32]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]([OH:6])[c:7]1[cH:8][cH:9][n:10]2[c:11](-[c:12]3[cH:13][cH:14][n:15][c:1... | CSc1nccc(-c2c(-c3ccc(F)cc3)nc3cc(C(O)CN(C)C)ccn23)n1 | CN(C)CC(O)c1ccn2c(-c3ccnc(S(C)(=O)=O)n3)c(-c3ccc(F)cc3)nc2c1 | null | null | O | Oxidation | OtherReaction | 20dd6d48007b4fe7cd760226f21413eb5e71e6468db112596c2e7ea4858c8ac1 | 5cedc1bf0f43f21d78a249521ecfcec19fc5ac4895c41eed0e84f0c2618149fa | c1ccc(-c2nc3ccccn3c2-c2ccncn2)cc1 | [C;D1;H3:1]-[S;H0;D2;+0:2]-[c:3](:[#7;a:4]:[c:5]):[#7;a:6]:[c:7]>>[C;D1;H3:1]-[S;H0;D4;+0:2](=[O;D1;H0:8])(=[O;D1;H0:9])-[c:3](:[#7;a:4]:[c:5]):[#7;a:6]:[c:7] | null | [] | null | null | 12 | HOUR | A 100 mL round bottom flask containing sulfide 42 (720 mg, 1.70 mmol) was charged with methanol (20 mL), then a solution of Oxone (3.14 g, 5.10 mmol) in water (20 mL), then acetone (20 mL). After stirring at room temperature for 12 hours, the reaction was cooled to below −20° C. in a dry ice/isopropanol bath, then SO2 ... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfone | null | null | c1cncnc1.c1ccccc1.c1ccn2ccnc2c1 | null | O | null | 12 | CSc1nccc(-c2c(-c3ccc(F)cc3)nc3cc(C(O)CN(C)C)ccn23)n1>O>CN(C)CC(O)c1ccn2c(-c3ccnc(S(C)(=O)=O)n3)c(-c3ccc(F)cc3)nc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1375763e9574418eb3c62ab805798e6d | CN(C)CC(O)c1ccn2c(-c3ccnc(S(C)(=O)=O)n3)c(-c3ccc(F)cc3)nc2c1.N>>CN(C)CC(O)c1ccn2c(-c3ccnc(N)n3)c(-c3ccc(F)cc3)nc2c1 | FC1=CC=C(C=C1)C=1N=C2N(C=CC(=C2)C(CN(C)C)O)C1C1=NC(=NC=C1)S(=O)(=O)C.N>>NC1=NC=CC(=N1)C1=C(N=C2N1C=CC(=C2)C(CN(C)C)O)C2=CC=C(C=C2)F | CS(=O)(=O)[c:16]1[n:15][cH:14][cH:13][c:12](-[c:11]2[n:10]3[cH:9][cH:8][c:7]([CH:5]([CH2:4][N:2]([CH3:1])[CH3:3])[OH:6])[cH:29][c:28]3[n:27][c:19]2-[c:20]2[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]2)[n:18]1.[NH3:17]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]([OH:6])[c:7]1[cH:8][cH:9][n:10]2[c:11](-[c:12]3[cH:13][cH:14][n:15][... | CN(C)CC(O)c1ccn2c(-c3ccnc(S(C)(=O)=O)n3)c(-c3ccc(F)cc3)nc2c1.N | CN(C)CC(O)c1ccn2c(-c3ccnc(N)n3)c(-c3ccc(F)cc3)nc2c1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 0df63c04fd55be98ca39182d8f4f4d16d72aabb6056c0f6f9e96aa52dbd78c65 | 1cb6e4ccd7feedf162eba914f190eaabd9f811c1cb52ba3c70e53d81b5441966 | c1ccc(-c2nc3ccccn3c2-c2ccncn2)cc1 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH3;D0;+0:6]>>[NH2;D1;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | 12 | HOUR | A pressure bottle containing sulfone 43 (320 mg, 0.703 mmol) was charged with tetrahydrofuran (40 mL), then chilled to <−40° C. in a dry ice/isopropanol bath. Ammonia gas (5.3 g, 0.31 mol) was then bubbled into the reaction. The pressure bottle was then sealed, and the reaction was allowed to warm to room temperature w... | 10.6084/m9.figshare.5104873.v1 | null | Sulfone | Primary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1.c1ccn2ccnc2c1 | HO- | O1CCCC1 | null | 12 | CN(C)CC(O)c1ccn2c(-c3ccnc(S(C)(=O)=O)n3)c(-c3ccc(F)cc3)nc2c1.N>O1CCCC1>CN(C)CC(O)c1ccn2c(-c3ccnc(N)n3)c(-c3ccc(F)cc3)nc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f81d1b41f4f045dfae2e4397dfb54c83 | CCOC(=O)Cc1nc2ccccc2nc1C(=O)O.O=P(Cl)(Cl)Cl>>O=C(O)c1nc2ccccc2nc1Cl | CN(C)C=O.C(C)OC(CC1=NC2=CC=CC=C2N=C1C(=O)O)=O.C(C)OC(CC1=NC2=CC=CC=C2N=C1C(=O)O)=O.O=P(Cl)(Cl)Cl>>ClC=1C(=NC2=CC=CC=C2N1)C(=O)O | CCOC(=O)C[c:13]1[c:4]([C:2](=[O:1])[OH:3])[n:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[n:12]1.O=P(Cl)(Cl)[Cl:14]>>[O:1]=[C:2]([OH:3])[c:4]1[n:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[n:12][c:13]1[Cl:14] | CCOC(=O)Cc1nc2ccccc2nc1C(=O)O.O=P(Cl)(Cl)Cl | O=C(O)c1nc2ccccc2nc1Cl | null | null | ClCCl | Functional Group Interconversion | OtherReaction | 2532f22ac4ba1935d10ec0d8973bc5d8ec1e417240370f6ad67fd193d9aa8b90 | b932ebc2b0b5ddc4902a67cc2f57e15f6a3097b596efce6b41903884d34fcdf3 | c1ccc2nccnc2c1 | C-C-O-C(=O)-C-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[C:7](=[O;D1;H0:8])-[O;D1;H1:9].Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:10]>>[Cl;H0;D1;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[C:7](=[O;D1;H0:8])-[O;D1;H1:9] | null | [] | 75 | CELSIUS | 1 | HOUR | From crude 16d, with a changed ratio of 1 g 16d: 0.8 mL POCl3: 1.6 mL DMF. The reaction mixture was heated, with moisture exclusion, at 75° C. for 16 h, then cooled, diluted with cold dichloromethane, and kept at −18° C. for 1 h. The brick red solid was filtered and washed exhaustively, with thorough stirring, with col... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Aromatic halide | c1ccc2nccnc2c1 | c1ccc2nccnc2c1 | c1ccc2nccnc2c1 | HCl | ClCCl | 75 | 1 | CCOC(=O)Cc1nc2ccccc2nc1C(=O)O.O=P(Cl)(Cl)Cl>ClCCl>O=C(O)c1nc2ccccc2nc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5607a5ae052246579c0ccc31910e8da9 | CN.CN(C)C=C1C(=O)OC(=O)c2cc3cccnc3nc21>>Cn1cc(C(=O)O)c2nc3ncccc3cc2c1=O | CN(C)C=C1C(OC(C=2C1=NC=1N=CC=CC1C2)=O)=O.CN>>CN1C(C=2C=C3C(=NC2C(=C1)C(=O)O)N=CC=C3)=O | [CH3:1][NH2:2].CN(C)[CH:3]=[C:4]1[C:5](=[O:6])[O:7][C:18](=[O:19])[c:17]2[c:8]1[n:9][c:10]1[n:11][cH:12][cH:13][cH:14][c:15]1[cH:16]2>>[CH3:1][n:2]1[cH:3][c:4]([C:5](=[O:6])[OH:7])[c:8]2[n:9][c:10]3[n:11][cH:12][cH:13][cH:14][c:15]3[cH:16][c:17]2[c:18]1=[O:19] | CN.CN(C)C=C1C(=O)OC(=O)c2cc3cccnc3nc21 | Cn1cc(C(=O)O)c2nc3ncccc3cc2c1=O | null | null | null | Miscellaneous | OtherReaction | e24e3fabf23ea370ba12abef3a11ccf1d7f1e3540b9031a7bc9620c21b2d3360 | 65cd6a35c5b072a8fab6ba6647692237b7343907b15b8d5326ebeac4c8a69aaa | O=c1[nH]ccc2nc3ncccc3cc12 | C-N(-C)-[CH;D2;+0:1]=[C;H0;D3;+0:2]1-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10]-1:[#7;a:11]:[c:12]:[#7;a:13].[C;D1;H3:14]-[NH2;D1;+0:15]>>[#7;a:13]:[c:12]:[#7;a:11]:[c:10]1:[c:8](:[c:9]):[c;H0;D3;+0:6](=[O;D1;H0:7]):[n;H0;D3;+0:15](-[C;D1;H3:14]):[cH;D2;+0:1]:[c;H0;D3;+0:2]:1-[... | null | [] | null | null | null | null | From 17e and methylamine, as for 18d except that, after reaction, the volatiles were removed at reduced pressure and water was added. The resultant suspension was stirred and basified with 10% sodium hydroxide, then acidified with concentrated hydrochloric acid (dropwise) and the brown solid was filtered to give 18y, m... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Anhydride.Primary amine | Carboxylic acid | c1cnc2nc3c(cc2c1)COCC3 | c1cnc2nc3ccncc3cc2c1 | c1cnc2nc3ccncc3cc2c1 | Other | null | null | null | CN.CN(C)C=C1C(=O)OC(=O)c2cc3cccnc3nc21>>Cn1cc(C(=O)O)c2nc3ncccc3cc2c1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-be1f33b239d846cb9ce9363f7b3b5692 | CN.CN(C)C=C1C(=O)OC(=O)c2nc3ccccc3nc21>>Cn1cc(C(=O)O)c2nc3ccccc3nc2c1=O | CN(C)C=C1C(OC(C2=NC3=CC=CC=C3N=C21)=O)=O.CN>>CN1C(C2=NC3=CC=CC=C3N=C2C(=C1)C(=O)O)=O | [CH3:1][NH2:2].CN(C)[CH:3]=[C:4]1[C:5](=[O:6])[O:7][C:18](=[O:19])[c:17]2[c:8]1[n:9][c:15]1[c:10]([cH:11][cH:12][cH:13][cH:14]1)[n:16]2>>[CH3:1][n:2]1[cH:3][c:4]([C:5](=[O:6])[OH:7])[c:8]2[n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[n:16][c:17]2[c:18]1=[O:19] | CN.CN(C)C=C1C(=O)OC(=O)c2nc3ccccc3nc21 | Cn1cc(C(=O)O)c2nc3ccccc3nc2c1=O | null | null | null | Miscellaneous | OtherReaction | e0306a5a26ce9da111d9319c59c0d97511d8e9e84da4c4b96f5262ed0d72c318 | 65cd6a35c5b072a8fab6ba6647692237b7343907b15b8d5326ebeac4c8a69aaa | O=c1[nH]ccc2nc3ccccc3nc12 | C-N(-C)-[CH;D2;+0:1]=[C;H0;D3;+0:2]1-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8]2:[n;H0;D2;+0:9]:[c;H0;D3;+0:10]3:[c:11]:[c:12]:[c:13]:[c:14]:[c;H0;D3;+0:15]:3:[n;H0;D2;+0:16]:[c:17]:2-1.[C;D1;H3:18]-[NH2;D1;+0:19]>>[C;D1;H3:18]-[n;H0;D3;+0:19]1:[cH;D2;+0:1]:[c;H0;D3;+0:2](-[C:3](=[O;D1;H0:4])... | null | [] | null | null | null | null | From 17d and methylamine, as for 18d except that, after reaction, the volatiles were removed at reduced pressure to leave the methylamine salt of 18z as a yellow-brown solid. This was suspended in a small amount of water and 10% sodium hydroxide was added dropwise, with stirring, until a solution was obtained. This was... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Anhydride.Primary amine | Carboxylic acid | c1ccc2nc3c(nc2c1)CCOC3 | c1ccc2nc3cnccc3nc2c1 | c1ccc2nc3cnccc3nc2c1 | Other | null | null | null | CN.CN(C)C=C1C(=O)OC(=O)c2nc3ccccc3nc21>>Cn1cc(C(=O)O)c2nc3ccccc3nc2c1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b9f74c0ecd3c4190be12e42e72312709 | COc1ccc(NC=C2C(=O)OC(=O)c3cc4cccc(C)c4nc32)cc1OC>>COc1ccc(-n2cc(C(=O)O)c3nc4c(C)cccc4cc3c2=O)cc1OC | COC=1C=C(C=CC1OC)NC=C1C(OC(C=2C1=NC=1C(=CC=CC1C2)C)=O)=O.NC=1C=C(C(=CC1)OC)OC.N1=CC=CC=C1>>COC=1C=C(C=CC1OC)N1C(C=2C=C3C(=NC2C(=C1)C(=O)O)C(=CC=C3)C)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][CH:8]=[C:9]2[C:10](=[O:11])[O:12][C:24](=[O:25])[c:23]3[c:13]2[n:14][c:15]2[c:16]([CH3:17])[cH:18][cH:19][cH:20][c:21]2[cH:22]3)[cH:26][c:27]1[O:28][CH3:29]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[n:7]2[cH:8][c:9]([C:10](=[O:11])[OH:12])[c:13]3[n:14][c:15]4[c:16]([CH3:17])[cH:1... | COc1ccc(NC=C2C(=O)OC(=O)c3cc4cccc(C)c4nc32)cc1OC | COc1ccc(-n2cc(C(=O)O)c3nc4c(C)cccc4cc3c2=O)cc1OC | null | null | C(C)N(CC)CC | Reduction | OtherReaction | 0746e8dd961ecb7eae2f8c98d4db129ba0e1364a432b1ea6c00105e672425619 | 82f28a85175c0de46fd64faeed18aba4de729d58744de685a258477aff26ad59 | O=c1c2cc3ccccc3nc2ccn1-c1ccccc1 | [O;D1;H0:1]=[C:2]1-[O;H0;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6](:[c:7]):[c:8](:[#7;a:9]:[c:10])-[C;H0;D3;+0:11]-1=[CH;D2;+0:12]-[NH;D2;+0:13]-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17]:[c:18]>>[O;D1;H0:1]=[C:2](-[OH;D1;+0:3])-[c;H0;D3;+0:11]1:[cH;D2;+0:12]:[n;H0;D3;+0:13](-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17]:[c:18]... | 78.3 | [{"value": 78.0, "product": "COC=1C=C(C=CC1OC)N1C(C=2C=C3C(=NC2C(=C1)C(=O)O)C(=CC=C3)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.3, "product": "COC=1C=C(C=CC1OC)N1C(C=2C=C3C(=NC2C(=C1)C(=O)O)C(=CC=C3)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of 19 (0.23 g), 4-aminoveratrole (0.46 g), pyridine (15 mL) and triethylamine (1 mL) was heated under reflux for 8 h (dissolution occurred during the heating). The reaction mixture was allowed to stand at −10° C. overnight and the resulting precipitate was collected by filtration and washed with a little cold... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Anhydride | Carboxylic acid | c1ccc2nc3c(cc2c1)COCC3 | c1ccc2nc3ccncc3cc2c1 | c1ccccc1.c1ccc2nc3ccncc3cc2c1 | null | C(C)N(CC)CC | null | 8 | COc1ccc(NC=C2C(=O)OC(=O)c3cc4cccc(C)c4nc32)cc1OC>C(C)N(CC)CC>COc1ccc(-n2cc(C(=O)O)c3nc4c(C)cccc4cc3c2=O)cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d491207662d941299d86e4fb23131f2a | CCOC(=O)Cn1cc(C(=O)O)c2nc3c(C)cccc3cc2c1=O.O=C(n1ccnc1)n1ccnc1>>CCOC(=O)Cn1cc(C(=O)NCCN(C)C)c2nc3c(C)cccc3cc2c1=O | C(C)OC(=O)CN1C(C=2C=C3C(=NC2C(=C1)C(=O)O)C(=CC=C3)C)=O.C1=CN(C=N1)C(=O)N2C=CN=C2>>CN(CCNC(=O)C1=CN(C(C=2C=C3C(=NC12)C(=CC=C3)C)=O)CC(=O)OCC)C | O[C:10]([c:9]1[cH:8][n:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:29](=[O:30])[c:28]2[c:18]1[n:19][c:20]1[c:21]([CH3:22])[cH:23][cH:24][cH:25][c:26]1[cH:27]2)=[O:11].O=C(n1ccn[cH:17]1)[n:12]1[cH:13][cH:14][n:15][cH:16]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][n:7]1[cH:8][c:9]([C:10](=[O:11])[NH:12][CH2:13][CH2:14][... | CCOC(=O)Cn1cc(C(=O)O)c2nc3c(C)cccc3cc2c1=O.O=C(n1ccnc1)n1ccnc1 | CCOC(=O)Cn1cc(C(=O)NCCN(C)C)c2nc3c(C)cccc3cc2c1=O | null | null | C(C)#N | Acylation | OtherReaction | 2331df1b12f4513d3c65a8ae1d0e61aa00ab339cf3395240712f135f81f53dd5 | 9f7b91a587de14909e1c407ad913e65eab279b0eab1bb69ba6c73d6ff2c55c0b | O=c1[nH]ccc2nc3ccccc3cc12 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5](-[C:6]-[C:7](-[#8:8])=[O;D1;H0:9]):[c:10]:[c:11]:[c:12]:1:[#7;a:13]:[c:14].O=C(-[n;H0;D3;+0:15]1:[cH;D2;+0:16]:[cH;D2;+0:17]:[n;H0;D2;+0:18]:[cH;D2;+0:19]:1)-n1:[cH;D2;+0:20]:n:c:c:1>>[#8:8]-[C:7](=[O;D1;H0:9])-[C:6]-[#7;a:5]1:[c:10]:[c:11]:[c:12](:[#7;a:13]:[c:14]):... | 79 | [{"value": 79.0, "product": "CN(CCNC(=O)C1=CN(C(C=2C=C3C(=NC12)C(=CC=C3)C)=O)CC(=O)OCC)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | From acid 18i with a reflux time of 48 h and a recharge with an equal amount of CDI after 24 h, and obtained as a yellow solid (79%), mp 214-215° C. (from acetonitrile). 1H NMR (CDCl3): δ 1.28 (t, J=7.2 Hz, 3H, CO2CH2CH3), 2.29 [s, 6H, N(CH3)2], 2.62 (t, J=6.4 Hz, 2H, CH2CH2NMe2), 2.87 (s, 3H, ArCH3), 3.72 (q, J=5.9 Hz... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Secondary amide.Tertiary amine | c1c[nH]cn1.c1c[nH]cn1 | null | c1ccc2nc3ccncc3cc2c1 | Other | C(C)#N | null | null | CCOC(=O)Cn1cc(C(=O)O)c2nc3c(C)cccc3cc2c1=O.O=C(n1ccnc1)n1ccnc1>C(C)#N>CCOC(=O)Cn1cc(C(=O)NCCN(C)C)c2nc3c(C)cccc3cc2c1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-81d125d897ad43d9b4a7e449f8ee8a48 | Cc1cccc2cc3c(=O)n(-c4ccc(B5OC(C)(C)C(C)(C)O5)cc4)cc(C(=O)O)c3nc12.O=C(n1ccnc1)n1ccnc1>>Cc1cccc2cc3c(=O)n(-c4ccc(B5OC(C)(C)C(C)(C)O5)cc4)cc(C(=O)NCCN(C)C)c3nc12 | CC1=CC=CC=2C1=NC=1C(=CN(C(C1C2)=O)C2=CC=C(C=C2)B2OC(C(O2)(C)C)(C)C)C(=O)O.C1=CN(C=N1)C(=O)N2C=CN=C2>>CN(CCNC(=O)C1=CN(C(C=2C=C3C(=NC12)C(=CC=C3)C)=O)C3=CC=C(C=C3)B3OC(C(O3)(C)C)(C)C)C | O[C:29]([c:28]1[cH:27][n:11](-[c:12]2[cH:13][cH:14][c:15]([B:16]3[O:17][C:18]([CH3:19])([CH3:20])[C:21]([CH3:22])([CH3:23])[O:24]3)[cH:25][cH:26]2)[c:9](=[O:10])[c:8]2[cH:7][c:6]3[cH:5][cH:4][cH:3][c:2]([CH3:1])[c:39]3[n:38][c:37]21)=[O:30].O=C(n1ccn[cH:36]1)[n:31]1[cH:32][cH:33][n:34][cH:35]1>>[CH3:1][c:2]1[cH:3][cH:4... | Cc1cccc2cc3c(=O)n(-c4ccc(B5OC(C)(C)C(C)(C)O5)cc4)cc(C(=O)O)c3nc12.O=C(n1ccnc1)n1ccnc1 | Cc1cccc2cc3c(=O)n(-c4ccc(B5OC(C)(C)C(C)(C)O5)cc4)cc(C(=O)NCCN(C)C)c3nc12 | null | null | null | Acylation | OtherReaction | 2331df1b12f4513d3c65a8ae1d0e61aa00ab339cf3395240712f135f81f53dd5 | 9f7b91a587de14909e1c407ad913e65eab279b0eab1bb69ba6c73d6ff2c55c0b | O=c1c2cc3ccccc3nc2ccn1-c1ccc(B2OCCO2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5](-[c:6]):[c:7]:[c:8]:[c:9]:1:[#7;a:10]:[c:11].O=C(-[n;H0;D3;+0:12]1:[cH;D2;+0:13]:[cH;D2;+0:14]:[n;H0;D2;+0:15]:[cH;D2;+0:16]:1)-n1:[cH;D2;+0:17]:n:c:c:1>>[CH3;D1;+0:16]-[N;H0;D3;+0:15](-[CH3;D1;+0:17])-[CH2;D2;+0:14]-[CH2;D2;+0:13]-[NH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1... | 74 | [{"value": 74.0, "product": "CN(CCNC(=O)C1=CN(C(C=2C=C3C(=NC12)C(=CC=C3)C)=O)C3=CC=C(C=C3)B3OC(C(O3)(C)C)(C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | From acid 18p, carried out under nitrogen, with a reflux time of 48 h and a recharge with an equal amount of CDI after 24 h. When the amination reaction was complete, the volatiles were removed at reduced pressure with heat (−0.3 mmHg, 100° C., 20 min) and residual N,N-dimethylethylenediamine was removed by azeotropic ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Secondary amide.Tertiary amine | c1c[nH]cn1.c1c[nH]cn1 | null | c1ccc2nc3ccncc3cc2c1.c1ccccc1.[B]1OCCO1 | Other | null | 100 | null | Cc1cccc2cc3c(=O)n(-c4ccc(B5OC(C)(C)C(C)(C)O5)cc4)cc(C(=O)O)c3nc12.O=C(n1ccnc1)n1ccnc1>>Cc1cccc2cc3c(=O)n(-c4ccc(B5OC(C)(C)C(C)(C)O5)cc4)cc(C(=O)NCCN(C)C)c3nc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ecc8105a4410432586f68ea2c5c93a5c | COc1ccc(Cn2cc(C(=O)O)c3nc4c(C)cccc4cc3c2=O)cc1OC.O=C(n1ccnc1)n1ccnc1>>COc1ccc(Cn2cc(C(=O)NCCN(C)C)c3nc4c(C)cccc4cc3c2=O)cc1OC | COC=1C=C(CN2C(C=3C=C4C(=NC3C(=C2)C(=O)O)C(=CC=C4)C)=O)C=CC1OC.C1=CN(C=N1)C(=O)N2C=CN=C2>>CN(CCNC(=O)C1=CN(C(C=2C=C3C(=NC12)C(=CC=C3)C)=O)CC3=CC(=C(C=C3)OC)OC)C | O[C:11]([c:10]1[cH:9][n:8]([CH2:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:33]([O:34][CH3:35])[cH:32]2)[c:30](=[O:31])[c:29]2[c:19]1[n:20][c:21]1[c:22]([CH3:23])[cH:24][cH:25][cH:26][c:27]1[cH:28]2)=[O:12].O=C(n1c[cH:15][n:16][cH:17]1)n1c[cH:14][n:13][cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][n:8]2[cH:9][c:10... | COc1ccc(Cn2cc(C(=O)O)c3nc4c(C)cccc4cc3c2=O)cc1OC.O=C(n1ccnc1)n1ccnc1 | COc1ccc(Cn2cc(C(=O)NCCN(C)C)c3nc4c(C)cccc4cc3c2=O)cc1OC | null | null | C(C)#N | Acylation | OtherReaction | 2331df1b12f4513d3c65a8ae1d0e61aa00ab339cf3395240712f135f81f53dd5 | 9f7b91a587de14909e1c407ad913e65eab279b0eab1bb69ba6c73d6ff2c55c0b | O=c1c2cc3ccccc3nc2ccn1Cc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5](-[C:6]):[c:7]:[c:8]:[c:9]:1:[#7;a:10]:[c:11].O=C(-n1:[cH;D2;+0:12]:[n;H0;D2;+0:13]:[cH;D2;+0:14]:c:1)-n1:[cH;D2;+0:15]:[n;H0;D2;+0:16]:[cH;D2;+0:17]:c:1>>[C:6]-[#7;a:5]1:[c:7]:[c:8]:[c:9](:[#7;a:10]:[c:11]):[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:16]-[CH2;D2;+0... | 85 | [{"value": 85.0, "product": "CN(CCNC(=O)C1=CN(C(C=2C=C3C(=NC12)C(=CC=C3)C)=O)CC3=CC(=C(C=C3)OC)OC)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | From acid 18r with a reflux time of 48 h and a recharge with an equal amount of CDI after 24 h, and obtained as a yellow solid (85%), mp 213-214° C. (from acetonitrile). 1H NMR (CDCl3): δ 2.22 [s, 6H, N(CH3)21, 2.52 (t, J=6.4 Hz, 2H, CH2CH2NMe2), 2.63 (s, 3H, ArCH3), 3.62 (q, J=6.1 Hz, 2H, CH2CH2NMe2), 3.75 (s, 3H, OCH... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Secondary amide.Tertiary amine | c1c[nH]cn1.c1c[nH]cn1 | null | c1ccccc1.c1ccc2nc3ccncc3cc2c1 | Other | C(C)#N | null | null | COc1ccc(Cn2cc(C(=O)O)c3nc4c(C)cccc4cc3c2=O)cc1OC.O=C(n1ccnc1)n1ccnc1>C(C)#N>COc1ccc(Cn2cc(C(=O)NCCN(C)C)c3nc4c(C)cccc4cc3c2=O)cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ee4298bb91dd46e483caffa5d4745355 | COc1ccc(CCn2cc(C(=O)O)c3nc4c(C)cccc4cc3c2=O)cc1OC.O=C(n1ccnc1)n1ccnc1>>COc1ccc(CCn2cc(C(=O)NCCN(C)C)c3nc4c(C)cccc4cc3c2=O)cc1OC | COC=1C=C(C=CC1OC)CCN1C(C=2C=C3C(=NC2C(=C1)C(=O)O)C(=CC=C3)C)=O.C1=CN(C=N1)C(=O)N2C=CN=C2>>CN(CCNC(=O)C1=CN(C(C=2C=C3C(=NC12)C(=CC=C3)C)=O)CCC3=CC(=C(C=C3)OC)OC)C | O[C:12]([c:11]1[cH:10][n:9]([CH2:8][CH2:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:34]([O:35][CH3:36])[cH:33]2)[c:31](=[O:32])[c:30]2[c:20]1[n:21][c:22]1[c:23]([CH3:24])[cH:25][cH:26][cH:27][c:28]1[cH:29]2)=[O:13].O=C(n1ccn[cH:19]1)[n:14]1[cH:15][cH:16][n:17][cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][n... | COc1ccc(CCn2cc(C(=O)O)c3nc4c(C)cccc4cc3c2=O)cc1OC.O=C(n1ccnc1)n1ccnc1 | COc1ccc(CCn2cc(C(=O)NCCN(C)C)c3nc4c(C)cccc4cc3c2=O)cc1OC | null | null | C(C)#N | Acylation | OtherReaction | 2331df1b12f4513d3c65a8ae1d0e61aa00ab339cf3395240712f135f81f53dd5 | 9f7b91a587de14909e1c407ad913e65eab279b0eab1bb69ba6c73d6ff2c55c0b | O=c1c2cc3ccccc3nc2ccn1CCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5](-[C:6]):[c:7]:[c:8]:[c:9]:1:[#7;a:10]:[c:11].O=C(-[n;H0;D3;+0:12]1:[cH;D2;+0:13]:[cH;D2;+0:14]:[n;H0;D2;+0:15]:[cH;D2;+0:16]:1)-n1:[cH;D2;+0:17]:n:c:c:1>>[C:6]-[#7;a:5]1:[c:4]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:12]-[CH2;D2;+0:13]-[CH2;D2;+0:14]-[N;H0;D3;+0... | 81 | [{"value": 81.0, "product": "CN(CCNC(=O)C1=CN(C(C=2C=C3C(=NC12)C(=CC=C3)C)=O)CCC3=CC(=C(C=C3)OC)OC)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | From acid 18s with a reflux time of 48 h and a recharge with an equal amount of CDI after 24 h, and obtained as a yellow solid (81%), mp 113-114° C. (from acetonitrile). 1H NMR (CDCl3): δ 2.26 [s, 6H, N(CH3)2], 2.58 (t, J=6.5 Hz, 2H, CH2CH2NMe2), 2.77 (s, 3H, ArCH3), 3.01 (m, 2H, CH2CH2Ph), 3.67 (q, J=6.1 Hz, 2H, CH2CH... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Secondary amide.Tertiary amine | c1c[nH]cn1.c1c[nH]cn1 | null | c1ccccc1.c1ccc2nc3ccncc3cc2c1 | Other | C(C)#N | null | null | COc1ccc(CCn2cc(C(=O)O)c3nc4c(C)cccc4cc3c2=O)cc1OC.O=C(n1ccnc1)n1ccnc1>C(C)#N>COc1ccc(CCn2cc(C(=O)NCCN(C)C)c3nc4c(C)cccc4cc3c2=O)cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3434aa35b32a4373aabfc97172b9b4ca | Cc1cccc2cc3c(=O)n(Cc4ccccn4)cc(C(=O)O)c3nc12.O=C(n1ccnc1)n1ccnc1>>Cc1cccc2cc3c(=O)n(Cc4ccccn4)cc(C(=O)NCCN(C)C)c3nc12 | CC1=CC=CC=2C1=NC=1C(=CN(C(C1C2)=O)CC2=NC=CC=C2)C(=O)O.C1=CN(C=N1)C(=O)N2C=CN=C2>>CN(CCNC(=O)C1=CN(C(C=2C=C3C(=NC12)C(=CC=C3)C)=O)CC3=NC=CC=C3)C | O[C:21]([c:20]1[cH:19][n:11]([CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][n:18]2)[c:9](=[O:10])[c:8]2[cH:7][c:6]3[cH:5][cH:4][cH:3][c:2]([CH3:1])[c:31]3[n:30][c:29]21)=[O:22].O=C(n1ccn[cH:28]1)[n:23]1[cH:24][cH:25][n:26][cH:27]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[cH:7][c:8]3[c:9](=[O:10])[n:11]([CH2:12][c:13]4[cH:14... | Cc1cccc2cc3c(=O)n(Cc4ccccn4)cc(C(=O)O)c3nc12.O=C(n1ccnc1)n1ccnc1 | Cc1cccc2cc3c(=O)n(Cc4ccccn4)cc(C(=O)NCCN(C)C)c3nc12 | null | null | C(C)#N | Acylation | OtherReaction | 2331df1b12f4513d3c65a8ae1d0e61aa00ab339cf3395240712f135f81f53dd5 | 9f7b91a587de14909e1c407ad913e65eab279b0eab1bb69ba6c73d6ff2c55c0b | O=c1c2cc3ccccc3nc2ccn1Cc1ccccn1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5](-[C:6]):[c:7]:[c:8]:[c:9]:1:[#7;a:10]:[c:11].O=C(-[n;H0;D3;+0:12]1:[cH;D2;+0:13]:[cH;D2;+0:14]:[n;H0;D2;+0:15]:[cH;D2;+0:16]:1)-n1:[cH;D2;+0:17]:n:c:c:1>>[C:6]-[#7;a:5]1:[c:4]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:12]-[CH2;D2;+0:13]-[CH2;D2;+0:14]-[N;H0;D3;+0... | 75 | [{"value": 75.0, "product": "CN(CCNC(=O)C1=CN(C(C=2C=C3C(=NC12)C(=CC=C3)C)=O)CC3=NC=CC=C3)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | From acid 18t, with a reflux time of 48 h and a recharge with an equal amount of CDI after 24 h, and obtained as a bright yellow solid (75%), mp 183-184° C., (from acetonitrile). 1H NMR (CDCl3): δ 2.25 [s, 6H, N(CH3)2], 2.57 (t, J=6.4 Hz, 2H, CH2CH2NMe2), 2.67 (s, 3H, ArCH3), 3.66 (q, J=6.1 Hz, CH2, CH2CH2NMe2), 5.30 (... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Secondary amide.Tertiary amine | c1c[nH]cn1.c1c[nH]cn1 | null | c1ccc2nc3ccncc3cc2c1.c1ccncc1 | Other | C(C)#N | null | null | Cc1cccc2cc3c(=O)n(Cc4ccccn4)cc(C(=O)O)c3nc12.O=C(n1ccnc1)n1ccnc1>C(C)#N>Cc1cccc2cc3c(=O)n(Cc4ccccn4)cc(C(=O)NCCN(C)C)c3nc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b84d4300df014e45a6e06a983e66eb4a | COc1ccc2cc3c(=O)n(C)cc(C(=O)O)c3nc2c1.O=C(n1ccnc1)n1ccnc1>>COc1ccc2cc3c(=O)n(C)cc(C(=O)NCCN(C)C)c3nc2c1 | COC=1C=CC=2C(=NC=3C(=CN(C(C3C2)=O)C)C(=O)O)C1.C1=CN(C=N1)C(=O)N2C=CN=C2>>CN(CCNC(=O)C1=CN(C(C=2C=C3C(=NC12)C=C(C=C3)OC)=O)C)C | O[C:15]([c:14]1[cH:13][n:11]([CH3:12])[c:9](=[O:10])[c:8]2[cH:7][c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:26][c:25]3[n:24][c:23]21)=[O:16].O=C(n1ccn[cH:22]1)[n:17]1[cH:18][cH:19][n:20][cH:21]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][c:8]3[c:9](=[O:10])[n:11]([CH3:12])[cH:13][c:14]([C:15](=[O:16])[NH:17][CH2:18][CH2:... | COc1ccc2cc3c(=O)n(C)cc(C(=O)O)c3nc2c1.O=C(n1ccnc1)n1ccnc1 | COc1ccc2cc3c(=O)n(C)cc(C(=O)NCCN(C)C)c3nc2c1 | null | null | C(C)#N | Acylation | OtherReaction | 2331df1b12f4513d3c65a8ae1d0e61aa00ab339cf3395240712f135f81f53dd5 | 9f7b91a587de14909e1c407ad913e65eab279b0eab1bb69ba6c73d6ff2c55c0b | O=c1[nH]ccc2nc3ccccc3cc12 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5](-[C;D1;H3:6]):[c:7]:[c:8]:[c:9]:1:[#7;a:10]:[c:11].O=C(-[n;H0;D3;+0:12]1:[cH;D2;+0:13]:[cH;D2;+0:14]:[n;H0;D2;+0:15]:[cH;D2;+0:16]:1)-n1:[cH;D2;+0:17]:n:c:c:1>>[C;D1;H3:6]-[#7;a:5]1:[c:4]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:12]-[CH2;D2;+0:13]-[CH2;D2;+0:14]... | 80 | [{"value": 80.0, "product": "CN(CCNC(=O)C1=CN(C(C=2C=C3C(=NC12)C=C(C=C3)OC)=O)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | From acid 18w, with a reflux time of 96 h and a recharge with an equal amount of CDI after 48 h, and obtained as a yellow solid (80%), mp 213-215° C. (from acetonitrile). 1H NMR (CDCl3): δ 2.50 [s, 6H, N(CH3)2], 2.78 (t, J=6.0 Hz, 2H, CH2CH2NMe2), 3.67 (s, 3H, NCH3), 3.77 (q, J=5.8 Hz, 2H, CH2CH2NMe2), 4.02 (s, 3H, ArO... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Secondary amide.Tertiary amine | c1c[nH]cn1.c1c[nH]cn1 | null | c1ccc2nc3ccncc3cc2c1 | Other | C(C)#N | null | null | COc1ccc2cc3c(=O)n(C)cc(C(=O)O)c3nc2c1.O=C(n1ccnc1)n1ccnc1>C(C)#N>COc1ccc2cc3c(=O)n(C)cc(C(=O)NCCN(C)C)c3nc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2680ae286fb04a19bde451735abd188d | Cc1cccc2cc3c(=O)n(CCc4cn(C(=O)NCCN(C)C)c5ccccc45)cc(C(=O)NCCN(C)C)c3nc12>>Cc1cccc2cc3c(=O)n(CCc4c[nH]c5ccccc45)cc(C(=O)NCCN(C)C)c3nc12 | CN(CCNC(=O)C1=CN(C(C=2C=C3C(=NC12)C(=CC=C3)C)=O)CCC3=CN(C1=CC=CC=C31)C(=O)NCCN(C)C)C.[OH-].[Na+]>>CN(CCNC(=O)C1=CN(C(C=2C=C3C(=NC12)C(=CC=C3)C)=O)CCC3=CNC1=CC=CC=C31)C | CN(C)CCNC(=O)[n:16]1[cH:15][c:14]([CH2:13][CH2:12][n:11]2[c:9](=[O:10])[c:8]3[cH:7][c:6]4[cH:5][cH:4][cH:3][c:2]([CH3:1])[c:35]4[n:34][c:33]3[c:24]([C:25](=[O:26])[NH:27][CH2:28][CH2:29][N:30]([CH3:31])[CH3:32])[cH:23]2)[c:22]2[c:17]1[cH:18][cH:19][cH:20][cH:21]2>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[cH:7][c:8]3[c:9](... | Cc1cccc2cc3c(=O)n(CCc4cn(C(=O)NCCN(C)C)c5ccccc45)cc(C(=O)NCCN(C)C)c3nc12 | Cc1cccc2cc3c(=O)n(CCc4c[nH]c5ccccc45)cc(C(=O)NCCN(C)C)c3nc12 | null | null | C(C)O | Reduction | OtherReaction | 3b1608d951299ab048b4c7e0ed308df6e0193467fdd2fece3a1bfc0f6e2ad272 | f3fa0ef63fec410a570c0fa9e065a8b3b32623d84cf4eee1bf5c03f01a2efbdd | O=c1c2cc3ccccc3nc2ccn1CCc1c[nH]c2ccccc12 | C-N(-C)-C-C-N-C(=O)-[n;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]:1:[c:6]>>[c:6]:[c:5]1:[c:4]:[c:3]:[c:2]:[nH;D2;+0:1]:1 | 90 | [{"value": 90.0, "product": "CN(CCNC(=O)C1=CN(C(C=2C=C3C(=NC12)C(=CC=C3)C)=O)CCC3=CNC1=CC=CC=C31)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.8, "product": "CN(CCNC(=O)C1=CN(C(C=2C=C3C(=NC12)C(=CC=C3)C)=O)CCC3=CNC1=CC=CC=C31)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a hot solution of the bisamide 21b (0.58 g, 1.00 mmol) in ethanol (10 mL) was added 10% sodium hydroxide (10 mL), and the whole was heated at reflux for 40 min. The reaction mixture was then evaporated to dryness under reduced pressure, water was added and the solid was filtered and washed with water to give 20v as ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Tertiary amine | null | c1c[nH]c2ccccc12 | c1ccc2[nH]ccc2c1 | c1ccc2nc3ccncc3cc2c1.c1ccc2[nH]ccc2c1 | HO- | C(C)O | null | null | Cc1cccc2cc3c(=O)n(CCc4cn(C(=O)NCCN(C)C)c5ccccc45)cc(C(=O)NCCN(C)C)c3nc12>C(C)O>Cc1cccc2cc3c(=O)n(CCc4c[nH]c5ccccc45)cc(C(=O)NCCN(C)C)c3nc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a75b3b61934a4a628d34262e480275d5 | NCCN(CCN)CCN.O=Cc1ccc(F)cc1>>Fc1ccc(CNCCN(CCNCc2ccc(F)cc2)CCNCc2ccc(F)cc2)cc1 | NCCN(CCN)CCN.FC1=CC=C(C=O)C=C1.[BH4-].[Na+]>>FC1=CC=C(CNCCN(CCNCC2=CC=C(C=C2)F)CCNCC2=CC=C(C=C2)F)C=C1 | [CH2:3]([NH2:7])[CH2:25][N:10]([CH2:11][CH2:12][NH2:13])[CH2:22][CH2:23][NH2:24].O=[CH:14][c:15]1[cH:16][cH:34][c:2]([F:1])[cH:31][cH:29]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][NH:7][CH2:8][CH2:9][N:10]([CH2:11][CH2:12][NH:13][CH2:14][c:15]2[cH:16][cH:17][c:18]([F:19])[cH:20][cH:21]2)[CH2:22][CH2:23][NH:24][CH2:25][c:2... | NCCN(CCN)CCN.O=Cc1ccc(F)cc1 | Fc1ccc(CNCCN(CCNCc2ccc(F)cc2)CCNCc2ccc(F)cc2)cc1 | null | null | [Cl-].[NH4+].C(Cl)Cl.CO | Aromatic Heterocycle Formation | OtherReaction | 6a1379183e3996a5070a40220566807b0b005c05bd56a480311ce3ae317a6dbd | c2fa50a45e6bd873f47d8c769fe65a45de41cca5b014c80e7f704cf077c282c7 | c1ccc(CNCCN(CCNCc2ccccc2)CCNCc2ccccc2)cc1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[F;D1;H0:6]):[cH;D2;+0:7]:[cH;D2;+0:8]:1.[NH2;D1;+0:9]-[C:10]-[C:11]-[N;H0;D3;+0:12](-[C:13]-[C:14]-[NH2;D1;+0:15])-[CH2;D2;+0:16]-[CH2;D2;+0:17]-[NH2;D1;+0:18]>>[F;D1;H0:6]-[c;H0;D3;+0:5]1:[cH;D2;+0:4]:[c:19]:[c:20](-[C:21]-[NH;D2;+0:18]-[C:22]-[... | null | [] | 25 | CELSIUS | 15 | HOUR | Tris(2-aminoethyl)amine (0.01 mol) and 4-fluoro-benzaldehyde (0.03 mol) were dissolved in MeOH (50 mL). After stirring at 25° C. for 15 h, NaBH4 (1.90 g, 0.05 mol) was added to the above solution at 0° C. The reaction mixture was stirred for 2 h at 25° C. It was then diluted with CH2Cl2 (100 mL) and ammonium chloride a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aldehyde.Primary amine.Primary amine.Primary amine.Tertiary amine | Aromatic halide.Aromatic halide.Aromatic halide.Secondary amine.Secondary amine.Secondary amine.Tertiary amine | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | null | [Cl-].[NH4+].C(Cl)Cl.CO | 25 | 15 | NCCN(CCN)CCN.O=Cc1ccc(F)cc1>[Cl-].[NH4+].C(Cl)Cl.CO>Fc1ccc(CNCCN(CCNCc2ccc(F)cc2)CCNCc2ccc(F)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c001bf39cddb49e79b8162bc550037a2 | CC(=O)c1ccccn1.[BH4-]>>O=Cc1ccccn1.[BH4-] | C(C)(C)(C)OC(=O)NCCN(CCNC(=O)OC(C)(C)C)C1=C(C=CC(=C1)C)C#N.[BH4-].[Na+].Cl.CCOCC.C(C)(=O)C1=NC=CC=C1>>N1=C(C=CC=C1)C=O.[BH4-].[Na+].Cl | C[C:3](=[O:2])[c:4]1[cH:5][cH:6][cH:7][cH:8][n:9]1.[BH4-:10]>>[O:2]=[CH:3][c:4]1[cH:5][cH:6][cH:7][cH:8][n:9]1.[BH4-:10] | CC(=O)c1ccccn1.[BH4-] | O=Cc1ccccn1.[BH4-] | null | null | CO | Miscellaneous | OtherReaction | d128dde730bbd2a7f6036aa76a14f5c180d17e1217ffbf8498660a9eb331e0b1 | e1a996a980c05a95ba76483af1ea6ca40e01362f40f9aedd88ba62d6b7e6693c | c1ccncc1 | C-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6]>>[O;D1;H0:2]=[CH;D2;+0:1]-[c:3](:[c:4]):[#7;a:5]:[c:6] | null | [] | null | null | null | null | The resultant bis(2-tert-butoxycarbonylaminoethyl)amino-4-methylphenylcyanide was deprotected using HCl/ether, condensed with 2-acetyl pyridine (0.01 mol) in MeOH, and then reduced by NaBH4. After sequential treatments with pyridine-2-carboxaldehyde, NaBH4, and HCl, compound 110 was obtained in 75% overall yield.
Condi... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Aldehyde | null | null | c1ccncc1 | Other | CO | null | null | CC(=O)c1ccccn1.[BH4-]>CO>O=Cc1ccccn1.[BH4-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2f44bf38eb3745459274ac3dbbeecdfa | CC(=O)c1ccc(C)c(C)c1.COC(=O)OC>>COC(=O)CC(=O)c1ccc(C)c(C)c1 | CC1=C(C=C(C=C1)C(=O)C)C.[K].Cl.COC(OC)=O>>COC(CC(=O)C1=CC(=C(C=C1)C)C)=O | [CH3:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([CH3:12])[c:13]([CH3:14])[cH:15]1.CO[C:3]([O:2][CH3:1])=[O:4]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([CH3:12])[c:13]([CH3:14])[cH:15]1 | CC(=O)c1ccc(C)c(C)c1.COC(=O)OC | COC(=O)CC(=O)c1ccc(C)c(C)c1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 984c35cff4b3f334715b1696c3f8f2fb17ccd67fc374fcef5afdd55b5aabecf9 | d76b6fc9d01d8258e5777a3b2326a8d78a9d9a55717b27736ba55600205f4ed0 | c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[C;D1;H3:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:5]-[C:6](=[O;D1;H0:7])-[c:8] | null | [] | null | null | 10 | MINUTE | To a stirring solution of 3,4-dimethylacetophenone (1.0 g, 6.8 mmol) in tetrahydrofuran (10 ML) at 0° C. under an atmosphere of nitrogen was added potassium hexamethyldisilylzide (1.46 g, 6.8 mmol). Resulting suspension was stirred for 10 min and dimethylcarbonate (0.58 mL, 6.8 mmol) added. Reaction stirred for 16 h wa... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Ketone | Ketone.Ester | null | null | c1ccccc1 | HO- | O1CCCC1 | null | 0.166667 | CC(=O)c1ccc(C)c(C)c1.COC(=O)OC>O1CCCC1>COC(=O)CC(=O)c1ccc(C)c(C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b492962599464687b8ecb21ef57a55d3 | COC(=O)CC(=O)c1ccc(C)c(C)c1.N=C1NCCCN1>>Cc1ccc(-c2cc(=O)n3c(n2)NCCC3)cc1C | O.COC(CC(=O)C1=CC(=C(C=C1)C)C)=O.Cl.N1C(NCCC1)=N.C([O-])([O-])=O.[K+].[K+]>>CC=1C=C(C=CC1C)C=1N=C2N(C(C1)=O)CCCN2 | CO[C:8]([CH2:7][C:6](=O)[c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:18]([CH3:19])[cH:17]1)=[O:9].[NH:10]1[C:11](=[NH:12])[NH:13][CH2:14][CH2:15][CH2:16]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8](=[O:9])[n:10]3[c:11]([n:12]2)[NH:13][CH2:14][CH2:15][CH2:16]3)[cH:17][c:18]1[CH3:19] | COC(=O)CC(=O)c1ccc(C)c(C)c1.N=C1NCCCN1 | Cc1ccc(-c2cc(=O)n3c(n2)NCCC3)cc1C | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 8854a779ae6c83f2473550e3161491ed1f51a75ff7329df6e7bd303a33a54aee | f590641b01cb525446469ed6ced5b738f453feb2f025056e9767d27c06e94b8b | O=c1cc(-c2ccccc2)nc2n1CCCN2 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[C;H0;D3;+0:4](=O)-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11]1-[#7:12]-[C:13]-[C:14]-[C:15]-[NH;D2;+0:16]-1>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[cH;D2;+0:3]:[c;H0;D3;+0:4](-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8]:[c:9]):[n;H0;D2;+0:10]:[c;H0;D3;+0:11]2:[n;H... | null | [] | null | null | null | null | A suspension of 3-(3,4-dimethyl-phenyl)-3-oxo-propionic acid methyl ester (1.2 g, 5.8 mmol), tetrahydro-pyrimidin-2-ylideneamine hydrochloride (0.78 g, 5.8 mmol), and potassium carbonate (0.80 g, 5.8 mmol) in ethanol (20 mL) was heated to reflux for 4 h. Water (5 mL) was added to the reaction at room temperature and ta... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Secondary amine | null | C1CNCNC1 | c1ccn2c(n1)NCCC2 | c1ccccc1.c1ccn2c(n1)NCCC2 | HO- | C(C)O | null | null | COC(=O)CC(=O)c1ccc(C)c(C)c1.N=C1NCCCN1>C(C)O>Cc1ccc(-c2cc(=O)n3c(n2)NCCC3)cc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f32cf1765b564eff980403959051d5ac | CSc1nccc(N2CCCn3c2nc(-c2ccccc2)cc3=O)n1.O=[N+]=O>>CSc1nccc(N2CCCn3c2nc(-c2ccccc2)c([N+](=O)[O-])c3=O)n1 | CSC1=NC=CC(=N1)N1CCCN2C1=NC(=CC2=O)C2=CC=CC=C2.F[B-](F)(F)F.O=[N+]=O>>CSC1=NC=CC(=N1)N1CCCN2C1=NC(=C(C2=O)[N+](=O)[O-])C2=CC=CC=C2 | [CH3:1][S:2][c:3]1[n:4][cH:5][cH:6][c:7]([N:8]2[CH2:9][CH2:10][CH2:11][n:12]3[c:13]2[n:14][c:15](-[c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[cH:22][c:26]3=[O:27])[n:28]1.[N+:23](=[O:24])=[O:25]>>[CH3:1][S:2][c:3]1[n:4][cH:5][cH:6][c:7]([N:8]2[CH2:9][CH2:10][CH2:11][n:12]3[c:13]2[n:14][c:15](-[c:16]2[cH:17][cH:18][cH:... | CSc1nccc(N2CCCn3c2nc(-c2ccccc2)cc3=O)n1.O=[N+]=O | CSc1nccc(N2CCCn3c2nc(-c2ccccc2)c([N+](=O)[O-])c3=O)n1 | null | null | ClCCl | Functional Group Addition | OtherReaction | 1e02b01ecda1eb175a9b37fb4f8fcfc905a0e59356acc23ab666bea8a1d2e177 | 5c75a9bf759be9717d985245c85c84dbfff904ea5287869736b84fdaa57f1e27 | O=c1cc(-c2ccccc2)nc2n1CCCN2c1ccncn1 | [#7:1]-[c:2]1:[#7;a:3]:[c:4](-[c:5]):[cH;D2;+0:6]:[c:7](=[O;D1;H0:8]):[#7;a:9]:1-[C:10].[O;D1;H0:11]=[N+;H0;D2:12]=[O;H0;D1;+0:13]>>[#7:1]-[c:2]1:[#7;a:3]:[c:4](-[c:5]):[c;H0;D3;+0:6](-[N+;H0;D3:12](-[O-;H0;D1:13])=[O;D1;H0:11]):[c:7](=[O;D1;H0:8]):[#7;a:9]:1-[C:10] | null | [] | null | null | 1 | HOUR | To a stirring solution of 9-(2-methylsulfanyl-pyrimidin-4-yl)-2-phenyl-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one (500 mg, 1.42 mmol) in dichloromethane (10 mL) at 0° C. under nitrogen was added nitronium tetrafluoroborate in a 0.5M solution (7 mL, 3.55 mmol). External cooling removed and reaction warmed to room... | 10.6084/m9.figshare.5104873.v1 | null | Nitroso.Nitroso | Nitro group | c1ccn2c(n1)NCCC2 | c1cnc2n(c1)CCCN2 | c1cncnc1.c1cnc2n(c1)CCCN2.c1ccccc1 | null | ClCCl | null | 1 | CSc1nccc(N2CCCn3c2nc(-c2ccccc2)cc3=O)n1.O=[N+]=O>ClCCl>CSc1nccc(N2CCCn3c2nc(-c2ccccc2)c([N+](=O)[O-])c3=O)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fad58e800c124a41a2a52f05347cd69b | CS(=O)(=O)c1nccc(N2CCCn3c2nc(-c2ccccc2)c([N+](=O)[O-])c3=O)n1.NCCc1ccccc1>>O=c1c([N+](=O)[O-])c(-c2ccccc2)nc2n1CCCN2c1ccnc(NCCc2ccccc2)n1 | CS(=O)(=O)C1=NC=CC(=N1)N1CCCN2C1=NC(=C(C2=O)[N+](=O)[O-])C2=CC=CC=C2.C(CC1=CC=CC=C1)N>>[N+](=O)([O-])C1=C(N=C2N(C1=O)CCCN2C2=NC(=NC=C2)NCCC2=CC=CC=C2)C2=CC=CC=C2 | CS(=O)(=O)[c:25]1[n:24][cH:23][cH:22][c:21]([N:20]2[c:15]3[n:14][c:7](-[c:8]4[cH:9][cH:10][cH:11][cH:12][cH:13]4)[c:3]([N+:4](=[O:5])[O-:6])[c:2](=[O:1])[n:16]3[CH2:17][CH2:18][CH2:19]2)[n:35]1.[NH2:26][CH2:27][CH2:28][c:29]1[cH:30][cH:31][cH:32][cH:33][cH:34]1>>[O:1]=[c:2]1[c:3]([N+:4](=[O:5])[O-:6])[c:7](-[c:8]2[cH:9... | CS(=O)(=O)c1nccc(N2CCCn3c2nc(-c2ccccc2)c([N+](=O)[O-])c3=O)n1.NCCc1ccccc1 | O=c1c([N+](=O)[O-])c(-c2ccccc2)nc2n1CCCN2c1ccnc(NCCc2ccccc2)n1 | null | null | ClCCl | Functional Group Addition | OtherReaction | f2778420425e3c4d58f5c5ce2d21af9ae914e93cbdfd773daad65dd144fb98f8 | 1b70c6d90d02e3556760722fb8afbfe20a90609f96696f664c7b05b1d983c008 | O=c1cc(-c2ccccc2)nc2n1CCCN2c1ccnc(NCCc2ccccc2)n1 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | A solution of 9-(2-methanesulfonyl-pyrimidin-4-yl) -3-nitro-2-phenyl -6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one (220 mg, 0.51 mmol) and phenethylamine (0.13 mL, 1.0 mmol) in dichloromethane (2 mL) was heated to 80° C. for 1 h. Residue purified on silica, and final product isolated as a white solid. M+1=470.
Con... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cnc2n(c1)CCCN2.c1cncnc1.c1ccccc1 | HO- | ClCCl | null | null | CS(=O)(=O)c1nccc(N2CCCn3c2nc(-c2ccccc2)c([N+](=O)[O-])c3=O)n1.NCCc1ccccc1>ClCCl>O=c1c([N+](=O)[O-])c(-c2ccccc2)nc2n1CCCN2c1ccnc(NCCc2ccccc2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a43844c13103496dbf3e3f66108a136a | O=c1c([N+](=O)[O-])c(-c2ccccc2)nc2n1CCCN2c1ccnc(NCCc2ccccc2)n1>>Nc1c(-c2ccccc2)nc2n(c1=O)CCCN2c1ccnc(NCCc2ccccc2)n1 | [N+](=O)([O-])C1=C(N=C2N(C1=O)CCCN2C2=NC(=NC=C2)NCCC2=CC=CC=C2)C2=CC=CC=C2>>NC1=C(N=C2N(C1=O)CCCN2C2=NC(=NC=C2)NCCC2=CC=CC=C2)C2=CC=CC=C2 | O=[N+:1]([O-])[c:2]1[c:3](-[c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)[n:10][c:11]2[n:12]([c:13]1=[O:14])[CH2:15][CH2:16][CH2:17][N:18]2[c:19]1[cH:20][cH:21][n:22][c:23]([NH:24][CH2:25][CH2:26][c:27]2[cH:28][cH:29][cH:30][cH:31][cH:32]2)[n:33]1>>[NH2:1][c:2]1[c:3](-[c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)[n:10][c:11]2[n:12]([... | O=c1c([N+](=O)[O-])c(-c2ccccc2)nc2n1CCCN2c1ccnc(NCCc2ccccc2)n1 | Nc1c(-c2ccccc2)nc2n(c1=O)CCCN2c1ccnc(NCCc2ccccc2)n1 | null | [Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=c1cc(-c2ccccc2)nc2n1CCCN2c1ccnc(NCCc2ccccc2)n1 | O=[N+;H0;D3:1](-[O-])-[c:2]1:[c:3](=[O;D1;H0:4]):[#7;a:5](:[c:6](:[#7;a:7]:[c:8]:1-[c:9])-[#7:10])-[C:11]>>[#7:10]-[c:6]1:[#7;a:7]:[c:8](-[c:9]):[c:2](-[NH2;D1;+0:1]):[c:3](=[O;D1;H0:4]):[#7;a:5]:1-[C:11] | null | [] | null | null | null | null | A suspension of 3-nitro-9-(2-phenethylamino-pyrimidin -4-yl)-2-phenyl -6,7,8,9tetrahydro-pyrimido[1,2-a]pyrimidin-4-one (40 mg, 0.09 mmol) in methanol (10 mL) was stirred with 10 % palladium on carbon (5 mg) under an atmosphere of hydrogen for 4 h. Reaction mixture filtered through a bed of Celite, and final product is... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1cnc2n(c1)CCCN2.c1cncnc1.c1ccccc1 | Other | [Pd].CO | null | null | O=c1c([N+](=O)[O-])c(-c2ccccc2)nc2n1CCCN2c1ccnc(NCCc2ccccc2)n1>[Pd].CO>Nc1c(-c2ccccc2)nc2n(c1=O)CCCN2c1ccnc(NCCc2ccccc2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9476fd4ddc2340ed84f7afe148dc3f1e | CC(Cc1cccc(CN=[N+]=[N-])c1)Nc1nccc(N2CCCn3c2nc(-c2ccccc2)c([N+](=O)[O-])c3=O)n1>>CC(Cc1cccc(CN)c1)Nc1nccc(N2CCCn3c2nc(-c2ccccc2)c(N)c3=O)n1 | N(=[N+]=[N-])CC=1C=C(C=CC1)CC(C)NC1=NC=CC(=N1)N1CCCN2C1=NC(=C(C2=O)[N+](=O)[O-])C2=CC=CC=C2.[H][H]>>NC1=C(N=C2N(C1=O)CCCN2C2=NC(=NC=C2)NC(CC2=CC(=CC=C2)CN)C)C2=CC=CC=C2 | [N-]=[N+]=[N:10][CH2:9][c:8]1[cH:7][cH:6][cH:5][c:4]([CH2:3][CH:2]([CH3:1])[NH:12][c:13]2[n:14][cH:15][cH:16][c:17]([N:18]3[CH2:19][CH2:20][CH2:21][n:22]4[c:23]3[n:24][c:25](-[c:26]3[cH:27][cH:28][cH:29][cH:30][cH:31]3)[c:32]([N+:33](=O)[O-])[c:34]4=[O:35])[n:36]2)[cH:11]1>>[CH3:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7]... | CC(Cc1cccc(CN=[N+]=[N-])c1)Nc1nccc(N2CCCn3c2nc(-c2ccccc2)c([N+](=O)[O-])c3=O)n1 | CC(Cc1cccc(CN)c1)Nc1nccc(N2CCCn3c2nc(-c2ccccc2)c(N)c3=O)n1 | null | [Pd] | CO | Reduction | OtherReaction | 541ebc6861bc599b6e112bbd8dbbb07f240ba38b70136a42955c152c4fcaa7e9 | 7b30571693ddff2f058caf329f0303b5c67c194f41389a4af808fb0004d60fca | O=c1cc(-c2ccccc2)nc2n1CCCN2c1ccnc(NCCc2ccccc2)n1 | O=[N+;H0;D3:1](-[O-])-[c:2]1:[c:3](-[c:4]):[#7;a:5]:[c:6](:[#7;a:7](:[c:8]:1=[O;D1;H0:9])-[C:10])-[#7:11].[N-]=[N+]=[N;H0;D2;+0:12]-[C:13]-[c:14]>>[#7:11]-[c:6]1:[#7;a:5]:[c:3](-[c:4]):[c:2](-[NH2;D1;+0:1]):[c:8](=[O;D1;H0:9]):[#7;a:7]:1-[C:10].[NH2;D1;+0:12]-[C:13]-[c:14] | null | [] | null | null | 2 | HOUR | To a solution of 9-{2-[2-(3-azidomethyl-phenyl) -1-methyl-ethylamino]-pyrimidin-4-yl}-3-nitro-2-phenyl-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one (61 mg, 0.11 mmol) in 1 mL methanol was safely added 10 mg palladium on carbon (10%) and stirred over an atmosphere of hydrogen delivered by a balloon. After 2 h, the ... | 10.6084/m9.figshare.5104873.v1 | null | Azide.Nitro group | Primary amine.Primary amine | null | null | c1ccccc1.c1cncnc1.c1cnc2n(c1)CCCN2.c1ccccc1 | Other | [Pd].CO | null | 2 | CC(Cc1cccc(CN=[N+]=[N-])c1)Nc1nccc(N2CCCn3c2nc(-c2ccccc2)c([N+](=O)[O-])c3=O)n1>[Pd].CO>CC(Cc1cccc(CN)c1)Nc1nccc(N2CCCn3c2nc(-c2ccccc2)c(N)c3=O)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0384e25b9b4a441480961a9cfcdfd9a4 | CC[N+](=O)[O-].O=Cc1cccc(Br)c1>>CC(=Cc1cccc(Br)c1)[N+](=O)[O-] | BrC=1C=C(C=O)C=CC1.C(C)(=O)[O-].[NH4+].[N+](=O)([O-])CC>>BrC1=CC(=CC=C1)C=C(C)[N+](=O)[O-] | [CH3:1][CH2:2][N+:11](=[O:12])[O-:13].O=[CH:3][c:4]1[cH:5][cH:6][cH:7][c:8]([Br:9])[cH:10]1>>[CH3:1][C:2](=[CH:3][c:4]1[cH:5][cH:6][cH:7][c:8]([Br:9])[cH:10]1)[N+:11](=[O:12])[O-:13] | CC[N+](=O)[O-].O=Cc1cccc(Br)c1 | CC(=Cc1cccc(Br)c1)[N+](=O)[O-] | null | null | null | C-C Coupling | OtherReaction | 7ede86d40d3d69f429dde089476c8b7ffa9b74bf3050590255e6323d013c2daf | f736727903c0ad5511d468246b8e380897fd19905174c118ffa4ed4d3651f6ea | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[CH2;D2;+0:6]-[#7;+:7](-[O;-;D1;H0:8])=[O;D1;H0:9]>>[C;D1;H3:5]-[C;H0;D3;+0:6](=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[#7;+:7](-[O;-;D1;H0:8])=[O;D1;H0:9] | null | [] | null | null | null | null | A suspension of 3-bromo-benzaldehyde (2.5 g, 13.5 mmol), ammonium acetate (1.09 g, 14.2 mmol), and nitroethane (250 mL) was heated to reflux overnight. Solvent removed under vacuum then residue partitioned between ethyl acetate and saturated sodium chloride. Concentrated organic purified on silica and isolated as a yel... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitro group | Enamine | null | null | c1ccccc1 | HO- | null | null | null | CC[N+](=O)[O-].O=Cc1cccc(Br)c1>>CC(=Cc1cccc(Br)c1)[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-95b831007d3a45b8a724f5ec6009c0d9 | CC(Cc1cccc(Br)c1)NC(=O)OC(C)(C)C.[C-]#N>>CC(Cc1cccc(C#N)c1)NC(=O)OC(C)(C)C | C(C)(C)(C)OC(NC(CC1=CC(=CC=C1)Br)C)=O.[C-]#N.[Na+].[I-].[K+]>>C(C)(C)(C)OC(NC(CC1=CC(=CC=C1)C#N)C)=O | Br[c:8]1[cH:7][cH:6][cH:5][c:4]([CH2:3][CH:2]([CH3:1])[NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[cH:11]1.[C-:9]#[N:10]>>[CH3:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([C:9]#[N:10])[cH:11]1)[NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19] | CC(Cc1cccc(Br)c1)NC(=O)OC(C)(C)C.[C-]#N | CC(Cc1cccc(C#N)c1)NC(=O)OC(C)(C)C | null | [Cu](I)I | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 74297fda360e2eb1332083b2a3b4d6d0d871d1388106d750919b9547cad5399b | 2549b026e730aedabd9d1c88337e10b7987bb7b86597cabf3fd7fef1a79c8a9a | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C-;H0;D1:6]#[N;D1;H0:7]>>[N;D1;H0:7]#[C;H0;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | 130 | CELSIUS | null | null | To a sealed pressure tube was added [2-(3-bromo-phenyl)-1-methyl-ethyl]-carbamic acid tert-butyl ester (1.23 g, 3.9 mmol), sodium cyanide (250 mg, 5.1 mmol), potassium iodide (130 mg, 0.8 mmol), N-N′-dimethylethylenediamine (0.41 mL, 3.9 mmol), and toluene (6 mL). This suspension was then sparged with nitrogen prior to... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccccc1 | c1ccccc1 | c1ccccc1 | Br- | [Cu](I)I.C1(=CC=CC=C1)C | 130 | null | CC(Cc1cccc(Br)c1)NC(=O)OC(C)(C)C.[C-]#N>[Cu](I)I.C1(=CC=CC=C1)C>CC(Cc1cccc(C#N)c1)NC(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8eed1f6741c94565b214f88940a313f8 | CC(Cc1cccc(C#N)c1)NC(=O)OC(C)(C)C>>CC(N)Cc1cccc(C#N)c1 | C(C)(C)(C)OC(NC(CC1=CC(=CC=C1)C#N)C)=O>>NC(CC=1C=C(C#N)C=CC1)C | CC(C)(C)OC(=O)[NH:3][CH:2]([CH3:1])[CH2:4][c:5]1[cH:6][cH:7][cH:8][c:9]([C:10]#[N:11])[cH:12]1>>[CH3:1][CH:2]([NH2:3])[CH2:4][c:5]1[cH:6][cH:7][cH:8][c:9]([C:10]#[N:11])[cH:12]1 | CC(Cc1cccc(C#N)c1)NC(=O)OC(C)(C)C | CC(N)Cc1cccc(C#N)c1 | null | null | ClCCl.FC(C(=O)O)(F)F | 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;D1;H3:4]>>[C:3]-[C:2](-[C;D1;H3:4])-[NH2;D1;+0:1] | null | [] | null | null | null | null | A solution of [2-(3-Cyano-phenyl) -1-methyl-ethyl]-carbamic acid tert-butyl ester (180 mg, 0.69 mmol) in dichloromethane (5 mL) and trifluoroacetic acid (5 mL) was stirred for 15 min at room temperature. Solvents removed under vacuum, and residue was partitioned between dichloromethane and 1 N sodium hydroxide. Organic... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1 | HO- | ClCCl.FC(C(=O)O)(F)F | null | null | CC(Cc1cccc(C#N)c1)NC(=O)OC(C)(C)C>ClCCl.FC(C(=O)O)(F)F>CC(N)Cc1cccc(C#N)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-56f42368a1034a21b636a99b3922ec7e | CC(Cc1cccc(Br)c1)NC(=O)OC(C)(C)C.N=C(c1ccccc1)c1ccccc1>>CC(Cc1cccc(N=C(c2ccccc2)c2ccccc2)c1)NC(=O)OC(C)(C)C | C(C)(C)(C)OC(NC(CC1=CC(=CC=C1)Br)C)=O.C(C1=CC=CC=C1)(C1=CC=CC=C1)=N.CC(C)([O-])C.[Na+].C1(=CC=CC=C1)P(C1=CC=CC=C1)C=1C(=C(C2=CC=CC=C2C1)C1=CC=CC2=CC=CC=C12)P(C1=CC=CC=C1)C1=CC=CC=C1>>C(C)(C)(C)OC(NC(CC1=CC(=CC=C1)N=C(C1=CC=CC=C1)C1=CC=CC=C1)C)=O | Br[c:8]1[cH:7][cH:6][cH:5][c:4]([CH2:3][CH:2]([CH3:1])[NH:24][C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[cH:23]1.[NH:9]=[C:10]([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[CH3:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([N:9]=[C:10]([c:11]2[cH:12][cH:13][cH:14... | CC(Cc1cccc(Br)c1)NC(=O)OC(C)(C)C.N=C(c1ccccc1)c1ccccc1 | CC(Cc1cccc(N=C(c2ccccc2)c2ccccc2)c1)NC(=O)OC(C)(C)C | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | CCOCC.C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 3ab6ef823e0d4534383112adb38b155a891f50d2723d4a49693209524e5adc0c | d6fdf3485f414343350878d3990b407f7838ca1f9344576c0f428d9ed6db7945 | c1ccc(N=C(c2ccccc2)c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[NH;D1;+0:6]=[C:7](-[c:8])-[c:9]>>[c:8]-[C:7](-[c:9])=[N;H0;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | A suspension of [2-(3-bromo-phenyl)-1-methyl-ethyl]-carbamic acid tert-butyl ester (750 mg, 2.39 mmol), benzophenone imine (0.44 mL, 2.63 mmol), sodium tert-butoxide (298 mg, 3.1 mmol), bis(diphenylphosphino)-1,1′-binaphthyl (45 mg, 0.07 mmol), palladium acetate (16 mg, 0.07 mmol), and toluene (7.5 mL) was heated to re... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Unsubstituted imine | Substituted imine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | HBr | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].CCOCC.C1(=CC=CC=C1)C | null | null | CC(Cc1cccc(Br)c1)NC(=O)OC(C)(C)C.N=C(c1ccccc1)c1ccccc1>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].CCOCC.C1(=CC=CC=C1)C>CC(Cc1cccc(N=C(c2ccccc2)c2ccccc2)c1)NC(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8ecacdfd807041be80650c8a448f0c32 | CC(Cc1cccc(N=C(c2ccccc2)c2ccccc2)c1)NC(=O)OC(C)(C)C>>CC(N)Cc1cccc(N)c1 | C(C)(C)(C)OC(NC(CC1=CC(=CC=C1)N=C(C1=CC=CC=C1)C1=CC=CC=C1)C)=O>>NC(CC=1C=C(C=CC1)N)C | CC(C)(C)OC(=O)[NH:3][CH:2]([CH3:1])[CH2:4][c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=C(c2ccccc2)c2ccccc2)[cH:11]1>>[CH3:1][CH:2]([NH2:3])[CH2:4][c:5]1[cH:6][cH:7][cH:8][c:9]([NH2:10])[cH:11]1 | CC(Cc1cccc(N=C(c2ccccc2)c2ccccc2)c1)NC(=O)OC(C)(C)C | CC(N)Cc1cccc(N)c1 | null | null | ClCCl.FC(C(=O)O)(F)F | Reduction | OtherReaction | 70e222f2a6f328725792062e6aba571f022e49dadd30fbdfffb717a46808fe65 | 8fb60491da507af5d2870916806588caf3324428a072eccbaefe9cc525853e98 | c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C;D1;H3:4].[c:5]:[c:6](-[N;H0;D2;+0:7]=C(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1):[c:8]>>[C:3]-[C:2](-[C;D1;H3:4])-[NH2;D1;+0:1].[NH2;D1;+0:7]-[c:6](:[c:5]):[c:8] | null | [] | null | null | 20 | MINUTE | A solution {2-[3(Benzhydrylidene-amino)-phenyl]-1-methyl-ethyl}-carbamic acid tert-butyl ester (200 mg, 0.48 mmol) in dichloromethane (5 mL) and trifluoroacetic acid (5 mL) was stirred for 45 min at room temperature. Solvents removed under vacuum and residue suspended in 5 N hydrochloric acid at 60° C. for 20 min. Biph... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Substituted imine.Boc | Primary amine.Primary amine | c1ccccc1.c1ccccc1 | null | c1ccccc1 | HO- | ClCCl.FC(C(=O)O)(F)F | null | 0.333333 | CC(Cc1cccc(N=C(c2ccccc2)c2ccccc2)c1)NC(=O)OC(C)(C)C>ClCCl.FC(C(=O)O)(F)F>CC(N)Cc1cccc(N)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a820332cb9344d6e98a8146195b03288 | CC[N+](=O)[O-].COC(=O)c1cccc(C=O)c1>>COC(=O)c1cccc(C=C(C)[N+](=O)[O-])c1 | COC(C1=CC(=CC=C1)C=O)=O.C(C)(=O)[O-].[NH4+].[N+](=O)([O-])CC>>COC(C1=CC(=CC=C1)C=C(C)[N+](=O)[O-])=O | [CH2:11]([CH3:12])[N+:13](=[O:14])[O-:15].O=[CH:10][c:9]1[cH:8][cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:16]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([CH:10]=[C:11]([CH3:12])[N+:13](=[O:14])[O-:15])[cH:16]1 | CC[N+](=O)[O-].COC(=O)c1cccc(C=O)c1 | COC(=O)c1cccc(C=C(C)[N+](=O)[O-])c1 | null | null | null | C-C Coupling | OtherReaction | 7ede86d40d3d69f429dde089476c8b7ffa9b74bf3050590255e6323d013c2daf | f736727903c0ad5511d468246b8e380897fd19905174c118ffa4ed4d3651f6ea | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[CH2;D2;+0:6]-[#7;+:7](-[O;-;D1;H0:8])=[O;D1;H0:9]>>[C;D1;H3:5]-[C;H0;D3;+0:6](=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[#7;+:7](-[O;-;D1;H0:8])=[O;D1;H0:9] | null | [] | null | null | 1.5 | HOUR | To a 250 mL round bottom flask was added 3-formyl-benzoic acid methyl ester (2.20 g, 13.4 mmol), ammonium acetate (1.03 g, 13.4 mmol), and nitroethane (60 mL). Mixture heated to reflux under an atmosphere of nitrogen while stirring for 1.5 h. Solvent removed under vacuum then residue partitioned between ethyl acetate (... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitro group | Enamine | null | null | c1ccccc1 | HO- | null | null | 1.5 | CC[N+](=O)[O-].COC(=O)c1cccc(C=O)c1>>COC(=O)c1cccc(C=C(C)[N+](=O)[O-])c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9d93330cbfb24dd48d5ecbd2a97476b6 | CC(N)Cc1cccc(CO)c1.CS(=O)(=O)c1nccc(N2CCCn3c2nc(-c2ccccc2)cc3=O)n1>>CC(Cc1cccc(CO)c1)Nc1nccc(N2CCCn3c2nc(-c2ccccc2)cc3=O)n1 | CS(=O)(=O)C1=NC=CC(=N1)N1CCCN2C1=NC(=CC2=O)C2=CC=CC=C2.NC(CC=1C=C(C=CC1)CO)C.CN1CCOCC1>>OCC=1C=C(C=CC1)CC(C)NC1=NC=CC(=N1)N1CCCN2C1=NC(=CC2=O)C2=CC=CC=C2 | [CH3:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([CH2:9][OH:10])[cH:11]1)[NH2:12].CS(=O)(=O)[c:13]1[n:14][cH:15][cH:16][c:17]([N:18]2[CH2:19][CH2:20][CH2:21][n:22]3[c:23]2[n:24][c:25](-[c:26]2[cH:27][cH:28][cH:29][cH:30][cH:31]2)[cH:32][c:33]3=[O:34])[n:35]1>>[CH3:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([CH2:9]... | CC(N)Cc1cccc(CO)c1.CS(=O)(=O)c1nccc(N2CCCn3c2nc(-c2ccccc2)cc3=O)n1 | CC(Cc1cccc(CO)c1)Nc1nccc(N2CCCn3c2nc(-c2ccccc2)cc3=O)n1 | null | null | ClCCl.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 289adcacbe89f1503fb3c9d1b660927aaeb421d7b5520077738f22dce3010144 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1cc(-c2ccccc2)nc2n1CCCN2c1ccnc(NCCc2ccccc2)n1 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7](-[C;D1;H3:8])-[NH2;D1;+0:9]>>[C:6]-[C:7](-[C;D1;H3:8])-[NH;D2;+0:9]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | null | [] | 100 | CELSIUS | null | null | A mixture of 9-(2-methanesulfonyl-pyrimidin -4-yl)-2-phenyl-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one (344 mg, 0.90 mmol), [3-(2-amino-propyl)-phenyl]-methanol (371 mg, 2.25 mmol), and N-methylmorpholine (8 mL) was heated to 100° C. for 20 h. Reaction was diluted with dichloromethane (15 mL) and ethyl acetate (... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccn2c(n1)NCCC2.c1ccccc1 | HO- | ClCCl.C(C)(=O)OCC | 100 | null | CC(N)Cc1cccc(CO)c1.CS(=O)(=O)c1nccc(N2CCCn3c2nc(-c2ccccc2)cc3=O)n1>ClCCl.C(C)(=O)OCC>CC(Cc1cccc(CO)c1)Nc1nccc(N2CCCn3c2nc(-c2ccccc2)cc3=O)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-86c75631c5b6483ba0e751a1d0c18781 | CC(Cc1cccc(CO)c1)Nc1nccc(N2CCCn3c2nc(-c2ccccc2)cc3=O)n1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>>CC(Cc1cccc(CN=[N+]=[N-])c1)Nc1nccc(N2CCCn3c2nc(-c2ccccc2)cc3=O)n1 | OCC=1C=C(C=CC1)CC(C)NC1=NC=CC(=N1)N1CCCN2C1=NC(=CC2=O)C2=CC=CC=C2.N12CCCCCC2=NCCC1.C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)N=[N+]=[N-]>>N(=[N+]=[N-])CC=1C=C(C=CC1)CC(C)NC1=NC=CC(=N1)N1CCCN2C1=NC(=CC2=O)C2=CC=CC=C2 | O[CH2:9][c:8]1[cH:7][cH:6][cH:5][c:4]([CH2:3][CH:2]([CH3:1])[NH:14][c:15]2[n:16][cH:17][cH:18][c:19]([N:20]3[CH2:21][CH2:22][CH2:23][n:24]4[c:25]3[n:26][c:27](-[c:28]3[cH:29][cH:30][cH:31][cH:32][cH:33]3)[cH:34][c:35]4=[O:36])[n:37]2)[cH:13]1.O=P(c1ccccc1)(c1ccccc1)[N:10]=[N+:11]=[N-:12]>>[CH3:1][CH:2]([CH2:3][c:4]1[cH... | CC(Cc1cccc(CO)c1)Nc1nccc(N2CCCn3c2nc(-c2ccccc2)cc3=O)n1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1 | CC(Cc1cccc(CN=[N+]=[N-])c1)Nc1nccc(N2CCCn3c2nc(-c2ccccc2)cc3=O)n1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | cfa52427fe008248ccb3b060cca934c64c46f29eb11684ddb953f16825bf2f0e | da5ad8c0affa2dc7232b479927687ff59fae3f37df63d467193897a964229798 | O=c1cc(-c2ccccc2)nc2n1CCCN2c1ccnc(NCCc2ccccc2)n1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].O=P(-[N;H0;D2;+0:5]=[#7;+:6]=[N;-;D1;H0:7])(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[N;-;D1;H0:7]=[#7;+:6]=[N;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 8 | HOUR | To a stirring mixture of 9-{2-[2-(3-hydroxymethyl-phenyl) -1-methyl-ethylamino]-pyrimidin-4-yl}-2-phenyl-6,7,8,9-tetrahydro -pyrimido[1,2-a]pyrimidin-4-one (230 mg, 0.49 mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (0.13 mL, 0.88 mmol), and tetrahydrofuran (12 mL) at 0° C. under an atmosphere of nitrogen was added dipheny... | 10.6084/m9.figshare.5104873.v1 | null | Azide.Primary alcohol | Azide | c1ccccc1.c1ccccc1 | null | c1ccccc1.c1cncnc1.c1ccn2c(n1)NCCC2.c1ccccc1 | HO- | O1CCCC1 | null | 8 | CC(Cc1cccc(CO)c1)Nc1nccc(N2CCCn3c2nc(-c2ccccc2)cc3=O)n1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>O1CCCC1>CC(Cc1cccc(CN=[N+]=[N-])c1)Nc1nccc(N2CCCn3c2nc(-c2ccccc2)cc3=O)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-517e1cd8503744eb90d364e2066a75a1 | CC(Cc1cccc(CN=[N+]=[N-])c1)Nc1nccc(N2CCCn3c2nc(-c2ccccc2)cc3=O)n1>>CC(Cc1cccc(CN)c1)Nc1nccc(N2CCCn3c2nc(-c2ccccc2)cc3=O)n1 | N(=[N+]=[N-])CC=1C=C(C=CC1)CC(C)NC1=NC=CC(=N1)N1CCCN2C1=NC(=CC2=O)C2=CC=CC=C2.[H][H]>>NCC=1C=C(C=CC1)CC(C)NC1=NC=CC(=N1)N1CCCN2C1=NC(=CC2=O)C2=CC=CC=C2 | [N-]=[N+]=[N:10][CH2:9][c:8]1[cH:7][cH:6][cH:5][c:4]([CH2:3][CH:2]([CH3:1])[NH:12][c:13]2[n:14][cH:15][cH:16][c:17]([N:18]3[CH2:19][CH2:20][CH2:21][n:22]4[c:23]3[n:24][c:25](-[c:26]3[cH:27][cH:28][cH:29][cH:30][cH:31]3)[cH:32][c:33]4=[O:34])[n:35]2)[cH:11]1>>[CH3:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([CH2:9][NH... | CC(Cc1cccc(CN=[N+]=[N-])c1)Nc1nccc(N2CCCn3c2nc(-c2ccccc2)cc3=O)n1 | CC(Cc1cccc(CN)c1)Nc1nccc(N2CCCn3c2nc(-c2ccccc2)cc3=O)n1 | null | [Pd] | CO | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | O=c1cc(-c2ccccc2)nc2n1CCCN2c1ccnc(NCCc2ccccc2)n1 | [N-]=[N+]=[N;H0;D2;+0:1]-[C:2]-[c:3]>>[NH2;D1;+0:1]-[C:2]-[c:3] | null | [] | null | null | 2 | HOUR | To a nitrogen filled vessel containing a stirring solution of 9-{2-[2-(3-azidomethyl-phenyl)-1-methyl -ethylamino]-pyrimidin-4-yl}-2-phenyl-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one (190 mg, 0.39 mmol) in methanol (25 mL) was added 10% palladium on carbon (20 mg). Mixture stirred over an atmosphere of hydrogen.... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | c1ccccc1.c1cncnc1.c1ccn2c(n1)NCCC2.c1ccccc1 | Other | [Pd].CO | null | 2 | CC(Cc1cccc(CN=[N+]=[N-])c1)Nc1nccc(N2CCCn3c2nc(-c2ccccc2)cc3=O)n1>[Pd].CO>CC(Cc1cccc(CN)c1)Nc1nccc(N2CCCn3c2nc(-c2ccccc2)cc3=O)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fc3dbec9aa8e4950a90e014c05e7034c | CC(C)=O.CC(Cc1cccc(CN)c1)Nc1nccc(N2CCCn3c2nc(-c2ccccc2)cc3=O)n1>>CC(C)NCc1cccc(CC(C)Nc2nccc(N3CCCn4c3nc(-c3ccccc3)cc4=O)n2)c1 | NCC=1C=C(C=CC1)CC(C)NC1=NC=CC(=N1)N1CCCN2C1=NC(=CC2=O)C2=CC=CC=C2.CC(=O)C.[BH4-].[Na+]>>C(C)(C)NCC=1C=C(C=CC1)CC(C)NC1=NC=CC(=N1)N1CCCN2C1=NC(=CC2=O)C2=CC=CC=C2 | O=[C:2]([CH3:1])[CH3:3].[NH2:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][c:10]([CH2:11][CH:12]([CH3:13])[NH:14][c:15]2[n:16][cH:17][cH:18][c:19]([N:20]3[CH2:21][CH2:22][CH2:23][n:24]4[c:25]3[n:26][c:27](-[c:28]3[cH:29][cH:30][cH:31][cH:32][cH:33]3)[cH:34][c:35]4=[O:36])[n:37]2)[cH:38]1>>[CH3:1][CH:2]([CH3:3])[NH:4][CH2:5][c:6]1[... | CC(C)=O.CC(Cc1cccc(CN)c1)Nc1nccc(N2CCCn3c2nc(-c2ccccc2)cc3=O)n1 | CC(C)NCc1cccc(CC(C)Nc2nccc(N3CCCn4c3nc(-c3ccccc3)cc4=O)n2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with ketone | 4940e8ed9a0db9bde699fdcdc3aff2cff0409c19478aa0ed1acfd98213338adf | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | O=c1cc(-c2ccccc2)nc2n1CCCN2c1ccnc(NCCc2ccccc2)n1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[C;D1;H3:2]-[CH;D3;+0:1](-[C;D1;H3:3])-[NH;D2;+0:4]-[C:5]-[c:6] | null | [] | null | null | 10 | MINUTE | A solution of 9-{2-[2-(3-Aminomethyl-phenyl) -1-methyl-ethylamino]-pyrimidin-4-yl}-2-phenyl-6,7,8,9-tetrahydro -pyrimido[1,2-a]pyrimidin-4-one (79 mg, 0.17 mmol) and acetone (0.015 mL, 0.21 mmol) was stirred for 10 min prior to adding sodium borohydride (108 mg, 3.4 mmol). After 10 min, solvent removed under vacuum and... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | null | null | c1ccccc1.c1cncnc1.c1ccn2c(n1)NCCC2.c1ccccc1 | Other | null | null | 0.166667 | CC(C)=O.CC(Cc1cccc(CN)c1)Nc1nccc(N2CCCn3c2nc(-c2ccccc2)cc3=O)n1>>CC(C)NCc1cccc(CC(C)Nc2nccc(N3CCCn4c3nc(-c3ccccc3)cc4=O)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d86b6b18a28c4f038adcd080d0ff95b5 | CC(C)(C)[Si](C)(C)Cl.OCc1cccc(Br)c1>>CC(C)(C)[Si](C)(C)OCc1cccc(Br)c1 | BrC=1C=C(CO)C=CC1.[Si](C)(C)(C(C)(C)C)Cl.O>>BrC=1C=C(CO[Si](C)(C)C(C)(C)C)C=CC1 | Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]([Br:15])[cH:16]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]([Br:15])[cH:16]1 | CC(C)(C)[Si](C)(C)Cl.OCc1cccc(Br)c1 | CC(C)(C)[Si](C)(C)OCc1cccc(Br)c1 | null | null | CN(C=O)C | Protection | Alcohol protection with silyl ethers | 0085cd6629412592263fdf1537bdf8c19ef10dbeafe6f880807464d8107fa715 | d2a170d01b2f3ec57d6fac058519475050ba5531f5d304635fb42e153d5bb9b5 | c1ccccc1 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[OH;D1;+0:8]-[C:9]-[c:10]>>[C;D1;H3:5]-[C:4](-[C;D1;H3:6])(-[C;D1;H3:7])-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[O;H0;D2;+0:8]-[C:9]-[c:10] | null | [] | null | null | null | null | A solution 3-bromobenzyl alcohol (7.1 g, 38 mmol) and tert-butyldimethylsilyl chloride (5.7 g, 38 mmol) in N,N-dimethylformamide (40 mL) was stirred at room temperature for 5 h. Water (40 mL) was added and the mixture was extracted with hexanes. The combined extracts were washed with 10% aqueous hydrochloric acid, satu... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Silyl protective group | TMS ether protective group | null | null | c1ccccc1 | HCl | CN(C=O)C | null | null | CC(C)(C)[Si](C)(C)Cl.OCc1cccc(Br)c1>CN(C=O)C>CC(C)(C)[Si](C)(C)OCc1cccc(Br)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-64cb8344a4f74ecfb861d0bd45cd28af | CC(C)(C)[Si](C)(C)OCc1cccc(Br)c1.C[C@@H]1CO1>>CC(O)Cc1cccc(CO[Si](C)(C)C(C)(C)C)c1 | C1[C@@H](C)O1.[Cl-].[NH4+].[OH-].[NH4+].BrC=1C=C(CO[Si](C)(C)C(C)(C)C)C=CC1.[Mg].II>>[Si](C)(C)(C(C)(C)C)OCC=1C=C(C=CC1)CC(C)O | Br[c:5]1[cH:6][cH:7][cH:8][c:9]([CH2:10][O:11][Si:12]([CH3:13])([CH3:14])[C:15]([CH3:16])([CH3:17])[CH3:18])[cH:19]1.[CH3:1][C@H:2]1[O:3][CH2:4]1>>[CH3:1][CH:2]([OH:3])[CH2:4][c:5]1[cH:6][cH:7][cH:8][c:9]([CH2:10][O:11][Si:12]([CH3:13])([CH3:14])[C:15]([CH3:16])([CH3:17])[CH3:18])[cH:19]1 | CC(C)(C)[Si](C)(C)OCc1cccc(Br)c1.C[C@@H]1CO1 | CC(O)Cc1cccc(CO[Si](C)(C)C(C)(C)C)c1 | null | [Cu]I.[Cu] | O1CCCC1 | C-C Coupling | OtherReaction | fe9b1026862bafa5af476ea37b65f4571fe973f56d02ac2e70c4fc844fb9c746 | 79fd712a2a6d6b4abbd49e003e84f4018bdf16c930e348b877ef642996ef6e0f | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[C@@H;D3;+0:7]1-[CH2;D2;+0:8]-[O;H0;D2;+0:9]-1>>[C;D1;H3:6]-[CH;D3;+0:7](-[OH;D1;+0:9])-[CH2;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | 0 | CELSIUS | 5 | MINUTE | To a stirring solution of (3-bromobenzyloxy)-tert-butyldimethylsilane (7.0 g, 24 mmol) in tetrahydrofuran (100 mL) under an atmosphere of nitrogen was added magnesium turnings (0.73 g, 30 mmol) and a crystal of iodine. The mixture was heated to reflux for 1 h, cooled to 0° C. and copper (I) iodide (4.57 g, 24 mmol) was... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether | Secondary alcohol | c1ccccc1.C1CO1 | c1ccccc1 | c1ccccc1 | Br- | [Cu]I.[Cu].O1CCCC1 | 0 | 0.083333 | CC(C)(C)[Si](C)(C)OCc1cccc(Br)c1.C[C@@H]1CO1>[Cu]I.[Cu].O1CCCC1>CC(O)Cc1cccc(CO[Si](C)(C)C(C)(C)C)c1 |
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