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-018fd0e1351f4fd09b20fcddd97b4c7a | ord-17e9636eed33420492e40692304b41dc | CCOC(=O)c1coc2c1C(=O)CCC2.[NH4+]>>CCOC(=O)c1c[nH]c2c1C(=O)CCC2 | O=C1CCCC2=C1C(=CO2)C(=O)OCC.C(C)(=O)[O-].[NH4+]>>O=C1C=2C(=CNC2CCC1)C(=O)OCC | o1[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:10]2[c:9]1[CH2:15][CH2:14][CH2:13][C:11]2=[O:12].[NH4+:8]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][nH:8][c:9]2[c:10]1[C:11](=[O:12])[CH2:13][CH2:14][CH2:15]2 | CCOC(=O)c1coc2c1C(=O)CCC2.[NH4+] | CCOC(=O)c1c[nH]c2c1C(=O)CCC2 | null | null | CN(C=O)C | Functional Group Interconversion | OtherReaction | 9f95c6080356ded1ef1670dae574db79ae3eb64e31cc1bed277c0a72203f3f74 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | O=C1CCCc2[nH]ccc21 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]1:[cH;D2;+0:6]:o:[c;H0;D3;+0:7]2:[c:8]:1-[C:9](=[O;D1;H0:10])-[C:11]-[C:12]-[C:13]-2.[NH4+;D0:14]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]1:[cH;D2;+0:6]:[nH;D2;+0:14]:[c;H0;D3;+0:7]2:[c:8]:1-[C:9](=[O;D1;H0:10])-[C:11]-[C:12]-[C:13]-2 | null | [] | 100 | CELSIUS | null | null | To a stirred suspension of 4-oxo-4,5,6,7-tetrahydrobenzofuran-3-carboxylic acid (28.2 g, 157 mmol) in ethyl alcohol (500 mL) under nitrogen at ambient temperature was added acetyl chloride(56 mL, 783 mmol) dropwise. After stirring 1 h, the solution was then heated at reflux for 1 h. The solution was cooled and concentr... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1cc2c(o1)CCCC2 | c1cc2c([nH]1)CCCC2 | c1cc2c([nH]1)CCCC2 | HO- | CN(C=O)C | 100 | null | CCOC(=O)c1coc2c1C(=O)CCC2.[NH4+]>CN(C=O)C>CCOC(=O)c1c[nH]c2c1C(=O)CCC2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8b608848da114cdfac3d97231295362b | COc1cccc2[nH]ccc12.O=C(Cl)C(Cl)(Cl)Cl>>COc1cccc2[nH]cc(C(=O)C(Cl)(Cl)Cl)c12 | COC1=C2C=CNC2=CC=C1.N1=CC=CC=C1.ClC(C(=O)Cl)(Cl)Cl>>COC1=C2C(=CNC2=CC=C1)C(C(Cl)(Cl)Cl)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[nH:8][cH:9][cH:10][c:17]12.Cl[C:11](=[O:12])[C:13]([Cl:14])([Cl:15])[Cl:16]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[nH:8][cH:9][c:10]([C:11](=[O:12])[C:13]([Cl:14])([Cl:15])[Cl:16])[c:17]12 | COc1cccc2[nH]ccc12.O=C(Cl)C(Cl)(Cl)Cl | COc1cccc2[nH]cc(C(=O)C(Cl)(Cl)Cl)c12 | null | null | ClCCl | C-C Coupling | Friedel-Crafts acylation | bc61c2f3c4095d2339fbb0f834e9655112dfadeca9b866efcca6455903db578f | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | c1ccc2[nH]ccc2c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[Cl;D1;H0:4])(-[Cl;D1;H0:5])-[Cl;D1;H0:6].[c:7]:[c:8]1:[cH;D2;+0:9]:[c:10]:[#7;a:11]:[c:12]:1:[c:13]>>[Cl;D1;H0:4]-[C:3](-[Cl;D1;H0:5])(-[Cl;D1;H0:6])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:9]1:[c:10]:[#7;a:11]:[c:12](:[c:13]):[c:8]:1:[c:7] | null | [] | 0 | CELSIUS | 1.5 | HOUR | To a solution of 4-methoxy-1H-indole (7.15 g, 49 mmol) and pyridine (19.7 mL, 243 mmol) in dichloromethane (50 mL) at 0° C. under nitrogen was added dropwise a solution of trichloroacetyl chloride (27.1 mL, 243 mmol) in dichloromethane (50 mL). After stirring at 0° C. for an additional 1.5 h, the mixture was concentrat... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HCl | ClCCl | 0 | 1.5 | COc1cccc2[nH]ccc12.O=C(Cl)C(Cl)(Cl)Cl>ClCCl>COc1cccc2[nH]cc(C(=O)C(Cl)(Cl)Cl)c12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c3c99a608b9c4984be003f74893691b4 | BrBr.O=C1CCCCCC1.OCCO>>BrC1CCCCCC12OCCO2 | C([O-])(O)=O.[Na+].BrBr.C1(CCCCCC1)=O.C(CO)O>>C1COC2(C(CCCCC2)Br)O1 | Br[Br:1].[CH2:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1=[O:9].O[CH2:10][CH2:11][OH:12]>>[Br:1][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]12[O:9][CH2:10][CH2:11][O:12]2 | BrBr.O=C1CCCCCC1.OCCO | BrC1CCCCCC12OCCO2 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 1ae58e1ca1c479631126e708a0e29f6dade83cf7ac97d5420287c8e1719eaf08 | 244bbebd4ff794c208c011e0b1c39f7b4d8ab8cc450319d6e7a07a2de975d00a | C1CCCC2(CC1)OCCO2 | Br-[Br;H0;D1;+0:1].O-[CH2;D2;+0:2]-[C:3]-[OH;D1;+0:4].[C:5]-[C:6]-[CH2;D2;+0:7]-[C;H0;D3;+0:8](=[O;H0;D1;+0:9])-[C:10]-[C:11]>>[Br;H0;D1;+0:1]-[CH;D3;+0:7](-[C:6]-[C:5])-[C;H0;D4;+0:8]1(-[C:10]-[C:11])-[O;H0;D2;+0:4]-[C:3]-[CH2;D2;+0:2]-[O;H0;D2;+0:9]-1 | null | [] | null | null | 5 | HOUR | Bromine (44.8 g, 0.28 mol) was added dropwise to a stirred solution of cycloheptanone (28.5 g, 0.25 mol) in a 1:1 solution (300 mL) of ethylene glycol and tetrahydrofuran at room temperature. The mixture was stirred for 5 hours, then poured into aqueous sodium bicarbonate and extracted 3× with diethyl ether. The combin... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary alcohol.Primary alcohol | Secondary halide.Ether.Ether | C1CCCCCC1 | C1CCCC2(CC1)OCCO2 | C1CCCC2(CC1)OCCO2 | HBr | O1CCCC1 | null | 5 | BrBr.O=C1CCCCCC1.OCCO>O1CCCC1>BrC1CCCCCC12OCCO2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-02e021bf3546479584ca183e01838f59 | C1=CC2(CCCC1)OCCO2>>OC1CCCCC2(C1)OCCO2 | O1CCCC1.[BH4-].[Na+].[Cl-].[Na+].C1COC2(C=CCCCC2)O1>>C1COC2(CC(CCCC2)O)O1 | [CH2:2]1[CH2:3][CH2:4][CH:5]=[CH:6][C:7]2([CH2:8]1)[O:9][CH2:10][CH2:11][O:12]2>>[OH:1][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][C:7]2([CH2:8]1)[O:9][CH2:10][CH2:11][O:12]2 | C1=CC2(CCCC1)OCCO2 | OC1CCCCC2(C1)OCCO2 | null | C(C)(=O)[O-].[Hg+2].C(C)(=O)[O-] | [OH-].[Na+].O | Oxidation | OtherReaction | efd11b7b160805d9c57d8444d1e11b1d45ecc089fa41335c2359e8aefc820ed1 | ea9c82bfa175e68b5ba3ab70b04cbe912175f11a5a7fcedc63d371ab5e0920fd | C1CCCC2(CC1)OCCO2 | [#8:1]1-[C:2]-[C:3]-[#8:4]-[C:5]-12-[C:6]-[CH2;D2;+0:7]-[C:8]-[C:9]-[CH;D2;+0:10]=[CH;D2;+0:11]-2>>[O;D1;H1:12]-[CH;D3;+0:7]1-[C:8]-[C:9]-[CH2;D2;+0:10]-[CH2;D2;+0:11]-[C:5]2(-[#8:1]-[C:2]-[C:3]-[#8:4]-2)-[C:6]-1 | null | [] | null | null | 3 | HOUR | Mercury(II) acetate (80.7 g, 0.25 mol) was dissolved in water (150 mL), then tetrahydrofuran (150 mL) was added to give a suspension. To this stirring suspension was added 2-cycloheptenone ethylene ketal (39 g, 0.25 mol). After stirring at ambient temperature for 3 hours, the mixture was cooled in an ice water bath. A ... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary alcohol | C1=CC2(CCCC1)OCCO2 | C1CCCC2(CC1)OCCO2 | C1CCCC2(CC1)OCCO2 | Other | C(C)(=O)[O-].[Hg+2].C(C)(=O)[O-].[OH-].[Na+].O | null | 3 | C1=CC2(CCCC1)OCCO2>C(C)(=O)[O-].[Hg+2].C(C)(=O)[O-].[OH-].[Na+].O>OC1CCCCC2(C1)OCCO2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f48acf1ecad04b97bb8efe00ecb3119b | CCOC(=O)c1coc2c1C(=O)CCCC2.[NH4+]>>CCOC(=O)c1c[nH]c2c1C(=O)CCCC2 | O=C1CCCCC=2OC=C(C21)C(=O)OCC.C(C)(=O)[O-].[NH4+]>>O=C1CCCCC=2NC=C(C21)C(=O)OCC | o1[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:10]2[c:9]1[CH2:16][CH2:15][CH2:14][CH2:13][C:11]2=[O:12].[NH4+:8]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][nH:8][c:9]2[c:10]1[C:11](=[O:12])[CH2:13][CH2:14][CH2:15][CH2:16]2 | CCOC(=O)c1coc2c1C(=O)CCCC2.[NH4+] | CCOC(=O)c1c[nH]c2c1C(=O)CCCC2 | null | null | CN(C=O)C | Functional Group Interconversion | OtherReaction | 9f5a0979fbc34e95a82a60b7ff6a72daede53fd93c8a794fc9c2745585af02f2 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | O=C1CCCCc2[nH]ccc21 | [C:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[c:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9]):[cH;D2;+0:10]:o:[c;H0;D3;+0:11]:1-[C:12]-[C:13].[NH4+;D0:14]>>[C:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[c:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9]):[cH;D2;+0:10]:[nH;D2;+0:14]:[c;H0;D3;+0:11]:1-[C:12]-[C:13] | 50.7 | [{"value": 50.7, "product": "O=C1CCCCC=2NC=C(C21)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 115 | CELSIUS | null | null | A mixture of ethyl 4-oxo-5,6,7,8-tetrahydro-4H-cyclohepta[b]furan-3-carboxylate (3.48 g, 15.7 mmol) and ammonium acetate (2.41 g, 31.3 mmol) in N,N-dimethylformamide (25 mL) was heated at 115° C. for 6 hours. The mixture was concentrated in vacuo, ice water was added, then extracted 2× with dichloromethane. The combine... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1cc2c(o1)CCCCC2 | c1cc2c([nH]1)CCCCC2 | c1cc2c([nH]1)CCCCC2 | HO- | CN(C=O)C | 115 | null | CCOC(=O)c1coc2c1C(=O)CCCC2.[NH4+]>CN(C=O)C>CCOC(=O)c1c[nH]c2c1C(=O)CCCC2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2b79dceda53e44969acdb4dd9345d9f9 | CCOC(=O)c1c[nH]c2c1C(=O)CCCC2>>O=C(O)c1c[nH]c2c1C(=O)CCCC2 | O=C1CCCCC=2NC=C(C21)C(=O)OCC.Cl>>O=C1CCCCC=2NC=C(C21)C(=O)O | CC[O:3][C:2](=[O:1])[c:4]1[cH:5][nH:6][c:7]2[c:8]1[C:9](=[O:10])[CH2:11][CH2:12][CH2:13][CH2:14]2>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][nH:6][c:7]2[c:8]1[C:9](=[O:10])[CH2:11][CH2:12][CH2:13][CH2:14]2 | CCOC(=O)c1c[nH]c2c1C(=O)CCCC2 | O=C(O)c1c[nH]c2c1C(=O)CCCC2 | null | null | [OH-].[Na+].C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C1CCCCc2[nH]ccc21 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | null | null | A mixture of ethyl 4-oxo-5,6,7,8-tetrahydro-4H-cyclohepta[b]furan-3-carboxylate (3.48 g, 15.7 mmol) and ammonium acetate (2.41 g, 31.3 mmol) in N,N-dimethylformamide (25 mL) was heated at 115° C. for 6 hours. The mixture was concentrated in vacuo, ice water was added, then extracted 2× with dichloromethane. The combine... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cc2c([nH]1)CCCCC2 | Other | [OH-].[Na+].C(C)O | null | null | CCOC(=O)c1c[nH]c2c1C(=O)CCCC2>[OH-].[Na+].C(C)O>O=C(O)c1c[nH]c2c1C(=O)CCCC2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-05b0fb4c7ea14e67893d469ab2bbf43f | CCOC(=O)c1coc2c1C(=O)N(CC)CC2.[NH4+]>>CCOC(=O)c1c[nH]c2c1C(=O)N(CC)CC2 | O=C1N(CCC2=C1C(=CO2)C(=O)OCC)CC.C(C)(=O)[O-].[NH4+]>>O=C1N(CCC2=C1C(=CN2)C(=O)OCC)CC | o1[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:10]2[c:9]1[CH2:17][CH2:16][N:13]([CH2:14][CH3:15])[C:11]2=[O:12].[NH4+:8]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][nH:8][c:9]2[c:10]1[C:11](=[O:12])[N:13]([CH2:14][CH3:15])[CH2:16][CH2:17]2 | CCOC(=O)c1coc2c1C(=O)N(CC)CC2.[NH4+] | CCOC(=O)c1c[nH]c2c1C(=O)N(CC)CC2 | null | null | CN(C=O)C | Functional Group Interconversion | OtherReaction | e6f10b775605202dd66ed9336bcf6af9335d07c48be779aa0496df59469f1392 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | O=C1NCCc2[nH]ccc21 | [C:1]-[#7:2]1-[C:3]-[C:4]-[c;H0;D3;+0:5]2:o:[cH;D2;+0:6]:[c:7](-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11]):[c:12]:2-[C:13]-1=[O;D1;H0:14].[NH4+;D0:15]>>[C:1]-[#7:2]1-[C:3]-[C:4]-[c;H0;D3;+0:5]2:[nH;D2;+0:15]:[cH;D2;+0:6]:[c:7](-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11]):[c:12]:2-[C:13]-1=[O;D1;H0:14] | 53.6 | [{"value": 53.6, "product": "O=C1N(CCC2=C1C(=CN2)C(=O)OCC)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 115 | CELSIUS | null | null | A mixture of ethyl 4-oxo-5-ethyl-4,5,6,7-tetrahydro-furo[3,2-c]pyridine-3-carboxylate (3.66 g, 15.4 mmol) and ammonium acetate (5.94 g, 77.1 mmol) in N,N-dimethylformamide (30 mL) was heated at 115° C. for 23 hours. The mixture was cooled, concentrated in vacuo, ice water added, and the precipitate collected and dried ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1cc2c(o1)CC[NH]C2 | c1cc2c([nH]1)CC[NH]C2 | c1cc2c([nH]1)CC[NH]C2 | HO- | CN(C=O)C | 115 | null | CCOC(=O)c1coc2c1C(=O)N(CC)CC2.[NH4+]>CN(C=O)C>CCOC(=O)c1c[nH]c2c1C(=O)N(CC)CC2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5cd86490cc5f416d8215674f1fbf73d6 | C[O-].Nc1ccc2ccc(Cl)nc2n1>>COc1ccc2ccc(N)nc2n1 | ClC1=NC2=NC(=CC=C2C=C1)N.C[O-].[Na+]>>COC1=NC2=NC(=CC=C2C=C1)N | [CH3:1][O-:2].Cl[c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][c:9]([NH2:10])[n:11][c:12]2[n:13]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][c:9]([NH2:10])[n:11][c:12]2[n:13]1 | C[O-].Nc1ccc2ccc(Cl)nc2n1 | COc1ccc2ccc(N)nc2n1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | cb1cbe0ae0eb660667fc11f09b8575d57878f8f1ea561deb7c1da8ba1163c05f | 51fd03eb6a688046e417b9ed09ea0e72062396d005af1318b9b5f376a97da959 | c1cnc2ncccc2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](:[#7;a:4]:[c:5]):[c:6]:[c:7]:[c:8]:1.[C;D1;H3:9]-[O-;H0;D1:10]>>[C;D1;H3:9]-[O;H0;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](:[#7;a:4]:[c:5]):[c:6]:[c:7]:[c:8]:1 | null | [] | null | null | null | null | A mixture of 2-chloro-7-amino-1,8-napthyridine (Newkome, G. R. et al, J. Org. Chem., 1981, 46, 833-39) (180 mg, 1 mmol) and a methanolic solution of sodium methoxide (458 μL, 25 wt. %) in methyl alcohol (2 mL) was heated at 50° C. for 19 hours. The reaction mixture was allowed to cool, filtered through Celite using dic... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Ether | c1cnc2ncccc2c1 | c1cnc2ncccc2c1 | c1cnc2ncccc2c1 | Other | CO | null | null | C[O-].Nc1ccc2ccc(Cl)nc2n1>CO>COc1ccc2ccc(N)nc2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b9c7d82499f7455298f6c3c1fbf3995e | O=C(O)c1c[nH]c2c1C(=O)CCC2.O=C1CCC(=O)N1Br>>O=C(O)c1c(Br)[nH]c2c1C(=O)CCC2 | O=C1C=2C(=CNC2CCC1)C(=O)O.C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O.BrN1C(CCC1=O)=O>>BrC=1NC=2CCCC(C2C1C(=O)O)=O | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][nH:7][c:8]2[c:9]1[C:10](=[O:11])[CH2:12][CH2:13][CH2:14]2.O=C1CCC(=O)N1[Br:6]>>[O:1]=[C:2]([OH:3])[c:4]1[c:5]([Br:6])[nH:7][c:8]2[c:9]1[C:10](=[O:11])[CH2:12][CH2:13][CH2:14]2 | O=C(O)c1c[nH]c2c1C(=O)CCC2.O=C1CCC(=O)N1Br | O=C(O)c1c(Br)[nH]c2c1C(=O)CCC2 | null | null | CN(C=O)C | Functional Group Interconversion | Bromination | 228ae9e8e46dea8901dfc01c08955d471414024de38086d9b22d0af658d411ef | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=C1CCCc2[nH]ccc21 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[O;D1;H0:2]=[C:3]-[c:4]1:[c:5]:[#7;a:6]:[cH;D2;+0:7]:[c:8]:1-[C:9](=[O;D1;H0:10])-[O;D1;H1:11]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:7]1:[#7;a:6]:[c:5]:[c:4](:[c:8]:1-[C:9](=[O;D1;H0:10])-[O;D1;H1:11])-[C:3]=[O;D1;H0:2] | 29.1 | [{"value": 29.1, "product": "BrC=1NC=2CCCC(C2C1C(=O)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid (886 mg, 5 mmol) and catalytic benzoyl peroxide in N,N-dimethylformamide (5 mL) at 0° C. was added N-bromosuccinimide (1.869 g, 10.5 mmol)in four equal portions over 1 hour. The mixture was stirred an additional hour, then poured into ice water, the ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1cc2c([nH]1)CCCC2.C1CCNC1 | c1cc2c([nH]1)CCCC2 | c1cc2c([nH]1)CCCC2 | HO- | CN(C=O)C | null | null | O=C(O)c1c[nH]c2c1C(=O)CCC2.O=C1CCC(=O)N1Br>CN(C=O)C>O=C(O)c1c(Br)[nH]c2c1C(=O)CCC2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d07aee7e0ad7464fbe1b6cc8f5dbc2e5 | COc1ccc(N)cn1.O=C(O)c1c[nH]c2c1C(=O)CCC2>>COc1ccncc1NC(=O)c1c[nH]c2c1C(=O)CCC2 | COC1=NC=C(C=C1)N.[Cl-].[NH4+].O=C1C=2C(=CNC2CCC1)C(=O)O.C(C)N(CC)CC.ClC(=O)OCC>>COC1=C(C=NC=C1)NC(=O)C1=CNC=2CCCC(C12)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:8]([NH2:9])[cH:7][n:6]1.O[C:10](=[O:11])[c:12]1[cH:13][nH:14][c:15]2[c:16]1[C:17](=[O:18])[CH2:19][CH2:20][CH2:21]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][n:6][cH:7][c:8]1[NH:9][C:10](=[O:11])[c:12]1[cH:13][nH:14][c:15]2[c:16]1[C:17](=[O:18])[CH2:19][CH2:20][CH2:21]2 | COc1ccc(N)cn1.O=C(O)c1c[nH]c2c1C(=O)CCC2 | COc1ccncc1NC(=O)c1c[nH]c2c1C(=O)CCC2 | null | null | CN(C=O)C | Acylation | OtherReaction | 062edf9c9551736719f35cf8a968265a13e722f644a7f6fb57208900e319d8a8 | 25b89026811e1b3313674b1746d98ae7463bb6ef1893abcfeee44f8692f48a05 | O=C(Nc1cccnc1)c1c[nH]c2c1C(=O)CCC2 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[c:7]:1-[C:8]=[O;D1;H0:9].[C;D1;H3:10]-[#8:11]-[c;H0;D3;+0:12]1:[c:13]:[cH;D2;+0:14]:[c;H0;D3;+0:15](-[NH2;D1;+0:16]):[c:17]:[n;H0;D2;+0:18]:1>>[C;D1;H3:10]-[#8:11]-[c;H0;D3;+0:12]1:[c:13]:[cH;D2;+0:14]:[n;H0;D2;+0:18]:[c:17]:[c;H0;D3;+0:15]:1-[NH;D2;+0:16]-[C;... | 19.6 | [{"value": 19.6, "product": "COC1=C(C=NC=C1)NC(=O)C1=CNC=2CCCC(C12)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a stirring solution of 4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid (179 mg, 1 mmol) and triethylamine (293 μl, 2.1 mmol) in N,N-dimethylformamide (3 mL) at 0° C. was added ethyl chloroformate (191 μl, 2 mmol). After stirring an additional 30 minutes, a solution of 2-methoxy-5-amino-pyridine (216 mg, 2 mmol)... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether.Primary amine | Ether.Secondary amide | c1ccncc1 | c1ccncc1 | c1ccncc1.c1cc2c([nH]1)CCCC2 | HO- | CN(C=O)C | null | 0.5 | COc1ccc(N)cn1.O=C(O)c1c[nH]c2c1C(=O)CCC2>CN(C=O)C>COc1ccncc1NC(=O)c1c[nH]c2c1C(=O)CCC2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2a631a89ec7e4caea3676f4cb6dcf4c2 | O=C(O)c1cc2ccccc2c(Cc2c(O)c(C(=O)O)cc3ccccc23)c1O>>O=C(O)c1cc2ccccc2c(Cc2c(O)c(C(=O)O)cc3ccccc23)c1O | FC1=CC2=C(C(=NO2)C2CCN(CC2)CCC2=C(N=C3N(C2=O)CCCC3)C)C=C1.C=1C=CC=2C(C1)=CC(=C(C2CC3=C4C=CC=CC4=CC(=C3O)C(=O)O)O)C(=O)O>>C(C1=C(C(=CC2=CC=CC=C12)C(=O)O)O)C1=C(C(=CC2=CC=CC=C12)C(=O)O)O.FC1=CC2=C(C(=NO2)C2CCN(CC2)CCC2=C(N=C3N(C2=O)CCCC3)C)C=C1 | [O:31]=[C:32]([OH:33])[c:34]1[cH:35][c:36]2[cH:37][cH:38][cH:39][cH:40][c:41]2[c:42]([CH2:43][c:44]2[c:45]([OH:46])[c:47]([C:48](=[O:49])[OH:50])[cH:51][c:52]3[cH:53][cH:54][cH:55][cH:56][c:57]23)[c:58]1[OH:59]>>[O:31]=[C:32]([OH:33])[c:34]1[cH:35][c:36]2[cH:37][cH:38][cH:39][cH:40][c:41]2[c:42]([CH2:43][c:44]2[c:45]([... | O=C(O)c1cc2ccccc2c(Cc2c(O)c(C(=O)O)cc3ccccc23)c1O | O=C(O)c1cc2ccccc2c(Cc2c(O)c(C(=O)O)cc3ccccc23)c1O | null | null | CN(C=O)C.C(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc2c(Cc3cccc4ccccc34)cccc2c1 | null | 81 | [{"value": 81.0, "product": "C(C1=C(C(=CC2=CC=CC=C12)C(=O)O)O)C1=C(C(=CC2=CC=CC=C12)C(=O)O)O.FC1=CC2=C(C(=NO2)C2CCN(CC2)CCC2=C(N=C3N(C2=O)CCCC3)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.8, "product": "C(C1=C(C(=CC2=CC=CC=C12)C(=O)O)O)C1=C(C(=CC2=CC=CC=C12)C(=O)O)O.FC1=CC2=C(C(=NO2)C2CCN(CC2... | null | null | 3 | HOUR | A solution of 3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (0.048mol) in ethanol (600ml) was added to a solution of pamoic acid (0.048mol) in N,N-dimethylformamide (400ml). The mixture was stirred for 3 hours. The resulting precipitate was fil... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccc2ccccc2c1.c1ccc2ccccc2c1 | null | CN(C=O)C.C(C)O | null | 3 | O=C(O)c1cc2ccccc2c(Cc2c(O)c(C(=O)O)cc3ccccc23)c1O>CN(C=O)C.C(C)O>O=C(O)c1cc2ccccc2c(Cc2c(O)c(C(=O)O)cc3ccccc23)c1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2a0bdad4b0df4772b53e846d39972e90 | CN.COc1ccncc1[N+](=O)[O-]>>CNc1ccncc1[N+](=O)[O-] | COC1=C(C=NC=C1)[N+](=O)[O-].CN>>CNC1=C(C=NC=C1)[N+](=O)[O-] | [CH3:1][NH2:2].CO[c:3]1[cH:4][cH:5][n:6][cH:7][c:8]1[N+:9](=[O:10])[O-:11]>>[CH3:1][NH:2][c:3]1[cH:4][cH:5][n:6][cH:7][c:8]1[N+:9](=[O:10])[O-:11] | CN.COc1ccncc1[N+](=O)[O-] | CNc1ccncc1[N+](=O)[O-] | null | null | CCO | Functional Group Addition | Displacement of ethoxy group by primary amine | 1b6e37a6b43512a16a35031953e0a0d8c6f84b172d3d629d1978aef4bcae6d28 | 0c0f392163842ed15dcbc1e41d4bd6239c42af0df98101681b3613b490f6c196 | c1ccncc1 | C-O-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[#7;+:7].[C;D1;H3:8]-[NH2;D1;+0:9]>>[#7;+:7]-[c:6]1:[c:5]:[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:9]-[C;D1;H3:8] | 88 | [{"value": 88.0, "product": "CNC1=C(C=NC=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | 0.5 | HOUR | 4-Methoxy-3-nitropyridine (8.17 g, 53.0 mmol) was transferred to a bomb in EtOH (5-10 mL). To this was added a solution of methylamine in EtOH (26.4 mL, 8.03M, 0.212 mol). The bomb was sealed and lowered into an oil bath at 120° C. The bath temperature fell to 90° C. and remained that way for 2 hours. The temperature w... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1 | HO- | CCO | 140 | 0.5 | CN.COc1ccncc1[N+](=O)[O-]>CCO>CNc1ccncc1[N+](=O)[O-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6c6336c7aeca4c6480e93df00f4ca622 | CNc1ccnc(Cl)c1N>>Cn1cnc2c(Cl)nccc21 | NC=1C(=NC=CC1NC)Cl.C(OCC)(OCC)OCC>>ClC1=NC=CC2=C1N=CN2C | [CH3:1][NH:2][c:11]1[c:5]([NH2:4])[c:6]([Cl:7])[n:8][cH:9][cH:10]1>>[CH3:1][n:2]1[cH:3][n:4][c:5]2[c:6]([Cl:7])[n:8][cH:9][cH:10][c:11]12 | CNc1ccnc(Cl)c1N | Cn1cnc2c(Cl)nccc21 | null | OS(=O)(=O)O | null | Aromatic Heterocycle Formation | OtherReaction | cde0e949a8b76493092030314e6786137ffe69e18d01b7a20c1ea70814767ca9 | c12bf4e666f812d0e692aca3756678364265d1c8b3469e9563c84f9ed1df94d2 | c1cc2[nH]cnc2cn1 | [C;D1;H3:1]-[NH;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7](-[Cl;D1;H0:8]):[c:9]:1-[NH2;D1;+0:10]>>[C;D1;H3:1]-[n;H0;D3;+0:2]1:[c:11]:[n;H0;D2;+0:10]:[c:9]2:[c:3]:1:[c:4]:[c:5]:[#7;a:6]:[c:7]:2-[Cl;D1;H0:8] | 91.1 | [{"value": 91.0, "product": "ClC1=NC=CC2=C1N=CN2C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.1, "product": "ClC1=NC=CC2=C1N=CN2C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 22.5 | MINUTE | To a heterogeneous mixture of 3-amino-2-chloro-4-methylaminopyridine (5.9 g, 37 mmol) and triethyl orthoformate (12.92 mL, 87.2 mmol) was added 5 drops of conc. H2SO4. A short path distillation apparatus was attached. The reaction flask was lowered into a hot oil bath and stirred at 110° C. to 190° C. The time spent he... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine | null | c1ccncc1 | c1nccc2[nH]cnc12 | c1nccc2[nH]cnc12 | Other | OS(=O)(=O)O | null | 0.375 | CNc1ccnc(Cl)c1N>OS(=O)(=O)O>Cn1cnc2c(Cl)nccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ee77b780e0524603be88a42bd2c29021 | Clc1nccc2c1ncn2Cc1ccccc1.OC1CN2CCC1CC2>>c1ccc(Cn2cnc3c(OC4CN5CCC4CC5)nccc32)cc1 | Cl.C(C1=CC=CC=C1)N1C=NC=2C(=NC=CC21)Cl.N12CC(C(CC1)CC2)O>>C(C1=CC=CC=C1)N1C=NC=2C(=NC=CC21)OC2CN1CCC2CC1 | Cl[c:10]1[c:9]2[n:8][cH:7][n:6]([CH2:5][c:4]3[cH:3][cH:2][cH:1][cH:25][cH:24]3)[c:23]2[cH:22][cH:21][n:20]1.[OH:11][CH:12]1[CH2:13][N:14]2[CH2:15][CH2:16][CH:17]1[CH2:18][CH2:19]2>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][n:6]2[cH:7][n:8][c:9]3[c:10]([O:11][CH:12]4[CH2:13][N:14]5[CH2:15][CH2:16][CH:17]4[CH2:18][CH2:19]5)[n:20]... | Clc1nccc2c1ncn2Cc1ccccc1.OC1CN2CCC1CC2 | c1ccc(Cn2cnc3c(OC4CN5CCC4CC5)nccc32)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | d510fc65f8b7485b1b317b1951619cd8c9b86d2eb6369223c4ea880f78139f54 | 1f70dbbaebc288b3a5d3f37803812d9d22b151831cd4b8351080508554b19875 | c1ccc(Cn2cnc3c(OC4CN5CCC4CC5)nccc32)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6](-[C:7]):[c:8]:[#7;a:9]:[c:10]:2:1.[#7:11]-[C:12]-[C:13](-[OH;D1;+0:14])-[C:15]>>[#7:11]-[C:12]-[C:13](-[O;H0;D2;+0:14]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6](-[C:7]):[c:8]:[#7;a:9]:[c:10]:2:1)-[C:15] | 48.6 | [{"value": 39.0, "product": "C(C1=CC=CC=C1)N1C=NC=2C(=NC=CC21)OC2CN1CCC2CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.6, "product": "C(C1=CC=CC=C1)N1C=NC=2C(=NC=CC21)OC2CN1CCC2CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1, 1-benzyl-4-chloro-1H-imidazo[4,5-c]pyridine (0.78 g, 3.2 mmol) was treated with 3-quinuclidinol (0.44 g, 3.5 mmol) to give 0.52 g (39%) of the title compound as the hydrochloride, 2.5 hydrate: mp 162°-183° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary alcohol | Ether | c1nccc2nc[nH]c12 | c1nccc2[nH]cnc12 | c1ccccc1.c1nccc2[nH]cnc12.C1CN2CCC1CC2 | HCl | null | null | null | Clc1nccc2c1ncn2Cc1ccccc1.OC1CN2CCC1CC2>>c1ccc(Cn2cnc3c(OC4CN5CCC4CC5)nccc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ba5fcf5d0a3744acbef08bc1f8e5f3b4 | CCN1CCCC(=O)C1.Clc1nccc2c1ncn2Cc1ccccc1>>CCN1CCCC(O)(c2nc3c(Cl)nccc3n2Cc2ccccc2)C1 | C(C1=CC=CC=C1)N1C=NC=2C(=NC=CC21)Cl.C(C)N1CC(CCC1)=O>>C(C1=CC=CC=C1)N1C(=NC=2C(=NC=CC21)Cl)C2(CN(CCC2)CC)O | [CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][CH2:6][C:7](=[O:8])[CH2:26]1.[cH:9]1[n:10][c:11]2[c:12]([Cl:13])[n:14][cH:15][cH:16][c:17]2[n:18]1[CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][CH2:6][C:7]([OH:8])([c:9]2[n:10][c:11]3[c:12]([Cl:13])[n:14][cH:15][cH:16][c:17]3[n:18]2[CH2:19][c:... | CCN1CCCC(=O)C1.Clc1nccc2c1ncn2Cc1ccccc1 | CCN1CCCC(O)(c2nc3c(Cl)nccc3n2Cc2ccccc2)C1 | null | null | null | C-C Coupling | OtherReaction | 51893305fef8a4ec827f5bdef5a4f64a6e3b7fa7dc4beba97bf8178a22bfcab2 | 454f67ba8644982dc9f605915a0f36178771eadaffb50d3f1e0f17f2b6fdeb10 | c1ccc(Cn2c(C3CCCNC3)nc3cnccc32)cc1 | [#7;a:1]:[c:2]:[c:3]1:[#7;a:4]:[cH;D2;+0:5]:[#7;a:6](-[C:7]):[c:8]:1.[C:9]-[#7:10]1-[C:11]-[C;H0;D3;+0:12](=[O;H0;D1;+0:13])-[C:14]-[C:15]-[C:16]-1>>[#7;a:1]:[c:2]:[c:3]1:[#7;a:4]:[c;H0;D3;+0:5](-[C;H0;D4;+0:12]2(-[OH;D1;+0:13])-[C:11]-[#7:10](-[C:9])-[C:16]-[C:15]-[C:14]-2):[#7;a:6](-[C:7]):[c:8]:1 | null | [] | null | null | null | null | Following the procedure of Example 13 and using 1-benzyl-4-chloro-1H-imidazo[4,5-c]pyridine (0.60 g, 2.5 mmol) and (0.36 g, 2.8 mmol) of N-ethyl-3-piperidone gave the free base of the title compound which was purified by flash chromatography on silica gel eluting with EtOAc to give, after preparation of the salt, the d... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol | C1CC[NH]CC1.c1nccc2nc[nH]c12 | C1CC[NH]CC1.c1nc2ccncc2[nH]1 | C1CC[NH]CC1.c1nc2ccncc2[nH]1.c1ccccc1 | null | null | null | null | CCN1CCCC(=O)C1.Clc1nccc2c1ncn2Cc1ccccc1>>CCN1CCCC(O)(c2nc3c(Cl)nccc3n2Cc2ccccc2)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-95ae114a7a1047af99591a70a44e39c6 | CSc1nccc(Cl)n1.OCC(F)(F)F>>CSc1nccc(OCC(F)(F)F)n1 | FC(CO)(F)F.ClC1=NC(=NC=C1)SC.C([O-])([O-])=O.[K+].[K+]>>CSC1=NC=CC(=N1)OCC(F)(F)F | Cl[c:7]1[cH:6][cH:5][n:4][c:3]([S:2][CH3:1])[n:14]1.[OH:8][CH2:9][C:10]([F:11])([F:12])[F:13]>>[CH3:1][S:2][c:3]1[n:4][cH:5][cH:6][c:7]([O:8][CH2:9][C:10]([F:11])([F:12])[F:13])[n:14]1 | CSc1nccc(Cl)n1.OCC(F)(F)F | CSc1nccc(OCC(F)(F)F)n1 | null | null | CN(C)C=O.O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a445000eb5ed501274d93689ad5b9d45095af02deca02b6b541c8a834890a276 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1cncnc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#16:4]):[#7;a:5]:[c:6]:[c:7]:1.[F;D1;H0:8]-[C:9](-[F;D1;H0:10])(-[F;D1;H0:11])-[C:12]-[OH;D1;+0:13]>>[#16:4]-[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:13]-[C:12]-[C:9](-[F;D1;H0:8])(-[F;D1;H0:10])-[F;D1;H0:11]):[c:7]:[c:6]:[#7;a:5]:1 | 103 | [{"value": 103.0, "product": "CSC1=NC=CC(=N1)OCC(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 64 | HOUR | To a solution of 4-chloro-2-methylthiopyrimidine (16.0 g) and potassium carbonate (27.6 g) in DMF (90 ml) at 0° C., was added with stirring a solution of 2,2,2-trifluoroethanol (10.0 g) in DMF (10 ml). Stirring was continued for 64 hours, then the reaction mixture was diluted with water and extracted with ether (3×150 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cncnc1 | c1cncnc1 | c1cncnc1 | HCl | CN(C)C=O.O | null | 64 | CSc1nccc(Cl)n1.OCC(F)(F)F>CN(C)C=O.O>CSc1nccc(OCC(F)(F)F)n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-47babce885794c6582621c55f5fc99d7 | CSc1nccc(OCC(F)(F)F)n1.O=S([O-])S(=O)(=O)[O-].[O]=[Mn](=[O])(=[O])[O-]>>CS(=O)(=O)c1nccc(OCC(F)(F)F)n1 | CSC1=NC=CC(=N1)OCC(F)(F)F.[Mn](=O)(=O)(=O)[O-].[K+].C(C)(=O)O.S(=O)(=O)([O-])S(=O)[O-].[Na+].[Na+]>>CS(=O)(=O)C1=NC=CC(=N1)OCC(F)(F)F | [CH3:1][S:2][c:5]1[n:6][cH:7][cH:8][c:9]([O:10][CH2:11][C:12]([F:13])([F:14])[F:15])[n:16]1.O=S([O-])S(=O)([O-])=[O:4].[O]=[Mn](=[O])([O-])=[O:3]>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[n:6][cH:7][cH:8][c:9]([O:10][CH2:11][C:12]([F:13])([F:14])[F:15])[n:16]1 | CSc1nccc(OCC(F)(F)F)n1.O=S([O-])S(=O)(=O)[O-].[O]=[Mn](=[O])(=[O])[O-] | CS(=O)(=O)c1nccc(OCC(F)(F)F)n1 | null | null | O | Oxidation | OtherReaction | 20dd6d48007b4fe7cd760226f21413eb5e71e6468db112596c2e7ea4858c8ac1 | 5cedc1bf0f43f21d78a249521ecfcec19fc5ac4895c41eed0e84f0c2618149fa | c1cncnc1 | O=S(-[O-])-S(=O)(-[O-])=[O;H0;D1;+0:1].[C;D1;H3:2]-[S;H0;D2;+0:3]-[c:4](:[#7;a:5]:[c:6]):[#7;a:7]:[c:8].[O-]-[Mn](=[O;H0;D1;+0:9])(=[O])=[O]>>[C;D1;H3:2]-[S;H0;D4;+0:3](=[O;H0;D1;+0:9])(=[O;H0;D1;+0:1])-[c:4](:[#7;a:5]:[c:6]):[#7;a:7]:[c:8] | 87 | [{"value": 87.0, "product": "CS(=O)(=O)C1=NC=CC(=N1)OCC(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2-methylthio-4-(2,2,2-trifluoroethoxy)pyrimidine (1.0 g) in glacial acetic acid (20 ml) at 15° C. was added a solution of potassium permanganate (2.4 g) in water (75 ml). When the addition was complete a solution of sodium metabisulphite (10% aqueous) was added until a clear solution was obtained. The ... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfone | null | null | c1cncnc1 | Other | O | null | null | CSc1nccc(OCC(F)(F)F)n1.O=S([O-])S(=O)(=O)[O-].[O]=[Mn](=[O])(=[O])[O-]>O>CS(=O)(=O)c1nccc(OCC(F)(F)F)n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8d66976050a242adaad6949712ee0b51 | BrC1CCCC1.COc1ccc(C=O)cc1O>>COc1ccc(C=O)cc1OC1CCCC1 | C([O-])([O-])=O.[Cs+].[Cs+].OC=1C=C(C=O)C=CC1OC.C1(CCCC1)Br.C1(CCCC1)Br.C([O-])([O-])=O.[Cs+].[Cs+]>>C1(CCCC1)OC=1C=C(C=O)C=CC1OC | Br[CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[O:8])[cH:9][c:10]1[OH:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[O:8])[cH:9][c:10]1[O:11][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1 | BrC1CCCC1.COc1ccc(C=O)cc1O | COc1ccc(C=O)cc1OC1CCCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | b21417a59456fdb6c9e74dab1ba6f82edc34a079e35c8c3647ac7fef47b6d270 | cf768afb66ed5041aefdce1fa6d1e40995a1ab7c4b4a4ca47544fe49ee1e629f | c1ccc(OC2CCCC2)cc1 | Br-[CH;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1.[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[O;H0;D2;+0:6]-[CH;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1):[c:9] | 89.4 | [{"value": 89.4, "product": "C1(CCCC1)OC=1C=C(C=O)C=CC1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | Caesium carbonate (214 g, 0.66 mol) was added to a mixture of 3-hydroxy-4-methoxybenzaldehyde (100 g, 0.66 mol) and cyclopentyl bromide (98 g, 0.66 mol) in anhydrous DMF (50 ml). The reaction mixture was stirred at RT for 16 h then treated with a further portion of cyclopentyl bromide (98 g, 0.66 mol) and caesium carbo... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic alcohol | Ether | C1CCCC1 | C1CCCC1 | c1ccccc1.C1CCCC1 | HBr | CN(C)C=O | null | 16 | BrC1CCCC1.COc1ccc(C=O)cc1O>CN(C)C=O>COc1ccc(C=O)cc1OC1CCCC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-96b5709519a5432ab5539f7faa641c73 | BrOC1CCCC1.COc1ccc(CO)cc1O>>COc1ccc(CO)cc1OC1CCCC1 | C([O-])([O-])=O.[Cs+].[Cs+].OC=1C=C(CO)C=CC1OC.[I-].[Na+].C1(CCCC1)OBr>>C1(CCCC1)OC=1C=C(CO)C=CC1OC | BrO[CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][OH:8])[cH:9][c:10]1[OH:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][OH:8])[cH:9][c:10]1[O:11][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1 | BrOC1CCCC1.COc1ccc(CO)cc1O | COc1ccc(CO)cc1OC1CCCC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1b0b141bf6b317fb3f4853d99c0e21f208620be70a498da9a42860eb95c70530 | 0f0966e3597a58033417ecee71659f4d0c082f95d46b1e52c95541e6e4a59086 | c1ccc(OC2CCCC2)cc1 | Br-O-[CH;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1.[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[O;H0;D2;+0:6]-[CH;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1):[c:9] | 35.8 | [{"value": 35.8, "product": "C1(CCCC1)OC=1C=C(CO)C=CC1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | From 3-hydroxy-4-methoxybenzyl alcohol (50 g, 0.324 mol), cyclopentyloxybromide (70 ml, 0.648 mol), caesium carbonate (72.83 g, 0.222 mol) and sodium iodide (5.63 g, 0.037 mol). Chromatography (SiO2 ; EtOAc-C6H14, 1:3) to yield the title compound (25.782 g). (Found C, 69.92; H, 8.18. C13H18O3 requires C, 70.25; H, 8.16... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether | C1CCCC1 | C1CCCC1 | c1ccccc1.C1CCCC1 | HBr | null | null | null | BrOC1CCCC1.COc1ccc(CO)cc1O>>COc1ccc(CO)cc1OC1CCCC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ec4f0b3532d0429bb5eeb02f388b1e94 | CI.Clc1cncc(Cl)c1>>Cc1c(Cl)cncc1Cl | ClC=1C=NC=C(C1)Cl.[Li+].CC(C)[N-]C(C)C.C(O)([O-])=O.[Na+].IC>>ClC=1C=NC=C(C1C)Cl | I[CH3:1].[cH:2]1[c:3]([Cl:4])[cH:5][n:6][cH:7][c:8]1[Cl:9]>>[CH3:1][c:2]1[c:3]([Cl:4])[cH:5][n:6][cH:7][c:8]1[Cl:9] | CI.Clc1cncc(Cl)c1 | Cc1c(Cl)cncc1Cl | null | null | ClCCl.C1CCOC1 | C-C Coupling | Methylation with MeI_aryl | d4dc1d398fcb789be26f861c3ffb23cfce3504c400401ddf0ee0bd40e14a762b | 410ec9b1cc243569e4ff568c248f0b402403802e002b4018f576af3f6960507b | c1ccncc1 | I-[CH3;D1;+0:1].[Cl;D1;H0:2]-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[c:7](-[Cl;D1;H0:8]):[cH;D2;+0:9]:1>>[CH3;D1;+0:1]-[c;H0;D3;+0:9]1:[c:3](-[Cl;D1;H0:2]):[c:4]:[#7;a:5]:[c:6]:[c:7]:1-[Cl;D1;H0:8] | 53 | [{"value": 53.0, "product": "ClC=1C=NC=C(C1C)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | 3,5-Dichloropyridine (2.04 g, 13.5 mmol) in THF (5 ml) was added dropwise to a solution of LDA [prepared from diisopropylamine (1.9 ml, 13.5 mmol) and n-butyllithium (1.6M, 8.4 ml, 13.5 mmol)] in THF (25 ml) at -70° C. After stirring at this temperature for 5 min, iodomethane (0.85 ml, 13.5 mmol) was added and the reac... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccncc1 | c1ccncc1 | c1ccncc1 | HI | ClCCl.C1CCOC1 | null | 0.083333 | CI.Clc1cncc(Cl)c1>ClCCl.C1CCOC1>Cc1c(Cl)cncc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-346c438e3d4843a0b0aa5ffa14cf7153 | CCCCCC.CCOC(C)=O.CCOC(C)=O.CO.Cc1ccncc1.[Li][CH2]CCC.c1ccncc1>>COc1ccc(C(O)Cc2ccncc2)cc1OC1CCCC1 | CCOC(=O)C.CCCCCC.N1=CC=CC=C1.[H][H].CCOC(=O)C.CO.CC1=CC=NC=C1.C(CCC)[Li]>>C1(CCCC1)OC=1C=C(C=CC1OC)C(CC1=CC=NC=C1)O | CCCCC[CH3:20].CCOC(C)=[O:18].C[CH2:3]O[C:7](C)=[O:8].[CH3:1][OH:2].[CH3:9][c:10]1[cH:11][cH:12][n:13][cH:14][cH:15]1.[Li][CH2:21][CH2:22][CH2:23][CH3:19].n1[cH:4][cH:5][cH:6][cH:16][cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([OH:8])[CH2:9][c:10]2[cH:11][cH:12][n:13][cH:14][cH:15]2)[cH:16][c:17]1[O:18][CH:19]1[... | CCCCCC.CCOC(C)=O.CCOC(C)=O.CO.Cc1ccncc1.[Li][CH2]CCC.c1ccncc1 | COc1ccc(C(O)Cc2ccncc2)cc1OC1CCCC1 | null | null | N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | adfa02693bcf38d14fdf3d4325c395df0c5e1ead96f8af37b6205e6565fd3699 | eaed0ec2e18ddd7689918b523da6af01c4c12f36db516a28cad5374c79aa54fd | c1cc(CCc2ccncc2)cc(OC2CCCC2)c1 | C-C-C-C-C-[CH3;D1;+0:1].C-C-O-C(-C)=[O;H0;D1;+0:2].C-[CH2;D2;+0:3]-O-[C;H0;D3;+0:4](-C)=[O;H0;D1;+0:5].[C;D1;H3:6]-[OH;D1;+0:7].[CH3;D1;+0:8]-[C:9]-[C:10]-[CH2;D2;+0:11]-[Li].[CH3;D1;+0:12]-[c:13]1:[c:14]:[c:15]:[#7;a:16]:[c:17]:[c:18]:1.[c:19]1:[cH;D2;+0:20]:n:[cH;D2;+0:21]:[c:22]:[cH;D2;+0:23]:1>>[C;D1;H3:6]-[O;H0;D2... | null | [] | null | null | null | null | From 4-methylpyridine (3.00 g, 32.1 mmol); n-butyllithium (32.1 mmol), and Intermediate 1 (6.82 g, 31.0 mmol). The crude product was subject to chromatography [SiO2 ; EtOAc-hexane, 3:2 (500 ml) to 4:1 (1000 ml) then EtOAc-methanol 9:1 (1500 ml)] to afford the title compound (9.68 g) as fine white needles m.p. 97°-101° ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Methanol.Alkyl lithium | Ether.Ether.Secondary alcohol | c1ccncc1 | c1ccccc1.C1CCCC1 | c1ccccc1.c1ccncc1.C1CCCC1 | HO-.Li | N1=CC=CC=C1 | null | null | CCCCCC.CCOC(C)=O.CCOC(C)=O.CO.Cc1ccncc1.[Li][CH2]CCC.c1ccncc1>N1=CC=CC=C1>COc1ccc(C(O)Cc2ccncc2)cc1OC1CCCC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-71da5db547d042afaa9286f9adab88a0 | COc1ccc(-c2ccccc2[P+](C)(c2ccccc2)c2ccccc2)cc1OC1CCCC1.O=Cc1ccncc1>>COc1ccc(/C=C\c2ccncc2)cc1OC1CCCC1 | [O-]CC.[Na+].N1=CC=C(C=C1)C=O.[Cl-].C1(CCCC1)OC=1C=C(C=CC1OC)C1=C(C=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C>>C1(CCCC1)OC=1C=C(C=CC1OC)\C=C/C1=CC=NC=C1 | C[P+](c1ccccc1)(c1ccccc1)c1cccc[c:7]1-[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:16]([O:17][CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22]2)[cH:15]1.O=[CH:8][c:9]1[cH:10][cH:11][n:12][cH:13][cH:14]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](/[CH:7]=[CH:8]\[c:9]2[cH:10][cH:11][n:12][cH:13][cH:14]2)[cH:15][c:16]1[O:17][CH:18]1[CH2:19][... | COc1ccc(-c2ccccc2[P+](C)(c2ccccc2)c2ccccc2)cc1OC1CCCC1.O=Cc1ccncc1 | COc1ccc(/C=C\c2ccncc2)cc1OC1CCCC1 | null | null | C(C)O | C-C Coupling | OtherReaction | cb5f277ac55a0e763ef643becc05f1522019cc4161daceb249ed2d634b78153b | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | C(=C\c1cccc(OC2CCCC2)c1)\c1ccncc1 | C-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].O=[CH;D2;+0:7]-[c:8]1:[c:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:1>>[c:4]:[c:3]:[c;H0;D3;+0:2](/[CH;D2;+0:1]=[CH;D2;+0:7]\[c:8]1:[c:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:1):[c:5]:[c:6] | 11.9 | [{"value": 11.9, "product": "C1(CCCC1)OC=1C=C(C=CC1OC)\\C=C/C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of sodium ethoxide [prepared from sodium (0.10 g, 4.50 mmol)] in ethanol (50 ml) was added over 5 min to a stirred mixture of 4-pyridine carboxaldehyde (0.44 g, 4.10 mmol) and (3-cyclopentyloxy-4-methoxyphenyl)-methyltriphenylphosphonium chloride (2.00 g, 4.08 g) in ethanol (30 ml). After 2h, the reaction mi... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccccc1.c1ccncc1.C1CCCC1 | HO- | C(C)O | null | null | COc1ccc(-c2ccccc2[P+](C)(c2ccccc2)c2ccccc2)cc1OC1CCCC1.O=Cc1ccncc1>C(C)O>COc1ccc(/C=C\c2ccncc2)cc1OC1CCCC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a811a98a5e964e1b95e931e2733e70ca | CC(=O)COc1ccc(C#N)cc1.[NH4+]>>CC(N)COc1ccc(C#N)cc1 | C(C)(=O)[O-].[NH4+].C(#N)[BH3-].[Na+].C(#N)C1=CC=C(OCC(C)=O)C=C1>>C(#N)C1=CC=C(OCC(C)N)C=C1 | O=[C:2]([CH3:1])[CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([C:10]#[N:11])[cH:12][cH:13]1.[NH4+:3]>>[CH3:1][CH:2]([NH2:3])[CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([C:10]#[N:11])[cH:12][cH:13]1 | CC(=O)COc1ccc(C#N)cc1.[NH4+] | CC(N)COc1ccc(C#N)cc1 | null | null | CO | Functional Group Interconversion | OtherReaction | 14af499c4b742b1ab2135a986a4f7f4e6dda0ad50987736be8cf00d531c63192 | 2ef9e3e9915394571ec6196ff6ea06bca9f3dff8c6f6f43c81edc876014a94a5 | c1ccccc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[#8:4].[NH4+;D0:5]>>[#8:4]-[C:3]-[CH;D3;+0:1](-[C;D1;H3:2])-[NH2;D1;+0:5] | 27.8 | [{"value": 19.0, "product": "C(#N)C1=CC=C(OCC(C)N)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 27.8, "product": "C(#N)C1=CC=C(OCC(C)N)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 293 g of ammonium acetate and 16.7 g of sodium cyanoborohydride were added to a solution containing 66.5 g of 4-cyanophenoxyacetone dissolved in 1500 mL of methanol, and the resultant mixture was stirred for 30 hours at room temperature. The reaction mixture was then concentrated under reduced pressure, and acidified w... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary amine | null | null | c1ccccc1 | HO- | CO | null | null | CC(=O)COc1ccc(C#N)cc1.[NH4+]>CO>CC(N)COc1ccc(C#N)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-765c60307caa49c8b39c2317a5db5d9f | CC(=O)COc1ccc(Cl)cc1C.[NH4+]>>Cc1cc(Cl)ccc1OCC(C)N | C(C)(=O)[O-].[NH4+].C(#N)[BH3-].[Na+].ClC1=CC(=C(OCC(C)=O)C=C1)C>>ClC1=CC(=C(OCC(C)N)C=C1)C | O=[C:11]([CH2:10][O:9][c:8]1[c:2]([CH3:1])[cH:3][c:4]([Cl:5])[cH:6][cH:7]1)[CH3:12].[NH4+:13]>>[CH3:1][c:2]1[cH:3][c:4]([Cl:5])[cH:6][cH:7][c:8]1[O:9][CH2:10][CH:11]([CH3:12])[NH2:13] | CC(=O)COc1ccc(Cl)cc1C.[NH4+] | Cc1cc(Cl)ccc1OCC(C)N | null | null | CO | Functional Group Interconversion | OtherReaction | 14af499c4b742b1ab2135a986a4f7f4e6dda0ad50987736be8cf00d531c63192 | 2ef9e3e9915394571ec6196ff6ea06bca9f3dff8c6f6f43c81edc876014a94a5 | c1ccccc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[#8:4].[NH4+;D0:5]>>[#8:4]-[C:3]-[CH;D3;+0:1](-[C;D1;H3:2])-[NH2;D1;+0:5] | 81 | [{"value": 81.0, "product": "ClC1=CC(=C(OCC(C)N)C=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.3, "product": "ClC1=CC(=C(OCC(C)N)C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 120 g of ammonium acetate and 9.8 g of sodium cyanoborohydride were added to a solution containing 31 g of (4-chloro-2-methylphenoxy)acetone dissolved in 700 mL of methanol, and the resultant mixture was stirred for 20 hours at room temperature. After the reaction mixture was concentrated under reduced pressure. 180 mL... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary amine | null | null | c1ccccc1 | HO- | CO | null | 1 | CC(=O)COc1ccc(Cl)cc1C.[NH4+]>CO>Cc1cc(Cl)ccc1OCC(C)N |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-af2de60e1e754abb8358597255083dbf | CC(=O)C(C)Oc1ccc(Cl)cc1.[NH4+]>>CC(N)C(C)Oc1ccc(Cl)cc1 | C(C)(=O)[O-].[NH4+].C(#N)[BH3-].[Na+].ClC1=CC=C(OC(C(C)=O)C)C=C1>>ClC1=CC=C(OC(C(C)N)C)C=C1 | O=[C:2]([CH3:1])[CH:4]([CH3:5])[O:6][c:7]1[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]1.[NH4+:3]>>[CH3:1][CH:2]([NH2:3])[CH:4]([CH3:5])[O:6][c:7]1[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]1 | CC(=O)C(C)Oc1ccc(Cl)cc1.[NH4+] | CC(N)C(C)Oc1ccc(Cl)cc1 | null | null | CO | Functional Group Interconversion | OtherReaction | 14af499c4b742b1ab2135a986a4f7f4e6dda0ad50987736be8cf00d531c63192 | 2ef9e3e9915394571ec6196ff6ea06bca9f3dff8c6f6f43c81edc876014a94a5 | c1ccccc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C:3](-[#8:4])-[C;D1;H3:5].[NH4+;D0:6]>>[#8:4]-[C:3](-[C;D1;H3:5])-[CH;D3;+0:1](-[C;D1;H3:2])-[NH2;D1;+0:6] | 86 | [{"value": 86.0, "product": "ClC1=CC=C(OC(C(C)N)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.3, "product": "ClC1=CC=C(OC(C(C)N)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | 82 g of ammonium acetate and 6.7 g of sodium cyanoborohydride were added to a solution containing 21 g of 3-(4-chlorophenoxy)-2-butanone dissolved in 500 mL of methanol, and the reaction mixture was stirred for 20 hours at room temperature. The reaction mixture was then concentrated under reduced pressure, and 180 mL o... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary amine | null | null | c1ccccc1 | HO- | CO | null | 20 | CC(=O)C(C)Oc1ccc(Cl)cc1.[NH4+]>CO>CC(N)C(C)Oc1ccc(Cl)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c11fa99e3841426fba61a399ec0730d1 | CC(N)CO.N#Cc1ccc(Br)cc1>>CC(N)COc1ccc(C#N)cc1 | O.NC(CO)C.[H-].[Na+].BrC1=CC=C(C#N)C=C1>>C(#N)C1=CC=C(OCC(C)N)C=C1 | [CH3:1][CH:2]([NH2:3])[CH2:4][OH:5].Br[c:6]1[cH:7][cH:8][c:9]([C:10]#[N:11])[cH:12][cH:13]1>>[CH3:1][CH:2]([NH2:3])[CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([C:10]#[N:11])[cH:12][cH:13]1 | CC(N)CO.N#Cc1ccc(Br)cc1 | CC(N)COc1ccc(C#N)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 4821d6d7238522ee9ef4538c00647e855becf4de3d9c939c0cec2b01c1e5e915 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 41 | [{"value": 41.0, "product": "C(#N)C1=CC=C(OCC(C)N)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.9, "product": "C(#N)C1=CC=C(OCC(C)N)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | 50.0 g of 2-amino-1-propanol was added dropwise to a stirred mixture of 29.3 g of 60% sodium hydride and 300 mL of dimethylformamide at 0° C. After the reaction mixture was stirred for 30 minutes at 0° C. a solution containing 121.2 g of 4-bromobenzonitrile dissolved in N,N-dimethylformamide was added dropwise to the r... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | CN(C=O)C | 0 | 0.5 | CC(N)CO.N#Cc1ccc(Br)cc1>CN(C=O)C>CC(N)COc1ccc(C#N)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6d97a1bfa8604b93849d4516305a87c9 | CC(N)CO.Clc1ccncc1>>CC(N)COc1ccncc1 | NC(CO)C.[H-].[Na+].Cl.ClC1=CC=NC=C1>>CC(COC1=CC=NC=C1)N | [CH3:1][CH:2]([NH2:3])[CH2:4][OH:5].Cl[c:6]1[cH:7][cH:8][n:9][cH:10][cH:11]1>>[CH3:1][CH:2]([NH2:3])[CH2:4][O:5][c:6]1[cH:7][cH:8][n:9][cH:10][cH:11]1 | CC(N)CO.Clc1ccncc1 | CC(N)COc1ccncc1 | null | null | CN(C=O)C | 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.[C:7]-[C:8]-[OH;D1;+0:9]>>[C:7]-[C:8]-[O;H0;D2;+0:9]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1 | 30.2 | [{"value": 30.0, "product": "CC(COC1=CC=NC=C1)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 30.2, "product": "CC(COC1=CC=NC=C1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 6.2 g of 2-amino-1-propanol was added dropwise to a stirred mixture of 4.0 g of 60% sodium hydride and 50 mL of N,N-dimethylformamide at 5° C.-10° C. After the reaction mixture was stirred for 30 minutes, 12.5 g of 4-chloropyridine hydrochloride in limited amounts was added to the reaction mixture. The mixture was stir... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccncc1 | c1ccncc1 | c1ccncc1 | HCl | CN(C=O)C | null | 0.5 | CC(N)CO.Clc1ccncc1>CN(C=O)C>CC(N)COc1ccncc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ce63d85729de446eab4672445f571a2d | CC(COc1ccc(C#N)cc1)NC(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)C>>CC(COc1ccc(C#N)cc1)NC(=O)[C@@H](N)C(C)C | Cl.N#N.C(C)(C)(C)OC(=O)N[C@@H](C(C)C)C(=O)NC(COC1=CC=C(C=C1)C#N)C>>Cl.C(#N)C1=CC=C(OCC(C)NC([C@@H](N)C(C)C)=O)C=C1 | CC(C)(C)OC(=O)[NH:17][C@H:16]([C:14]([NH:13][CH:2]([CH3:1])[CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([C:9]#[N:10])[cH:11][cH:12]1)=[O:15])[CH:18]([CH3:19])[CH3:20]>>[CH3:1][CH:2]([CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([C:9]#[N:10])[cH:11][cH:12]1)[NH:13][C:14](=[O:15])[C@@H:16]([NH2:17])[CH:18]([CH3:19])[CH3:20] | CC(COc1ccc(C#N)cc1)NC(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)C | CC(COc1ccc(C#N)cc1)NC(=O)[C@@H](N)C(C)C | null | null | C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#7:6]-[C:7]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4](=[O;D1;H0:5])-[#7:6]-[C:7] | 100 | [{"value": 100.0, "product": "Cl.C(#N)C1=CC=C(OCC(C)NC([C@@H](N)C(C)C)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Hydrogen chloride gas was introduced into a solution containing 3.7 g of N2 -tert-butoxycarbonyl-N1 -[2-(4-cyanophenoxy)-1-methylethyl]-L-valinamide dissolved in 100 mL of methylene chloride for 1 hour at room temperature. After completion of the reaction, the methylene chloride was removed under reduced pressure, thus... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1 | HO- | C(Cl)Cl | null | null | CC(COc1ccc(C#N)cc1)NC(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)C>C(Cl)Cl>CC(COc1ccc(C#N)cc1)NC(=O)[C@@H](N)C(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-73e9b68ff1584a15b132a29861cc28c2 | CC(C)[C@H](NC(=O)Oc1ccccc1)C(=O)O.CC(N)COc1ccc(C#N)cc1>>CC(COc1ccc(C#N)cc1)NC(=O)[C@@H](NC(=O)Oc1ccccc1)C(C)C | C(#N)C1=CC=C(OCC(C)N)C=C1.CN1CCCCC1.O(C1=CC=CC=C1)C(=O)N[C@@H](C(C)C)C(=O)O.ClC(=O)OCC(C)C>>C(#N)C1=CC=C(OCC(C)NC([C@@H](NC(=O)OC2=CC=CC=C2)C(C)C)=O)C=C1 | O[C:14](=[O:15])[C@@H:16]([NH:17][C:18](=[O:19])[O:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1)[CH:27]([CH3:28])[CH3:29].[CH3:1][CH:2]([CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([C:9]#[N:10])[cH:11][cH:12]1)[NH2:13]>>[CH3:1][CH:2]([CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([C:9]#[N:10])[cH:11][cH:12]1)[NH:13][C:14](=[O:15])[C@@H:... | CC(C)[C@H](NC(=O)Oc1ccccc1)C(=O)O.CC(N)COc1ccc(C#N)cc1 | CC(COc1ccc(C#N)cc1)NC(=O)[C@@H](NC(=O)Oc1ccccc1)C(C)C | null | null | C(Cl)Cl.O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CNC(=O)Oc1ccccc1)NCCOc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7].[C:8]-[C:9](-[C;D1;H3:10])-[NH2;D1;+0:11]>>[C:4]-[C:3](-[#7:5]-[C:6]=[O;D1;H0:7])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:11]-[C:9](-[C:8])-[C;D1;H3:10] | 14.4 | [{"value": 14.4, "product": "C(#N)C1=CC=C(OCC(C)NC([C@@H](NC(=O)OC2=CC=CC=C2)C(C)C)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | 1.8 g of N-methylpiperidine was added to a solution containing 4.2 g of N-phenoxycarbonyl-L-valine dissolved in 100 ml of methylene chloride, at -20° C. After the mixture was stirred for 10 minutes at the same temperature. 2.4 g of isobutyl chloroformate was added to the mixture, and stirred for 1 hour at -20° C. 3.1 g... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl.O | null | 0.166667 | CC(C)[C@H](NC(=O)Oc1ccccc1)C(=O)O.CC(N)COc1ccc(C#N)cc1>C(Cl)Cl.O>CC(COc1ccc(C#N)cc1)NC(=O)[C@@H](NC(=O)Oc1ccccc1)C(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1c93b7108442465f805b25dd4eb5e4ed | CC(=O)c1nccc2ccccc12.NO>>CC(=NO)c1nccc2ccccc12 | C(C)(=O)C1=NC=CC2=CC=CC=C12.NO.C(C)(=O)[O-].[Na+].CO>>C(C)(C1=NC=CC2=CC=CC=C12)=NO | O=[C:2]([CH3:1])[c:5]1[n:6][cH:7][cH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12.[NH2:3][OH:4]>>[CH3:1][C:2](=[N:3][OH:4])[c:5]1[n:6][cH:7][cH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12 | CC(=O)c1nccc2ccccc12.NO | CC(=NO)c1nccc2ccccc12 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | b5fd91d879f097d0ef2e8e2d3ef7d2ef0195968870a9602a47b8324c601790b9 | 1a0ef15294bdb221fb8888b5d4c7fcf00473b11e53da288791d32747daa48d23 | c1ccc2cnccc2c1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[NH2;D1;+0:7]-[O;D1;H1:8]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[N;H0;D2;+0:7]-[O;D1;H1:8])-[c:3](:[c:4]):[#7;a:5]:[c:6] | 58 | [{"value": 58.0, "product": "C(C)(C1=NC=CC2=CC=CC=C12)=NO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.3, "product": "C(C)(C1=NC=CC2=CC=CC=C12)=NO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A solution of 1-acetyl-isoquinoline (3.42 g), hydroxylamine (1.53 g) and sodium acetate (2.46 g) in a 3:1 mixture of methanol:water (80 ml) was heated to reflux for 8 hours then allowed to stand for 16 hours. The reaction mixture was then poured into water and extracted with ethyl acetate. The combined extracts were dr... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Oxime | null | null | c1ccc2cnccc2c1 | HO- | O | null | 16 | CC(=O)c1nccc2ccccc12.NO>O>CC(=NO)c1nccc2ccccc12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1933fe9b9be74b32bfee65861da57c2d | N#Cc1cc2ccccc2cn1>>CC(=O)c1cc2ccccc2cn1 | C[Mg]Cl.C1=NC(=CC2=CC=CC=C12)C#N.C1CCOC1>>C(C)(=O)C=1N=CC2=CC=CC=C2C1 | N#[C:2][c:4]1[cH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[cH:12][n:13]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[cH:12][n:13]1 | N#Cc1cc2ccccc2cn1 | CC(=O)c1cc2ccccc2cn1 | null | null | null | Miscellaneous | OtherReaction | 54622de249eb9a5622e28710a02d261b08e09c3ee957106ef84a0e4751ccb30f | 957d5e0aaa82a4f5b73d699040cb2acd7f615417c9e400cbb7a63fa4c133449a | c1ccc2cnccc2c1 | N#[C;H0;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5]>>[C;D1;H3:6]-[C;H0;D3;+0:1](=[O;D1;H0:7])-[c:2](:[c:3]):[#7;a:4]:[c:5] | 14 | [{"value": 14.0, "product": "C(C)(=O)C=1N=CC2=CC=CC=C2C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Methyl magnesium chloride (2.6 ml of a 3.0M solution in THF) was added dropwise to a solution of isoquinoline-3-carbonitrile at 0°-5° C. After the addition the reaction mixture was stirred at room temperature for 1 hour, then quenched with water. Hydrochloric acid (2M aqueous solution) was added to the reaction mixture... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Ketone | null | null | c1ccc2cnccc2c1 | null | null | null | 1 | N#Cc1cc2ccccc2cn1>>CC(=O)c1cc2ccccc2cn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6886621a94c642309e84fee2699ce813 | CC(=O)c1cc2ccccc2cn1.NO>>CC(=NO)c1cc2ccccc2cn1 | C(C)(=O)C=1N=CC2=CC=CC=C2C1.NO.C(C)(=O)[O-].[Na+]>>C(C)(C=1N=CC2=CC=CC=C2C1)=NO | O=[C:2]([CH3:1])[c:5]1[cH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[cH:13][n:14]1.[NH2:3][OH:4]>>[CH3:1][C:2](=[N:3][OH:4])[c:5]1[cH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[cH:13][n:14]1 | CC(=O)c1cc2ccccc2cn1.NO | CC(=NO)c1cc2ccccc2cn1 | null | null | CO.O | Heteroatom Alkylation and Arylation | OtherReaction | b5fd91d879f097d0ef2e8e2d3ef7d2ef0195968870a9602a47b8324c601790b9 | 1a0ef15294bdb221fb8888b5d4c7fcf00473b11e53da288791d32747daa48d23 | c1ccc2cnccc2c1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[NH2;D1;+0:7]-[O;D1;H1:8]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[N;H0;D2;+0:7]-[O;D1;H1:8])-[c:3](:[c:4]):[#7;a:5]:[c:6] | 89 | [{"value": 89.0, "product": "C(C)(C=1N=CC2=CC=CC=C2C1)=NO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3-acetyl-isoquinoline (0.65 g), hydroxylamine (0.29 g) and sodium acetate (0.47 g) in a mixture of methanol (20 ml) and water (3 ml) was heated to reflux for 1.5 hours. The reaction was then poured into water and extracted with ethyl acetate. The combined extracts were dried, concentrated and triturated w... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Oxime | null | null | c1ccc2cnccc2c1 | HO- | CO.O | null | null | CC(=O)c1cc2ccccc2cn1.NO>CO.O>CC(=NO)c1cc2ccccc2cn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-25314cafe14044c4a971af24b93211f4 | CC(=O)c1nccc(-c2ccccn2)n1.NO>>CC(=NO)c1nccc(-c2ccccn2)n1 | C(C)(=O)C1=NC=CC(=N1)C1=NC=CC=C1.NO.C(C)(=O)[O-].[Na+]>>C(C)(C1=NC=CC(=N1)C1=NC=CC=C1)=NO | O=[C:2]([CH3:1])[c:5]1[n:6][cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][cH:13][cH:14][n:15]2)[n:16]1.[NH2:3][OH:4]>>[CH3:1][C:2](=[N:3][OH:4])[c:5]1[n:6][cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][cH:13][cH:14][n:15]2)[n:16]1 | CC(=O)c1nccc(-c2ccccn2)n1.NO | CC(=NO)c1nccc(-c2ccccn2)n1 | null | null | C(C)O.O | Heteroatom Alkylation and Arylation | OtherReaction | b5fd91d879f097d0ef2e8e2d3ef7d2ef0195968870a9602a47b8324c601790b9 | 1a0ef15294bdb221fb8888b5d4c7fcf00473b11e53da288791d32747daa48d23 | c1ccc(-c2ccncn2)nc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[c:3](:[#7;a:4]:[c:5]):[#7;a:6]:[c:7].[NH2;D1;+0:8]-[O;D1;H1:9]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[N;H0;D2;+0:8]-[O;D1;H1:9])-[c:3](:[#7;a:4]:[c:5]):[#7;a:6]:[c:7] | 91.1 | [{"value": 91.0, "product": "C(C)(C1=NC=CC(=N1)C1=NC=CC=C1)=NO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.1, "product": "C(C)(C1=NC=CC(=N1)C1=NC=CC=C1)=NO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-acetyl-4-(pyrid-2-yl)-pyrimidine (1.0 g), hydroxylamine (0.39 g) and sodium acetate (0.62 g) in a mixture of ethanol (10 ml) and water (2 ml) was heated to reflux for 1.5 hours. The reaction was then poured into water the precipitate filtered and washed with hexane to give 2-acetyl-4-(pyrid-2-yl)-pyrimi... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Oxime | null | null | c1cncnc1.c1ccncc1 | HO- | C(C)O.O | null | null | CC(=O)c1nccc(-c2ccccn2)n1.NO>C(C)O.O>CC(=NO)c1nccc(-c2ccccn2)n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-dd08297f1095466ea20b3117b6f50645 | CC#C[C@H](C)Oc1cc(N)c(Cl)cc1C(=O)N[C@H]1CCN(C(=O)OCC)C[C@H]1OC>>CC#C[C@H](C)Oc1cc(N)c(Cl)cc1C(=O)N[C@H]1CCNC[C@H]1OC | C(C)OC(=O)N1C[C@H]([C@H](CC1)NC(C1=C(C=C(C(=C1)Cl)N)O[C@H](C#CC)C)=O)OC.[OH-].[K+].O>>CO[C@@H]1CNCC[C@@H]1NC(C1=C(C=C(C(=C1)Cl)N)O[C@H](C#CC)C)=O | CCOC(=O)[N:21]1[CH2:20][CH2:19][C@H:18]([NH:17][C:15]([c:14]2[c:7]([O:6][C@H:4]([C:3]#[C:2][CH3:1])[CH3:5])[cH:8][c:9]([NH2:10])[c:11]([Cl:12])[cH:13]2)=[O:16])[C@H:23]([O:24][CH3:25])[CH2:22]1>>[CH3:1][C:2]#[C:3][C@H:4]([CH3:5])[O:6][c:7]1[cH:8][c:9]([NH2:10])[c:11]([Cl:12])[cH:13][c:14]1[C:15](=[O:16])[NH:17][C@H:18]... | CC#C[C@H](C)Oc1cc(N)c(Cl)cc1C(=O)N[C@H]1CCN(C(=O)OCC)C[C@H]1OC | CC#C[C@H](C)Oc1cc(N)c(Cl)cc1C(=O)N[C@H]1CCNC[C@H]1OC | null | null | CC(C)O | Reduction | Hydrogenolysis of tertiary amines | 6dc5c07be2bf2a2ccc4ff166fd44281ea50e6dda805f74758334dcde1ad7a582 | 20c36f41eeb07c3ba4437b51ba72e8ff3c22d0b27e7197b0e9af3127f331149f | O=C(NC1CCNCC1)c1ccccc1 | C-C-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 16.3 | [{"value": 16.3, "product": "CO[C@@H]1CNCC[C@@H]1NC(C1=C(C=C(C(=C1)Cl)N)O[C@H](C#CC)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2.50 g of the cis-N-(1-ethoxycarbonyl-3-methoxy-4-piperidinyl)-4-amino-5-chloro-2-((S)-1-methyl-2-butynyl)oxybenzamide prepared in the Example 7 and 4.5 g of potassium hydroxide were dissolved in 2-propanol. The obtained solution was refluxed for 1.5 hours and cooled, followed by the addition thereto of water. The resu... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccccc1.C1CCNCC1 | HO- | CC(C)O | null | null | CC#C[C@H](C)Oc1cc(N)c(Cl)cc1C(=O)N[C@H]1CCN(C(=O)OCC)C[C@H]1OC>CC(C)O>CC#C[C@H](C)Oc1cc(N)c(Cl)cc1C(=O)N[C@H]1CCNC[C@H]1OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e90e3b33efd8427982a8d67e8d113a2f | CC#C[C@H](C)Oc1cc(N)c(Cl)cc1C(=O)N[C@H]1CCNC[C@H]1OC.Fc1ccc(OCCCBr)cc1>>CC#C[C@H](C)Oc1cc(N)c(Cl)cc1C(=O)N[C@H]1CCN(CCCOc2ccc(F)cc2)C[C@H]1OC | CN(C)C=O.CO[C@@H]1CNCC[C@@H]1NC(C1=C(C=C(C(=C1)Cl)N)O[C@H](C#CC)C)=O.FC1=CC=C(OCCCBr)C=C1.C(C)N(CC)CC>>FC1=CC=C(OCCCN2C[C@H]([C@H](CC2)NC(C2=C(C=C(C(=C2)Cl)N)O[C@H](C#CC)C)=O)OC)C=C1 | [CH3:1][C:2]#[C:3][C@H:4]([CH3:5])[O:6][c:7]1[cH:8][c:9]([NH2:10])[c:11]([Cl:12])[cH:13][c:14]1[C:15](=[O:16])[NH:17][C@H:18]1[CH2:19][CH2:20][NH:21][CH2:33][C@H:34]1[O:35][CH3:36].Br[CH2:22][CH2:23][CH2:24][O:25][c:26]1[cH:27][cH:28][c:29]([F:30])[cH:31][cH:32]1>>[CH3:1][C:2]#[C:3][C@H:4]([CH3:5])[O:6][c:7]1[cH:8][c:9... | CC#C[C@H](C)Oc1cc(N)c(Cl)cc1C(=O)N[C@H]1CCNC[C@H]1OC.Fc1ccc(OCCCBr)cc1 | CC#C[C@H](C)Oc1cc(N)c(Cl)cc1C(=O)N[C@H]1CCN(CCCOc2ccc(F)cc2)C[C@H]1OC | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(NC1CCN(CCCOc2ccccc2)CC1)c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]-[C:3])-[C:7]-[C:8] | 91.8 | [{"value": 91.8, "product": "FC1=CC=C(OCCCN2C[C@H]([C@H](CC2)NC(C2=C(C=C(C(=C2)Cl)N)O[C@H](C#CC)C)=O)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 2 | HOUR | A mixture comprising 0.10 g of the cis-N-(3-methoxy-4-piperidinyl)-4-amino-5-chloro-2-((S)-1-methyl-2-butynyl)oxybenzamide, 0.07 g of 3-(4-fluorophenoxy)propyl bromide, 0.20 g of triethylamine and 10 ml of DMF was stirred at 50° C. for 2 hours and cooled. Ethyl acetate was poured into the resulting mixture. The obtaine... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1 | HBr | C(C)(=O)OCC | 50 | 2 | CC#C[C@H](C)Oc1cc(N)c(Cl)cc1C(=O)N[C@H]1CCNC[C@H]1OC.Fc1ccc(OCCCBr)cc1>C(C)(=O)OCC>CC#C[C@H](C)Oc1cc(N)c(Cl)cc1C(=O)N[C@H]1CCN(CCCOc2ccc(F)cc2)C[C@H]1OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9dc5871df86240a4b56e8af07f75976e | CC#C[C@H](C)Oc1cc(N)c(Cl)cc1C(=O)O.NC1C2CCN1CC(Cc1ccccc1)C2>>CC#C[C@H](C)Oc1cc(N)c(Cl)cc1C(=O)NC1C2CCC1CN(Cc1ccccc1)C2 | ON1N=NC2=C1C=CC=C2.NC1=CC(=C(C(=O)O)C=C1Cl)O[C@H](C#CC)C.NC1N2CC(CC1CC2)CC2=CC=CC=C2.CCN=C=NCCCN(C)C.Cl>>C(C1=CC=CC=C1)N1CC2CCC(C1)C2NC(C2=C(C=C(C(=C2)Cl)N)O[C@H](C#CC)C)=O | O[C:15]([c:14]1[c:7]([O:6][C@H:4]([C:3]#[C:2][CH3:1])[CH3:5])[cH:8][c:9]([NH2:10])[c:11]([Cl:12])[cH:13]1)=[O:16].[NH2:17][CH:18]1[CH:19]2[CH2:20][CH2:21][N:24]1[CH2:23][CH:22]([CH2:25][c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1)[CH2:32]2>>[CH3:1][C:2]#[C:3][C@H:4]([CH3:5])[O:6][c:7]1[cH:8][c:9]([NH2:10])[c:11]([Cl:12]... | CC#C[C@H](C)Oc1cc(N)c(Cl)cc1C(=O)O.NC1C2CCN1CC(Cc1ccccc1)C2 | CC#C[C@H](C)Oc1cc(N)c(Cl)cc1C(=O)NC1C2CCC1CN(Cc1ccccc1)C2 | null | null | null | Acylation | OtherReaction | c8faf4bf8d67b7818ab7b03f84d086fd40da12c61a6341532c656d89a5dd4db9 | bf57ff0584568f6455b9e238ebd2c49e1ed2227f45884308bd5a02d975532948 | O=C(NC1C2CCC1CN(Cc1ccccc1)C2)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[CH;D3;+0:7]1-[C:8]2-[C:9]-[CH2;D2;+0:10]-[N;H0;D3;+0:11]-1-[C:12]-[CH;D3;+0:13](-[CH2;D2;+0:14]-[c:15](:[c:16]):[c:17])-[CH2;D2;+0:18]-2>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[CH;D3;+0:7]1-[C:8]2-[C:9]-[CH2;D2;+0:10]-[CH;D3;+0:13]-1-[C:12]-[N;H0;D3;+... | null | [] | null | null | null | null | The condensation of 530 mg of (S)-4-amino-5-chloro-2-[(1-methyl-2-butynyl)oxy]benzoic acid with 850 mg of 8-amino-3-benzylazabicyclo[3.2.1]octane was conducted in a similar manner to that of the Example 34 by the use of WSC.HCl and 1-hydroxybenzotriazole (HOBT). The product was purified by silica gel column chromatogra... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine.Tertiary amine | Secondary amide.Tertiary amine | C1CC2CCN(C1)C2 | C1CC2C[NH]CC1C2 | c1ccccc1.C1CC2C[NH]CC1C2.c1ccccc1 | HO- | null | null | null | CC#C[C@H](C)Oc1cc(N)c(Cl)cc1C(=O)O.NC1C2CCN1CC(Cc1ccccc1)C2>>CC#C[C@H](C)Oc1cc(N)c(Cl)cc1C(=O)NC1C2CCC1CN(Cc1ccccc1)C2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3730779ac7234e61924027d44b783970 | O=CCC(F)(Cl)C(F)(F)Br.OO>>O=C(O)CC(F)(Cl)C(F)(F)Br | BrC(C(CC=O)(F)Cl)(F)F.ClC(C(Br)(F)F)(Br)F.C(=C)OCC.S(=O)([O-])S(=O)[O-].[Na+].[Na+].C([O-])(O)=O.[Na+].Cl(=O)[O-].[Na+].OO>>BrC(C(CC(=O)O)(F)Cl)(F)F | [O:1]=[CH:2][CH2:4][C:5]([F:6])([Cl:7])[C:8]([F:9])([F:10])[Br:11].O[OH:3]>>[O:1]=[C:2]([OH:3])[CH2:4][C:5]([F:6])([Cl:7])[C:8]([F:9])([F:10])[Br:11] | O=CCC(F)(Cl)C(F)(F)Br.OO | O=C(O)CC(F)(Cl)C(F)(F)Br | null | null | null | Acylation | OtherReaction | 11d630bd7a8d05707fc5eb890f030e7a5b49b94409f282ce03ce1d79527e12ed | 6fc85d54cb1f6b8147c0611acc28512113e77428616f7c82161971cc3447bea3 | null | O-[OH;D1;+0:1].[C:2]-[C:3]-[CH;D2;+0:4]=[O;D1;H0:5]>>[C:2]-[C:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[OH;D1;+0:1] | null | [] | null | null | null | null | A one pot reaction of 1-chloro-1,2-dibromotrifluoroethane (VI) with ethyl vinyl ether in the presence of sodium hydrosulfite/sodium bicarbonate followed by oxidation of the intermediate, 4-bromo-3-chloro-3,4,4-trifluorobutanal (VII), without isolaton, with sodium chlorite/hydrogen peroxide to give 4-bromo-3-chloro-3,4,... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Peroxide | Carboxylic acid | null | null | null | HO- | null | null | null | O=CCC(F)(Cl)C(F)(F)Br.OO>>O=C(O)CC(F)(Cl)C(F)(F)Br |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4d3c86752d15461798923a512c8e5d21 | O=CCC(F)(Cl)C(F)(F)Br>>OCCC(F)(Cl)C(F)(F)Br | BrC(C(CC=O)(F)Cl)(F)F.[BH4-].[Na+]>>BrC(C(CCO)(F)Cl)(F)F | [O:1]=[CH:2][CH2:3][C:4]([F:5])([Cl:6])[C:7]([F:8])([F:9])[Br:10]>>[OH:1][CH2:2][CH2:3][C:4]([F:5])([Cl:6])[C:7]([F:8])([F:9])[Br:10] | O=CCC(F)(Cl)C(F)(F)Br | OCCC(F)(Cl)C(F)(F)Br | null | null | null | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | null | [C:1]-[C:2]-[CH;D2;+0:3]=[O;H0;D1;+0:4]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[OH;D1;+0:4] | null | [] | null | null | null | null | Alternatively, the intermediate VII can be reduced with sodium borohydride without isolation to give 4-bromo-3-chloro-3,4,4-trifiuorobutanol ((IX) in high yield; or by hydrolysis of 1,4-dibromo-2-chloro-1,1,2-trifiuorobutane (XVI) to give IX. Oxidation of IX with Jones reagent to give VIII in 85% yield.
Conditions: See... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | null | null | null | null | null | O=CCC(F)(Cl)C(F)(F)Br>>OCCC(F)(Cl)C(F)(F)Br |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d5446b660e3b4561b6d68c86ee972a8c | O=C(O)CC(F)(Cl)C(F)(F)Br>>O=C(O)CC(F)=C(F)F | BrC(C(CC(=O)O)(F)Cl)(F)F>>FC(CC(=O)O)=C(F)F | Cl[C:5]([CH2:4][C:2](=[O:1])[OH:3])([F:6])[C:7](Br)([F:8])[F:9]>>[O:1]=[C:2]([OH:3])[CH2:4][C:5]([F:6])=[C:7]([F:8])[F:9] | O=C(O)CC(F)(Cl)C(F)(F)Br | O=C(O)CC(F)=C(F)F | null | [Zn] | null | Miscellaneous | OtherReaction | 221dcd72b1b25b8d0545a96bf888c2f3f10708e8af2a5f8246d07d8e1e573848 | 0edd26bddaef5eec9fa4b1247626740d6429c88823c0389badca036f448c1c14 | null | Br-[C;H0;D4;+0:1](-[F;D1;H0:2])(-[F;D1;H0:3])-[C;H0;D4;+0:4](-Cl)(-[F;D1;H0:5])-[C:6]-[C:7](=[O;D1;H0:8])-[O;D1;H1:9]>>[F;D1;H0:5]-[C;H0;D3;+0:4](-[C:6]-[C:7](=[O;D1;H0:8])-[O;D1;H1:9])=[C;H0;D3;+0:1](-[F;D1;H0:2])-[F;D1;H0:3] | null | [] | null | null | null | null | Dehalogenation of 4-bromo-3-chloro-3,4,4-trifluorobutanoic acid (VIII) with zinc using conditions analogous to those disclosed in the literature to obtain the desired 3,4,4-trifluoro-3-butenoic acid (IV); or
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide | Alkenyl halide.Alkenyl halide.Alkenyl halide | null | null | null | Br- | [Zn] | null | null | O=C(O)CC(F)(Cl)C(F)(F)Br>[Zn]>O=C(O)CC(F)=C(F)F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-785f3c16cc454b2f8882766f14740ddd | C=C(Cl)Cl.FC(F)(Br)C(F)(Cl)Br.FC(F)(Cl)C(F)(Cl)Cl.O=C[O-].O=S(=O)([O-])OOS(=O)(=O)[O-]>>O=C(O)CC(F)(Cl)C(F)(F)Br.O=C(O)CC(F)(Cl)C(F)(F)Cl | ClC(C(Br)(F)F)(Br)F.ClC(C(Cl)(F)F)(Cl)F.C(=C)(Cl)Cl.S(=O)(=O)([O-])OOS(=O)(=O)[O-].C(=O)[O-].[Na+]>>BrC(C(CC(=O)O)(F)Cl)(F)F.ClC(CC(=O)O)(C(F)(F)Cl)F | Cl[C:2](Cl)=[CH2:4].Br[C:16]([C:15]([F:10])([Br:11])[Cl:18])([F:17])[F:21].Cl[C:19]([C:5]([F:6])([Cl:7])[F:9])([F:20])[Cl:22].[O:12]=[CH:13][O-:14].O=S(=O)(OOS(=O)([O-])=[O:1])[O-:3]>>[O:1]=[C:2]([OH:3])[CH2:4][C:5]([F:6])([Cl:7])[C:8]([F:9])([F:10])[Br:11].[O:12]=[C:13]([OH:14])[CH2:15][C:16]([F:17])([Cl:18])[C:19]([F... | C=C(Cl)Cl.FC(F)(Br)C(F)(Cl)Br.FC(F)(Cl)C(F)(Cl)Cl.O=C[O-].O=S(=O)([O-])OOS(=O)(=O)[O-] | O=C(O)CC(F)(Cl)C(F)(F)Br.O=C(O)CC(F)(Cl)C(F)(F)Cl | null | null | CN(C)C=O | Acylation | OtherReaction | a01dbfefc51c3ec337949adc0141bb187602b77ae351af1f3a5d921f21690657 | a3d38ec0ef8175eed928344cc26f092d361f1e3052332cd3b73227b04c0838e4 | null | Br-[C;H0;D4;+0:1](-[F;D1;H0:2])(-[F;H0;D1;+0:3])-[C;H0;D4;+0:4](-[Br;H0;D1;+0:5])(-[Cl;H0;D1;+0:6])-[F;H0;D1;+0:7].Cl-[C;H0;D3;+0:8](-Cl)=[CH2;D1;+0:9].Cl-[C;H0;D4;+0:10](-[Cl;D1;H0:11])(-[F;D1;H0:12])-[C;H0;D4;+0:13](-[Cl;D1;H0:14])(-[F;D1;H0:15])-[F;H0;D1;+0:16].O=S(=O)(-[O-;H0;D1:17])-O-O-S(=O)(-[O-])=[O;H0;D1;+0:18... | null | [] | null | null | null | null | A one pot reaction of 1-chloro-1,2-dibromotrifluoroethane (VI) or 1,1,2-trichlorotrifiuoroethane (X) with vinylidene chloride in the presence of ammoninm persulfate/sodium formate/air in DMF to give 4-bromo-3-chloro-3,4,4-trifiuorobutanoic acid (VIII) or 3,4- dichloro-3,4,4-trifluorobutanoic acid (XI).
Conditions: See ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Alkenyl halide.Alkenyl halide.Peroxide.Vinyl | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Carboxylic acid.Carboxylic acid | null | null | null | Br- | CN(C)C=O | null | null | C=C(Cl)Cl.FC(F)(Br)C(F)(Cl)Br.FC(F)(Cl)C(F)(Cl)Cl.O=C[O-].O=S(=O)([O-])OOS(=O)(=O)[O-]>CN(C)C=O>O=C(O)CC(F)(Cl)C(F)(F)Br.O=C(O)CC(F)(Cl)C(F)(F)Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c52267ccc4ea462db1460373af993a7c | O=C(Cl)C(=O)Cl.O=C(O)CC(F)=C(F)F>>O=C(Cl)CC(F)=C(F)F | FC(CC(=O)O)=C(F)F.C(C(=O)Cl)(=O)Cl>>FC(CC(=O)Cl)=C(F)F | O=C(Cl)C(=O)[Cl:3].O[C:2](=[O:1])[CH2:4][C:5]([F:6])=[C:7]([F:8])[F:9]>>[O:1]=[C:2]([Cl:3])[CH2:4][C:5]([F:6])=[C:7]([F:8])[F:9] | O=C(Cl)C(=O)Cl.O=C(O)CC(F)=C(F)F | O=C(Cl)CC(F)=C(F)F | null | CN(C)C=O | null | Functional Group Interconversion | Alcohol to chloride_Other | 013cec2edeb273a7a148f349d36a52d99ff4e7bcf8eed78085df830088e387ac | aedb1f68dc5b7eb0583043e1125b741382b17974140a2f46554f0110e2ddc884 | null | Cl-C(=O)-C(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]-[C:5](-[F;D1;H0:6])=[C:7](-[F;D1;H0:8])-[F;D1;H0:9]>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]-[C:5](-[F;D1;H0:6])=[C:7](-[F;D1;H0:8])-[F;D1;H0:9] | null | [] | null | null | null | null | Reaction of 3,4,4-trifiuoro-3-butenoic acid (IV) with oxalyl chloride in the presence of DMF as a catalyst without any solvent to give 3,4,4-trifluoro-3-butenoyl chloride (V).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Carboxylic acid | Acyl halide | null | null | null | HCl | CN(C)C=O | null | null | O=C(Cl)C(=O)Cl.O=C(O)CC(F)=C(F)F>CN(C)C=O>O=C(Cl)CC(F)=C(F)F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e35af9d11de64be984c69f790192129f | OCCC(F)=C(F)F>>O=C(O)CC(F)=C(F)F | FC(CCO)=C(F)F.CC(=O)C.OS(=O)(=O)O.O=[Cr](=O)=O>>FC(CC(=O)O)=C(F)F | [CH2:2]([OH:3])[CH2:4][C:5]([F:6])=[C:7]([F:8])[F:9]>>[O:1]=[C:2]([OH:3])[CH2:4][C:5]([F:6])=[C:7]([F:8])[F:9] | OCCC(F)=C(F)F | O=C(O)CC(F)=C(F)F | null | null | CC(=O)C | Oxidation | Oxidation of alcohol to carboxylic acid | b709baac44a995a9a8f6386a6b5d87f98c32eb5a0636340abc1f778fae827230 | 4454822e22dc2dc24e7495385256bfce456e337c240bb764261f81dbeda1aaa1 | null | [F;D1;H0:1]-[C:2](-[C:3]-[CH2;D2;+0:4]-[O;D1;H1:5])=[C:6](-[F;D1;H0:7])-[F;D1;H0:8]>>[F;D1;H0:1]-[C:2](-[C:3]-[C;H0;D3;+0:4](=[O;D1;H0:9])-[O;D1;H1:5])=[C:6](-[F;D1;H0:7])-[F;D1;H0:8] | null | [] | null | null | null | null | The first method involves hydrolysis of 4-bromo-1,1,2-trifluoro-1-butene (II) with water in the presence of N-methyl pyrrolidinone to give 3,4,4-trifiuoro-3-buten-1-ol (III), followed by Jones oxidation under conditions not previously known. These conditions are at a temperature of about 51°-54° C. In addition, the 3,4... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Carboxylic acid | null | null | null | Other | CC(=O)C | null | null | OCCC(F)=C(F)F>CC(=O)C>O=C(O)CC(F)=C(F)F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f069e64d90a346f186352335c52bd727 | O=C(O)CC(F)(Cl)C(F)(F)Br>>O=C(O)CC(F)=C(F)F | BrC(C(CC(=O)O)(F)Cl)(F)F>>FC(CC(=O)O)=C(F)F | Cl[C:5]([CH2:4][C:2](=[O:1])[OH:3])([F:6])[C:7](Br)([F:8])[F:9]>>[O:1]=[C:2]([OH:3])[CH2:4][C:5]([F:6])=[C:7]([F:8])[F:9] | O=C(O)CC(F)(Cl)C(F)(F)Br | O=C(O)CC(F)=C(F)F | null | [Zn] | null | Miscellaneous | OtherReaction | 221dcd72b1b25b8d0545a96bf888c2f3f10708e8af2a5f8246d07d8e1e573848 | 0edd26bddaef5eec9fa4b1247626740d6429c88823c0389badca036f448c1c14 | null | Br-[C;H0;D4;+0:1](-[F;D1;H0:2])(-[F;D1;H0:3])-[C;H0;D4;+0:4](-Cl)(-[F;D1;H0:5])-[C:6]-[C:7](=[O;D1;H0:8])-[O;D1;H1:9]>>[F;D1;H0:5]-[C;H0;D3;+0:4](-[C:6]-[C:7](=[O;D1;H0:8])-[O;D1;H1:9])=[C;H0;D3;+0:1](-[F;D1;H0:2])-[F;D1;H0:3] | null | [] | null | null | null | null | In the second method the synthesis of 4-bromo-3-chloro-3,4,4-trifiuoro-butanoic acid (VIII) is followed by zinc dehalogenation to produce 3,4,4-trifiuoro-3-butenoic acid (IV). This compound is prepared by reacting 1-chloro-1,2-dibromotrifiuoroethane (VI) with ethyl vinyl ether in the presence of sodium dithionite and s... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide | Alkenyl halide.Alkenyl halide.Alkenyl halide | null | null | null | Br- | [Zn] | null | null | O=C(O)CC(F)(Cl)C(F)(F)Br>[Zn]>O=C(O)CC(F)=C(F)F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8f5c842320a64990ae9a69c2e501100d | C=C(Cl)Cl.CC(C)=O.FC(F)(Cl)C(F)(Cl)Cl.O.O=C=O>>O=C(O)CC(F)(Cl)C(F)(F)Cl.O=C(O)CC(F)=C(F)F | C(=O)=O.CC(=O)C.ClC(C(Cl)(F)F)(Cl)F.C(=C)(Cl)Cl.S(=O)(=O)([O-])OOS(=O)(=O)[O-].[NH4+].[NH4+].C(=O)[O-].[Na+].O>>ClC(CC(=O)O)(C(F)(F)Cl)F.FC(CC(=O)O)=C(F)F | Cl[C:2](Cl)=[CH2:4].C[C:13](=[O:12])[CH3:15].Cl[C:8]([F:9])([Cl:11])[C:16]([F:6])([Cl:7])[F:19].[OH2:3].[O:1]=[C:5]=[O:14]>>[O:1]=[C:2]([OH:3])[CH2:4][C:5]([F:6])([Cl:7])[C:8]([F:9])([F:10])[Cl:11].[O:12]=[C:13]([OH:14])[CH2:15][C:16]([F:17])=[C:18]([F:19])[F:20] | C=C(Cl)Cl.CC(C)=O.FC(F)(Cl)C(F)(Cl)Cl.O.O=C=O | O=C(O)CC(F)(Cl)C(F)(F)Cl.O=C(O)CC(F)=C(F)F | null | null | CN(C)C=O | Acylation | OtherReaction | 5f2040cd1bf011fd5983e5e29bff9f52325760e95a1955ac10f0a1dd4d03f23c | d63f19c40e450a1915595f0fac64cab7a5b42cacd479d7ec6bbe2a68de5ca745 | null | C-[C;H0;D3;+0:1](-[CH3;D1;+0:2])=[O;D1;H0:3].Cl-[C;H0;D3;+0:4](-Cl)=[CH2;D1;+0:5].Cl-[C;H0;D4;+0:6](-[Cl;D1;H0:7])(-[F;D1;H0:8])-[C;H0;D4;+0:9](-[Cl;H0;D1;+0:10])(-[F;H0;D1;+0:11])-[F;H0;D1;+0:12].[O;H0;D1;+0:13]=[C;H0;D2;+0:14]=[O;H0;D1;+0:15].[OH2;D0;+0:16]>>[Cl;D1;H0:7]-[C;H0;D4;+0:6](-[F;D1;H0:17])(-[F;D1;H0:8])-[C... | null | [] | null | null | 30 | MINUTE | A mixture of 1,1,2-trichlorotrifluoroethane (X) (9.37 g, 50 mmol), vinylidene chloride (4.85 g, 50 mmol), ammonium persulfate (11.41 g, 50 mmol), sodium formate (3.4 g, 50 mmol) and water (1.8 g, 0.1 mol) in DMF (80 mL) was stirred (dry-ice/acetone condensor) at room temperature with air bubbling. After 30 min, an aliq... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Alkenyl halide.Alkenyl halide.Ketone.Vinyl.Carbon dioxide | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Alkenyl halide.Alkenyl halide.Alkenyl halide.Carboxylic acid.Carboxylic acid | null | null | null | null | CN(C)C=O | null | 0.5 | C=C(Cl)Cl.CC(C)=O.FC(F)(Cl)C(F)(Cl)Cl.O.O=C=O>CN(C)C=O>O=C(O)CC(F)(Cl)C(F)(F)Cl.O=C(O)CC(F)=C(F)F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-cc001eb75d5743259d85df36a16ea38b | OCCC(F)(Cl)C(F)(F)Br>>O=C(O)CC(F)(Cl)C(F)(F)Br | C(C)(C)O.BrC(C(CCO)(F)Cl)(F)F.CC(=O)C.OS(=O)(=O)O.O=[Cr](=O)=O>>BrC(C(CC(=O)O)(F)Cl)(F)F | [CH2:2]([OH:3])[CH2:4][C:5]([F:6])([Cl:7])[C:8]([F:9])([F:10])[Br:11]>>[O:1]=[C:2]([OH:3])[CH2:4][C:5]([F:6])([Cl:7])[C:8]([F:9])([F:10])[Br:11] | OCCC(F)(Cl)C(F)(F)Br | O=C(O)CC(F)(Cl)C(F)(F)Br | null | null | C(Cl)Cl.CC(=O)C | Oxidation | Oxidation of alcohol to carboxylic acid | b709baac44a995a9a8f6386a6b5d87f98c32eb5a0636340abc1f778fae827230 | 4454822e22dc2dc24e7495385256bfce456e337c240bb764261f81dbeda1aaa1 | null | [C:1]-[C:2]-[CH2;D2;+0:3]-[O;D1;H1:4]>>[C:1]-[C:2]-[C;H0;D3;+0:3](=[O;D1;H0:5])-[O;D1;H1:4] | 85 | [{"value": 85.0, "product": "BrC(C(CC(=O)O)(F)Cl)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-bromo-3-chloro-3,4,4-trifluorobutanol (IX) (2.41 g, 10 mmol) in acetone (35 mL) was treated with Jones reagent (7.5 mL) in 10 min with stirring and cooling (ice-water bath). The mixture was then stirred at room temperature for 30 min and 0.5 mL of i-propanol was then added. The precipitated salts were r... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Carboxylic acid | null | null | null | Other | C(Cl)Cl.CC(=O)C | null | null | OCCC(F)(Cl)C(F)(F)Br>C(Cl)Cl.CC(=O)C>O=C(O)CC(F)(Cl)C(F)(F)Br |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7acdd14915da464f89faabd34f59b6eb | COc1cc(OC)nc(N)n1.O=C(Cl)CC(F)=C(F)F>>COc1cc(OC)nc(NC(=O)CC(F)=C(F)F)n1 | FC(CC(=O)Cl)=C(F)F.NC1=NC(=CC(=N1)OC)OC.C([O-])([O-])=O.[K+].[K+]>>FC(CC(=O)NC1=NC(=CC(=N1)OC)OC)=C(F)F | [CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[n:8][c:9]([NH2:10])[n:19]1.Cl[C:11](=[O:12])[CH2:13][C:14]([F:15])=[C:16]([F:17])[F:18]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[n:8][c:9]([NH:10][C:11](=[O:12])[CH2:13][C:14]([F:15])=[C:16]([F:17])[F:18])[n:19]1 | COc1cc(OC)nc(N)n1.O=C(Cl)CC(F)=C(F)F | COc1cc(OC)nc(NC(=O)CC(F)=C(F)F)n1 | null | null | ClCCl.O | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1cncnc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4](-[F;D1;H0:5])=[C:6](-[F;D1;H0:7])-[F;D1;H0:8].[NH2;D1;+0:9]-[c:10](:[#7;a:11]:[c:12]):[#7;a:13]:[c:14]>>[F;D1;H0:5]-[C:4](-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:9]-[c:10](:[#7;a:11]:[c:12]):[#7;a:13]:[c:14])=[C:6](-[F;D1;H0:7])-[F;D1;H0:8] | 10.7 | [{"value": 10.0, "product": "FC(CC(=O)NC1=NC(=CC(=N1)OC)OC)=C(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 10.7, "product": "FC(CC(=O)NC1=NC(=CC(=N1)OC)OC)=C(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To an ice-cooled stirred suspension of 2-amino-4,6-dimethoxypyrimidine (1.55 g, 10 mmol) in dichloromethane (50 mL) and potassium carbonate (2.76 g, 20 mmol) in water (20 mL) was added 3,4,4-trifluoro-3-butenoyl chloride (3.17 g, 20 mmol). The reaction mixture was stirred in cold for 10 min and at r.t. for 15 min. The ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1cncnc1 | HCl | ClCCl.O | null | 0.25 | COc1cc(OC)nc(N)n1.O=C(Cl)CC(F)=C(F)F>ClCCl.O>COc1cc(OC)nc(NC(=O)CC(F)=C(F)F)n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e1a0dc1a113c454bac338b6a5d18d9a1 | NS(=O)(=O)C(F)(F)F.O=C(Cl)CC(F)=C(F)F>>O=C(CC(F)=C(F)F)NS(=O)(=O)C(F)(F)F | FC(S(=O)(=O)N)(F)F.FC(CC(=O)Cl)=C(F)F>>FC(CC(=O)NS(=O)(=O)C(F)(F)F)=C(F)F | [NH2:9][S:10](=[O:11])(=[O:12])[C:13]([F:14])([F:15])[F:16].Cl[C:2](=[O:1])[CH2:3][C:4]([F:5])=[C:6]([F:7])[F:8]>>[O:1]=[C:2]([CH2:3][C:4]([F:5])=[C:6]([F:7])[F:8])[NH:9][S:10](=[O:11])(=[O:12])[C:13]([F:14])([F:15])[F:16] | NS(=O)(=O)C(F)(F)F.O=C(Cl)CC(F)=C(F)F | O=C(CC(F)=C(F)F)NS(=O)(=O)C(F)(F)F | null | null | [OH-].[Na+] | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 403eb34e708e50f7077a9da490b1654c837258ce901614ddd1204eb6f2a10a27 | 37dfa12f19cd8cec29206fb8a18b7504935d92bc326a2084e9ef8a13076d3b87 | null | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4](-[F;D1;H0:5])=[C:6](-[F;D1;H0:7])-[F;D1;H0:8].[F;D1;H0:9]-[C:10](-[F;D1;H0:11])(-[F;D1;H0:12])-[#16:13](-[NH2;D1;+0:14])(=[O;D1;H0:15])=[O;D1;H0:16]>>[F;D1;H0:9]-[C:10](-[F;D1;H0:11])(-[F;D1;H0:12])-[#16:13](=[O;D1;H0:15])(=[O;D1;H0:16])-[NH;D2;+0:14]-[C;H0;D3;+0:1](=[O;D1;H0... | 16.4 | [{"value": 16.0, "product": "FC(CC(=O)NS(=O)(=O)C(F)(F)F)=C(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 16.4, "product": "FC(CC(=O)NS(=O)(=O)C(F)(F)F)=C(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | MINUTE | To an ice-cooled solution of trifluoromethanesulfonamide (2.75 g, 18.4 mmol) in 7.4 mL of 2.5 N sodium hydroxide was added 3,4,4-trifluoro-3-butenoyl chloride (2.93 g, 18.5 mmol) with stirring in 2 min. The mixture was stirred in cold for 30 min and the white precipitate formed was filtered, washed with cold water (10 ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Sulfonamide | Sulfonamide.Secondary amide | null | null | null | HCl | [OH-].[Na+] | null | 0.033333 | NS(=O)(=O)C(F)(F)F.O=C(Cl)CC(F)=C(F)F>[OH-].[Na+]>O=C(CC(F)=C(F)F)NS(=O)(=O)C(F)(F)F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0c18d3271e484f0f9ae2b826de5610c7 | O=C(Cl)CC(F)=C(F)F.c1nc[nH]n1>>O=C(CC(F)=C(F)F)n1cncn1 | N1N=CN=C1.FC(CC(=O)Cl)=C(F)F>>FC(CC(=O)N1N=CN=C1)=C(F)F | Cl[C:2](=[O:1])[CH2:3][C:4]([F:5])=[C:6]([F:7])[F:8].[nH:9]1[cH:10][n:11][cH:12][n:13]1>>[O:1]=[C:2]([CH2:3][C:4]([F:5])=[C:6]([F:7])[F:8])[n:9]1[cH:10][n:11][cH:12][n:13]1 | O=C(Cl)CC(F)=C(F)F.c1nc[nH]n1 | O=C(CC(F)=C(F)F)n1cncn1 | null | null | C(C)(=O)OCC | Acylation | N-alkylation of secondary amines with alkyl halides | 557f49a0cb1d0d512ac493f0ee8ad945d38bf5bdf5010b9c70be422959af43e1 | edbcca52d877d662e04f0d6de1a7107a8eca1d366ee6da0d92e37eb02a291876 | c1nc[nH]n1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4](-[F;D1;H0:5])=[C:6](-[F;D1;H0:7])-[F;D1;H0:8].[#7;a:9]1:[c:10]:[nH;D2;+0:11]:[#7;a:12]:[c:13]:1>>[F;D1;H0:5]-[C:4](-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[n;H0;D3;+0:11]1:[#7;a:12]:[c:13]:[#7;a:9]:[c:10]:1)=[C:6](-[F;D1;H0:7])-[F;D1;H0:8] | 94.2 | [{"value": 94.0, "product": "FC(CC(=O)N1N=CN=C1)=C(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.2, "product": "FC(CC(=O)N1N=CN=C1)=C(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1,2,4-triazole (1.38 g, 20 mmol) in ethyl acetate (100 mL) was added 3,4,4-trifluoro-3-butenoyl chloride (1.59 g, 10 mmol) at r.t. with stirring. The mixture was stirred for 30 min and filtered. The residue obtained after evaporation of the solvent was redissolved in dichloromethane (25 mL) and filtere... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | null | c1nc[nH]n1 | c1nc[nH]n1 | c1nc[nH]n1 | HCl | C(C)(=O)OCC | null | null | O=C(Cl)CC(F)=C(F)F.c1nc[nH]n1>C(C)(=O)OCC>O=C(CC(F)=C(F)F)n1cncn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-69bdc7c6a2fb4d4987a431b8e37f7f33 | CCOP(OCC)OCC.FC(F)=C(F)CBr>>C=C(F)C(F)(F)P(=O)(OCC)OCC.CCOP(=O)(CC(F)=C(F)F)OCC | FC(CBr)=C(F)F.P(OCC)(OCC)OCC>>FC(C(=C)F)(F)P(OCC)(OCC)=O.FC(CP(OCC)(OCC)=O)=C(F)F | [CH3:1][CH2:13][O:19][P:7]([O:8][CH2:27][CH3:28])[O:9][CH2:10][CH3:11].Br[CH2:20][C:21]([F:22])=[C:23]([F:3])[F:5]>>[CH2:1]=[C:2]([F:3])[C:4]([F:5])([F:6])[P:7](=[O:8])([O:9][CH2:10][CH3:11])[O:12][CH2:13][CH3:14].[CH3:15][CH2:16][O:17][P:18](=[O:19])([CH2:20][C:21]([F:22])=[C:23]([F:24])[F:25])[O:26][CH2:27][CH3:28] | CCOP(OCC)OCC.FC(F)=C(F)CBr | C=C(F)C(F)(F)P(=O)(OCC)OCC.CCOP(=O)(CC(F)=C(F)F)OCC | null | null | null | C-C Coupling | OtherReaction | 6aafb397980f97582b956ed97f243a519e5542b4a8982118820fd1654242656b | f2b204701ed3ec7dc2dd08dc61c8b4e3005170c87a035695d4236713be16d341 | null | Br-[CH2;D2;+0:1]-[C:2](-[F;D1;H0:3])=[C;H0;D3;+0:4](-[F;H0;D1;+0:5])-[F;H0;D1;+0:6].[C:7]-[#8:8]-[P;H0;D3;+0:9](-[O;H0;D2;+0:10]-[CH2;D2;+0:11]-[CH3;D1;+0:12])-[O;H0;D2;+0:13]-[CH2;D2;+0:14]-[C;D1;H3:15]>>[#8:16]-[#15:17](=[O;H0;D1;+0:10])(-[#8:18]-[CH2;D2;+0:14]-[C;D1;H3:15])-[CH2;D2;+0:1]-[C:2](-[F;D1;H0:3])=[C;H0;D3... | 14 | [{"value": 11.0, "product": "FC(C(=C)F)(F)P(OCC)(OCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 14.0, "product": "FC(CP(OCC)(OCC)=O)=C(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2,3,3-trifluoro-2-propenyl bromide (5.25 g, 30 mmol) and triethyl phosphite (4.15 g, 25 mmol) in acetonltrile (15 mL) was heated at reflux for overnight. The residue obtained after evaporation of the solvent was chromatographed over silica gel (hexanes/ethyl acetate/ethanol, 80/20/1) to give diethyl (1,1,... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Alkenyl halide.Alkenyl halide | Tertiary halide.Tertiary halide.Alkenyl halide.Alkenyl halide.Alkenyl halide.Vinyl | null | null | null | Br- | null | null | null | CCOP(OCC)OCC.FC(F)=C(F)CBr>>C=C(F)C(F)(F)P(=O)(OCC)OCC.CCOP(=O)(CC(F)=C(F)F)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b82f52deb4634a4bba0b118b41c64e02 | CC(C)(C)OP(=O)(CC(F)=C(F)F)OC(C)(C)C>>O=P(O)(O)CC(F)=C(F)F | FC(CP(OC(C)(C)C)(OC(C)(C)C)=O)=C(F)F.Cl>>FC(CP(O)(O)=O)=C(F)F | CC(C)(C)[O:3][P:2](=[O:1])([O:4]C(C)(C)C)[CH2:5][C:6]([F:7])=[C:8]([F:9])[F:10]>>[O:1]=[P:2]([OH:3])([OH:4])[CH2:5][C:6]([F:7])=[C:8]([F:9])[F:10] | CC(C)(C)OP(=O)(CC(F)=C(F)F)OC(C)(C)C | O=P(O)(O)CC(F)=C(F)F | null | null | CO | Deprotection | OtherReaction | eaaf8436ac19e7e26db9ff78e61eed5caf13b9167196c3230a9e1eb66b295f8b | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | null | C-C(-C)(-C)-[O;H0;D2;+0:1]-[#15:2](=[O;D1;H0:3])(-[C:4]-[C:5]=[C:6])-[O;H0;D2;+0:7]-C(-C)(-C)-C>>[C:6]=[C:5]-[C:4]-[#15:2](=[O;D1;H0:3])(-[OH;D1;+0:1])-[OH;D1;+0:7] | 45.8 | [{"value": 45.8, "product": "FC(CP(O)(O)=O)=C(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | The above di-t-butylphosphonate (0.5 g) was dissolved in 3 mL of methanol and treated with 0.5 mL, of 3N HCl and allowed to stand at r.t. for 30 min. The solution was concentrated and the residue was redissolved in 10 mL of water and washed with 10 mL of ether. Evaporation of the aqueous layer gave 0.14 g of 2,3,3-trif... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | Other | CO | null | 0.5 | CC(C)(C)OP(=O)(CC(F)=C(F)F)OC(C)(C)C>CO>O=P(O)(O)CC(F)=C(F)F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-33d9f641c6034e9a99040843b1b7b174 | C1=C(c2ccc(Oc3ccccc3)cc2)CCNC1>>c1ccc(Oc2ccc(C3CCNCC3)cc2)cc1 | CO.O(C1=CC=CC=C1)C1=CC=C(C=C1)C=1CCNCC1>>O(C1=CC=CC=C1)C1=CC=C(C=C1)C1CCNCC1 | [cH:1]1[cH:2][cH:3][c:4]([O:5][c:6]2[cH:7][cH:8][c:9]([C:10]3=[CH:11][CH2:12][NH:13][CH2:14][CH2:15]3)[cH:16][cH:17]2)[cH:18][cH:19]1>>[cH:1]1[cH:2][cH:3][c:4]([O:5][c:6]2[cH:7][cH:8][c:9]([CH:10]3[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]3)[cH:16][cH:17]2)[cH:18][cH:19]1 | C1=C(c2ccc(Oc3ccccc3)cc2)CCNC1 | c1ccc(Oc2ccc(C3CCNCC3)cc2)cc1 | null | [C].[Pd] | C(C)(=O)O | Reduction | Hydrogenation (double to single) | a3935c5f890a0f9fd8b2df279c7f0cf4325c4c1692c17d6ccce22e96da1fa3c7 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccc(Oc2ccc(C3CCNCC3)cc2)cc1 | [c:1]:[c:2](-[C;H0;D3;+0:3]1=[CH;D2;+0:4]-[C:5]-[#7:6]-[C:7]-[C:8]-1):[c:9]>>[c:1]:[c:2](-[CH;D3;+0:3]1-[C:8]-[C:7]-[#7:6]-[C:5]-[CH2;D2;+0:4]-1):[c:9] | 66 | [{"value": 66.0, "product": "O(C1=CC=CC=C1)C1=CC=C(C=C1)C1CCNCC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a 100 ml methanol solution of 3.51 g of the compound (3) synthesized in Reference Example 3 were added 200 mg of palladium carbon and 1 ml of acetic acid for hydrogenation at atmospheric pressure and room temperature. After the end of the reaction, the insolubles were filtered off and the filtrate was concentrated u... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1=CCNCC1 | C1CCNCC1 | c1ccccc1.c1ccccc1.C1CCNCC1 | null | [C].[Pd].C(C)(=O)O | null | null | C1=C(c2ccc(Oc3ccccc3)cc2)CCNC1>[C].[Pd].C(C)(=O)O>c1ccc(Oc2ccc(C3CCNCC3)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bf89635c7d584db89b9fd587daa3d2c0 | ClCCNCCCl.Nc1ccc(Cc2ccc(F)cc2)cc1>>Fc1ccc(Cc2ccc(N3CCNCC3)cc2)cc1 | FC1=CC=C(C=C1)CC1=CC=C(N)C=C1.Cl.ClCCNCCCl>>FC1=CC=C(C=C1)CC1=CC=C(C=C1)N1CCNCC1 | Cl[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]Cl.[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][c:7]2[cH:8][cH:9][c:10]([NH2:11])[cH:17][cH:18]2)[cH:19][cH:20]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][c:7]2[cH:8][cH:9][c:10]([N:11]3[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]3)[cH:17][cH:18]2)[cH:19][cH:20]1 | ClCCNCCCl.Nc1ccc(Cc2ccc(F)cc2)cc1 | Fc1ccc(Cc2ccc(N3CCNCC3)cc2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | dec7615731d236f383a5e0021b2ac4287f587bb876f98147d27e03daac7cbefb | 631870b1ab33be0edc94bc9ae10321f1c5ede4dd4db77035c9d3979e4a2118fb | c1ccc(Cc2ccc(N3CCNCC3)cc2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3]-[C:4]-[CH2;D2;+0:5]-Cl.[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[N;H0;D3;+0:6]1-[CH2;D2;+0:1]-[C:2]-[#7:3]-[C:4]-[CH2;D2;+0:5]-1):[c:9] | 75 | [{"value": 75.0, "product": "FC1=CC=C(C=C1)CC1=CC=C(C=C1)N1CCNCC1", "details": "PERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 2 | HOUR | A mixture of 500 mg of 4-(4-fluorophenyl) methylaniline and 445 mg of bis(2-chloroethyl)amine hydrochloride was stirred at 100° C. for 2 hours, then gradually raised in temperature to 200° C. and then further stirred for 2 hours. This was then cooled to room temperature, then the product was purified by silica gel colu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Primary amine | Tertiary amine | null | C1C[NH]CCN1 | c1ccccc1.c1ccccc1.C1C[NH]CCN1 | HCl | null | 100 | 2 | ClCCNCCCl.Nc1ccc(Cc2ccc(F)cc2)cc1>>Fc1ccc(Cc2ccc(N3CCNCC3)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a457ce1a504046278989f2096f1b01fc | NC1CCCOc2ccccc21.O=C(Br)CBr>>O=C(CBr)NC1CCCOc2ccccc21 | C(Cl)Cl.NC1CCCOC2=C1C=CC=C2.[Cl-].[NH4+].BrCC(=O)Br>>BrCC(=O)NC1CCCOC2=C1C=CC=C2 | [NH2:5][CH:6]1[CH2:7][CH2:8][CH2:9][O:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]21.Br[C:2](=[O:1])[CH2:3][Br:4]>>[O:1]=[C:2]([CH2:3][Br:4])[NH:5][CH:6]1[CH2:7][CH2:8][CH2:9][O:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]21 | NC1CCCOc2ccccc21.O=C(Br)CBr | O=C(CBr)NC1CCCOc2ccccc21 | null | null | C(C)N(CC)CC | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc2c(c1)CCCCO2 | Br-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Br;D1;H0:4].[C:5]-[C:6](-[NH2;D1;+0:7])-[c:8]>>[Br;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6](-[C:5])-[c:8] | 65 | [{"value": 65.0, "product": "BrCC(=O)NC1CCCOC2=C1C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a 5 ml methylene chloride solution of 150 mg of 5-amino-2,3,4,5-tetrahydro-1-benzoxepine (Japanese Unexamined Patent Publication (Kokai) No. 4-178381) and 0.15 ml of triethylamine was added dropwise, under ice cooling, 0.08 ml of bromoacetyl bromide. This was then stirred at room temperature for 1 hour. To the react... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2c(c1)CCCCO2 | HBr | C(C)N(CC)CC | null | 1 | NC1CCCOc2ccccc21.O=C(Br)CBr>C(C)N(CC)CC>O=C(CBr)NC1CCCOc2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b9bc34feae494fc2941a6a9edafd74d8 | NC1CCCOc2ccccc21.O=C(Cl)CCCCl>>O=C(CCCCl)NC1CCCOc2ccccc21 | NC1CCCOC2=C1C=CC=C2.ClCCCC(=O)Cl>>ClCCCC(=O)NC1CCCOC2=C1C=CC=C2 | [NH2:7][CH:8]1[CH2:9][CH2:10][CH2:11][O:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]21.Cl[C:2](=[O:1])[CH2:3][CH2:4][CH2:5][Cl:6]>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][Cl:6])[NH:7][CH:8]1[CH2:9][CH2:10][CH2:11][O:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]21 | NC1CCCOc2ccccc21.O=C(Cl)CCCCl | O=C(CCCCl)NC1CCCOc2ccccc21 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc2c(c1)CCCCO2 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6](-[NH2;D1;+0:7])-[c:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6](-[C:5])-[c:8] | null | [] | null | null | null | null | 5-amino-2,3,4,5-tetrahydro-1-benzoxepine and 4-chlorobutyryl choride were used to produce the above compound in the same way as Reference Example 8.
Conditions: See reaction.notes.procedure_details.
Workup: to produce the above compound in the same way as Reference Example 8 | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2c(c1)CCCCO2 | HCl | null | null | null | NC1CCCOc2ccccc21.O=C(Cl)CCCCl>>O=C(CCCCl)NC1CCCOc2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1b902b18e00d40be87de78d200ab46e6 | Nc1ccccc1Cc1ccccc1.O=C(Cl)CCCBr>>O=C(CCCBr)Nc1ccccc1Cc1ccccc1 | C(C1=CC=CC=C1)C1=C(N)C=CC=C1.BrCCCC(=O)Cl>>C(C1=CC=CC=C1)C1=C(C=CC=C1)NC(CCCBr)=O | [NH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1.Cl[C:2](=[O:1])[CH2:3][CH2:4][CH2:5][Br:6]>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][Br:6])[NH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | Nc1ccccc1Cc1ccccc1.O=C(Cl)CCCBr | O=C(CCCBr)Nc1ccccc1Cc1ccccc1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc(Cc2ccccc2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | null | null | 2-benzylaniline and 4-bromobutyryl chloride were used to produce the above compound in the same way as Reference Example 8.
Conditions: See reaction.notes.procedure_details.
Workup: to produce the above compound in the same way as Reference Example 8 | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HCl | null | null | null | Nc1ccccc1Cc1ccccc1.O=C(Cl)CCCBr>>O=C(CCCBr)Nc1ccccc1Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9a106ac872e44c028f407e5e2548e831 | Nc1ccccc1Cc1ccccc1.O=C(Cl)CCCCCBr>>O=C(CCCCCBr)Nc1ccccc1Cc1ccccc1 | C(C1=CC=CC=C1)C1=C(N)C=CC=C1.BrCCCCCC(=O)Cl>>C(C1=CC=CC=C1)C1=C(C=CC=C1)NC(CCCCCBr)=O | [NH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.Cl[C:2](=[O:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][Br:8]>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][Br:8])[NH:9][c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | Nc1ccccc1Cc1ccccc1.O=C(Cl)CCCCCBr | O=C(CCCCCBr)Nc1ccccc1Cc1ccccc1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc(Cc2ccccc2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | null | null | 2-benzylaniline and 6-bromohexanoyl chloride were used to produce the above compound in the same way as Reference Example 8.
Conditions: See reaction.notes.procedure_details.
Workup: to produce the above compound in the same way as Reference Example 8 | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HCl | null | null | null | Nc1ccccc1Cc1ccccc1.O=C(Cl)CCCCCBr>>O=C(CCCCCBr)Nc1ccccc1Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d2f33c1431d042dc8d4c42d33385b25c | Cc1cccc(Cc2ccccc2)c1N.O=C(Br)CBr>>Cc1cccc(Cc2ccccc2)c1NC(=O)CBr | C(C1=CC=CC=C1)C1=C(N)C(=CC=C1)C.BrCC(=O)Br>>C(C1=CC=CC=C1)C1=C(C(=CC=C1)C)NC(CBr)=O | [CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[c:14]1[NH2:15].Br[C:16](=[O:17])[CH2:18][Br:19]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[c:14]1[NH:15][C:16](=[O:17])[CH2:18][Br:19] | Cc1cccc(Cc2ccccc2)c1N.O=C(Br)CBr | Cc1cccc(Cc2ccccc2)c1NC(=O)CBr | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc(Cc2ccccc2)cc1 | Br-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Br;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[Br;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | null | null | 2-benzyl-6-methylaniline [A. W. H. Wardrop et al.: J. Chem. Soc., Perkin Trans. 1, 12, 1279 (1976)] and bromoacetyl bromide were used to produce the above compound in the same way as Reference Example 8.
Conditions: See reaction.notes.procedure_details.
Workup: to produce the above compound in the same way as Reference... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HBr | null | null | null | Cc1cccc(Cc2ccccc2)c1N.O=C(Br)CBr>>Cc1cccc(Cc2ccccc2)c1NC(=O)CBr |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-52a0973dcc1647d6b5bf02c79809d649 | Cc1cccc(Cc2ccccc2)c1N.O=C(Cl)CCCCl>>Cc1cccc(Cc2ccccc2)c1NC(=O)CCCCl | C(C1=CC=CC=C1)C1=C(N)C(=CC=C1)C.ClCCCC(=O)Cl>>C(C1=CC=CC=C1)C1=C(C(=CC=C1)C)NC(CCCCl)=O | [CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[c:14]1[NH2:15].Cl[C:16](=[O:17])[CH2:18][CH2:19][CH2:20][Cl:21]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[c:14]1[NH:15][C:16](=[O:17])[CH2:18][CH2:19][CH2:20][Cl:21] | Cc1cccc(Cc2ccccc2)c1N.O=C(Cl)CCCCl | Cc1cccc(Cc2ccccc2)c1NC(=O)CCCCl | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc(Cc2ccccc2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | null | null | 2-benzyl-6-methylaniline and 4-chlorobutyryl choride were used to produce the above compound in the same way as Reference Example 8.
Conditions: See reaction.notes.procedure_details.
Workup: to produce the above compound in the same way as Reference Example 8 | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HCl | null | null | null | Cc1cccc(Cc2ccccc2)c1N.O=C(Cl)CCCCl>>Cc1cccc(Cc2ccccc2)c1NC(=O)CCCCl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-63a70aa1c69f4c69985323de9986a8eb | O=C(Br)CBr.c1ccc2c(c1)NCCCO2>>O=C(CBr)N1CCCOc2ccccc21 | O1CCCNC2=C1C=CC=C2.BrCC(=O)Br>>BrCC(=O)N1CCCOC2=C1C=CC=C2 | Br[C:2](=[O:1])[CH2:3][Br:4].[NH:5]1[CH2:6][CH2:7][CH2:8][O:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]21>>[O:1]=[C:2]([CH2:3][Br:4])[N:5]1[CH2:6][CH2:7][CH2:8][O:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]21 | O=C(Br)CBr.c1ccc2c(c1)NCCCO2 | O=C(CBr)N1CCCOc2ccccc21 | null | null | null | Acylation | N-alkylation of secondary amines with alkyl halides | 6710df8ef2400eb77157860fd087bd0b06f310ded4e6497344dde101b9c5d078 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | c1ccc2c(c1)NCCCO2 | Br-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Br;D1;H0:4].[#8:5]-[c:6]:[c:7](:[c:8])-[NH;D2;+0:9]-[C:10]-[C:11]>>[#8:5]-[c:6]:[c:7](:[c:8])-[N;H0;D3;+0:9](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Br;D1;H0:4])-[C:10]-[C:11] | null | [] | null | null | null | null | 2,3,4,5-tetrahydro-1,5-benzoxazepine [E. K. Orlova et al.; Kim. Geterotsikl. Soedin.,9, 1296 (1975): Chem. abstra., 84, 59411] and bromoacetyl bromide were used to produce the above compound in the same way as Reference Example 8.
Conditions: See reaction.notes.procedure_details.
Workup: to produce the above compound i... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)NCCCO2 | c1ccc2c(c1)[NH]CCCO2 | c1ccc2c(c1)[NH]CCCO2 | HBr | null | null | null | O=C(Br)CBr.c1ccc2c(c1)NCCCO2>>O=C(CBr)N1CCCOc2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-04e4aa0d550f42b3965842045af58c87 | O=C(Cl)CCCCl.c1ccc2c(c1)NCCCO2>>O=C(CCCCl)N1CCCOc2ccccc21 | O1CCCNC2=C1C=CC=C2.ClCCCC(=O)Cl>>ClCCCC(=O)N1CCCOC2=C1C=CC=C2 | Cl[C:2](=[O:1])[CH2:3][CH2:4][CH2:5][Cl:6].[NH:7]1[CH2:8][CH2:9][CH2:10][O:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]21>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][Cl:6])[N:7]1[CH2:8][CH2:9][CH2:10][O:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]21 | O=C(Cl)CCCCl.c1ccc2c(c1)NCCCO2 | O=C(CCCCl)N1CCCOc2ccccc21 | null | null | null | Acylation | N-alkylation of secondary amines with alkyl halides | 6710df8ef2400eb77157860fd087bd0b06f310ded4e6497344dde101b9c5d078 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | c1ccc2c(c1)NCCCO2 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[#8:5]-[c:6]:[c:7](:[c:8])-[NH;D2;+0:9]-[C:10]-[C:11]>>[#8:5]-[c:6]:[c:7](:[c:8])-[N;H0;D3;+0:9](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4])-[C:10]-[C:11] | null | [] | null | null | null | null | 2,3,4,5-tetrahydro-1,5-benzoxazepine and 4-chlorobutyryl chloride were used to produce the above compound in the same way as Reference Example 8.
Conditions: See reaction.notes.procedure_details.
Workup: to produce the above compound in the same way as Reference Example 8 | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)NCCCO2 | c1ccc2c(c1)[NH]CCCO2 | c1ccc2c(c1)[NH]CCCO2 | HCl | null | null | null | O=C(Cl)CCCCl.c1ccc2c(c1)NCCCO2>>O=C(CCCCl)N1CCCOc2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-962a1ba5fe544c1c818dea60c177a4b0 | O=S(=O)(Cl)CCCCl.c1ccc2c(c1)NCCCO2>>O=S(=O)(CCCCl)N1CCCOc2ccccc21 | O1CCCNC2=C1C=CC=C2.ClCCCS(=O)(=O)Cl>>ClCCCS(=O)(=O)N1CCCOC2=C1C=CC=C2 | Cl[S:2](=[O:1])(=[O:3])[CH2:4][CH2:5][CH2:6][Cl:7].[NH:8]1[CH2:9][CH2:10][CH2:11][O:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]21>>[O:1]=[S:2](=[O:3])([CH2:4][CH2:5][CH2:6][Cl:7])[N:8]1[CH2:9][CH2:10][CH2:11][O:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]21 | O=S(=O)(Cl)CCCCl.c1ccc2c(c1)NCCCO2 | O=S(=O)(CCCCl)N1CCCOc2ccccc21 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | 19231af189d4d1804e111c8279b9aa211e91c0c19a9e2aea4b4e8d2f3188126d | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | c1ccc2c(c1)NCCCO2 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]-[C:5].[#8:6]-[c:7]:[c:8](:[c:9])-[NH;D2;+0:10]-[C:11]-[C:12]>>[#8:6]-[c:7]:[c:8](:[c:9])-[N;H0;D3;+0:10](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]-[C:5])-[C:11]-[C:12] | null | [] | null | null | null | null | 2,3,4,5-tetrahydro-1,5-benzoxazepine and 3-chloropropanesulfonyl chloride were used to produce the above compound in the same way as Reference Example 8.
Conditions: See reaction.notes.procedure_details.
Workup: to produce the above compound in the same way as Reference Example 8 | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | c1ccc2c(c1)NCCCO2 | c1ccc2c(c1)[NH]CCCO2 | c1ccc2c(c1)[NH]CCCO2 | HCl | null | null | null | O=S(=O)(Cl)CCCCl.c1ccc2c(c1)NCCCO2>>O=S(=O)(CCCCl)N1CCCOc2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-36741af99bf144f2b5dad69210fa2380 | Cc1cccc(C)c1N.O=C(Br)CBr>>Cc1cccc(C)c1NC(=O)CBr | CC1=C(N)C(=CC=C1)C.BrCC(=O)Br>>CC1=C(C(=CC=C1)C)NC(CBr)=O | [CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH3:7])[c:8]1[NH2:9].Br[C:10](=[O:11])[CH2:12][Br:13]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH3:7])[c:8]1[NH:9][C:10](=[O:11])[CH2:12][Br:13] | Cc1cccc(C)c1N.O=C(Br)CBr | Cc1cccc(C)c1NC(=O)CBr | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccccc1 | Br-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Br;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[Br;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | null | null | 2,6-dimethylaniline and bromoacetyl bromide were used to produce the above compound in the same way as Reference Example 8.
Conditions: See reaction.notes.procedure_details.
Workup: to produce the above compound in the same way as Reference Example 8 | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1 | HBr | null | null | null | Cc1cccc(C)c1N.O=C(Br)CBr>>Cc1cccc(C)c1NC(=O)CBr |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f784d3da6cac47f0b04d1bfda98f77f5 | Nc1ccccc1.O=C(Br)CBr>>O=C(CBr)Nc1ccccc1 | NC1=CC=CC=C1.BrCC(=O)Br>>C1(=CC=CC=C1)NC(CBr)=O | [NH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1.Br[C:2](=[O:1])[CH2:3][Br:4]>>[O:1]=[C:2]([CH2:3][Br:4])[NH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1 | Nc1ccccc1.O=C(Br)CBr | O=C(CBr)Nc1ccccc1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccccc1 | Br-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Br;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[Br;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | null | null | Aniline and bromoacetyl bromide were used to produce the above compound in the same way as Reference Example 8.
Conditions: See reaction.notes.procedure_details.
Workup: to produce the above compound in the same way as Reference Example 8 | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1 | HBr | null | null | null | Nc1ccccc1.O=C(Br)CBr>>O=C(CBr)Nc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9c78ca195b6645a08315152c3e1cca8d | CC(C)c1cccc(C(C)C)c1N.O=C(Br)CBr>>CC(C)c1cccc(C(C)C)c1NC(=O)CBr | C(C)(C)C1=C(N)C(=CC=C1)C(C)C.BrCC(=O)Br>>C(C)(C)C1=C(C(=CC=C1)C(C)C)NC(CBr)=O | [CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([CH:9]([CH3:10])[CH3:11])[c:12]1[NH2:13].Br[C:14](=[O:15])[CH2:16][Br:17]>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([CH:9]([CH3:10])[CH3:11])[c:12]1[NH:13][C:14](=[O:15])[CH2:16][Br:17] | CC(C)c1cccc(C(C)C)c1N.O=C(Br)CBr | CC(C)c1cccc(C(C)C)c1NC(=O)CBr | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccccc1 | Br-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Br;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[Br;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | null | null | 2,6-diisopropylaniline and bromoacetyl bromide were used to produce the above compound in the same way as Reference Example 8.
Conditions: See reaction.notes.procedure_details.
Workup: to produce the above compound in the same way as Reference Example 8 | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1 | HBr | null | null | null | CC(C)c1cccc(C(C)C)c1N.O=C(Br)CBr>>CC(C)c1cccc(C(C)C)c1NC(=O)CBr |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-026df28cd21a449188012634f40210b4 | C=C(NC)c1ccccc1.O=C(Br)CBr>>C=C(c1ccccc1)N(C)C(=O)CBr | CNC(=C)C1=CC=CC=C1.BrCC(=O)Br>>CN(C(CBr)=O)C(=C)C1=CC=CC=C1 | [CH2:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[NH:9][CH3:10].Br[C:11](=[O:12])[CH2:13][Br:14]>>[CH2:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[N:9]([CH3:10])[C:11](=[O:12])[CH2:13][Br:14] | C=C(NC)c1ccccc1.O=C(Br)CBr | C=C(c1ccccc1)N(C)C(=O)CBr | null | null | null | Acylation | N-alkylation of secondary amines with alkyl halides | f4ee143c87f2dc7ff41a31c4a38f85d3fc2914b4b3f247bc92610a9d8f7aed02 | 5b3374a88a43fdc5f21ba385f78d526894e7004ef039565462ba297b171c1700 | c1ccccc1 | Br-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Br;D1;H0:4].[C;D1;H2:5]=[C:6](-[c:7])-[NH;D2;+0:8]-[C;D1;H3:9]>>[Br;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:8](-[C;D1;H3:9])-[C:6](=[C;D1;H2:5])-[c:7] | null | [] | null | null | null | null | N-methyl-N-(1-phenylvinyl)amine and bromoacetyl bromide were used to produce the above compound in the same way as Reference Example 8.
Conditions: See reaction.notes.procedure_details.
Workup: to produce the above compound in the same way as Reference Example 8 | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Acyl halide | Enamine.Tertiary amide | null | null | c1ccccc1 | HBr | null | null | null | C=C(NC)c1ccccc1.O=C(Br)CBr>>C=C(c1ccccc1)N(C)C(=O)CBr |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-29bdac8cd38e44e3a6167a6148c0ca92 | N#CCCl.c1ccc(Oc2ccc(C3CCNCC3)cc2)cc1>>N#CCN1CCC(c2ccc(Oc3ccccc3)cc2)CC1 | O(C1=CC=CC=C1)C1=CC=C(C=C1)C1CCNCC1.ClCC#N.[I-].[Na+].C([O-])([O-])=O.[K+].[K+]>>C(#N)CN1CCC(CC1)C1=CC=C(C=C1)OC1=CC=CC=C1 | Cl[CH2:3][C:2]#[N:1].[NH:4]1[CH2:5][CH2:6][CH:7]([c:8]2[cH:9][cH:10][c:11]([O:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19][cH:20]2)[CH2:21][CH2:22]1>>[N:1]#[C:2][CH2:3][N:4]1[CH2:5][CH2:6][CH:7]([c:8]2[cH:9][cH:10][c:11]([O:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19][cH:20]2)[CH2:21][CH2:22]1 | N#CCCl.c1ccc(Oc2ccc(C3CCNCC3)cc2)cc1 | N#CCN1CCC(c2ccc(Oc3ccccc3)cc2)CC1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(Oc2ccc(C3CCNCC3)cc2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3])-[C:7]-[C:8] | 91 | [{"value": 91.0, "product": "C(#N)CN1CCC(CC1)C1=CC=C(C=C1)OC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To an 8 ml dimethylformamide solution of 300 mg of the compound (4) synthesized in Reference Example 4 were added 93 mg of chloroacetonitrile, 355 mg of sodium iodide, and 196 mg of potassium carbonate. This was then heated at reflux for 2 hours. To the reaction was added 10 ml of ice water, then extraction was perform... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HCl | CN(C=O)C | null | null | N#CCCl.c1ccc(Oc2ccc(C3CCNCC3)cc2)cc1>CN(C=O)C>N#CCN1CCC(c2ccc(Oc3ccccc3)cc2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-23b3904cefa54993927e4b9f165740eb | O=C(CBr)NC1CCCOc2ccccc21.c1ccc(Oc2ccc(C3CCNCC3)cc2)cc1>>O=C(CN1CCC(c2ccc(Oc3ccccc3)cc2)CC1)NC1CCCOc2ccccc21 | C(C)#N.BrCC(=O)NC1CCCOC2=C1C=CC=C2.O(C1=CC=CC=C1)C1=CC=C(C=C1)C1CCNCC1>>O(C1=CC=CC=C1)C1=CC=C(C=C1)C1CCN(CC1)CC(=O)NC1CCCOC2=C1C=CC=C2 | Br[CH2:3][C:2](=[O:1])[NH:23][CH:24]1[CH2:25][CH2:26][CH2:27][O:28][c:29]2[cH:30][cH:31][cH:32][cH:33][c:34]21.[NH:4]1[CH2:5][CH2:6][CH:7]([c:8]2[cH:9][cH:10][c:11]([O:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19][cH:20]2)[CH2:21][CH2:22]1>>[O:1]=[C:2]([CH2:3][N:4]1[CH2:5][CH2:6][CH:7]([c:8]2[cH:9][cH:10][c:11... | O=C(CBr)NC1CCCOc2ccccc21.c1ccc(Oc2ccc(C3CCNCC3)cc2)cc1 | O=C(CN1CCC(c2ccc(Oc3ccccc3)cc2)CC1)NC1CCCOc2ccccc21 | null | null | C(C)N(CC)CC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CN1CCC(c2ccc(Oc3ccccc3)cc2)CC1)NC1CCCOc2ccccc21 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[C:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[C:5])-[C:9]-[C:10] | 98 | [{"value": 98.0, "product": "O(C1=CC=CC=C1)C1=CC=C(C=C1)C1CCN(CC1)CC(=O)NC1CCCOC2=C1C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a 5 ml acetonitrile solution of 190 mg of the compound (8) synthesized in Reference Example 8 were added 184 mg of the compound (4) synthesized in Reference Example 4 and 0.14 ml of triethylamine. This was heated at reflux for 3 hours. To the reaction was added 10 ml of ice water, then extraction was performed with ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.c1ccccc1.c1ccc2c(c1)CCCCO2 | HBr | C(C)N(CC)CC | null | null | O=C(CBr)NC1CCCOc2ccccc21.c1ccc(Oc2ccc(C3CCNCC3)cc2)cc1>C(C)N(CC)CC>O=C(CN1CCC(c2ccc(Oc3ccccc3)cc2)CC1)NC1CCCOc2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ad97d3a2866d4a9fb98e1d97b465587f | C1=C(c2ccc(Oc3ccccc3)cc2)CCNC1.O=C(CCCCl)NC1CCCOc2ccccc21>>O=C(CCCN1CC=C(c2ccc(Oc3ccccc3)cc2)CC1)NC1CCCOc2ccccc21 | ClCCCC(=O)NC1CCCOC2=C1C=CC=C2.O(C1=CC=CC=C1)C1=CC=C(C=C1)C=1CCNCC1>>O(C1=CC=CC=C1)C1=CC=C(C=C1)C=1CCN(CC1)CCCC(=O)NC1CCCOC2=C1C=CC=C2 | [NH:6]1[CH2:7][CH:8]=[C:9]([c:10]2[cH:11][cH:12][c:13]([O:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[cH:21][cH:22]2)[CH2:23][CH2:24]1.Cl[CH2:5][CH2:4][CH2:3][C:2](=[O:1])[NH:25][CH:26]1[CH2:27][CH2:28][CH2:29][O:30][c:31]2[cH:32][cH:33][cH:34][cH:35][c:36]21>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH:8]=[C... | C1=C(c2ccc(Oc3ccccc3)cc2)CCNC1.O=C(CCCCl)NC1CCCOc2ccccc21 | O=C(CCCN1CC=C(c2ccc(Oc3ccccc3)cc2)CC1)NC1CCCOc2ccccc21 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 8654cc80599d789a53d1ba976beafc80caf5e8f4841be95ae420fabbb64ff19c | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CCCN1CC=C(c2ccc(Oc3ccccc3)cc2)CC1)NC1CCCOc2ccccc21 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4](-[#7:5])=[O;D1;H0:6].[c:7]-[C:8]1=[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[#7:5]-[C:4](=[O;D1;H0:6])-[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:11]1-[C:12]-[C:13]-[C:8](-[c:7])=[C:9]-[C:10]-1 | null | [] | null | null | null | null | The compound (9) synthesized in Reference Example 9 and the compound (3) synthesized in Reference Example 3 were used to produce the above compound in the same way as Example 1.
Conditions: See reaction.notes.procedure_details.
Workup: to produce the above compound in the same way as Example 1 | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1=CCNCC1 | C1=CC[NH]CC1 | C1=CC[NH]CC1.c1ccccc1.c1ccccc1.c1ccc2c(c1)CCCCO2 | HCl | null | null | null | C1=C(c2ccc(Oc3ccccc3)cc2)CCNC1.O=C(CCCCl)NC1CCCOc2ccccc21>>O=C(CCCN1CC=C(c2ccc(Oc3ccccc3)cc2)CC1)NC1CCCOc2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5a9645c8c72546f59db841e4d13fd844 | Fc1ccc(Cc2ccc(N3CCNCC3)cc2)cc1.O=S(=O)(NCCCCl)C1CCCOc2ccccc21>>O=S(=O)(NCCCN1CCN(c2ccc(Cc3ccc(F)cc3)cc2)CC1)C1CCCOc2ccccc21 | ClCCCNS(=O)(=O)C1CCCOC2=C1C=CC=C2.FC1=CC=C(C=C1)CC1=CC=C(C=C1)N1CCNCC1>>FC1=CC=C(C=C1)CC1=CC=C(C=C1)N1CCN(CC1)CCCNS(=O)(=O)C1CCCOC2=C1C=CC=C2 | [NH:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][cH:14][c:15]([CH2:16][c:17]3[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]3)[cH:24][cH:25]2)[CH2:26][CH2:27]1.Cl[CH2:7][CH2:6][CH2:5][NH:4][S:2](=[O:1])(=[O:3])[CH:28]1[CH2:29][CH2:30][CH2:31][O:32][c:33]2[cH:34][cH:35][cH:36][cH:37][c:38]21>>[O:1]=[S:2](=[O:3])([NH:4][CH2:5][CH2... | Fc1ccc(Cc2ccc(N3CCNCC3)cc2)cc1.O=S(=O)(NCCCCl)C1CCCOc2ccccc21 | O=S(=O)(NCCCN1CCN(c2ccc(Cc3ccc(F)cc3)cc2)CC1)C1CCCOc2ccccc21 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=S(=O)(NCCCN1CCN(c2ccc(Cc3ccccc3)cc2)CC1)C1CCCOc2ccccc21 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:8]-[C:9]-[#7:4]-[C:5]-[C:6]-1 | null | [] | null | null | null | null | The compound (10) synthesized in Reference Example 10 and the compound (5) synthesized in Reference Example 5 were used to produce the above compound in the same way as Example 1.
Conditions: See reaction.notes.procedure_details.
Workup: to produce the above compound in the same way as Example 1 | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1.c1ccc2c(c1)CCCCO2 | HCl | null | null | null | Fc1ccc(Cc2ccc(N3CCNCC3)cc2)cc1.O=S(=O)(NCCCCl)C1CCCOc2ccccc21>>O=S(=O)(NCCCN1CCN(c2ccc(Cc3ccc(F)cc3)cc2)CC1)C1CCCOc2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1b11ab13f0684648bf9745c477ecdcad | C1=C(c2ccc(Oc3ccccc3)cc2)CCNC1.O=C(CCCBr)Nc1ccccc1Cc1ccccc1>>O=C(CCCN1CC=C(c2ccc(Oc3ccccc3)cc2)CC1)Nc1ccccc1Cc1ccccc1 | C(C1=CC=CC=C1)C1=C(C=CC=C1)NC(CCCBr)=O.O(C1=CC=CC=C1)C1=CC=C(C=C1)C=1CCNCC1>>C(C1=CC=CC=C1)C1=C(C=CC=C1)NC(CCCN1CCC(=CC1)C1=CC=C(C=C1)OC1=CC=CC=C1)=O | [NH:6]1[CH2:7][CH:8]=[C:9]([c:10]2[cH:11][cH:12][c:13]([O:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[cH:21][cH:22]2)[CH2:23][CH2:24]1.Br[CH2:5][CH2:4][CH2:3][C:2](=[O:1])[NH:25][c:26]1[cH:27][cH:28][cH:29][cH:30][c:31]1[CH2:32][c:33]1[cH:34][cH:35][cH:36][cH:37][cH:38]1>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH2... | C1=C(c2ccc(Oc3ccccc3)cc2)CCNC1.O=C(CCCBr)Nc1ccccc1Cc1ccccc1 | O=C(CCCN1CC=C(c2ccc(Oc3ccccc3)cc2)CC1)Nc1ccccc1Cc1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 8654cc80599d789a53d1ba976beafc80caf5e8f4841be95ae420fabbb64ff19c | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CCCN1CC=C(c2ccc(Oc3ccccc3)cc2)CC1)Nc1ccccc1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4](-[#7:5])=[O;D1;H0:6].[c:7]-[C:8]1=[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[#7:5]-[C:4](=[O;D1;H0:6])-[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:11]1-[C:12]-[C:13]-[C:8](-[c:7])=[C:9]-[C:10]-1 | null | [] | null | null | null | null | The compound (11) synthesized in Reference Example 11 and the compound (3) synthesized in Reference Example 3 were used to produce the above compound in the same way as Example 1.
Conditions: See reaction.notes.procedure_details.
Workup: to produce the above compound in the same way as Example 1 | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1=CCNCC1 | C1=CC[NH]CC1 | C1=CC[NH]CC1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HBr | null | null | null | C1=C(c2ccc(Oc3ccccc3)cc2)CCNC1.O=C(CCCBr)Nc1ccccc1Cc1ccccc1>>O=C(CCCN1CC=C(c2ccc(Oc3ccccc3)cc2)CC1)Nc1ccccc1Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e1e8c0f8715845c883b3981c2fc0fb5d | O=C(CCCBr)Nc1ccccc1Cc1ccccc1.c1ccc(Oc2ccc(C3CCNCC3)cc2)cc1>>O=C(CCCN1CCC(c2ccc(Oc3ccccc3)cc2)CC1)Nc1ccccc1Cc1ccccc1 | C(C1=CC=CC=C1)C1=C(C=CC=C1)NC(CCCBr)=O.O(C1=CC=CC=C1)C1=CC=C(C=C1)C1CCNCC1>>C(C1=CC=CC=C1)C1=C(C=CC=C1)NC(CCCN1CCC(CC1)C1=CC=C(C=C1)OC1=CC=CC=C1)=O | Br[CH2:5][CH2:4][CH2:3][C:2](=[O:1])[NH:25][c:26]1[cH:27][cH:28][cH:29][cH:30][c:31]1[CH2:32][c:33]1[cH:34][cH:35][cH:36][cH:37][cH:38]1.[NH:6]1[CH2:7][CH2:8][CH:9]([c:10]2[cH:11][cH:12][c:13]([O:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[cH:21][cH:22]2)[CH2:23][CH2:24]1>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH... | O=C(CCCBr)Nc1ccccc1Cc1ccccc1.c1ccc(Oc2ccc(C3CCNCC3)cc2)cc1 | O=C(CCCN1CCC(c2ccc(Oc3ccccc3)cc2)CC1)Nc1ccccc1Cc1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CCCN1CCC(c2ccc(Oc3ccccc3)cc2)CC1)Nc1ccccc1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4](-[#7:5])=[O;D1;H0:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[#7:5]-[C:4](=[O;D1;H0:6])-[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:9](-[C:8]-[C:7])-[C:10]-[C:11] | null | [] | null | null | null | null | The compound (11) synthesized in Reference Example 11 and the compound (4) synthesized in Reference Example 4 were used to produce the above compound in the same way as Example 1.
Conditions: See reaction.notes.procedure_details.
Workup: to produce the above compound in the same way as Example 1 | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HBr | null | null | null | O=C(CCCBr)Nc1ccccc1Cc1ccccc1.c1ccc(Oc2ccc(C3CCNCC3)cc2)cc1>>O=C(CCCN1CCC(c2ccc(Oc3ccccc3)cc2)CC1)Nc1ccccc1Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e15f7a1400b44ac09662d913188c8d02 | Fc1ccc(Cc2ccc(N3CCNCC3)cc2)cc1.O=C(CCCBr)Nc1ccccc1Cc1ccccc1>>O=C(CCCN1CCN(c2ccc(Cc3ccc(F)cc3)cc2)CC1)Nc1ccccc1Cc1ccccc1 | C(C1=CC=CC=C1)C1=C(C=CC=C1)NC(CCCBr)=O.FC1=CC=C(C=C1)CC1=CC=C(C=C1)N1CCNCC1>>C(C1=CC=CC=C1)C1=C(C=CC=C1)NC(CCCN1CCN(CC1)C1=CC=C(C=C1)CC1=CC=C(C=C1)F)=O | [NH:6]1[CH2:7][CH2:8][N:9]([c:10]2[cH:11][cH:12][c:13]([CH2:14][c:15]3[cH:16][cH:17][c:18]([F:19])[cH:20][cH:21]3)[cH:22][cH:23]2)[CH2:24][CH2:25]1.Br[CH2:5][CH2:4][CH2:3][C:2](=[O:1])[NH:26][c:27]1[cH:28][cH:29][cH:30][cH:31][c:32]1[CH2:33][c:34]1[cH:35][cH:36][cH:37][cH:38][cH:39]1>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][... | Fc1ccc(Cc2ccc(N3CCNCC3)cc2)cc1.O=C(CCCBr)Nc1ccccc1Cc1ccccc1 | O=C(CCCN1CCN(c2ccc(Cc3ccc(F)cc3)cc2)CC1)Nc1ccccc1Cc1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CCCN1CCN(c2ccc(Cc3ccccc3)cc2)CC1)Nc1ccccc1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4](-[#7:5])=[O;D1;H0:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[#7:5]-[C:4](=[O;D1;H0:6])-[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1 | null | [] | null | null | null | null | The compound (11) synthesized in Reference Example 11 and the compound (5) synthesized in Reference Example 5 were used to produce the above compound in the same way as Example 1.
Conditions: See reaction.notes.procedure_details.
Workup: to produce the above compound in the same way as Example 1 | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HBr | null | null | null | Fc1ccc(Cc2ccc(N3CCNCC3)cc2)cc1.O=C(CCCBr)Nc1ccccc1Cc1ccccc1>>O=C(CCCN1CCN(c2ccc(Cc3ccc(F)cc3)cc2)CC1)Nc1ccccc1Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-71e7f2ae1b1b4d3b94456563cef0ba78 | Fc1ccc(Cc2ccc(C3CCNCC3)cc2)cc1.O=C(CCCBr)Nc1ccccc1Cc1ccccc1>>O=C(CCCN1CCC(c2ccc(Cc3ccc(F)cc3)cc2)CC1)Nc1ccccc1Cc1ccccc1 | C(C1=CC=CC=C1)C1=C(C=CC=C1)NC(CCCBr)=O.FC1=CC=C(C=C1)CC1=CC=C(C=C1)C1CCNCC1>>C(C1=CC=CC=C1)C1=C(C=CC=C1)NC(CCCN1CCC(CC1)C1=CC=C(C=C1)CC1=CC=C(C=C1)F)=O | [NH:6]1[CH2:7][CH2:8][CH:9]([c:10]2[cH:11][cH:12][c:13]([CH2:14][c:15]3[cH:16][cH:17][c:18]([F:19])[cH:20][cH:21]3)[cH:22][cH:23]2)[CH2:24][CH2:25]1.Br[CH2:5][CH2:4][CH2:3][C:2](=[O:1])[NH:26][c:27]1[cH:28][cH:29][cH:30][cH:31][c:32]1[CH2:33][c:34]1[cH:35][cH:36][cH:37][cH:38][cH:39]1>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5]... | Fc1ccc(Cc2ccc(C3CCNCC3)cc2)cc1.O=C(CCCBr)Nc1ccccc1Cc1ccccc1 | O=C(CCCN1CCC(c2ccc(Cc3ccc(F)cc3)cc2)CC1)Nc1ccccc1Cc1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CCCN1CCC(c2ccc(Cc3ccccc3)cc2)CC1)Nc1ccccc1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4](-[#7:5])=[O;D1;H0:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[#7:5]-[C:4](=[O;D1;H0:6])-[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:9](-[C:8]-[C:7])-[C:10]-[C:11] | null | [] | null | null | null | null | The compound (11) synthesized in Reference Example 11 and the compound (7) synthesized in Reference Example 7 were used to produce the above compound in the same way as Example 1.
Conditions: See reaction.notes.procedure_details.
Workup: to produce the above compound in the same way as Example 1 | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HBr | null | null | null | Fc1ccc(Cc2ccc(C3CCNCC3)cc2)cc1.O=C(CCCBr)Nc1ccccc1Cc1ccccc1>>O=C(CCCN1CCC(c2ccc(Cc3ccc(F)cc3)cc2)CC1)Nc1ccccc1Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-937370f078274c62816936c097f14697 | C1=C(c2ccc(Oc3ccccc3)cc2)CCNC1.O=C(CCCCCBr)Nc1ccccc1Cc1ccccc1>>O=C(CCCCCN1CC=C(c2ccc(Oc3ccccc3)cc2)CC1)Nc1ccccc1Cc1ccccc1 | C(C1=CC=CC=C1)C1=C(C=CC=C1)NC(CCCCCBr)=O.O(C1=CC=CC=C1)C1=CC=C(C=C1)C=1CCNCC1>>C(C1=CC=CC=C1)C1=C(C=CC=C1)NC(CCCCCN1CCC(=CC1)C1=CC=C(C=C1)OC1=CC=CC=C1)=O | [NH:8]1[CH2:9][CH:10]=[C:11]([c:12]2[cH:13][cH:14][c:15]([O:16][c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[cH:23][cH:24]2)[CH2:25][CH2:26]1.Br[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2](=[O:1])[NH:27][c:28]1[cH:29][cH:30][cH:31][cH:32][c:33]1[CH2:34][c:35]1[cH:36][cH:37][cH:38][cH:39][cH:40]1>>[O:1]=[C:2]([CH2:3][CH2:4][... | C1=C(c2ccc(Oc3ccccc3)cc2)CCNC1.O=C(CCCCCBr)Nc1ccccc1Cc1ccccc1 | O=C(CCCCCN1CC=C(c2ccc(Oc3ccccc3)cc2)CC1)Nc1ccccc1Cc1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 8654cc80599d789a53d1ba976beafc80caf5e8f4841be95ae420fabbb64ff19c | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CCCCCN1CC=C(c2ccc(Oc3ccccc3)cc2)CC1)Nc1ccccc1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[c:4]-[C:5]1=[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:9]-[C:10]-[C:5](-[c:4])=[C:6]-[C:7]-1 | null | [] | null | null | null | null | The compound (12) synthesized in Reference Example 12 and the compound (3) synthesized in Reference Example 3 were used to produce the above compound in the same way as Example 1.
Conditions: See reaction.notes.procedure_details.
Workup: to produce the above compound in the same way as Example 1 | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1=CCNCC1 | C1=CC[NH]CC1 | C1=CC[NH]CC1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HBr | null | null | null | C1=C(c2ccc(Oc3ccccc3)cc2)CCNC1.O=C(CCCCCBr)Nc1ccccc1Cc1ccccc1>>O=C(CCCCCN1CC=C(c2ccc(Oc3ccccc3)cc2)CC1)Nc1ccccc1Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ec5a4db79f2f4bb89fc58fd4e13d8f7e | O=C(CCCCCBr)Nc1ccccc1Cc1ccccc1.c1ccc(Oc2ccc(C3CCNCC3)cc2)cc1>>O=C(CCCCCN1CCC(c2ccc(Oc3ccccc3)cc2)CC1)Nc1ccccc1Cc1ccccc1 | C(C1=CC=CC=C1)C1=C(C=CC=C1)NC(CCCCCBr)=O.O(C1=CC=CC=C1)C1=CC=C(C=C1)C1CCNCC1>>C(C1=CC=CC=C1)C1=C(C=CC=C1)NC(CCCCCN1CCC(CC1)C1=CC=C(C=C1)OC1=CC=CC=C1)=O | Br[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2](=[O:1])[NH:27][c:28]1[cH:29][cH:30][cH:31][cH:32][c:33]1[CH2:34][c:35]1[cH:36][cH:37][cH:38][cH:39][cH:40]1.[NH:8]1[CH2:9][CH2:10][CH:11]([c:12]2[cH:13][cH:14][c:15]([O:16][c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[cH:23][cH:24]2)[CH2:25][CH2:26]1>>[O:1]=[C:2]([CH2:3][CH2:4]... | O=C(CCCCCBr)Nc1ccccc1Cc1ccccc1.c1ccc(Oc2ccc(C3CCNCC3)cc2)cc1 | O=C(CCCCCN1CCC(c2ccc(Oc3ccccc3)cc2)CC1)Nc1ccccc1Cc1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CCCCCN1CCC(c2ccc(Oc3ccccc3)cc2)CC1)Nc1ccccc1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]-[C:3])-[C:7]-[C:8] | null | [] | null | null | null | null | The compound (12) synthesized in Reference Example 12 and the compound (4) synthesized in Reference Example 4 were used to produce the above compound in the same way as Example 1.
Conditions: See reaction.notes.procedure_details.
Workup: to produce the above compound in the same way as Example 1 | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HBr | null | null | null | O=C(CCCCCBr)Nc1ccccc1Cc1ccccc1.c1ccc(Oc2ccc(C3CCNCC3)cc2)cc1>>O=C(CCCCCN1CCC(c2ccc(Oc3ccccc3)cc2)CC1)Nc1ccccc1Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4e9e448f686b4d538c557bf57797f3cf | Fc1ccc(Cc2ccc(N3CCNCC3)cc2)cc1.O=C(CCCCCBr)Nc1ccccc1Cc1ccccc1>>O=C(CCCCCN1CCN(c2ccc(Cc3ccc(F)cc3)cc2)CC1)Nc1ccccc1Cc1ccccc1 | C(C1=CC=CC=C1)C1=C(C=CC=C1)NC(CCCCCBr)=O.FC1=CC=C(C=C1)CC1=CC=C(C=C1)N1CCNCC1>>C(C1=CC=CC=C1)C1=C(C=CC=C1)NC(CCCCCN1CCN(CC1)C1=CC=C(C=C1)CC1=CC=C(C=C1)F)=O | [NH:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][cH:14][c:15]([CH2:16][c:17]3[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]3)[cH:24][cH:25]2)[CH2:26][CH2:27]1.Br[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2](=[O:1])[NH:28][c:29]1[cH:30][cH:31][cH:32][cH:33][c:34]1[CH2:35][c:36]1[cH:37][cH:38][cH:39][cH:40][cH:41]1>>[O:1]=[C:2]([CH2:3... | Fc1ccc(Cc2ccc(N3CCNCC3)cc2)cc1.O=C(CCCCCBr)Nc1ccccc1Cc1ccccc1 | O=C(CCCCCN1CCN(c2ccc(Cc3ccc(F)cc3)cc2)CC1)Nc1ccccc1Cc1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CCCCCN1CCN(c2ccc(Cc3ccccc3)cc2)CC1)Nc1ccccc1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:8]-[C:9]-[#7:4]-[C:5]-[C:6]-1 | null | [] | null | null | null | null | The compound (12) synthesized in Reference Example 12 and the compound (5) synthesized in Reference Example 5 were used to produce the above compound in the same way as Example 1.
Conditions: See reaction.notes.procedure_details.
Workup: to produce the above compound in the same way as Example 1 | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HBr | null | null | null | Fc1ccc(Cc2ccc(N3CCNCC3)cc2)cc1.O=C(CCCCCBr)Nc1ccccc1Cc1ccccc1>>O=C(CCCCCN1CCN(c2ccc(Cc3ccc(F)cc3)cc2)CC1)Nc1ccccc1Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-95c8b69826134b41adbfc5c10d2f07c1 | Cc1cccc(Cc2ccccc2)c1NC(=O)CBr.c1ccc(Oc2ccc(C3CCNCC3)cc2)cc1>>Cc1cccc(Cc2ccccc2)c1NC(=O)CN1CCC(c2ccc(Oc3ccccc3)cc2)CC1 | C(C1=CC=CC=C1)C1=C(C(=CC=C1)C)NC(CBr)=O.O(C1=CC=CC=C1)C1=CC=C(C=C1)C1CCNCC1>>C(C1=CC=CC=C1)C1=C(C(=CC=C1)C)NC(CN1CCC(CC1)C1=CC=C(C=C1)OC1=CC=CC=C1)=O | Br[CH2:18][C:16]([NH:15][c:14]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][c:6]1[CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)=[O:17].[NH:19]1[CH2:20][CH2:21][CH:22]([c:23]2[cH:24][cH:25][c:26]([O:27][c:28]3[cH:29][cH:30][cH:31][cH:32][cH:33]3)[cH:34][cH:35]2)[CH2:36][CH2:37]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][c:8]... | Cc1cccc(Cc2ccccc2)c1NC(=O)CBr.c1ccc(Oc2ccc(C3CCNCC3)cc2)cc1 | Cc1cccc(Cc2ccccc2)c1NC(=O)CN1CCC(c2ccc(Oc3ccccc3)cc2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CN1CCC(c2ccc(Oc3ccccc3)cc2)CC1)Nc1ccccc1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5])-[C:9]-[C:10] | null | [] | null | null | null | null | The compound (13) synthesized in Reference Example 13 and the compound (4) synthesized in Reference Example 4 were used to produce the above compound in the same way as Example 1.
Conditions: See reaction.notes.procedure_details.
Workup: to produce the above compound in the same way as Example 1 | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HBr | null | null | null | Cc1cccc(Cc2ccccc2)c1NC(=O)CBr.c1ccc(Oc2ccc(C3CCNCC3)cc2)cc1>>Cc1cccc(Cc2ccccc2)c1NC(=O)CN1CCC(c2ccc(Oc3ccccc3)cc2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9a1a91e08816448db252b1631a3355d4 | Cc1cccc(Cc2ccccc2)c1NC(=O)CCCCl.c1ccc(Oc2ccc(C3CCNCC3)cc2)cc1>>Cc1cccc(Cc2ccccc2)c1NC(=O)CCCN1CCC(c2ccc(Oc3ccccc3)cc2)CC1 | C(C1=CC=CC=C1)C1=C(C(=CC=C1)C)NC(CCCCl)=O.O(C1=CC=CC=C1)C1=CC=C(C=C1)C1CCNCC1>>C(C1=CC=CC=C1)C1=C(C(=CC=C1)C)NC(CCCN1CCC(CC1)C1=CC=C(C=C1)OC1=CC=CC=C1)=O | Cl[CH2:20][CH2:19][CH2:18][C:16]([NH:15][c:14]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][c:6]1[CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)=[O:17].[NH:21]1[CH2:22][CH2:23][CH:24]([c:25]2[cH:26][cH:27][c:28]([O:29][c:30]3[cH:31][cH:32][cH:33][cH:34][cH:35]3)[cH:36][cH:37]2)[CH2:38][CH2:39]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c... | Cc1cccc(Cc2ccccc2)c1NC(=O)CCCCl.c1ccc(Oc2ccc(C3CCNCC3)cc2)cc1 | Cc1cccc(Cc2ccccc2)c1NC(=O)CCCN1CCC(c2ccc(Oc3ccccc3)cc2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CCCN1CCC(c2ccc(Oc3ccccc3)cc2)CC1)Nc1ccccc1Cc1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4](-[#7:5])=[O;D1;H0:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[#7:5]-[C:4](=[O;D1;H0:6])-[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:9](-[C:8]-[C:7])-[C:10]-[C:11] | null | [] | null | null | null | null | The compound (14) synthesized in Reference Example 14 and the compound (4) synthesized in Reference Example 4 were used to produce the above compound in the same way as Example 1.
Conditions: See reaction.notes.procedure_details.
Workup: to produce the above compound in the same way as Example 1 | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HCl | null | null | null | Cc1cccc(Cc2ccccc2)c1NC(=O)CCCCl.c1ccc(Oc2ccc(C3CCNCC3)cc2)cc1>>Cc1cccc(Cc2ccccc2)c1NC(=O)CCCN1CCC(c2ccc(Oc3ccccc3)cc2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0aee0a9e47044bef97598b5d38bfad3e | Cc1cccc(Cc2ccccc2)c1NC(=O)CCCCl.Fc1ccc(Cc2ccc(N3CCNCC3)cc2)cc1>>Cc1cccc(Cc2ccccc2)c1NC(=O)CCCN1CCN(c2ccc(Cc3ccc(F)cc3)cc2)CC1 | C(C1=CC=CC=C1)C1=C(C(=CC=C1)C)NC(CCCCl)=O.FC1=CC=C(C=C1)CC1=CC=C(C=C1)N1CCNCC1>>C(C1=CC=CC=C1)C1=C(C(=CC=C1)C)NC(CCCN1CCN(CC1)C1=CC=C(C=C1)CC1=CC=C(C=C1)F)=O | Cl[CH2:20][CH2:19][CH2:18][C:16]([NH:15][c:14]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][c:6]1[CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)=[O:17].[NH:21]1[CH2:22][CH2:23][N:24]([c:25]2[cH:26][cH:27][c:28]([CH2:29][c:30]3[cH:31][cH:32][c:33]([F:34])[cH:35][cH:36]3)[cH:37][cH:38]2)[CH2:39][CH2:40]1>>[CH3:1][c:2]1[cH:3][cH:4]... | Cc1cccc(Cc2ccccc2)c1NC(=O)CCCCl.Fc1ccc(Cc2ccc(N3CCNCC3)cc2)cc1 | Cc1cccc(Cc2ccccc2)c1NC(=O)CCCN1CCN(c2ccc(Cc3ccc(F)cc3)cc2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CCCN1CCN(c2ccc(Cc3ccccc3)cc2)CC1)Nc1ccccc1Cc1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4](-[#7:5])=[O;D1;H0:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[#7:5]-[C:4](=[O;D1;H0:6])-[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1 | null | [] | null | null | null | null | The compound (14) synthesized in Reference Example 14 and the compound (5) synthesized in Reference Example 5 were used to produce the above compound in the same way as Example 1.
Conditions: See reaction.notes.procedure_details.
Workup: to produce the above compound in the same way as Example 1 | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1 | HCl | null | null | null | Cc1cccc(Cc2ccccc2)c1NC(=O)CCCCl.Fc1ccc(Cc2ccc(N3CCNCC3)cc2)cc1>>Cc1cccc(Cc2ccccc2)c1NC(=O)CCCN1CCN(c2ccc(Cc3ccc(F)cc3)cc2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-42b70ec5c4314890af50156b46d84803 | Cc1cccc(C)c1NC(=O)CBr.c1ccc(Oc2ccc(C3CCNCC3)cc2)cc1>>Cc1cccc(C)c1NC(=O)CN1CCC(c2ccc(Oc3ccccc3)cc2)CC1 | CC1=C(C(=CC=C1)C)NC(CBr)=O.O(C1=CC=CC=C1)C1=CC=C(C=C1)C1CCNCC1>>CC1=C(C(=CC=C1)C)NC(CN1CCC(CC1)C1=CC=C(C=C1)OC1=CC=CC=C1)=O | Br[CH2:12][C:10]([NH:9][c:8]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][c:6]1[CH3:7])=[O:11].[NH:13]1[CH2:14][CH2:15][CH:16]([c:17]2[cH:18][cH:19][c:20]([O:21][c:22]3[cH:23][cH:24][cH:25][cH:26][cH:27]3)[cH:28][cH:29]2)[CH2:30][CH2:31]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH3:7])[c:8]1[NH:9][C:10](=[O:11])[CH2:12][N:13]1[CH2:... | Cc1cccc(C)c1NC(=O)CBr.c1ccc(Oc2ccc(C3CCNCC3)cc2)cc1 | Cc1cccc(C)c1NC(=O)CN1CCC(c2ccc(Oc3ccccc3)cc2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CN1CCC(c2ccc(Oc3ccccc3)cc2)CC1)Nc1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5])-[C:9]-[C:10] | null | [] | null | null | null | null | The compound (18) synthesized in Reference Example 18 and the compound (4) synthesized in Reference Example 4 were used to produce the above compound in the same way as Example 1.
Conditions: See reaction.notes.procedure_details.
Workup: to produce the above compound in the same way as Example 1 | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HBr | null | null | null | Cc1cccc(C)c1NC(=O)CBr.c1ccc(Oc2ccc(C3CCNCC3)cc2)cc1>>Cc1cccc(C)c1NC(=O)CN1CCC(c2ccc(Oc3ccccc3)cc2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-63ce7425d0de4ff99768647be804a6c5 | Cc1cccc(C)c1NC(=O)CBr.Fc1ccc(Cc2ccc(N3CCNCC3)cc2)cc1>>Cc1cccc(C)c1NC(=O)CN1CCN(c2ccc(Cc3ccc(F)cc3)cc2)CC1 | CC1=C(C(=CC=C1)C)NC(CBr)=O.FC1=CC=C(C=C1)CC1=CC=C(C=C1)N1CCNCC1>>CC1=C(C(=CC=C1)C)NC(CN1CCN(CC1)C1=CC=C(C=C1)CC1=CC=C(C=C1)F)=O | Br[CH2:12][C:10]([NH:9][c:8]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][c:6]1[CH3:7])=[O:11].[NH:13]1[CH2:14][CH2:15][N:16]([c:17]2[cH:18][cH:19][c:20]([CH2:21][c:22]3[cH:23][cH:24][c:25]([F:26])[cH:27][cH:28]3)[cH:29][cH:30]2)[CH2:31][CH2:32]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH3:7])[c:8]1[NH:9][C:10](=[O:11])[CH2:12][N:1... | Cc1cccc(C)c1NC(=O)CBr.Fc1ccc(Cc2ccc(N3CCNCC3)cc2)cc1 | Cc1cccc(C)c1NC(=O)CN1CCN(c2ccc(Cc3ccc(F)cc3)cc2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CN1CCN(c2ccc(Cc3ccccc3)cc2)CC1)Nc1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[O;D1;H0:3]=[C:2](-[#7:4]-[c:5])-[CH2;D2;+0:1]-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1 | null | [] | null | null | null | null | The compound (18) synthesized in Reference Example 18 and the compound (5) synthesized in Reference Example 5 were used to produce the above compound in the same way as Example 1.
Conditions: See reaction.notes.procedure_details.
Workup: to produce the above compound in the same way as Example 1 | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1 | HBr | null | null | null | Cc1cccc(C)c1NC(=O)CBr.Fc1ccc(Cc2ccc(N3CCNCC3)cc2)cc1>>Cc1cccc(C)c1NC(=O)CN1CCN(c2ccc(Cc3ccc(F)cc3)cc2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-29980035cd8743d88cbb26a64e2988b5 | Fc1ccc(Cc2ccc(N3CCNCC3)cc2)cc1.O=C(CBr)N1CCCOc2ccccc21>>O=C(CN1CCN(c2ccc(Cc3ccc(F)cc3)cc2)CC1)N1CCCOc2ccccc21 | BrCC(=O)N1CCCOC2=C1C=CC=C2.FC1=CC=C(C=C1)CC1=CC=C(C=C1)N1CCNCC1>>FC1=CC=C(C=C1)CC1=CC=C(C=C1)N1CCN(CC1)CC(=O)N1CCCOC2=C1C=CC=C2 | [NH:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][c:11]([CH2:12][c:13]3[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]3)[cH:20][cH:21]2)[CH2:22][CH2:23]1.Br[CH2:3][C:2](=[O:1])[N:24]1[CH2:25][CH2:26][CH2:27][O:28][c:29]2[cH:30][cH:31][cH:32][cH:33][c:34]21>>[O:1]=[C:2]([CH2:3][N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][c:11]... | Fc1ccc(Cc2ccc(N3CCNCC3)cc2)cc1.O=C(CBr)N1CCCOc2ccccc21 | O=C(CN1CCN(c2ccc(Cc3ccc(F)cc3)cc2)CC1)N1CCCOc2ccccc21 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CN1CCN(c2ccc(Cc3ccccc3)cc2)CC1)N1CCCOc2ccccc21 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C:5])-[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[C:5]-[#7:4](-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1)-[c:6] | null | [] | null | null | null | null | The compound (15) synthesized in Reference Example and the compound (5) synthesized in Reference Example were used to produce the above compound in the same way as Example 1.
Conditions: See reaction.notes.procedure_details.
Workup: to produce the above compound in the same way as Example 1 | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1.c1ccc2c(c1)[NH]CCCO2 | HBr | null | null | null | Fc1ccc(Cc2ccc(N3CCNCC3)cc2)cc1.O=C(CBr)N1CCCOc2ccccc21>>O=C(CN1CCN(c2ccc(Cc3ccc(F)cc3)cc2)CC1)N1CCCOc2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e1dcf3764cea4e59a631d89d7f2b7e7d | O=C(CCCCl)N1CCCOc2ccccc21.c1ccc(Oc2ccc(C3CCNCC3)cc2)cc1>>O=C(CCCN1CCC(c2ccc(Oc3ccccc3)cc2)CC1)N1CCCOc2ccccc21 | ClCCCC(=O)N1CCCOC2=C1C=CC=C2.O(C1=CC=CC=C1)C1=CC=C(C=C1)C1CCNCC1>>O(C1=CC=CC=C1)C1=CC=C(C=C1)C1CCN(CC1)CCCC(=O)N1CCCOC2=C1C=CC=C2 | Cl[CH2:5][CH2:4][CH2:3][C:2](=[O:1])[N:25]1[CH2:26][CH2:27][CH2:28][O:29][c:30]2[cH:31][cH:32][cH:33][cH:34][c:35]21.[NH:6]1[CH2:7][CH2:8][CH:9]([c:10]2[cH:11][cH:12][c:13]([O:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[cH:21][cH:22]2)[CH2:23][CH2:24]1>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][CH:9]([c... | O=C(CCCCl)N1CCCOc2ccccc21.c1ccc(Oc2ccc(C3CCNCC3)cc2)cc1 | O=C(CCCN1CCC(c2ccc(Oc3ccccc3)cc2)CC1)N1CCCOc2ccccc21 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CCCN1CCC(c2ccc(Oc3ccccc3)cc2)CC1)N1CCCOc2ccccc21 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4](-[#7:5])=[O;D1;H0:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[#7:5]-[C:4](=[O;D1;H0:6])-[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:9](-[C:8]-[C:7])-[C:10]-[C:11] | null | [] | null | null | null | null | The compound (16) synthesized in Reference Example 16 and the compound (4) synthesized in Reference Example 4 were used to produce the above compound in the same way as Example 1.
Conditions: See reaction.notes.procedure_details.
Workup: to produce the above compound in the same way as Example 1 | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.c1ccccc1.c1ccc2c(c1)[NH]CCCO2 | HCl | null | null | null | O=C(CCCCl)N1CCCOc2ccccc21.c1ccc(Oc2ccc(C3CCNCC3)cc2)cc1>>O=C(CCCN1CCC(c2ccc(Oc3ccccc3)cc2)CC1)N1CCCOc2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e55b92dd5753463f9e20cccc10543c7b | O=C(CCCCl)N1CCCOc2ccccc21.c1ccc(Oc2ccc(N3CCNCC3)cc2)cc1>>O=C(CCCN1CCN(c2ccc(Oc3ccccc3)cc2)CC1)N1CCCOc2ccccc21 | ClCCCC(=O)N1CCCOC2=C1C=CC=C2.O(C1=CC=CC=C1)C1=CC=C(C=C1)N1CCNCC1>>O(C1=CC=CC=C1)C1=CC=C(C=C1)N1CCN(CC1)CCCC(=O)N1CCCOC2=C1C=CC=C2 | Cl[CH2:5][CH2:4][CH2:3][C:2](=[O:1])[N:25]1[CH2:26][CH2:27][CH2:28][O:29][c:30]2[cH:31][cH:32][cH:33][cH:34][c:35]21.[NH:6]1[CH2:7][CH2:8][N:9]([c:10]2[cH:11][cH:12][c:13]([O:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[cH:21][cH:22]2)[CH2:23][CH2:24]1>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][N:9]([c:1... | O=C(CCCCl)N1CCCOc2ccccc21.c1ccc(Oc2ccc(N3CCNCC3)cc2)cc1 | O=C(CCCN1CCN(c2ccc(Oc3ccccc3)cc2)CC1)N1CCCOc2ccccc21 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CCCN1CCN(c2ccc(Oc3ccccc3)cc2)CC1)N1CCCOc2ccccc21 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4](-[#7:5])=[O;D1;H0:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[#7:5]-[C:4](=[O;D1;H0:6])-[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1 | null | [] | null | null | null | null | The compound (16) synthesized in Reference Example 16 and 1-(4-phenoxylphenyl)piperazine [DE 2631885] were used to produce the above compound in the same way as Example 1.
Conditions: See reaction.notes.procedure_details.
Workup: to produce the above compound in the same way as Example 1 | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1.c1ccc2c(c1)[NH]CCCO2 | HCl | null | null | null | O=C(CCCCl)N1CCCOc2ccccc21.c1ccc(Oc2ccc(N3CCNCC3)cc2)cc1>>O=C(CCCN1CCN(c2ccc(Oc3ccccc3)cc2)CC1)N1CCCOc2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-eb6b76f4e5d04dfb88c2dcb703a6d60d | Fc1ccc(Cc2ccc(N3CCNCC3)cc2)cc1.O=C(CCCCl)N1CCCOc2ccccc21>>O=C(CCCN1CCN(c2ccc(Cc3ccc(F)cc3)cc2)CC1)N1CCCOc2ccccc21 | ClCCCC(=O)N1CCCOC2=C1C=CC=C2.FC1=CC=C(C=C1)CC1=CC=C(C=C1)N1CCNCC1>>FC1=CC=C(C=C1)CC1=CC=C(C=C1)N1CCN(CC1)CCCC(=O)N1CCCOC2=C1C=CC=C2 | [NH:6]1[CH2:7][CH2:8][N:9]([c:10]2[cH:11][cH:12][c:13]([CH2:14][c:15]3[cH:16][cH:17][c:18]([F:19])[cH:20][cH:21]3)[cH:22][cH:23]2)[CH2:24][CH2:25]1.Cl[CH2:5][CH2:4][CH2:3][C:2](=[O:1])[N:26]1[CH2:27][CH2:28][CH2:29][O:30][c:31]2[cH:32][cH:33][cH:34][cH:35][c:36]21>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][... | Fc1ccc(Cc2ccc(N3CCNCC3)cc2)cc1.O=C(CCCCl)N1CCCOc2ccccc21 | O=C(CCCN1CCN(c2ccc(Cc3ccc(F)cc3)cc2)CC1)N1CCCOc2ccccc21 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CCCN1CCN(c2ccc(Cc3ccccc3)cc2)CC1)N1CCCOc2ccccc21 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4](-[#7:5])=[O;D1;H0:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[#7:5]-[C:4](=[O;D1;H0:6])-[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1 | null | [] | null | null | null | null | The compound (16) synthesized in Reference Example 16 and the compound (5) synthesized in Reference Example 5 were used to produce the above compound in the same way as Example 1.
Conditions: See reaction.notes.procedure_details.
Workup: to produce the above compound in the same way as Example 1 | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1.c1ccc2c(c1)[NH]CCCO2 | HCl | null | null | null | Fc1ccc(Cc2ccc(N3CCNCC3)cc2)cc1.O=C(CCCCl)N1CCCOc2ccccc21>>O=C(CCCN1CCN(c2ccc(Cc3ccc(F)cc3)cc2)CC1)N1CCCOc2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1255beb210e449d39ea430d3d1fca98e | Fc1ccc(Cc2ccc(C3CCNCC3)cc2)cc1.O=C(CCCCl)N1CCCOc2ccccc21>>O=C(CCCN1CCC(c2ccc(Cc3ccc(F)cc3)cc2)CC1)N1CCCOc2ccccc21 | ClCCCC(=O)N1CCCOC2=C1C=CC=C2.FC1=CC=C(C=C1)CC1=CC=C(C=C1)C1CCNCC1>>FC1=CC=C(C=C1)CC1=CC=C(C=C1)C1CCN(CC1)CCCC(=O)N1CCCOC2=C1C=CC=C2 | [NH:6]1[CH2:7][CH2:8][CH:9]([c:10]2[cH:11][cH:12][c:13]([CH2:14][c:15]3[cH:16][cH:17][c:18]([F:19])[cH:20][cH:21]3)[cH:22][cH:23]2)[CH2:24][CH2:25]1.Cl[CH2:5][CH2:4][CH2:3][C:2](=[O:1])[N:26]1[CH2:27][CH2:28][CH2:29][O:30][c:31]2[cH:32][cH:33][cH:34][cH:35][c:36]21>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8]... | Fc1ccc(Cc2ccc(C3CCNCC3)cc2)cc1.O=C(CCCCl)N1CCCOc2ccccc21 | O=C(CCCN1CCC(c2ccc(Cc3ccc(F)cc3)cc2)CC1)N1CCCOc2ccccc21 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CCCN1CCC(c2ccc(Cc3ccccc3)cc2)CC1)N1CCCOc2ccccc21 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4](-[#7:5])=[O;D1;H0:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[#7:5]-[C:4](=[O;D1;H0:6])-[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:9](-[C:8]-[C:7])-[C:10]-[C:11] | null | [] | null | null | null | null | The compound (16) synthesized in Reference Example 16 and the compound (7) synthesized in Reference Example 7 were used to produce the above compound in the same way as Example 1.
Conditions: See reaction.notes.procedure_details.
Workup: to produce the above compound in the same way as Example 1 | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.c1ccccc1.c1ccc2c(c1)[NH]CCCO2 | HCl | null | null | null | Fc1ccc(Cc2ccc(C3CCNCC3)cc2)cc1.O=C(CCCCl)N1CCCOc2ccccc21>>O=C(CCCN1CCC(c2ccc(Cc3ccc(F)cc3)cc2)CC1)N1CCCOc2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9fdee47e3af1400fb5eacb1be913c88c | Fc1ccc(Cc2ccc(N3CCNCC3)cc2)cc1.O=S(=O)(CCCCl)N1CCCOc2ccccc21>>O=S(=O)(CCCN1CCN(c2ccc(Cc3ccc(F)cc3)cc2)CC1)N1CCCOc2ccccc21 | ClCCCS(=O)(=O)N1CCCOC2=C1C=CC=C2.FC1=CC=C(C=C1)CC1=CC=C(C=C1)N1CCNCC1>>FC1=CC=C(C=C1)CC1=CC=C(C=C1)N1CCN(CC1)CCCS(=O)(=O)N1CCCOC2=C1C=CC=C2 | [NH:7]1[CH2:8][CH2:9][N:10]([c:11]2[cH:12][cH:13][c:14]([CH2:15][c:16]3[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]3)[cH:23][cH:24]2)[CH2:25][CH2:26]1.Cl[CH2:6][CH2:5][CH2:4][S:2](=[O:1])(=[O:3])[N:27]1[CH2:28][CH2:29][CH2:30][O:31][c:32]2[cH:33][cH:34][cH:35][cH:36][c:37]21>>[O:1]=[S:2](=[O:3])([CH2:4][CH2:5][CH2:6][N:7... | Fc1ccc(Cc2ccc(N3CCNCC3)cc2)cc1.O=S(=O)(CCCCl)N1CCCOc2ccccc21 | O=S(=O)(CCCN1CCN(c2ccc(Cc3ccc(F)cc3)cc2)CC1)N1CCCOc2ccccc21 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=S(=O)(CCCN1CCN(c2ccc(Cc3ccccc3)cc2)CC1)N1CCCOc2ccccc21 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | null | [] | null | null | null | null | The compound (17) synthesized in Reference Example 17 and the compound (5) synthesized in Reference Example 5 were used to produce the above compound in the same way as Example 1.
Conditions: See reaction.notes.procedure_details.
Workup: to produce the above compound in the same way as Example 1 | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1.c1ccc2c(c1)[NH]CCCO2 | HCl | null | null | null | Fc1ccc(Cc2ccc(N3CCNCC3)cc2)cc1.O=S(=O)(CCCCl)N1CCCOc2ccccc21>>O=S(=O)(CCCN1CCN(c2ccc(Cc3ccc(F)cc3)cc2)CC1)N1CCCOc2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-06001c8a7a0d41e09c2cfab5cdeefd53 | O=C(CBr)Nc1ccccc1.c1ccc(Oc2ccc(C3CCNCC3)cc2)cc1>>O=C(CN1CCC(c2ccc(Oc3ccccc3)cc2)CC1)Nc1ccccc1 | O(C1=CC=CC=C1)C1=CC=C(C=C1)C1CCNCC1.C1(=CC=CC=C1)NC(CBr)=O>>C1(=CC=CC=C1)NC(CN1CCC(CC1)C1=CC=C(C=C1)OC1=CC=CC=C1)=O | Br[CH2:3][C:2](=[O:1])[NH:23][c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1.[NH:4]1[CH2:5][CH2:6][CH:7]([c:8]2[cH:9][cH:10][c:11]([O:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19][cH:20]2)[CH2:21][CH2:22]1>>[O:1]=[C:2]([CH2:3][N:4]1[CH2:5][CH2:6][CH:7]([c:8]2[cH:9][cH:10][c:11]([O:12][c:13]3[cH:14][cH:15][cH:16][c... | O=C(CBr)Nc1ccccc1.c1ccc(Oc2ccc(C3CCNCC3)cc2)cc1 | O=C(CN1CCC(c2ccc(Oc3ccccc3)cc2)CC1)Nc1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CN1CCC(c2ccc(Oc3ccccc3)cc2)CC1)Nc1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5])-[C:9]-[C:10] | null | [] | null | null | null | null | The compound (4) synthesized in Reference Example 4 and the compound (23) synthesized in Reference Example 23 were used to produce the above compound in the same way as Example 1.
Conditions: See reaction.notes.procedure_details.
Workup: to produce the above compound in the same way as Example 1 | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.c1ccccc1.c1ccccc1 | HBr | null | null | null | O=C(CBr)Nc1ccccc1.c1ccc(Oc2ccc(C3CCNCC3)cc2)cc1>>O=C(CN1CCC(c2ccc(Oc3ccccc3)cc2)CC1)Nc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0dbe0dca9fae46829877e914cdfc371e | Fc1ccc(Cc2ccc(C3CCNCC3)cc2)cc1.O=C(CBr)Nc1ccccc1>>O=C(CN1CCC(c2ccc(Cc3ccc(F)cc3)cc2)CC1)Nc1ccccc1 | FC1=CC=C(C=C1)CC1=CC=C(C=C1)C1CCNCC1.C1(=CC=CC=C1)NC(CBr)=O>>C1(=CC=CC=C1)NC(CN1CCC(CC1)C1=CC=C(C=C1)CC1=CC=C(C=C1)F)=O | [NH:4]1[CH2:5][CH2:6][CH:7]([c:8]2[cH:9][cH:10][c:11]([CH2:12][c:13]3[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]3)[cH:20][cH:21]2)[CH2:22][CH2:23]1.Br[CH2:3][C:2](=[O:1])[NH:24][c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1>>[O:1]=[C:2]([CH2:3][N:4]1[CH2:5][CH2:6][CH:7]([c:8]2[cH:9][cH:10][c:11]([CH2:12][c:13]3[cH:14][cH:1... | Fc1ccc(Cc2ccc(C3CCNCC3)cc2)cc1.O=C(CBr)Nc1ccccc1 | O=C(CN1CCC(c2ccc(Cc3ccc(F)cc3)cc2)CC1)Nc1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CN1CCC(c2ccc(Cc3ccccc3)cc2)CC1)Nc1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5])-[C:9]-[C:10] | null | [] | null | null | null | null | The compound (7) synthesized in Reference Example 7 and the compound (23) synthesized in Reference Example 23 were used to produce the above compound in the same way as Example 1.
Conditions: See reaction.notes.procedure_details.
Workup: to produce the above compound in the same way as Example 1 | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.c1ccccc1.c1ccccc1 | HBr | null | null | null | Fc1ccc(Cc2ccc(C3CCNCC3)cc2)cc1.O=C(CBr)Nc1ccccc1>>O=C(CN1CCC(c2ccc(Cc3ccc(F)cc3)cc2)CC1)Nc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d49e044d91ba41819787fce94b25dafb | CC(C)c1cccc(C(C)C)c1NC(=O)CBr.c1ccc(Oc2ccc(C3CCNCC3)cc2)cc1>>CC(C)c1cccc(C(C)C)c1NC(=O)CN1CCC(c2ccc(Oc3ccccc3)cc2)CC1 | O(C1=CC=CC=C1)C1=CC=C(C=C1)C1CCNCC1.C(C)(C)C1=C(C(=CC=C1)C(C)C)NC(CBr)=O>>C(C)(C)C1=C(C(=CC=C1)C(C)C)NC(CN1CCC(CC1)C1=CC=C(C=C1)OC1=CC=CC=C1)=O | Br[CH2:16][C:14]([NH:13][c:12]1[c:4]([CH:2]([CH3:1])[CH3:3])[cH:5][cH:6][cH:7][c:8]1[CH:9]([CH3:10])[CH3:11])=[O:15].[NH:17]1[CH2:18][CH2:19][CH:20]([c:21]2[cH:22][cH:23][c:24]([O:25][c:26]3[cH:27][cH:28][cH:29][cH:30][cH:31]3)[cH:32][cH:33]2)[CH2:34][CH2:35]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([CH:9]... | CC(C)c1cccc(C(C)C)c1NC(=O)CBr.c1ccc(Oc2ccc(C3CCNCC3)cc2)cc1 | CC(C)c1cccc(C(C)C)c1NC(=O)CN1CCC(c2ccc(Oc3ccccc3)cc2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CN1CCC(c2ccc(Oc3ccccc3)cc2)CC1)Nc1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5])-[C:9]-[C:10] | null | [] | null | null | null | null | The compound (4) synthesized in Reference Example 4 and the compound (24) synthesized in Reference Example 24 were used to produce the above compound in the same way as Example 1.
Conditions: See reaction.notes.procedure_details.
Workup: to produce the above compound in the same way as Example 1 | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HBr | null | null | null | CC(C)c1cccc(C(C)C)c1NC(=O)CBr.c1ccc(Oc2ccc(C3CCNCC3)cc2)cc1>>CC(C)c1cccc(C(C)C)c1NC(=O)CN1CCC(c2ccc(Oc3ccccc3)cc2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-dfe2b6a956a846edadea6b92fc42ad40 | C=C(c1ccccc1)N(C)C(=O)CBr.c1ccc(Oc2ccc(C3CCNCC3)cc2)cc1>>C=C(c1ccccc1)N(C)C(=O)CN1CCC(c2ccc(Oc3ccccc3)cc2)CC1 | O(C1=CC=CC=C1)C1=CC=C(C=C1)C1CCNCC1.CN(C(CBr)=O)C(=C)C1=CC=CC=C1>>CN(C(CN1CCC(CC1)C1=CC=C(C=C1)OC1=CC=CC=C1)=O)C(=C)C1=CC=CC=C1 | Br[CH2:13][C:11]([N:9]([C:2](=[CH2:1])[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[CH3:10])=[O:12].[NH:14]1[CH2:15][CH2:16][CH:17]([c:18]2[cH:19][cH:20][c:21]([O:22][c:23]3[cH:24][cH:25][cH:26][cH:27][cH:28]3)[cH:29][cH:30]2)[CH2:31][CH2:32]1>>[CH2:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[N:9]([CH3:10])[C:11](=[O:12])... | C=C(c1ccccc1)N(C)C(=O)CBr.c1ccc(Oc2ccc(C3CCNCC3)cc2)cc1 | C=C(c1ccccc1)N(C)C(=O)CN1CCC(c2ccc(Oc3ccccc3)cc2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | C=C(NC(=O)CN1CCC(c2ccc(Oc3ccccc3)cc2)CC1)c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C;D1;H3:5])-[C:6]=[C;D1;H2:7].[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]>>[C:8]-[C:9]-[N;H0;D3;+0:10](-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C;D1;H3:5])-[C:6]=[C;D1;H2:7])-[C:11]-[C:12] | null | [] | null | null | null | null | The compound (4) synthesized in Reference Example 4 and the compound (25) synthesized in Reference Example 25 were used to produce the above compound in the same way as Example 1.
Conditions: See reaction.notes.procedure_details.
Workup: to produce the above compound in the same way as Example 1 | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HBr | null | null | null | C=C(c1ccccc1)N(C)C(=O)CBr.c1ccc(Oc2ccc(C3CCNCC3)cc2)cc1>>C=C(c1ccccc1)N(C)C(=O)CN1CCC(c2ccc(Oc3ccccc3)cc2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-15ef5e371941461d87787ec3f8b02012 | Brc1csc2ccccc12>>c1ccc2sccc2c1 | BrC=1C2=C(SC1)C=CC=C2.C(C1=CC=CC=C1)OC1=CC=C(C=C1)O>>S1C2=C(C=C1)C=CC=C2 | Br[c:7]1[cH:6][s:5][c:4]2[cH:3][cH:2][cH:1][cH:9][c:8]21>>[cH:1]1[cH:2][cH:3][c:4]2[s:5][cH:6][cH:7][c:8]2[cH:9]1 | Brc1csc2ccccc12 | c1ccc2sccc2c1 | null | null | N1=C(C=C(C=C1C)C)C.C(C)(=O)OCC | Functional Group Interconversion | Aromatic dehalogenation | ab6c258853a046ce112a28199ff0524dc13007f2a0961d19b739094801efd0b3 | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1ccc2sccc2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#16;a:3]:[c:4](:[c:5]):[c:6]:1:[c:7]>>[c:5]:[c:4]1:[#16;a:3]:[c:2]:[cH;D2;+0:1]:[c:6]:1:[c:7] | 35 | [{"value": 28.0, "product": "S1C2=C(C=C1)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}, {"value": 35.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 3-bromo-benzo[b]thiophene (69.62 g, 0.325 mol) in 55 mL of anhydrous collidine under N2 was added 4-benzyloxyphenol (97.6 g, 0.488 mol) and cuprous oxide (23.3 g, 0.163 mol). The mixture was heated to reflux for 24 hours. Upon cooling, the reaction mixture was diluted with ethyl acetate (200 mL) and th... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccc2sccc2c1 | c1ccc2sccc2c1 | c1ccc2sccc2c1 | Br- | N1=C(C=C(C=C1C)C)C.C(C)(=O)OCC | null | null | Brc1csc2ccccc12>N1=C(C=C(C=C1C)C)C.C(C)(=O)OCC>c1ccc2sccc2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b667ae6e1894401594ee757404717db3 | CC(C)OB(OC(C)C)OC(C)C.COc1ccc2ccsc2c1>>COc1ccc2cc(B(O)O)sc2c1 | Cl.B(OC(C)C)(OC(C)C)OC(C)C.COC=1C=CC2=C(SC=C2)C1.C(CCC)[Li]>>COC=1C=CC2=C(SC(=C2)B(O)O)C1 | CC(C)O[B:9]([O:10]C(C)C)[O:11]C(C)C.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][s:12][c:13]2[cH:14]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][c:8]([B:9]([OH:10])[OH:11])[s:12][c:13]2[cH:14]1 | CC(C)OB(OC(C)C)OC(C)C.COc1ccc2ccsc2c1 | COc1ccc2cc(B(O)O)sc2c1 | null | null | C(C)(=O)OCC.O1CCCC1 | Functional Group Interconversion | OtherReaction | b26ae5bce1dcb596d56f0468a7e25213476888c559cebddd2abbe3c78193a94f | d6d312d46f766d2774f96de1fd96fd8f98a20e51a20ef3280f850cd6a3c77869 | c1ccc2sccc2c1 | C-C(-C)-O-[B;H0;D3;+0:1](-[O;H0;D2;+0:2]-C(-C)-C)-[O;H0;D2;+0:3]-C(-C)-C.[#16;a:4]1:[c:5]:[c:6]:[c:7]:[cH;D2;+0:8]:1>>[OH;D1;+0:2]-[B;H0;D3;+0:1](-[OH;D1;+0:3])-[c;H0;D3;+0:8]1:[#16;a:4]:[c:5]:[c:6]:[c:7]:1 | 71 | [{"value": 71.0, "product": "COC=1C=CC2=C(SC(=C2)B(O)O)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.0, "product": "COC=1C=CC2=C(SC(=C2)B(O)O)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | To a solution of 6-methoxybenzo[b]thiophene (18.13 g, 0.111 mol) in 150 mL of anhydrous tetrahydrofuran (THF) at -60° C. was added n-butyllithium (76.2 mL, 0.122 mol, 1.6M solution in hexanes), dropwise via syringe. After stirring for 30 minutes, triisopropyl borate (28.2 mL, 0.122 mol) was introduced via syringe. The ... | 10.6084/m9.figshare.5104873.v1 | null | null | Boronic acid | c1ccc2sccc2c1 | c1ccc2sccc2c1 | c1ccc2sccc2c1 | HO- | C(C)(=O)OCC.O1CCCC1 | 0 | 0.5 | CC(C)OB(OC(C)C)OC(C)C.COc1ccc2ccsc2c1>C(C)(=O)OCC.O1CCCC1>COc1ccc2cc(B(O)O)sc2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b384396be0494ddab64c768366b631a5 | Cc1ccc([N+](=O)[O-])cc1S(=O)(=O)O.[O]=[Mn](=[O])(=[O])[O-]>>O=C(O)c1c([N+](=O)[O-])cccc1S(=O)(=O)O | [Mn](=O)(=O)(=O)[O-].[K+].CC1=C(C=C(C=C1)[N+](=O)[O-])S(=O)(=O)O.C([O-])([O-])=O.[K+].[K+]>>C(=O)(O)C1=C(C=CC=C1[N+](=O)[O-])S(=O)(=O)O | [CH3:2][c:11]1[cH:10][cH:9][c:5]([N+:6](=[O:7])[O-:8])[cH:4][c:12]1[S:13](=[O:14])(=[O:15])[OH:16].[O]=[Mn](=[O])(=[O:1])[O-:3]>>[O:1]=[C:2]([OH:3])[c:4]1[c:5]([N+:6](=[O:7])[O-:8])[cH:9][cH:10][cH:11][c:12]1[S:13](=[O:14])(=[O:15])[OH:16] | Cc1ccc([N+](=O)[O-])cc1S(=O)(=O)O.[O]=[Mn](=[O])(=[O])[O-] | O=C(O)c1c([N+](=O)[O-])cccc1S(=O)(=O)O | null | null | O | Acylation | OtherReaction | b2c6c66c8e37c7be9aa90948967ec718c6f9c011dab19dcd79b9330bc269e1cd | 903e48d04e4504a4fe6977f5e5582144adff237d0488a4542a1907161cf0134c | c1ccccc1 | [#16:1]-[c:2]1:[cH;D2;+0:3]:[c:4](-[#7;+:5]):[c:6]:[c:7]:[c;H0;D3;+0:8]:1-[CH3;D1;+0:9].[O-;H0;D1:10]-[Mn](=[O;H0;D1;+0:11])(=[O])=[O]>>[#16:1]-[c:2]1:[cH;D2;+0:8]:[c:7]:[c:6]:[c:4](-[#7;+:5]):[c;H0;D3;+0:3]:1-[C;H0;D3;+0:9](=[O;H0;D1;+0:11])-[OH;D1;+0:10] | null | [] | null | null | null | null | 400.0 g (2.53 mol) of potassium permanganate are added in portions at 80° C. over a period of 2 h to a solution of 106.0 g (0.40 mol) of 2-methyl-5-nitrobenzenesulfonic acid and 80.0 g (0.58 mol) of potassium carbonate in 1300 ml of water. The reaction temperature is maintained at between 80° and 95° C.
Conditions: See... | 10.6084/m9.figshare.5104873.v1 | null | null | Carboxylic acid | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | O | null | null | Cc1ccc([N+](=O)[O-])cc1S(=O)(=O)O.[O]=[Mn](=[O])(=[O])[O-]>O>O=C(O)c1c([N+](=O)[O-])cccc1S(=O)(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ef5dd0a2d9f54429bb4780c2b3d7888b | CO.O=C(O)c1ccc([N+](=O)[O-])cc1S(=O)(=O)O>>COC(=O)c1ccc([N+](=O)[O-])cc1S(=O)(=O)O | CO.C(=O)(O)C1=C(C=C(C=C1)[N+](=O)[O-])S(=O)(=O)O.S(=O)(Cl)Cl>>COC(=O)C1=C(C=C(C=C1)[N+](=O)[O-])S(=O)(=O)O | [CH3:1][OH:2].O[C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][c:13]1[S:14](=[O:15])(=[O:16])[OH:17]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][c:13]1[S:14](=[O:15])(=[O:16])[OH:17] | CO.O=C(O)c1ccc([N+](=O)[O-])cc1S(=O)(=O)O | COC(=O)c1ccc([N+](=O)[O-])cc1S(=O)(=O)O | null | null | CN(C)C=O | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[OH;D1;+0:7]>>[C;D1;H3:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | 0 | CELSIUS | 3 | HOUR | A suspension of 190.0 g (0.77 mol) of 2-carboxy-5-nitrobenzenesulfonic acid, 10 ml of DMF and 250 ml (3.43 mol) of thionyl chloride is heated at boiling for 3 h. After separating off the insoluble constituents by filtration, the filtrate is concentrated. 200 ml (4.94 mol) of methanol are added to the residue which resu... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1 | HO- | CN(C)C=O | 0 | 3 | CO.O=C(O)c1ccc([N+](=O)[O-])cc1S(=O)(=O)O>CN(C)C=O>COC(=O)c1ccc([N+](=O)[O-])cc1S(=O)(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1037934a96ff4eeaab90d7317a1e6dc9 | COC(=O)c1ccc([N+](=O)[O-])cc1S(=O)(=O)O.O=P(Cl)(Cl)Cl>>COC(=O)c1ccc([N+](=O)[O-])cc1S(=O)(=O)Cl | [OH-].[K+].COC(=O)C1=C(C=C(C=C1)[N+](=O)[O-])S(=O)(=O)O.P(=O)(Cl)(Cl)Cl>>COC(=O)C1=C(C=C(C=C1)[N+](=O)[O-])S(=O)(=O)Cl | O[S:14]([c:13]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12]1)(=[O:15])=[O:16].O=P(Cl)(Cl)[Cl:17]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][c:13]1[S:14](=[O:15])(=[O:16])[Cl:17] | COC(=O)c1ccc([N+](=O)[O-])cc1S(=O)(=O)O.O=P(Cl)(Cl)Cl | COC(=O)c1ccc([N+](=O)[O-])cc1S(=O)(=O)Cl | null | null | CO | Functional Group Interconversion | OtherReaction | 1d60417dbcce8291d459a7fb34824cf29ea6f69a30ac46aeb585ac8e7b69013e | 4a93b4a9749514113cd3dffa44b64f21b1f88d26b8739299bcad711fe7a13a1b | c1ccccc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[S;H0;D4;+0:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5](:[c:6]):[c:7]-[C:8](-[#8:9])=[O;D1;H0:10]>>[#8:9]-[C:8](=[O;D1;H0:10])-[c:7]:[c:5](-[S;H0;D4;+0:2](-[Cl;H0;D1;+0:1])(=[O;D1;H0:3])=[O;D1;H0:4]):[c:6] | null | [] | 0 | CELSIUS | 2.5 | HOUR | A solution of 17.3 g (0.27 mol) of potassium hydroxide (88% strength) and 100 ml of methanol is added carefully with vigorous stirring to a solution of 70.9 g (0.27 mol) of 2-methoxycarbonyl-5-nitrobenzenesulfonic acid in 300 ml of methanol. The mixture is cooled to 0° C. and the salt which is precipitated is filtered ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonic acid | Sulfonyl halide | null | null | c1ccccc1 | HCl | CO | 0 | 2.5 | COC(=O)c1ccc([N+](=O)[O-])cc1S(=O)(=O)O.O=P(Cl)(Cl)Cl>CO>COC(=O)c1ccc([N+](=O)[O-])cc1S(=O)(=O)Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5441fae977e64216866214e130a2476a | COC(=O)c1ccc([N+](=O)[O-])cc1S(=O)(=O)NC(C)(C)C>>COC(=O)c1ccc(N)cc1S(=O)(=O)NC(C)(C)C | C(C)(C)(C)NS(=O)(=O)C1=C(C=CC(=C1)[N+](=O)[O-])C(=O)OC.[H][H]>>C(C)(C)(C)NS(=O)(=O)C1=C(C=CC(=C1)N)C(=O)OC | O=[N+:9]([O-])[c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:11]([S:12](=[O:13])(=[O:14])[NH:15][C:16]([CH3:17])([CH3:18])[CH3:19])[cH:10]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:10][c:11]1[S:12](=[O:13])(=[O:14])[NH:15][C:16]([CH3:17])([CH3:18])[CH3:19] | COC(=O)c1ccc([N+](=O)[O-])cc1S(=O)(=O)NC(C)(C)C | COC(=O)c1ccc(N)cc1S(=O)(=O)NC(C)(C)C | null | null | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | 25.08 g (0.079 mol) of N-tert-butyl-2-methoxycarbonyl-5-nitrobenzenesulfonamide are dissolved in 1000 ml of MeOH. 0.50 g of Pd--C (10%) is added and the mixture is shaken under a hydrogen atmosphere (1 atm) until the uptake of hydrogen has finished. The catalyst is separated off and the solvent is removed by distillati... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | CO | null | null | COC(=O)c1ccc([N+](=O)[O-])cc1S(=O)(=O)NC(C)(C)C>CO>COC(=O)c1ccc(N)cc1S(=O)(=O)NC(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e6119d1ed5fd4cad8ff5deeb55d6be7b | COC(=O)c1ccc(N)cc1S(=O)(=O)NC(C)(C)C.O=CO>>COC(=O)c1ccc(NC=O)cc1S(=O)(=O)NC(C)(C)C | C(=O)O.C(C)(=O)OC(C)=O.C(C)(C)(C)NS(=O)(=O)C1=C(C=CC(=C1)N)C(=O)OC>>C(C)(C)(C)NS(=O)(=O)C1=C(C=CC(=C1)NC=O)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:12][c:13]1[S:14](=[O:15])(=[O:16])[NH:17][C:18]([CH3:19])([CH3:20])[CH3:21].O[CH:10]=[O:11]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][CH:10]=[O:11])[cH:12][c:13]1[S:14](=[O:15])(=[O:16])[NH:17][C:18]([CH3:19])([CH3:20])[CH3:21] | COC(=O)c1ccc(N)cc1S(=O)(=O)NC(C)(C)C.O=CO | COC(=O)c1ccc(NC=O)cc1S(=O)(=O)NC(C)(C)C | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccccc1 | O-[CH;D2;+0:1]=[O;D1;H0:2].[NH2;D1;+0:3]-[c:4](:[c:5]):[c:6]>>[O;D1;H0:2]=[CH;D2;+0:1]-[NH;D2;+0:3]-[c:4](:[c:5]):[c:6] | null | [] | null | null | 4 | HOUR | 6.5 ml of formic acid are carefully added at 0° C. to 13 ml of acetic anhydride. The mixture is subsequently heated at 50°-60° C. for 2 h. A solution of 16.0 g (0.056 mol) of N-tert-butyl-5-amino-2-methoxycarbonylbenzenesulfonamide in 50 ml of DMF is then added dropwise at 0° C. The cooling bath is removed and the mixt... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | CN(C)C=O | null | 4 | COC(=O)c1ccc(N)cc1S(=O)(=O)NC(C)(C)C.O=CO>CN(C)C=O>COC(=O)c1ccc(NC=O)cc1S(=O)(=O)NC(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-eb3a2bf3a97a4cecad374cf323a11215 | CCOC(=O)N=C=S.CNc1ccc(C(=O)OC)c(S(=O)(=O)NC(C)(C)C)c1>>CCOC(=O)NC(=S)CNc1ccc(C(=O)OC)c(S(=O)(=O)NC(C)(C)C)c1 | C(C)(C)(C)NS(=O)(=O)C1=C(C=CC(=C1)NC)C(=O)OC.C(C)OC(=O)N=C=S>>C(C)(C)(C)NS(=O)(=O)C1=C(C=CC(=C1)NCC(=S)NC(=O)OCC)C(=O)OC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]=[C:7]=[S:8].[CH3:9][NH:10][c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[O:17][CH3:18])[c:19]([S:20](=[O:21])(=[O:22])[NH:23][C:24]([CH3:25])([CH3:26])[CH3:27])[cH:28]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[NH:6][C:7](=[S:8])[CH2:9][NH:10][c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[O:17][... | CCOC(=O)N=C=S.CNc1ccc(C(=O)OC)c(S(=O)(=O)NC(C)(C)C)c1 | CCOC(=O)NC(=S)CNc1ccc(C(=O)OC)c(S(=O)(=O)NC(C)(C)C)c1 | null | null | CN(C)C=O.C(C)(=O)OCC | C-C Coupling | OtherReaction | 77f749dee5e01076740357fb41b1def165a1f996dc0d6c5dbae7a109780d0d90 | c6cb240f0fa10e1154337af10c92dbfd08b8c3581f62a07cbcf771210af2f1af | c1ccccc1 | [CH3;D1;+0:1]-[#7:2]-[c:3].[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[N;H0;D2;+0:8]=[C;H0;D2;+0:9]=[S;D1;H0:10]>>[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[NH;D2;+0:8]-[C;H0;D3;+0:9](=[S;D1;H0:10])-[CH2;D2;+0:1]-[#7:2]-[c:3] | 75 | [{"value": 75.0, "product": "C(C)(C)(C)NS(=O)(=O)C1=C(C=CC(=C1)NCC(=S)NC(=O)OCC)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 1.20 g (4.0 mmol) of N-tert-butyl-2-methoxycarbonyl-5-methylaminobenzenesulfonamide is dissolved in 5 ml of anhydrous DMF, and 0.60 g (4.3 mmol) of 95% strength ethoxycarbonyl isothiocyanate is added. After 3 h at room temperature the mixture is taken up in ethyl acetate and washed with 1N hydrochloric acid and water. ... | 10.6084/m9.figshare.5104873.v1 | null | Isothiocyanate | Carbamic ester.Thioamide | null | null | c1ccccc1 | null | CN(C)C=O.C(C)(=O)OCC | null | null | CCOC(=O)N=C=S.CNc1ccc(C(=O)OC)c(S(=O)(=O)NC(C)(C)C)c1>CN(C)C=O.C(C)(=O)OCC>CCOC(=O)NC(=S)CNc1ccc(C(=O)OC)c(S(=O)(=O)NC(C)(C)C)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5d39e4809233431997c0a9624f5079c5 | COc1c(Cl)ccnc1C.NOCc1ccccc1>>COc1c(NOCc2ccccc2)ccnc1C | ClC1=C(C(=NC=C1)C)OC.C1(=CC=CC=C1)O.C(C1=CC=CC=C1)ON.[OH-].[Na+]>>C(C1=CC=CC=C1)ONC1=C(C(=NC=C1)C)OC | Cl[c:4]1[c:3]([O:2][CH3:1])[c:17]([CH3:18])[n:16][cH:15][cH:14]1.[NH2:5][O:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[CH3:1][O:2][c:3]1[c:4]([NH:5][O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15][n:16][c:17]1[CH3:18] | COc1c(Cl)ccnc1C.NOCc1ccccc1 | COc1c(NOCc2ccccc2)ccnc1C | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CONc2ccncc2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[C;D1;H3:6]):[c:7]:1-[#8:8].[C:9]-[#8:10]-[NH2;D1;+0:11]>>[#8:8]-[c:7]1:[c:5](-[C;D1;H3:6]):[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:11]-[#8:10]-[C:9] | null | [] | null | null | null | null | 16 g of 4-chloro-3-methoxy-2-methylpyridine, 63 g of phenol and 40 g of O-benzylhydroxylamine are stirred at 120° C. under nitrogen for 4 hours. After cooling, the mixture is shaken with 500 ml of 2N NaOH and CH2Cl2. The aqueous phase is extracted a second time with CH2Cl2. After concentrating the combined CH2Cl2 phase... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | HCl | C(Cl)Cl | null | null | COc1c(Cl)ccnc1C.NOCc1ccccc1>C(Cl)Cl>COc1c(NOCc2ccccc2)ccnc1C |
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