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-c3a75813d0b24864aa4f7cd526efd6aa | ord-d90d6fe554fe4673b93da7fd41450434 | CC(=O)CCl.COc1cccc(CC(=O)O)c1>>COc1cccc(C2=C(C)COC2=O)c1 | COC=1C=C(C=CC1)CC(=O)O.ClCC(C)=O.C([O-])([O-])=O.[K+].[K+]>>COC=1C=C(C=CC1)C=1C(OCC1C)=O | O=[C:9]([CH3:10])[CH2:11]Cl.[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][C:13]([OH:12])=[O:14])[cH:15]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8]2=[C:9]([CH3:10])[CH2:11][O:12][C:13]2=[O:14])[cH:15]1 | CC(=O)CCl.COc1cccc(CC(=O)O)c1 | COc1cccc(C2=C(C)COC2=O)c1 | null | null | C(C)#N.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | f037be6f9f026cd579480779429d9cffa8fcccf26ea746a7829725f430e584b0 | 937de3c41eef8eee72ef9ea5c72ba31c48840f648e4818110e3ac17f0dc2e4ad | O=C1OCC=C1c1ccccc1 | Cl-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[C;D1;H3:3].[O;D1;H0:4]=[C:5](-[OH;D1;+0:6])-[CH2;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[C;D1;H3:3]-[C;H0;D3;+0:2]1=[C;H0;D3;+0:7](-[c:8](:[c:9]):[c:10])-[C:5](=[O;D1;H0:4])-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-1 | 78.3 | [{"value": 78.0, "product": "COC=1C=C(C=CC1)C=1C(OCC1C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.3, "product": "COC=1C=C(C=CC1)C=1C(OCC1C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-methoxyphenylacetic acid (3.32 g, 20 mmol), chloroacetone (2.02 g, 22 mmol) and potassium carbonate (6.07 g, 44 mmol) in acetonitrile (30 mL) was heated at reflux for 5 hours. The resultant mixture was cooled to room temperature, diluted with ethyl acetate (60 ml), filtered through a silica gel pad, and ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid.Ketone | Ester | null | C1=CCOC1 | c1ccccc1.C1=CCOC1 | HCl | C(C)#N.C(C)(=O)OCC | null | null | CC(=O)CCl.COc1cccc(CC(=O)O)c1>C(C)#N.C(C)(=O)OCC>COc1cccc(C2=C(C)COC2=O)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6d7f6c1d0fb4448c91e459ba3e7b5f52 | COc1cccc(C2=C(C)C(O)=C(c3ccccc3F)C2=O)c1.NN>>COc1cccc(-c2c(C)c(Cc3ccccc3F)n[nH]c2=O)c1 | FC1=C(C=CC=C1)C=1C(C(=C(C1O)C)C1=CC(=CC=C1)OC)=O.NN>>COC=1C=C(C=CC1)C=1C(NN=C(C1C)CC1=C(C=CC=C1)F)=O | O[C:11]1=[C:12]([c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[F:19])[C:22](=[O:23])[C:8]([c:7]2[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:24]2)=[C:9]1[CH3:10].[NH2:20][NH2:21]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[c:9]([CH3:10])[c:11]([CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[F:19])[n:20][nH:21][c:22]2... | COc1cccc(C2=C(C)C(O)=C(c3ccccc3F)C2=O)c1.NN | COc1cccc(-c2c(C)c(Cc3ccccc3F)n[nH]c2=O)c1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 9f678f2f06f900afb4258288a0c2b8371f6bff592372f71bfa949c9840e6dc50 | c2790070e27efbbc474e6080da1ee4222c56864eff47ebd8dfe5dfe90cdba91c | O=c1[nH]nc(Cc2ccccc2)cc1-c1ccccc1 | O-[C;H0;D3;+0:1]1=[C;H0;D3;+0:2](-[c:3](:[c:4]):[c:5])-[C;H0;D3;+0:6](=[O;D1;H0:7])-[C;H0;D3;+0:8](-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13])=[C;H0;D3;+0:14]-1-[C;D1;H3:15].[NH2;D1;+0:16]-[NH2;D1;+0:17]>>[C;D1;H3:15]-[c;H0;D3;+0:14]1:[c;H0;D3;+0:1](-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]):[n;H0;D2;+0:16]:[nH;D2;+0:17]:[... | null | [] | null | null | null | null | A solution of 2-(2-fluorophenyl)-3-hydroxy-4-methyl-5-(3-methoxyphenyl)-2,4-cyclopentadienone (310 mg, 1 mmol) and hydrazine (0.2 mL) in ethanol (5 mL) was heated at reflux for 30 minutes. The resulting solution was concentrated in vacuo and the residue was dissolved in dichloromethane, dried over sodium sulfate, filte... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Enol | null | C1=CCC=C1 | c1ccnnc1 | c1ccccc1.c1ccnnc1.c1ccccc1 | HO- | C(C)O | null | null | COc1cccc(C2=C(C)C(O)=C(c3ccccc3F)C2=O)c1.NN>C(C)O>COc1cccc(-c2c(C)c(Cc3ccccc3F)n[nH]c2=O)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-13e9cb82d93847d4911378adc2ceb4c0 | COc1cccc(C2=C(C)C(O)=C(c3ccccc3F)C2=O)c1.NNCCO>>COc1cccc(-c2c(C)c(Cc3ccccc3F)nn(CCO)c2=O)c1 | FC1=C(C=CC=C1)C=1C(C(=C(C1O)C)C1=CC(=CC=C1)OC)=O.OCCNN>>COC=1C=C(C=CC1)C=1C(N(N=C(C1C)CC1=C(C=CC=C1)F)CCO)=O | O[C:11]1=[C:12]([c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[F:19])[C:25](=[O:26])[C:8]([c:7]2[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:27]2)=[C:9]1[CH3:10].[NH2:20][NH:21][CH2:22][CH2:23][OH:24]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[c:9]([CH3:10])[c:11]([CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[F:19... | COc1cccc(C2=C(C)C(O)=C(c3ccccc3F)C2=O)c1.NNCCO | COc1cccc(-c2c(C)c(Cc3ccccc3F)nn(CCO)c2=O)c1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 9f678f2f06f900afb4258288a0c2b8371f6bff592372f71bfa949c9840e6dc50 | c2790070e27efbbc474e6080da1ee4222c56864eff47ebd8dfe5dfe90cdba91c | O=c1[nH]nc(Cc2ccccc2)cc1-c1ccccc1 | O-[C;H0;D3;+0:1]1=[C;H0;D3;+0:2](-[c:3](:[c:4]):[c:5])-[C;H0;D3;+0:6](=[O;D1;H0:7])-[C;H0;D3;+0:8](-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13])=[C;H0;D3;+0:14]-1-[C;D1;H3:15].[C:16]-[C:17]-[NH;D2;+0:18]-[NH2;D1;+0:19]>>[C:16]-[C:17]-[n;H0;D3;+0:18]1:[n;H0;D2;+0:19]:[c;H0;D3;+0:1](-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]):[... | null | [] | null | null | null | null | A solution of 2-(2-fluorophenyl)-3-hydroxy-4-methyl-5-(3-methoxyphenyl)-2,4-cyclopentadienone (620 mg, 2 mmol) and hydroxylethylhydrazine (360 mg, 45 mmol)) in ethanol (5 mL) was heated at reflux for 6 hours. The resulting solution was concentrated in vacuo and the residue was dissolved in ethyl acetate (80 mL), washed... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Enol | null | C1=CCC=C1 | c1ccnnc1 | c1ccccc1.c1ccnnc1.c1ccccc1 | HO- | C(C)O | null | null | COc1cccc(C2=C(C)C(O)=C(c3ccccc3F)C2=O)c1.NNCCO>C(C)O>COc1cccc(-c2c(C)c(Cc3ccccc3F)nn(CCO)c2=O)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-111159e019154de4a7d6678f976321db | COc1cccc(-c2c(C)c(Cc3ccccc3F)nn(CCO)c2=O)c1.NC(=O)CCC(=O)NBr>>COc1cccc(-c2c(C)c(Cc3ccccc3F)nn(CCBr)c2=O)c1 | COC=1C=C(C=CC1)C=1C(N(N=C(C1C)CC1=C(C=CC=C1)F)CCO)=O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.BrNC(CCC(=O)N)=O>>COC=1C=C(C=CC1)C=1C(N(N=C(C1C)CC1=C(C=CC=C1)F)CCBr)=O | O[CH2:23][CH2:22][n:21]1[n:20][c:11]([CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[F:19])[c:9]([CH3:10])[c:8](-[c:7]2[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:27]2)[c:25]1=[O:26].NC(=O)CCC(=O)N[Br:24]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[c:9]([CH3:10])[c:11]([CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17]... | COc1cccc(-c2c(C)c(Cc3ccccc3F)nn(CCO)c2=O)c1.NC(=O)CCC(=O)NBr | COc1cccc(-c2c(C)c(Cc3ccccc3F)nn(CCBr)c2=O)c1 | null | null | ClCCl | Functional Group Interconversion | OtherReaction | 36d5a3000ac6c18c3e3d0fda946e9d162639e9954840bbf4cf8fd21a99f6135c | a49bb2725045f0903d387e3d995d862f3db137c208b16c8cc18a21cfd61f70da | O=c1[nH]nc(Cc2ccccc2)cc1-c1ccccc1 | N-C(=O)-C-C-C(=O)-N-[Br;H0;D1;+0:1].O-[CH2;D2;+0:2]-[C:3]-[#7;a:4]>>[#7;a:4]-[C:3]-[CH2;D2;+0:2]-[Br;H0;D1;+0:1] | null | [] | null | null | null | null | A solution of 4-(3-methoxyphenyl)-5-methyl-6-(2-fluorobenzyl)-2-(2-hydroxyethyl)-pyridazin-3-one (from above) and triphenylphospine (570 mg, 22 mmol) in dichloromethane (8 mL) was treated with N-bromosuccinamide (400 mg, 22 mmol) at room temperature for 2 hours. The crude product was used for next step. MS: 431 (MH+).
... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Secondary amide.Primary alcohol | Primary halide | null | null | c1ccccc1.c1ccnnc1.c1ccccc1 | HO- | ClCCl | null | null | COc1cccc(-c2c(C)c(Cc3ccccc3F)nn(CCO)c2=O)c1.NC(=O)CCC(=O)NBr>ClCCl>COc1cccc(-c2c(C)c(Cc3ccccc3F)nn(CCBr)c2=O)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8b13a4b0757b40a8898d525d3471093f | CC(=O)CC(N)=O.CC(=O)CCc1ccccc1>>Cc1cc(=O)[nH]c(C)c1Cc1ccccc1 | C(C)N(CC)CC.C(CC(=O)C)(=O)N.C(C1=CC=CC=C1)CC(C)=O.C(=O)(O)[O-].[Na+]>>CC1=CC(NC(=C1CC1=CC=CC=C1)C)=O | O=[C:2]([CH3:1])[CH2:3][C:4](=[O:5])[NH2:6].O=[C:7]([CH3:8])[CH2:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][c:2]1[cH:3][c:4](=[O:5])[nH:6][c:7]([CH3:8])[c:9]1[CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | CC(=O)CC(N)=O.CC(=O)CCc1ccccc1 | Cc1cc(=O)[nH]c(C)c1Cc1ccccc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | b2102c13f169246c5fe8ffd69c8ad8da352abb9558cb6f061dbf87baa4772c09 | cdc788bdba482cc2c9ffd89eee5afbfeead5621988d88b4abcccc085cefd94a3 | O=c1ccc(Cc2ccccc2)c[nH]1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH2;D2;+0:3]-[C;H0;D3;+0:4](-[NH2;D1;+0:5])=[O;D1;H0:6].O=[C;H0;D3;+0:7](-[C;D1;H3:8])-[CH2;D2;+0:9]-[C:10]-[c:11]>>[C;D1;H3:2]-[c;H0;D3;+0:1]1:[cH;D2;+0:3]:[c;H0;D3;+0:4](=[O;D1;H0:6]):[nH;D2;+0:5]:[c;H0;D3;+0:7](-[C;D1;H3:8]):[c;H0;D3;+0:9]:1-[C:10]-[c:11] | 53.8 | [{"value": 53.8, "product": "CC1=CC(NC(=C1CC1=CC=CC=C1)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.7, "product": "CC1=CC(NC(=C1CC1=CC=CC=C1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 125 | CELSIUS | null | null | To a mixture of PPA (10 g) and acetoacetamide triethylamine (2.02 g, 20 mmol) was added benzylacetone (5.92 g, 5.98 mL, 40 mmol). The resulting mixture was heated at 125° C. for 3 hours. The brown mixture was poured onto crushed ice and neutralized with solid NaHCO3. The mixture was filtered to give a yellow solid, whi... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Primary amide | null | null | c1cccnc1 | c1cccnc1.c1ccccc1 | HO- | null | 125 | null | CC(=O)CC(N)=O.CC(=O)CCc1ccccc1>>Cc1cc(=O)[nH]c(C)c1Cc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d8e9a1700e45465cbda2d0a58ec838a6 | BrBr.Cc1cc(=O)[nH]c(C)c1Cc1ccccc1>>Cc1[nH]c(=O)c(Br)c(C)c1Cc1ccccc1 | N#N.CC1=CC(NC(=C1CC1=CC=CC=C1)C)=O.BrBr>>CC1=C(C(NC(=C1CC1=CC=CC=C1)C)=O)Br | Br[Br:7].[CH3:1][c:2]1[nH:3][c:4](=[O:5])[cH:6][c:8]([CH3:9])[c:10]1[CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH3:1][c:2]1[nH:3][c:4](=[O:5])[c:6]([Br:7])[c:8]([CH3:9])[c:10]1[CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | BrBr.Cc1cc(=O)[nH]c(C)c1Cc1ccccc1 | Cc1[nH]c(=O)c(Br)c(C)c1Cc1ccccc1 | null | null | C(C)(=O)O | Functional Group Interconversion | Bromination | f63fbe5668c3da6d73cce6f10b3e54926f6839a19c12cb46764f159579089aea | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | O=c1ccc(Cc2ccccc2)c[nH]1 | Br-[Br;H0;D1;+0:1].[C;D1;H3:2]-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7](=[O;D1;H0:8]):[cH;D2;+0:9]:1>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:9]1:[c:7](=[O;D1;H0:8]):[#7;a:6]:[c:5]:[c:4]:[c:3]:1-[C;D1;H3:2] | 104.3 | [{"value": 100.0, "product": "CC1=C(C(NC(=C1CC1=CC=CC=C1)C)=O)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 104.3, "product": "CC1=C(C(NC(=C1CC1=CC=CC=C1)C)=O)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 4,6-dimethyl-5-benzyl-1H-pyridin-2-one (2.21 g, 10.4 mmol) in anhydrous acetic acid (10 mL) was added bromine (3.3 g, 1.06 mL, 20.7 mL). It was stirred at room temperature for one hour. Then the reaction vessel was blew N2 to remove bromine and evaporation removed volatiles. The residue was partitioned... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1cccnc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | HBr | C(C)(=O)O | null | 1 | BrBr.Cc1cc(=O)[nH]c(C)c1Cc1ccccc1>C(C)(=O)O>Cc1[nH]c(=O)c(Br)c(C)c1Cc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-13068739581c41bd9f653f3721546bda | CS(=O)(=O)Cl.OC[C@H]1COc2cccnc2O1>>CS(=O)(=O)OC[C@@H]1COc2cccnc2O1 | CS(=O)(=O)Cl.O1C[C@@H](OC2=NC=CC=C21)CO.C(C)N(CC)CC>>CS(=O)(=O)OC[C@@H]1COC=2C(=NC=CC2)O1 | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][C@H:7]1[CH2:8][O:9][c:10]2[cH:11][cH:12][cH:13][n:14][c:15]2[O:16]1>>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][C@@H:7]1[CH2:8][O:9][c:10]2[cH:11][cH:12][cH:13][n:14][c:15]2[O:16]1 | CS(=O)(=O)Cl.OC[C@H]1COc2cccnc2O1 | CS(=O)(=O)OC[C@@H]1COc2cccnc2O1 | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1cnc2c(c1)OCCO2 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#8:5]-[C:6]-[C:7]-[OH;D1;+0:8]>>[#8:5]-[C:6]-[C:7]-[O;H0;D2;+0:8]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 88.6 | [{"value": 88.6, "product": "CS(=O)(=O)OC[C@@H]1COC=2C(=NC=CC2)O1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | A mixture of intermediate (2-a) (0.023 mol) and triethylamine (0.046 mol) in DCM (40 ml) was stirred at 0° C. A mixure of methanesulfonyl chloride (0.035 mol) in DCM (10 ml) was added dropwise. The mixture was stirred on an ice bath for 2 hours and then washed with H2O/NaCl. The organic layer was dried, filtered and th... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | c1cnc2c(c1)OCCO2 | HCl | C(Cl)Cl | 0 | null | CS(=O)(=O)Cl.OC[C@H]1COc2cccnc2O1>C(Cl)Cl>CS(=O)(=O)OC[C@@H]1COc2cccnc2O1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-52bd9af9abde4dd88619b3dcdc6bb275 | COC(=O)C1Oc2cccnc2O1>>OCC1Oc2cccnc2O1 | [NH4+].[Cl-].O1C(OC2=NC=CC=C21)C(=O)OC.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>O1C(OC2=NC=CC=C21)CO | CO[C:2](=[O:1])[CH:3]1[O:4][c:5]2[cH:6][cH:7][cH:8][n:9][c:10]2[O:11]1>>[OH:1][CH2:2][CH:3]1[O:4][c:5]2[cH:6][cH:7][cH:8][n:9][c:10]2[O:11]1 | COC(=O)C1Oc2cccnc2O1 | OCC1Oc2cccnc2O1 | null | null | O.C(C)(=O)OCC.C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1cnc2c(c1)OCO2 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]1-[#8:4]-[c:5](:[#7;a:6]):[c:7]-[#8:8]-1>>[#7;a:6]:[c:5]1:[c:7]-[#8:8]-[C:3](-[CH2;D2;+0:1]-[OH;D1;+0:2])-[#8:4]-1 | 43.2 | [{"value": 43.2, "product": "O1C(OC2=NC=CC=C21)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Reaction under a nitrogen atmosphere. A solution of intermediate (4) (0.042 mol) in THF (48 ml) was added dropwise to LiAlH4 (1 Min THF) (0.0466 mol) and cooled with an ice-water bath. The resulting reaction mixture was stirred for one hour at room temperature. The reaction mixture was treated carefully with a 10% NH4C... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1cnc2c(c1)OCO2 | Other | O.C(C)(=O)OCC.C1CCOC1 | null | 1 | COC(=O)C1Oc2cccnc2O1>O.C(C)(=O)OCC.C1CCOC1>OCC1Oc2cccnc2O1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a094a34095174cc381d440ed23ac3e00 | CS(=O)(=O)Cl.OCC1Oc2cccnc2O1>>CS(=O)(=O)OCC1Oc2cccnc2O1 | O1C(OC2=NC=CC=C21)CO.C(C)N(CC)CC.CS(=O)(=O)Cl>>CS(=O)(=O)OCC1OC=2C(=NC=CC2)O1 | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][CH:7]1[O:8][c:9]2[cH:10][cH:11][cH:12][n:13][c:14]2[O:15]1>>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][CH:7]1[O:8][c:9]2[cH:10][cH:11][cH:12][n:13][c:14]2[O:15]1 | CS(=O)(=O)Cl.OCC1Oc2cccnc2O1 | CS(=O)(=O)OCC1Oc2cccnc2O1 | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1cnc2c(c1)OCO2 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#8:5]-[C:6](-[C:7]-[OH;D1;+0:8])-[#8:9]>>[#8:5]-[C:6](-[C:7]-[O;H0;D2;+0:8]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4])-[#8:9] | 100.9 | [{"value": 100.9, "product": "CS(=O)(=O)OCC1OC=2C(=NC=CC2)O1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of intermediate (5) (0.018 mol) and triethyl amine (0.036 mol) in DCM (80 ml) was stirred and cooled with an ice-water bath. Methanesulfonyl chloride (0.027 mol) was added dropwise and the resulting reaction mixture was stirred for one hour while cooling on an ice-bath. The crude reaction mixture was washed ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | c1cnc2c(c1)OCO2 | HCl | C(Cl)Cl | null | 1 | CS(=O)(=O)Cl.OCC1Oc2cccnc2O1>C(Cl)Cl>CS(=O)(=O)OCC1Oc2cccnc2O1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-55ae6d3dbf894db8b54952ca5af88cf3 | C=CCO.COCOc1cnccc1Cl>>C=CCOc1ccncc1OCOC | COCOC=1C=NC=CC1Cl.C(C=C)O.[H-].[Na+]>>COCOC=1C=NC=CC1OCC=C | [CH2:1]=[CH:2][CH2:3][OH:4].Cl[c:5]1[cH:6][cH:7][n:8][cH:9][c:10]1[O:11][CH2:12][O:13][CH3:14]>>[CH2:1]=[CH:2][CH2:3][O:4][c:5]1[cH:6][cH:7][n:8][cH:9][c:10]1[O:11][CH2:12][O:13][CH3:14] | C=CCO.COCOc1cnccc1Cl | C=CCOc1ccncc1OCOC | null | null | COCCOC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | ea617b323b892eda23f5ae30e789991ea9692064ef355a16e8ed81c16e743d2b | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccncc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[#8:7].[C;D1;H2:8]=[C:9]-[C:10]-[OH;D1;+0:11]>>[#8:7]-[c:6]1:[c:5]:[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[O;H0;D2;+0:11]-[C:10]-[C:9]=[C;D1;H2:8] | 54.2 | [{"value": 54.2, "product": "COCOC=1C=NC=CC1OCC=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | Under nitrogen atmosphere. 2-propen-1-ol (0.002 mol) was added dropwise to a stirred mixture of NaH 60% (0.002 mol) in DME (5ml). The mixture was stirred at room temperature for 15 minutes. A solution of 3-(methoxymethoxy)-4-chloropyridine (0.0017 mol) in DME (5 ml) was added dropwise. The resulting reaction mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccncc1 | c1ccncc1 | c1ccncc1 | HCl | COCCOC | null | 0.25 | C=CCO.COCOc1cnccc1Cl>COCCOC>C=CCOc1ccncc1OCOC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8fb04d6901e243ce83f9b846bd236967 | COCOc1cnccc1OCC(Br)CBr>>Oc1cnccc1OCC(Br)CBr | BrC(COC1=C(C=NC=C1)OCOC)CBr.Cl>>BrC(COC1=C(C=NC=C1)O)CBr | COC[O:1][c:2]1[cH:3][n:4][cH:5][cH:6][c:7]1[O:8][CH2:9][CH:10]([Br:11])[CH2:12][Br:13]>>[OH:1][c:2]1[cH:3][n:4][cH:5][cH:6][c:7]1[O:8][CH2:9][CH:10]([Br:11])[CH2:12][Br:13] | COCOc1cnccc1OCC(Br)CBr | Oc1cnccc1OCC(Br)CBr | null | null | C(C)O | Reduction | OtherReaction | 92f30feec6876d2f8c7439342f0f488fd5811a8fdb3b3cb63d7289bd57242715 | 3165f563067f8d27bb50b0da034e3e854d1ead7f745de7cf575f7ca4cf677789 | c1ccncc1 | C-O-C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6] | 55.4 | [{"value": 55.4, "product": "BrC(COC1=C(C=NC=C1)O)CBr", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of intermediate (8) (0.0248 mol), HCl (35.42 ml)and ethanol (40 ml) was stirred at room temperature overnight. The reaction mixture was concentrated under vacuum. The concentrate was cooled on an ice-water bath. The mixture was neutralized with a saturated NaHCO3 solution and extracted with ethyl acetate. The... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol | null | null | c1ccncc1 | HO- | C(C)O | null | 8 | COCOc1cnccc1OCC(Br)CBr>C(C)O>Oc1cnccc1OCC(Br)CBr |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4a1d3a61ac65482faaad1b568ca78b0e | Oc1cnccc1OCC(Br)CBr>>BrCC1COc2ccncc2O1 | BrC(COC1=C(C=NC=C1)O)CBr.C(=O)(O)[O-].[Na+]>>BrCC1COC2=C(C=NC=C2)O1 | Br[CH:3]([CH2:2][Br:1])[CH2:4][O:5][c:6]1[cH:7][cH:8][n:9][cH:10][c:11]1[OH:12]>>[Br:1][CH2:2][CH:3]1[CH2:4][O:5][c:6]2[cH:7][cH:8][n:9][cH:10][c:11]2[O:12]1 | Oc1cnccc1OCC(Br)CBr | BrCC1COc2ccncc2O1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | f4643c98d3fbb3e020f3059aacbfe64fa7986154641510e15c8b2587fd92d396 | cf768afb66ed5041aefdce1fa6d1e40995a1ab7c4b4a4ca47544fe49ee1e629f | c1cc2c(cn1)OCCO2 | Br-[CH;D3;+0:1](-[C:2]-[Br;D1;H0:3])-[C:4]-[#8:5]-[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]:[#7;a:10]:[c:11]>>[Br;D1;H0:3]-[C:2]-[CH;D3;+0:1]1-[C:4]-[#8:5]-[c:6]:[c:7](:[c:9]:[#7;a:10]:[c:11])-[O;H0;D2;+0:8]-1 | 67.7 | [{"value": 67.7, "product": "BrCC1COC2=C(C=NC=C2)O1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of intermediate (9) (0.0097 mol) in ethanol (50 ml) was stirred and refluxed overnight. NaHCO3 (0.0097 mol) was added and the resulting reaction mixture was stirred and refluxed overnight. The solvent was evaporated. The residue was washed with water and extracted with DCM. The organic layer was dried, filte... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic alcohol | Ether | null | c1cc2c(cn1)OCCO2 | c1cc2c(cn1)OCCO2 | HBr | C(C)O | null | null | Oc1cnccc1OCC(Br)CBr>C(C)O>BrCC1COc2ccncc2O1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2579d2b9ed544c63b1824890ac07c44c | C=CC#N.CC(C)(CN)CN>>CC(C)(CN)CNCCC#N | CC(CN)(CN)C.C(C=C)#N.CC(CN)(CN)C.C(C=C)#N>>NCC(CNCCC#N)(C)C | [CH2:8]=[CH:9][C:10]#[N:11].[CH3:1][C:2]([CH3:3])([CH2:4][NH2:5])[CH2:6][NH2:7]>>[CH3:1][C:2]([CH3:3])([CH2:4][NH2:5])[CH2:6][NH:7][CH2:8][CH2:9][C:10]#[N:11] | C=CC#N.CC(C)(CN)CN | CC(C)(CN)CNCCC#N | null | null | C(C)O | Heteroatom Alkylation and Arylation | aza-Michael addition primary | b45dd075b7e75caee6dc0a68cb402266c75e0848f7502f06a5dbd8a34863aae2 | 2e45960e6468a140db4162555f247a2535630c23e1aa16e082b84ce22691ebbf | null | [CH2;D1;+0:1]=[CH;D2;+0:2]-[C:3]#[N;D1;H0:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[C:3]#[N;D1;H0:4] | 79.6 | [{"value": 79.6, "product": "NCC(CNCCC#N)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of 2,2 dimethyl-1,3-propanediamine (0.22 mol) and 2-propenenitrile (0.22 mol) in ethanol (250 ml) was stirred overnight at room temperature. The solvent was evaporated. A mixture of 2,2-dimethyl-1,3-propanediamine (0.28 mol) and 2-propenenitrile (0.28 mol) in ethanol (250 ml) was stirred for one hour at room ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Vinyl | Secondary amine | null | null | null | null | C(C)O | null | 8 | C=CC#N.CC(C)(CN)CN>C(C)O>CC(C)(CN)CNCCC#N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9d4167a8912c427091dedcf06cd80dc8 | C=CC#N.NC1(CO)CCN(Cc2ccccc2)CC1>>N#CCCNC1(CO)CCN(Cc2ccccc2)CC1 | C(C=C)#N.NC1(CCN(CC1)CC1=CC=CC=C1)CO.C(C=C)#N.C(C=C)#N>>OCC1(CCN(CC1)CC1=CC=CC=C1)NCCC#N | [N:1]#[C:2][CH:3]=[CH2:4].[NH2:5][C:6]1([CH2:7][OH:8])[CH2:9][CH2:10][N:11]([CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19][CH2:20]1>>[N:1]#[C:2][CH2:3][CH2:4][NH:5][C:6]1([CH2:7][OH:8])[CH2:9][CH2:10][N:11]([CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19][CH2:20]1 | C=CC#N.NC1(CO)CCN(Cc2ccccc2)CC1 | N#CCCNC1(CO)CCN(Cc2ccccc2)CC1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | aza-Michael addition primary | b45dd075b7e75caee6dc0a68cb402266c75e0848f7502f06a5dbd8a34863aae2 | 2e45960e6468a140db4162555f247a2535630c23e1aa16e082b84ce22691ebbf | c1ccc(CN2CCCCC2)cc1 | [CH2;D1;+0:1]=[CH;D2;+0:2]-[C:3]#[N;D1;H0:4].[C:5]-[C:6](-[C:7])(-[NH2;D1;+0:8])-[C:9]>>[C:5]-[C:6](-[C:7])(-[NH;D2;+0:8]-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[C:3]#[N;D1;H0:4])-[C:9] | null | [] | null | null | null | null | A mixture of 4-amino-1-(phenylmethyl)-4-piperidinemethanol (0.0182 mol) and 2-propenenitrile (0.0304 mol) in ethanol (80 ml) was stirred and refluxed for two days. 2-Propenenitrile (2 ml) was added. The mixture was stirred and refluxed for 5 hours. 2-Propenenitrile (2 ml) was added again. The mixture was stirred and re... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Vinyl | Secondary amine | null | null | C1CC[NH]CC1.c1ccccc1 | null | C(C)O | null | null | C=CC#N.NC1(CO)CCN(Cc2ccccc2)CC1>C(C)O>N#CCCNC1(CO)CCN(Cc2ccccc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-46e7da05dc1e4904ba0a0abab488250d | N#CCCNC1(CO)CCN(Cc2ccccc2)CC1>>NCCCNC1(CO)CCN(Cc2ccccc2)CC1 | [H][H].OCC1(CCN(CC1)CC1=CC=CC=C1)NCCC#N.N>>NCCCNC1(CCN(CC1)CC1=CC=CC=C1)CO | [N:1]#[C:2][CH2:3][CH2:4][NH:5][C:6]1([CH2:7][OH:8])[CH2:9][CH2:10][N:11]([CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19][CH2:20]1>>[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1([CH2:7][OH:8])[CH2:9][CH2:10][N:11]([CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19][CH2:20]1 | N#CCCNC1(CO)CCN(Cc2ccccc2)CC1 | NCCCNC1(CO)CCN(Cc2ccccc2)CC1 | null | [Ni] | CO | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | c1ccc(CN2CCCCC2)cc1 | [C:1]-[C:2]-[C;H0;D2;+0:3]#[N;H0;D1;+0:4]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[NH2;D1;+0:4] | 86.2 | [{"value": 86.2, "product": "NCCCNC1(CCN(CC1)CC1=CC=CC=C1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of intermediate (14) (0.0159 mol) in methanol saturated with NH3 (150 ml) was hydrogenated at 14° C. with Raney nickel (½ spoon) as a catalyst. After uptake of hydrogen (2 equivalents), the catalyst was filtered off and the filtrate was evaporated, yielding 3.8 g of 4-[(3-aminopropyl)amino]-1-(phenylmethyl)-4... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | C1CC[NH]CC1.c1ccccc1 | null | [Ni].CO | null | null | N#CCCNC1(CO)CCN(Cc2ccccc2)CC1>[Ni].CO>NCCCNC1(CO)CCN(Cc2ccccc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e31df8ebcd91409b97b45604f0093f7e | NCCCNC1(CO)CCN(Cc2ccccc2)CC1.O=C(n1ccnc1)n1ccnc1>>O=C1NCCCN1C1(CO)CCN(Cc2ccccc2)CC1 | C(=O)(N1C=NC=C1)N1C=NC=C1.NCCCNC1(CCN(CC1)CC1=CC=CC=C1)CO>>OCC1(CCN(CC1)CC1=CC=CC=C1)N1C(NCCC1)=O | [NH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]1([CH2:9][OH:10])[CH2:11][CH2:12][N:13]([CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:21][CH2:22]1.c1cn([C:2](n2ccnc2)=[O:1])cn1>>[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][CH2:6][N:7]1[C:8]1([CH2:9][OH:10])[CH2:11][CH2:12][N:13]([CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]... | NCCCNC1(CO)CCN(Cc2ccccc2)CC1.O=C(n1ccnc1)n1ccnc1 | O=C1NCCCN1C1(CO)CCN(Cc2ccccc2)CC1 | null | null | C1CCOC1 | Acylation | OtherReaction | 57b05020c91f5cbcbf12dad7925c21eec46f26a456a38df2d6da259ef3d4778c | 092fb1988ce3c31a0210cc9ec123f317c79841c29a05a3f2098134944f12c379 | O=C1NCCCN1C1CCN(Cc2ccccc2)CC1 | [C:1]-[C:2](-[C:3])(-[NH;D2;+0:4]-[C:5]-[C:6]-[C:7]-[NH2;D1;+0:8])-[C:9].[O;D1;H0:10]=[C;H0;D3;+0:11](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[C:1]-[C:2](-[C:3])(-[N;H0;D3;+0:4]1-[C:5]-[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:11]-1=[O;D1;H0:10])-[C:9] | 49.3 | [{"value": 49.3, "product": "OCC1(CCN(CC1)CC1=CC=CC=C1)N1C(NCCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 1,1′-Carbonylbis-1H-imidazole (0.0149 mol) was added to a mixture of intermediate (15) (0.0137 mol) in THF (40 ml). The mixture was stirred at room temperature overnight. The precipitate was filtered off, crystallized from ACN, filtered off, washed with ACN and DIPE and then dried, yielding 2.05 g of tetrahydro-1-[4-(h... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine | Urea | c1c[nH]cn1.c1c[nH]cn1 | C1CNC[NH]C1 | C1CNC[NH]C1.C1CC[NH]CC1.c1ccccc1 | Other | C1CCOC1 | null | 8 | NCCCNC1(CO)CCN(Cc2ccccc2)CC1.O=C(n1ccnc1)n1ccnc1>C1CCOC1>O=C1NCCCN1C1(CO)CCN(Cc2ccccc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a22ad81d826e47c9accc03b29bb160d2 | O=C1NCCCN1C1(CO)CCN(Cc2ccccc2)CC1>>O=C1NCCCN1C1(CO)CCNCC1 | OCC1(CCN(CC1)CC1=CC=CC=C1)N1C(NCCC1)=O.[H][H]>>OCC1(CCNCC1)N1C(NCCC1)=O | c1ccc(C[N:13]2[CH2:12][CH2:11][C:8]([N:7]3[C:2](=[O:1])[NH:3][CH2:4][CH2:5][CH2:6]3)([CH2:9][OH:10])[CH2:15][CH2:14]2)cc1>>[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][CH2:6][N:7]1[C:8]1([CH2:9][OH:10])[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]1 | O=C1NCCCN1C1(CO)CCN(Cc2ccccc2)CC1 | O=C1NCCCN1C1(CO)CCNCC1 | null | [Pd] | CO | Deprotection | Hydrogenolysis of tertiary amines | cd3c1aa319cad45f383f17cc0b8bfc8337d7078d779f654933f9a447e64292a5 | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | O=C1NCCCN1C1CCNCC1 | [C:1]-[C:2]-[N;H0;D3;+0:3](-C-c1:c:c:c:c:c:1)-[C:4]-[C:5]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C:4]-[C:5] | 47.7 | [{"value": 47.7, "product": "OCC1(CCNCC1)N1C(NCCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of intermediate (16) (0.0059 mol) in methanol (100 ml) was hydrogenated with palladium on carbon (1 g) as a catalyst. After uptake of hydrogen (1 equivalent), the catalyst was filtered off, the filtrate was evaporated and crystallized from ACN, yielding 0.6 g of tetrahydro-1-[4(hydroxymethyl)-4-piperidinyl]-2... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.C1CC[NH]CC1 | C1CCNCC1 | C1CNC[NH]C1.C1CCNCC1 | Other | [Pd].CO | null | null | O=C1NCCCN1C1(CO)CCN(Cc2ccccc2)CC1>[Pd].CO>O=C1NCCCN1C1(CO)CCNCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a9967f9e01b644cebaf2b22cfd6b0467 | C=CCN1CC(=O)NC1=O>>O=C1CN(CC2CO2)C(=O)N1 | C(=O)([O-])[O-].[Na+].[Na+].C(C=C)N1C(NC(C1)=O)=O.ClC=1C=C(C=CC1)C(=O)OO.S([O-])(O)=O>>O1C(C1)CN1C(NC(C1)=O)=O | [O:1]=[C:2]1[CH2:3][N:4]([CH2:5][CH:6]=[CH2:7])[C:9](=[O:10])[NH:11]1>>[O:1]=[C:2]1[CH2:3][N:4]([CH2:5][CH:6]2[CH2:7][O:8]2)[C:9](=[O:10])[NH:11]1 | C=CCN1CC(=O)NC1=O | O=C1CN(CC2CO2)C(=O)N1 | null | null | C(Cl)Cl | Oxidation | OtherReaction | ccc410867e4c89598d5079c0dfc27f7bc863046b1c1459e93fa3815bf371d797 | 38c38e5e943ba321612c1e8763ee5b6d3bec0e5b922509df80b788fc9703980f | O=C1CN(CC2CO2)C(=O)N1 | [CH2;D1;+0:1]=[CH;D2;+0:2]-[C:3]-[#7:4]-[C:5]=[O;D1;H0:6]>>[O;D1;H0:6]=[C:5]-[#7:4]-[C:3]-[CH;D3;+0:2]1-[#8:7]-[CH2;D2;+0:1]-1 | 89 | [{"value": 89.0, "product": "O1C(C1)CN1C(NC(C1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | A reaction solution of 1-(2-propenyl)-2,4-imidazolidinedione (0.036 mol) and 3-chloro-benzenecarboperoxoic acid (0.043 mol, 70.75%) in DCM (25 ml) was stirred for 2 hours at room temperature. An aqueous solution of bisulfite was added and the mixture was stirred for 10 minutes. Na2CO3 was added and this mixture was ext... | 10.6084/m9.figshare.5104873.v1 | null | Allyl | Ether | null | C1CO1 | C1C[NH]CN1.C1CO1 | Other | C(Cl)Cl | null | 0.166667 | C=CCN1CC(=O)NC1=O>C(Cl)Cl>O=C1CN(CC2CO2)C(=O)N1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d050e9c621754d0090d82aad60627c10 | ClCC1CO1.Oc1cccnc1Cl>>Clc1ncccc1OCC1CO1 | O.ClCC1OC1.Cl.ClC1=NC=CC=C1O.[H-].[Na+]>>ClC1=NC=CC=C1OCC1OC1 | Cl[CH2:9][CH:10]1[CH2:11][O:12]1.[Cl:1][c:2]1[n:3][cH:4][cH:5][cH:6][c:7]1[OH:8]>>[Cl:1][c:2]1[n:3][cH:4][cH:5][cH:6][c:7]1[O:8][CH2:9][CH:10]1[CH2:11][O:12]1 | ClCC1CO1.Oc1cccnc1Cl | Clc1ncccc1OCC1CO1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1cncc(OCC2CO2)c1 | Cl-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1.[Cl;D1;H0:5]-[c:6](:[#7;a:7]:[c:8]):[c:9](-[OH;D1;+0:10]):[c:11]>>[Cl;D1;H0:5]-[c:6](:[#7;a:7]:[c:8]):[c:9](-[O;H0;D2;+0:10]-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1):[c:11] | 194.4 | [{"value": 194.4, "product": "ClC1=NC=CC=C1OCC1OC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Reaction was carried out under nitrogen flow. A mixture of 2-chloro-3-pyridinol hydrochloride (1:1) (1.760 mol) in DMF (1000 ml) was added dropwise in 30 minutes to a mixture of NaH 60% (1.934 mol) in DMF (1200 ml) (temperature below 27° C.). The reaction mixture was stirred for 30 minutes. (Chloromethyl)-oxirane (3.53... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccncc1.C1CO1 | HCl | CN(C)C=O | null | 0.5 | ClCC1CO1.Oc1cccnc1Cl>CN(C)C=O>Clc1ncccc1OCC1CO1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f0951644cba643059e43008a1e0b23cf | Clc1ncccc1OCC1CO1.OCc1ccccc1>>C=C/C=C\CCOCC(O)COc1cccnc1Cl | ClC1=NC=CC=C1OCC1OC1.C1CCOC1.C1(=CC=CC=C1)CO.[OH-].[Na+]>>ClC1=NC=CC=C1OCC(COCC\C=C/C=C)O | [CH2:8]1[CH:9]([CH2:11][O:12][c:13]2[cH:14][cH:15][cH:16][n:17][c:18]2[Cl:19])[O:10]1.c1[cH:1][cH:2][cH:3][cH:4][c:5]1[CH2:6][OH:7]>>[CH2:1]=[CH:2]/[CH:3]=[CH:4]\[CH2:5][CH2:6][O:7][CH2:8][CH:9]([OH:10])[CH2:11][O:12][c:13]1[cH:14][cH:15][cH:16][n:17][c:18]1[Cl:19] | Clc1ncccc1OCC1CO1.OCc1ccccc1 | C=C/C=C\CCOCC(O)COc1cccnc1Cl | null | null | O | Functional Group Interconversion | OtherReaction | 08d986e85e248a77573253bc1bd35c6979479678e0e5c2c4618bb6cac4dbaec1 | 1eaac4c438ebea37734abc461df3eafd66a8a51fd24d58b9a1b5b047bf2c6ff8 | c1ccncc1 | [C:1]-[C:2]1-[CH2;D2;+0:3]-[O;H0;D2;+0:4]-1.[OH;D1;+0:5]-[C:6]-[c;H0;D3;+0:7]1:[cH;D2;+0:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:c:1>>[C:1]-[C:2](-[OH;D1;+0:4])-[CH2;D2;+0:3]-[O;H0;D2;+0:5]-[C:6]-[CH2;D2;+0:7]/[CH;D2;+0:8]=[CH;D2;+0:9]\[CH;D2;+0:10]=[CH2;D1;+0:11] | 38 | [{"value": 38.0, "product": "ClC1=NC=CC=C1OCC(COCC\\C=C/C=C)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A mixture of THF (915 ml), benzenemethanol (2.96 mol) and NaOH (2.36 mol) was stirred at room temperature for 30 minutes (cooling was required to keep the temperature below 25° C.). Intermediate (19) (1.97 mol) was added. The reaction mixture was stirred at room temperature for 4 days. Water was added dropwise (cooling... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary alcohol | Ether.Secondary alcohol.Vinyl.Conjugated diene | C1CO1.c1ccccc1 | null | c1ccncc1 | Other | O | null | 0.5 | Clc1ncccc1OCC1CO1.OCc1ccccc1>O>C=C/C=C\CCOCC(O)COc1cccnc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e863c07b645248fda8f4ffad40dc7b47 | C=C(C(=O)O)P(=O)(OCC)OCC.O=Cc1ncccc1O>>CCOC(=O)C1=Cc2ncccc2OC1 | [NH4+].[Cl-].C(C)OP(=O)(C(C(=O)O)=C)OCC.C1CCOC1.[H-].[Na+].C1CCOC1.OC=1C(=NC=CC1)C=O.C1CCOC1>>O1CC(=CC2=NC=CC=C21)C(=O)OCC | CCOP(=O)(O[CH2:2][CH3:1])[C:6]([C:4]([OH:3])=[O:5])=[CH2:15].O=[CH:7][c:8]1[n:9][cH:10][cH:11][cH:12][c:13]1[OH:14]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[CH:7][c:8]2[n:9][cH:10][cH:11][cH:12][c:13]2[O:14][CH2:15]1 | C=C(C(=O)O)P(=O)(OCC)OCC.O=Cc1ncccc1O | CCOC(=O)C1=Cc2ncccc2OC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | c35822cd68bf53c853ab7a1ede5bfc04d46a9c76cf1d473da361362721f47599 | fc2575a0b5bf17c182baee9326f66494e91d02a86703b6684cb158a39ed47b67 | C1=Cc2ncccc2OC1 | C-C-O-P(=O)(-O-[CH2;D2;+0:1]-[C;D1;H3:2])-[C;H0;D3;+0:3](=[CH2;D1;+0:4])-[C:5](=[O;D1;H0:6])-[OH;D1;+0:7].O=[CH;D2;+0:8]-[c:9](:[#7;a:10]:[c:11]):[c:12](-[OH;D1;+0:13]):[c:14]>>[C;D1;H3:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:7]-[C:5](=[O;D1;H0:6])-[C;H0;D3;+0:3]1=[CH;D2;+0:8]-[c:9](:[#7;a:10]:[c:11]):[c:12](:[c:14])-[O;H0;D2;+0:... | null | [] | 0 | CELSIUS | null | null | A mixture of NaH 60% (0.051 mol) in THF (20 ml) was stirred at 0° C. A solution of 3-hydroxy-2-pyridinecarboxaldehyde (0.034 mol) in THF (75 ml) was added dropwise at 0° C. The reaction mixture was stirred for one hour at room temperature. A solution of 2-(diethoxyphosphinyl)-2-propenoic acid, ethyl esther (0.041 mol) ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Carboxylic acid.Aromatic alcohol.Vinyl | Ester.Ether | null | C1=Cc2ncccc2OC1 | C1=Cc2ncccc2OC1 | HO- | null | 0 | null | C=C(C(=O)O)P(=O)(OCC)OCC.O=Cc1ncccc1O>>CCOC(=O)C1=Cc2ncccc2OC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-495ba84ac0e447cda9911ec26109657e | CCOC(=O)C1=Cc2ncccc2OC1>>OCC1=Cc2ncccc2OC1 | O1CC(=CC2=NC=CC=C21)C(=O)OCC.[BH4-].[Na+].[NH4+].[Cl-]>>O1CC(=CC2=NC=CC=C21)CO | CCO[C:2](=[O:1])[C:3]1=[CH:4][c:5]2[n:6][cH:7][cH:8][cH:9][c:10]2[O:11][CH2:12]1>>[OH:1][CH2:2][C:3]1=[CH:4][c:5]2[n:6][cH:7][cH:8][cH:9][c:10]2[O:11][CH2:12]1 | CCOC(=O)C1=Cc2ncccc2OC1 | OCC1=Cc2ncccc2OC1 | null | null | CO.C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | C1=Cc2ncccc2OC1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](=[C:4]-[c:5]:[#7;a:6])-[C:7]-[#8:8]>>[#7;a:6]:[c:5]-[C:4]=[C:3](-[CH2;D2;+0:1]-[OH;D1;+0:2])-[C:7]-[#8:8] | 86.2 | [{"value": 86.2, "product": "O1CC(=CC2=NC=CC=C21)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | A solution of intermediate (24) (0.0032 mol) in methanol (dry) (2 ml) and THF (dry) (16 ml) was stirred at 0° C. NaBH4 (0.0128 mol) was added portionwise at 0° C. The reaction mixture was stirred for 5 hours at room temperature. A 10% NH4Cl solution was added and this mixture was extracted with DCM. The separated organ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1=Cc2ncccc2OC1 | HO- | CO.C1CCOC1 | null | 5 | CCOC(=O)C1=Cc2ncccc2OC1>CO.C1CCOC1>OCC1=Cc2ncccc2OC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b9cbd20a7d6a4baf8ad5eba19664bb6d | OCC1=Cc2ncccc2OC1>>OCC1COc2cccnc2C1 | O1CC(=CC2=NC=CC=C21)CO.[H][H]>>O1CC(CC2=NC=CC=C21)CO | [OH:1][CH2:2][C:3]1=[CH:12][c:11]2[c:6]([cH:7][cH:8][cH:9][n:10]2)[O:5][CH2:4]1>>[OH:1][CH2:2][CH:3]1[CH2:4][O:5][c:6]2[cH:7][cH:8][cH:9][n:10][c:11]2[CH2:12]1 | OCC1=Cc2ncccc2OC1 | OCC1COc2cccnc2C1 | null | [Pd] | CO | Reduction | Hydrogenation (double to single) | 7e489a1fe2ccc21e0d6c692bcb91866ae4946e46ebedca2097faddc137287202 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1cnc2c(c1)OCCC2 | [O;D1;H1:1]-[C:2]-[C;H0;D3;+0:3]1=[CH;D2;+0:4]-[c:5](:[#7;a:6]:[c:7]):[c:8]-[#8:9]-[C:10]-1>>[O;D1;H1:1]-[C:2]-[CH;D3;+0:3]1-[C:10]-[#8:9]-[c:8]:[c:5](:[#7;a:6]:[c:7])-[CH2;D2;+0:4]-1 | 78.5 | [{"value": 78.5, "product": "O1CC(CC2=NC=CC=C21)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of intermediate (25) (0.0027 mol) in methanol (20 ml) was hydrogenated for 24 hours at room temperature with palladium-on-carbon (0.04 g) as a catalyst. After uptake of hydrogen (1 equivalent), the catalyst was filtered off and the filtrate was evaporated, yielding 0.35 g of 3,4-dihydro-2H-pyrano[3,2-b]pyridi... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1=Cc2ncccc2OC1 | c1cnc2c(c1)OCCC2 | c1cnc2c(c1)OCCC2 | null | [Pd].CO | null | null | OCC1=Cc2ncccc2OC1>[Pd].CO>OCC1COc2cccnc2C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f2532a0bdbb646dd95616279880e1369 | CI.Nc1cccnc1Cl>>CNc1cccnc1Cl | [NH4+].[Cl-].IC.ClC1=NC=CC=C1N.C(C)(C)NC(C)C.[Li]>>ClC1=NC=CC=C1NC | I[CH3:1].[NH2:2][c:3]1[cH:4][cH:5][cH:6][n:7][c:8]1[Cl:9]>>[CH3:1][NH:2][c:3]1[cH:4][cH:5][cH:6][n:7][c:8]1[Cl:9] | CI.Nc1cccnc1Cl | CNc1cccnc1Cl | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | 3c2788b3f372b76c1d2ee0d77963cb247b210aa8a28e76637b4e731826c4252a | c6874c6af41d3b1c4f7668e1cd342c90252d0e77f4317d31b3193ebc2f9501a3 | c1ccncc1 | I-[CH3;D1;+0:1].[Cl;D1;H0:2]-[c:3](:[#7;a:4]:[c:5]):[c:6](-[NH2;D1;+0:7]):[c:8]>>[CH3;D1;+0:1]-[NH;D2;+0:7]-[c:6](:[c:8]):[c:3](-[Cl;D1;H0:2]):[#7;a:4]:[c:5] | 89.1 | [{"value": 89.1, "product": "ClC1=NC=CC=C1NC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | To a solution of 2-chloro-3-pyridinamine (0.0465 mol) in THF (45ml) at −78° C. under N2 flow, lithium diisopropylamine (0.0513 mol, 2 M) was added dropwise. The mixture was allowed to warm to 0° C. and was stirred for 1 hour and then cooled to −78° C. Then iodomethane (0.0582 mol) was added and the reaction mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary amine | null | null | c1ccncc1 | HI | C1CCOC1 | 0 | 1 | CI.Nc1cccnc1Cl>C1CCOC1>CNc1cccnc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1e3bc0647e1c48d681068c3311f015d4 | CNc1cccnc1Cl.c1ccc(COCC2CO2)cc1>>OC(CNCc1cccnc1Cl)COCc1ccccc1 | [NH4+].[Cl-].C1(=CC=CC=C1)COCC1OC1.ClC1=NC=CC=C1NC.C(C)(C)NC(C)C.[Li]>>ClC1=NC=CC=C1CNCC(COCC1=CC=CC=C1)O | [NH:4]([CH3:5])[c:6]1[cH:7][cH:8][cH:9][n:10][c:11]1[Cl:12].[O:1]1[CH:2]([CH2:13][O:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[CH2:3]1>>[OH:1][CH:2]([CH2:3][NH:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][n:10][c:11]1[Cl:12])[CH2:13][O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | CNc1cccnc1Cl.c1ccc(COCC2CO2)cc1 | OC(CNCc1cccnc1Cl)COCc1ccccc1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | d439f7e645ce89319ce55258a32a80ac87a862ac0dde93b154e64323356ee2ea | 44f0f98267935086e7e06becbfd88bd9220317f0f521b960be901561fa43c70b | c1ccc(COCCCNCc2cccnc2)cc1 | [CH3;D1;+0:1]-[NH;D2;+0:2]-[c;H0;D3;+0:3]1:[c:4]:[c:5]:[c:6]:[#7;a:7]:[c:8]:1-[Cl;D1;H0:9].[C:10]-[C:11]1-[CH2;D2;+0:12]-[O;H0;D2;+0:13]-1>>[C:10]-[C:11](-[OH;D1;+0:13])-[CH2;D2;+0:12]-[NH;D2;+0:2]-[CH2;D2;+0:1]-[c;H0;D3;+0:3]1:[c:4]:[c:5]:[c:6]:[#7;a:7]:[c:8]:1-[Cl;D1;H0:9] | 75.5 | [{"value": 75.5, "product": "ClC1=NC=CC=C1CNCC(COCC1=CC=CC=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | To a solution of intermediate (28) (0.031 mol) in THF (50 ml) under nitrogen flow at −78° C., lithium diisopropylamine (0.062 mol, 2 M) was slowly added. The reaction mixture was allowed to warm to 0° C. and was stirred for 1 hour. After cooling again to −78° C., a solution of [(phenylmethoxy)methyl]-oxirane (0.034 mol... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Secondary alcohol.Secondary amine | c1ccncc1.C1CO1 | c1ccncc1 | c1ccncc1.c1ccccc1 | null | C1CCOC1 | 0 | 1 | CNc1cccnc1Cl.c1ccc(COCC2CO2)cc1>C1CCOC1>OC(CNCc1cccnc1Cl)COCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7c434df8182b48b2920976e739a5bf0b | BrBr.OCC1COc2cccnc2O1>>OCC1COc2cc(Br)cnc2O1 | BrBr.O1CC(OC2=NC=CC=C21)CO.BrBr>>BrC=1C=C2C(=NC1)OC(CO2)CO | Br[Br:9].[OH:1][CH2:2][CH:3]1[CH2:4][O:5][c:6]2[cH:7][cH:8][cH:10][n:11][c:12]2[O:13]1>>[OH:1][CH2:2][CH:3]1[CH2:4][O:5][c:6]2[cH:7][c:8]([Br:9])[cH:10][n:11][c:12]2[O:13]1 | BrBr.OCC1COc2cccnc2O1 | OCC1COc2cc(Br)cnc2O1 | null | [O-]S(=O)[O-].[Na+].[Na+] | C(=O)([O-])[O-].[Na+].[Na+].C(Cl)Cl | Functional Group Interconversion | Bromination | 53ae098687f59589f7887546d68b8bc2c24e46ec8e7e4682e59ffddd63bb8698 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1cnc2c(c1)OCCO2 | Br-[Br;H0;D1;+0:1].[#8:2]-[c:3]1:[#7;a:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]:1-[#8:9]>>[#8:2]-[c:3]1:[#7;a:4]:[c:5]:[c;H0;D3;+0:6](-[Br;H0;D1;+0:1]):[c:7]:[c:8]:1-[#8:9] | 40.6 | [{"value": 40.6, "product": "BrC=1C=C2C(=NC1)OC(CO2)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Bromine (0.009 mol) was added dropwise to a solution of 2,3-dihydro-1,4-dioxino[2,3-b]pyridine-3-methanol (0.009 mol) in DCM (100 ml) and Na2CO3 saturated solution (50 ml), stirred at room temperature. The reaction mixture was stirred for 16 hours at room temperature. More bromine (0.009 mol) was added and the reaction... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1cnc2c(c1)OCCO2 | c1cnc2c(c1)OCCO2 | c1cnc2c(c1)OCCO2 | HBr | [O-]S(=O)[O-].[Na+].[Na+].C(=O)([O-])[O-].[Na+].[Na+].C(Cl)Cl | null | null | BrBr.OCC1COc2cccnc2O1>[O-]S(=O)[O-].[Na+].[Na+].C(=O)([O-])[O-].[Na+].[Na+].C(Cl)Cl>OCC1COc2cc(Br)cnc2O1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-47a5080b79c24614836794070a39ff48 | CC(C)(C)[Si](C)(C)OCC1COc2cc(Br)cnc2O1.CI>>Cc1cnc2c(c1)OCC(CO[Si](C)(C)C(C)(C)C)O2 | [NH4+].[Cl-].[Li]CCCC.BrC=1C=C2C(=NC1)OC(CO2)CO[Si](C)(C)C(C)(C)C.IC>>CC(C)(C)[Si](OCC1COC=2C(=NC=C(C2)C)O1)(C)C | Br[c:2]1[cH:3][n:4][c:5]2[c:6]([cH:7]1)[O:8][CH2:9][CH:10]([CH2:11][O:12][Si:13]([CH3:14])([CH3:15])[C:16]([CH3:17])([CH3:18])[CH3:19])[O:20]2.I[CH3:1]>>[CH3:1][c:2]1[cH:3][n:4][c:5]2[c:6]([cH:7]1)[O:8][CH2:9][CH:10]([CH2:11][O:12][Si:13]([CH3:14])([CH3:15])[C:16]([CH3:17])([CH3:18])[CH3:19])[O:20]2 | CC(C)(C)[Si](C)(C)OCC1COc2cc(Br)cnc2O1.CI | Cc1cnc2c(c1)OCC(CO[Si](C)(C)C(C)(C)C)O2 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 7d02a1397677532c497b06779094a84b5891e297cb244a69d6935fe65c441acf | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1cnc2c(c1)OCCO2 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4](:[c:5](:[c:6]:1)-[#8:7])-[#8:8].I-[CH3;D1;+0:9]>>[#8:8]-[c:4]1:[#7;a:3]:[c:2]:[c;H0;D3;+0:1](-[CH3;D1;+0:9]):[c:6]:[c:5]:1-[#8:7] | 41.9 | [{"value": 41.9, "product": "CC(C)(C)[Si](OCC1COC=2C(=NC=C(C2)C)O1)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 75 | MINUTE | Reaction under nitrogen atmosphere. A solution of intermediate (37) (0.00194 mol) in THF was cooled to −78° C. BuLi (0.00214 mol, 2.5M) was added dropwise and the mixture was stirred for 75 minutes at −78° C. Then, iodomethane (00214 mol) was added and the reaction mixture was stirred for 45 minutes. A saturated aqueou... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cnc2c(c1)OCCO2 | c1cnc2c(c1)OCCO2 | c1cnc2c(c1)OCCO2 | Br-.I- | C1CCOC1 | -78 | 1.25 | CC(C)(C)[Si](C)(C)OCC1COc2cc(Br)cnc2O1.CI>C1CCOC1>Cc1cnc2c(c1)OCC(CO[Si](C)(C)C(C)(C)C)O2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ae7b455778fa4904bb54a3c6f5dbc473 | CS(=O)(=O)Cl.Cc1cnc2c(c1)OCC(CO)O2>>Cc1cnc2c(c1)OCC(COS(C)(=O)=O)O2 | O.CS(=O)(=O)Cl.CC=1C=C2C(=NC1)OC(CO2)CO.C(C)N(CC)CC>>CS(=O)(=O)OCC1COC=2C(=NC=C(C2)C)O1 | Cl[S:13]([CH3:14])(=[O:15])=[O:16].[CH3:1][c:2]1[cH:3][n:4][c:5]2[c:6]([cH:7]1)[O:8][CH2:9][CH:10]([CH2:11][OH:12])[O:17]2>>[CH3:1][c:2]1[cH:3][n:4][c:5]2[c:6]([cH:7]1)[O:8][CH2:9][CH:10]([CH2:11][O:12][S:13]([CH3:14])(=[O:15])=[O:16])[O:17]2 | CS(=O)(=O)Cl.Cc1cnc2c(c1)OCC(CO)O2 | Cc1cnc2c(c1)OCC(COS(C)(=O)=O)O2 | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1cnc2c(c1)OCCO2 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#8:5]-[C:6]-[C:7]-[OH;D1;+0:8]>>[#8:5]-[C:6]-[C:7]-[O;H0;D2;+0:8]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 99 | [{"value": 99.0, "product": "CS(=O)(=O)OCC1COC=2C(=NC=C(C2)C)O1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | Methanesulfonyl chloride (0.00103 mol) was added to a mixture of intermediate (39) (0.00081 mol) and triethylamine (0.0019 mol) in DCM, stirred at 0° C. The reaction mixture was stirred for 30 minutes at 0° C. Water was added. The organic layer was separated, dried, filtered and the solvent was evaporated, yielding 0.2... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | c1cnc2c(c1)OCCO2 | HCl | C(Cl)Cl | 0 | null | CS(=O)(=O)Cl.Cc1cnc2c(c1)OCC(CO)O2>C(Cl)Cl>Cc1cnc2c(c1)OCC(COS(C)(=O)=O)O2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c3d23e65adee4b12b12b3b4c3cb07888 | BrBr.O=S([O-])[O-].OC[C@H]1COc2cccnc2O1>>OCC1COc2c(Br)ccnc2O1.OC[C@H]1COc2cc(Br)cnc2O1 | [O-]S(=O)[O-].[Na+].[Na+].O1C[C@@H](OC2=NC=CC=C21)CO.BrBr>>BrC=1C=C2C(=NC1)O[C@H](CO2)CO.BrC1=C2C(=NC=C1)OC(CO2)CO | [Br:8][Br:22].S([O-:13])(=[O:14])[O-:18].[OH:1][CH2:2][C@H:16]1[CH2:4][O:5][c:6]2[cH:7][cH:9][cH:10][n:11][c:12]2[O:26]1>>[OH:1][CH2:2][CH:3]1[CH2:4][O:5][c:6]2[c:7]([Br:8])[cH:9][cH:10][n:11][c:12]2[O:13]1.[OH:14][CH2:15][C@H:16]1[CH2:17][O:18][c:19]2[cH:20][c:21]([Br:22])[cH:23][n:24][c:25]2[O:26]1 | BrBr.O=S([O-])[O-].OC[C@H]1COc2cccnc2O1 | OCC1COc2c(Br)ccnc2O1.OC[C@H]1COc2cc(Br)cnc2O1 | null | null | C(=O)([O-])[O-].[Na+].[Na+].C(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | 06ddb3b84b1199052de7ea93a55acafccf7f1846e13a606e13fa1ca33162d4d4 | 767e0fc4b9104315cd7ac1893fa5e383fffd5da088a777a015169e9731cb9302 | c1cnc2c(c1)OCCO2.c1cnc2c(c1)OCCO2 | [Br;H0;D1;+0:1]-[Br;H0;D1;+0:2].[O-;H0;D1:3]-S(-[O-;H0;D1:4])=[O;H0;D1;+0:5].[O;D1;H1:6]-[CH2;D2;+0:7]-[C@H;D3;+0:8]1-[CH2;D2;+0:9]-[#8:10]-[c:11]2:[cH;D2;+0:12]:[c:13]:[c:14]:[#7;a:15]:[c;H0;D3;+0:16]:2-[O;H0;D2;+0:17]-1>>[Br;H0;D1;+0:2]-[c;H0;D3;+0:12]1:[c:13]:[c:14]:[#7;a:15]:[c;H0;D3;+0:16]2:[c:11]:1-[#8:10]-[CH2;D... | null | [] | null | null | 16 | HOUR | To a solution of intermediate (2-a) (0.03 mol) in DCM (50 ml) and Na2CO3 saturated (50 ml), bromine (0.09 mol) was added dropwise and the reaction mixture was stirred for 16 hours at room temperature. Then a Na2SO3-solution (10%) was added and the mixture was stirred for 5 minutes at room temperature and then neutraliz... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Primary alcohol | Aromatic halide.Aromatic halide.Ether.Ether.Ether.Ether.Primary alcohol.Primary alcohol | c1cnc2c(c1)OCCO2 | c1cnc2c(c1)OCCO2.c1cnc2c(c1)OCCO2 | c1cnc2c(c1)OCCO2.c1cnc2c(c1)OCCO2 | null | C(=O)([O-])[O-].[Na+].[Na+].C(Cl)Cl | null | 16 | BrBr.O=S([O-])[O-].OC[C@H]1COc2cccnc2O1>C(=O)([O-])[O-].[Na+].[Na+].C(Cl)Cl>OCC1COc2c(Br)ccnc2O1.OC[C@H]1COc2cc(Br)cnc2O1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7a5b96a352424d638904a6a376f3d613 | CS(=O)(=O)Cl.OCC1COc2c(Br)ccnc2O1>>CS(=O)(=O)OC[C@@H]1COc2c(Br)ccnc2O1 | BrC1=C2C(=NC=C1)OC(CO2)CO.C(C)N(CC)CC.CS(=O)(=O)Cl>>CS(=O)(=O)OC[C@@H]1COC=2C(=NC=CC2Br)O1 | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][CH:7]1[CH2:8][O:9][c:10]2[c:11]([Br:12])[cH:13][cH:14][n:15][c:16]2[O:17]1>>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][C@@H:7]1[CH2:8][O:9][c:10]2[c:11]([Br:12])[cH:13][cH:14][n:15][c:16]2[O:17]1 | CS(=O)(=O)Cl.OCC1COc2c(Br)ccnc2O1 | CS(=O)(=O)OC[C@@H]1COc2c(Br)ccnc2O1 | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1cnc2c(c1)OCCO2 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#8:5]-[C:6]-[C:7]-[OH;D1;+0:8]>>[#8:5]-[C:6]-[C:7]-[O;H0;D2;+0:8]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 92.6 | [{"value": 92.6, "product": "CS(=O)(=O)OC[C@@H]1COC=2C(=NC=CC2Br)O1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a mixture of intermediate (42) (0.0014 mol) and triethylamine (0.0028 mol) in DCM (5 ml), methanesulfonyl chloride (0.0021 mol) was slowly added at room temperature. The reaction mixture was stirred for 16 hours and was then extracted with water. The separated organic layer was dried, filtered and the solvent was ev... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | c1cnc2c(c1)OCCO2 | HCl | C(Cl)Cl | null | 16 | CS(=O)(=O)Cl.OCC1COc2c(Br)ccnc2O1>C(Cl)Cl>CS(=O)(=O)OC[C@@H]1COc2c(Br)ccnc2O1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1cb28e245e6246579ac3aca6c012a0d0 | C=CCO.Oc1cnccc1Cl>>C=CCOc1cnccc1Cl | ClC1=C(C=NC=C1)O.C(C=C)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>ClC1=C(C=NC=C1)OCC=C | O[CH2:3][CH:2]=[CH2:1].[OH:4][c:5]1[cH:6][n:7][cH:8][cH:9][c:10]1[Cl:11]>>[CH2:1]=[CH:2][CH2:3][O:4][c:5]1[cH:6][n:7][cH:8][cH:9][c:10]1[Cl:11] | C=CCO.Oc1cnccc1Cl | C=CCOc1cnccc1Cl | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccncc1 | O-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]:[#7;a:8]:[c:9]>>[C;D1;H2:3]=[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7]:[#7;a:8]:[c:9] | 32.6 | [{"value": 32.6, "product": "ClC1=C(C=NC=C1)OCC=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of diazenedicarboxylic acid diethyl ester (0.1572 mol) in THF (163 ml) was added dropwise to a mixture of 4-chloro-3-pyridinol (0.1429 mol), 2-propen-1-ol (0.1572 mol) and triphenyl-phosphine (0.1572 mol) in THF (276 ml), that was cooled with an ice-water bath and under nitrogen flow. The formed mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccncc1 | HO- | C1CCOC1 | null | null | C=CCO.Oc1cnccc1Cl>C1CCOC1>C=CCOc1cnccc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-94d8148633e341e8970b0d1286e9d02e | BrCC(Br)COc1cnccc1OCc1ccccc1>>BrCC1COc2cnccc2O1 | [NH4+].[Cl-].C(=O)([O-])C(O)C(O)C(=O)[O-].[Na+].[K+].BrC(COC=1C=NC=CC1OCC1=CC=CC=C1)CBr>>BrCC1OC2=C(C=NC=C2)OC1 | Br[CH:3]([CH2:2][Br:1])[CH2:4][O:5][c:6]1[cH:7][n:8][cH:9][cH:10][c:11]1[O:12]Cc1ccccc1>>[Br:1][CH2:2][CH:3]1[CH2:4][O:5][c:6]2[cH:7][n:8][cH:9][cH:10][c:11]2[O:12]1 | BrCC(Br)COc1cnccc1OCc1ccccc1 | BrCC1COc2cnccc2O1 | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 6a91d731e35d1f75b5cb1ee9b07680dfdeabd193bab631f6f8f7634763bc665e | 90564897fbe442dd5134de6abc48403858bfdbcd71e4ddc209af85b5258412e4 | c1cc2c(cn1)OCCO2 | Br-[CH;D3;+0:1](-[C:2]-[Br;D1;H0:3])-[C:4]-[#8:5]-[c:6]1:[c:7]:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[O;H0;D2;+0:12]-C-c1:c:c:c:c:c:1>>[Br;D1;H0:3]-[C:2]-[CH;D3;+0:1]1-[C:4]-[#8:5]-[c:6]2:[c:7]:[#7;a:8]:[c:9]:[c:10]:[c:11]:2-[O;H0;D2;+0:12]-1 | 13.6 | [{"value": 13.6, "product": "BrCC1OC2=C(C=NC=C2)OC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of intermediate (46) (0.0166 mol) in DCM (270 ml), FeCl3 (0.033 mol) was added portionwise and the mixture was stirred at room temperature overnight. The reaction mixture was treated with a saturated NH4Cl-solution and with a diluted solution of potassium sodium tartrate and then it was filtered off over ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ether | Ether | c1ccccc1 | c1cc2c(cn1)OCCO2 | c1cc2c(cn1)OCCO2 | HBr | C(Cl)Cl | null | 8 | BrCC(Br)COc1cnccc1OCc1ccccc1>C(Cl)Cl>BrCC1COc2cnccc2O1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-163dcc41d9d344648276574598d51bb8 | Brc1cncnc1.C=CCO>>C=CCOc1cncnc1 | BrC=1C=NC=NC1.C(C=C)O.[H-].[Na+]>>C(C=C)OC=1C=NC=NC1 | Br[c:5]1[cH:6][n:7][cH:8][n:9][cH:10]1.[CH2:1]=[CH:2][CH2:3][OH:4]>>[CH2:1]=[CH:2][CH2:3][O:4][c:5]1[cH:6][n:7][cH:8][n:9][cH:10]1 | Brc1cncnc1.C=CCO | C=CCOc1cncnc1 | null | null | O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a445000eb5ed501274d93689ad5b9d45095af02deca02b6b541c8a834890a276 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1cncnc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1.[C;D1;H2:7]=[C:8]-[C:9]-[OH;D1;+0:10]>>[C;D1;H2:7]=[C:8]-[C:9]-[O;H0;D2;+0:10]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1 | 26.8 | [{"value": 26.8, "product": "C(C=C)OC=1C=NC=NC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 5-Bromo-pyrimidine (0.063 mol) was slowly added to 2-propen-1-ol (4.03 mol) at 0° C. and this mixture was stirred at room temperature for 1 hour. Then NaH 60% (0.126 mol) was added and the reaction mixture was stirred and refluxed for 48 hours. Water was added and the mixture was extracted with ethyl acetate. The separ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cncnc1 | c1cncnc1 | c1cncnc1 | HBr | O | null | 1 | Brc1cncnc1.C=CCO>O>C=CCOc1cncnc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-40f74aa4c754468cb801ca900ccfeaa9 | O=c1[nH]cncc1OCC(Br)CBr>>BrCC1COc2cncnc2O1 | BrC(COC=1C(NC=NC1)=O)CBr.C(=O)(O)[O-].[Na+]>>BrCC1COC2=C(N=CN=C2)O1 | Br[CH:3]([CH2:2][Br:1])[CH2:4][O:5][c:6]1[cH:7][n:8][cH:9][nH:10][c:11]1=[O:12]>>[Br:1][CH2:2][CH:3]1[CH2:4][O:5][c:6]2[cH:7][n:8][cH:9][n:10][c:11]2[O:12]1 | O=c1[nH]cncc1OCC(Br)CBr | BrCC1COc2cncnc2O1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 2cf40f24d2b2806e3617773e4e35db40e12cd8a43ab5a32e7bc2002e284bce4a | 302f6042868059cd60da1fdb36403ed695deb6b9677d3cdc596dc8b229cbf806 | c1ncc2c(n1)OCCO2 | Br-[CH;D3;+0:1](-[C:2]-[Br;D1;H0:3])-[C:4]-[#8:5]-[c:6]1:[c:7]:[#7;a:8]:[c:9]:[nH;D2;+0:10]:[c;H0;D3;+0:11]:1=[O;H0;D1;+0:12]>>[Br;D1;H0:3]-[C:2]-[CH;D3;+0:1]1-[C:4]-[#8:5]-[c:6]2:[c:7]:[#7;a:8]:[c:9]:[n;H0;D2;+0:10]:[c;H0;D3;+0:11]:2-[O;H0;D2;+0:12]-1 | 52.3 | [{"value": 52.3, "product": "BrCC1COC2=C(N=CN=C2)O1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of intermediate (50) (0.0091 mol) and NaHCO3 (0.0113 mol) in ethanol (100 ml) was stirred and refluxed for 16 hours. The reaction mixture was allowed to cool to room temperature and the solvent was evaporated. The residue was taken up in water and ethyl acetate. The separated organic layer was dried, filtered... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide | Ether | c1cncnc1 | c1ncc2c(n1)OCCO2 | c1ncc2c(n1)OCCO2 | HBr | C(C)O | null | null | O=c1[nH]cncc1OCC(Br)CBr>C(C)O>BrCC1COc2cncnc2O1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b5cf7d59486349e89fab2b0620de818e | C=CC(=O)OCC.NCCCN(Cc1ccccc1)Cc1ccccc1>>CCOC(=O)CCNCCCN(Cc1ccccc1)Cc1ccccc1 | NCCCN(CC1=CC=CC=C1)CC1=CC=CC=C1.C(C=C)(=O)OCC>>C1(=CC=CC=C1)CN(CCCNCCC(=O)OCC)CC1=CC=CC=C1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[CH2:7].[NH2:8][CH2:9][CH2:10][CH2:11][N:12]([CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)[CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][NH:8][CH2:9][CH2:10][CH2:11][N:12]([CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19... | C=CC(=O)OCC.NCCCN(Cc1ccccc1)Cc1ccccc1 | CCOC(=O)CCNCCCN(Cc1ccccc1)Cc1ccccc1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | aza-Michael addition primary | 1a11d98577799a07170cd5efd9dd7bb03f34d533a77a248c8322bf305dad4248 | d462df48e06a3b2a50bc83cb7c56b836b8a054b4c300671faa54924b570d58bc | c1ccc(CNCc2ccccc2)cc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D2;+0:5]=[CH2;D1;+0:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[CH2;D2;+0:6]-[CH2;D2;+0:5]-[C:3](=[O;D1;H0:4])-[#8:2]-[C:1] | 39.1 | [{"value": 39.1, "product": "C1(=CC=CC=C1)CN(CCCNCCC(=O)OCC)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction under an argon flow. A mixture of 1-amino-3-dibenzylaminopropane (0.195 mol) in ethanol (225 ml) was stirred at room temperature. Ethyl propenoate (0.2 mol) was poured into the mixture and the reaction mixture was stirred overnight at room temperature. The solvent was evaporated. The residue was purified by co... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine.Vinyl | Ester.Secondary amine | null | null | c1ccccc1.c1ccccc1 | null | C(C)O | null | null | C=CC(=O)OCC.NCCCN(Cc1ccccc1)Cc1ccccc1>C(C)O>CCOC(=O)CCNCCCN(Cc1ccccc1)Cc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-00e861ed9a3041e892dd9e16a65da7fc | CCOC(=O)CCNCCCN(Cc1ccccc1)Cc1ccccc1>>O=C1CCN(CCCN(Cc2ccccc2)Cc2ccccc2)C(=O)N1 | Cl.O([K])C#N.O([K])C#N.Cl.CC(C)O.C1(=CC=CC=C1)CN(CCCNCCC(=O)OCC)CC1=CC=CC=C1>>C1(=CC=CC=C1)CN(CCCN1C(NC(CC1)=O)=O)CC1=CC=CC=C1 | CCO[C:2](=[O:1])[CH2:3][CH2:4][NH:5][CH2:6][CH2:7][CH2:8][N:9]([CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[O:1]=[C:2]1[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][N:9]([CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:2... | CCOC(=O)CCNCCCN(Cc1ccccc1)Cc1ccccc1 | O=C1CCN(CCCN(Cc2ccccc2)Cc2ccccc2)C(=O)N1 | null | O([K])C#N | O.CO.C(C)O | Miscellaneous | OtherReaction | 5313f292ded8b0c9c26323ff4af309b7e6ca577a3652c823683591f43f7bff01 | 431191b6e72cab06c234e878107510e04274523c51fab9db3aa00f4c030b4555 | O=C1CCN(CCCN(Cc2ccccc2)Cc2ccccc2)C(=O)N1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[NH;D2;+0:5]-[C:6]-[C:7]>>[C:7]-[C:6]-[N;H0;D3;+0:5]1-[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:8]-[C:9]-1=[O;D1;H0:10] | null | [] | null | null | 15 | MINUTE | Intermediate (52) was stirred in ethanol (150 ml). The mixture was acidified with HCl/2-propanol (±60 ml)+water (2 ml). The mixture was stirred for 15 minutes. The solvent was evaporated at 60° C. Ethanol was added to the residue. The solvent was evaporated. A mixture of methanol in water (70:30; 200 ml) was added to t... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | Urea.Unsubstituted dicarboximide | null | C1CNC[NH]C1 | C1CNC[NH]C1.c1ccccc1.c1ccccc1 | null | O([K])C#N.O.CO.C(C)O | null | 0.25 | CCOC(=O)CCNCCCN(Cc1ccccc1)Cc1ccccc1>O([K])C#N.O.CO.C(C)O>O=C1CCN(CCCN(Cc2ccccc2)Cc2ccccc2)C(=O)N1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c93706c944af46a08c77f879d28febb2 | O=C1CCN(CCCN(Cc2ccccc2)Cc2ccccc2)C(=O)N1>>NCCCN1CCC(=O)NC1=O | C1(=CC=CC=C1)CN(CCCN1C(NC(CC1)=O)=O)CC1=CC=CC=C1.[H][H]>>NCCCN1C(NC(CC1)=O)=O | c1ccc(C[N:1](Cc2ccccc2)[CH2:2][CH2:3][CH2:4][N:5]2[CH2:6][CH2:7][C:8](=[O:9])[NH:10][C:11]2=[O:12])cc1>>[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][C:8](=[O:9])[NH:10][C:11]1=[O:12] | O=C1CCN(CCCN(Cc2ccccc2)Cc2ccccc2)C(=O)N1 | NCCCN1CCC(=O)NC1=O | null | [Pd] | CO | Deprotection | OtherReaction | 2d0141567e42eb1f1e525678ba93b1f94e67edd4ce8af946d59aa7922040fcc6 | 09463156f8971f4e8007d84d8ed410eed1d618bdb6ba7dd05b4970ff2019f62b | O=C1CCNC(=O)N1 | [C:1]-[C:2]-[N;H0;D3;+0:3](-C-c1:c:c:c:c:c:1)-C-c1:c:c:c:c:c:1>>[C:1]-[C:2]-[NH2;D1;+0:3] | 90 | [{"value": 90.0, "product": "NCCCN1C(NC(CC1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of intermediate (53) (0.010 mol) in methanol (150 ml) was hydrogenated at 50° C. with palladium-on-carbon (10%, 1 g) as a catalyst. After uptake of hydrogen (2 equivalents), the catalyst was filtered off and the filtrate was evaporated. Toluene was added and azeotroped on the rotary evaporator. The residue wa... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Primary amine | c1ccccc1.c1ccccc1 | null | C1C[NH]CNC1 | Other | [Pd].CO | null | null | O=C1CCN(CCCN(Cc2ccccc2)Cc2ccccc2)C(=O)N1>[Pd].CO>NCCCN1CCC(=O)NC1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b9164710d6a9432fba83d9bfa12c024f | CC1(C)CNC(=O)N(CCCN)C1.CS(=O)(=O)OCC1Oc2cccnc2O1>>CC1(C)CNC(=O)N(CCCNCC2Oc3cccnc3O2)C1 | CS(=O)(=O)OCC1OC=2C(=NC=CC2)O1.NCCCN1C(NCC(C1)(C)C)=O>>O1C(OC2=NC=CC=C21)CNCCCN2C(NCC(C2)(C)C)=O | [CH3:1][C:2]1([CH3:3])[CH2:4][NH:5][C:6](=[O:7])[N:8]([CH2:9][CH2:10][CH2:11][NH2:12])[CH2:23]1.CS(=O)(=O)O[CH2:13][CH:14]1[O:15][c:16]2[cH:17][cH:18][cH:19][n:20][c:21]2[O:22]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][NH:5][C:6](=[O:7])[N:8]([CH2:9][CH2:10][CH2:11][NH:12][CH2:13][CH:14]2[O:15][c:16]3[cH:17][cH:18][cH:19][n:20][... | CC1(C)CNC(=O)N(CCCN)C1.CS(=O)(=O)OCC1Oc2cccnc2O1 | CC1(C)CNC(=O)N(CCCNCC2Oc3cccnc3O2)C1 | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | 8445343b2fb2fd8a9bc06f8532794f2ba6b99565a6e05a3bb9a4344ce2671186 | 7e6303acde8be57b43b4c6a673e1c7537b1efde90f08932e09e153dbba53a700 | O=C1NCCCN1CCCNCC1Oc2cccnc2O1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[c:4]:[c:5](:[#7;a:6])-[#8:7]-1.[C:8]-[C:9]-[NH2;D1;+0:10]>>[#7;a:6]:[c:5]1:[c:4]-[#8:3]-[C:2](-[CH2;D2;+0:1]-[NH;D2;+0:10]-[C:9]-[C:8])-[#8:7]-1 | 50.2 | [{"value": 50.2, "product": "O1C(OC2=NC=CC=C21)CNCCCN2C(NCC(C2)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 2 | HOUR | A mixture of intermediate (6) (0.0092 mol) and intermediate (13) (0.0183 mol) was stirred for 2 hours at 100° C. The crude reaction mixture was purified by open column chromatography over silica gel (eluent: CH2Cl2/CH3OH 90/10). The desired fractions were collected and the solvent was evaporated. The residue was washed... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Primary amine | Secondary amine | null | null | C1CNC[NH]C1.c1cnc2c(c1)OCO2 | MsOH.HO- | null | 100 | 2 | CC1(C)CNC(=O)N(CCCN)C1.CS(=O)(=O)OCC1Oc2cccnc2O1>>CC1(C)CNC(=O)N(CCCNCC2Oc3cccnc3O2)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-272890ddb56549ff8e10cff7c32a370c | O=C1CN(CC2CO2)C(=O)N1.c1ccc(CNCC2COc3cccnc3O2)cc1>>O=C1CN(CC(O)CN(Cc2ccccc2)CC2COc3cccnc3O2)C(=O)N1 | C1(=CC=CC=C1)CNCC1COC=2C(=NC=CC2)O1.O1C(C1)CN1C(NC(C1)=O)=O>>O1CC(OC2=NC=CC=C21)CN(CC(CN2C(NC(C2)=O)=O)O)CC2=CC=CC=C2 | [O:1]=[C:2]1[CH2:3][N:4]([CH2:5][CH:6]2[O:7][CH2:8]2)[C:28](=[O:29])[NH:30]1.[NH:9]([CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[CH2:17][CH:18]1[CH2:19][O:20][c:21]2[cH:22][cH:23][cH:24][n:25][c:26]2[O:27]1>>[O:1]=[C:2]1[CH2:3][N:4]([CH2:5][CH:6]([OH:7])[CH2:8][N:9]([CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c... | O=C1CN(CC2CO2)C(=O)N1.c1ccc(CNCC2COc3cccnc3O2)cc1 | O=C1CN(CC(O)CN(Cc2ccccc2)CC2COc3cccnc3O2)C(=O)N1 | null | null | CO | Heteroatom Alkylation and Arylation | Ring opening of epoxide with amine | 8b0e6adfb78f36f9ea38287644fe13d1ed2aa3ea65e10cc66a65b05c37e2e473 | 97e758d6c4c8255d25541eb6c6a6f62e7dc30829ea162ca3392731efabc98a65 | O=C1CN(CCCN(Cc2ccccc2)CC2COc3cccnc3O2)C(=O)N1 | [#8:1]-[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[c:6].[C:7]-[C:8]1-[CH2;D2;+0:9]-[O;H0;D2;+0:10]-1>>[#8:1]-[C:2]-[C:3]-[N;H0;D3;+0:4](-[C:5]-[c:6])-[CH2;D2;+0:9]-[C:8](-[C:7])-[OH;D1;+0:10] | 62.9 | [{"value": 62.9, "product": "O1CC(OC2=NC=CC=C21)CN(CC(CN2C(NC(C2)=O)=O)O)CC2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2,3-dihydro-N-(phenylmethyl)-1,4dioxino[2,3-b]pyridine-3-methanamine (0.0059 mol) and intermediate (18) (0.00497 mol) in methanol (30 ml) was stirred and refluxed overnight. The solvent was evaporated. The residue was purified by short open column chromatography over silica gel (eluent: CH2Cl212-propanone ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Secondary alcohol.Tertiary amine | C1CO1 | null | C1C[NH]CN1.c1ccccc1.c1cnc2c(c1)OCCO2 | null | CO | null | null | O=C1CN(CC2CO2)C(=O)N1.c1ccc(CNCC2COc3cccnc3O2)cc1>CO>O=C1CN(CC(O)CN(Cc2ccccc2)CC2COc3cccnc3O2)C(=O)N1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c60ac8e4ac2c4b1f93c294d3f5c814f1 | CS(=O)(=O)OC[C@@H]1COc2cccnc2O1.NCCCN1CCC(=O)NC1=O>>O=C1CCN(CCCNC[C@H]2COc3cccnc3O2)C(=O)N1 | NCCCN1C(NC(CC1)=O)=O.CS(=O)(=O)OC[C@@H]1COC=2C(=NC=CC2)O1>>O1C[C@@H](OC2=NC=CC=C21)CNCCCN2C(NC(CC2)=O)=O | CS(=O)(=O)O[CH2:10][C@@H:11]1[CH2:12][O:13][c:14]2[cH:15][cH:16][cH:17][n:18][c:19]2[O:20]1.[O:1]=[C:2]1[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][NH2:9])[C:21](=[O:22])[NH:23]1>>[O:1]=[C:2]1[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][NH:9][CH2:10][C@H:11]2[CH2:12][O:13][c:14]3[cH:15][cH:16][cH:17][n:18][c:19]3[O:20]2)[C:... | CS(=O)(=O)OC[C@@H]1COc2cccnc2O1.NCCCN1CCC(=O)NC1=O | O=C1CCN(CCCNC[C@H]2COc3cccnc3O2)C(=O)N1 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | Alkylation of amines | 8445343b2fb2fd8a9bc06f8532794f2ba6b99565a6e05a3bb9a4344ce2671186 | 7e6303acde8be57b43b4c6a673e1c7537b1efde90f08932e09e153dbba53a700 | O=C1CCN(CCCNC[C@H]2COc3cccnc3O2)C(=O)N1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2](-[#8:3]-[c:4]:[#7;a:5])-[C:6]-[#8:7].[C:8]-[C:9]-[NH2;D1;+0:10]>>[#7;a:5]:[c:4]-[#8:3]-[C:2](-[CH2;D2;+0:1]-[NH;D2;+0:10]-[C:9]-[C:8])-[C:6]-[#8:7] | 16.1 | [{"value": 16.1, "product": "O1C[C@@H](OC2=NC=CC=C21)CNCCCN2C(NC(CC2)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of intermediate (54) (0.058 mol) in dioxane (400 ml) was stirred. A mixture of intermediate (3) (0.029 mol) and CaO (2.4 g) was added. The reaction mixture was stirred at 140° C. for 16 hours. The solvent was evaporated. DCM and water was added to the residue. The separated organic layer was dried, filtered a... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Primary amine | Secondary amine | null | null | C1CNC[NH]C1.c1cnc2c(c1)OCCO2 | MsOH.HO- | O1CCOCC1 | null | null | CS(=O)(=O)OC[C@@H]1COc2cccnc2O1.NCCCN1CCC(=O)NC1=O>O1CCOCC1>O=C1CCN(CCCNC[C@H]2COc3cccnc3O2)C(=O)N1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5e097a300e7d4722996dea0fb55be713 | CS(=O)(=O)OC[C@@H]1COc2cccnc2O1.NCc1ccccc1>>c1ccc(CNC[C@H]2COc3cccnc3O2)cc1 | CS(=O)(=O)OC[C@@H]1COC=2C(=NC=CC2)O1.C(C1=CC=CC=C1)N.C(=O)(O)[O-].[Na+]>>C1(=CC=CC=C1)CNC[C@H]1COC=2C(=NC=CC2)O1 | CS(=O)(=O)O[CH2:7][C@@H:8]1[CH2:9][O:10][c:11]2[cH:12][cH:13][cH:14][n:15][c:16]2[O:17]1.[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH2:6])[cH:18][cH:19]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH:6][CH2:7][C@H:8]2[CH2:9][O:10][c:11]3[cH:12][cH:13][cH:14][n:15][c:16]3[O:17]2)[cH:18][cH:19]1 | CS(=O)(=O)OC[C@@H]1COc2cccnc2O1.NCc1ccccc1 | c1ccc(CNC[C@H]2COc3cccnc3O2)cc1 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | Alkylation of amines | 8445343b2fb2fd8a9bc06f8532794f2ba6b99565a6e05a3bb9a4344ce2671186 | 7e6303acde8be57b43b4c6a673e1c7537b1efde90f08932e09e153dbba53a700 | c1ccc(CNC[C@H]2COc3cccnc3O2)cc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2](-[#8:3]-[c:4]:[#7;a:5])-[C:6]-[#8:7].[NH2;D1;+0:8]-[C:9]-[c:10]>>[#7;a:5]:[c:4]-[#8:3]-[C:2](-[CH2;D2;+0:1]-[NH;D2;+0:8]-[C:9]-[c:10])-[C:6]-[#8:7] | null | [] | null | null | null | null | A mixture of intermediate (3) (0.041 mol), benzylamine (0.041 mol) and NaHCO3 (0.11 mol) in dioxane (100 ml) was stirred and refluxed for 48 hours. The solvent was evaporated. The residue was taken up in water and DCM. The separated organic layer was dried, filtered and the solvent was evaporated. The residue was purif... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Primary amine | Secondary amine | null | null | c1ccccc1.c1cnc2c(c1)OCCO2 | MsOH.HO- | O1CCOCC1 | null | null | CS(=O)(=O)OC[C@@H]1COc2cccnc2O1.NCc1ccccc1>O1CCOCC1>c1ccc(CNC[C@H]2COc3cccnc3O2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-38297af7c6ec49538e0643e0ab7da876 | C=CC#N.c1ccc(CNC[C@H]2COc3cccnc3O2)cc1>>N#CCCN(Cc1ccccc1)C[C@H]1COc2cccnc2O1 | C(C=C)#N.C1(=CC=CC=C1)CNC[C@H]1COC=2C(=NC=CC2)O1.C(C=C)#N.C(C=C)#N.C(C=C)#N>>O1C[C@@H](OC2=NC=CC=C21)CN(CCC#N)CC2=CC=CC=C2 | [N:1]#[C:2][CH:3]=[CH2:4].[NH:5]([CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[CH2:13][C@H:14]1[CH2:15][O:16][c:17]2[cH:18][cH:19][cH:20][n:21][c:22]2[O:23]1>>[N:1]#[C:2][CH2:3][CH2:4][N:5]([CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[CH2:13][C@H:14]1[CH2:15][O:16][c:17]2[cH:18][cH:19][cH:20][n:21][c:22]2[O:23]1 | C=CC#N.c1ccc(CNC[C@H]2COc3cccnc3O2)cc1 | N#CCCN(Cc1ccccc1)C[C@H]1COc2cccnc2O1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | aza-Michael addition secondary | 8acf647a588bdc7347506dcd3290904024f41acb450fe55eb6c0af193ad82ab8 | 828fcbb87adfef9f22c9a1e52b43c3df76cb2e49bfe62b57e8b79965772a2bed | c1ccc(CNC[C@H]2COc3cccnc3O2)cc1 | [#8:1]-[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[c:6].[CH2;D1;+0:7]=[CH;D2;+0:8]-[C:9]#[N;D1;H0:10]>>[#8:1]-[C:2]-[C:3]-[N;H0;D3;+0:4](-[C:5]-[c:6])-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[C:9]#[N;D1;H0:10] | 99.5 | [{"value": 99.5, "product": "O1C[C@@H](OC2=NC=CC=C21)CN(CCC#N)CC2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Intermediate (55) (0.0195 mol) was dissolved in ethanol (50 ml). 2-Propenenitrile (0.02 mol) was added and the reaction mixture was stirred and refluxed overnight. Additional 2-propenenitrile (0.02 mol) was added and the reaction mixture was stirred and refluxed for 2 hours. Additional 2-propenenitrile (0.02 mol) was a... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Vinyl | Tertiary amine | null | null | c1ccccc1.c1cnc2c(c1)OCCO2 | null | C(C)O | null | null | C=CC#N.c1ccc(CNC[C@H]2COc3cccnc3O2)cc1>C(C)O>N#CCCN(Cc1ccccc1)C[C@H]1COc2cccnc2O1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-75ed49acc2784c3493ed5ba4a7dabfe7 | CCOCC.Nc1ccc(Br)cc1C(=O)O>>CC(C)(O)c1cc(Br)ccc1N | Cl.NC1=C(C(=O)O)C=C(C=C1)Br.C[Mg]Br.CCOCC.[OH-].[Na+]>>NC1=C(C=C(C=C1)Br)C(C)(C)O | CCOC[CH3:3].O=[C:2]([OH:4])[c:5]1[cH:6][c:7]([Br:8])[cH:9][cH:10][c:11]1[NH2:12]>>[CH3:1][C:2]([CH3:3])([OH:4])[c:5]1[cH:6][c:7]([Br:8])[cH:9][cH:10][c:11]1[NH2:12] | CCOCC.Nc1ccc(Br)cc1C(=O)O | CC(C)(O)c1cc(Br)ccc1N | null | null | C(C)(=O)OCC.C1CCOC1 | C-C Coupling | OtherReaction | 8fffede311ab6e976b2c87246cb985fbcf7b3efb2fae50d4a939c6943cabc726 | 4fb8cd12751de39cc525c444cef492bee5116e308d33a4cbda36c3aed28708a2 | c1ccccc1 | C-C-O-C-[CH3;D1;+0:1].O=[C;H0;D3;+0:2](-[O;D1;H1:3])-[c:4](:[c:5]):[c:6]>>[C;D1;H3:7]-[C;H0;D4;+0:2](-[CH3;D1;+0:1])(-[O;D1;H1:3])-[c:4](:[c:5]):[c:6] | 57 | [{"value": 57.0, "product": "NC1=C(C=C(C=C1)Br)C(C)(C)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | A solution of 2-amino-5-bromobenzoic acid (10 g, 46 mmol) in dry THF (200 mL) was treated at −78° C. under nitrogen with a solution of methylmagnesium bromide in ether (3.0 M, 90 mL, 270 mmol). The reaction mixture was slowly warmed to ambient temperature, kept stirring for 48 hours under nitrogen and then poured into ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether | Tertiary alcohol | null | null | c1ccccc1 | HO- | C(C)(=O)OCC.C1CCOC1 | null | 48 | CCOCC.Nc1ccc(Br)cc1C(=O)O>C(C)(=O)OCC.C1CCOC1>CC(C)(O)c1cc(Br)ccc1N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1bdb0c9c30984b148cab296c799186b4 | CC(C)(O)c1cc(Br)ccc1N.O=C(n1ccnc1)n1ccnc1>>CC1(C)OC(=O)Nc2ccc(Br)cc21 | NC1=C(C=C(C=C1)Br)C(C)(C)O.C(=O)(N1C=NC=C1)N1C=NC=C1>>BrC1=CC2=C(NC(OC2(C)C)=O)C=C1 | [CH3:1][C:2]([CH3:3])([OH:4])[c:14]1[c:8]([NH2:7])[cH:9][cH:10][c:11]([Br:12])[cH:13]1.c1cn([C:5](n2ccnc2)=[O:6])cn1>>[CH3:1][C:2]1([CH3:3])[O:4][C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11]([Br:12])[cH:13][c:14]21 | CC(C)(O)c1cc(Br)ccc1N.O=C(n1ccnc1)n1ccnc1 | CC1(C)OC(=O)Nc2ccc(Br)cc21 | null | null | C1CCOC1 | Protection | OtherReaction | 862364157177f41c9bd3cedddf1e8ac68669ae6aef579bc9f5124c2f2002b152 | 37a2f72522e1c6135c1e724ca4e9730fb0d5786b25469510c29abe3444ce965b | O=C1Nc2ccccc2CO1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[OH;D1;+0:4])-[c:5]:[c:6](-[NH2;D1;+0:7]):[c:8].[O;D1;H0:9]=[C;H0;D3;+0:10](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[C;D1;H3:1]-[C:2]1(-[C;D1;H3:3])-[O;H0;D2;+0:4]-[C;H0;D3;+0:10](=[O;D1;H0:9])-[NH;D2;+0:7]-[c:6](:[c:8]):[c:5]-1 | 100 | [{"value": 100.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | To a solution of 2-(2-amino-5-bromophenyl)propan-2-ol (18 g, 78 mmol) in dry THF (150 mL) was added 1,1′-carbonyldiimidazole (15.5 g, 94 mmol) under nitrogen. The reaction solution was heated at 50° C. overnight. The solvent was removed in vacuo and the residue was dissolved in ethyl acetate (100 mL). The solution was ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol.Primary amine | Carbamic ester | c1c[nH]cn1.c1c[nH]cn1 | c1ccc2c(c1)COCN2 | c1ccc2c(c1)COCN2 | Other | C1CCOC1 | 50 | null | CC(C)(O)c1cc(Br)ccc1N.O=C(n1ccnc1)n1ccnc1>C1CCOC1>CC1(C)OC(=O)Nc2ccc(Br)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dce1481c01604b6eb9f28444a07ed038 | CC(C)OB(OC(C)C)OC(C)C.CC1(C)OC(=O)Nc2ccc(Br)cc21>>CC1(C)OC(=O)Nc2ccc(B(O)O)cc21 | B(OC(C)C)(OC(C)C)OC(C)C.BrC1=CC2=C(NC(OC2(C)C)=O)C=C1.[Li]CCCC.CCCCCC>>CC1(OC(NC2=C1C=C(C=C2)B(O)O)=O)C | CC(C)O[B:12]([O:13]C(C)C)[O:14]C(C)C.Br[c:11]1[cH:10][cH:9][c:8]2[c:16]([cH:15]1)[C:2]([CH3:1])([CH3:3])[O:4][C:5](=[O:6])[NH:7]2>>[CH3:1][C:2]1([CH3:3])[O:4][C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11]([B:12]([OH:13])[OH:14])[cH:15][c:16]21 | CC(C)OB(OC(C)C)OC(C)C.CC1(C)OC(=O)Nc2ccc(Br)cc21 | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21 | null | null | C1CCOC1 | Miscellaneous | Preparation of boronic acids | 2b0a2085eefa9fa3bf4ba7b9aabc03f175f26d8afa15449be7fcd2d2bb691b2a | dafd25fbe01879c365f8c874026e570f49824f4bb82016b29d0c5d21aeb58ca3 | O=C1Nc2ccccc2CO1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-C(-C)-O-[B;H0;D3;+0:6](-[O;H0;D2;+0:7]-C(-C)-C)-[O;H0;D2;+0:8]-C(-C)-C>>[OH;D1;+0:7]-[B;H0;D3;+0:6](-[OH;D1;+0:8])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 81.2 | [{"value": 81.0, "product": "CC1(OC(NC2=C1C=C(C=C2)B(O)O)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.2, "product": "CC1(OC(NC2=C1C=C(C=C2)B(O)O)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 30 | MINUTE | To a solution of 6-bromo-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one (2 g, 7.8 mmol) in anhydrous THF (60 mL) was added a solution of n-BuLi in hexane (10 M, 2.4 mL, 24 mmol) at −78° C. under nitrogen. After stirring at −78° C. for 30 minutes, a slurry was obtained and treated with triisopropyl borate (6.5 mL, 2... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Boronic acid | c1ccc2c(c1)COCN2 | c1ccc2c(c1)COCN2 | c1ccc2c(c1)COCN2 | HBr | C1CCOC1 | -78 | 0.5 | CC(C)OB(OC(C)C)OC(C)C.CC1(C)OC(=O)Nc2ccc(Br)cc21>C1CCOC1>CC1(C)OC(=O)Nc2ccc(B(O)O)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c56b7eebb6a041479df5e59be7a069dc | CC1(C)OC(=O)Nc2ccc(Br)cc21.OB(O)c1cccc(Cl)c1>>CC1(C)OC(=O)Nc2ccc(-c3cccc(Cl)c3)cc21 | BrC1=CC2=C(NC(OC2(C)C)=O)C=C1.ClC=1C=C(C=CC1)B(O)O.C([O-])([O-])=O.[Na+].[Na+]>>ClC=1C=C(C=CC1)C1=CC2=C(NC(OC2(C)C)=O)C=C1 | Br[c:11]1[cH:10][cH:9][c:8]2[c:20]([cH:19]1)[C:2]([CH3:1])([CH3:3])[O:4][C:5](=[O:6])[NH:7]2.OB(O)[c:12]1[cH:13][cH:14][cH:15][c:16]([Cl:17])[cH:18]1>>[CH3:1][C:2]1([CH3:3])[O:4][C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][c:16]([Cl:17])[cH:18]3)[cH:19][c:20]21 | CC1(C)OC(=O)Nc2ccc(Br)cc21.OB(O)c1cccc(Cl)c1 | CC1(C)OC(=O)Nc2ccc(-c3cccc(Cl)c3)cc21 | null | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | O.COCCOC | C-C Coupling | Suzuki coupling with boronic acids | 0fa2a30709dcd56081dfd73304ec3a2ee5346cb80b80e4b5dc426c319dd3d4bb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Nc2ccc(-c3ccccc3)cc2CO1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9]:[c:10] | 82.5 | [{"value": 82.0, "product": "ClC=1C=C(C=CC1)C1=CC2=C(NC(OC2(C)C)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.5, "product": "ClC=1C=C(C=CC1)C1=CC2=C(NC(OC2(C)C)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | null | null | A mixture of 6-bromo-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one (1.5 g, 5.9 mmol), 3-chlorophenyl boronic acid (1.83 g, 11.7 mmol), tetrakis(triphenylphosphine)-palladium (0) (0.35 g, 0.3 mmol), and sodium carbonate (2.48 g, 23.4 mmol) in a mixture of DME and water (40 mL/10 mL) was degassed to remove the oxyge... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)COCN2.c1ccccc1 | c1ccc2c(c1)COCN2.c1ccccc1 | c1ccc2c(c1)COCN2.c1ccccc1 | HBr.B | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.O.COCCOC | 85 | null | CC1(C)OC(=O)Nc2ccc(Br)cc21.OB(O)c1cccc(Cl)c1>[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.O.COCCOC>CC1(C)OC(=O)Nc2ccc(-c3cccc(Cl)c3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e4aeb5dbae2c48daa29afde8631fb69a | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.Fc1cc(Br)cc(Br)c1>>CC1(C)OC(=O)Nc2ccc(-c3cc(F)cc(Br)c3)cc21 | CC1(OC(NC2=C1C=C(C=C2)B(O)O)=O)C.BrC1=CC(=CC(=C1)F)Br.C([O-])([O-])=O.[Na+].[Na+]>>BrC=1C=C(C=C(C1)F)C1=CC2=C(NC(OC2(C)C)=O)C=C1 | OB(O)[c:11]1[cH:10][cH:9][c:8]2[c:21]([cH:20]1)[C:2]([CH3:1])([CH3:3])[O:4][C:5](=[O:6])[NH:7]2.Br[c:12]1[cH:13][c:14]([F:15])[cH:16][c:17]([Br:18])[cH:19]1>>[CH3:1][C:2]1([CH3:3])[O:4][C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][c:14]([F:15])[cH:16][c:17]([Br:18])[cH:19]3)[cH:20][c:21]21 | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.Fc1cc(Br)cc(Br)c1 | CC1(C)OC(=O)Nc2ccc(-c3cc(F)cc(Br)c3)cc21 | 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 | O.COCCOC | C-C Coupling | Suzuki coupling with boronic acids | 0fa2a30709dcd56081dfd73304ec3a2ee5346cb80b80e4b5dc426c319dd3d4bb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Nc2ccc(-c3ccccc3)cc2CO1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 40 | [{"value": 40.0, "product": "BrC=1C=C(C=C(C1)F)C1=CC2=C(NC(OC2(C)C)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.0, "product": "BrC=1C=C(C=C(C1)F)C1=CC2=C(NC(OC2(C)C)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | null | null | A mixture of (1,4-dihydro-4,4-dimethyl-2-oxo-2H-3,1-benzoxazin-6-yl)boronic acid (2.22 g, 10 mmol), 1,3-dibromo-5-fluorobenzene (3.05 g, 12 mmol), tetrakis(triphenylphosphine)palladium (0) (0.6 g, 0.52 mmol), and sodium carbonate (2.2 g, 21 mmol) in a mixture of DME and water (70 mL/15 mL) was degassed to remove the ox... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)COCN2.c1ccccc1 | c1ccc2c(c1)COCN2.c1ccccc1 | c1ccc2c(c1)COCN2.c1ccccc1 | HBr.B | 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.O.COCCOC | 85 | null | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.Fc1cc(Br)cc(Br)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.O.COCCOC>CC1(C)OC(=O)Nc2ccc(-c3cc(F)cc(Br)c3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c605e453a603463e80be6c8434fee87e | CC1(C)OC(=O)Nc2ccc(-c3cc(F)cc(Br)c3)cc21>>CC1(C)OC(=O)Nc2ccc(-c3cc(F)cc(C#N)c3)cc21 | BrC=1C=C(C=C(C1)F)C1=CC2=C(NC(OC2(C)C)=O)C=C1.CN(C)C=O>>CC1(C2=C(NC(O1)=O)C=CC(=C2)C=2C=C(C#N)C=C(C2)F)C | Br[c:17]1[cH:16][c:14]([F:15])[cH:13][c:12](-[c:11]2[cH:10][cH:9][c:8]3[c:22]([cH:21]2)[C:2]([CH3:1])([CH3:3])[O:4][C:5](=[O:6])[NH:7]3)[cH:20]1>>[CH3:1][C:2]1([CH3:3])[O:4][C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][c:14]([F:15])[cH:16][c:17]([C:18]#[N:19])[cH:20]3)[cH:21][c:22]21 | CC1(C)OC(=O)Nc2ccc(-c3cc(F)cc(Br)c3)cc21 | CC1(C)OC(=O)Nc2ccc(-c3cc(F)cc(C#N)c3)cc21 | null | [Zn].[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | null | Miscellaneous | OtherReaction | 3ae4da8b7f110de99cf8afc091b6f0c8540050148e425770f8030bce1480042c | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | O=C1Nc2ccc(-c3ccccc3)cc2CO1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]>>[N;D1;H0:6]#[C:7]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 84 | [{"value": 84.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | null | null | A mixture of 6-(3-bromo-5-fluorophenyl)-4,4-dimethyl-2H-benz[d][1,3]oxazin-2-one (1 g, 2.8 mmol), zinc cyamide (0.2 g, 1.7 mmol), and tetrakis(triphenylphosphine)-palladium (0) (0.2 g, 0.17 mmol) in dry DMF (20 mL) was degassed to remove oxygen and was then heated at 85° C. under a blanket of nitrogen for 6.5 hours. Th... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccccc1 | c1ccccc1 | c1ccc2c(c1)COCN2.c1ccccc1 | Br- | [Zn].[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | 85 | null | CC1(C)OC(=O)Nc2ccc(-c3cc(F)cc(Br)c3)cc21>[Zn].[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>CC1(C)OC(=O)Nc2ccc(-c3cc(F)cc(C#N)c3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-13dc986b879a4a4e809552b5902f8974 | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.N#Cc1cc(Br)cs1>>CC1(C)OC(=O)Nc2ccc(-c3csc(C#N)c3)cc21 | CC1(OC(NC2=C1C=C(C=C2)B(O)O)=O)C.BrC=1C=C(SC1)C#N>>CC1(C2=C(NC(O1)=O)C=CC(=C2)C=2C=C(SC2)C#N)C | OB(O)[c:11]1[cH:10][cH:9][c:8]2[c:20]([cH:19]1)[C:2]([CH3:1])([CH3:3])[O:4][C:5](=[O:6])[NH:7]2.Br[c:12]1[cH:13][s:14][c:15]([C:16]#[N:17])[cH:18]1>>[CH3:1][C:2]1([CH3:3])[O:4][C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][s:14][c:15]([C:16]#[N:17])[cH:18]3)[cH:19][c:20]21 | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.N#Cc1cc(Br)cs1 | CC1(C)OC(=O)Nc2ccc(-c3csc(C#N)c3)cc21 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 0b5bebfae8e49ed7172cda779db0d9a1ee34897b702e6169adb1825468a1d911 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Nc2ccc(-c3ccsc3)cc2CO1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#16;a:3]:[c:4](-[C:5]#[N;D1;H0:6]):[c:7]:1.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[N;D1;H0:6]#[C:5]-[c:4]1:[#16;a:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:7]:1 | null | [] | null | null | null | null | The product was prepared, from (1,4-dihydro-4,4-dimethyl-2-oxo-2H-3,1-benzoxazin-6-yl)boronic acid and 4-bromo-2-thiophenecarbonitrile according to the procedure outlined in Example 5, as a yellowish solid: mp 230–231° C. (decomposed); 1H-NMR (CDCl3) δ 8.32 (s, 1H, D2O exchangeable), 7.83 (d, 1H, J=1.5 Hz), 7.61 (d, 1H... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)COCN2.c1ccsc1 | c1ccc2c(c1)COCN2.c1ccsc1 | c1ccc2c(c1)COCN2.c1ccsc1 | HBr.B | null | null | null | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.N#Cc1cc(Br)cs1>>CC1(C)OC(=O)Nc2ccc(-c3csc(C#N)c3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a23622732e894873b8b5a7d3d74e9251 | CC1(C)OC(=O)Nc2ccc(-c3cccc(Cl)c3)cc21.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1>>CC1(C)OC(=S)Nc2ccc(-c3cccc(Cl)c3)cc21 | ClC=1C=C(C=CC1)C1=CC2=C(NC(OC2(C)C)=O)C=C1.COC=1C=CC(=CC1)P2(=S)SP(=S)(S2)C=3C=CC(=CC3)OC>>ClC=1C=C(C=CC1)C1=CC2=C(NC(OC2(C)C)=S)C=C1 | O=[C:5]1[O:4][C:2]([CH3:1])([CH3:3])[c:20]2[c:8]([cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][c:16]([Cl:17])[cH:18]3)[cH:19]2)[NH:7]1.COc1ccc(P2(=S)SP(c3ccc(OC)cc3)(=[S:6])S2)cc1>>[CH3:1][C:2]1([CH3:3])[O:4][C:5](=[S:6])[NH:7][c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][c:16]([Cl:17])[cH:18]3)[cH:19][c:... | CC1(C)OC(=O)Nc2ccc(-c3cccc(Cl)c3)cc21.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1 | CC1(C)OC(=S)Nc2ccc(-c3cccc(Cl)c3)cc21 | null | null | CC=1C=CC=CC1C | Heteroatom Alkylation and Arylation | OtherReaction | 97d5668e697b90041eba9dad68ad83f7a1cdfe0944b559f928d28ab2564e8d10 | c331ef400a59f343eb23abd2f965cf1719390c2753d5de53af30054e75d29d94 | S=C1Nc2ccc(-c3ccccc3)cc2CO1 | C-O-c1:c:c:c(-P2(=S)-S-P(=[S;H0;D1;+0:1])(-c3:c:c:c(-O-C):c:c:3)-S-2):c:c:1.O=[C;H0;D3;+0:2](-[#7:3]-[c:4])-[#8:5]-[C:6]>>[C:6]-[#8:5]-[C;H0;D3;+0:2](=[S;H0;D1;+0:1])-[#7:3]-[c:4] | 52.7 | [{"value": 52.0, "product": "ClC=1C=C(C=CC1)C1=CC2=C(NC(OC2(C)C)=S)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.7, "product": "ClC=1C=C(C=CC1)C1=CC2=C(NC(OC2(C)C)=S)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 6-(3-chlorophenyl)-4,4-dimethyl-1,4-dihydro-benzo[d]-[1,3]oxazin-2-one (0.15 g, 0.5 mmol) and Lawesson's reagent (0.24 g, 0.6 mmol) in anhydrous o-xylene was heated at reflux under nitrogen for 3 hours. The solvent was removed and the residue was purified by a flash chromatography (silica gel, hexane:ethyl... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether.Ether.Monosulfide.Monosulfide | Ether.Thioamide | c1ccc2c(c1)COCN2.c1ccccc1.P1SPS1.c1ccccc1 | c1ccc2c(c1)COCN2 | c1ccc2c(c1)COCN2.c1ccccc1 | Other | CC=1C=CC=CC1C | null | null | CC1(C)OC(=O)Nc2ccc(-c3cccc(Cl)c3)cc21.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1>CC=1C=CC=CC1C>CC1(C)OC(=S)Nc2ccc(-c3cccc(Cl)c3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-56c70a52190b4d3eaec1cc918d735fd3 | CC1(C)OC(=O)Nc2ccc(Br)cc21.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1>>CC1(C)OC(=S)Nc2ccc(Br)cc21 | BrC1=CC2=C(NC(OC2(C)C)=O)C=C1.COC=1C=CC(=CC1)P2(=S)SP(=S)(S2)C=3C=CC(=CC3)OC>>BrC1=CC2=C(NC(OC2(C)C)=S)C=C1 | O=[C:5]1[O:4][C:2]([CH3:1])([CH3:3])[c:14]2[c:8]([cH:9][cH:10][c:11]([Br:12])[cH:13]2)[NH:7]1.COc1ccc(P2(=S)SP(c3ccc(OC)cc3)(=[S:6])S2)cc1>>[CH3:1][C:2]1([CH3:3])[O:4][C:5](=[S:6])[NH:7][c:8]2[cH:9][cH:10][c:11]([Br:12])[cH:13][c:14]21 | CC1(C)OC(=O)Nc2ccc(Br)cc21.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1 | CC1(C)OC(=S)Nc2ccc(Br)cc21 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 97d5668e697b90041eba9dad68ad83f7a1cdfe0944b559f928d28ab2564e8d10 | c331ef400a59f343eb23abd2f965cf1719390c2753d5de53af30054e75d29d94 | S=C1Nc2ccccc2CO1 | C-O-c1:c:c:c(-P2(=S)-S-P(=[S;H0;D1;+0:1])(-c3:c:c:c(-O-C):c:c:3)-S-2):c:c:1.O=[C;H0;D3;+0:2](-[#7:3]-[c:4])-[#8:5]-[C:6]>>[C:6]-[#8:5]-[C;H0;D3;+0:2](=[S;H0;D1;+0:1])-[#7:3]-[c:4] | null | [] | null | null | null | null | The product was prepared, from 6-bromo-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one and Lawesson's reagent using the procedure of Example 9, as a white solid: mp 221–222.5° C.; 1H-NMR (CDCl3) δ 9.38 (s, 1H, D2O exchangeable), 7.42 (dd, 1H, J=8.5, 2.1 Hz), 7.29 (d, 1H, J=2.0 Hz), 6.76 (d, 1H, J=8.4 Hz), 1.76 (s, 6... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether.Ether.Monosulfide.Monosulfide | Ether.Thioamide | c1ccc2c(c1)COCN2.c1ccccc1.P1SPS1.c1ccccc1 | c1ccc2c(c1)COCN2 | c1ccc2c(c1)COCN2 | Other | null | null | null | CC1(C)OC(=O)Nc2ccc(Br)cc21.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1>>CC1(C)OC(=S)Nc2ccc(Br)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-78d414029c0d443d943cdb207a4e71ef | CC1(C)OC(=O)Nc2ccc(-c3cc(F)cc(C#N)c3)cc21.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1>>CC1(C)OC(=S)Nc2ccc(-c3cc(F)cc(C#N)c3)cc21 | CC1(C2=C(NC(O1)=O)C=CC(=C2)C=2C=C(C#N)C=C(C2)F)C.COC=1C=CC(=CC1)P2(=S)SP(=S)(S2)C=3C=CC(=CC3)OC>>CC1(C2=C(NC(O1)=S)C=CC(=C2)C=2C=C(C#N)C=C(C2)F)C | O=[C:5]1[O:4][C:2]([CH3:1])([CH3:3])[c:22]2[c:8]([cH:9][cH:10][c:11](-[c:12]3[cH:13][c:14]([F:15])[cH:16][c:17]([C:18]#[N:19])[cH:20]3)[cH:21]2)[NH:7]1.COc1ccc(P2(=S)SP(c3ccc(OC)cc3)(=[S:6])S2)cc1>>[CH3:1][C:2]1([CH3:3])[O:4][C:5](=[S:6])[NH:7][c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][c:14]([F:15])[cH:16][c:17]([C:18]#... | CC1(C)OC(=O)Nc2ccc(-c3cc(F)cc(C#N)c3)cc21.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1 | CC1(C)OC(=S)Nc2ccc(-c3cc(F)cc(C#N)c3)cc21 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 97d5668e697b90041eba9dad68ad83f7a1cdfe0944b559f928d28ab2564e8d10 | c331ef400a59f343eb23abd2f965cf1719390c2753d5de53af30054e75d29d94 | S=C1Nc2ccc(-c3ccccc3)cc2CO1 | C-O-c1:c:c:c(-P2(=S)-S-P(=[S;H0;D1;+0:1])(-c3:c:c:c(-O-C):c:c:3)-S-2):c:c:1.O=[C;H0;D3;+0:2](-[#7:3]-[c:4])-[#8:5]-[C:6]>>[C:6]-[#8:5]-[C;H0;D3;+0:2](=[S;H0;D1;+0:1])-[#7:3]-[c:4] | null | [] | null | null | null | null | The product was prepared, from 3-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)-5-fluorobenzonitrile and Lawesson's reagent using the procedure of Example 9, as a yellow solid: 248–249° C.; 1H-NMR (DMSO-d6) δ 12.3 (s, 1H), 8.15 (bs, 1H), 8.02 (d, 1H, J=10.48 Hz), 7.85–7.78 (m, 3H), 7.13 (d, 1H, J=8.92 Hz)... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether.Ether.Monosulfide.Monosulfide | Ether.Thioamide | c1ccc2c(c1)COCN2.c1ccccc1.P1SPS1.c1ccccc1 | c1ccc2c(c1)COCN2 | c1ccc2c(c1)COCN2.c1ccccc1 | Other | null | null | null | CC1(C)OC(=O)Nc2ccc(-c3cc(F)cc(C#N)c3)cc21.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1>>CC1(C)OC(=S)Nc2ccc(-c3cc(F)cc(C#N)c3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c74b12003cc8454a8608e851478103ea | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.N#Cc1cccc(Br)c1>>CC1(C)OC(=O)Nc2ccc(-c3cccc(C#N)c3)cc21 | CC1(OC(NC2=C1C=C(C=C2)B(O)O)=O)C.BrC=1C=C(C#N)C=CC1.C([O-])([O-])=O.[Na+].[Na+]>>CC1(C2=C(NC(O1)=O)C=CC(=C2)C=2C=C(C#N)C=CC2)C | OB(O)[c:11]1[cH:10][cH:9][c:8]2[c:21]([cH:20]1)[C:2]([CH3:1])([CH3:3])[O:4][C:5](=[O:6])[NH:7]2.Br[c:12]1[cH:13][cH:14][cH:15][c:16]([C:17]#[N:18])[cH:19]1>>[CH3:1][C:2]1([CH3:3])[O:4][C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][c:16]([C:17]#[N:18])[cH:19]3)[cH:20][c:21]21 | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.N#Cc1cccc(Br)c1 | CC1(C)OC(=O)Nc2ccc(-c3cccc(C#N)c3)cc21 | 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 | O.COCCOC | C-C Coupling | Suzuki coupling with boronic acids | 0fa2a30709dcd56081dfd73304ec3a2ee5346cb80b80e4b5dc426c319dd3d4bb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Nc2ccc(-c3ccccc3)cc2CO1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 25.2 | [{"value": 25.0, "product": "CC1(C2=C(NC(O1)=O)C=CC(=C2)C=2C=C(C#N)C=CC2)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 25.2, "product": "CC1(C2=C(NC(O1)=O)C=CC(=C2)C=2C=C(C#N)C=CC2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | null | null | A mixture of (1,4-dihydro-4,4-dimethyl-2-oxo-2H-3,1-benzoxazin-6-yl)boronic acid (2.22 g, 10 mmol), 3-bromobenzonitrile (2.18 g, 12 mmol), tetrakis(triphenylphosphine)palladium (0) (0.6 g, 0.52 mmol), and sodium carbonate (2.2 g, 21 mmol) in a mixture of DME and water (70 mL/15 mL) was degassed to remove the oxygen and... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)COCN2.c1ccccc1 | c1ccc2c(c1)COCN2.c1ccccc1 | c1ccc2c(c1)COCN2.c1ccccc1 | HBr.B | 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.O.COCCOC | 85 | null | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.N#Cc1cccc(Br)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.O.COCCOC>CC1(C)OC(=O)Nc2ccc(-c3cccc(C#N)c3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d14ffcd17bd24b77be53296b3e5dd34b | CC1(C)OC(=O)Nc2ccc(-c3cccc(C#N)c3)cc21.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1>>CC1(C)OC(=S)Nc2ccc(-c3cccc(C#N)c3)cc21 | CC1(C2=C(NC(O1)=O)C=CC(=C2)C=2C=C(C#N)C=CC2)C.COC=1C=CC(=CC1)P2(=S)SP(=S)(S2)C=3C=CC(=CC3)OC.C(C)(=O)OCC>>CC1(C2=C(NC(O1)=S)C=CC(=C2)C=2C=C(C#N)C=CC2)C | O=[C:5]1[O:4][C:2]([CH3:1])([CH3:3])[c:21]2[c:8]([cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][c:16]([C:17]#[N:18])[cH:19]3)[cH:20]2)[NH:7]1.COc1ccc(P2(=S)SP(c3ccc(OC)cc3)(=[S:6])S2)cc1>>[CH3:1][C:2]1([CH3:3])[O:4][C:5](=[S:6])[NH:7][c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][c:16]([C:17]#[N:18])[cH:19]... | CC1(C)OC(=O)Nc2ccc(-c3cccc(C#N)c3)cc21.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1 | CC1(C)OC(=S)Nc2ccc(-c3cccc(C#N)c3)cc21 | null | null | CC=1C=CC=CC1C | Heteroatom Alkylation and Arylation | OtherReaction | 97d5668e697b90041eba9dad68ad83f7a1cdfe0944b559f928d28ab2564e8d10 | c331ef400a59f343eb23abd2f965cf1719390c2753d5de53af30054e75d29d94 | S=C1Nc2ccc(-c3ccccc3)cc2CO1 | C-O-c1:c:c:c(-P2(=S)-S-P(=[S;H0;D1;+0:1])(-c3:c:c:c(-O-C):c:c:3)-S-2):c:c:1.O=[C;H0;D3;+0:2](-[#7:3]-[c:4])-[#8:5]-[C:6]>>[C:6]-[#8:5]-[C;H0;D3;+0:2](=[S;H0;D1;+0:1])-[#7:3]-[c:4] | 20 | [{"value": 20.0, "product": "CC1(C2=C(NC(O1)=S)C=CC(=C2)C=2C=C(C#N)C=CC2)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 19.8, "product": "CC1(C2=C(NC(O1)=S)C=CC(=C2)C=2C=C(C#N)C=CC2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-benzo [d][1,3]oxazin-6-yl)-benzonitrile (1 g, 3.6 mmol) and Lawesson's reagent (1.8 g, 4.3 mmol) in o-xylene (30 mL) was heated at reflux overnight. The reaction mixture was cooled to room temperature, poured into ethyl acetate (50 mL) and washed with 1 N HCl (2×20 mL).... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether.Ether.Monosulfide.Monosulfide | Ether.Thioamide | c1ccc2c(c1)COCN2.c1ccccc1.P1SPS1.c1ccccc1 | c1ccc2c(c1)COCN2 | c1ccc2c(c1)COCN2.c1ccccc1 | Other | CC=1C=CC=CC1C | null | null | CC1(C)OC(=O)Nc2ccc(-c3cccc(C#N)c3)cc21.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1>CC=1C=CC=CC1C>CC1(C)OC(=S)Nc2ccc(-c3cccc(C#N)c3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fc3c3df4c19f4d1182851641d7f90a04 | N#Cc1cc(-c2cccc(F)c2)ccc1N.N#Cc1cc(Br)ccc1N.OB(O)c1cccc(F)c1>>CC(=O)c1cc(-c2cccc(F)c2)ccc1N.N#Cc1cc(-c2cccc(F)c2)ccc1N | FC=1C=C(C=CC1)B(O)O.NC1=C(C#N)C=C(C=C1)Br.Cl.NC1=C(C=C(C=C1)C1=CC(=CC=C1)F)C#N.C[Mg]Br.C([O-])([O-])=O.[Na+].[Na+]>>NC1=C(C=C(C=C1)C1=CC(=CC=C1)F)C#N.NC1=C(C=C(C=C1)C1=CC(=CC=C1)F)C(C)=O | N#[C:2][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][c:11]([F:12])[cH:13]2)[cH:14][cH:15][c:16]1[NH2:17].Br[c:22]1[cH:21][c:20]([C:19]#[N:18])[c:32]([NH2:33])[cH:31][cH:30]1.OB([OH:3])[c:23]1[cH:24][cH:25][cH:26][c:27]([F:28])[cH:29]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][c:11]([F:12])[cH:13]... | N#Cc1cc(-c2cccc(F)c2)ccc1N.N#Cc1cc(Br)ccc1N.OB(O)c1cccc(F)c1 | CC(=O)c1cc(-c2cccc(F)c2)ccc1N.N#Cc1cc(-c2cccc(F)c2)ccc1N | null | null | C(C)(=O)OCC.C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | f4400f2c9795d874e2dad9b1d3b5f64074956f5d66c8ad207baffe373e4cd3f5 | 013308dabb1639b708a9e55ceea7cc7402b5b36b5e63b3b814177d2b4ee80cd3 | c1ccc(-c2ccccc2)cc1.c1ccc(-c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].N#[C;H0;D2;+0:6]-[c:7](:[c:8]):[c:9].O-B(-[OH;D1;+0:10])-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]>>[C;D1;H3:16]-[C;H0;D3;+0:6](=[O;H0;D1;+0:10])-[c:7](:[c:8]):[c:9].[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]):[c:4]:[c:5] | 43 | [{"value": 43.0, "product": "NC1=C(C=C(C=C1)C1=CC(=CC=C1)F)C(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Amino-3′-fluoro[1,1′-biphenyl]-3-carbonitrile was prepared from 3-fluorophenyl boronic acid and 2-amino-5-bromobenzonitrile according to the procedure of Example 4. A solution of 4-amino-3′-fluoro[1,1′-biphenyl]-3-carbonitrile (6.65 g, 31.3 mmol) in anhydrous THF (100 mL) was treated drop wise at room temperature und... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Nitrile.Boronic acid | Ketone | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | Br-.B | C(C)(=O)OCC.C1CCOC1 | null | null | N#Cc1cc(-c2cccc(F)c2)ccc1N.N#Cc1cc(Br)ccc1N.OB(O)c1cccc(F)c1>C(C)(=O)OCC.C1CCOC1>CC(=O)c1cc(-c2cccc(F)c2)ccc1N.N#Cc1cc(-c2cccc(F)c2)ccc1N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-015a9bbf3b544e6eab1c363da5e4cbf6 | CC(=O)c1cc(-c2cccc(F)c2)ccc1N>>CC(O)c1cc(-c2cccc(F)c2)ccc1N | S(=O)(=O)([O-])[O-].[NH4+].[NH4+].C(C)(=O)OCC.NC1=C(C=C(C=C1)C1=CC(=CC=C1)F)C(C)=O.[BH4-].[Na+]>>NC1=C(C=C(C=C1)C1=CC(=CC=C1)F)C(C)O | [CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][c:11]([F:12])[cH:13]2)[cH:14][cH:15][c:16]1[NH2:17]>>[CH3:1][CH:2]([OH:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][c:11]([F:12])[cH:13]2)[cH:14][cH:15][c:16]1[NH2:17] | CC(=O)c1cc(-c2cccc(F)c2)ccc1N | CC(O)c1cc(-c2cccc(F)c2)ccc1N | null | null | CO | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(-c2ccccc2)cc1 | [C;D1;H3:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4](:[c:5]):[c:6]>>[C;D1;H3:1]-[CH;D3;+0:2](-[OH;D1;+0:3])-[c:4](:[c:5]):[c:6] | 67 | [{"value": 67.0, "product": "NC1=C(C=C(C=C1)C1=CC(=CC=C1)F)C(C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.5, "product": "NC1=C(C=C(C=C1)C1=CC(=CC=C1)F)C(C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A solution of 1-(4-amino-3′-fluoro[1,1′-biphenyl]-3-yl)ethanone (3 g, 13 mmol) in anhydrous methanol (60 mL) was then treated at room temperature under nitrogen with sodium borohydride in a portion wise manner. After addition, the reaction mixture was stirred for 4 hours, treated with a saturated solution of aqueous am... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1ccccc1.c1ccccc1 | null | CO | null | 4 | CC(=O)c1cc(-c2cccc(F)c2)ccc1N>CO>CC(O)c1cc(-c2cccc(F)c2)ccc1N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c3c749d7e18a4396a634a5985bdbbed0 | CC1OC(=O)Nc2ccc(-c3cccc(F)c3)cc21.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1>>CC1OC(=S)Nc2ccc(-c3cccc(F)c3)cc21 | FC=1C=C(C=CC1)C=1C=CC2=C(C(OC(N2)=O)C)C1.COC=1C=CC(=CC1)P2(=S)SP(=S)(S2)C=3C=CC(=CC3)OC>>FC=1C=C(C=CC1)C=1C=CC2=C(C(OC(N2)=S)C)C1 | O=[C:4]1[O:3][CH:2]([CH3:1])[c:19]2[c:7]([cH:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][cH:14][c:15]([F:16])[cH:17]3)[cH:18]2)[NH:6]1.COc1ccc(P2(=S)SP(c3ccc(OC)cc3)(=[S:5])S2)cc1>>[CH3:1][CH:2]1[O:3][C:4](=[S:5])[NH:6][c:7]2[cH:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][cH:14][c:15]([F:16])[cH:17]3)[cH:18][c:19]21 | CC1OC(=O)Nc2ccc(-c3cccc(F)c3)cc21.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1 | CC1OC(=S)Nc2ccc(-c3cccc(F)c3)cc21 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 97d5668e697b90041eba9dad68ad83f7a1cdfe0944b559f928d28ab2564e8d10 | c331ef400a59f343eb23abd2f965cf1719390c2753d5de53af30054e75d29d94 | S=C1Nc2ccc(-c3ccccc3)cc2CO1 | C-O-c1:c:c:c(-P2(=S)-S-P(=[S;H0;D1;+0:1])(-c3:c:c:c(-O-C):c:c:3)-S-2):c:c:1.O=[C;H0;D3;+0:2](-[#7:3]-[c:4])-[#8:5]-[C:6]>>[C:6]-[#8:5]-[C;H0;D3;+0:2](=[S;H0;D1;+0:1])-[#7:3]-[c:4] | null | [] | null | null | null | null | A solution of 6-(3-fluorophenyl)-4-methyl-1,4-dihydro-2H-3,1-benzoxazin-2-one (0.15 g, 0.58 mmol) in toluene was treated with Lawesson's reagent according to the procedure in example 9 to yield 6-(3-fluorophenyl)-4-methyl-1,4-dihydro-2H-3,1-benzoxazin-2-thione (0.08 g, 50%) as an off-white solid (0.08 g, 50%): mp 173–1... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether.Ether.Monosulfide.Monosulfide | Ether.Thioamide | c1ccc2c(c1)COCN2.c1ccccc1.P1SPS1.c1ccccc1 | c1ccc2c(c1)COCN2 | c1ccc2c(c1)COCN2.c1ccccc1 | Other | C1(=CC=CC=C1)C | null | null | CC1OC(=O)Nc2ccc(-c3cccc(F)c3)cc21.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1>C1(=CC=CC=C1)C>CC1OC(=S)Nc2ccc(-c3cccc(F)c3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-009c54948d154e898818fbcb52be95ff | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.Cc1cc(C#N)sc1Br>>Cc1cc(C#N)sc1-c1ccc2c(c1)C(C)(C)OC(=O)N2 | CC1(OC(NC2=C1C=C(C=C2)B(O)O)=O)C.BrC1=C(C=C(S1)C#N)C>>CC1(C2=C(NC(O1)=O)C=CC(=C2)C2=C(C=C(S2)C#N)C)C | OB(O)[c:9]1[cH:10][cH:11][c:12]2[c:13]([cH:14]1)[C:15]([CH3:16])([CH3:17])[O:18][C:19](=[O:20])[NH:21]2.Br[c:8]1[c:2]([CH3:1])[cH:3][c:4]([C:5]#[N:6])[s:7]1>>[CH3:1][c:2]1[cH:3][c:4]([C:5]#[N:6])[s:7][c:8]1-[c:9]1[cH:10][cH:11][c:12]2[c:13]([cH:14]1)[C:15]([CH3:16])([CH3:17])[O:18][C:19](=[O:20])[NH:21]2 | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.Cc1cc(C#N)sc1Br | Cc1cc(C#N)sc1-c1ccc2c(c1)C(C)(C)OC(=O)N2 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 0b5bebfae8e49ed7172cda779db0d9a1ee34897b702e6169adb1825468a1d911 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Nc2ccc(-c3cccs3)cc2CO1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1-[C;D1;H3:6].O-B(-O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]>>[C;D1;H3:6]-[c:5]1:[c:4]:[c:3]:[#16;a:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11] | null | [] | null | null | null | null | 5-(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)-4-methyl-thiophene-2-carbonitrile was prepared, according to the procedure in Example 5 using (1,4-dihydro-4,4-dimethyl-2-oxo-2H-3,1-benzoxazin-6-yl)boronic acid and 5-bromo-4-methyl-2-thiophenecarbonitrile, as an off-white solid: mp 195–200° C.; 1H-NMR (DM... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)COCN2.c1ccsc1 | c1ccsc1.c1ccc2c(c1)COCN2 | c1ccsc1.c1ccc2c(c1)COCN2 | HBr.B | null | null | null | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.Cc1cc(C#N)sc1Br>>Cc1cc(C#N)sc1-c1ccc2c(c1)C(C)(C)OC(=O)N2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ab8530a118334e6b91e2f78ad5b520fd | COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1.Cc1cc(C#N)sc1-c1ccc2c(c1)C(C)(C)OC(=O)N2>>Cc1cc(C#N)sc1-c1ccc2c(c1)C(C)(C)OC(=S)N2 | CC1(OC(NC2=C1C=C(C=C2)C2=C(C=C(S2)C#N)C)=O)C.COC=1C=CC(=CC1)P2(=S)SP(=S)(S2)C=3C=CC(=CC3)OC>>CC1(OC(NC2=C1C=C(C=C2)C2=C(C=C(S2)C#N)C)=S)C | COc1ccc(P2(=S)SP(c3ccc(OC)cc3)(=[S:20])S2)cc1.O=[C:19]1[O:18][C:15]([CH3:16])([CH3:17])[c:13]2[c:12]([cH:11][cH:10][c:9](-[c:8]3[c:2]([CH3:1])[cH:3][c:4]([C:5]#[N:6])[s:7]3)[cH:14]2)[NH:21]1>>[CH3:1][c:2]1[cH:3][c:4]([C:5]#[N:6])[s:7][c:8]1-[c:9]1[cH:10][cH:11][c:12]2[c:13]([cH:14]1)[C:15]([CH3:16])([CH3:17])[O:18][C:1... | COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1.Cc1cc(C#N)sc1-c1ccc2c(c1)C(C)(C)OC(=O)N2 | Cc1cc(C#N)sc1-c1ccc2c(c1)C(C)(C)OC(=S)N2 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 97d5668e697b90041eba9dad68ad83f7a1cdfe0944b559f928d28ab2564e8d10 | c331ef400a59f343eb23abd2f965cf1719390c2753d5de53af30054e75d29d94 | S=C1Nc2ccc(-c3cccs3)cc2CO1 | C-O-c1:c:c:c(-P2(=S)-S-P(=[S;H0;D1;+0:1])(-c3:c:c:c(-O-C):c:c:3)-S-2):c:c:1.O=[C;H0;D3;+0:2](-[#7:3]-[c:4])-[#8:5]-[C:6]>>[C:6]-[#8:5]-[C;H0;D3;+0:2](=[S;H0;D1;+0:1])-[#7:3]-[c:4] | 51.6 | [{"value": 46.0, "product": "CC1(OC(NC2=C1C=C(C=C2)C2=C(C=C(S2)C#N)C)=S)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.6, "product": "CC1(OC(NC2=C1C=C(C=C2)C2=C(C=C(S2)C#N)C)=S)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-4-methylthiophene-2-carbonitrile (5 g, 16.7 mmol) in anhydrous toluene was added, at room temperature under a blanket of nitrogen, Lawesson's reagent (6 g, 14.8 mmol). The reaction mixture was heated at reflux for 2 hrs, allowed to cool to room ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether.Ether.Monosulfide.Monosulfide | Ether.Thioamide | c1ccccc1.P1SPS1.c1ccccc1.c1ccc2c(c1)COCN2 | c1ccc2c(c1)COCN2 | c1ccsc1.c1ccc2c(c1)COCN2 | Other | C1(=CC=CC=C1)C | null | null | COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1.Cc1cc(C#N)sc1-c1ccc2c(c1)C(C)(C)OC(=O)N2>C1(=CC=CC=C1)C>Cc1cc(C#N)sc1-c1ccc2c(c1)C(C)(C)OC(=S)N2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-db15c1f0a4b242c197627609f45b94e7 | CC(C)(C)OC(=O)n1cccc1-c1ccc2c(c1)C(C)(C)OC(=O)N2.O=C=NS(=O)(=O)Cl>>CC(C)(C)OC(=O)n1c(C#N)ccc1-c1ccc2c(c1)C(C)(C)OC(=O)N2 | O.CN(C)C=O.C(C)(C)(C)OC(=O)N1C(=CC=C1)C1=CC2=C(NC(OC2(C)C)=O)C=C1.ClS(=O)(=O)N=C=O>>C(C)(C)(C)OC(=O)N1C(=CC=C1C#N)C1=CC2=C(NC(OC2(C)C)=O)C=C1 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[n:8]1[cH:9][cH:12][cH:13][c:14]1-[c:15]1[cH:16][cH:17][c:18]2[c:19]([cH:20]1)[C:21]([CH3:22])([CH3:23])[O:24][C:25](=[O:26])[NH:27]2.O=S(=O)(Cl)[N:11]=[C:10]=O>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[n:8]1[c:9]([C:10]#[N:11])[cH:12][cH:13][c:14]1-[c:15]1[cH:16]... | CC(C)(C)OC(=O)n1cccc1-c1ccc2c(c1)C(C)(C)OC(=O)N2.O=C=NS(=O)(=O)Cl | CC(C)(C)OC(=O)n1c(C#N)ccc1-c1ccc2c(c1)C(C)(C)OC(=O)N2 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 93891aa133e496a7c8d865002378d802d0a23f0a704cdcc3cfb3ca39bcb75312 | b8bacb90390718f4555f6dee24489036b4f724075b0543a5a9bf8e9abad9b32c | O=C1Nc2ccc(-c3ccc[nH]3)cc2CO1 | Cl-S(=O)(=O)-[N;H0;D2;+0:1]=[C;H0;D2;+0:2]=O.[C;D1;H3:3]-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[#8:7]-[C:8](=[O;D1;H0:9])-[#7;a:10]1:[c:11]:[c:12]:[c:13]:[cH;D2;+0:14]:1>>[C;D1;H3:3]-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[#8:7]-[C:8](=[O;D1;H0:9])-[#7;a:10]1:[c:11]:[c:12]:[c:13]:[c;H0;D3;+0:14]:1-[C;H0;D2;+0:2]#[N;H0;D1;+0:1] | 52 | [{"value": 52.0, "product": "C(C)(C)(C)OC(=O)N1C(=CC=C1C#N)C1=CC2=C(NC(OC2(C)C)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.6, "product": "C(C)(C)(C)OC(=O)N1C(=CC=C1C#N)C1=CC2=C(NC(OC2(C)C)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 90 | MINUTE | To a solution of 2-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-benzo [d][1,3]oxazin-6-yl)-pyrrole-1-carboxylic acid tert-butyl ester (2.0 g, 5.8 mmol) in THF (anhydrous, 50 mL) at −78° C. was added chlorosulfonyl isocyanate (0.66 mL, 6.7 mmol). After 90 min, DMF (9 mL, 116 mmol) was added and the reaction was allowed to warm to... | 10.6084/m9.figshare.5104873.v1 | null | null | Nitrile | c1ccc[nH]1 | c1ccc[nH]1 | c1ccc[nH]1.c1ccc2c(c1)COCN2 | HCl | C1CCOC1 | null | 1.5 | CC(C)(C)OC(=O)n1cccc1-c1ccc2c(c1)C(C)(C)OC(=O)N2.O=C=NS(=O)(=O)Cl>C1CCOC1>CC(C)(C)OC(=O)n1c(C#N)ccc1-c1ccc2c(c1)C(C)(C)OC(=O)N2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4ff7fa3e145d4def93231e90d3a108d9 | CC(C)(C)OC(=O)n1c(C#N)ccc1-c1ccc2c(c1)C(C)(C)OC(=O)N2.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1>>CC(C)(C)OC(=O)n1c(C#N)ccc1-c1ccc2c(c1)C(C)(C)OC(=S)N2 | C(C)(C)(C)OC(=O)N1C(=CC=C1C#N)C1=CC2=C(NC(OC2(C)C)=O)C=C1.COC=1C=CC(=CC1)P2(=S)SP(=S)(S2)C=3C=CC(=CC3)OC>>C(#N)C=1N(C(=CC1)C=1C=CC2=C(C(OC(N2)=S)(C)C)C1)C(=O)OC(C)(C)C | O=[C:25]1[O:24][C:21]([CH3:22])([CH3:23])[c:19]2[c:18]([cH:17][cH:16][c:15](-[c:14]3[n:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[c:9]([C:10]#[N:11])[cH:12][cH:13]3)[cH:20]2)[NH:27]1.COc1ccc(P2(=S)SP(c3ccc(OC)cc3)(=[S:26])S2)cc1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[n:8]1[c:9]([C:10]#[N:11])[cH:12... | CC(C)(C)OC(=O)n1c(C#N)ccc1-c1ccc2c(c1)C(C)(C)OC(=O)N2.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1 | CC(C)(C)OC(=O)n1c(C#N)ccc1-c1ccc2c(c1)C(C)(C)OC(=S)N2 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 97d5668e697b90041eba9dad68ad83f7a1cdfe0944b559f928d28ab2564e8d10 | c331ef400a59f343eb23abd2f965cf1719390c2753d5de53af30054e75d29d94 | S=C1Nc2ccc(-c3ccc[nH]3)cc2CO1 | C-O-c1:c:c:c(-P2(=S)-S-P(=[S;H0;D1;+0:1])(-c3:c:c:c(-O-C):c:c:3)-S-2):c:c:1.O=[C;H0;D3;+0:2](-[#7:3]-[c:4])-[#8:5]-[C:6]>>[C:6]-[#8:5]-[C;H0;D3;+0:2](=[S;H0;D1;+0:1])-[#7:3]-[c:4] | 38 | [{"value": 38.0, "product": "C(#N)C=1N(C(=CC1)C=1C=CC2=C(C(OC(N2)=S)(C)C)C1)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 34.1, "product": "C(#N)C=1N(C(=CC1)C=1C=CC2=C(C(OC(N2)=S)(C)C)C1)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | To 2-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-benzo [d][1,3]oxazin-6-yl)-5-cyano-pyrrole-1-carboxylic acid tert-butyl ester (1.3 g, 35 mmol, 1 eq) in toluene (130 mL) was added Lawesson's reagent (1.58 g, 3.9 mmol, 1.1 eq) and the reaction mixture was heated to 80° C. for 2 h. The solvent was removed in vacuo and the residue... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether.Ether.Monosulfide.Monosulfide | Ether.Thioamide | c1ccc2c(c1)COCN2.c1ccccc1.P1SPS1.c1ccccc1 | c1ccc2c(c1)COCN2 | c1ccc[nH]1.c1ccc2c(c1)COCN2 | Other | C1(=CC=CC=C1)C | 80 | null | CC(C)(C)OC(=O)n1c(C#N)ccc1-c1ccc2c(c1)C(C)(C)OC(=O)N2.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1>C1(=CC=CC=C1)C>CC(C)(C)OC(=O)n1c(C#N)ccc1-c1ccc2c(c1)C(C)(C)OC(=S)N2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6015e02f55894b85954ab8a8d7c24322 | CC(C)(C)OC(=O)n1c(C#N)ccc1-c1ccc2c(c1)C(C)(C)OC(=S)N2>>CC1(C)OC(=S)Nc2ccc(-c3ccc(C#N)[nH]3)cc21 | C(#N)C=1N(C(=CC1)C=1C=CC2=C(C(OC(N2)=S)(C)C)C1)C(=O)OC(C)(C)C.CC[O-].[Na+]>>CC1(OC(NC2=C1C=C(C=C2)C2=CC=C(N2)C#N)=S)C | CC(C)(C)OC(=O)[n:18]1[c:12](-[c:11]2[cH:10][cH:9][c:8]3[c:20]([cH:19]2)[C:2]([CH3:1])([CH3:3])[O:4][C:5](=[S:6])[NH:7]3)[cH:13][cH:14][c:15]1[C:16]#[N:17]>>[CH3:1][C:2]1([CH3:3])[O:4][C:5](=[S:6])[NH:7][c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][c:15]([C:16]#[N:17])[nH:18]3)[cH:19][c:20]21 | CC(C)(C)OC(=O)n1c(C#N)ccc1-c1ccc2c(c1)C(C)(C)OC(=S)N2 | CC1(C)OC(=S)Nc2ccc(-c3ccc(C#N)[nH]3)cc21 | null | null | CCO.C1CCOC1 | Reduction | Boc amine deprotection | 252fa31ad5d8c65b4b59e02901526a39d1fe6cc2afabebaaa627f6f163db1fda | e1bf5a54b1f87284564f107662531aec2aff7de801e4606340967b38924afb28 | S=C1Nc2ccc(-c3ccc[nH]3)cc2CO1 | C-C(-C)(-C)-O-C(=O)-[n;H0;D3;+0:1]1:[c:2](-[c:3]):[c:4]:[c:5]:[c:6]:1-[C:7]#[N;D1;H0:8]>>[N;D1;H0:8]#[C:7]-[c:6]1:[c:5]:[c:4]:[c:2](-[c:3]):[nH;D2;+0:1]:1 | 73.3 | [{"value": 73.0, "product": "CC1(OC(NC2=C1C=C(C=C2)C2=CC=C(N2)C#N)=S)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.3, "product": "CC1(OC(NC2=C1C=C(C=C2)C2=CC=C(N2)C#N)=S)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | To a solution of tert-butyl 2-cyano-5-(4,4-dimethyl-2-thioxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-1H-pyrrole-1-carboxylate (0.5 g, 1.3 mmol, 1 eq) in THF (5 mL) was added NaOEt (0.27 g, 3.9 mmol, 3 eq) in EtOH (5 mL) and the reaction was heated to 80° C. for 2 h. The solvents were removed in vacuo and the residue partit... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Boc | null | c1ccc[nH]1 | c1cc[nH]c1 | c1ccc2c(c1)COCN2.c1cc[nH]c1 | HO- | CCO.C1CCOC1 | 80 | null | CC(C)(C)OC(=O)n1c(C#N)ccc1-c1ccc2c(c1)C(C)(C)OC(=S)N2>CCO.C1CCOC1>CC1(C)OC(=S)Nc2ccc(-c3ccc(C#N)[nH]3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4ea1fcb9fde041f49e9ca6d730038d52 | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.N#CCc1cccc(Br)n1>>CC1(C)OC(=O)Nc2ccc(-c3cccc(CC#N)n3)cc21 | CC1(OC(NC2=C1C=C(C=C2)B(O)O)=O)C.BrC1=CC=CC(=N1)CC#N>>CC1(OC(NC2=C1C=C(C=C2)C2=CC=CC(=N2)CC#N)=O)C | OB(O)[c:11]1[cH:10][cH:9][c:8]2[c:22]([cH:21]1)[C:2]([CH3:1])([CH3:3])[O:4][C:5](=[O:6])[NH:7]2.Br[c:12]1[cH:13][cH:14][cH:15][c:16]([CH2:17][C:18]#[N:19])[n:20]1>>[CH3:1][C:2]1([CH3:3])[O:4][C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][c:16]([CH2:17][C:18]#[N:19])[n:20]3)[cH:21][c:22]21 | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.N#CCc1cccc(Br)n1 | CC1(C)OC(=O)Nc2ccc(-c3cccc(CC#N)n3)cc21 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | c51c4a152462d99e6f839fd7f446f3100033003c41266a5cf8db98a2232a1323 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Nc2ccc(-c3ccccn3)cc2CO1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[#7;a:2]:[c:3] | null | [] | null | null | null | null | [6-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)pyridin-2-yl]acetonitrile was prepared, according to the procedure of Example 5 using (1,4-dihydro-4,4-dimethyl-2-oxo-2H-3,1-benzoxazin-6-yl)boronic acid and (6-bromo-2-pyridyl)acetonitrile (J. Org. Chem. 1988, 53, 786–790), as an off-white solid: mp 210–212.5° ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)COCN2.c1ccncc1 | c1ccc2c(c1)COCN2.c1ccncc1 | c1ccc2c(c1)COCN2.c1ccncc1 | HBr.B | null | null | null | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.N#CCc1cccc(Br)n1>>CC1(C)OC(=O)Nc2ccc(-c3cccc(CC#N)n3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-177a096a64d244cd9238a2669e7e79fc | CC1(C)OC(=O)Nc2ccc(-c3cccc(CC#N)n3)cc21.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1>>CC1(C)OC(=S)Nc2ccc(-c3cccc(CC#N)n3)cc21 | CC1(OC(NC2=C1C=C(C=C2)C2=CC=CC(=N2)CC#N)=O)C.COC=1C=CC(=CC1)P2(=S)SP(=S)(S2)C=3C=CC(=CC3)OC>>CC1(OC(NC2=C1C=C(C=C2)C2=CC=CC(=N2)CC#N)=S)C | O=[C:5]1[O:4][C:2]([CH3:1])([CH3:3])[c:22]2[c:8]([cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][c:16]([CH2:17][C:18]#[N:19])[n:20]3)[cH:21]2)[NH:7]1.COc1ccc(P2(=S)SP(c3ccc(OC)cc3)(=[S:6])S2)cc1>>[CH3:1][C:2]1([CH3:3])[O:4][C:5](=[S:6])[NH:7][c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][c:16]([CH2:17][C:18]... | CC1(C)OC(=O)Nc2ccc(-c3cccc(CC#N)n3)cc21.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1 | CC1(C)OC(=S)Nc2ccc(-c3cccc(CC#N)n3)cc21 | null | null | CC=1C=CC(=CC1)C | Heteroatom Alkylation and Arylation | OtherReaction | 97d5668e697b90041eba9dad68ad83f7a1cdfe0944b559f928d28ab2564e8d10 | c331ef400a59f343eb23abd2f965cf1719390c2753d5de53af30054e75d29d94 | S=C1Nc2ccc(-c3ccccn3)cc2CO1 | C-O-c1:c:c:c(-P2(=S)-S-P(=[S;H0;D1;+0:1])(-c3:c:c:c(-O-C):c:c:3)-S-2):c:c:1.O=[C;H0;D3;+0:2](-[#7:3]-[c:4])-[#8:5]-[C:6]>>[C:6]-[#8:5]-[C;H0;D3;+0:2](=[S;H0;D1;+0:1])-[#7:3]-[c:4] | 92.3 | [{"value": 48.0, "product": "CC1(OC(NC2=C1C=C(C=C2)C2=CC=CC(=N2)CC#N)=S)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.3, "product": "CC1(OC(NC2=C1C=C(C=C2)C2=CC=CC(=N2)CC#N)=S)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To [6-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)pyridin-2-yl]acetonitrile (80 mg, 0.27 mmol, 1 eq) in p-xylene (10 mL) was added Lawesson's reagent (55 mg, 0.14 mmol, 0.5 eq) and the reaction was heated to reflux for 2 hours. The reaction was cooled to room temperature and adsorbed onto silica gel. Purific... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether.Ether.Monosulfide.Monosulfide | Ether.Thioamide | c1ccc2c(c1)COCN2.c1ccccc1.P1SPS1.c1ccccc1 | c1ccc2c(c1)COCN2 | c1ccc2c(c1)COCN2.c1ccncc1 | Other | CC=1C=CC(=CC1)C | null | null | CC1(C)OC(=O)Nc2ccc(-c3cccc(CC#N)n3)cc21.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1>CC=1C=CC(=CC1)C>CC1(C)OC(=S)Nc2ccc(-c3cccc(CC#N)n3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ecc1c2e24f1b4386b9eb3ea4bd1f9cc0 | CC1(C)OC(=O)Nc2ccc(-c3ccc(C#N)[nH]3)cc21.CI>>Cn1c(C#N)ccc1-c1ccc2c(c1)C(C)(C)OC(=O)N2 | O.IC.CC1(OC(NC2=C1C=C(C=C2)C2=CC=C(N2)C#N)=O)C.C([O-])([O-])=O.[K+].[K+]>>CC1(OC(NC2=C1C=C(C=C2)C2=CC=C(N2C)C#N)=O)C | [nH:2]1[c:3]([C:4]#[N:5])[cH:6][cH:7][c:8]1-[c:9]1[cH:10][cH:11][c:12]2[c:13]([cH:14]1)[C:15]([CH3:16])([CH3:17])[O:18][C:19](=[O:20])[NH:21]2.I[CH3:1]>>[CH3:1][n:2]1[c:3]([C:4]#[N:5])[cH:6][cH:7][c:8]1-[c:9]1[cH:10][cH:11][c:12]2[c:13]([cH:14]1)[C:15]([CH3:16])([CH3:17])[O:18][C:19](=[O:20])[NH:21]2 | CC1(C)OC(=O)Nc2ccc(-c3ccc(C#N)[nH]3)cc21.CI | Cn1c(C#N)ccc1-c1ccc2c(c1)C(C)(C)OC(=O)N2 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 3b0bd5806650bb387428bf36a5e436078e57d40d2afdf9e751829e2a02da9e1d | 7a358c636daddc97c1fb4c29f378044d7eac3f01815d9966e599841f642d631a | O=C1Nc2ccc(-c3ccc[nH]3)cc2CO1 | I-[CH3;D1;+0:1].[N;D1;H0:2]#[C:3]-[c:4]1:[c:5]:[c:6]:[c:7](-[c:8]):[nH;D2;+0:9]:1>>[CH3;D1;+0:1]-[n;H0;D3;+0:9]1:[c:4](-[C:3]#[N;D1;H0:2]):[c:5]:[c:6]:[c:7]:1-[c:8] | 41 | [{"value": 41.0, "product": "CC1(OC(NC2=C1C=C(C=C2)C2=CC=C(N2C)C#N)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.5, "product": "CC1(OC(NC2=C1C=C(C=C2)C2=CC=C(N2C)C#N)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a solution of 5-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-1H-pyrrole-2-carbonitrile (1 eq, 71 mg, 0.27 mmol) in dimethylformamide (0.5 mL) was added potassium carbonate (5 eq, 0.18 g, 0.1.35 mmol). After 10 min, iodomethane (3 eq, 0.05 mL, 0.81 mmol) was added and the suspension was stirred for 2 hours... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1cc[nH]c1 | c1ccc[nH]1 | c1ccc[nH]1.c1ccc2c(c1)COCN2 | HI | CN(C=O)C | null | 0.166667 | CC1(C)OC(=O)Nc2ccc(-c3ccc(C#N)[nH]3)cc21.CI>CN(C=O)C>Cn1c(C#N)ccc1-c1ccc2c(c1)C(C)(C)OC(=O)N2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e8794b502b524658ab1f47d116081e3c | CC1(C)OC(=O)Nc2ccc(-c3cc(C#N)cs3)cc21.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1>>CC1(C)OC(=S)Nc2ccc(-c3cc(C#N)cs3)cc21 | CC1(C2=C(NC(O1)=O)C=CC(=C2)C2=CC(=CS2)C#N)C.COC=1C=CC(=CC1)P2(=S)SP(=S)(S2)C=3C=CC(=CC3)OC>>CC1(C2=C(NC(O1)=S)C=CC(=C2)C2=CC(=CS2)C#N)C | O=[C:5]1[O:4][C:2]([CH3:1])([CH3:3])[c:20]2[c:8]([cH:9][cH:10][c:11](-[c:12]3[cH:13][c:14]([C:15]#[N:16])[cH:17][s:18]3)[cH:19]2)[NH:7]1.COc1ccc(P2(=S)SP(c3ccc(OC)cc3)(=[S:6])S2)cc1>>[CH3:1][C:2]1([CH3:3])[O:4][C:5](=[S:6])[NH:7][c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][c:14]([C:15]#[N:16])[cH:17][s:18]3)[cH:19][c:20]2... | CC1(C)OC(=O)Nc2ccc(-c3cc(C#N)cs3)cc21.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1 | CC1(C)OC(=S)Nc2ccc(-c3cc(C#N)cs3)cc21 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 97d5668e697b90041eba9dad68ad83f7a1cdfe0944b559f928d28ab2564e8d10 | c331ef400a59f343eb23abd2f965cf1719390c2753d5de53af30054e75d29d94 | S=C1Nc2ccc(-c3cccs3)cc2CO1 | C-O-c1:c:c:c(-P2(=S)-S-P(=[S;H0;D1;+0:1])(-c3:c:c:c(-O-C):c:c:3)-S-2):c:c:1.O=[C;H0;D3;+0:2](-[#7:3]-[c:4])-[#8:5]-[C:6]>>[C:6]-[#8:5]-[C;H0;D3;+0:2](=[S;H0;D1;+0:1])-[#7:3]-[c:4] | null | [] | null | null | null | null | The title compound was prepared in a manner similar to Example 16 using 5-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-benzo [d][1,3]oxazin-6-yl) thiophene-3-carbonitrile and Lawesson's reagent. The product was obtained in the form of yellow crystals: m.p. 258–259° C. 1H NMR (DMSO-d6) δ 12.3 (s, 1 H), 8.54 (d, 1H, J=0.9 Hz), 7.9... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether.Ether.Monosulfide.Monosulfide | Ether.Thioamide | c1ccc2c(c1)COCN2.c1ccccc1.P1SPS1.c1ccccc1 | c1ccc2c(c1)COCN2 | c1ccc2c(c1)COCN2.c1ccsc1 | Other | O | null | null | CC1(C)OC(=O)Nc2ccc(-c3cc(C#N)cs3)cc21.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1>O>CC1(C)OC(=S)Nc2ccc(-c3cc(C#N)cs3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-26f4d3e740fb416bb2f637f77eb85032 | CCn1c(C#N)ccc1-c1ccc2c(c1)C(C)(C)OC(=O)N2.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1>>CCn1c(C#N)ccc1-c1ccc2c(c1)C(C)(C)OC(=S)N2 | CC1(OC(NC2=C1C=C(C=C2)C2=CC=C(N2CC)C#N)=O)C.COC=1C=CC(=CC1)P2(=S)SP(=S)(S2)C=3C=CC(=CC3)OC>>CC1(OC(NC2=C1C=C(C=C2)C2=CC=C(N2CC)C#N)=S)C | O=[C:20]1[O:19][C:16]([CH3:17])([CH3:18])[c:14]2[c:13]([cH:12][cH:11][c:10](-[c:9]3[n:3]([CH2:2][CH3:1])[c:4]([C:5]#[N:6])[cH:7][cH:8]3)[cH:15]2)[NH:22]1.COc1ccc(P2(=S)SP(c3ccc(OC)cc3)(=[S:21])S2)cc1>>[CH3:1][CH2:2][n:3]1[c:4]([C:5]#[N:6])[cH:7][cH:8][c:9]1-[c:10]1[cH:11][cH:12][c:13]2[c:14]([cH:15]1)[C:16]([CH3:17])([... | CCn1c(C#N)ccc1-c1ccc2c(c1)C(C)(C)OC(=O)N2.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1 | CCn1c(C#N)ccc1-c1ccc2c(c1)C(C)(C)OC(=S)N2 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 97d5668e697b90041eba9dad68ad83f7a1cdfe0944b559f928d28ab2564e8d10 | c331ef400a59f343eb23abd2f965cf1719390c2753d5de53af30054e75d29d94 | S=C1Nc2ccc(-c3ccc[nH]3)cc2CO1 | C-O-c1:c:c:c(-P2(=S)-S-P(=[S;H0;D1;+0:1])(-c3:c:c:c(-O-C):c:c:3)-S-2):c:c:1.O=[C;H0;D3;+0:2](-[#7:3]-[c:4])-[#8:5]-[C:6]>>[C:6]-[#8:5]-[C;H0;D3;+0:2](=[S;H0;D1;+0:1])-[#7:3]-[c:4] | null | [] | null | null | null | null | The title compound was prepared according to the procedure for Example 16 from 5-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-1-ethyl-1H-pyrrole-2-carbonitrile and Lawesson's reagent. The product was obtained in the form of white needles: mp 212–213° C.; 1H-NMR (DMSO-d6) δ 1.25 (t, 3H, J-=7 Hz), 1.68 (s, 6H)... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether.Ether.Monosulfide.Monosulfide | Ether.Thioamide | c1ccc2c(c1)COCN2.c1ccccc1.P1SPS1.c1ccccc1 | c1ccc2c(c1)COCN2 | c1ccc[nH]1.c1ccc2c(c1)COCN2 | Other | null | null | null | CCn1c(C#N)ccc1-c1ccc2c(c1)C(C)(C)OC(=O)N2.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1>>CCn1c(C#N)ccc1-c1ccc2c(c1)C(C)(C)OC(=S)N2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1b0ec4d5d2d24b0a8fad1554ad70fa06 | BrCCCCCBr.Nc1ccc(Br)cc1C(=O)O>>Nc1ccc(Br)cc1C1(O)CCCCC1 | NC1=C(C(=O)O)C=C(C=C1)Br.BrCCCCCBr>>NC1=C(C=C(C=C1)Br)C1(CCCCC1)O | Br[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]Br.O=[C:9]([c:8]1[c:2]([NH2:1])[cH:3][cH:4][c:5]([Br:6])[cH:7]1)[OH:10]>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([Br:6])[cH:7][c:8]1[C:9]1([OH:10])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1 | BrCCCCCBr.Nc1ccc(Br)cc1C(=O)O | Nc1ccc(Br)cc1C1(O)CCCCC1 | null | null | null | C-C Coupling | OtherReaction | 9e5c378844480bc1e13d9f9ac0348ea73b576c5d624749e5b7c271d467b79866 | 822e973608b3f0d7a885c0b5584a307ebd92fa7f731ed8882df7c309f292b5c4 | c1ccc(C2CCCCC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]-[CH2;D2;+0:5]-Br.O=[C;H0;D3;+0:6](-[O;D1;H1:7])-[c:8](:[c:9]):[c:10]>>[O;D1;H1:7]-[C;H0;D4;+0:6]1(-[c:8](:[c:9]):[c:10])-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]-[CH2;D2;+0:5]-1 | null | [] | null | null | null | null | 1-(2-Amino-5-bromo-phenyl) cyclohexanol was prepared, according to the procedure of Example 1 using 2-amino-5-bromobenzoic acid and the Grignard reagent prepared from 1,5-dibromopentane, as a clear oil: 1H-NMR (DMSO-d6) δ 7.07 (d, 1H, J=2.3 Hz), 7.03 (dd, 1H, J=8.4, 2.4 Hz), 6.55 (d, 1H, J=8.6 Hz), 5.49 (s, 2H, D2O exc... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Carboxylic acid | Tertiary alcohol | null | C1CCCCC1 | c1ccccc1.C1CCCCC1 | Br- | null | null | null | BrCCCCCBr.Nc1ccc(Br)cc1C(=O)O>>Nc1ccc(Br)cc1C1(O)CCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-387f011555704388b9d4a17550cb3977 | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.Cc1cc(Br)cc(Br)c1>>Cc1cc(Br)cc(-c2ccc3c(c2)C(C)(C)OC(=O)N3)c1 | CC1(OC(NC2=C1C=C(C=C2)B(O)O)=O)C.BrC=1C=C(C=C(C1)Br)C>>BrC=1C=C(C=C(C1)C)C1=CC2=C(NC(OC2(C)C)=O)C=C1 | OB(O)[c:8]1[cH:9][cH:10][c:11]2[c:12]([cH:13]1)[C:14]([CH3:15])([CH3:16])[O:17][C:18](=[O:19])[NH:20]2.Br[c:7]1[cH:6][c:4]([Br:5])[cH:3][c:2]([CH3:1])[cH:21]1>>[CH3:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]3[c:12]([cH:13]2)[C:14]([CH3:15])([CH3:16])[O:17][C:18](=[O:19])[NH:20]3)[cH:21]1 | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.Cc1cc(Br)cc(Br)c1 | Cc1cc(Br)cc(-c2ccc3c(c2)C(C)(C)OC(=O)N3)c1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 0fa2a30709dcd56081dfd73304ec3a2ee5346cb80b80e4b5dc426c319dd3d4bb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Nc2ccc(-c3ccccc3)cc2CO1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:10]:[c:9]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | null | [] | null | null | null | null | 6-(3-Bromo-5-methyl-phenyl)-4,4-dimethyl-1,4-dihydrobenzo-[d][1,3]oxazin-2-one was prepared, using (4,4-dimethyl-1,4-dihydro-2-oxo-2H-3,1-benzoxazin-6-yl)boronic acid and 3,5-dibromotoluene according to the procedure of Example 5, as a white solid: mp 231–233° C.; 1H-NMR (DMSO-d6) δ 10.4 (s, 1H), 7.66 (s, 1H), 7.58–7.5... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)COCN2.c1ccccc1 | c1ccccc1.c1ccc2c(c1)COCN2 | c1ccccc1.c1ccc2c(c1)COCN2 | HBr.B | null | null | null | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.Cc1cc(Br)cc(Br)c1>>Cc1cc(Br)cc(-c2ccc3c(c2)C(C)(C)OC(=O)N3)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-09cddcd17bf84b12b7190e0584d9b2ef | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.FC(F)(F)Oc1cc(Br)cc(Br)c1>>CC1(C)OC(=O)Nc2ccc(-c3cc(Br)cc(OC(F)(F)F)c3)cc21 | CC1(OC(NC2=C1C=C(C=C2)B(O)O)=O)C.BrC1=CC(=CC(=C1)OC(F)(F)F)Br>>BrC=1C=C(C=C(C1)OC(F)(F)F)C1=CC2=C(NC(OC2(C)C)=O)C=C1 | OB(O)[c:11]1[cH:10][cH:9][c:8]2[c:25]([cH:24]1)[C:2]([CH3:1])([CH3:3])[O:4][C:5](=[O:6])[NH:7]2.Br[c:12]1[cH:13][c:14]([Br:15])[cH:16][c:17]([O:18][C:19]([F:20])([F:21])[F:22])[cH:23]1>>[CH3:1][C:2]1([CH3:3])[O:4][C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][c:14]([Br:15])[cH:16][c:17]([O:18][C:19]([F:20... | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.FC(F)(F)Oc1cc(Br)cc(Br)c1 | CC1(C)OC(=O)Nc2ccc(-c3cc(Br)cc(OC(F)(F)F)c3)cc21 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 0fa2a30709dcd56081dfd73304ec3a2ee5346cb80b80e4b5dc426c319dd3d4bb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Nc2ccc(-c3ccccc3)cc2CO1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | null | [] | null | null | null | null | 6-(3-Bromo-5-trifluoromethoxy-phenyl)-4,4-dimethyl-1,4-dihydrobenzo [d][1,3]-oxazin-2-one was prepared, using (4,4-dimethyl-1,4-dihydro-2-oxo-2H-3,1-benzoxazin-6-yl)boronic acid and 1, 3-dibromo-5-trifluoromethoxybenzene according to the procedure of Example 5, as a white solid: mp 214–216° C.; 1H-NMR (DMSO-d6) δ 10.4 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)COCN2.c1ccccc1 | c1ccc2c(c1)COCN2.c1ccccc1 | c1ccc2c(c1)COCN2.c1ccccc1 | HBr.B | null | null | null | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.FC(F)(F)Oc1cc(Br)cc(Br)c1>>CC1(C)OC(=O)Nc2ccc(-c3cc(Br)cc(OC(F)(F)F)c3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4c7762fc30dd474b866ea6126d0bc089 | CC1(C)OC(=O)Nc2ccc(Br)cc21.OB(O)c1cc(Cl)cc(Cl)c1>>CC1(C)OC(=O)Nc2ccc(-c3cc(Cl)cc(Cl)c3)cc21 | BrC1=CC2=C(NC(OC2(C)C)=O)C=C1.ClC=1C=C(C=C(C1)Cl)B(O)O>>ClC=1C=C(C=C(C1)Cl)C1=CC2=C(NC(OC2(C)C)=O)C=C1 | Br[c:11]1[cH:10][cH:9][c:8]2[c:21]([cH:20]1)[C:2]([CH3:1])([CH3:3])[O:4][C:5](=[O:6])[NH:7]2.OB(O)[c:12]1[cH:13][c:14]([Cl:15])[cH:16][c:17]([Cl:18])[cH:19]1>>[CH3:1][C:2]1([CH3:3])[O:4][C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][c:14]([Cl:15])[cH:16][c:17]([Cl:18])[cH:19]3)[cH:20][c:21]21 | CC1(C)OC(=O)Nc2ccc(Br)cc21.OB(O)c1cc(Cl)cc(Cl)c1 | CC1(C)OC(=O)Nc2ccc(-c3cc(Cl)cc(Cl)c3)cc21 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 0fa2a30709dcd56081dfd73304ec3a2ee5346cb80b80e4b5dc426c319dd3d4bb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Nc2ccc(-c3ccccc3)cc2CO1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9]:[c:10] | null | [] | null | null | null | null | 6-(3,5-dichloro-phenyl)-4,4-dimethyl-1,4-dihydrobenzo-[d][1,3]oxazin-2-one was prepared, from 6-bromo-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one and 3,5-dichlorophenyl boronic acid according to the procedure of Example 4, as a white solid: mp 245–246° C.; 1H-NMR (DMSO-d6) δ 10.4 (s, 1H), 7.77 (m, 2H), 7.67–7.64... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)COCN2.c1ccccc1 | c1ccc2c(c1)COCN2.c1ccccc1 | c1ccc2c(c1)COCN2.c1ccccc1 | HBr.B | null | null | null | CC1(C)OC(=O)Nc2ccc(Br)cc21.OB(O)c1cc(Cl)cc(Cl)c1>>CC1(C)OC(=O)Nc2ccc(-c3cc(Cl)cc(Cl)c3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3a27f1abc1d34ba6aba1da24b87462ad | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.N#Cc1ccc(Br)o1>>CC1(C)OC(=O)Nc2ccc(-c3ccc(C#N)o3)cc21 | BrC=1OC(=CC1)C#N.CC1(OC(NC2=C1C=C(C=C2)B(O)O)=O)C>>CC1(C2=C(NC(O1)=O)C=CC(=C2)C2=CC=C(O2)C#N)C | OB(O)[c:11]1[cH:10][cH:9][c:8]2[c:20]([cH:19]1)[C:2]([CH3:1])([CH3:3])[O:4][C:5](=[O:6])[NH:7]2.Br[c:12]1[cH:13][cH:14][c:15]([C:16]#[N:17])[o:18]1>>[CH3:1][C:2]1([CH3:3])[O:4][C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][c:15]([C:16]#[N:17])[o:18]3)[cH:19][c:20]21 | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.N#Cc1ccc(Br)o1 | CC1(C)OC(=O)Nc2ccc(-c3ccc(C#N)o3)cc21 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 4f7d7b24f806b5cd4e85a32312d9881a35e9e6beb03f90f98c00ef7f864a3ecf | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Nc2ccc(-c3ccco3)cc2CO1 | Br-[c;H0;D3;+0:1]1:[#8;a:2]:[c:3]:[c:4]:[c:5]:1.O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:10]:[c:9]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1]1:[#8;a:2]:[c:3]:[c:4]:[c:5]:1):[c:7]:[c:8] | null | [] | null | null | null | null | 5-(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)-furan-2-carbonitrile was prepared, according to the procedure of Example 5 from 2-bromo-5-cyanofuran (1.0 g, 5.6 mmol) (J. Med. Chem. (1997), 40(23), 3804–3819) and (1,4-dihydro-4,4-dimethyl-2-oxo-2H-3,1-benzoxazin-6-yl)boronic acid (1.8 g, 8.18 mmol), as a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)COCN2.c1ccoc1 | c1ccc2c(c1)COCN2.c1ccoc1 | c1ccc2c(c1)COCN2.c1ccoc1 | HBr.B | null | null | null | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.N#Cc1ccc(Br)o1>>CC1(C)OC(=O)Nc2ccc(-c3ccc(C#N)o3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0c428ae268674c619645cd09cab52c13 | CCC1(CC)OC(=O)Nc2ccc(I)cc21.O=[N+]([O-])c1cccc(B(O)O)c1>>CCC1(CC)OC(=O)Nc2ccc(-c3cccc([N+](=O)[O-])c3)cc21 | C(C)C1(C2=C(NC(O1)=O)C=CC(=C2)I)CC.[N+](=O)([O-])C=1C=C(C=CC1)B(O)O>>C(C)C1(C2=C(NC(O1)=O)C=CC(=C2)C2=CC(=CC=C2)[N+](=O)[O-])CC | I[c:13]1[cH:12][cH:11][c:10]2[c:24]([cH:23]1)[C:3]([CH2:2][CH3:1])([CH2:4][CH3:5])[O:6][C:7](=[O:8])[NH:9]2.OB(O)[c:14]1[cH:15][cH:16][cH:17][c:18]([N+:19](=[O:20])[O-:21])[cH:22]1>>[CH3:1][CH2:2][C:3]1([CH2:4][CH3:5])[O:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][c:13](-[c:14]3[cH:15][cH:16][cH:17][c:18]([N+:19](=[O:20... | CCC1(CC)OC(=O)Nc2ccc(I)cc21.O=[N+]([O-])c1cccc(B(O)O)c1 | CCC1(CC)OC(=O)Nc2ccc(-c3cccc([N+](=O)[O-])c3)cc21 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 0fa2a30709dcd56081dfd73304ec3a2ee5346cb80b80e4b5dc426c319dd3d4bb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Nc2ccc(-c3ccccc3)cc2CO1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | null | [] | null | null | null | null | 4,4-Diethyl-6-(3-nitrophenyl)-1,4-dihydrobenzo[d][1,3]oxazin-2-one was prepared, from 4,4-diethyl-6-iodo-1,4-dihydrobenzo[d][1,3]oxazin-2-one and 3-nitrophenyl boronic acid according to the procedure of Example 4, as an off-white solid: mp 193–194° C.; 1H-NMR (CDCl3) δ 9.19 (s, 1H, D2O exchangeable), 8.38 (t, 1H, J=1.9... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)COCN2.c1ccccc1 | c1ccc2c(c1)COCN2.c1ccccc1 | c1ccc2c(c1)COCN2.c1ccccc1 | HI.B | null | null | null | CCC1(CC)OC(=O)Nc2ccc(I)cc21.O=[N+]([O-])c1cccc(B(O)O)c1>>CCC1(CC)OC(=O)Nc2ccc(-c3cccc([N+](=O)[O-])c3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6ff33a7f98944b36839c5de267a2d46a | CON(C)C(=O)c1cc(Br)ccc1N.OB(O)c1cccc(Cl)c1>>CON(C)C(=O)c1cccc(-c2cccc(Cl)c2)c1 | NC1=C(C(=O)N(C)OC)C=C(C=C1)Br.ClC=1C=C(C=CC1)B(O)O.C([O-])([O-])=O.[Na+].[Na+]>>ClC=1C=C(C=CC1)C=1C=CC=C(C(=O)N(C)OC)C1 | N[c:8]1[c:7]([C:5]([N:3]([O:2][CH3:1])[CH3:4])=[O:6])[cH:19][c:11](Br)[cH:10][cH:9]1.OB(O)[c:12]1[cH:13][cH:14][cH:15][c:16]([Cl:17])[cH:18]1>>[CH3:1][O:2][N:3]([CH3:4])[C:5](=[O:6])[c:7]1[cH:8][cH:9][cH:10][c:11](-[c:12]2[cH:13][cH:14][cH:15][c:16]([Cl:17])[cH:18]2)[cH:19]1 | CON(C)C(=O)c1cc(Br)ccc1N.OB(O)c1cccc(Cl)c1 | CON(C)C(=O)c1cccc(-c2cccc(Cl)c2)c1 | 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 | O.COCCOC | C-C Coupling | OtherReaction | 935af4259c4975cac487da8e9b2dade0b8df326796e05a95adf1d4d492f1807a | 79fc43732b29814f22dd0a7cbc24a0ef705cb8e808911cfb2a64a2630fa44903 | c1ccc(-c2ccccc2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c;H0;D3;+0:4](-N):[c:5](-[C:6](=[O;D1;H0:7])-[#7:8](-[#8:9])-[C;D1;H3:10]):[c:11]:1.O-B(-O)-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[#8:9]-[#7:8](-[C;D1;H3:10])-[C:6](=[O;D1;H0:7])-[c:5]1:[c:11]:[c;H0;D3;+0:1](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]):[c:2]:[c:3]:[cH;D2;+0:4... | 60.4 | [{"value": 57.0, "product": "ClC=1C=C(C=CC1)C=1C=CC=C(C(=O)N(C)OC)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.4, "product": "ClC=1C=C(C=CC1)C=1C=CC=C(C(=O)N(C)OC)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | null | null | A mixture of 2-amino-5-bromo-N-methoxy-N-methylbenzamide (7.78 g, 30 mmol), 3-chlorophenyl boronic acid (5.63 g, 36 mmol), tetrakis(triphenylphosphine)palladium (0) (1.73 g, 1.5 mmol), and sodium carbonate (7.63 g, 72 mmol) in a mixture of DME and water (150 mL/30 mL) was degassed to remove the oxygen and heated at 85°... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | HBr.B | 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.O.COCCOC | 85 | null | CON(C)C(=O)c1cc(Br)ccc1N.OB(O)c1cccc(Cl)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.O.COCCOC>CON(C)C(=O)c1cccc(-c2cccc(Cl)c2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-eb2f155c4449479dbc7f4fd79ec84839 | CON(C)C(=O)c1cccc(-c2cccc(Cl)c2)c1.[NH4+]>>CC(=O)c1cc(-c2cccc(Cl)c2)ccc1N | C(C)(=O)OCC.ClC=1C=C(C=CC1)C=1C=CC=C(C(=O)N(C)OC)C1.C[Li].[Cl-].[NH4+]>>NC1=C(C=C(C=C1)C1=CC(=CC=C1)Cl)C(C)=O | CON(C)[C:2](=[O:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][c:11]([Cl:12])[cH:13]2)[cH:14][cH:15][cH:16]1.[NH4+:17]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][c:11]([Cl:12])[cH:13]2)[cH:14][cH:15][c:16]1[NH2:17] | CON(C)C(=O)c1cccc(-c2cccc(Cl)c2)c1.[NH4+] | CC(=O)c1cc(-c2cccc(Cl)c2)ccc1N | null | null | CCOCC.C1CCOC1 | C-C Coupling | OtherReaction | d9e625bca5029b45899b727e5c506ae99b3f747ad8055f1c5fc71a14a0c85b03 | 2fbd26488ea02b131f565aa7b6fdcc6afd5764ffbfd21b2d786b3ac148ebc329 | c1ccc(-c2ccccc2)cc1 | C-O-N(-C)-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6]:[c:7].[NH4+;D0:8]>>[C;D1;H3:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c;H0;D3;+0:5](-[NH2;D1;+0:8]):[c:6]:[c:7] | 47 | [{"value": 47.0, "product": "NC1=C(C=C(C=C1)C1=CC(=CC=C1)Cl)C(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A mixture of 2-amino-5-bromo-N-methoxy-N-methylbenzamide (7.78 g, 30 mmol), 3-chlorophenyl boronic acid (5.63 g, 36 mmol), tetrakis(triphenylphosphine)palladium (0) (1.73 g, 1.5 mmol), and sodium carbonate (7.63 g, 72 mmol) in a mixture of DME and water (150 mL/30 mL) was degassed to remove the oxygen and heated at 85°... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Ketone.Primary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | CCOCC.C1CCOC1 | null | 0.5 | CON(C)C(=O)c1cccc(-c2cccc(Cl)c2)c1.[NH4+]>CCOCC.C1CCOC1>CC(=O)c1cc(-c2cccc(Cl)c2)ccc1N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-32cecf2ca50b4412a37e97546a0bac8c | CC(=O)c1cc(-c2cccc(Cl)c2)ccc1N.O=C(n1ccnc1)n1ccnc1.[Br][Mg][c]1ccccc1>>CC1(c2ccccc2)OC(=O)Nc2ccc(-c3cccc(Cl)c3)cc21 | C1CCOC1.NC1=C(C=C(C=C1)C1=CC(=CC=C1)Cl)C(C)=O.C1(=CC=CC=C1)[Mg]Br.C1=CN(C=N1)C(=O)N2C=CN=C2>>ClC=1C=C(C=CC1)C1=CC2=C(NC(OC2(C2=CC=CC=C2)C)=O)C=C1 | [CH3:1][C:2](=[O:9])[c:25]1[c:13]([NH2:12])[cH:14][cH:15][c:16](-[c:17]2[cH:18][cH:19][cH:20][c:21]([Cl:22])[cH:23]2)[cH:24]1.c1cn([C:10](n2ccnc2)=[O:11])cn1.[Br][Mg][c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1>>[CH3:1][C:2]1([c:3]2[cH:4][cH:5][cH:6][cH:7][cH:8]2)[O:9][C:10](=[O:11])[NH:12][c:13]2[cH:14][cH:15][c:16](-[c:17]3... | CC(=O)c1cc(-c2cccc(Cl)c2)ccc1N.O=C(n1ccnc1)n1ccnc1.[Br][Mg][c]1ccccc1 | CC1(c2ccccc2)OC(=O)Nc2ccc(-c3cccc(Cl)c3)cc21 | null | null | null | C-C Coupling | OtherReaction | f58a792c9a8544457dec510324c5228ba9ef6635800cdc56785c13deeccae300 | 90008ef043900bdf87d9d5fd1a862da1cc24a9fb439932e381713f7ba0baeb59 | O=C1Nc2ccc(-c3ccccc3)cc2C(c2ccccc2)O1 | [Br]-[Mg]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-[c:9](:[c:10]):[c:11](-[NH2;D1;+0:12]):[c:13].[O;D1;H0:14]=[C;H0;D3;+0:15](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[C;D1;H3:6]-[C;H0;D4;+0:7]1(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[O;H0;D2;+0:8]-[C;H0;D3;+0:15](=[O;D1;H0:14])-[NH;... | null | [] | null | null | null | null | 6-(3-Chlorophenyl)-4-methyl-4-phenyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one was prepared, from 1-(4-amino-3′-chloro-biphenyl-3-yl)-ethanone (0.2 g, 0.82 mmol) and phenylmagnesium bromide followed by treatment with CDI in THF, as a white solid: mp 179–180° C.; 1H-NMR (CDCl3) δ 8.27 (s, 1H, D2O exchangeable), 7.51–7.57 (m... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Ketone.Primary amine | Carbamic ester.Ether | c1c[nH]cn1.c1c[nH]cn1.c1ccccc1 | c1ccccc1.c1ccc2c(c1)COCN2 | c1ccccc1.c1ccc2c(c1)COCN2.c1ccccc1 | HBr.Mg | null | null | null | CC(=O)c1cc(-c2cccc(Cl)c2)ccc1N.O=C(n1ccnc1)n1ccnc1.[Br][Mg][c]1ccccc1>>CC1(c2ccccc2)OC(=O)Nc2ccc(-c3cccc(Cl)c3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-80da410e3a34442a9c0e79cfc16cc22c | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.Fc1cc(F)cc(Br)c1>>CC1(C)OC(=O)Nc2ccc(-c3cc(F)cc(F)c3)cc21 | CC1(OC(NC2=C1C=C(C=C2)B(O)O)=O)C.BrC1=CC(=CC(=C1)F)F>>FC=1C=C(C=C(C1)F)C1=CC2=C(NC(OC2(C)C)=O)C=C1 | OB(O)[c:11]1[cH:10][cH:9][c:8]2[c:21]([cH:20]1)[C:2]([CH3:1])([CH3:3])[O:4][C:5](=[O:6])[NH:7]2.Br[c:12]1[cH:13][c:14]([F:15])[cH:16][c:17]([F:18])[cH:19]1>>[CH3:1][C:2]1([CH3:3])[O:4][C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][c:14]([F:15])[cH:16][c:17]([F:18])[cH:19]3)[cH:20][c:21]21 | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.Fc1cc(F)cc(Br)c1 | CC1(C)OC(=O)Nc2ccc(-c3cc(F)cc(F)c3)cc21 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 0fa2a30709dcd56081dfd73304ec3a2ee5346cb80b80e4b5dc426c319dd3d4bb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Nc2ccc(-c3ccccc3)cc2CO1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | null | [] | null | null | null | null | 6-(3,5-difluoro-phenyl)-4,4-dimethyl-1,4-dihydrobenzo-[d][1,3]oxazin-2-one was prepared, according to the procedure of Example 5 from (4,4-dimethyl-1,4-dihydro-2-oxo-2H-3,1-benzoxazin-6-yl)boronic acid and 1-bromo-3,5-difluorobenzene, as a white solid: mp 218–219° C.; 1H-NMR (DMSO-d6) δ 10.4 (s, 1H), 7.67–7.65 (m, 2H),... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)COCN2.c1ccccc1 | c1ccc2c(c1)COCN2.c1ccccc1 | c1ccc2c(c1)COCN2.c1ccccc1 | HBr.B | null | null | null | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.Fc1cc(F)cc(Br)c1>>CC1(C)OC(=O)Nc2ccc(-c3cc(F)cc(F)c3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-988638c796ae45c688be965cb9646779 | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.COCCOC>>COc1cc(C#N)cc(-c2ccc3c(c2)C(C)(C)OC(=O)N3)c1 | CC1(OC(NC2=C1C=C(C=C2)B(O)O)=O)C.C([O-])([O-])=O.[Na+].[Na+].[Br-].[Li+].O.COCCOC>>CC1(C2=C(NC(O1)=O)C=CC(=C2)C=2C=C(C#N)C=C(C2)OC)C | OB(O)[c:10]1[cH:11][cH:12][c:13]2[c:14]([cH:15]1)[C:16]([CH3:17])([CH3:18])[O:19][C:20](=[O:21])[NH:7]2.O([CH2:4][CH2:3][O:2][CH3:1])[CH3:5]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]#[N:7])[cH:8][c:9](-[c:10]2[cH:11][cH:12][c:13]3[c:14]([cH:15]2)[C:16]([CH3:17])([CH3:18])[O:19][C:20](=[O:21])[NH:22]3)[cH:23]1 | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.COCCOC | COc1cc(C#N)cc(-c2ccc3c(c2)C(C)(C)OC(=O)N3)c1 | null | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | C(C)(=O)OCC | Aromatic Heterocycle Formation | OtherReaction | 10a74f45bf132ebcc20e108a859f92b7de536fe3d7ed4fb13802789a8f67edab | 4216aae7036d4a7562fc0c1d39526975f9f6c0c8a2f5f093a06ee9e8e2e4ca8a | O=C1Nc2ccc(-c3ccccc3)cc2CO1 | O-B(-O)-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c;H0;D3;+0:4]2:[c:5](:[c:6]:1)-[C:7]-[#8:8]-[C;H0;D3;+0:9](=[O;D1;H0:10])-[NH;D2;+0:11]-2.[C;D1;H3:12]-[#8:13]-[CH2;D2;+0:14]-[CH2;D2;+0:15]-O-[CH3;D1;+0:16]>>[C;D1;H3:12]-[#8:13]-[c;H0;D3;+0:14]1:[c:17]:[c:18](-[c;H0;D3;+0:1]2:[c:2]:[c:3]:[c;H0;D3;+0:4]3:[c:5](:[c:6]:2)-[C:7]-[#8:8... | 53 | [{"value": 53.0, "product": "CC1(C2=C(NC(O1)=O)C=CC(=C2)C=2C=C(C#N)C=C(C2)OC)C", "details": "PERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 15 | MINUTE | A mixture of (4,4-dimethyl-1,4-dihydro-2-oxo-2H-3,1-benzoxazin-6-yl)boronic acid (4.2 g, 19.0 mmol), 3-cyano-5-methoxybenzyltriflate (5.1 g, 19.0 mmol), tetrakis(triphenylphosphine)-palladium (0) (1.1 g, 0.95 mmol), sodium carbonate (4.0 g, 38.0 mmol), lithium bromide (5 g, 57 mmol) in DME (50 mL), and water (25 mL) un... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether.Ether.Boronic acid | Carbamic ester.Ether.Ether.Nitrile | c1ccc2c(c1)COCN2 | c1ccccc1.c1ccc2c(c1)COCN2 | c1ccccc1.c1ccc2c(c1)COCN2 | HO-.B | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)(=O)OCC | 50 | 0.25 | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.COCCOC>[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)(=O)OCC>COc1cc(C#N)cc(-c2ccc3c(c2)C(C)(C)OC(=O)N3)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b819503bde5e4c3ba949b637dda5ae03 | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.Fc1ccc(Br)cc1>>CC1(C)OC(=O)Nc2ccc(-c3ccc(F)cc3)cc21 | CC1(OC(NC2=C1C=C(C=C2)B(O)O)=O)C.BrC1=CC=C(C=C1)F>>FC1=CC=C(C=C1)C1=CC2=C(NC(OC2(C)C)=O)C=C1 | OB(O)[c:11]1[cH:10][cH:9][c:8]2[c:20]([cH:19]1)[C:2]([CH3:1])([CH3:3])[O:4][C:5](=[O:6])[NH:7]2.Br[c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1>>[CH3:1][C:2]1([CH3:3])[O:4][C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]3)[cH:19][c:20]21 | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.Fc1ccc(Br)cc1 | CC1(C)OC(=O)Nc2ccc(-c3ccc(F)cc3)cc21 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 0fa2a30709dcd56081dfd73304ec3a2ee5346cb80b80e4b5dc426c319dd3d4bb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Nc2ccc(-c3ccccc3)cc2CO1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | null | [] | null | null | null | null | 6-(4-Fluoro-phenyl)-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one was prepared, according to the procedure of Example 5 from (1,4-dihydro-4,4-dimethyl-2-oxo-2H-3,1-benzoxazin-6-yl)boronic acid and 1-bromo-4-fluorobenzene, as off-white crystals: mp 232–233° C.; 1H-NMR (DMSO-d6) δ 10.3 (s, 1H), 7.74 (m, 2H), 7.53 (m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)COCN2.c1ccccc1 | c1ccc2c(c1)COCN2.c1ccccc1 | c1ccc2c(c1)COCN2.c1ccccc1 | HBr.B | null | null | null | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.Fc1ccc(Br)cc1>>CC1(C)OC(=O)Nc2ccc(-c3ccc(F)cc3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8e8a22badc9e48b6b9e6dfca240a57f8 | BrBr.CC1(C)OC(=O)Nc2ccc(-c3cc(F)cc(C#N)c3)cc21>>CC1(C)OC(=O)Nc2c(Br)cc(-c3cc(F)cc(C#N)c3)cc21 | CC1(OC(NC2=C1C=C(C=C2)C=2C=C(C#N)C=C(C2)F)=O)C.C(C)(=O)[O-].[Na+].BrBr>>BrC1=CC(=CC=2C(OC(NC21)=O)(C)C)C=2C=C(C#N)C=C(C2)F | Br[Br:10].[CH3:1][C:2]1([CH3:3])[O:4][C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:11][c:12](-[c:13]3[cH:14][c:15]([F:16])[cH:17][c:18]([C:19]#[N:20])[cH:21]3)[cH:22][c:23]21>>[CH3:1][C:2]1([CH3:3])[O:4][C:5](=[O:6])[NH:7][c:8]2[c:9]([Br:10])[cH:11][c:12](-[c:13]3[cH:14][c:15]([F:16])[cH:17][c:18]([C:19]#[N:20])[cH:21]3)[cH:22][c... | BrBr.CC1(C)OC(=O)Nc2ccc(-c3cc(F)cc(C#N)c3)cc21 | CC1(C)OC(=O)Nc2c(Br)cc(-c3cc(F)cc(C#N)c3)cc21 | null | null | C(C)(=O)O | Functional Group Interconversion | Bromination | f2e1e2237cf85b69b6ca775a9b733eae7076a772fd87c1b40b984f4a2e0b36b9 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | O=C1Nc2ccc(-c3ccccc3)cc2CO1 | Br-[Br;H0;D1;+0:1].[#8:2]-[C:3](=[O;D1;H0:4])-[#7:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10]>>[#8:2]-[C:3](=[O;D1;H0:4])-[#7:5]-[c:6](:[c:7]):[c;H0;D3;+0:8](-[Br;H0;D1;+0:1]):[c:9]:[c:10] | 75.3 | [{"value": 75.0, "product": "BrC1=CC(=CC=2C(OC(NC21)=O)(C)C)C=2C=C(C#N)C=C(C2)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.3, "product": "BrC1=CC(=CC=2C(OC(NC21)=O)(C)C)C=2C=C(C#N)C=C(C2)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | To a mixture of 3-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-5-fluorobenzonitrile (0.5 g, 1.7 mmol) and sodium acetate (0.2 g, 2.4 mmol) in acetic acid (5 mL) was added, at room temperature under nitrogen, bromine (0.12 mL, 2.34 mmol). The reaction mixture was stirred for 20 hours and then poured into ice ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2c(c1)COCN2 | c1ccc2c(c1)COCN2 | c1ccc2c(c1)COCN2.c1ccccc1 | HBr | C(C)(=O)O | null | 20 | BrBr.CC1(C)OC(=O)Nc2ccc(-c3cc(F)cc(C#N)c3)cc21>C(C)(=O)O>CC1(C)OC(=O)Nc2c(Br)cc(-c3cc(F)cc(C#N)c3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-909192587b9c42d1b2da4b6286c124d2 | CC1(C)OC(=O)Nc2ccc(I)cc21.O=[N+]([O-])c1cccc(B(O)O)c1>>CC1(C)OC(=O)Nc2ccc(-c3cccc([N+](=O)[O-])c3)cc21 | IC1=CC2=C(NC(OC2(C)C)=O)C=C1.[N+](=O)([O-])C=1C=C(C=CC1)B(O)O>>CC1(C2=C(NC(O1)=O)C=CC(=C2)C2=CC(=CC=C2)[N+](=O)[O-])C | I[c:11]1[cH:10][cH:9][c:8]2[c:22]([cH:21]1)[C:2]([CH3:1])([CH3:3])[O:4][C:5](=[O:6])[NH:7]2.OB(O)[c:12]1[cH:13][cH:14][cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20]1>>[CH3:1][C:2]1([CH3:3])[O:4][C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20]3)[cH:21][c:22]... | CC1(C)OC(=O)Nc2ccc(I)cc21.O=[N+]([O-])c1cccc(B(O)O)c1 | CC1(C)OC(=O)Nc2ccc(-c3cccc([N+](=O)[O-])c3)cc21 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 0fa2a30709dcd56081dfd73304ec3a2ee5346cb80b80e4b5dc426c319dd3d4bb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Nc2ccc(-c3ccccc3)cc2CO1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9]:[c:10] | null | [] | null | null | null | null | 4,4-Dimethyl-6-(3-nitrophenyl)-1,4-dihydro benzo[d][1,3]oxazin-2-one was prepared, from 6-iodo-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one and 3-nitrophenyl boronic acid according to the procedure of Example 4, as a yellowish solid: mp 244–245° C.; 1H-NMR (DMSO-d6) δ 10.38 (s, 1H, D2O exchangeable), 8.47 (s, 1H)... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)COCN2.c1ccccc1 | c1ccc2c(c1)COCN2.c1ccccc1 | c1ccc2c(c1)COCN2.c1ccccc1 | HI.B | null | null | null | CC1(C)OC(=O)Nc2ccc(I)cc21.O=[N+]([O-])c1cccc(B(O)O)c1>>CC1(C)OC(=O)Nc2ccc(-c3cccc([N+](=O)[O-])c3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-71980f2d95324af0b9651afab633a64f | CCC1(CC)OC(=O)Nc2ccc(I)cc21.OB(O)c1cccc(Cl)c1>>CCC1(CC)OC(=O)Nc2ccc(-c3cccc(Cl)c3)cc21 | C(C)C1(C2=C(NC(O1)=O)C=CC(=C2)I)CC.ClC=1C=C(C=CC1)B(O)O>>ClC=1C=C(C=CC1)C1=CC2=C(NC(OC2(CC)CC)=O)C=C1 | I[c:13]1[cH:12][cH:11][c:10]2[c:22]([cH:21]1)[C:3]([CH2:2][CH3:1])([CH2:4][CH3:5])[O:6][C:7](=[O:8])[NH:9]2.OB(O)[c:14]1[cH:15][cH:16][cH:17][c:18]([Cl:19])[cH:20]1>>[CH3:1][CH2:2][C:3]1([CH2:4][CH3:5])[O:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][c:13](-[c:14]3[cH:15][cH:16][cH:17][c:18]([Cl:19])[cH:20]3)[cH:21][c:22]... | CCC1(CC)OC(=O)Nc2ccc(I)cc21.OB(O)c1cccc(Cl)c1 | CCC1(CC)OC(=O)Nc2ccc(-c3cccc(Cl)c3)cc21 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 0fa2a30709dcd56081dfd73304ec3a2ee5346cb80b80e4b5dc426c319dd3d4bb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Nc2ccc(-c3ccccc3)cc2CO1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | null | [] | null | null | null | null | 6-(3-Chlorophenyl)-4,4-diethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one was prepared, from 4,4-diethyl-6-iodo-1,4-dihydrobenzo[d][1,3]oxazin-2-one and 3-chlorophenyl boronic acid according to the procedure of Example 4, as a white solid: mp 150–151° C.; 1H-NMR (CDCl3) δ 8.52 (s, 1H, D2O exchangeable), 7.50 (s, 1H), 7.31–7.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)COCN2.c1ccccc1 | c1ccc2c(c1)COCN2.c1ccccc1 | c1ccc2c(c1)COCN2.c1ccccc1 | HI.B | null | null | null | CCC1(CC)OC(=O)Nc2ccc(I)cc21.OB(O)c1cccc(Cl)c1>>CCC1(CC)OC(=O)Nc2ccc(-c3cccc(Cl)c3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cea597d3cda242f9a4a8bf5ab53a4814 | CC1(C)OC(=O)Nc2ccc(Br)cc21.COc1cccc(B(O)O)c1>>COc1cccc(-c2ccc3c(c2)C(C)(C)OC(=O)N3)c1 | BrC1=CC2=C(NC(OC2(C)C)=O)C=C1.COC=1C=C(C=CC1)B(O)O>>COC=1C=C(C=CC1)C1=CC2=C(NC(OC2(C)C)=O)C=C1 | Br[c:8]1[cH:9][cH:10][c:11]2[c:12]([cH:13]1)[C:14]([CH3:15])([CH3:16])[O:17][C:18](=[O:19])[NH:20]2.OB(O)[c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:21]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]3[c:12]([cH:13]2)[C:14]([CH3:15])([CH3:16])[O:17][C:18](=[O:19])[NH:20]3)[cH:21]1 | CC1(C)OC(=O)Nc2ccc(Br)cc21.COc1cccc(B(O)O)c1 | COc1cccc(-c2ccc3c(c2)C(C)(C)OC(=O)N3)c1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 0fa2a30709dcd56081dfd73304ec3a2ee5346cb80b80e4b5dc426c319dd3d4bb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Nc2ccc(-c3ccccc3)cc2CO1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:2]:[c:3] | null | [] | null | null | null | null | 6-(3-Methoxy-phenyl)-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one was prepared, according to the procedure of Example 4 from 6-bromo-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one and 3-methoxyphenyl boronic acid, as a yellow solid: mp 164–165° C.; 1H-NMR (DMSO-d6) δ 10.3 (s, 1H), 7.56 (m, 2H), 7.36 (t, 1H, J... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)COCN2.c1ccccc1 | c1ccccc1.c1ccc2c(c1)COCN2 | c1ccccc1.c1ccc2c(c1)COCN2 | HBr.B | null | null | null | CC1(C)OC(=O)Nc2ccc(Br)cc21.COc1cccc(B(O)O)c1>>COc1cccc(-c2ccc3c(c2)C(C)(C)OC(=O)N3)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c65c670bafc04607af088527d5e2523f | CC1(C)OC(=O)Nc2ccc(Br)cc21.OB(O)c1ccccc1Cl>>CC1(C)OC(=O)Nc2ccc(-c3ccccc3Cl)cc21 | BrC1=CC2=C(NC(OC2(C)C)=O)C=C1.ClC1=C(C=CC=C1)B(O)O>>ClC1=C(C=CC=C1)C1=CC2=C(NC(OC2(C)C)=O)C=C1 | Br[c:11]1[cH:10][cH:9][c:8]2[c:20]([cH:19]1)[C:2]([CH3:1])([CH3:3])[O:4][C:5](=[O:6])[NH:7]2.OB(O)[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[Cl:18]>>[CH3:1][C:2]1([CH3:3])[O:4][C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[Cl:18])[cH:19][c:20]21 | CC1(C)OC(=O)Nc2ccc(Br)cc21.OB(O)c1ccccc1Cl | CC1(C)OC(=O)Nc2ccc(-c3ccccc3Cl)cc21 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 0fa2a30709dcd56081dfd73304ec3a2ee5346cb80b80e4b5dc426c319dd3d4bb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Nc2ccc(-c3ccccc3)cc2CO1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[Cl;D1;H0:10]):[c:11]>>[Cl;D1;H0:10]-[c:9](:[c:11]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | null | [] | null | null | null | null | 6-(2-Chloro-phenyl)-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one was prepared, according to the procedure of Example 4 from 6-bromo-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one and 2-chlorophenyl boronic acid, as a white solid: mp 181–182° C.; MS (ESI) m/z 288 ([M+H]+, 70%); Anal. Calc. For C16H14ClNO2: C, ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)COCN2.c1ccccc1 | c1ccc2c(c1)COCN2.c1ccccc1 | c1ccc2c(c1)COCN2.c1ccccc1 | HBr.B | null | null | null | CC1(C)OC(=O)Nc2ccc(Br)cc21.OB(O)c1ccccc1Cl>>CC1(C)OC(=O)Nc2ccc(-c3ccccc3Cl)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ae820404baa34a94b4d3ec0b616c8986 | CC(O)(Cc1ccccc1)c1cc(-c2cccc(Cl)c2)ccc1N.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>>CC1(Cc2ccccc2)OC(=O)Nc2ccc(-c3cccc(Cl)c3)cc21 | NC1=C(C=C(C=C1)C1=CC(=CC=C1)Cl)C(C)(O)CC1=CC=CC=C1.NC1=C(C=C(C=C1)C1=CC(=CC=C1)Cl)C(C)=O.C(C1=CC=CC=C1)[Mg]Br.ClC(Cl)(OC(OC(Cl)(Cl)Cl)=O)Cl>>C(C1=CC=CC=C1)C1(C2=C(NC(O1)=O)C=CC(=C2)C2=CC(=CC=C2)Cl)C | [CH3:1][C:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)([OH:10])[c:26]1[c:14]([NH2:13])[cH:15][cH:16][c:17](-[c:18]2[cH:19][cH:20][cH:21][c:22]([Cl:23])[cH:24]2)[cH:25]1.ClC(Cl)(Cl)O[C:11](OC(Cl)(Cl)Cl)=[O:12]>>[CH3:1][C:2]1([CH2:3][c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)[O:10][C:11](=[O:12])[NH:13][c:14]2[cH:15][cH:1... | CC(O)(Cc1ccccc1)c1cc(-c2cccc(Cl)c2)ccc1N.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl | CC1(Cc2ccccc2)OC(=O)Nc2ccc(-c3cccc(Cl)c3)cc21 | null | null | C1CCOC1 | Protection | OtherReaction | 2aea0be1056e79f2bca707804aa8e85c0a3e7237a1d4596f980bbb552d0f903a | 5281b9a3f1004ab22b65d22fa67f63481ebe385cacff32b87d9504f5f5492462 | O=C1Nc2ccc(-c3ccccc3)cc2C(Cc2ccccc2)O1 | Cl-C(-Cl)(-Cl)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-C(-Cl)(-Cl)-Cl.[C:3]-[C:4](-[C;D1;H3:5])(-[OH;D1;+0:6])-[c:7]:[c:8](-[NH2;D1;+0:9]):[c:10]>>[C:3]-[C:4]1(-[C;D1;H3:5])-[O;H0;D2;+0:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:9]-[c:8](:[c:10]):[c:7]-1 | 30 | [{"value": 30.0, "product": "C(C1=CC=CC=C1)C1(C2=C(NC(O1)=O)C=CC(=C2)C2=CC(=CC=C2)Cl)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1-(4-amino-3′-chloro-biphenyl-3-yl)-1-benzyl-ethanol (prepared from 1-(4-amino-3′-chloro-biphenyl-3-yl)-ethanone and benzylmagnesium bromide according to procedure described previously, 0.14 g, 0.42 mmol) and triphosgene (0.04 g, 0.14 mmol) in dry THF (10 mL) was stirred under a blanket of nitrogen for 10 ... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Trichloro group.Carbonic Ester.Tertiary alcohol.Primary amine | Carbamic ester | null | c1ccc2c(c1)COCN2 | c1ccccc1.c1ccc2c(c1)COCN2.c1ccccc1 | HCl | C1CCOC1 | null | null | CC(O)(Cc1ccccc1)c1cc(-c2cccc(Cl)c2)ccc1N.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>C1CCOC1>CC1(Cc2ccccc2)OC(=O)Nc2ccc(-c3cccc(Cl)c3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1e7f65f8f38f4adfa5c342fff0841462 | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.Fc1cc(Br)cc(Br)c1>>CC1(C)OC(=O)Nc2ccc(-c3cc(F)cc(Br)c3)cc21 | CC1(OC(NC2=C1C=C(C=C2)B(O)O)=O)C.BrC1=CC(=CC(=C1)F)Br>>BrC=1C=C(C=C(C1)F)C1=CC2=C(NC(OC2(C)C)=O)C=C1 | OB(O)[c:11]1[cH:10][cH:9][c:8]2[c:21]([cH:20]1)[C:2]([CH3:1])([CH3:3])[O:4][C:5](=[O:6])[NH:7]2.Br[c:12]1[cH:13][c:14]([F:15])[cH:16][c:17]([Br:18])[cH:19]1>>[CH3:1][C:2]1([CH3:3])[O:4][C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][c:14]([F:15])[cH:16][c:17]([Br:18])[cH:19]3)[cH:20][c:21]21 | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.Fc1cc(Br)cc(Br)c1 | CC1(C)OC(=O)Nc2ccc(-c3cc(F)cc(Br)c3)cc21 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 0fa2a30709dcd56081dfd73304ec3a2ee5346cb80b80e4b5dc426c319dd3d4bb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Nc2ccc(-c3ccccc3)cc2CO1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | null | [] | null | null | null | null | 6-(3-Bromo-5-fluorophenyl)-4,4-dimethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one was prepared, from (1,4-dihydro-4,4-dimethyl-2-oxo-2H-3,1-benzoxazin-6-yl)boronic acid and 1,3-dibromo-5-fluorobenzene following the procedure of Example 5, as a white solid: mp 182–183° C.; 1H-NMR (DMSO-d6) δ 10.36 (s, 1H, D2O exchangeable), ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)COCN2.c1ccccc1 | c1ccc2c(c1)COCN2.c1ccccc1 | c1ccc2c(c1)COCN2.c1ccccc1 | HBr.B | null | null | null | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.Fc1cc(Br)cc(Br)c1>>CC1(C)OC(=O)Nc2ccc(-c3cc(F)cc(Br)c3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fe65bebe1e3a4f72a7a1f4060882e9df | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.N#Cc1ccc(Br)s1>>CC1(C)OC(=O)Nc2ccc(-c3ccc(C#N)s3)cc21 | BrC1=CC=C(S1)C#N.CC1(OC(NC2=C1C=C(C=C2)B(O)O)=O)C>>CC1(C2=C(NC(O1)=O)C=CC(=C2)C2=CC=C(S2)C#N)C | OB(O)[c:11]1[cH:10][cH:9][c:8]2[c:20]([cH:19]1)[C:2]([CH3:1])([CH3:3])[O:4][C:5](=[O:6])[NH:7]2.Br[c:12]1[cH:13][cH:14][c:15]([C:16]#[N:17])[s:18]1>>[CH3:1][C:2]1([CH3:3])[O:4][C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][c:15]([C:16]#[N:17])[s:18]3)[cH:19][c:20]21 | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.N#Cc1ccc(Br)s1 | CC1(C)OC(=O)Nc2ccc(-c3ccc(C#N)s3)cc21 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 0b5bebfae8e49ed7172cda779db0d9a1ee34897b702e6169adb1825468a1d911 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Nc2ccc(-c3cccs3)cc2CO1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1.O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:10]:[c:9]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1):[c:7]:[c:8] | null | [] | null | null | null | null | 5-(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)-thiophene-2-carbonitrile was prepared, according to the procedure of Example 5 using 5-bromo-2-thiophenecarbonitrile and (1,4-dihydro-4,4-dimethyl-2-oxo-2H-3,1-benzoxazin-6-yl)boronic acid, as an off-white solid: mp 264–266° C.; 1H-NMR (DMSO-d6) δ 10.3 (s, ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)COCN2.c1ccsc1 | c1ccc2c(c1)COCN2.c1ccsc1 | c1ccc2c(c1)COCN2.c1ccsc1 | HBr.B | null | null | null | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.N#Cc1ccc(Br)s1>>CC1(C)OC(=O)Nc2ccc(-c3ccc(C#N)s3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fb8a7cb9b84a4ed1948475ce66754281 | CC1(C)OC(=O)Nc2ccc(Br)cc21.Fc1ccc(Br)cc1Cl>>CC1(C)OC(=O)Nc2ccc(-c3ccc(F)c(Cl)c3)cc21 | BrC1=CC2=C(NC(OC2(C)C)=O)C=C1.BrC1=CC(=C(C=C1)F)Cl>>ClC=1C=C(C=CC1F)C1=CC2=C(NC(OC2(C)C)=O)C=C1 | Br[c:11]1[cH:10][cH:9][c:8]2[c:21]([cH:20]1)[C:2]([CH3:1])([CH3:3])[O:4][C:5](=[O:6])[NH:7]2.Br[c:12]1[cH:13][cH:14][c:15]([F:16])[c:17]([Cl:18])[cH:19]1>>[CH3:1][C:2]1([CH3:3])[O:4][C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][c:15]([F:16])[c:17]([Cl:18])[cH:19]3)[cH:20][c:21]21 | CC1(C)OC(=O)Nc2ccc(Br)cc21.Fc1ccc(Br)cc1Cl | CC1(C)OC(=O)Nc2ccc(-c3ccc(F)c(Cl)c3)cc21 | null | null | null | C-C Coupling | Negishi | 98598d81856d2c897d85eeb92f31247576a7bcf3cc7c3b939bc0c81fa93e6b1e | a7a4ce9a92e2f8a62d28956a69a5cc384426ab72416e87d68c6a3feb23c22d66 | O=C1Nc2ccc(-c3ccccc3)cc2CO1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].Br-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9]:[c:10] | null | [] | null | null | null | null | 6-(3-Chloro-4-fluoro-phenyl)-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one was prepared, from 6-bromo-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one and 1-bromo-3-chloro-4-fluorobenzene according to Procedure A, as a white solid: mp 211–212° C.; 1H-NMR (DMSO-d6) δ 10.4 (s, 1H), 7.92 (dd, 1H, J=7.13, 2.19 Hz), ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide | null | c1ccc2c(c1)COCN2.c1ccccc1 | c1ccc2c(c1)COCN2.c1ccccc1 | c1ccc2c(c1)COCN2.c1ccccc1 | Br- | null | null | null | CC1(C)OC(=O)Nc2ccc(Br)cc21.Fc1ccc(Br)cc1Cl>>CC1(C)OC(=O)Nc2ccc(-c3ccc(F)c(Cl)c3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d8a65d0330024d84bd2d3d89dfe8eeca | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.N#Cc1cc(Br)co1>>CC1(C)OC(=O)Nc2ccc(-c3coc(C#N)c3)cc21 | CC1(OC(NC2=C1C=C(C=C2)B(O)O)=O)C.BrC=1C=C(OC1)C#N>>CC1(C2=C(NC(O1)=O)C=CC(=C2)C=2C=C(OC2)C#N)C | OB(O)[c:11]1[cH:10][cH:9][c:8]2[c:20]([cH:19]1)[C:2]([CH3:1])([CH3:3])[O:4][C:5](=[O:6])[NH:7]2.Br[c:12]1[cH:13][o:14][c:15]([C:16]#[N:17])[cH:18]1>>[CH3:1][C:2]1([CH3:3])[O:4][C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][o:14][c:15]([C:16]#[N:17])[cH:18]3)[cH:19][c:20]21 | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.N#Cc1cc(Br)co1 | CC1(C)OC(=O)Nc2ccc(-c3coc(C#N)c3)cc21 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 4f7d7b24f806b5cd4e85a32312d9881a35e9e6beb03f90f98c00ef7f864a3ecf | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1Nc2ccc(-c3ccoc3)cc2CO1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#8;a:3]:[c:4](-[C:5]#[N;D1;H0:6]):[c:7]:1.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[N;D1;H0:6]#[C:5]-[c:4]1:[#8;a:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:7]:1 | null | [] | null | null | null | null | 4-(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)-furan-2-carbonitrile was prepared from (1,4-dihydro-4,4-dimethyl-2-oxo-2H-3,1-benzoxazin-6-yl)boronic acid and 4-bromo-2-furancarbonitrile according to Procedure B. Off-white solid: mp 255–256° C. 1H-NMR (DMSO-d6) δ 10.32 (s, 1H, D2O exchangeable), 8.57 (s,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)COCN2.c1ccoc1 | c1ccc2c(c1)COCN2.c1ccoc1 | c1ccc2c(c1)COCN2.c1ccoc1 | HBr.B | null | null | null | CC1(C)OC(=O)Nc2ccc(B(O)O)cc21.N#Cc1cc(Br)co1>>CC1(C)OC(=O)Nc2ccc(-c3coc(C#N)c3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6d8f6eefee55419da012d50fe760f6de | CC1(C)OC(=O)Nc2ccc(-c3cccc(Br)c3)cc21.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1>>CC1(C)OC(=S)Nc2ccc(-c3cccc(Br)c3)cc21 | BrC=1C=C(C=CC1)C1=CC2=C(NC(OC2(C)C)=O)C=C1.COC=1C=CC(=CC1)P2(=S)SP(=S)(S2)C=3C=CC(=CC3)OC>>BrC=1C=C(C=CC1)C=1C=CC2=C(C(OC(N2)=S)(C)C)C1 | O=[C:5]1[O:4][C:2]([CH3:1])([CH3:3])[c:20]2[c:8]([cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][c:16]([Br:17])[cH:18]3)[cH:19]2)[NH:7]1.COc1ccc(P2(=S)SP(c3ccc(OC)cc3)(=[S:6])S2)cc1>>[CH3:1][C:2]1([CH3:3])[O:4][C:5](=[S:6])[NH:7][c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][c:16]([Br:17])[cH:18]3)[cH:19][c:... | CC1(C)OC(=O)Nc2ccc(-c3cccc(Br)c3)cc21.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1 | CC1(C)OC(=S)Nc2ccc(-c3cccc(Br)c3)cc21 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 97d5668e697b90041eba9dad68ad83f7a1cdfe0944b559f928d28ab2564e8d10 | c331ef400a59f343eb23abd2f965cf1719390c2753d5de53af30054e75d29d94 | S=C1Nc2ccc(-c3ccccc3)cc2CO1 | C-O-c1:c:c:c(-P2(=S)-S-P(=[S;H0;D1;+0:1])(-c3:c:c:c(-O-C):c:c:3)-S-2):c:c:1.O=[C;H0;D3;+0:2](-[#7:3]-[c:4])-[#8:5]-[C:6]>>[C:6]-[#8:5]-[C;H0;D3;+0:2](=[S;H0;D1;+0:1])-[#7:3]-[c:4] | 122.9 | [{"value": 61.0, "product": "BrC=1C=C(C=CC1)C=1C=CC2=C(C(OC(N2)=S)(C)C)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 122.9, "product": "BrC=1C=C(C=CC1)C=1C=CC2=C(C(OC(N2)=S)(C)C)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | null | null | A mixture of 6-(3-bromo-phenyl)-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one (3 g, 9.04 mmol) and Lawesson's Reagent (1.83 g, 4.51 mmol) in toluene (30 mL) was heated to 110° C. for 24 hours. The reaction was cooled, the toluene removed in vacuo and the residue purified via flash chromatography (silica gel, 20% e... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether.Ether.Monosulfide.Monosulfide | Ether.Thioamide | c1ccc2c(c1)COCN2.c1ccccc1.P1SPS1.c1ccccc1 | c1ccc2c(c1)COCN2 | c1ccc2c(c1)COCN2.c1ccccc1 | Other | C1(=CC=CC=C1)C | 110 | null | CC1(C)OC(=O)Nc2ccc(-c3cccc(Br)c3)cc21.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1>C1(=CC=CC=C1)C>CC1(C)OC(=S)Nc2ccc(-c3cccc(Br)c3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7712dc9388da484a8a072bcd7f76f278 | O=c1c2c[nH]c3c(F)cccc3c-2nn1-c1ccc([N+](=O)[O-])cc1>>Nc1ccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)cc1 | C(C)(=O)OCC.O.O.[Sn](Cl)Cl.[N+](=O)([O-])C1=CC=C(C=C1)N1N=C2C(=CNC=3C(=CC=CC23)F)C1=O.[N+](=O)([O-])C1=CC=C(C=C1)N1N=C2C(=CNC=3C(=CC=CC23)F)C1=O.C([O-])(O)=O.[Na+]>>NC1=CC=C(C=C1)N1N=C2C(=CNC=3C(=CC=CC23)F)C1=O | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5](-[n:6]2[n:7][c:8]3[c:9]4[cH:10][cH:11][cH:12][c:13]([F:14])[c:15]4[nH:16][cH:17][c:18]-3[c:19]2=[O:20])[cH:21][cH:22]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5](-[n:6]2[n:7][c:8]3[c:9]4[cH:10][cH:11][cH:12][c:13]([F:14])[c:15]4[nH:16][cH:17][c:18]-3[c:19]2=[O:20])[cH:21][cH:22]1 | O=c1c2c[nH]c3c(F)cccc3c-2nn1-c1ccc([N+](=O)[O-])cc1 | Nc1ccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)cc1 | null | null | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=c1c2c[nH]c3ccccc3c-2nn1-c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 104.7 | [{"value": 99.0, "product": "NC1=CC=C(C=C1)N1N=C2C(=CNC=3C(=CC=CC23)F)C1=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 104.7, "product": "NC1=CC=C(C=C1)N1N=C2C(=CNC=3C(=CC=CC23)F)C1=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | Tin (II) chloride dihydrate (12.5 g, 0.055 mol) was added in one portion to a stirred solution of 2-(4-nitro-phenyl)-6-fluoro-2,5-dihydro-pyrazolo[4,3-c]quinolin-3-one (intermediate 1) (3.59 g, 0.011 mol) in ethyl alcohol (110 ml) at room temperature. The mixture was then heated to 80° C. for 8 h, cooled to room temper... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccc2c(c1)ncc1c[nH]nc12 | Other | C(C)O | 80 | null | O=c1c2c[nH]c3c(F)cccc3c-2nn1-c1ccc([N+](=O)[O-])cc1>C(C)O>Nc1ccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f5204a39d4c54ba09d8bf60f425a3b07 | CCC(C)C(=O)Cl.Nc1ccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)cc1>>CCC(C)C(=O)Nc1ccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)cc1 | CC(C(=O)Cl)CC.NC1=CC=C(C=C1)N1N=C2C(=CNC=3C(=CC=CC23)F)C1=O.NC1=CC=C(C=C1)N1N=C2C(=CNC=3C(=CC=CC23)F)C1=O.C(C)N(CC)CC>>FC1=CC=CC=2C=3C(=CNC12)C(N(N3)C3=CC=C(C=C3)NC(C(CC)C)=O)=O | Cl[C:5]([CH:3]([CH2:2][CH3:1])[CH3:4])=[O:6].[NH2:7][c:8]1[cH:9][cH:10][c:11](-[n:12]2[n:13][c:14]3[c:15]4[cH:16][cH:17][cH:18][c:19]([F:20])[c:21]4[nH:22][cH:23][c:24]-3[c:25]2=[O:26])[cH:27][cH:28]1>>[CH3:1][CH2:2][CH:3]([CH3:4])[C:5](=[O:6])[NH:7][c:8]1[cH:9][cH:10][c:11](-[n:12]2[n:13][c:14]3[c:15]4[cH:16][cH:17][c... | CCC(C)C(=O)Cl.Nc1ccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)cc1 | CCC(C)C(=O)Nc1ccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)cc1 | null | CN(C1=CC=NC=C1)C | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=c1c2c[nH]c3ccccc3c-2nn1-c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C;D1;H3:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C:4]-[C:3](-[C;D1;H3:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 26.4 | [{"value": 26.0, "product": "FC1=CC=CC=2C=3C(=CNC12)C(N(N3)C3=CC=C(C=C3)NC(C(CC)C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 26.4, "product": "FC1=CC=CC=2C=3C(=CNC12)C(N(N3)C3=CC=C(C=C3)NC(C(CC)C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | (±)-2-Methylbutyryl chloride (13.6 μl, 0.11 mmol) was added dropwise over 30 sec to a stirred solution of 2-(4-amino-phenyl)-6-fluoro-2,5-dihydro-pyrazolo[4,3-c]quinolin-3-one (Intermediate 2) (30 mg, 0.10 mmol), triethylamine (14 μl, 0.11 mmol) and 4-dimethylaminopyridine (2.4 mg, 0.02 mmol) in dichloromethane (1 ml) ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)ncc1c[nH]nc12 | HCl | CN(C1=CC=NC=C1)C.ClCCl | null | 16 | CCC(C)C(=O)Cl.Nc1ccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)cc1>CN(C1=CC=NC=C1)C.ClCCl>CCC(C)C(=O)Nc1ccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-866ba5d8f9af45bb90727795f570a17b | CCOC(=O)c1cnc2c(F)cccc2c1Cl.NNc1cccc(C(=O)O)c1>>O=C(O)c1cccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)c1 | Cl.N(N)C=1C=C(C(=O)O)C=CC1.C(C)OC(=O)C=1C=NC2=C(C=CC=C2C1Cl)F.[OH-].[Li+]>>FC1=CC=CC=2C=3C(=CNC12)C(N(N3)C=3C=C(C(=O)O)C=CC3)=O | CCO[C:22]([c:21]1[c:11](Cl)[c:12]2[cH:13][cH:14][cH:15][c:16]([F:17])[c:18]2[n:19][cH:20]1)=[O:23].[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([NH:9][NH2:10])[cH:24]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8](-[n:9]2[n:10][c:11]3[c:12]4[cH:13][cH:14][cH:15][c:16]([F:17])[c:18]4[nH:19][cH:20][c:21]-3[c:22]2... | CCOC(=O)c1cnc2c(F)cccc2c1Cl.NNc1cccc(C(=O)O)c1 | O=C(O)c1cccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)c1 | null | null | C(CCC)O.O1CCCC1.O | Aromatic Heterocycle Formation | OtherReaction | ee439f0d33eddb680aeae010a39ecb3e522826f644f963c6ba8a62694a2e2b1e | 20cc0446e4e8da9890d540018d45591431260c9e839f50bab7497c80b683dbef | O=c1c2c[nH]c3ccccc3c-2nn1-c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:3]1:[c:4]:[n;H0;D2;+0:5]:[c:6](:[c:7]):[c:8](:[c:9]):[c;H0;D3;+0:10]:1-Cl.[NH2;D1;+0:11]-[NH;D2;+0:12]-[c;H0;D3;+0:13](:[c:14]:[c:15]-[C:16](=[O;D1;H0:17])-[O;D1;H1:18]):[c:19]:[c:20]>>[O;D1;H0:17]=[C:16](-[O;D1;H1:18])-[c:15]:[c:14]:[c;H0;D3;+0:13](-[n;H0;D3;+0:12]1:[n;H0... | 65.2 | [{"value": 63.0, "product": "FC1=CC=CC=2C=3C(=CNC12)C(N(N3)C=3C=C(C(=O)O)C=CC3)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.2, "product": "FC1=CC=CC=2C=3C(=CNC12)C(N(N3)C=3C=C(C(=O)O)C=CC3)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | 3-Hydrazinobenzoic acid (1.91 g, 0.013 mol) was added in one portion to a stirred solution of 4-chloro-8-fluoro-quinoline-3-carboxylic acid ethyl ester (2.93 g, 0.011 mol) in n-butanol (60 ml) at room temperature. The solution was heated to reflux for 16 h, cooled to room temperature and the resulting yellow solid filt... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Aromatic halide.Ester | null | c1ccc2ncccc2c1 | c1ccc2c(c1)ncc1c[nH]nc12 | c1ccccc1.c1ccc2c(c1)ncc1c[nH]nc12 | HCl | C(CCC)O.O1CCCC1.O | null | 16 | CCOC(=O)c1cnc2c(F)cccc2c1Cl.NNc1cccc(C(=O)O)c1>C(CCC)O.O1CCCC1.O>O=C(O)c1cccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b99d872116fe4931a25f64e611601e06 | O=C(Cl)C(=O)Cl.O=C(O)c1cccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)c1>>O=C(Cl)c1cccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)c1 | CN(C=O)C.C(C(=O)Cl)(=O)Cl.FC1=CC=CC=2C=3C(=CNC12)C(N(N3)C=3C=C(C(=O)O)C=CC3)=O.FC1=CC=CC=2C=3C(=CNC12)C(N(N3)C=3C=C(C(=O)O)C=CC3)=O>>FC1=CC=CC=2C=3C(=CNC12)C(N(N3)C=3C=C(C(=O)Cl)C=CC3)=O | O=C(Cl)C(=O)[Cl:3].O[C:2](=[O:1])[c:4]1[cH:5][cH:6][cH:7][c:8](-[n:9]2[n:10][c:11]3[c:12]4[cH:13][cH:14][cH:15][c:16]([F:17])[c:18]4[nH:19][cH:20][c:21]-3[c:22]2=[O:23])[cH:24]1>>[O:1]=[C:2]([Cl:3])[c:4]1[cH:5][cH:6][cH:7][c:8](-[n:9]2[n:10][c:11]3[c:12]4[cH:13][cH:14][cH:15][c:16]([F:17])[c:18]4[nH:19][cH:20][c:21]-3[... | O=C(Cl)C(=O)Cl.O=C(O)c1cccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)c1 | O=C(Cl)c1cccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)c1 | null | null | ClCCl | Functional Group Interconversion | Alcohol to chloride_Other | 013cec2edeb273a7a148f349d36a52d99ff4e7bcf8eed78085df830088e387ac | aedb1f68dc5b7eb0583043e1125b741382b17974140a2f46554f0110e2ddc884 | O=c1c2c[nH]c3ccccc3c-2nn1-c1ccccc1 | Cl-C(=O)-C(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 96 | [{"value": 96.0, "product": "FC1=CC=CC=2C=3C(=CNC12)C(N(N3)C=3C=C(C(=O)Cl)C=CC3)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.9, "product": "FC1=CC=CC=2C=3C(=CNC12)C(N(N3)C=3C=C(C(=O)Cl)C=CC3)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | Oxalyl chloride (20 ml, 0.2 mol) was added dropwise over 2 min to a stirred solution of 3-(6-fluoro-3-oxo-3,5-dihydro-pyrazolo[4,3-c]quinolin-2-yl)-benzoic acid (intermediate 3) (2.0 g, 6.1 mmol) in dichloromethane (10 ml) at room temperature. N,N-Dimethylformamide (50 μl) was then added and the resulting mixture heate... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Carboxylic acid | Acyl halide | null | null | c1ccccc1.c1ccc2c(c1)ncc1c[nH]nc12 | HCl | ClCCl | 50 | null | O=C(Cl)C(=O)Cl.O=C(O)c1cccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)c1>ClCCl>O=C(Cl)c1cccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-17c5c40e4c584119be22329d4d1bff41 | COCCCN.O=C(Cl)c1cccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)c1>>COCCCNC(=O)c1cccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)c1 | C(C)N(CC)CC.COCCCN.FC1=CC=CC=2C=3C(=CNC12)C(N(N3)C=3C=C(C(=O)Cl)C=CC3)=O.FC1=CC=CC=2C=3C(=CNC12)C(N(N3)C=3C=C(C(=O)Cl)C=CC3)=O.Cl>>FC1=CC=CC=2C=3C(=CNC12)C(N(N3)C=3C=C(C(=O)NCCCOC)C=CC3)=O | [CH3:1][O:2][CH2:3][CH2:4][CH2:5][NH2:6].Cl[C:7](=[O:8])[c:9]1[cH:10][cH:11][cH:12][c:13](-[n:14]2[n:15][c:16]3[c:17]4[cH:18][cH:19][cH:20][c:21]([F:22])[c:23]4[nH:24][cH:25][c:26]-3[c:27]2=[O:28])[cH:29]1>>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][cH:12][c:13](-[n:14]2[n:15][c:16]3[c:17]... | COCCCN.O=C(Cl)c1cccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)c1 | COCCCNC(=O)c1cccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)c1 | null | null | O1CCCC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=c1c2c[nH]c3ccccc3c-2nn1-c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 69 | [{"value": 69.0, "product": "FC1=CC=CC=2C=3C(=CNC12)C(N(N3)C=3C=C(C(=O)NCCCOC)C=CC3)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | 3-Methoxypropylamine (0.026 g, 0.29 mmol) was added to a stirred solution of 3-(6-fluoro-3-oxo-3,5-dihydro-pyrazolo[4,3-c]quinolin-2-yl)-benzoyl chloride (intermediate 4) (26 mg 0.29 mmol) in tetrahydrofuran (2 ml) and the mixture stirred at room temperature for 15 min. Triethylamine (0.2 ml, 1.4 mmol) was then added a... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)ncc1c[nH]nc12 | HCl | O1CCCC1 | null | 0.25 | COCCCN.O=C(Cl)c1cccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)c1>O1CCCC1>COCCCNC(=O)c1cccc(-n2nc3c4cccc(F)c4[nH]cc-3c2=O)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9c5e52f4a35d4393b82cadb4af74d145 | CCOC(=O)c1ccccc1N.COC(=O)CC(=O)C1CC1>>CCOC(=O)c1c(C2CC2)[nH]c2ccccc2c1=O | COC(CC(=O)C1CC1)=O.C(C)OC(C1=C(C=CC=C1)N)=O.C1(=CC=CC=C1)C>>C(C)OC(=O)C1=C(NC2=CC=CC=C2C1=O)C1CC1 | [CH3:1][CH2:2][O:3][C:18]([c:17]1[c:12]([NH2:11])[cH:13][cH:14][cH:15][cH:16]1)=[O:19].CO[C:4](=[O:5])[CH2:6][C:7](=O)[CH:8]1[CH2:9][CH2:10]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH:8]2[CH2:9][CH2:10]2)[nH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[c:18]1=[O:19] | CCOC(=O)c1ccccc1N.COC(=O)CC(=O)C1CC1 | CCOC(=O)c1c(C2CC2)[nH]c2ccccc2c1=O | null | C1(=CC=C(C=C1)S(=O)(=O)O)C | null | Aromatic Heterocycle Formation | OtherReaction | 491bd2fdcb2b219c36e07712d3416b2b20d234f8420994329b56ea19314c754b | 1f7cfbf178b989a5dc61b8bb4fcd61ce54e19d0cd6c69f55ae836eb22030509b | O=c1cc(C2CC2)[nH]c2ccccc12 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[C;H0;D3;+0:4](=O)-[C:5]1-[C:6]-[C:7]-1.[C;D1;H3:8]-[C:9]-[O;H0;D2;+0:10]-[C;H0;D3;+0:11](=[O;D1;H0:12])-[c:13](:[c:14]):[c:15](-[NH2;D1;+0:16]):[c:17]>>[C;D1;H3:8]-[C:9]-[O;H0;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:3]1:[c;H0;D3;+0:11](=[O;D1;H0:12]):[c:13](:[c... | 53 | [{"value": 53.0, "product": "C(C)OC(=O)C1=C(NC2=CC=CC=C2C1=O)C1CC1", "details": "PERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 2 | HOUR | A solution of 3-cyclopropyl-3-oxo-propionic acid methyl ester (6.2 g, 0.038 mols), 2-amino benzoic acid ethyl ester (4.95 g, 0.03 mols) and p-toluene sulfonic acid (0.04 g, 0.2 mmols) in toluene (25 ml) was heated at 125° C. for 2 h; 15 ml of solvent was then distilled. To the residual orange solution was added sodium ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Ester.Primary amine | Ester | c1ccccc1 | c1cnc2ccccc2c1 | C1CC1.c1cnc2ccccc2c1 | HO- | C1(=CC=C(C=C1)S(=O)(=O)O)C | 120 | 2 | CCOC(=O)c1ccccc1N.COC(=O)CC(=O)C1CC1>C1(=CC=C(C=C1)S(=O)(=O)O)C>CCOC(=O)c1c(C2CC2)[nH]c2ccccc2c1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4872319f5f1945ae911cbcc86e7b9e1a | CCOC(=O)c1c(C2CC2)[nH]c2ccccc2c1=O.O=P(Cl)(Cl)Cl>>CCOC(=O)c1c(C2CC2)nc2ccccc2c1Cl | P(=O)(Cl)(Cl)Cl.C(C)OC(=O)C1=C(NC2=CC=CC=C2C1=O)C1CC1.C([O-])(O)=O.[Na+]>>C(C)OC(=O)C=1C(=NC2=CC=CC=C2C1Cl)C1CC1 | O=[c:18]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:7]([CH:8]2[CH2:9][CH2:10]2)[nH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]21.O=P(Cl)(Cl)[Cl:19]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH:8]2[CH2:9][CH2:10]2)[n:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[c:18]1[Cl:19] | CCOC(=O)c1c(C2CC2)[nH]c2ccccc2c1=O.O=P(Cl)(Cl)Cl | CCOC(=O)c1c(C2CC2)nc2ccccc2c1Cl | null | null | C(C)#N | Functional Group Interconversion | OtherReaction | 608f63cb1f4eb5f8ff4f6128056e651e12d8905ddec242decf5bdb71da52a2d7 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc2nc(C3CC3)ccc2c1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[c:3](:[c:4]):[c:5](:[c:6]):[nH;D2;+0:7]:[c:8](-[C:9]):[c:10]:1-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14]>>[C:14]-[#8:13]-[C:11](=[O;D1;H0:12])-[c:10]1:[c:8](-[C:9]):[n;H0;D2;+0:7]:[c:5](:[c:6]):[c:3](:[c:4]):[c;H0;D3;+0:2]:1-[Cl;H0;D1;+0:1] | 106 | [{"value": 106.0, "product": "C(C)OC(=O)C=1C(=NC2=CC=CC=C2C1Cl)C1CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 10.2, "product": "C(C)OC(=O)C=1C(=NC2=CC=CC=C2C1Cl)C1CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | null | null | Phosphorus oxychloride (0.77 ml, 0.082 mols) was added in one portion to a suspension of 2-cyclopropyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester (1.0 g, 0.041 mols) in acetonitrile and the mixture was heated at 75° C. for 90 minutes (becomes a clear solution above 65° C.). The resulting light brown solu... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1cnc2ccccc2c1 | c1ccc2ncccc2c1 | C1CC1.c1ccc2ncccc2c1 | HCl | C(C)#N | 75 | null | CCOC(=O)c1c(C2CC2)[nH]c2ccccc2c1=O.O=P(Cl)(Cl)Cl>C(C)#N>CCOC(=O)c1c(C2CC2)nc2ccccc2c1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-924acceae61043aa9030a239df61f749 | CCOC(=O)c1c(C2CC2)nc2ccccc2c1Cl.NNc1ccc(C(=O)O)cc1>>O=C(O)c1ccc(-n2nc3c4ccccc4[nH]c(C4CC4)c-3c2=O)cc1 | C(C)OC(=O)C=1C(=NC2=CC=CC=C2C1Cl)C1CC1.N(N)C1=CC=C(C(=O)O)C=C1.NN>>C1(CC1)C=1NC=2C=CC=CC2C=2C1C(N(N2)C2=CC=C(C(=O)O)C=C2)=O | CCO[C:23]([c:22]1[c:10](Cl)[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[n:17][c:18]1[CH:19]1[CH2:20][CH2:21]1)=[O:24].[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([NH:8][NH2:9])[cH:25][cH:26]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7](-[n:8]2[n:9][c:10]3[c:11]4[cH:12][cH:13][cH:14][cH:15][c:16]4[nH:17][c:18]([CH:19]4[CH2... | CCOC(=O)c1c(C2CC2)nc2ccccc2c1Cl.NNc1ccc(C(=O)O)cc1 | O=C(O)c1ccc(-n2nc3c4ccccc4[nH]c(C4CC4)c-3c2=O)cc1 | null | null | Cl.CCCCCCC.C(C)O | Aromatic Heterocycle Formation | OtherReaction | ee439f0d33eddb680aeae010a39ecb3e522826f644f963c6ba8a62694a2e2b1e | 20cc0446e4e8da9890d540018d45591431260c9e839f50bab7497c80b683dbef | O=c1c2c(C3CC3)[nH]c3ccccc3c-2nn1-c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:3]1:[c:4](-[C:5]):[n;H0;D2;+0:6]:[c:7](:[c:8]):[c:9](:[c:10]):[c;H0;D3;+0:11]:1-Cl.[NH2;D1;+0:12]-[NH;D2;+0:13]-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17]:[c:18]>>[C:5]-[c:4]1:[nH;D2;+0:6]:[c:7](:[c:8]):[c:9](:[c:10]):[c;H0;D3;+0:11]2:[n;H0;D2;+0:12]:[n;H0;D3;+0:13](-[c;H0;D3;... | 80.2 | [{"value": 80.0, "product": "C1(CC1)C=1NC=2C=CC=CC2C=2C1C(N(N2)C2=CC=C(C(=O)O)C=C2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.2, "product": "C1(CC1)C=1NC=2C=CC=CC2C=2C1C(N(N2)C2=CC=C(C(=O)O)C=C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-chloro-2-cyclopropyl-quinoline-3-carboxylic acid ethyl ester (1.15 g, 0.0041 mols) and 4-hydrazino-benzoic acid (1.0 g, 0.0068 mols) were stirred in ethanol (30 ml) at reflux for 16 h. The bright yellow suspension was diluted with heptane, filtered, washed with cold t-butylmethyl ether and left to dry under suction t... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Aromatic halide.Ester | null | c1ccc2ncccc2c1 | c1ccc2c(c1)ncc1c[nH]nc12 | c1ccccc1.c1ccc2c(c1)ncc1c[nH]nc12.C1CC1 | HCl | Cl.CCCCCCC.C(C)O | null | null | CCOC(=O)c1c(C2CC2)nc2ccccc2c1Cl.NNc1ccc(C(=O)O)cc1>Cl.CCCCCCC.C(C)O>O=C(O)c1ccc(-n2nc3c4ccccc4[nH]c(C4CC4)c-3c2=O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c8319f031c8746a7bda69ce0ffb04f8a | O=C(Cl)C(=O)Cl.O=C(O)c1ccc(-n2nc3c4ccccc4[nH]c(C4CC4)c-3c2=O)cc1>>O=C(Cl)c1ccc(-n2nc3c4ccccc4[nH]c(C4CC4)c-3c2=O)cc1 | C1(CC1)C=1NC=2C=CC=CC2C=2C1C(N(N2)C2=CC=C(C(=O)O)C=C2)=O.C(C(=O)Cl)(=O)Cl.CN(C=O)C>>C1(CC1)C=1NC=2C=CC=CC2C=2C1C(N(N2)C2=CC=C(C(=O)Cl)C=C2)=O | O=C(Cl)C(=O)[Cl:3].O[C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7](-[n:8]2[n:9][c:10]3[c:11]4[cH:12][cH:13][cH:14][cH:15][c:16]4[nH:17][c:18]([CH:19]4[CH2:20][CH2:21]4)[c:22]-3[c:23]2=[O:24])[cH:25][cH:26]1>>[O:1]=[C:2]([Cl:3])[c:4]1[cH:5][cH:6][c:7](-[n:8]2[n:9][c:10]3[c:11]4[cH:12][cH:13][cH:14][cH:15][c:16]4[nH:17][c:18]([CH:... | O=C(Cl)C(=O)Cl.O=C(O)c1ccc(-n2nc3c4ccccc4[nH]c(C4CC4)c-3c2=O)cc1 | O=C(Cl)c1ccc(-n2nc3c4ccccc4[nH]c(C4CC4)c-3c2=O)cc1 | null | null | ClCCl | Functional Group Interconversion | Alcohol to chloride_Other | 013cec2edeb273a7a148f349d36a52d99ff4e7bcf8eed78085df830088e387ac | aedb1f68dc5b7eb0583043e1125b741382b17974140a2f46554f0110e2ddc884 | O=c1c2c(C3CC3)[nH]c3ccccc3c-2nn1-c1ccccc1 | Cl-C(=O)-C(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | 45 | CELSIUS | 8 | HOUR | To a suspension of finely ground 4-(4-cyclopropyl-3-oxo-3,5-dihydro-pyrazolo[4,3-c]quinolin-2-yl)-benzoic acid (0.19 g. 0.55 mmol) in dichloromethane (4 ml) was added oxalyl chloride (1.6 ml, 0.01 mol) followed by a drop of dimethyl formamide. The mixture was stirred under nitrogen at 45° C. for 8 h. The solvent was re... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Carboxylic acid | Acyl halide | null | null | c1ccccc1.c1ccc2c(c1)ncc1c[nH]nc12.C1CC1 | HCl | ClCCl | 45 | 8 | O=C(Cl)C(=O)Cl.O=C(O)c1ccc(-n2nc3c4ccccc4[nH]c(C4CC4)c-3c2=O)cc1>ClCCl>O=C(Cl)c1ccc(-n2nc3c4ccccc4[nH]c(C4CC4)c-3c2=O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e5ce23572c0a4884939891bce2bc781d | CN(C)CCCN.O=C(Cl)c1ccc(-n2nc3c4ccccc4[nH]c(C4CC4)c-3c2=O)cc1>>CN(C)CCCNC(=O)c1ccc(-n2nc3c4ccccc4[nH]c(C4CC4)c-3c2=O)cc1 | C1(CC1)C=1NC=2C=CC=CC2C=2C1C(N(N2)C2=CC=C(C(=O)Cl)C=C2)=O.CN(CCCN)C>>CN(CCCNC(C1=CC=C(C=C1)N1N=C2C(=C(NC=3C=CC=CC23)C2CC2)C1=O)=O)C | [CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH2:6][NH2:7].Cl[C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13](-[n:14]2[n:15][c:16]3[c:17]4[cH:18][cH:19][cH:20][cH:21][c:22]4[nH:23][c:24]([CH:25]4[CH2:26][CH2:27]4)[c:28]-3[c:29]2=[O:30])[cH:31][cH:32]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:9])[c:10]1[cH:11][cH:12][c... | CN(C)CCCN.O=C(Cl)c1ccc(-n2nc3c4ccccc4[nH]c(C4CC4)c-3c2=O)cc1 | CN(C)CCCNC(=O)c1ccc(-n2nc3c4ccccc4[nH]c(C4CC4)c-3c2=O)cc1 | null | null | O1CCCC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=c1c2c(C3CC3)[nH]c3ccccc3c-2nn1-c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 47.4 | [{"value": 47.0, "product": "CN(CCCNC(C1=CC=C(C=C1)N1N=C2C(=C(NC=3C=CC=CC23)C2CC2)C1=O)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.4, "product": "CN(CCCNC(C1=CC=C(C=C1)N1N=C2C(=C(NC=3C=CC=CC23)C2CC2)C1=O)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a partial solution of 4-(4-cyclopropyl-3-oxo-3,5-dihydro-pyrazolo[4,3-c]quinolin-2-yl)-benzoyl chloride (0.1 g, 0.28 mmol) in tetrahydrofurane (6 ml) under nitrogen was added a solution of 3-dimethylamino-propyl amine (0.03 g, 0.3 mmol) in tetrahydrofurane (3 ml). The mixture was stirred at RT for 3 h. The solvent w... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)ncc1c[nH]nc12.C1CC1 | HCl | O1CCCC1 | null | 3 | CN(C)CCCN.O=C(Cl)c1ccc(-n2nc3c4ccccc4[nH]c(C4CC4)c-3c2=O)cc1>O1CCCC1>CN(C)CCCNC(=O)c1ccc(-n2nc3c4ccccc4[nH]c(C4CC4)c-3c2=O)cc1 |
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