dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-761d9ebecdbe44d99dedfd4f28298023 | C=C(C(=O)OCC)C(C)c1ccc(NC(=O)OC(C)(C)C)nc1.CC(O)=S>>CCOC(=O)C(CSC(C)=O)C(C)c1ccc(NC(=O)OC(C)(C)C)nc1 | C(C)OC(C(=C)C(C)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O.C(C)(=S)O.CCOC(=O)C>>C(C)OC(C(C(C)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)CSC(C)=O)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH2:7])[CH:12]([CH3:13])[c:14]1[cH:15][cH:16][c:17]([NH:18][C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[n:26][cH:27]1.[S:8]=[C:9]([CH3:10])[OH:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][S:8][C:9]([CH3:10])=[O:11])[CH:12]([CH3:13])[c:14]1[cH:15][cH:16][c:17]([... | C=C(C(=O)OCC)C(C)c1ccc(NC(=O)OC(C)(C)C)nc1.CC(O)=S | CCOC(=O)C(CSC(C)=O)C(C)c1ccc(NC(=O)OC(C)(C)C)nc1 | null | null | null | Protection | OtherReaction | 56aa090d67fbecbea8a1963579cc34949775a09653b2b2f2795c609c60e70c77 | 5a9b0d631147b21b844b3c73866d1d81ab543538a176ebae28118ae7e39e572f | c1ccncc1 | [#7;a:1]:[c:2]:[c:3]-[C:4](-[C;D1;H3:5])-[C;H0;D3;+0:6](=[CH2;D1;+0:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11].[C;D1;H3:12]-[C;H0;D3;+0:13](-[OH;D1;+0:14])=[S;H0;D1;+0:15]>>[#7;a:1]:[c:2]:[c:3]-[C:4](-[C;D1;H3:5])-[CH;D3;+0:6](-[CH2;D2;+0:7]-[S;H0;D2;+0:15]-[C;H0;D3;+0:13](-[C;D1;H3:12])=[O;H0;D1;+0:14])-[C:8](=[O;D1;H0:9]... | 91 | [{"value": 91.0, "product": "C(C)OC(C(C(C)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)CSC(C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | 45 | CELSIUS | null | null | TEA (0.076 mL, 0.542 mmol) was added to a solution of 2-[1-(6-tert-butoxycarbonylamino-pyridin-3-yl)-ethyl]-acrylic acid ethyl ester (158 mg, 0.493 mmol) in thioacetic acid (2 mL) at 0° C. under argon. The mixture was stirred at 45° C. over night. EtOAc was added and the solution was washed with NaHCO3 and brine, dried... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Thiocarbonyl.Vinyl | Ester.Carbo-thioester | null | null | c1ccncc1 | null | null | 45 | null | C=C(C(=O)OCC)C(C)c1ccc(NC(=O)OC(C)(C)C)nc1.CC(O)=S>>CCOC(=O)C(CSC(C)=O)C(C)c1ccc(NC(=O)OC(C)(C)C)nc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8ce85ab6ceb94c2baed95550c8ddf14d | CCOC(=O)C(CSC(C)=O)C(C)c1ccc(NC(=O)OC(C)(C)C)nc1>>CCOC(=O)C(CSC(C)=O)C(C)c1ccc(N)nc1 | C(=O)(C(F)(F)F)O.C(C)OC(C(C(C)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)CSC(C)=O)=O>>C(C)OC(C(C(C)C=1C=NC(=CC1)N)CSC(C)=O)=O | CC(C)(C)OC(=O)[NH:18][c:17]1[cH:16][cH:15][c:14]([CH:12]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][S:8][C:9]([CH3:10])=[O:11])[CH3:13])[cH:20][n:19]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][S:8][C:9]([CH3:10])=[O:11])[CH:12]([CH3:13])[c:14]1[cH:15][cH:16][c:17]([NH2:18])[n:19][cH:20]1 | CCOC(=O)C(CSC(C)=O)C(C)c1ccc(NC(=O)OC(C)(C)C)nc1 | CCOC(=O)C(CSC(C)=O)C(C)c1ccc(N)nc1 | null | null | C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccncc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | 132.3 | [{"value": 95.0, "product": "C(C)OC(C(C(C)C=1C=NC(=CC1)N)CSC(C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 132.3, "product": "C(C)OC(C(C(C)C=1C=NC(=CC1)N)CSC(C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 60 | MINUTE | TFA (2 mL) was added to a solution of 2-acetylsulfanylmethyl-3-(6-tert-butoxycarbonylamino-pyridin-3-yl)-butyric acid ethyl ester (178 mg, 0.449 mmol) in methylene chloride (2 mL). The mixture was stirred for 60 min and concentrated under reduced pressure. Flash chromatography (toluene/EtOAc, 1:6) gave unpure 2-acetyls... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccncc1 | HO- | C(Cl)Cl | null | 1 | CCOC(=O)C(CSC(C)=O)C(C)c1ccc(NC(=O)OC(C)(C)C)nc1>C(Cl)Cl>CCOC(=O)C(CSC(C)=O)C(C)c1ccc(N)nc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-508daf97ba984034880e115a2676fc9f | CCOC(=O)C(CSC(C)=O)C(C)c1ccc(N)nc1>>CC(c1ccc(N)nc1)C(CS)C(=O)O | Cl.C(C)OC(C(C(C)C=1C=NC(=CC1)N)CSC(C)=O)=O>>NC1=CC=C(C=N1)C(C(C(=O)O)CS)C | CC[O:15][C:13]([CH:10]([CH:2]([CH3:1])[c:3]1[cH:4][cH:5][c:6]([NH2:7])[n:8][cH:9]1)[CH2:11][S:12]C(C)=O)=[O:14]>>[CH3:1][CH:2]([c:3]1[cH:4][cH:5][c:6]([NH2:7])[n:8][cH:9]1)[CH:10]([CH2:11][SH:12])[C:13](=[O:14])[OH:15] | CCOC(=O)C(CSC(C)=O)C(C)c1ccc(N)nc1 | CC(c1ccc(N)nc1)C(CS)C(=O)O | null | null | null | Reduction | OtherReaction | 1bcd8cbb2f136b4bcba1690e9ba45c4e43c89ba76f0e22de82a7d3fe318c82a9 | 5654c46fe4cb226f88ec3c899c7f9be1825c357673ea686958f9ef4883ee1db3 | c1ccncc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[S;H0;D2;+0:6]-C(-C)=O>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[C:4]-[C:5]-[SH;D1;+0:6] | 106.5 | [{"value": 92.0, "product": "NC1=CC=C(C=N1)C(C(C(=O)O)CS)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 106.5, "product": "NC1=CC=C(C=N1)C(C(C(=O)O)CS)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Conc. hydrochloric acid (4 mL) was added to 2-acetylsulfanylmethyl-3-(6amino-pyridin-3-yl)-butyric acid ethyl ester (104 mg, 0.253 mmol) under argon. The reaction was heated to reflux for 5 h and then concentrated under reduced pressure to give a diastereomeric mixture of the title compound (61 mg, 92%) as the hydrochl... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Carbo-thioester | Carboxylic acid.Aliphatic thiol | null | null | c1ccncc1 | HO- | null | null | null | CCOC(=O)C(CSC(C)=O)C(C)c1ccc(N)nc1>>CC(c1ccc(N)nc1)C(CS)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-184708061ceb4f5cb122024729392cba | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH2]O[Si](C)(C)C(C)(C)C.Cc1nc(NC(=O)OC(C)(C)C)ccc1Br>>Cc1nc(NC(=O)OC(C)(C)C)ccc1C(C)(C)O[SiH2]C(C)(C)C | [F-].[K+].C(C)(C)(C)OC(NC1=NC(=C(C=C1)Br)C)=O.C(C)(C)(C)[Si](OC[Sn](CCCC)(CCCC)CCCC)(C)C.ClCCCl.C(C)OCC>>C(C)(C)(C)OC(NC1=NC(=C(C=C1)C(O[SiH2]C(C)(C)C)(C)C)C)=O | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH2:16][O:19][Si:20]([CH3:17])([CH3:18])[C:21]([CH3:22])([CH3:23])[CH3:24].Br[c:15]1[c:2]([CH3:1])[n:3][c:4]([NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[cH:13][cH:14]1>>[CH3:1][c:2]1[n:3][c:4]([NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[cH:13][cH:14][c:15]1... | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH2]O[Si](C)(C)C(C)(C)C.Cc1nc(NC(=O)OC(C)(C)C)ccc1Br | Cc1nc(NC(=O)OC(C)(C)C)ccc1C(C)(C)O[SiH2]C(C)(C)C | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | null | C-C Coupling | OtherReaction | 2c35ffcca42587548be5417494593198fc16ef4537fcb3507e56ecb0940f483d | e19d215278fe89455f513eea1f431a9cbd352fd26641180be69d9777a377b4b5 | c1ccncc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[C;D1;H3:7].C-C-C-[CH2]-[Sn](-[CH2;D2;+0:8]-[#8:9]-[Si;H0;D4;+0:10](-[CH3;D1;+0:11])(-[CH3;D1;+0:12])-[C:13](-[C;D1;H3:14])(-[C;D1;H3:15])-[C;D1;H3:16])(-[CH2]-C-C-C)-[CH2]-C-C-C>>[C;D1;H3:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[C;H0;D4;+0:8](-[CH3;D1... | 47 | [{"value": 47.0, "product": "C(C)(C)(C)OC(NC1=NC(=C(C=C1)C(O[SiH2]C(C)(C)C)(C)C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 60 | MINUTE | A solution of (5-bromo-6-methyl-pyridin-2-yl)-carbamic acid tert-butyl ester (27.5 g, 95.8 mmol), tert-butyl-dimethyl-tributylstannanylmethoxy-silane (43.5 g, 100.2 mmol), and bis(triphenylphosphine)palladium(II) dichloride (1.00 g, 1.40 mmol) in 1,2-dichloroethane (350 mL) was stirred at reflux for 48 h. Additional bi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.TMS ether protective group.Tin | null | c1ccncc1 | c1ccncc1 | c1ccncc1 | HBr.Sn | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | 0 | 1 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH2]O[Si](C)(C)C(C)(C)C.Cc1nc(NC(=O)OC(C)(C)C)ccc1Br>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl>Cc1nc(NC(=O)OC(C)(C)C)ccc1C(C)(C)O[SiH2]C(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1373f99ac6324b0db02b48761b5136e7 | Cc1nc(NC(=O)OC(C)(C)C)ccc1C(C)(C)O[SiH2]C(C)(C)C>>Cc1nc(NC(=O)OC(C)(C)C)ccc1CO | [F-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(C)(C)OC(NC1=NC(=C(C=C1)C(O[SiH2]C(C)(C)C)(C)C)C)=O.O>>C(C)(C)(C)OC(NC1=NC(=C(C=C1)CO)C)=O | CC(C)(C)[SiH2][O:17][C:16](C)(C)[c:15]1[c:2]([CH3:1])[n:3][c:4]([NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[cH:13][cH:14]1>>[CH3:1][c:2]1[n:3][c:4]([NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[cH:13][cH:14][c:15]1[CH2:16][OH:17] | Cc1nc(NC(=O)OC(C)(C)C)ccc1C(C)(C)O[SiH2]C(C)(C)C | Cc1nc(NC(=O)OC(C)(C)C)ccc1CO | null | null | C1CCOC1 | Deprotection | OtherReaction | d7487e9652d81f9226fa8fb90bf02725deb1441d4abc97ee4fdbe439e00122e0 | ff9889ffd40f59bd281424811967f384d29acb01a2d54e10590c5a677f81d17a | c1ccncc1 | C-C(-C)(-C)-[SiH2]-[O;H0;D2;+0:1]-[C;H0;D4;+0:2](-C)(-C)-[c:3](:[c:4]):[c:5](-[C;D1;H3:6]):[#7;a:7]:[c:8]>>[C;D1;H3:6]-[c:5](:[#7;a:7]:[c:8]):[c:3](-[CH2;D2;+0:2]-[OH;D1;+0:1]):[c:4] | 81 | [{"value": 81.0, "product": "C(C)(C)(C)OC(NC1=NC(=C(C=C1)CO)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.6, "product": "C(C)(C)(C)OC(NC1=NC(=C(C=C1)CO)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Tetrabutylammonium fluoride (19.6 g, 62.4 mmol) was added to a solution of [5-(tert-butyl-dimethyl-silanyloxymethyl)-6-methyl-pyridin-2-yl]-carbamic acid tert-butyl ester (10.5 g, 31.23 mmol) in THF (100 mL) and stirred at room temperature overnight. Water was added and the product extracted with chloroform. The organi... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary alcohol | null | null | c1ccncc1 | Other | C1CCOC1 | null | 8 | Cc1nc(NC(=O)OC(C)(C)C)ccc1C(C)(C)O[SiH2]C(C)(C)C>C1CCOC1>Cc1nc(NC(=O)OC(C)(C)C)ccc1CO |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e3f6a6dfc7f54f738769feb1bbdfdd3b | CCOC(=O)CC(=O)OCC.Cc1nc(NC(=O)OC(C)(C)C)ccc1CBr>>CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1C)C(=O)OCC | CCOC(=O)C.C(CC(=O)OCC)(=O)OCC.[H-].[Na+].C(C)(C)(C)OC(NC1=NC(=C(C=C1)CBr)C)=O>>C(C)OC(C(C(=O)OCC)CC=1C(=NC(=CC1)NC(=O)OC(C)(C)C)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:23](=[O:24])[O:25][CH2:26][CH3:27].Br[CH2:7][c:8]1[cH:9][cH:10][c:11]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[n:20][c:21]1[CH3:22]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][cH:10][c:11]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:... | CCOC(=O)CC(=O)OCC.Cc1nc(NC(=O)OC(C)(C)C)ccc1CBr | CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1C)C(=O)OCC | null | null | CN(C)C=O | C-C Coupling | OtherReaction | 8175b6573d6439ec7ccc45bf6b48843ab56b46dccfc6504384c4766d09f35cc7 | d1817e44576d3a158547867a56245217a593d4f828a6d6dfaa8ed11276894e44 | c1ccncc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4](-[C;D1;H3:5]):[#7;a:6]:[c:7].[C:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[CH2;D2;+0:12]-[C:13](=[O;D1;H0:14])-[#8:15]-[C:16]>>[C:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[CH;D3;+0:12](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4](-[C;D1;H3:5]):[#7;a:6]:[c:7])-[C:13](=[O;D1;H0:14])-[#8:15]-[C:16] | 74 | [{"value": 74.0, "product": "C(C)OC(C(C(=O)OCC)CC=1C(=NC(=CC1)NC(=O)OC(C)(C)C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.0, "product": "C(C)OC(C(C(=O)OCC)CC=1C(=NC(=CC1)NC(=O)OC(C)(C)C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 45 | MINUTE | A solution of diethyl malonate (1.21 mL, 7.97 mmol) in DMF (2 mL) was added dropwise to a suspention of NaH (348 mg, 7.97 mmol, 55% in mineral oil) in DMF (5 mL) at 0 ° C. under argon. The reaction mixture was stirred for 45 min and a solution of (5-bromomethyl-6-methyl-pyridin-2-yl)-carbamic acid tert-butyl ester (2.0... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ester | Ester.Ester | null | null | c1ccncc1 | HBr | CN(C)C=O | null | 0.75 | CCOC(=O)CC(=O)OCC.Cc1nc(NC(=O)OC(C)(C)C)ccc1CBr>CN(C)C=O>CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1C)C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-21fad67156264e4480b30ec1c771b74e | CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1C)C(=O)OCC>>CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1C)C(=O)O | [OH-].[K+].C(C)OC(C(C(=O)OCC)CC=1C(=NC(=CC1)NC(=O)OC(C)(C)C)C)=O.CCOC(=O)C>>C(C)OC(C(C(=O)O)CC=1C(=NC(=CC1)NC(=O)OC(C)(C)C)C)=O | CC[O:25][C:23]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][c:8]1[cH:9][cH:10][c:11]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[n:20][c:21]1[CH3:22])=[O:24]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][cH:10][c:11]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[n:... | CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1C)C(=O)OCC | CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1C)C(=O)O | null | null | CCO.CCO.C(Cl)Cl | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccncc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7]>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 84.7 | [{"value": 84.7, "product": "C(C)OC(C(C(=O)O)CC=1C(=NC(=CC1)NC(=O)OC(C)(C)C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 40 | HOUR | A solution of KOH (300 mg, 5.35 mmol) in EtOH (4 mL) was added to a solution of 2-(6-tert-butoxycarbonylamino-2-methyl-pyridin-3-ylmethyl)-malonic acid diethyl ester (1.85 g, 4.86 mmol) in EtOH/methylene chloride (2:1, 21 mL) at 0° C. The mixture was stirred for 40 h at room temperature and EtOAc was added. The mixture... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccncc1 | Other | CCO.CCO.C(Cl)Cl | null | 40 | CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1C)C(=O)OCC>CCO.CCO.C(Cl)Cl>CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1C)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-25f326f9f0f54f25b93e2ee1d2fd505f | CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1C)C(=O)O>>C=C(Cc1ccc(NC(=O)OC(C)(C)C)nc1C)C(=O)OCC | C(C)NCC.C(C)OC(C(C(=O)O)CC=1C(=NC(=CC1)NC(=O)OC(C)(C)C)C)=O.C=O>>C(C)OC(C(=C)CC=1C(=NC(=CC1)NC(=O)OC(C)(C)C)C)=O | O=[C:1](O)[CH:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([NH:8][C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[n:16][c:17]1[CH3:18])[C:19](=[O:20])[O:21][CH2:22][CH3:23]>>[CH2:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([NH:8][C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[n:16][c:17]1[CH3:18])[C:19](=[O:20])[O:21][... | CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1C)C(=O)O | C=C(Cc1ccc(NC(=O)OC(C)(C)C)nc1C)C(=O)OCC | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 485594ce7bba157615ffbb01ccede84a4e638576571b5d04649a06f3d4b7bce0 | 55e5b5078322f9f4fb0a7e9b5fc8a8cb9084e9135b447b8c441ad0800765792e | c1ccncc1 | O-[C;H0;D3;+0:1](=O)-[CH;D3;+0:2](-[C:3]-[c:4]:[c:5]:[#7;a:6])-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10]>>[#7;a:6]:[c:5]:[c:4]-[C:3]-[C;H0;D3;+0:2](=[CH2;D1;+0:1])-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10] | 79 | [{"value": 79.0, "product": "C(C)OC(C(=C)CC=1C(=NC(=CC1)NC(=O)OC(C)(C)C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.6, "product": "C(C)OC(C(=C)CC=1C(=NC(=CC1)NC(=O)OC(C)(C)C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Diethylamine (359 mg, 4.90 mmol) was added dropwise to a solution of 2-(6-tert-butoxycarbonylamino-2-methyl-pyridin-3-ylmethyl)-malonic acid monoethyl ester (1.44 g, 4.09 mmol) and formaldehyde (464 mg, 5.72 mmol, 37% in water) in methylene chloride (35 mL) at 0° C. under argon. The mixture was stirred at room temperat... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester | Ester.Vinyl | null | null | c1ccncc1 | Other | C(Cl)Cl | null | null | CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1C)C(=O)O>C(Cl)Cl>C=C(Cc1ccc(NC(=O)OC(C)(C)C)nc1C)C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8d5d0fa9d6d04d2bbd3af2e94c61d5df | C=C(Cc1ccc(NC(=O)OC(C)(C)C)nc1C)C(=O)OCC.CC(O)=S>>CCOC(=O)C(CSC(C)=O)Cc1ccc(NC(=O)OC(C)(C)C)nc1C | C(C)OC(C(=C)CC=1C(=NC(=CC1)NC(=O)OC(C)(C)C)C)=O.C(C)(=S)O.CCOC(=O)C>>C(C)OC(C(CC=1C(=NC(=CC1)NC(=O)OC(C)(C)C)C)CSC(C)=O)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH2:7])[CH2:12][c:13]1[cH:14][cH:15][c:16]([NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[n:25][c:26]1[CH3:27].[S:8]=[C:9]([CH3:10])[OH:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][S:8][C:9]([CH3:10])=[O:11])[CH2:12][c:13]1[cH:14][cH:15][c:16]([NH:17][C:18... | C=C(Cc1ccc(NC(=O)OC(C)(C)C)nc1C)C(=O)OCC.CC(O)=S | CCOC(=O)C(CSC(C)=O)Cc1ccc(NC(=O)OC(C)(C)C)nc1C | null | null | null | Protection | OtherReaction | 56aa090d67fbecbea8a1963579cc34949775a09653b2b2f2795c609c60e70c77 | 5a9b0d631147b21b844b3c73866d1d81ab543538a176ebae28118ae7e39e572f | c1ccncc1 | [#7;a:1]:[c:2]:[c:3]-[C:4]-[C;H0;D3;+0:5](=[CH2;D1;+0:6])-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10].[C;D1;H3:11]-[C;H0;D3;+0:12](-[OH;D1;+0:13])=[S;H0;D1;+0:14]>>[#7;a:1]:[c:2]:[c:3]-[C:4]-[CH;D3;+0:5](-[CH2;D2;+0:6]-[S;H0;D2;+0:14]-[C;H0;D3;+0:12](-[C;D1;H3:11])=[O;H0;D1;+0:13])-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10] | 87 | [{"value": 87.0, "product": "C(C)OC(C(CC=1C(=NC(=CC1)NC(=O)OC(C)(C)C)C)CSC(C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 64 | HOUR | TEA (0.556 mL, 3.99 mmol) was added to a solution of 2-(6-tert-butoxycarbonylamino-2-methyl-pyridin-3-ylmethyl)-acrylic acid ethyl ester (1.23 g, 3.84 mmol) in thioacetic acid (10 mL) at 0 ° C. under argon. The mixture was stirred at room temperature for 64 h. EtOAc was added and the solution was washed with Na2CO3 and... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Thiocarbonyl.Vinyl | Ester.Carbo-thioester | null | null | c1ccncc1 | null | null | null | 64 | C=C(Cc1ccc(NC(=O)OC(C)(C)C)nc1C)C(=O)OCC.CC(O)=S>>CCOC(=O)C(CSC(C)=O)Cc1ccc(NC(=O)OC(C)(C)C)nc1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7f2064fa514840978f43fd93a89abf39 | CCOC(=O)C(CSC(C)=O)Cc1ccc(NC(=O)OC(C)(C)C)nc1C>>Cc1nc(N)ccc1CC(CS)C(=O)O | Cl.C(C)OC(C(CC=1C(=NC(=CC1)NC(=O)OC(C)(C)C)C)CSC(C)=O)=O>>NC1=CC=C(C(=N1)C)CC(C(=O)O)CS | CC[O:15][C:13]([CH:10]([CH2:9][c:8]1[c:2]([CH3:1])[n:3][c:4]([NH:5]C(=O)OC(C)(C)C)[cH:6][cH:7]1)[CH2:11][S:12]C(C)=O)=[O:14]>>[CH3:1][c:2]1[n:3][c:4]([NH2:5])[cH:6][cH:7][c:8]1[CH2:9][CH:10]([CH2:11][SH:12])[C:13](=[O:14])[OH:15] | CCOC(=O)C(CSC(C)=O)Cc1ccc(NC(=O)OC(C)(C)C)nc1C | Cc1nc(N)ccc1CC(CS)C(=O)O | null | null | null | Reduction | OtherReaction | df63f36502c6e187beb1211487c3f0937031934a12a3c506c12c51a17b700a31 | 9a7c4efef36aa8beb2b85c58cd3924b350f3ef529d4eb0778d927167159d9d8b | c1ccncc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].C-C-[O;H0;D2;+0:6]-[C:7](=[O;D1;H0:8])-[C:9]-[C:10]-[S;H0;D2;+0:11]-C(-C)=O>>[NH2;D1;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:8]=[C:7](-[OH;D1;+0:6])-[C:9]-[C:10]-[SH;D1;+0:11] | 90.7 | [{"value": 76.0, "product": "NC1=CC=C(C(=N1)C)CC(C(=O)O)CS", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.7, "product": "NC1=CC=C(C(=N1)C)CC(C(=O)O)CS", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Conc. hydrochloric acid (2 mL) was added to 2-acetylsulfanylmethyl-3-(6-tert-butoxycarbonylamino-2-methyl-pyridin-3-yl)-propionic acid ethyl ester (77 mg, 0.19 mmol) under argon. The reaction was heated to reflux for 110 min and was then concentrated under reduced pressure to give the title compound (39 mg, 76%) as the... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ether.Carbo-thioester.Boc | Carboxylic acid.Primary amine.Aliphatic thiol | null | null | c1ccncc1 | HO- | null | null | null | CCOC(=O)C(CSC(C)=O)Cc1ccc(NC(=O)OC(C)(C)C)nc1C>>Cc1nc(N)ccc1CC(CS)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-867b195600854178ac824c7615cb1d97 | CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1ncc(Br)cn1.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH2]O[Si](C)(C)C(C)(C)C>>CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1ncc(C(C)(C)O[SiH2]C(C)(C)C)cn1 | [F-].[K+].C(C)(C)(C)OC(=O)N(C(=O)OC(C)(C)C)C1=NC=C(C=N1)Br.C(C)(C)(C)[Si](OC[Sn](CCCC)(CCCC)CCCC)(C)C.ClCCCl.C(C)OCC>>C(C)(C)(C)OC(=O)N(C(=O)OC(C)(C)C)C1=NC=C(C=N1)C(O[SiH2]C(C)(C)C)(C)C | Br[c:19]1[cH:18][n:17][c:16]([N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[n:30][cH:29]1.CCC[CH2][Sn]([CH2]CCC)([CH2:20][O:23][Si:24](C)(C)[C:25]([CH3:26])([CH3:27])[CH3:28])[CH2:22]CC[CH3:21]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]([C:9](=... | CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1ncc(Br)cn1.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH2]O[Si](C)(C)C(C)(C)C | CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1ncc(C(C)(C)O[SiH2]C(C)(C)C)cn1 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | null | C-C Coupling | OtherReaction | f4ae20f7f31943c020c8b8a142c387b44fa349e87d534ca879e5f8eefda0c9b1 | e19d215278fe89455f513eea1f431a9cbd352fd26641180be69d9777a377b4b5 | c1cncnc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1.C-C-C-[CH2]-[Sn](-[CH2;D2;+0:7]-[#8:8]-[Si;H0;D4;+0:9](-C)(-C)-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[C;D1;H3:13])(-[CH2;D2;+0:14]-C-C-[CH3;D1;+0:15])-[CH2]-C-C-C>>[C;D1;H3:11]-[C:10](-[C;D1;H3:12])(-[C;D1;H3:13])-[SiH2;D2;+0:9]-[#8:8]-[C;H0;D4;+0:7](-[CH3;D1;+0:1... | 55 | [{"value": 55.0, "product": "C(C)(C)(C)OC(=O)N(C(=O)OC(C)(C)C)C1=NC=C(C=N1)C(O[SiH2]C(C)(C)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 60 | MINUTE | A solution of 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-bromopyrimidin (16.0 g, 45.0 mmol), tert-butyl-dimethyl-tributylstannanylmethoxy-silane (20.5 g, 47.1 mmol), and bis(triphenylphosphine)palladium(II) dichloride (1.00 g, 1.40 mmol) in 1,2-dichloroethane (50 mL) was stirred at reflux overnight. Additional bis(triphen... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.TMS ether protective group.Tin | null | c1cncnc1 | c1cncnc1 | c1cncnc1 | HBr.Sn | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | 0 | 1 | CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1ncc(Br)cn1.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH2]O[Si](C)(C)C(C)(C)C>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl>CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1... |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-47147d4078fc4d00bf7261458a1d1430 | CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1ncc(C(C)(C)O[SiH2]C(C)(C)C)cn1>>CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1ncc(CO)cn1 | [F-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(C)(C)OC(=O)N(C(=O)OC(C)(C)C)C1=NC=C(C=N1)C(O[SiH2]C(C)(C)C)(C)C.O>>C(C)(C)(C)OC(=O)N(C(=O)OC(C)(C)C)C1=NC=C(C=N1)CO | CC(C)(C)[SiH2][O:21][C:20](C)(C)[c:19]1[cH:18][n:17][c:16]([N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[n:23][cH:22]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[c:16]1[n:17][cH:18][c:19]... | CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1ncc(C(C)(C)O[SiH2]C(C)(C)C)cn1 | CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1ncc(CO)cn1 | null | null | C1CCOC1 | Deprotection | OtherReaction | d7487e9652d81f9226fa8fb90bf02725deb1441d4abc97ee4fdbe439e00122e0 | ff9889ffd40f59bd281424811967f384d29acb01a2d54e10590c5a677f81d17a | c1cncnc1 | C-C(-C)(-C)-[SiH2]-[O;H0;D2;+0:1]-[C;H0;D4;+0:2](-C)(-C)-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:1>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:1 | 53.1 | [{"value": 53.0, "product": "C(C)(C)(C)OC(=O)N(C(=O)OC(C)(C)C)C1=NC=C(C=N1)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.1, "product": "C(C)(C)(C)OC(=O)N(C(=O)OC(C)(C)C)C1=NC=C(C=N1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Tetrabutylammonium fluoride (15.3 g, 48.6 mmol) was added to a solution of 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-(ter-butyl-dimethyl-silanyloxymethyl)-pyrimidin (10.0 g, 24.3 mmol) in THF (100 mL) and stirred at room temperature overnight. Water was added and the product extracted with chloroform. The organic phase w... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary alcohol | null | null | c1cncnc1 | Other | C1CCOC1 | null | 8 | CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1ncc(C(C)(C)O[SiH2]C(C)(C)C)cn1>C1CCOC1>CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1ncc(CO)cn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0b1f95d04a7e45cc9e1fbc6ff7510f68 | BrC(Br)(Br)Br.CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1ncc(CO)cn1>>CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1ncc(CBr)cn1 | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(Br)(Br)(Br)Br.C(C)(C)(C)OC(=O)N(C(=O)OC(C)(C)C)C1=NC=C(C=N1)CO>>BrCC=1C=NC(=NC1)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C | BrC(Br)(Br)[Br:21].O[CH2:20][c:19]1[cH:18][n:17][c:16]([N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[n:23][cH:22]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[c:16]1[n:17][cH:18][c:19]([CH... | BrC(Br)(Br)Br.CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1ncc(CO)cn1 | CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1ncc(CBr)cn1 | null | null | ClCCl | Functional Group Interconversion | Appel reaction | 752e1807cd47d8316010cc3f92eab16c5a89ffb844d9514fcae469ba993c78dd | 2c6b51fb1e17cb2c93d565e0423c75825df2c8e11c870e0c98b278f20ba9f3ad | c1cncnc1 | Br-C(-Br)(-Br)-[Br;H0;D1;+0:1].O-[CH2;D2;+0:2]-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:1>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:1 | 67 | [{"value": 67.0, "product": "BrCC=1C=NC(=NC1)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.8, "product": "BrCC=1C=NC(=NC1)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Triphenylphosphine (2.71 g, 10.73 mmol) and CBr4 (4.89 g, 14.8 mmol) was added to a solution of 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-hydroxymethyl-pyrimidin (3.20 g, 9.83 mmol) in dichloromethane (30 mL) at 0° C. The reaction mixture was stirred for 1 h and was then diluted with dichloromethane. The organic phase wa... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Primary alcohol | Primary halide | null | null | c1cncnc1 | HBr | ClCCl | null | 1 | BrC(Br)(Br)Br.CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1ncc(CO)cn1>ClCCl>CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1ncc(CBr)cn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dd952a3f8bce4f40af135ac1dd2040e3 | CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1ncc(CBr)cn1.CCOC(=O)CC(=O)OCC>>CCOC(=O)C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)nc1)C(=O)OCC | CCOC(=O)C.C(CC(=O)OCC)(=O)OCC.[H-].[Na+].BrCC=1C=NC(=NC1)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C>>C(C)OC(C(C(=O)OCC)CC=1C=NC(=NC1)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=O | Br[CH2:7][c:8]1[cH:9][n:10][c:11]([N:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[n:27][cH:28]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:29](=[O:30])[O:31][CH2:32][CH3:33]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][n:10][c:11]([N:... | CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1ncc(CBr)cn1.CCOC(=O)CC(=O)OCC | CCOC(=O)C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)nc1)C(=O)OCC | null | null | CN(C)C=O | C-C Coupling | OtherReaction | 8175b6573d6439ec7ccc45bf6b48843ab56b46dccfc6504384c4766d09f35cc7 | d1817e44576d3a158547867a56245217a593d4f828a6d6dfaa8ed11276894e44 | c1cncnc1 | Br-[CH2;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1.[C:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[CH2;D2;+0:12]-[C:13](=[O;D1;H0:14])-[#8:15]-[C:16]>>[C:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[CH;D3;+0:12](-[CH2;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1)-[C:13](=[O;D1;H0:14])-[#8:15]-[C:16] | 48.2 | [{"value": 40.0, "product": "C(C)OC(C(C(=O)OCC)CC=1C=NC(=NC1)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.2, "product": "C(C)OC(C(C(=O)OCC)CC=1C=NC(=NC1)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of diethyl malonate (0.704 mL, 4.64 mmol) in DMF (2 mL) was added dropwise to a suspention of NaH (200 mg, 4.64 mmol, 55% in mineral oil) in DMF (4 mL) at 0° C. under argon. The reaction mixture was stirred for 30 min and a solution of 5-bromomethyl-2-[N,N-bis(tert-butoxycarbonyl)amino]-pyrimidin (1.5 g, 3.8... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ester | Ester.Ester | null | null | c1cncnc1 | HBr | CN(C)C=O | null | 0.5 | CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1ncc(CBr)cn1.CCOC(=O)CC(=O)OCC>CN(C)C=O>CCOC(=O)C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)nc1)C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c0c425d244d24d478567e99075cddbd0 | CCOC(=O)C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)nc1)C(=O)OCC>>CCOC(=O)C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)nc1)C(=O)O | [OH-].[K+].C(C)OC(C(C(=O)OCC)CC=1C=NC(=NC1)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=O.CCOC(=O)C>>C(C)OC(C(C(=O)O)CC=1C=NC(=NC1)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=O | CC[O:31][C:29]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][c:8]1[cH:9][n:10][c:11]([N:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[n:27][cH:28]1)=[O:30]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][n:10][c:11]([N:12]([C:13](=[O:1... | CCOC(=O)C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)nc1)C(=O)OCC | CCOC(=O)C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)nc1)C(=O)O | null | null | CCO.CCO.C(Cl)Cl | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1cncnc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7]>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 89.2 | [{"value": 89.0, "product": "C(C)OC(C(C(=O)O)CC=1C=NC(=NC1)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.2, "product": "C(C)OC(C(C(=O)O)CC=1C=NC(=NC1)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A solution of KOH (106 mg, 1.88 mmol) in EtOH (2 mL) was added to a solution of 2-(2-[N,N-bis(tert-butoxycarbonyl)amino]-pyrimidin-5-ylmethyl)-malonic acid diethyl ester (0.80 g, 1.71 mmol) in EtOH/methylene chloride (2:1, 12 mL) at 0° C. The mixture was stirred for 16 h at room temperature and EtOAc was added. The mix... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cncnc1 | Other | CCO.CCO.C(Cl)Cl | null | 16 | CCOC(=O)C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)nc1)C(=O)OCC>CCO.CCO.C(Cl)Cl>CCOC(=O)C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)nc1)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b8f9fbfea5534b4395cf10443b1c8de1 | C=C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)nc1)C(=O)OCC.CC(O)=S>>CCOC(=O)C(CSC(C)=O)Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)nc1 | C(C)OC(C(=C)CC=1C=NC(=NC1)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=O.C(C)(=S)O.CCOC(=O)C>>C(C)OC(C(CC=1C=NC(=NC1)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)CSC(C)=O)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH2:7])[CH2:12][c:13]1[cH:14][n:15][c:16]([N:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[n:32][cH:33]1.[S:8]=[C:9]([CH3:10])[OH:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][S:8][C:9]([CH3:10])=[O:11])... | C=C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)nc1)C(=O)OCC.CC(O)=S | CCOC(=O)C(CSC(C)=O)Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)nc1 | null | null | null | Protection | OtherReaction | 56aa090d67fbecbea8a1963579cc34949775a09653b2b2f2795c609c60e70c77 | 5a9b0d631147b21b844b3c73866d1d81ab543538a176ebae28118ae7e39e572f | c1cncnc1 | [#7;a:1]:[c:2]:[c:3](-[C:4]-[C;H0;D3;+0:5](=[CH2;D1;+0:6])-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10]):[c:11]:[#7;a:12].[C;D1;H3:13]-[C;H0;D3;+0:14](-[OH;D1;+0:15])=[S;H0;D1;+0:16]>>[#7;a:1]:[c:2]:[c:3](-[C:4]-[CH;D3;+0:5](-[CH2;D2;+0:6]-[S;H0;D2;+0:16]-[C;H0;D3;+0:14](-[C;D1;H3:13])=[O;H0;D1;+0:15])-[C:7](=[O;D1;H0:8])-[#8:9]-... | 89 | [{"value": 89.0, "product": "C(C)OC(C(CC=1C=NC(=NC1)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)CSC(C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 40 | HOUR | TEA (0.189 mL, 1.35 mmol) was added to a solution of 2-(2-[N,N-bis(tert-butoxycarbonyl)amino]-pyrimidin-5-ylmethyl)-acrylic acid ethyl ester (0.53 g, 1.30 mmol) in thioacetic acid (13 mL) at 0° C. under argon. The mixture was stirred at room temperature for 40 h. EtOAc was added and the solution was washed with Na2CO3 ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Thiocarbonyl.Vinyl | Ester.Carbo-thioester | null | null | c1cncnc1 | null | null | null | 40 | C=C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)nc1)C(=O)OCC.CC(O)=S>>CCOC(=O)C(CSC(C)=O)Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)nc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2ddc12cb8a4744238f5c2c85ca990667 | CCOC(=O)C(CSC(C)=O)Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)nc1>>CCOC(=O)C(CSC(C)=O)Cc1cnc(N)nc1 | C(=O)(C(F)(F)F)O.C(C)OC(C(CC=1C=NC(=NC1)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)CSC(C)=O)=O>>C(C)OC(C(CC=1C=NC(=NC1)N)CSC(C)=O)=O | CC(C)(C)OC(=O)[N:17](C(=O)OC(C)(C)C)[c:16]1[n:15][cH:14][c:13]([CH2:12][CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][S:8][C:9]([CH3:10])=[O:11])[cH:19][n:18]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][S:8][C:9]([CH3:10])=[O:11])[CH2:12][c:13]1[cH:14][n:15][c:16]([NH2:17])[n:18][cH:19]1 | CCOC(=O)C(CSC(C)=O)Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)nc1 | CCOC(=O)C(CSC(C)=O)Cc1cnc(N)nc1 | null | null | C(Cl)Cl | Reduction | Boc amine deprotection | f552418eb10f74be275b3d2d2e4940118153e34a0e9e4737d38c7264f73cdda0 | c2e7125d1a630bb54d8f171aedbfa925f5104f1c1e5ac8c4ed9643a0c1117a44 | c1cncnc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-C(=O)-O-C(-C)(-C)-C)-[c:2](:[#7;a:3]:[c:4]):[#7;a:5]:[c:6]>>[NH2;D1;+0:1]-[c:2](:[#7;a:3]:[c:4]):[#7;a:5]:[c:6] | 132 | [{"value": 94.0, "product": "C(C)OC(C(CC=1C=NC(=NC1)N)CSC(C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 132.0, "product": "C(C)OC(C(CC=1C=NC(=NC1)N)CSC(C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 120 | MINUTE | TFA (1.5 mL) was added to a solution of 2-acetylsulfanylmethyl-3-(2-[N,N-bis(tert-butoxycarbonyl)amino]-pyrimidin-5-yl)-propionic acid ethyl ester (225 mg, 0.46 mmol) in methylene chloride (1.5 mL). The reaction was stirred for 120 min and concentrated under reduced pressure to give the title compound (172 mg, 94%) as ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carbamic ester.Ether.Ether.Substituted dicarboximide.Boc.Boc | Primary amine | null | null | c1cncnc1 | HO- | C(Cl)Cl | null | 2 | CCOC(=O)C(CSC(C)=O)Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)nc1>C(Cl)Cl>CCOC(=O)C(CSC(C)=O)Cc1cnc(N)nc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fb4ce0cb2e1f4a64b1bdf58712ab1ba0 | CC=O.CC=O.CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)P(=O)(OCC)OCC>>CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)=C(C)CC | C(C)=O.[H-].[Na+].C1CCOC1.C(C)OC(C(CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)P(=O)(OCC)OCC)=O.C1CCOC1.C(C)=O>>C(C)OC(C(=C(C)CC)CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O | O=[CH:22][CH3:23].O=[CH:24][CH3:25].CCOP(=O)(OCC)[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][c:8]1[cH:9][cH:10][c:11]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[n:20][cH:21]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH2:7][c:8]1[cH:9][cH:10][c:11]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH... | CC=O.CC=O.CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)P(=O)(OCC)OCC | CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)=C(C)CC | null | null | null | C-C Coupling | OtherReaction | df94ce1ef812a67a367bdb84db266633c98e393d86b9658f174c16eff14015ea | 7d1606afad2f949ac951f4d8ec08611f5e3954faae35cd16c1add454b504ba89 | c1ccncc1 | C-C-O-P(=O)(-O-C-C)-[CH;D3;+0:1](-[C:2]-[c:3]:[c:4]:[#7;a:5])-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9].O=[CH;D2;+0:10]-[C;D1;H3:11].O=[CH;D2;+0:12]-[C;D1;H3:13]>>[#7;a:5]:[c:4]:[c:3]-[C:2]-[C;H0;D3;+0:1](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9])=[C;H0;D3;+0:10](-[C;D1;H3:11])-[CH2;D2;+0:12]-[C;D1;H3:13] | null | [] | 0 | CELSIUS | 1 | HOUR | To a suspension of NaH (278.8 mg, 60% in mineral oil, 6.97 mmol) in THF (25 mL) at 0° C. was added a solution of 3-(6-tert-butoxycarbonylamino-pyridin-3-yl)-2-(diethoxyphosphoryl)-propionic acid ethyl ester (2.5 g, 5.81 mmol) in THF (30 mL). The reaction mixture was allowed to stir at 0° C. for 1 h. To the reaction was... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Aldehyde.Ester | Ester | null | null | c1ccncc1 | HO- | null | 0 | 1 | CC=O.CC=O.CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)P(=O)(OCC)OCC>>CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)=C(C)CC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-97eb620169274daea02aff9f956b1368 | CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)=C(C)CC.CCOC(C)=O.O=C(O)Cc1cccs1>>CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(C)SC(C)=O | CCOC(=O)C.S1C(=CC=C1)CC(=O)O.S1C(=CC=C1)CC(=O)O.CCN(CC)CC.C(C)OC(C(=C(C)CC)CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O>>C(C)OC(C(C(C)SC(C)=O)CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O | CC[C:22](=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][c:8]1[cH:9][cH:10][c:11]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[n:20][cH:21]1)[CH3:23].CCO[C:25]([CH3:26])=[O:27].O=C(O)Cc1ccc[s:24]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][cH:10][c:11]([NH:12][C:13](=[O:14])[O:15][C:... | CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)=C(C)CC.CCOC(C)=O.O=C(O)Cc1cccs1 | CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(C)SC(C)=O | null | null | null | Protection | OtherReaction | 0c0abf4652d4dbd5a5c68b3c2e5d171689993444c7f2a60ede2c010c6a967d81 | 1c4337c898896cd29d2e58565b619267363b5f6283f568e7e0adc001e55bd5ac | c1ccncc1 | C-C-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].C-C-[C;H0;D3;+0:4](-[C;D1;H3:5])=[C;H0;D3;+0:6](-[C:7]-[c:8]:[c:9]:[#7;a:10])-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14].O-C(=O)-C-c1:[s;H0;D2;+0:15]:c:c:c:1>>[#7;a:10]:[c:9]:[c:8]-[C:7]-[CH;D3;+0:6](-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14])-[CH;D3;+0:4](-[C;D1;H3:5])-[S;H0;D2;+0:1... | 68 | [{"value": 68.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To thiolacetic acid (15 mL) were added Et3N (1.5 g, 14.8 mmol) and ethyl 2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-but-2-enoic acid ethyl ester (920 mg, 2.9 mmol) at room temperature. The reaction mixture was stirred at 40-45° C. for 7 days (additional thiolacetic acid (1.5 mL) was added to the reaction mixture... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester.Ester | Ester.Carbo-thioester | c1ccsc1 | null | c1ccncc1 | HO- | null | null | null | CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)=C(C)CC.CCOC(C)=O.O=C(O)Cc1cccs1>>CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(C)SC(C)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-35fdb8f1571d47498fb8da30b6effcf0 | CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(C)SC(C)=O>>CC(S)C(Cc1ccc(N)nc1)C(=O)O | C(C)OC(C(C(C)SC(C)=O)CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O>>NC1=CC=C(C=N1)CC(C(=O)O)C(C)S | CC[O:15][C:13]([CH:4]([CH:2]([CH3:1])[S:3]C(C)=O)[CH2:5][c:6]1[cH:7][cH:8][c:9]([NH:10]C(=O)OC(C)(C)C)[n:11][cH:12]1)=[O:14]>>[CH3:1][CH:2]([SH:3])[CH:4]([CH2:5][c:6]1[cH:7][cH:8][c:9]([NH2:10])[n:11][cH:12]1)[C:13](=[O:14])[OH:15] | CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(C)SC(C)=O | CC(S)C(Cc1ccc(N)nc1)C(=O)O | null | null | Cl | Reduction | OtherReaction | df63f36502c6e187beb1211487c3f0937031934a12a3c506c12c51a17b700a31 | 9a7c4efef36aa8beb2b85c58cd3924b350f3ef529d4eb0778d927167159d9d8b | c1ccncc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].C-C-[O;H0;D2;+0:6]-[C:7](=[O;D1;H0:8])-[C:9]-[C:10](-[C;D1;H3:11])-[S;H0;D2;+0:12]-C(-C)=O>>[C;D1;H3:11]-[C:10](-[SH;D1;+0:12])-[C:9]-[C:7](=[O;D1;H0:8])-[OH;D1;+0:6].[NH2;D1;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | A solution of 3-acetylsulfanyl-2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-butyric acid ethyl ester/A (45 mg; 0.11 mmol) in concentrated HCl (2 mL) was refluxed under argon for 1 hour. The reaction mixture was allowed to cool to room temperature and concentrated under reduced pressure to afford 28.4 mg of the tit... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ether.Carbo-thioester.Boc | Carboxylic acid.Primary amine.Aliphatic thiol | null | null | c1ccncc1 | HO- | Cl | null | null | CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(C)SC(C)=O>Cl>CC(S)C(Cc1ccc(N)nc1)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0294f9f994f74d49b5d1528e5d08120d | CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(C)SC(C)=O>>CC(S)C(Cc1ccc(N)nc1)C(=O)O | C(C)OC(C(C(C)SC(C)=O)CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O>>NC1=CC=C(C=N1)CC(C(=O)O)C(C)S | CC[O:15][C:13]([CH:4]([CH:2]([CH3:1])[S:3]C(C)=O)[CH2:5][c:6]1[cH:7][cH:8][c:9]([NH:10]C(=O)OC(C)(C)C)[n:11][cH:12]1)=[O:14]>>[CH3:1][CH:2]([SH:3])[CH:4]([CH2:5][c:6]1[cH:7][cH:8][c:9]([NH2:10])[n:11][cH:12]1)[C:13](=[O:14])[OH:15] | CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(C)SC(C)=O | CC(S)C(Cc1ccc(N)nc1)C(=O)O | null | null | Cl | Reduction | OtherReaction | df63f36502c6e187beb1211487c3f0937031934a12a3c506c12c51a17b700a31 | 9a7c4efef36aa8beb2b85c58cd3924b350f3ef529d4eb0778d927167159d9d8b | c1ccncc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].C-C-[O;H0;D2;+0:6]-[C:7](=[O;D1;H0:8])-[C:9]-[C:10](-[C;D1;H3:11])-[S;H0;D2;+0:12]-C(-C)=O>>[C;D1;H3:11]-[C:10](-[SH;D1;+0:12])-[C:9]-[C:7](=[O;D1;H0:8])-[OH;D1;+0:6].[NH2;D1;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | A solution of 3-acetylsulfanyl-2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-butyric acid ethyl ester/B (55 mg; 0.14 mmol) in concentrated HCl (2 mL) was refluxed under argon for 1 hour. The reaction mixture was allowed to cool to room temperature and concentrated under reduced pressure to afford 39.4 mg of the tit... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ether.Carbo-thioester.Boc | Carboxylic acid.Primary amine.Aliphatic thiol | null | null | c1ccncc1 | HO- | Cl | null | null | CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(C)SC(C)=O>Cl>CC(S)C(Cc1ccc(N)nc1)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6feeb5c4a1da4279a7dde497c757108e | CCC=O.CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)P(=O)(OCC)OCC>>CCC=C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OCC | C(CC)=O.[H-].[Na+].C(C)OC(C(CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)P(=O)(OCC)OCC)=O.C(CC)=O>>C(C)OC(C(=CCC)CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O | O=[CH:3][CH2:2][CH3:1].CCOP(=O)(OCC)[CH:4]([CH2:5][c:6]1[cH:7][cH:8][c:9]([NH:10][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[n:18][cH:19]1)[C:20](=[O:21])[O:22][CH2:23][CH3:24]>>[CH3:1][CH2:2][CH:3]=[C:4]([CH2:5][c:6]1[cH:7][cH:8][c:9]([NH:10][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[n:18][c... | CCC=O.CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)P(=O)(OCC)OCC | CCC=C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OCC | null | null | C1CCOC1 | C-C Coupling | OtherReaction | a86984aeb4a9963534e0b081b0ecca18455fda1775f36ce168d1ca4cf966df3e | 203dd34a20dceaf1737adbf20e01b43c2424e4e4b1722d942d1a796d895396e6 | c1ccncc1 | C-C-O-P(=O)(-O-C-C)-[CH;D3;+0:1](-[C:2]-[c:3]:[c:4]:[#7;a:5])-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9].O=[CH;D2;+0:10]-[C:11]-[C;D1;H3:12]>>[#7;a:5]:[c:4]:[c:3]-[C:2]-[C;H0;D3;+0:1](=[CH;D2;+0:10]-[C:11]-[C;D1;H3:12])-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9] | null | [] | 0 | CELSIUS | 1 | HOUR | To a solution of NaH (290.5 mg, 60% in mineral oil, 7.5 mmol) in THF (25 mL) at 0° C. was added a solution of 3-(6-tert-butoxycarbonylamino-pyridin-3-yl)-2-(diethoxy-phosphoryl)-propionic acid ethyl ester (2.5 g, 5.81 mmol) in THF (30 mL). The reaction mixture was allowed to stir at 0° C. for 1 h. To the reaction was a... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Ester | null | null | c1ccncc1 | HO- | C1CCOC1 | 0 | 1 | CCC=O.CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)P(=O)(OCC)OCC>C1CCOC1>CCC=C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7acc4118a688498fb1276bc4af28fcef | CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(CC)SC(C)=O>>CCC(S)C(Cc1ccc(N)nc1)C(=O)O | C(C)OC(C(C(CC)SC(C)=O)CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O>>NC1=CC=C(C=N1)CC(C(=O)O)C(CC)S | CC[O:16][C:14]([CH:5]([CH:3]([CH2:2][CH3:1])[S:4]C(C)=O)[CH2:6][c:7]1[cH:8][cH:9][c:10]([NH:11]C(=O)OC(C)(C)C)[n:12][cH:13]1)=[O:15]>>[CH3:1][CH2:2][CH:3]([SH:4])[CH:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([NH2:11])[n:12][cH:13]1)[C:14](=[O:15])[OH:16] | CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(CC)SC(C)=O | CCC(S)C(Cc1ccc(N)nc1)C(=O)O | null | null | Cl | Reduction | OtherReaction | df63f36502c6e187beb1211487c3f0937031934a12a3c506c12c51a17b700a31 | 9a7c4efef36aa8beb2b85c58cd3924b350f3ef529d4eb0778d927167159d9d8b | c1ccncc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].C-C-[O;H0;D2;+0:6]-[C:7](=[O;D1;H0:8])-[C:9]-[C:10](-[C:11])-[S;H0;D2;+0:12]-C(-C)=O>>[C:11]-[C:10](-[SH;D1;+0:12])-[C:9]-[C:7](=[O;D1;H0:8])-[OH;D1;+0:6].[NH2;D1;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | A solution of 3-acetylsulfanyl-2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-pentanoic acid ethyl ester/B (51.6 mg; 0.13 mmol) in concentrated HCl (2 mL) was refluxed under argon for 1.5 hours. The reaction mixture was allowed to cool to room temperature and concentrated under reduced pressure to afford 34.7 mg of ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ether.Carbo-thioester.Boc | Carboxylic acid.Primary amine.Aliphatic thiol | null | null | c1ccncc1 | HO- | Cl | null | null | CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(CC)SC(C)=O>Cl>CCC(S)C(Cc1ccc(N)nc1)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f4253a0b4cec48dc8dd43cf5d0ced6ec | CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(CC)SC(C)=O>>CCC(S)C(Cc1ccc(N)nc1)C(=O)O | C(C)OC(C(C(CC)SC(C)=O)CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O>>NC1=CC=C(C=N1)CC(C(=O)O)C(CC)S | CC[O:16][C:14]([CH:5]([CH:3]([CH2:2][CH3:1])[S:4]C(C)=O)[CH2:6][c:7]1[cH:8][cH:9][c:10]([NH:11]C(=O)OC(C)(C)C)[n:12][cH:13]1)=[O:15]>>[CH3:1][CH2:2][CH:3]([SH:4])[CH:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([NH2:11])[n:12][cH:13]1)[C:14](=[O:15])[OH:16] | CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(CC)SC(C)=O | CCC(S)C(Cc1ccc(N)nc1)C(=O)O | null | null | Cl | Reduction | OtherReaction | df63f36502c6e187beb1211487c3f0937031934a12a3c506c12c51a17b700a31 | 9a7c4efef36aa8beb2b85c58cd3924b350f3ef529d4eb0778d927167159d9d8b | c1ccncc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].C-C-[O;H0;D2;+0:6]-[C:7](=[O;D1;H0:8])-[C:9]-[C:10](-[C:11])-[S;H0;D2;+0:12]-C(-C)=O>>[C:11]-[C:10](-[SH;D1;+0:12])-[C:9]-[C:7](=[O;D1;H0:8])-[OH;D1;+0:6].[NH2;D1;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | A solution of 3-acetylsulfanyl-2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-pentanoic acid ethyl ester/C (4.3 mg; 0.01 mmol) in concentrated HCl (2 mL) was refluxed under argon for 1.5 hours. The reaction mixture was allowed to cool to room temperature and concentrated under reduced pressure to afford 2.9 mg of th... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ether.Carbo-thioester.Boc | Carboxylic acid.Primary amine.Aliphatic thiol | null | null | c1ccncc1 | HO- | Cl | null | null | CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(CC)SC(C)=O>Cl>CCC(S)C(Cc1ccc(N)nc1)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-77bd6419f2c9443ba5381bda5c4957d3 | CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(CC)SC(C)=O>>CCC(S)C(Cc1ccc(N)nc1)C(=O)O | C(C)OC(C(C(CC)SC(C)=O)CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O>>NC1=CC=C(C=N1)CC(C(=O)O)C(CC)S | CC[O:16][C:14]([CH:5]([CH:3]([CH2:2][CH3:1])[S:4]C(C)=O)[CH2:6][c:7]1[cH:8][cH:9][c:10]([NH:11]C(=O)OC(C)(C)C)[n:12][cH:13]1)=[O:15]>>[CH3:1][CH2:2][CH:3]([SH:4])[CH:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([NH2:11])[n:12][cH:13]1)[C:14](=[O:15])[OH:16] | CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(CC)SC(C)=O | CCC(S)C(Cc1ccc(N)nc1)C(=O)O | null | null | Cl | Reduction | OtherReaction | df63f36502c6e187beb1211487c3f0937031934a12a3c506c12c51a17b700a31 | 9a7c4efef36aa8beb2b85c58cd3924b350f3ef529d4eb0778d927167159d9d8b | c1ccncc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].C-C-[O;H0;D2;+0:6]-[C:7](=[O;D1;H0:8])-[C:9]-[C:10](-[C:11])-[S;H0;D2;+0:12]-C(-C)=O>>[C:11]-[C:10](-[SH;D1;+0:12])-[C:9]-[C:7](=[O;D1;H0:8])-[OH;D1;+0:6].[NH2;D1;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | A solution of 3-acetylsulfanyl-2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-pentanoic acid ethyl ester/D (19.2 mg; 0.05 mmol) in concentrated HCl (2 mL) was refluxed under argon for 1.5 hours. The reaction mixture was allowed to cool to room temperature and concentrated under reduced pressure to afford 12.9 m, of ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ether.Carbo-thioester.Boc | Carboxylic acid.Primary amine.Aliphatic thiol | null | null | c1ccncc1 | HO- | Cl | null | null | CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(CC)SC(C)=O>Cl>CCC(S)C(Cc1ccc(N)nc1)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2ced570083014538a0270a15b33675f2 | CCOC(=O)c1ccc(N)nc1.O=C1CCC(=O)N1Cl>>CCOC(=O)c1cnc(N)c(Cl)c1 | ClN1C(CCC1=O)=O.C(C)OC(C1=CN=C(C=C1)N)=O>>C(C)OC(C1=CN=C(C(=C1)Cl)N)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH2:10])[cH:11][cH:13]1.O=C1CCC(=O)N1[Cl:12]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH2:10])[c:11]([Cl:12])[cH:13]1 | CCOC(=O)c1ccc(N)nc1.O=C1CCC(=O)N1Cl | CCOC(=O)c1cnc(N)c(Cl)c1 | null | null | C(C)#N | Functional Group Interconversion | Chlorination | 0c4eeb30070e87daf86c6fe6be8db4805f592c36398c82b1c29b987bb0b889d8 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccncc1 | O=C1-C-C-C(=O)-N-1-[Cl;H0;D1;+0:1].[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]1:[c:6]:[cH;D2;+0:7]:[c:8](-[N;D1;H2:9]):[#7;a:10]:[c:11]:1>>[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]1:[c:6]:[c;H0;D3;+0:7](-[Cl;H0;D1;+0:1]):[c:8](-[N;D1;H2:9]):[#7;a:10]:[c:11]:1 | 79.5 | [{"value": 79.0, "product": "C(C)OC(C1=CN=C(C(=C1)Cl)N)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.5, "product": "C(C)OC(C1=CN=C(C(=C1)Cl)N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | N-Chlorosuccinimide (21.7 g, 0.162 mol) was added to a suspension of 6-amino-nicotinic acid ethyl ester (18.0 g, 0.108 mol) in acetonitrile (270 ml) and the mixture was refluxed for 2 h. The reaction mixture was filtered and concentrated under reduced pressure. The residue was dissolved in dichloromethane, washed with ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ccncc1.C1CCNC1 | c1ccncc1 | c1ccncc1 | HO- | C(C)#N | null | null | CCOC(=O)c1ccc(N)nc1.O=C1CCC(=O)N1Cl>C(C)#N>CCOC(=O)c1cnc(N)c(Cl)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f8bd0dd4478c4b95809d11c933abc152 | CC(C)(C)OC(=O)Nc1ncc(CBr)cc1Cl.CCOC(=O)CC(=O)OCC>>CCOC(=O)C(Cc1cnc(NC(=O)OC(C)(C)C)c(Cl)c1)C(=O)OCC | [NH4+].[Cl-].C(CC(=O)OCC)(=O)OCC.[H-].[Na+].C(C)(C)(C)OC(NC1=NC=C(C=C1Cl)CBr)=O>>C(C)OC(C(C(=O)OCC)CC=1C=NC(=C(C1)Cl)NC(=O)OC(C)(C)C)=O | Br[CH2:7][c:8]1[cH:9][n:10][c:11]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[c:20]([Cl:21])[cH:22]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:23](=[O:24])[O:25][CH2:26][CH3:27]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][n:10][c:11]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:... | CC(C)(C)OC(=O)Nc1ncc(CBr)cc1Cl.CCOC(=O)CC(=O)OCC | CCOC(=O)C(Cc1cnc(NC(=O)OC(C)(C)C)c(Cl)c1)C(=O)OCC | null | null | CN(C)C=O.O.C(Cl)Cl | C-C Coupling | OtherReaction | 8175b6573d6439ec7ccc45bf6b48843ab56b46dccfc6504384c4766d09f35cc7 | d1817e44576d3a158547867a56245217a593d4f828a6d6dfaa8ed11276894e44 | c1ccncc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6].[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[CH2;D2;+0:11]-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15]>>[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[CH;D3;+0:11](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6])-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15] | 60 | [{"value": 60.0, "product": "C(C)OC(C(C(=O)OCC)CC=1C=NC(=C(C1)Cl)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | Diethyl malonate (1.87 ml, 12.31 mmol) was added to a suspension of NaH (0.54 g, 12.31 mmol, 55%) in dry DMF (15 ml) at −8° C. This mixture was stirred for 15 min. before it was added dropwise to a solution of (5-bromomethyl-3-chloro-pyridin-2-yl)-carbamic acid tert-butyl ester (3.30 g, 10.26 mmol) in dry DMF (50 ml) a... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ester | Ester.Ester | null | null | c1ccncc1 | HBr | CN(C)C=O.O.C(Cl)Cl | null | 0.25 | CC(C)(C)OC(=O)Nc1ncc(CBr)cc1Cl.CCOC(=O)CC(=O)OCC>CN(C)C=O.O.C(Cl)Cl>CCOC(=O)C(Cc1cnc(NC(=O)OC(C)(C)C)c(Cl)c1)C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f503dbc19a7340f9b5be2c028eee0c01 | CCOC(=O)C(Cc1cnc(NC(=O)OC(C)(C)C)c(Cl)c1)C(=O)OCC>>CCOC(=O)C(Cc1cnc(NC(=O)OC(C)(C)C)c(Cl)c1)C(=O)O | [OH-].[K+].C(C)OC(C(C(=O)OCC)CC=1C=NC(=C(C1)Cl)NC(=O)OC(C)(C)C)=O>>C(C)OC(C(C(=O)O)CC=1C=NC(=C(C1)Cl)NC(=O)OC(C)(C)C)=O | CC[O:25][C:23]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][c:8]1[cH:9][n:10][c:11]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[c:20]([Cl:21])[cH:22]1)=[O:24]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][n:10][c:11]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[c:... | CCOC(=O)C(Cc1cnc(NC(=O)OC(C)(C)C)c(Cl)c1)C(=O)OCC | CCOC(=O)C(Cc1cnc(NC(=O)OC(C)(C)C)c(Cl)c1)C(=O)O | null | null | C(Cl)Cl.C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccncc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7]>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 62 | [{"value": 62.0, "product": "C(C)OC(C(C(=O)O)CC=1C=NC(=C(C1)Cl)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.9, "product": "C(C)OC(C(C(=O)O)CC=1C=NC(=C(C1)Cl)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A solution of KOH (0.44 g, 6.72 mmol, 85%) in ethanol (5 ml) was added to a solution of 2-(6-tert-butoxycarbonylamino-5-chloro-pyridin-3-ylmethyl)-malonic acid diethyl ester (2.45 g, 6.11 mmol) in ethanol (25 ml) and methylene chloride (10 ml) at 0° C. The mixture was stirred for 18 h at room temperature. The solvent w... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccncc1 | Other | C(Cl)Cl.C(C)O | null | 18 | CCOC(=O)C(Cc1cnc(NC(=O)OC(C)(C)C)c(Cl)c1)C(=O)OCC>C(Cl)Cl.C(C)O>CCOC(=O)C(Cc1cnc(NC(=O)OC(C)(C)C)c(Cl)c1)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e2c9e2935db24053a2e1db4febb08675 | CCOC(=O)C(Cc1cnc(NC(=O)OC(C)(C)C)c(Cl)c1)C(=O)O>>C=C(Cc1cnc(NC(=O)OC(C)(C)C)c(Cl)c1)C(=O)OCC | C(C)NCC.O.C(C)OC(C(C(=O)O)CC=1C=NC(=C(C1)Cl)NC(=O)OC(C)(C)C)=O.C=O>>C(C)OC(C(=C)CC=1C=NC(=C(C1)Cl)NC(=O)OC(C)(C)C)=O | O=[C:1](O)[CH:2]([CH2:3][c:4]1[cH:5][n:6][c:7]([NH:8][C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[c:16]([Cl:17])[cH:18]1)[C:19](=[O:20])[O:21][CH2:22][CH3:23]>>[CH2:1]=[C:2]([CH2:3][c:4]1[cH:5][n:6][c:7]([NH:8][C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[c:16]([Cl:17])[cH:18]1)[C:19](=[O:20])[O:21... | CCOC(=O)C(Cc1cnc(NC(=O)OC(C)(C)C)c(Cl)c1)C(=O)O | C=C(Cc1cnc(NC(=O)OC(C)(C)C)c(Cl)c1)C(=O)OCC | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 485594ce7bba157615ffbb01ccede84a4e638576571b5d04649a06f3d4b7bce0 | 55e5b5078322f9f4fb0a7e9b5fc8a8cb9084e9135b447b8c441ad0800765792e | c1ccncc1 | O-[C;H0;D3;+0:1](=O)-[CH;D3;+0:2](-[C:3]-[c:4]:[c:5]:[#7;a:6])-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10]>>[#7;a:6]:[c:5]:[c:4]-[C:3]-[C;H0;D3;+0:2](=[CH2;D1;+0:1])-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10] | 65.3 | [{"value": 65.0, "product": "C(C)OC(C(=C)CC=1C=NC(=C(C1)Cl)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.3, "product": "C(C)OC(C(=C)CC=1C=NC(=C(C1)Cl)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | Diethylamine (3.67 ml, 3.67 mmol) was added dropwise followed by water (2.5 ml) and CH2Cl2 (2.5 ml) to a mixture of 2-(6-tert-butoxycarbonylamino-5-chloro-pyridin-3-ylmethyl)-malonic acid monoethyl ester (1.40 g, 3.64 mmol) and 37% aq. solution of formaldehyde (0.29 ml, 3.75 mmol) in CH2Cl2 (2 ml) at 0° C. The mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester | Ester.Vinyl | null | null | c1ccncc1 | Other | C(Cl)Cl | null | 20 | CCOC(=O)C(Cc1cnc(NC(=O)OC(C)(C)C)c(Cl)c1)C(=O)O>C(Cl)Cl>C=C(Cc1cnc(NC(=O)OC(C)(C)C)c(Cl)c1)C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2a9d04f03e0041fab320d6b1e0866204 | CCOC(=O)C(CSC(C)=O)Cc1cnc(NC(=O)OC(C)(C)C)c(Cl)c1>>Nc1ncc(CC(CS)C(=O)O)cc1Cl | C(C)OC(C(CC=1C=NC(=C(C1)Cl)NC(=O)OC(C)(C)C)CSC(C)=O)=O>>NC1=C(C=C(C=N1)CC(C(=O)O)CS)Cl | CC[O:12][C:10]([CH:7]([CH2:6][c:5]1[cH:4][n:3][c:2]([NH:1]C(=O)OC(C)(C)C)[c:14]([Cl:15])[cH:13]1)[CH2:8][S:9]C(C)=O)=[O:11]>>[NH2:1][c:2]1[n:3][cH:4][c:5]([CH2:6][CH:7]([CH2:8][SH:9])[C:10](=[O:11])[OH:12])[cH:13][c:14]1[Cl:15] | CCOC(=O)C(CSC(C)=O)Cc1cnc(NC(=O)OC(C)(C)C)c(Cl)c1 | Nc1ncc(CC(CS)C(=O)O)cc1Cl | null | null | Cl | Reduction | OtherReaction | df63f36502c6e187beb1211487c3f0937031934a12a3c506c12c51a17b700a31 | 9a7c4efef36aa8beb2b85c58cd3924b350f3ef529d4eb0778d927167159d9d8b | c1ccncc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].C-C-[O;H0;D2;+0:6]-[C:7](=[O;D1;H0:8])-[C:9]-[C:10]-[S;H0;D2;+0:11]-C(-C)=O>>[NH2;D1;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:8]=[C:7](-[OH;D1;+0:6])-[C:9]-[C:10]-[SH;D1;+0:11] | 110.5 | [{"value": 96.4, "product": "NC1=C(C=C(C=N1)CC(C(=O)O)CS)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 110.5, "product": "NC1=C(C=C(C=N1)CC(C(=O)O)CS)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-acetylsulfanylmethyl-3-(6-tert-butoxycarbonylamino-5-chloro-pyridin-3-yl)-propionic acid ethyl ester (55mg, 0.132 mmol) in concentrated HCl (4 mL) was refluxed for 90 min. The reaction was cooled and concentrated under reduced pressure to give the title compound as the HCl salt (36mg, 96.4%)
Conditions:... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ether.Carbo-thioester.Boc | Carboxylic acid.Primary amine.Aliphatic thiol | null | null | c1ccncc1 | HO- | Cl | null | null | CCOC(=O)C(CSC(C)=O)Cc1cnc(NC(=O)OC(C)(C)C)c(Cl)c1>Cl>Nc1ncc(CC(CS)C(=O)O)cc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5cb79addc89149d0942dd732ab1be80b | C=Cc1cc(C(=O)OCC)cnc1N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C>>C=Cc1cc(CO)cnc1NC(=O)OC(C)(C)C | O.CC(C)C[AlH]CC(C)C.C(C)OC(C1=CN=C(C(=C1)C=C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=O.[NH4+].[Cl-]>>C(C)(C)(C)OC(NC1=NC=C(C=C1C=C)CO)=O | CC[O:7][C:6](=O)[c:5]1[cH:4][c:3]([CH:2]=[CH2:1])[c:10]([N:11](C(=O)OC(C)(C)C)[C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[n:9][cH:8]1>>[CH2:1]=[CH:2][c:3]1[cH:4][c:5]([CH2:6][OH:7])[cH:8][n:9][c:10]1[NH:11][C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18] | C=Cc1cc(C(=O)OCC)cnc1N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C | C=Cc1cc(CO)cnc1NC(=O)OC(C)(C)C | null | null | C1CCOC1 | Reduction | OtherReaction | 20962d9bc1897de80b918f6efe4891a362b51f4c6f3af7bad47f6e2640fa482a | f7ff3a3ce995d934c8d2667c39df2283accf4ec6ad29f6be8bba5d4b604712d3 | c1ccncc1 | C-C-[O;H0;D2;+0:1]-[C;H0;D3;+0:2](=O)-[c:3]1:[c:4]:[c:5](-[C:6]=[C;D1;H2:7]):[c:8](-[N;H0;D3;+0:9](-C(=O)-O-C(-C)(-C)-C)-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13](-[C;D1;H3:14])(-[C;D1;H3:15])-[C;D1;H3:16]):[#7;a:17]:[c:18]:1>>[C;D1;H2:7]=[C:6]-[c:5]1:[c:4]:[c:3](-[CH2;D2;+0:2]-[OH;D1;+0:1]):[c:18]:[#7;a:17]:[c:8]:1-[NH;D2;... | 78.3 | [{"value": 78.0, "product": "C(C)(C)(C)OC(NC1=NC=C(C=C1C=C)CO)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.3, "product": "C(C)(C)(C)OC(NC1=NC=C(C=C1C=C)CO)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | DIBAL (25 ml, 1M in hexane) was added dropwise to a solution of 6-bis(tert-butoxycarbonyl)amino-5-vinyl-nicotinic acid ethyl ester (2.00 g, 5.1 mmol) in THF (40 ml) at 0° C. The mixture was stirred at room temperature for 1 h. NH4Cl (sat.) was added carefully followed by water, and the mixture was concentrated under re... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carbamic ester.Ester.Ether.Substituted dicarboximide.Boc | Carbamic ester.Primary alcohol | null | null | c1ccncc1 | HO- | C1CCOC1 | null | 1 | C=Cc1cc(C(=O)OCC)cnc1N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C>C1CCOC1>C=Cc1cc(CO)cnc1NC(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0b809378ed0345879f1bed7055ae6671 | BrC(Br)(Br)Br.C=Cc1cc(CO)cnc1NC(=O)OC(C)(C)C.ClCCl>>CC(C)(C)OC(=O)Nc1ncc(CBr)cc1Cl | C(C)(C)(C)OC(NC1=NC=C(C=C1C=C)CO)=O.C(Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(Br)(Br)(Br)Br>>C(C)(C)(C)OC(NC1=NC=C(C=C1Cl)CBr)=O | BrC(Br)(Br)[Br:14].C=C[c:16]1[c:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[n:10][cH:11][c:12]([CH2:13]O)[cH:15]1.ClC[Cl:17]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[n:10][cH:11][c:12]([CH2:13][Br:14])[cH:15][c:16]1[Cl:17] | BrC(Br)(Br)Br.C=Cc1cc(CO)cnc1NC(=O)OC(C)(C)C.ClCCl | CC(C)(C)OC(=O)Nc1ncc(CBr)cc1Cl | null | null | C1CCOC1 | Functional Group Addition | OtherReaction | 4dc1519e590b6ba28209c72ddad0e2c16345669a063f4691867cc18fbb162039 | dd801ea843bdac34f15405afad6fc15f7a127f35e2375c2d2fc98fe99721549c | c1ccncc1 | Br-C(-Br)(-Br)-[Br;H0;D1;+0:1].C=C-[c;H0;D3;+0:2]1:[c:3]:[c:4](-[CH2;D2;+0:5]-O):[c:6]:[#7;a:7]:[c:8]:1-[#7:9]-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13](-[C;D1;H3:14])(-[C;D1;H3:15])-[C;D1;H3:16].Cl-C-[Cl;H0;D1;+0:17]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:5]-[c:4]1:[c:6]:[#7;a:7]:[c:8](-[#7:9]-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13](-[C... | 36 | [{"value": 36.0, "product": "C(C)(C)(C)OC(NC1=NC=C(C=C1Cl)CBr)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a stirred suspension of (5-hydroxymethyl-3-vinyl-pyridin-2-yl)carbamic acid tert-butyl ester (10.0 g, 40.0 mmol) in CH2Cl2 (150 ml) and THF (60 ml) was added triphenylphosphine (11.5 g, 44.0 mmol) followed by carbontetrabromide (19.9 g, 60.0 mmol) at 0° C. The mixture was stirred at room temperature for 1 h and then... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Primary halide.Primary halide.Primary alcohol.Vinyl | Aromatic halide.Primary halide | c1ccncc1 | c1ccncc1 | c1ccncc1 | HCl.Br- | C1CCOC1 | null | 1 | BrC(Br)(Br)Br.C=Cc1cc(CO)cnc1NC(=O)OC(C)(C)C.ClCCl>C1CCOC1>CC(C)(C)OC(=O)Nc1ncc(CBr)cc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-daf3c758d7854f07aad3e69c2d3882de | C=Cc1cc(CC(C(=O)OCC)C(=O)OCC)cnc1NC(=O)OC(C)(C)C.[OH-]>>C=Cc1cc(CC(C(=O)O)C(=O)OCC)cnc1NC(=O)OC(C)(C)C | [OH-].[K+].C(C)OC(C(C(=O)OCC)CC=1C=NC(=C(C1)C=C)NC(=O)OC(C)(C)C)=O>>C(C)OC(C(C(=O)O)CC=1C=NC(=C(C1)C=C)NC(=O)OC(C)(C)C)=O | CCO[C:8]([CH:7]([CH2:6][c:5]1[cH:4][c:3]([CH:2]=[CH2:1])[c:18]([NH:19][C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[n:17][cH:16]1)[C:11](=[O:12])[O:13][CH2:14][CH3:15])=[O:9].[OH-:10]>>[CH2:1]=[CH:2][c:3]1[cH:4][c:5]([CH2:6][CH:7]([C:8](=[O:9])[OH:10])[C:11](=[O:12])[O:13][CH2:14][CH3:15])[cH:16][n:17][c:18]... | C=Cc1cc(CC(C(=O)OCC)C(=O)OCC)cnc1NC(=O)OC(C)(C)C.[OH-] | C=Cc1cc(CC(C(=O)O)C(=O)OCC)cnc1NC(=O)OC(C)(C)C | null | null | ClCCl.C(C)O | Acylation | OtherReaction | c7114ee60ff60bea14f6572ed79597c7e713bce6f0b8e5d3a4f541547512fe8b | da3aedbfec1c6be5bff80b5323fb366471c264c2a14f5b23d550d4645cd80dde | c1ccncc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8].[OH-;D0:9]>>[C:8]-[#8:7]-[C:5](=[O;D1;H0:6])-[C:3](-[C:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[OH;D1;+0:9] | 76.1 | [{"value": 76.0, "product": "C(C)OC(C(C(=O)O)CC=1C=NC(=C(C1)C=C)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.1, "product": "C(C)OC(C(C(=O)O)CC=1C=NC(=C(C1)C=C)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | A solution of KOH (0.71 g, 12.6 mmol, 85%) in ethanol (10 ml) was added to a solution of 2-(6-tert-butoxycarbonylamino-5-vinyl-pyridin-3-ylmethyl)-malonic acid diethyl ester (4.30 g, 11.0 mmol) in ethanol (25 ml) and dichloromethane (10 ml) at 0° C. The mixture was stirred for 6 h at room temperature. The solvent was e... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccncc1 | HO- | ClCCl.C(C)O | null | 6 | C=Cc1cc(CC(C(=O)OCC)C(=O)OCC)cnc1NC(=O)OC(C)(C)C.[OH-]>ClCCl.C(C)O>C=Cc1cc(CC(C(=O)O)C(=O)OCC)cnc1NC(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7b84ac93008f48beb153b198eb691b10 | C=Cc1cc(CC(C(=O)O)C(=O)OCC)cnc1NC(=O)OC(C)(C)C>>C=Cc1cc(CC(=C)C(=O)OCC)cnc1NC(=O)OC(C)(C)C | C(C)NCC.C(C)OC(C(C(=O)O)CC=1C=NC(=C(C1)C=C)NC(=O)OC(C)(C)C)=O.C=O>>C(C)OC(C(=C)CC=1C=NC(=C(C1)C=C)NC(=O)OC(C)(C)C)=O | O=[C:8](O)[CH:7]([CH2:6][c:5]1[cH:4][c:3]([CH:2]=[CH2:1])[c:16]([NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[n:15][cH:14]1)[C:9](=[O:10])[O:11][CH2:12][CH3:13]>>[CH2:1]=[CH:2][c:3]1[cH:4][c:5]([CH2:6][C:7](=[CH2:8])[C:9](=[O:10])[O:11][CH2:12][CH3:13])[cH:14][n:15][c:16]1[NH:17][C:18](=[O:19])[O:20][... | C=Cc1cc(CC(C(=O)O)C(=O)OCC)cnc1NC(=O)OC(C)(C)C | C=Cc1cc(CC(=C)C(=O)OCC)cnc1NC(=O)OC(C)(C)C | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 485594ce7bba157615ffbb01ccede84a4e638576571b5d04649a06f3d4b7bce0 | 55e5b5078322f9f4fb0a7e9b5fc8a8cb9084e9135b447b8c441ad0800765792e | c1ccncc1 | O-[C;H0;D3;+0:1](=O)-[CH;D3;+0:2](-[C:3]-[c:4]:[c:5]:[#7;a:6])-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10]>>[#7;a:6]:[c:5]:[c:4]-[C:3]-[C;H0;D3;+0:2](=[CH2;D1;+0:1])-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10] | 61.1 | [{"value": 61.0, "product": "C(C)OC(C(=C)CC=1C=NC(=C(C1)C=C)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.1, "product": "C(C)OC(C(=C)CC=1C=NC(=C(C1)C=C)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Diethylamine (0.85 ml, 8.80 mmol) was added dropwise to a mixture of 2-(6-tert-butoxycarbonylamino-5-vinyl-pyridin-3-ylmethyl)-malonic acid monoethyl ester (3.05 g, 8.37 mmol) and 37% aq. solution of formaldehyde (0.71 g, 8.80 mmol) in CH2Cl2 (2 ml) at 0° C. The mixture was stirred for 3 h at room temperature and then ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester | Ester.Vinyl | null | null | c1ccncc1 | Other | C(Cl)Cl | null | 3 | C=Cc1cc(CC(C(=O)O)C(=O)OCC)cnc1NC(=O)OC(C)(C)C>C(Cl)Cl>C=Cc1cc(CC(=C)C(=O)OCC)cnc1NC(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7d7aa3ea792444ddbc0e9d6402f114d6 | CC(=O)OC(C)=O.CCOC(=O)C(CS)Cc1cnc(NC(=O)OC(C)(C)C)c(CO)c1>>CCOC(=O)C(CSC(C)=O)Cc1cnc(NC(=O)OC(C)(C)C)c(CO)c1 | C(C)OC(C(CC=1C=NC(=C(C1)CO)NC(=O)OC(C)(C)C)CS)=O.C(C)(=O)OC(C)=O.[NH4+].[Cl-].O>>C(C)OC(C(CC=1C=NC(=C(C1)CO)NC(=O)OC(C)(C)C)CSC(C)=O)=O | CC(=O)O[C:9]([CH3:10])=[O:11].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][SH:8])[CH2:12][c:13]1[cH:14][n:15][c:16]([NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[c:25]([CH2:26][OH:27])[cH:28]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][S:8][C:9]([CH3:10])=[O:11])[CH2:12][c:13]1[cH:14][n:15][c:1... | CC(=O)OC(C)=O.CCOC(=O)C(CS)Cc1cnc(NC(=O)OC(C)(C)C)c(CO)c1 | CCOC(=O)C(CSC(C)=O)Cc1cnc(NC(=O)OC(C)(C)C)c(CO)c1 | null | null | null | Acylation | OtherReaction | d66f7449468f61f2b9f37dc16c9be702d6a3856eb6660e923598a1d7467343ca | a4ef1d5d7b2eabe1d4bef8223b8bfdc5baf9380ecbfb7dbd6ce236719aa634ef | c1ccncc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#8:4]-[C:5](=[O;D1;H0:6])-[C:7]-[C:8]-[SH;D1;+0:9]>>[#8:4]-[C:5](=[O;D1;H0:6])-[C:7]-[C:8]-[S;H0;D2;+0:9]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | 60 | [{"value": 60.0, "product": "C(C)OC(C(CC=1C=NC(=C(C1)CO)NC(=O)OC(C)(C)C)CSC(C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | A mixture of crude 3-(6-tert-butoxycarbonylamino-5-hydroxymethyl-pyridin-3-yl)-mercaptomethyl-propionic acid ethyl ester (0.38 g, 1.0 mmol) and KHCO3 (0.11 g, 1.1 mmol) in acetic acid anhydride (1 mL) was stirred at room temperature for 5 h. NH4Cl (sat.) and water was then added. The mixture was extracted with dichloro... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Aliphatic thiol | Carbo-thioester | null | null | c1ccncc1 | HO- | null | null | 5 | CC(=O)OC(C)=O.CCOC(=O)C(CS)Cc1cnc(NC(=O)OC(C)(C)C)c(CO)c1>>CCOC(=O)C(CSC(C)=O)Cc1cnc(NC(=O)OC(C)(C)C)c(CO)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f65f6c8a26fe4ff3bdf579c9118aad1b | O=C(O)C1CC(=O)N(Cc2ccccc2)C1>>OCC1CCN(Cc2ccccc2)C1 | [OH-].[Na+].COCCO[AlH2-]OCCOC.[Na+].C(C1=CC=CC=C1)N1CC(CC1=O)C(=O)O>>C(C1=CC=CC=C1)N1CC(CC1)CO | O=[C:2]([OH:1])[CH:3]1[CH2:4][C:5](=O)[N:6]([CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[CH2:14]1>>[OH:1][CH2:2][CH:3]1[CH2:4][CH2:5][N:6]([CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[CH2:14]1 | O=C(O)C1CC(=O)N(Cc2ccccc2)C1 | OCC1CCN(Cc2ccccc2)C1 | null | null | C1(=CC=CC=C1)C.C1CCOC1 | Reduction | OtherReaction | 340b9d75c65c498b95396f25adfb399eda98b80aae9ee415244b78861c5ea818 | deebadf03dbc3764fb63b73beaa8f04b4c167c96df4e2e1a68aea5ad03ed8f0d | c1ccc(CN2CCCC2)cc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[C:3]1-[C:4]-[#7:5](-[C:6])-[C;H0;D3;+0:7](=O)-[C:8]-1>>[C:6]-[#7:5]1-[C:4]-[C:3](-[CH2;D2;+0:1]-[O;D1;H1:2])-[C:8]-[CH2;D2;+0:7]-1 | 102.8 | [{"value": 102.8, "product": "C(C1=CC=CC=C1)N1CC(CC1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Red-Al (160 mL of a 3.5 M solution in toluene, 560 mmol) was added to a solution of 1-benzyl-5-oxo-pyrrolidine-3-carboxylic acid (20 g, 91 mmol) in dry THF (650 mL) under argon. The reaction mixture was refluxed for 2.5 h and then poured onto a mixture of crushed ice and NaOH (20%). The phases were separated, the aqueo... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary amide | Primary alcohol | C1CC[NH]C1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1 | Other | C1(=CC=CC=C1)C.C1CCOC1 | null | null | O=C(O)C1CC(=O)N(Cc2ccccc2)C1>C1(=CC=CC=C1)C.C1CCOC1>OCC1CCN(Cc2ccccc2)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-beace4a3209f4a8ebfd648ef8b15f3c8 | CC(C)(C)OC(=O)N1CCC(COS(=O)(=O)C(F)(F)F)C1.[Br-]>>CC(C)(C)OC(=O)N1CCC(CBr)C1 | C(C)(C)(C)OC(=O)N1CC(CC1)COS(=O)(=O)C(F)(F)F.[Li+].[Br-]>>C(C)(C)(C)OC(=O)N1CC(CC1)CBr | O=S(=O)(O[CH2:12][CH:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:14]1)C(F)(F)F.[Br-:13]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([CH2:12][Br:13])[CH2:14]1 | CC(C)(C)OC(=O)N1CCC(COS(=O)(=O)C(F)(F)F)C1.[Br-] | CC(C)(C)OC(=O)N1CCC(CBr)C1 | null | null | CC(=O)C | Functional Group Interconversion | OtherReaction | 8c25114f6e35a2eaed073de14ecf22ab2f1e189db18bca7f82e8c0b93444a0b1 | 23ab3c443e9999f7cd1707e344529116afaee675d7ed2bc5da5c5c7516fe5ad6 | C1CCNC1 | F-C(-F)(-F)-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4]-[#7:5].[Br-;H0;D0:6]>>[#7:5]-[C:4]-[C:2](-[CH2;D2;+0:1]-[Br;H0;D1;+0:6])-[C:3] | 78 | [{"value": 78.0, "product": "C(C)(C)(C)OC(=O)N1CC(CC1)CBr", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.9, "product": "C(C)(C)(C)OC(=O)N1CC(CC1)CBr", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-trifluoromethanesulfonyloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (3.85 g, 13.8 mmol) and LiBr (3.61 g, 42 mmol) in dry acetone (30 mL) was refluxed overnight. The reaction mixture was allowed to cool to room temperature, filtered and concentrated. The residue was dissolved in CH2Cl2 and w... | 10.6084/m9.figshare.5104873.v1 | null | Triflate | Primary halide | null | null | C1CC[NH]C1 | TfOH | CC(=O)C | null | null | CC(C)(C)OC(=O)N1CCC(COS(=O)(=O)C(F)(F)F)C1.[Br-]>CC(=O)C>CC(C)(C)OC(=O)N1CCC(CBr)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-524293e2c7514eb993aaebdfd4d8dc85 | CC(C)(C)OC(=O)N1CCC(CBr)C1.CCOC(=O)CC(=O)OCC>>CCOC(=O)C(CC1CCN(C(=O)OC(C)(C)C)C1)C(=O)OCC | C(C)(C)(C)OC(=O)N1CC(CC1)CBr.C(CC(=O)OCC)(=O)OCC.[H-].[Na+]>>C(C)OC(C(C(=O)OCC)CC1CN(CC1)C(=O)OC(C)(C)C)=O | Br[CH2:7][CH:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:20](=[O:21])[O:22][CH2:23][CH3:24]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][CH:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19... | CC(C)(C)OC(=O)N1CCC(CBr)C1.CCOC(=O)CC(=O)OCC | CCOC(=O)C(CC1CCN(C(=O)OC(C)(C)C)C1)C(=O)OCC | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 8175b6573d6439ec7ccc45bf6b48843ab56b46dccfc6504384c4766d09f35cc7 | d1817e44576d3a158547867a56245217a593d4f828a6d6dfaa8ed11276894e44 | C1CCNC1 | Br-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4]-[#7:5].[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[CH2;D2;+0:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14]>>[#7:5]-[C:4]-[C:2](-[CH2;D2;+0:1]-[CH;D3;+0:10](-[C:8](=[O;D1;H0:9])-[#8:7]-[C:6])-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14])-[C:3] | 45.1 | [{"value": 45.0, "product": "C(C)OC(C(C(=O)OCC)CC1CN(CC1)C(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.1, "product": "C(C)OC(C(C(=O)OCC)CC1CN(CC1)C(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Diethyl malonate (1.93 mL, 12.7 mmol) was added dropwise to a solution of NaH (60%; 0.51 g, 12.8 mmol) in dry THF (15 mL) at 0° C. The mixture was stirred at room temperature for 1 h after which it was added to a refluxed mixture of 3-bromomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (2.8 g, 10.6 mmol) in dry ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ester | Ester.Ester | null | null | C1CC[NH]C1 | HBr | C1CCOC1 | null | 1 | CC(C)(C)OC(=O)N1CCC(CBr)C1.CCOC(=O)CC(=O)OCC>C1CCOC1>CCOC(=O)C(CC1CCN(C(=O)OC(C)(C)C)C1)C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f8a9d8a25cad409b9d662986ef9f9bf4 | CCOC(=O)C(CC1CCN(C(=O)OC(C)(C)C)C1)C(=O)OCC>>CCOC(=O)C(CC1CCN(C(=O)OC(C)(C)C)C1)C(=O)O | [OH-].[K+].C(C)OC(C(C(=O)OCC)CC1CN(CC1)C(=O)OC(C)(C)C)=O>>C(C)OC(C(C(=O)O)CC1CN(CC1)C(=O)OC(C)(C)C)=O | CC[O:22][C:20]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][CH:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19]1)=[O:21]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][CH:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19]1)[C:20](=[O:21... | CCOC(=O)C(CC1CCN(C(=O)OC(C)(C)C)C1)C(=O)OCC | CCOC(=O)C(CC1CCN(C(=O)OC(C)(C)C)C1)C(=O)O | null | null | C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | C1CCNC1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7]>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 81.4 | [{"value": 81.0, "product": "C(C)OC(C(C(=O)O)CC1CN(CC1)C(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.4, "product": "C(C)OC(C(C(=O)O)CC1CN(CC1)C(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of KOH (0.26 g; 4.6 mmol) in ethanol (7 mL) was added to a solution of 2-(1-tert-butoxycarbonyl-pyrrolidin-3-ylmethyl)-malonic acid diethyl ester (1.52 g; 4.4 mmol) in ethanol (7 mL) at 0° C. The reaction mixture was stirred at room temperature overnight, concentrated under reduced pressure and the residue w... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CC[NH]C1 | Other | C(C)O | null | 8 | CCOC(=O)C(CC1CCN(C(=O)OC(C)(C)C)C1)C(=O)OCC>C(C)O>CCOC(=O)C(CC1CCN(C(=O)OC(C)(C)C)C1)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-96d2ccb1e558411880610874f816df95 | CCOC(=O)C(CC1CCN(C(=O)OC(C)(C)C)C1)C(=O)O>>CCOC(=C=C=O)CC1CCN(C(=O)OC(C)(C)C)C1 | C(C)NCC.C(C)OC(C(C(=O)O)CC1CN(CC1)C(=O)OC(C)(C)C)=O.C=O.C(Cl)Cl.O>>C(C)(C)(C)OC(=O)N1CC(CC1)CC(=C=C=O)OCC | O=[C:5]([O:3][CH2:2][CH3:1])[CH:4]([C:6](O)=[O:7])[CH2:8][CH:9]1[CH2:10][CH2:11][N:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:20]1>>[CH3:1][CH2:2][O:3][C:4](=[C:5]=[C:6]=[O:7])[CH2:8][CH:9]1[CH2:10][CH2:11][N:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:20]1 | CCOC(=O)C(CC1CCN(C(=O)OC(C)(C)C)C1)C(=O)O | CCOC(=C=C=O)CC1CCN(C(=O)OC(C)(C)C)C1 | null | null | null | Miscellaneous | OtherReaction | 978e27964be02de26cc65cc6266771af9a8bcbab956caa1deb03d23f3a947694 | 1d4797fe85cb5cf66fb76d1d846f31e346d166476722b454b707ac52362ae9c2 | C1CCNC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3](-[C:4]-[C:5])-[C;H0;D3;+0:6](=O)-[O;H0;D2;+0:7]-[C:8]-[C;D1;H3:9]>>[C:5]-[C:4]-[C;H0;D3;+0:3](=[C;H0;D2;+0:6]=[C;H0;D2;+0:1]=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C:8]-[C;D1;H3:9] | 87 | [{"value": 87.0, "product": "C(C)(C)(C)OC(=O)N1CC(CC1)CC(=C=C=O)OCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Diethyl amine (0.34 mL; 3.3 mmol) was added to a mixture of 2-(1-tert-butoxycarbonyl-pyrrolidin-3-ylmethyl)-malonic acid monoethyl ester (0.69 g, 2.19 mmol) in 36% aqueous solution of formaldehyde (0.27 mL, 3.5 mmol), CH2Cl2 (1.6 mL) and water (1.6 mL) at 0° C. The reaction mixture was stirred at room temperature overn... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester | Ether | null | null | C1CC[NH]C1 | HO- | null | null | 8 | CCOC(=O)C(CC1CCN(C(=O)OC(C)(C)C)C1)C(=O)O>>CCOC(=C=C=O)CC1CCN(C(=O)OC(C)(C)C)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f22901cbac204dc0a0373c91444823ac | C=C(CC1CCN(C(=O)OC(C)(C)C)C1)C(=O)OCC.CC(O)=S>>CCOC(=O)C(CSC(C)=O)CC1CCN(C(=O)OC(C)(C)C)C1 | C(C)(=S)O.C(C)(C)(C)OC(=O)N1CC(CC1)CC(=C)C(=O)OCC.C(C)N(CC)CC>>C(C)(C)(C)OC(=O)N1CC(CC1)CC(CSC(C)=O)C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH2:7])[CH2:12][CH:13]1[CH2:14][CH2:15][N:16]([C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH2:24]1.[S:8]=[C:9]([CH3:10])[OH:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][S:8][C:9]([CH3:10])=[O:11])[CH2:12][CH:13]1[CH2:14][CH2:15][N:16]([C:17](=[O:18])[O:19][C:2... | C=C(CC1CCN(C(=O)OC(C)(C)C)C1)C(=O)OCC.CC(O)=S | CCOC(=O)C(CSC(C)=O)CC1CCN(C(=O)OC(C)(C)C)C1 | null | null | null | Protection | OtherReaction | 56aa090d67fbecbea8a1963579cc34949775a09653b2b2f2795c609c60e70c77 | 5a9b0d631147b21b844b3c73866d1d81ab543538a176ebae28118ae7e39e572f | C1CCNC1 | [C;D1;H3:1]-[C;H0;D3;+0:2](-[OH;D1;+0:3])=[S;H0;D1;+0:4].[C:5]-[C:6]-[C;H0;D3;+0:7](=[CH2;D1;+0:8])-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12]>>[C:5]-[C:6]-[CH;D3;+0:7](-[CH2;D2;+0:8]-[S;H0;D2;+0:4]-[C;H0;D3;+0:2](-[C;D1;H3:1])=[O;H0;D1;+0:3])-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12] | 79 | [{"value": 79.0, "product": "C(C)(C)(C)OC(=O)N1CC(CC1)CC(CSC(C)=O)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 23 | HOUR | Thioacetic acid (5 mL), which had been cooled to 0° C., was added to a mixture of 3-(2-ethoxycarbonyl-allyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.72 g; 2.54 mmol) and triethyl amine (0.37 mL; 2.67 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 30 minutes, at room temperature for 23 hours and ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Thiocarbonyl.Vinyl | Ester.Carbo-thioester | null | null | C1CC[NH]C1 | null | null | 0 | 23 | C=C(CC1CCN(C(=O)OC(C)(C)C)C1)C(=O)OCC.CC(O)=S>>CCOC(=O)C(CSC(C)=O)CC1CCN(C(=O)OC(C)(C)C)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-931374e168cd47a79a44f80eab695a77 | CCOC(=O)C(CSC(C)=O)CC1CCN(C(=O)OC(C)(C)C)C1>>O=C(O)C(CS)CC1CCNC1 | C(C)(C)(C)OC(=O)N1CC(CC1)CC(CSC(C)=O)C(=O)OCC>>SCC(C(=O)O)CC1CNCC1 | CC[O:3][C:2](=[O:1])[CH:4]([CH2:5][S:6]C(C)=O)[CH2:7][CH:8]1[CH2:9][CH2:10][N:11](C(=O)OC(C)(C)C)[CH2:12]1>>[O:1]=[C:2]([OH:3])[CH:4]([CH2:5][SH:6])[CH2:7][CH:8]1[CH2:9][CH2:10][NH:11][CH2:12]1 | CCOC(=O)C(CSC(C)=O)CC1CCN(C(=O)OC(C)(C)C)C1 | O=C(O)C(CS)CC1CCNC1 | null | null | Cl | Reduction | OtherReaction | b3a21a2e34c384490a08d5beb2b8761fce5e4cbc55f8d7e96dda8b2a55b0b634 | 7c1ca95b00197a07f56646a388ca189ac8e567fcfb6f71ccaeb0441307d76709 | C1CCNC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1.C-C-[O;H0;D2;+0:6]-[C:7](=[O;D1;H0:8])-[C:9]-[C:10]-[S;H0;D2;+0:11]-C(-C)=O>>[C:2]1-[C:3]-[C:4]-[C:5]-[NH;D2;+0:1]-1.[O;D1;H0:8]=[C:7](-[OH;D1;+0:6])-[C:9]-[C:10]-[SH;D1;+0:11] | null | [] | null | null | null | null | A solution of 3-(3-acetylsulfanyl-2-ethoxycarbonyl-propyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.52 g; 1.45 mmol) in concentrated HCl (15 mL) was refluxed under argon for 1 h. The reaction mixture was allowed to cool to room temperature and concentrated under reduced pressure to afford a diasteromeric mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ether.Carbo-thioester.Boc | Carboxylic acid.Secondary amine.Aliphatic thiol | C1CC[NH]C1 | C1CCNC1 | C1CCNC1 | HO- | Cl | null | null | CCOC(=O)C(CSC(C)=O)CC1CCN(C(=O)OC(C)(C)C)C1>Cl>O=C(O)C(CS)CC1CCNC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5e86e143ec844908803c2782f948e0a9 | CC(C)(C)OC(=O)N[C@@H]1C=C[C@H](CO)C1.CS(=O)(=O)Cl>>CC(C)(C)OC(=O)N[C@H]1C=C[C@@H](COS(C)(=O)=O)C1 | CS(=O)(=O)Cl.C(C)(C)(C)OC(N[C@@H]1C=C[C@@H](C1)CO)=O.C(C)N(CC)CC>>C(C)(C)(C)OC(=O)N[C@H]1C=C[C@H](C1)COS(=O)(=O)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@@H:9]1[CH:10]=[CH:11][C@H:12]([CH2:13][OH:14])[CH2:19]1.Cl[S:15]([CH3:16])(=[O:17])=[O:18]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH:10]=[CH:11][C@@H:12]([CH2:13][O:14][S:15]([CH3:16])(=[O:17])=[O:18])[CH2:19]1 | CC(C)(C)OC(=O)N[C@@H]1C=C[C@H](CO)C1.CS(=O)(=O)Cl | CC(C)(C)OC(=O)N[C@H]1C=C[C@@H](COS(C)(=O)=O)C1 | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | C1=CCCC1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]=[C:6]-[C:7]-[C:8]-[OH;D1;+0:9]>>[C:5]=[C:6]-[C:7]-[C:8]-[O;H0;D2;+0:9]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | null | [] | null | null | 8 | HOUR | Methanesulfonyl chloride (0.76 mL, 9.8 mmol) was added to a solution of cis-(4-hydroxymethyl-cyclopent-2-enyl)-carbamic acid tert-butyl ester (2 g, 9.4 mmol) and triethyl amine (1.96 mL,14.1 mmol) in CH2Cl2 (30 mL) at 0° C. The reaction mixture was stirred at room temperature overnight. After filtration CH2Cl2 was adde... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | C1=CCCC1 | HCl | C(Cl)Cl | null | 8 | CC(C)(C)OC(=O)N[C@@H]1C=C[C@H](CO)C1.CS(=O)(=O)Cl>C(Cl)Cl>CC(C)(C)OC(=O)N[C@H]1C=C[C@@H](COS(C)(=O)=O)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-652ce7d0074a4fb2b3075afd82dbebc3 | CC(C)(C)OC(=O)N[C@H]1C=C[C@@H](COS(C)(=O)=O)C1.[Br-]>>CC(C)(C)OC(=O)N[C@@H]1C=C[C@H](CBr)C1 | C(C)(C)(C)OC(=O)N[C@H]1C=C[C@H](C1)COS(=O)(=O)C.[Li+].[Br-]>>C(C)(C)(C)OC(N[C@@H]1C=C[C@@H](C1)CBr)=O | CS(=O)(=O)O[CH2:13][C@@H:12]1[CH:11]=[CH:10][C@H:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:15]1.[Br-:14]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@@H:9]1[CH:10]=[CH:11][C@H:12]([CH2:13][Br:14])[CH2:15]1 | CC(C)(C)OC(=O)N[C@H]1C=C[C@@H](COS(C)(=O)=O)C1.[Br-] | CC(C)(C)OC(=O)N[C@@H]1C=C[C@H](CBr)C1 | null | null | CC(=O)C | Functional Group Interconversion | OtherReaction | 119410ad0456baafba3b2935b12d3e44977c506a6dd8cacdd3e4fe37abe9db9f | ddf832dd4937bef392b42ed4281006ae20524cc7fc61b350edeb12d7b5bf783f | C1=CCCC1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]1-[C:3]=[C:4]-[C:5]-[C:6]-1.[Br-;H0;D0:7]>>[Br;H0;D1;+0:7]-[CH2;D2;+0:1]-[C:2]1-[C:3]=[C:4]-[C:5]-[C:6]-1 | 94 | [{"value": 94.0, "product": "C(C)(C)(C)OC(N[C@@H]1C=C[C@@H](C1)CBr)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.9, "product": "C(C)(C)(C)OC(N[C@@H]1C=C[C@@H](C1)CBr)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of cis-methanesulfonic acid 4-tert-butoxycarbonylamino-cyclopent-2-enylmethyl ester (2.51 g, 8.6 mmol) and LiBr (2.24 g, 25.8 mmol) in dry acetone (20 mL) was refluxed overnight. The reaction mixture was allowed to cool to room temperature, filtered and concentrated. The residue was dissolved in CH2Cl2 and wa... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate | Primary halide | null | null | C1=CCCC1 | MsOH.HO- | CC(=O)C | null | null | CC(C)(C)OC(=O)N[C@H]1C=C[C@@H](COS(C)(=O)=O)C1.[Br-]>CC(=O)C>CC(C)(C)OC(=O)N[C@@H]1C=C[C@H](CBr)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-01ef05968dd24c929b5741933b41a1aa | CC(C)(C)OC(=O)N[C@@H]1C=C[C@H](CBr)C1.CCOC(=O)CC(=O)OCC>>CCOC(=O)C(C[C@@H]1C=C[C@H](NC(=O)OC(C)(C)C)C1)C(=O)OCC | CCOC(=O)C.C(CC(=O)OCC)(=O)OCC.[H-].[Na+].C(C)(C)(C)OC(N[C@@H]1C=C[C@@H](C1)CBr)=O>>C(C)OC(C(C(=O)OCC)C[C@@H]1C=C[C@@H](C1)NC(=O)OC(C)(C)C)=O | Br[CH2:7][C@H:8]1[CH:9]=[CH:10][C@@H:11]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:20]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:21](=[O:22])[O:23][CH2:24][CH3:25]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][C@@H:8]1[CH:9]=[CH:10][C@H:11]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:... | CC(C)(C)OC(=O)N[C@@H]1C=C[C@H](CBr)C1.CCOC(=O)CC(=O)OCC | CCOC(=O)C(C[C@@H]1C=C[C@H](NC(=O)OC(C)(C)C)C1)C(=O)OCC | null | null | CN(C)C=O | C-C Coupling | OtherReaction | 8175b6573d6439ec7ccc45bf6b48843ab56b46dccfc6504384c4766d09f35cc7 | d1817e44576d3a158547867a56245217a593d4f828a6d6dfaa8ed11276894e44 | C1=CCCC1 | Br-[CH2;D2;+0:1]-[C:2]1-[C:3]-[C:4]-[C:5]=[C:6]-1.[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[CH2;D2;+0:11]-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15]>>[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[CH;D3;+0:11](-[CH2;D2;+0:1]-[C:2]1-[C:3]-[C:4]-[C:5]=[C:6]-1)-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15] | 58.3 | [{"value": 58.0, "product": "C(C)OC(C(C(=O)OCC)C[C@@H]1C=C[C@@H](C1)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.3, "product": "C(C)OC(C(C(=O)OCC)C[C@@H]1C=C[C@@H](C1)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 19 | HOUR | Diethyl malonate (1.29 mL, 8.5 mmol) was added to a mixture of NaH (60%, 0.34 g; 8.5 mmol) in DMF (10 mL). After stirring at room temperature for 15 min a solution of cis-(4-bromomethyl-cyclopent-2-enyl)-carbamic acid tert-butyl ester (1.95 g, 7.1 mmol) in DMF (12 mL) was added, and the reaction mixture was stirred at ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ester | Ester.Ester | null | null | C1=CCCC1 | HBr | CN(C)C=O | 60 | 19 | CC(C)(C)OC(=O)N[C@@H]1C=C[C@H](CBr)C1.CCOC(=O)CC(=O)OCC>CN(C)C=O>CCOC(=O)C(C[C@@H]1C=C[C@H](NC(=O)OC(C)(C)C)C1)C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-63e0465be5124fb2b74f57b8ac4c8fcc | CCOC(=O)C(C[C@@H]1C=C[C@H](NC(=O)OC(C)(C)C)C1)C(=O)OCC>>CCOC(=O)C(C[C@@H]1C=C[C@H](NC(=O)OC(C)(C)C)C1)C(=O)O | [OH-].[K+].C(C)OC(C(C(=O)OCC)C[C@@H]1C=C[C@@H](C1)NC(=O)OC(C)(C)C)=O>>C(C)OC(C(C(=O)O)C[C@@H]1C=C[C@@H](C1)NC(=O)OC(C)(C)C)=O | CC[O:23][C:21]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][C@@H:8]1[CH:9]=[CH:10][C@H:11]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:20]1)=[O:22]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][C@@H:8]1[CH:9]=[CH:10][C@H:11]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH... | CCOC(=O)C(C[C@@H]1C=C[C@H](NC(=O)OC(C)(C)C)C1)C(=O)OCC | CCOC(=O)C(C[C@@H]1C=C[C@H](NC(=O)OC(C)(C)C)C1)C(=O)O | null | null | [Cl-].[Na+].O.C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | C1=CCCC1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7]>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 82.1 | [{"value": 81.0, "product": "C(C)OC(C(C(=O)O)C[C@@H]1C=C[C@@H](C1)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.1, "product": "C(C)OC(C(C(=O)O)C[C@@H]1C=C[C@@H](C1)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of KOH (0.19 g; 3.4 mmol) in ethanol (6 mL) was added to a solution of 2-(Cis-4-tert-butoxycarbonylamino-cyclopent-2-enylmethyl)-malonic acid diethyl ester (1.15 g; 3.2 mmol) in ethanol (6 mL) at 0° C. The reaction mixture was stirred at room temperature overnight, concentrated and ice-water (400 mL) was add... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1=CCCC1 | Other | [Cl-].[Na+].O.C(C)O | null | 8 | CCOC(=O)C(C[C@@H]1C=C[C@H](NC(=O)OC(C)(C)C)C1)C(=O)OCC>[Cl-].[Na+].O.C(C)O>CCOC(=O)C(C[C@@H]1C=C[C@H](NC(=O)OC(C)(C)C)C1)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6cc91569459a484089d3ec720f658960 | CCOC(=O)C(C[C@@H]1C=C[C@H](NC(=O)OC(C)(C)C)C1)C(=O)O>>C=C(C[C@@H]1C=C[C@H](NC(=O)OC(C)(C)C)C1)C(=O)OCC | C(C)NCC.C(C)OC(C(C(=O)O)C[C@@H]1C=C[C@@H](C1)NC(=O)OC(C)(C)C)=O.C=O.C(Cl)Cl>>C(C)OC(C(=C)C[C@@H]1C=C[C@@H](C1)NC(=O)OC(C)(C)C)=O | O=[C:1](O)[CH:2]([CH2:3][C@@H:4]1[CH:5]=[CH:6][C@H:7]([NH:8][C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:16]1)[C:17](=[O:18])[O:19][CH2:20][CH3:21]>>[CH2:1]=[C:2]([CH2:3][C@@H:4]1[CH:5]=[CH:6][C@H:7]([NH:8][C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:16]1)[C:17](=[O:18])[O:19][CH2:20][CH3:... | CCOC(=O)C(C[C@@H]1C=C[C@H](NC(=O)OC(C)(C)C)C1)C(=O)O | C=C(C[C@@H]1C=C[C@H](NC(=O)OC(C)(C)C)C1)C(=O)OCC | null | null | O | Miscellaneous | OtherReaction | 485594ce7bba157615ffbb01ccede84a4e638576571b5d04649a06f3d4b7bce0 | 55e5b5078322f9f4fb0a7e9b5fc8a8cb9084e9135b447b8c441ad0800765792e | C1=CCCC1 | O-[C;H0;D3;+0:1](=O)-[CH;D3;+0:2](-[C:3]-[C:4]-[C:5]=[C:6])-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10]>>[C:10]-[#8:9]-[C:7](=[O;D1;H0:8])-[C;H0;D3;+0:2](=[CH2;D1;+0:1])-[C:3]-[C:4]-[C:5]=[C:6] | 94.8 | [{"value": 94.0, "product": "C(C)OC(C(=C)C[C@@H]1C=C[C@@H](C1)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.8, "product": "C(C)OC(C(=C)C[C@@H]1C=C[C@@H](C1)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Diethyl amine (0.31 mL; 3.0 mmol) was added to a mixture of 2-(cis-4-tert-butoxycarbonylamino-cyclopent-2-enylmethyl)-malonic acid monoethyl ester (0.66 g, 2.0 mmol) in 36% aqueous solution of formaldehyde (0.25 mL, 3.2 mmol), CH2Cl2 (1.6 mL) and water (1.6 mL) at 0° C. The reaction mixture was stirred at room temperat... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester | Ester.Vinyl | null | null | C1=CCCC1 | Other | O | null | 8 | CCOC(=O)C(C[C@@H]1C=C[C@H](NC(=O)OC(C)(C)C)C1)C(=O)O>O>C=C(C[C@@H]1C=C[C@H](NC(=O)OC(C)(C)C)C1)C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f6561cbd5a024ed5996af4867dc9c9cf | C=C(C[C@@H]1C=C[C@H](NC(=O)OC(C)(C)C)C1)C(=O)OCC.CC(O)=S>>CCOC(=O)C(CSC(C)=O)C[C@@H]1C=C[C@H](NC(=O)OC(C)(C)C)C1 | C(C)(=S)O.C(C)OC(C(=C)C[C@@H]1C=C[C@@H](C1)NC(=O)OC(C)(C)C)=O.C(C)N(CC)CC>>C(C)OC(C(C[C@@H]1C=C[C@@H](C1)NC(=O)OC(C)(C)C)CSC(C)=O)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH2:7])[CH2:12][C@@H:13]1[CH:14]=[CH:15][C@H:16]([NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25]1.[S:8]=[C:9]([CH3:10])[OH:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][S:8][C:9]([CH3:10])=[O:11])[CH2:12][C@@H:13]1[CH:14]=[CH:15][C@H:16]([NH:17][C:18... | C=C(C[C@@H]1C=C[C@H](NC(=O)OC(C)(C)C)C1)C(=O)OCC.CC(O)=S | CCOC(=O)C(CSC(C)=O)C[C@@H]1C=C[C@H](NC(=O)OC(C)(C)C)C1 | null | null | null | Protection | OtherReaction | 56aa090d67fbecbea8a1963579cc34949775a09653b2b2f2795c609c60e70c77 | 5a9b0d631147b21b844b3c73866d1d81ab543538a176ebae28118ae7e39e572f | C1=CCCC1 | [C;D1;H3:1]-[C;H0;D3;+0:2](-[OH;D1;+0:3])=[S;H0;D1;+0:4].[C:5]=[C:6]-[C:7]-[C:8]-[C;H0;D3;+0:9](=[CH2;D1;+0:10])-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14]>>[C:5]=[C:6]-[C:7]-[C:8]-[CH;D3;+0:9](-[CH2;D2;+0:10]-[S;H0;D2;+0:4]-[C;H0;D3;+0:2](-[C;D1;H3:1])=[O;H0;D1;+0:3])-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14] | 65 | [{"value": 65.0, "product": "C(C)OC(C(C[C@@H]1C=C[C@@H](C1)NC(=O)OC(C)(C)C)CSC(C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 19 | HOUR | Thioacetic acid (4 mL), which had been cooled to 0° C., was added to a mixture of 2-(cis4-tert-butoxycarbonylamino-cyclopent-2-enylmethyl)-acrylic acid ethyl ester (0.56 g, 1.9 mmol) and triethyl amine (0.28 mL, 2.0 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 30 min, at room temperature for 19 h and th... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Thiocarbonyl.Vinyl | Ester.Carbo-thioester | null | null | C1=CCCC1 | null | null | 0 | 19 | C=C(C[C@@H]1C=C[C@H](NC(=O)OC(C)(C)C)C1)C(=O)OCC.CC(O)=S>>CCOC(=O)C(CSC(C)=O)C[C@@H]1C=C[C@H](NC(=O)OC(C)(C)C)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e0f29dfe808d49c1ba266330dd8f52c3 | C=C(CBr)C(=O)OCC.CC(C)(C)OC(=O)N1CCNCC1>>C=C(CN1CCN(C(=O)OC(C)(C)C)CC1)C(=O)OCC | C(C)N(C(C)C)C(C)C.C(C)OC(C(=C)CBr)=O.C(C)(C)(C)OC(=O)N1CCNCC1>>C(C)(C)(C)OC(=O)N1CCN(CC1)CC(=C)C(=O)OCC | Br[CH2:3][C:2](=[CH2:1])[C:17](=[O:18])[O:19][CH2:20][CH3:21].[NH:4]1[CH2:5][CH2:6][N:7]([C:8](=[O:9])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])[CH2:15][CH2:16]1>>[CH2:1]=[C:2]([CH2:3][N:4]1[CH2:5][CH2:6][N:7]([C:8](=[O:9])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])[CH2:15][CH2:16]1)[C:17](=[O:18])[O:19][CH2:20][CH3:21] | C=C(CBr)C(=O)OCC.CC(C)(C)OC(=O)N1CCNCC1 | C=C(CN1CCN(C(=O)OC(C)(C)C)CC1)C(=O)OCC | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | C1CNCCN1 | Br-[CH2;D2;+0:1]-[C:2](=[C;D1;H2:3])-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[C:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[C:2](=[C;D1;H2:3])-[CH2;D2;+0:1]-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-1 | 82.3 | [{"value": 82.0, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)CC(=C)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.3, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)CC(=C)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of 2-bromomethyl-acrylic acid ethyl ester (1.93 g, 10 mmol) in N,N-dimethylformamide (25 mL) was added piperazine-1-carboxylic acid tert-butyl ester (1.86 g, 10 mmol) and then, dropwise, ethyl-diisopropyl-amine (1.71 mL, 10 mmol). After stirring for 16 h at room temperature the solvent was removed under r... | 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 | HBr | CN(C=O)C | null | 16 | C=C(CBr)C(=O)OCC.CC(C)(C)OC(=O)N1CCNCC1>CN(C=O)C>C=C(CN1CCN(C(=O)OC(C)(C)C)CC1)C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-98ac93ea0169462ba5093a6afc91276c | C=C(CN1CCN(C(=O)OC(C)(C)C)CC1)C(=O)OCC.O=C(O)Cc1cccs1>>CCOC(=O)C(CSC(C)=O)CN1CCN(C(=O)OC(C)(C)C)CC1 | S1C(=CC=C1)CC(=O)O.C(O)([O-])=O.[Na+].C(C)(C)(C)OC(=O)N1CCN(CC1)CC(=C)C(=O)OCC.S1C(=CC=C1)CC(=O)O.C(C)N(CC)CC>>C(C)(C)(C)OC(=O)N1CCN(CC1)CC(CSC(C)=O)C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH2:7])[CH2:12][N:13]1[CH2:14][CH2:15][N:16]([C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH2:24][CH2:25]1.O[C:9]([CH2:10]c1ccc[s:8]1)=[O:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][S:8][C:9]([CH3:10])=[O:11])[CH2:12][N:13]1[CH2:14][CH2:15][N:16]([C:17](=[O:18... | C=C(CN1CCN(C(=O)OC(C)(C)C)CC1)C(=O)OCC.O=C(O)Cc1cccs1 | CCOC(=O)C(CSC(C)=O)CN1CCN(C(=O)OC(C)(C)C)CC1 | null | null | null | Protection | OtherReaction | fb3b4e3d7778aa7d2f1a50870b8a9fd63e27e6c3c62ef89d2ec7453847e4460c | 18c447ca8348bba090959c337490d0ae7d7ad114bc7027df349f35a0d5192c0d | C1CNCCN1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-c1:[s;H0;D2;+0:4]:c:c:c:1.[#7:5]-[C:6]-[C;H0;D3;+0:7](=[CH2;D1;+0:8])-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12]>>[#7:5]-[C:6]-[CH;D3;+0:7](-[CH2;D2;+0:8]-[S;H0;D2;+0:4]-[C;H0;D3;+0:1](-[CH3;D1;+0:3])=[O;D1;H0:2])-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12] | 9.4 | [{"value": 9.4, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)CC(CSC(C)=O)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | DAY | To crude 4-(2-ethoxycarbonyl-allyl)-piperazine-1-carboxylic acid tert-butyl ester (2.45 g, 8.2 mmol) was added thiolacetic acid (7.5 mL) under argon. The mixture was cooled to 0° C. and triethylamine (1.14 mL, 8.2 mmol) was added dropwise. The mixture was then stirred at room temperature for 2 d and thiolacetic acid (2... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester.Vinyl | Ester.Carbo-thioester | c1ccsc1 | null | C1C[NH]CC[NH]1 | HO- | null | 0 | 48 | C=C(CN1CCN(C(=O)OC(C)(C)C)CC1)C(=O)OCC.O=C(O)Cc1cccs1>>CCOC(=O)C(CSC(C)=O)CN1CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2038decc37924e4b995807afaba5bba6 | CCOC(=O)C(=Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OCC>>CCOC(=O)C(C(=O)OCC)C(CC)c1ccc(NC(=O)OC(C)(C)C)nc1 | C(C)[Mg]Br.[Cl-].[NH4+].C(C)OC(C(C(=O)OCC)=CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O>>C(C)OC(C(C(=O)OCC)C(CC)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([C:7](=[O:8])[O:9][CH2:10][CH3:11])=[CH:12][c:15]1[cH:16][cH:17][c:18]([NH:19][C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[n:27][cH:28]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([C:7](=[O:8])[O:9][CH2:10][CH3:11])[CH:12]([CH2:13][CH3:14])[c:15]1[cH:16][cH:17][c:18]([NH:1... | CCOC(=O)C(=Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OCC | CCOC(=O)C(C(=O)OCC)C(CC)c1ccc(NC(=O)OC(C)(C)C)nc1 | null | [Cu](I)I | O1CCCC1.C(C)OCC.N | Miscellaneous | OtherReaction | 6586cb8fb9074fe79a2f08ccdc9c7ab8f943f0a45ff8db5202191123ff3bfd5e | 81b73c69b19b4e45eeae7092f9c28fa5c915fb74eee9edf622d890bb40e4be14 | c1ccncc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:5](=[CH;D2;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]:[c:11])-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:5](-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15])-[CH;D3;+0:6](-[C:16]-[C;D1;H3:17])-[c:7](:[c:8]):[c:9]:[#7;a:10]:[c:11] | 55 | [{"value": 55.0, "product": "C(C)OC(C(C(=O)OCC)C(CC)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.6, "product": "C(C)OC(C(C(=O)OCC)C(CC)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 5 | MINUTE | To a stirred suspension of copper iodide (5.71 g, 30 mmol) in diethyl ether (120 mL) under argon was added ethylmagnesium bromide (3 M solution in diethyl ether, 20 mL, 20 mmol) within 10 min at 0° C. After 5 min stirring the mixture was cooled to −78° C. and a solution of 2-(6tert-butoxycarbonylamino-pyridin-3-ylmethy... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Ester.Ester | null | null | c1ccncc1 | Other | [Cu](I)I.O1CCCC1.C(C)OCC.N | -78 | 0.083333 | CCOC(=O)C(=Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OCC>[Cu](I)I.O1CCCC1.C(C)OCC.N>CCOC(=O)C(C(=O)OCC)C(CC)c1ccc(NC(=O)OC(C)(C)C)nc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-83f8b8280796475cbefda10db2bad030 | CCOC(=O)C(C(=O)OCC)C(CC)c1ccc(NC(=O)OC(C)(C)C)nc1>>CCOC(=O)C(C(=O)O)C(CC)c1ccc(NC(=O)OC(C)(C)C)nc1 | C(C)OC(C(C(=O)OCC)C(CC)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O.[OH-].[K+]>>C(C)OC(C(C(=O)O)C(CC)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O | CC[O:9][C:7]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH:10]([CH2:11][CH3:12])[c:13]1[cH:14][cH:15][c:16]([NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[n:25][cH:26]1)=[O:8]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([C:7](=[O:8])[OH:9])[CH:10]([CH2:11][CH3:12])[c:13]1[cH:14][cH:15][c:16]([NH:17][C:18](=[... | CCOC(=O)C(C(=O)OCC)C(CC)c1ccc(NC(=O)OC(C)(C)C)nc1 | CCOC(=O)C(C(=O)O)C(CC)c1ccc(NC(=O)OC(C)(C)C)nc1 | null | null | ClCCl.C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccncc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7]>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 82.3 | [{"value": 82.0, "product": "C(C)OC(C(C(=O)O)C(CC)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.3, "product": "C(C)OC(C(C(=O)O)C(CC)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | 2-[1-(6-tert-Butoxycarbonylamino-pyridin-3-yl)-propyl]-malonic acid diethyl ester (3.23 g, 8.19 mmol) was dissolved in a mixture of dichloromethane (12 mL) and ethanol (24 mL, 99.5%). To this solution was added dropwise a solution of potassium hydroxide (0.528 g, 87%, 8.20 mmol) in ethanol (16 mL, 99.5%) at 0° C. over ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccncc1 | Other | ClCCl.C(C)O | null | 16 | CCOC(=O)C(C(=O)OCC)C(CC)c1ccc(NC(=O)OC(C)(C)C)nc1>ClCCl.C(C)O>CCOC(=O)C(C(=O)O)C(CC)c1ccc(NC(=O)OC(C)(C)C)nc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8eec2afd44f04db6900dd76d091ef212 | CCOC(=O)C(CSC(C)=O)C(CC)c1ccc(NC(=O)OC(C)(C)C)nc1>>CCC(c1ccc(N)nc1)C(CS)C(=O)O | Cl.C(C)OC(C(C(CC)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)CSC(C)=O)=O>>NC1=CC=C(C=N1)C(C(C(=O)O)CS)CC | CC[O:16][C:14]([CH:11]([CH:3]([CH2:2][CH3:1])[c:4]1[cH:5][cH:6][c:7]([NH:8]C(=O)OC(C)(C)C)[n:9][cH:10]1)[CH2:12][S:13]C(C)=O)=[O:15]>>[CH3:1][CH2:2][CH:3]([c:4]1[cH:5][cH:6][c:7]([NH2:8])[n:9][cH:10]1)[CH:11]([CH2:12][SH:13])[C:14](=[O:15])[OH:16] | CCOC(=O)C(CSC(C)=O)C(CC)c1ccc(NC(=O)OC(C)(C)C)nc1 | CCC(c1ccc(N)nc1)C(CS)C(=O)O | null | null | null | Reduction | OtherReaction | df63f36502c6e187beb1211487c3f0937031934a12a3c506c12c51a17b700a31 | 9a7c4efef36aa8beb2b85c58cd3924b350f3ef529d4eb0778d927167159d9d8b | c1ccncc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].C-C-[O;H0;D2;+0:6]-[C:7](=[O;D1;H0:8])-[C:9]-[C:10]-[S;H0;D2;+0:11]-C(-C)=O>>[NH2;D1;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:8]=[C:7](-[OH;D1;+0:6])-[C:9]-[C:10]-[SH;D1;+0:11] | 97 | [{"value": 97.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Hydrochloric acid (38%, 4 mL) was added to 2-acetylsulfanylmethyl-3-(6-tert-butoxycarbonylamino-pyridin-3-yl)-pentanoic acid ethyl ester (0.041 g, 0.1 mmol) under argon and the mixture was heated to reflux for 4 h. Concentration under reduced pressure and drying (45° C., 0.3 mbar) afforded the title compound as the hyd... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ether.Carbo-thioester.Boc | Carboxylic acid.Primary amine.Aliphatic thiol | null | null | c1ccncc1 | HO- | null | null | null | CCOC(=O)C(CSC(C)=O)C(CC)c1ccc(NC(=O)OC(C)(C)C)nc1>>CCC(c1ccc(N)nc1)C(CS)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ddd52b858b564021a8ec19389258f48a | CCOC(=O)C(=Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OCC.C[CH](C)[Mg][Br]>>CCOC(=O)C(C(=O)OCC)C(c1ccc(NC(=O)OC(C)(C)C)nc1)C(C)C | [Cu](C#N)C#N.C(C)(C)[Mg]Br.[Cl-].[NH4+].C(C)OC(C(C(=O)OCC)=CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O>>C(C)OC(C(C(=O)OCC)C(C(C)C)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([C:7](=[O:8])[O:9][CH2:10][CH3:11])=[CH:12][c:13]1[cH:14][cH:15][c:16]([NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[n:25][cH:26]1.[Br][Mg][CH:27]([CH3:28])[CH3:29]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([C:7](=[O:8])[O:9][CH2:10][CH3:11])[CH:12]([c:13]1[cH:14][c... | CCOC(=O)C(=Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OCC.C[CH](C)[Mg][Br] | CCOC(=O)C(C(=O)OCC)C(c1ccc(NC(=O)OC(C)(C)C)nc1)C(C)C | null | null | O1CCCC1.N | C-C Coupling | OtherReaction | ded5de1d4b2ca635f7bb9ec5053cb3e8655a1d1ad3898f1dd5101f7a5450b06d | a3a72c9b5074527d3f1f3733953bd3ee635d84faa2f52f7cadb924c42d8b87e7 | c1ccncc1 | [Br]-[Mg]-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[C;H0;D3;+0:8](=[CH;D2;+0:9]-[c:10](:[c:11]):[c:12]:[#7;a:13]:[c:14])-[C:15](=[O;D1;H0:16])-[#8:17]-[C:18]>>[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[CH;D3;+0:8](-[C:15](=[O;D1;H0:16])-[#8:17]-[C:18])-[CH;D3;+0:9](-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D... | 67.1 | [{"value": 25.0, "product": "C(C)OC(C(C(=O)OCC)C(C(C)C)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.1, "product": "C(C)OC(C(C(=O)OCC)C(C(C)C)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a stirred solution of copper cyanide (3.58 g, 40 mmol) in tetrahydrofurane (50 mL) at −15° C. a solution of isopropylmagnesium bromide (40 mL, 2 M, 80 mmol) in tetrahydrofurane was added under argon over 15 min. After additional 15 min stirring a solution of 2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethylene)-malon... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Ester.Ester | Ester.Ester | null | null | c1ccncc1 | Br-.Mg | O1CCCC1.N | null | 16 | CCOC(=O)C(=Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OCC.C[CH](C)[Mg][Br]>O1CCCC1.N>CCOC(=O)C(C(=O)OCC)C(c1ccc(NC(=O)OC(C)(C)C)nc1)C(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-531d900b1a5549609a8857c78e89db2d | CCOC(=O)C(C(=O)OCC)C(c1ccc(NC(=O)OC(C)(C)C)nc1)C(C)C>>CCOC(=O)C(C(=O)O)C(c1ccc(NC(=O)OC(C)(C)C)nc1)C(C)C | C(C)OC(C(C(=O)OCC)C(C(C)C)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O.[OH-].[K+].O>>C(C)OC(C(C(=O)O)C(C(C)C)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O | CC[O:9][C:7]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH:10]([c:11]1[cH:12][cH:13][c:14]([NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[n:23][cH:24]1)[CH:25]([CH3:26])[CH3:27])=[O:8]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([C:7](=[O:8])[OH:9])[CH:10]([c:11]1[cH:12][cH:13][c:14]([NH:15][C:16](=[O:17])[O... | CCOC(=O)C(C(=O)OCC)C(c1ccc(NC(=O)OC(C)(C)C)nc1)C(C)C | CCOC(=O)C(C(=O)O)C(c1ccc(NC(=O)OC(C)(C)C)nc1)C(C)C | null | null | ClCCl.C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccncc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7]>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | 1 | HOUR | To a solution of 2-[1-(6-tert-butoxycarbonylamino-pyridin-3-yl)-2-methyl-propyl]-malonic acid diethyl ester (1.569 g, 3.84 mmol) in a mixture of dichloromethane (6 mL) and ethanol (12 mL, 95%) at 0° C. a solution of potassium hydroxide (0.272 g, 85%, 4.2 mmol) in ethanol (6 mL, 95%) was added dropwise over 40 min. Afte... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccncc1 | Other | ClCCl.C(C)O | null | 1 | CCOC(=O)C(C(=O)OCC)C(c1ccc(NC(=O)OC(C)(C)C)nc1)C(C)C>ClCCl.C(C)O>CCOC(=O)C(C(=O)O)C(c1ccc(NC(=O)OC(C)(C)C)nc1)C(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-97224e5d78f145d2ba09e5fb6f159889 | CCOC(=O)C(=Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OCC.[Br][Mg][c]1ccccc1>>CCOC(=O)C(C(=O)OCC)C(c1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1 | [Cl-].[NH4+].C(C)OC(C(C(=O)OCC)=CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O.[Cu]C#N.C1(=CC=CC=C1)[Mg]Br>>C(C)OC(C(C(=O)OCC)C(C1=CC=CC=C1)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([C:7](=[O:8])[O:9][CH2:10][CH3:11])=[CH:12][c:19]1[cH:20][cH:21][c:22]([NH:23][C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])[n:31][cH:32]1.[Br][Mg][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([C:7](=[O:8])[O:9][CH2:10][CH3:11])[CH:12... | CCOC(=O)C(=Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OCC.[Br][Mg][c]1ccccc1 | CCOC(=O)C(C(=O)OCC)C(c1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1 | null | null | CCCCCC.C1CCOC1 | C-C Coupling | OtherReaction | f62ef73d398b23d911bdb5bde1066963de5c42fb8ffd3c68d72c8f6ee276d537 | a3a72c9b5074527d3f1f3733953bd3ee635d84faa2f52f7cadb924c42d8b87e7 | c1ccc(Cc2cccnc2)cc1 | [Br]-[Mg]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C;H0;D3;+0:10](=[CH;D2;+0:11]-[c:12](:[c:13]):[c:14]:[#7;a:15]:[c:16])-[C:17](=[O;D1;H0:18])-[#8:19]-[C:20]>>[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[CH;D3;+0:10](-[C:17](=[O;D1;H0:18])-[#8:19]-[C:20])-[CH;D3;+0:11](-[c:12](:[c:13]):[c:14]:[#... | 88 | [{"value": 88.0, "product": "C(C)OC(C(C(=O)OCC)C(C1=CC=CC=C1)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.8, "product": "C(C)OC(C(C(=O)OCC)C(C1=CC=CC=C1)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | To a vigorously stirred suspensin of copper(I)cyanide (1.71 g, 19.06 mmol) in dry THF (18 mL) was added a solution of phenylmagnesium bromide (12.7 mL 3 M in ether, 38.11 mmol) at 0° C. under argon. The mixture was allowed to warm to room temperature, giving a dark brown solution. After 150 minutes a solution of 2-(6-t... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Ester.Ester | Ester.Ester | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccncc1 | Br-.Mg | CCCCCC.C1CCOC1 | null | 72 | CCOC(=O)C(=Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OCC.[Br][Mg][c]1ccccc1>CCCCCC.C1CCOC1>CCOC(=O)C(C(=O)OCC)C(c1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-96bd72ab02c549c9994fa9edd37dec7e | CCOC(=O)C(C(=O)OCC)C(c1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1>>CCOC(=O)C(C(=O)O)C(c1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1 | [OH-].[K+].C(C)OC(C(C(=O)OCC)C(C1=CC=CC=C1)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O.[OH-].[K+]>>C(C)OC(C(C(=O)O)C(C1=CC=CC=C1)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O | CC[O:9][C:7]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH:10]([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[c:17]1[cH:18][cH:19][c:20]([NH:21][C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[n:29][cH:30]1)=[O:8]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([C:7](=[O:8])[OH:9])[CH:10]([c:11]1[cH:12][cH:13][cH:14][cH:15... | CCOC(=O)C(C(=O)OCC)C(c1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1 | CCOC(=O)C(C(=O)O)C(c1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1 | null | null | C(Cl)Cl.C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Cc2cccnc2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7]>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 99.8 | [{"value": 98.0, "product": "C(C)OC(C(C(=O)O)C(C1=CC=CC=C1)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.8, "product": "C(C)OC(C(C(=O)O)C(C1=CC=CC=C1)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of KOH (0.266 g, 4.11 mmol) in ethanol (14 mL) was added to a solution of 2-[(6-tert-butoxycarbonylamino-pyridin-3-yl)-phenyl-methyl]-malonic acid diethyl ester (1.82 g, 4.11 mmol) in ethanol (12 mL) and methylene chloride (13 mL) at 0° C. The mixture was stirred overnight at room temperature. More KOH (80 m... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccncc1 | Other | C(Cl)Cl.C(C)O | null | 8 | CCOC(=O)C(C(=O)OCC)C(c1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1>C(Cl)Cl.C(C)O>CCOC(=O)C(C(=O)O)C(c1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-af4686a75b474273b708218cdf042d3f | CCOC(=O)C(C(=O)O)C(c1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1>>C=C(C(=O)OCC)C(c1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1 | C(C)NCC.C(C)OC(C(C(=O)O)C(C1=CC=CC=C1)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O.C=O>>C(C)OC(C(=C)C(C1=CC=CC=C1)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O | O=[C:1](O)[CH:2]([C:3](=[O:4])[O:5][CH2:6][CH3:7])[CH:8]([c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[c:15]1[cH:16][cH:17][c:18]([NH:19][C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[n:27][cH:28]1>>[CH2:1]=[C:2]([C:3](=[O:4])[O:5][CH2:6][CH3:7])[CH:8]([c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[c:15]1[cH:16][c... | CCOC(=O)C(C(=O)O)C(c1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1 | C=C(C(=O)OCC)C(c1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1 | null | null | C(Cl)Cl.C(C)(=O)OCC | Miscellaneous | OtherReaction | 485594ce7bba157615ffbb01ccede84a4e638576571b5d04649a06f3d4b7bce0 | 55e5b5078322f9f4fb0a7e9b5fc8a8cb9084e9135b447b8c441ad0800765792e | c1ccc(Cc2cccnc2)cc1 | O-[C;H0;D3;+0:1](=O)-[CH;D3;+0:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[C:7](-[c:8])-[c:9]:[c:10]:[#7;a:11]>>[#7;a:11]:[c:10]:[c:9]-[C:7](-[c:8])-[C;H0;D3;+0:2](=[CH2;D1;+0:1])-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6] | 23 | [{"value": 23.0, "product": "C(C)OC(C(=C)C(C1=CC=CC=C1)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 23.0, "product": "C(C)OC(C(=C)C(C1=CC=CC=C1)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Diethylamine (0.52 mL, 5.04 mmol) was added to a mixture of 2-[(6-tert-butoxycarbonylamino-pyridin-3-yl)-phenyl-methyl]-malonic acid monoethyl ester (1.7 g, 4.1 mmol) and 37% aq. solution of formaldehyde (0.42 mL, 5.6 mmol) in methylene chloride (6.5 mL) at 0° C. The mixture was stirred overnight at room temperature an... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester | Ester.Vinyl | null | null | c1ccccc1.c1ccncc1 | Other | C(Cl)Cl.C(C)(=O)OCC | null | 8 | CCOC(=O)C(C(=O)O)C(c1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1>C(Cl)Cl.C(C)(=O)OCC>C=C(C(=O)OCC)C(c1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7ff9aa4d50ed477f91ea9ca5941afd61 | C=C(C(=O)OCC)C(c1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1.CC(O)=S>>CCOC(=O)C(CSC(C)=O)C(c1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1 | C(C)N(CC)CC.C(C)OC(C(=C)C(C1=CC=CC=C1)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O.C(C)(=S)O.C(C)(=O)OCC>>C(C)OC(C(C(C1=CC=CC=C1)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)CSC(C)=O)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH2:7])[CH:12]([c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[c:19]1[cH:20][cH:21][c:22]([NH:23][C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])[n:31][cH:32]1.[S:8]=[C:9]([CH3:10])[OH:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][S:8][C:9]([CH3:10])=[O:11])[CH:12]([c:... | C=C(C(=O)OCC)C(c1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1.CC(O)=S | CCOC(=O)C(CSC(C)=O)C(c1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1 | null | null | null | Protection | OtherReaction | 56aa090d67fbecbea8a1963579cc34949775a09653b2b2f2795c609c60e70c77 | 5a9b0d631147b21b844b3c73866d1d81ab543538a176ebae28118ae7e39e572f | c1ccc(Cc2cccnc2)cc1 | [#7;a:1]:[c:2]:[c:3]-[C:4](-[c:5])-[C;H0;D3;+0:6](=[CH2;D1;+0:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11].[C;D1;H3:12]-[C;H0;D3;+0:13](-[OH;D1;+0:14])=[S;H0;D1;+0:15]>>[#7;a:1]:[c:2]:[c:3]-[C:4](-[c:5])-[CH;D3;+0:6](-[CH2;D2;+0:7]-[S;H0;D2;+0:15]-[C;H0;D3;+0:13](-[C;D1;H3:12])=[O;H0;D1;+0:14])-[C:8](=[O;D1;H0:9])-[#8:10]-[C... | 73 | [{"value": 73.0, "product": "C(C)OC(C(C(C1=CC=CC=C1)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)CSC(C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | 45 | CELSIUS | null | null | Triethylamine (0.105 g, 1.04 mmol) was added to a solution of 2-[(6tert-butoxycarbonylamino-pyridin-3-yl)-phenyl-methyl]-acrylic acid ethyl ester (0.36 g, 0.94 mmol) in thioacetic acid (4 mL) at 0° C. under argon. The mixture was heated at 45° C. for 24 h. Ethyl acetate was added and the organic phase was washed with a... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Thiocarbonyl.Vinyl | Ester.Carbo-thioester | null | null | c1ccccc1.c1ccncc1 | null | null | 45 | null | C=C(C(=O)OCC)C(c1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1.CC(O)=S>>CCOC(=O)C(CSC(C)=O)C(c1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-17582d8f0b60422395c84343561351ad | CCOC(=O)C(CSC(C)=O)C(c1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1>>Nc1ccc(C(c2ccccc2)C(CS)C(=O)O)cn1 | C(C)OC(C(C(C1=CC=CC=C1)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)CSC(C)=O)=O>>NC1=CC=C(C=N1)C(C(C(=O)O)CS)C1=CC=CC=C1 | CC[O:18][C:16]([CH:13]([CH:6]([c:5]1[cH:4][cH:3][c:2]([NH:1]C(=O)OC(C)(C)C)[n:20][cH:19]1)[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[CH2:14][S:15]C(C)=O)=[O:17]>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[CH:13]([CH2:14][SH:15])[C:16](=[O:17])[OH:18])[cH:19][n:20]1 | CCOC(=O)C(CSC(C)=O)C(c1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1 | Nc1ccc(C(c2ccccc2)C(CS)C(=O)O)cn1 | null | null | Cl | Reduction | OtherReaction | df63f36502c6e187beb1211487c3f0937031934a12a3c506c12c51a17b700a31 | 9a7c4efef36aa8beb2b85c58cd3924b350f3ef529d4eb0778d927167159d9d8b | c1ccc(Cc2cccnc2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].C-C-[O;H0;D2;+0:6]-[C:7](=[O;D1;H0:8])-[C:9]-[C:10]-[S;H0;D2;+0:11]-C(-C)=O>>[NH2;D1;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:8]=[C:7](-[OH;D1;+0:6])-[C:9]-[C:10]-[SH;D1;+0:11] | 100 | [{"value": 100.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Acetylsulfanylmethyl-3-(6-tert-butoxycarbonylamino-pyridin-3-yl )-3-phenyl-propionic acid ethyl ester (58 mg, 0.125 mmol) was dissolved in conc. HCl (3.0 mL). The solution was heated to reflux for 130 min under argon. Concentration under reduced pressure gave the title compound as the hydrochloride salt (41 mg, 100%)... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ether.Carbo-thioester.Boc | Carboxylic acid.Primary amine.Aliphatic thiol | null | null | c1ccncc1.c1ccccc1 | HO- | Cl | null | null | CCOC(=O)C(CSC(C)=O)C(c1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1>Cl>Nc1ccc(C(c2ccccc2)C(CS)C(=O)O)cn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ff12d0482cde4b349653c5c5b90cce46 | CCOC(=O)C(=Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OCC.[Br][Mg][CH2]c1ccccc1>>CCOC(=O)C(C(=O)OCC)C(Cc1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1 | [Cl-].[NH4+].C(C)OC(C(C(=O)OCC)=CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O.[Cu]C#N.C(C1=CC=CC=C1)[Mg]Br>>C(C)OC(C(C(=O)OCC)C(CC1=CC=CC=C1)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([C:7](=[O:8])[O:9][CH2:10][CH3:11])=[CH:12][c:20]1[cH:21][cH:22][c:23]([NH:24][C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[n:32][cH:33]1.[Br][Mg][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([C:7](=[O:8])[O:9][CH2:10][CH3:11... | CCOC(=O)C(=Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OCC.[Br][Mg][CH2]c1ccccc1 | CCOC(=O)C(C(=O)OCC)C(Cc1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | ded5de1d4b2ca635f7bb9ec5053cb3e8655a1d1ad3898f1dd5101f7a5450b06d | a3a72c9b5074527d3f1f3733953bd3ee635d84faa2f52f7cadb924c42d8b87e7 | c1ccc(CCc2cccnc2)cc1 | [Br]-[Mg]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C;H0;D3;+0:9](=[CH;D2;+0:10]-[c:11](:[c:12]):[c:13]:[#7;a:14]:[c:15])-[C:16](=[O;D1;H0:17])-[#8:18]-[C:19]>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH;D3;+0:9](-[C:16](=[O;D1;H0:17])-[#8:18]-[C:19])-[CH;D3;+0:10](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])... | 53 | [{"value": 53.0, "product": "C(C)OC(C(C(=O)OCC)C(CC1=CC=CC=C1)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.7, "product": "C(C)OC(C(C(=O)OCC)C(CC1=CC=CC=C1)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a vigorously stirred suspensin of copper(I)cyanide (0.66 g, 7.32 mmol) in dry THF (5 mL) was added a solution of benzylmagnesium bromide (5 mL 2.93 M in ether, 14.64 mmol) at 0° C. under argon. The mixture was allowed to warm to room temperature, giving a dark brown solution. After 60 minutes a solution of 2-(6-tert... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Ester.Ester | Ester.Ester | null | null | c1ccccc1.c1ccncc1 | Br-.Mg | C1CCOC1 | null | 8 | CCOC(=O)C(=Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OCC.[Br][Mg][CH2]c1ccccc1>C1CCOC1>CCOC(=O)C(C(=O)OCC)C(Cc1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f601510239bb4196bfecd8efb5551d09 | CCOC(=O)C(C(=O)OCC)C(Cc1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1>>CCOC(=O)C(C(=O)O)C(Cc1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1 | [OH-].[K+].C(C)OC(C(C(=O)OCC)C(CC1=CC=CC=C1)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O>>C(C)OC(C(C(=O)O)C(CC1=CC=CC=C1)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O | CC[O:9][C:7]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH:10]([CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[c:18]1[cH:19][cH:20][c:21]([NH:22][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[n:30][cH:31]1)=[O:8]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([C:7](=[O:8])[OH:9])[CH:10]([CH2:11][c:12]1[cH:13][cH:... | CCOC(=O)C(C(=O)OCC)C(Cc1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1 | CCOC(=O)C(C(=O)O)C(Cc1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1 | null | null | C(Cl)Cl.C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(CCc2cccnc2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7]>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 90 | [{"value": 90.0, "product": "C(C)OC(C(C(=O)O)C(CC1=CC=CC=C1)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | A solution of KOH (0.067 g, 1.03 mmol) in ethanol (3 mL) was added to a solution of 2-[1-(6-tert-butoxycarbonylamino-pyridin-3-yl)-2-phenyl-ethyl]-malonic acid diethyl ester (0.44g, 0.96 mmol) in ethanol (3 mL) and methylene chloride (2 mL) at 0° C. The mixture was stirred for 48 h at room temperature. The mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccncc1 | Other | C(Cl)Cl.C(C)O | null | 48 | CCOC(=O)C(C(=O)OCC)C(Cc1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1>C(Cl)Cl.C(C)O>CCOC(=O)C(C(=O)O)C(Cc1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1f4ca76aef404411a3eb336929b17465 | C=C(C(=O)OCC)C(Cc1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1.CC(O)=S>>CCOC(=O)C(CSC(C)=O)C(Cc1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1 | C(C)N(CC)CC.C(C)OC(C(=C)C(CC1=CC=CC=C1)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O.C(C)(=S)O.C(C)(=O)OCC>>C(C)OC(C(C(CC1=CC=CC=C1)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)CSC(C)=O)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH2:7])[CH:12]([CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)[c:20]1[cH:21][cH:22][c:23]([NH:24][C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[n:32][cH:33]1.[S:8]=[C:9]([CH3:10])[OH:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][S:8][C:9]([CH3:10])=[O:11])[CH... | C=C(C(=O)OCC)C(Cc1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1.CC(O)=S | CCOC(=O)C(CSC(C)=O)C(Cc1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1 | null | null | null | Protection | OtherReaction | 56aa090d67fbecbea8a1963579cc34949775a09653b2b2f2795c609c60e70c77 | 5a9b0d631147b21b844b3c73866d1d81ab543538a176ebae28118ae7e39e572f | c1ccc(CCc2cccnc2)cc1 | [#7;a:1]:[c:2]:[c:3]-[C:4](-[C:5])-[C;H0;D3;+0:6](=[CH2;D1;+0:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11].[C;D1;H3:12]-[C;H0;D3;+0:13](-[OH;D1;+0:14])=[S;H0;D1;+0:15]>>[#7;a:1]:[c:2]:[c:3]-[C:4](-[C:5])-[CH;D3;+0:6](-[CH2;D2;+0:7]-[S;H0;D2;+0:15]-[C;H0;D3;+0:13](-[C;D1;H3:12])=[O;H0;D1;+0:14])-[C:8](=[O;D1;H0:9])-[#8:10]-[C... | 65 | [{"value": 65.0, "product": "C(C)OC(C(C(CC1=CC=CC=C1)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)CSC(C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | 45 | CELSIUS | null | null | Triethylamine (0.096 g, 0.95 mmol) was added to a solution of 2-[1-(6-tert-butoxycarbonylamino-pyridin-3-yl)-2-phenyl-ethyl]-acrylic acid ethyl ester (0.34 g, 0.86 mmol) in thioacetic acid (3.5 mL) at 0° C. under argon. The mixture was heated at 45° C. for 24 h. Ethyl acetate was added and the organic phase was washed ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Thiocarbonyl.Vinyl | Ester.Carbo-thioester | null | null | c1ccccc1.c1ccncc1 | null | null | 45 | null | C=C(C(=O)OCC)C(Cc1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1.CC(O)=S>>CCOC(=O)C(CSC(C)=O)C(Cc1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1cfb6a7fe4ee45cf909ed85a4f33fcad | CCOC(=O)C(CSC(C)=O)C(Cc1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1>>Nc1ccc(C(Cc2ccccc2)C(CS)C(=O)O)cn1 | C(C)OC(C(C(CC1=CC=CC=C1)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)CSC(C)=O)=O>>NC1=CC=C(C=N1)C(C(C(=O)O)CS)CC1=CC=CC=C1 | CC[O:19][C:17]([CH:14]([CH:6]([c:5]1[cH:4][cH:3][c:2]([NH:1]C(=O)OC(C)(C)C)[n:21][cH:20]1)[CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[CH2:15][S:16]C(C)=O)=[O:18]>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[CH:14]([CH2:15][SH:16])[C:17](=[O:18])[OH:19])[cH:20][n:21]1 | CCOC(=O)C(CSC(C)=O)C(Cc1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1 | Nc1ccc(C(Cc2ccccc2)C(CS)C(=O)O)cn1 | null | null | Cl | Reduction | OtherReaction | df63f36502c6e187beb1211487c3f0937031934a12a3c506c12c51a17b700a31 | 9a7c4efef36aa8beb2b85c58cd3924b350f3ef529d4eb0778d927167159d9d8b | c1ccc(CCc2cccnc2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].C-C-[O;H0;D2;+0:6]-[C:7](=[O;D1;H0:8])-[C:9]-[C:10]-[S;H0;D2;+0:11]-C(-C)=O>>[NH2;D1;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:8]=[C:7](-[OH;D1;+0:6])-[C:9]-[C:10]-[SH;D1;+0:11] | 98 | [{"value": 98.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Acetylsulfanylmethyl-3-(6-tert-butoxycarbonylamino-pyridin-3-yl)4-phenyl-butyric acid ethyl ester (0.14 g, 0.3 mmol) was dissolved in conc. HCl (5.0 mL). The solution was heated to reflux for 4.5 h under argon. Concentration under reduced pressure gave the title compound as the hydrochloride salt (100 mg, 98%).
Condi... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ether.Carbo-thioester.Boc | Carboxylic acid.Primary amine.Aliphatic thiol | null | null | c1ccncc1.c1ccccc1 | HO- | Cl | null | null | CCOC(=O)C(CSC(C)=O)C(Cc1ccccc1)c1ccc(NC(=O)OC(C)(C)C)nc1>Cl>Nc1ccc(C(Cc2ccccc2)C(CS)C(=O)O)cn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-71bc195e21be47959f97fd32b2c63057 | CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(CCc1ccccc1)SC(C)=O>>Nc1ccc(CC(C(=O)O)C(S)CCc2ccccc2)cn1 | C(C)(=O)SC(C(C(=O)OCC)CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)CCC1=CC=CC=C1>>NC1=CC=C(C=N1)CC(C(=O)O)C(CCC1=CC=CC=C1)S | CC[O:10][C:8]([CH:7]([CH2:6][c:5]1[cH:4][cH:3][c:2]([NH:1]C(=O)OC(C)(C)C)[n:22][cH:21]1)[CH:11]([S:12]C(C)=O)[CH2:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)=[O:9]>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH:7]([C:8](=[O:9])[OH:10])[CH:11]([SH:12])[CH2:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[... | CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(CCc1ccccc1)SC(C)=O | Nc1ccc(CC(C(=O)O)C(S)CCc2ccccc2)cn1 | null | null | Cl | Reduction | OtherReaction | df63f36502c6e187beb1211487c3f0937031934a12a3c506c12c51a17b700a31 | 9a7c4efef36aa8beb2b85c58cd3924b350f3ef529d4eb0778d927167159d9d8b | c1ccc(CCCCCc2cccnc2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].C-C-[O;H0;D2;+0:6]-[C:7](=[O;D1;H0:8])-[C:9]-[C:10](-[C:11])-[S;H0;D2;+0:12]-C(-C)=O>>[C:11]-[C:10](-[SH;D1;+0:12])-[C:9]-[C:7](=[O;D1;H0:8])-[OH;D1;+0:6].[NH2;D1;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | 98 | [{"value": 98.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Ethyl 3-(acetylsulfanyl)-2-({6-[(tert-butoxycarbonyl)amino]-3-pyridinyl}methyl)-5-phenylpentanoate (9 mg, 18.5 μmol) was dissolved in conc. HCl (1 mL) under argon. The solution was heated to reflux for 4.5 h. Concentration under reduced pressure yielded the title compound as the hydrochloride salt (6.4 mg, 98%) as a di... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ether.Carbo-thioester.Boc | Carboxylic acid.Primary amine.Aliphatic thiol | null | null | c1ccncc1.c1ccccc1 | HO- | Cl | null | null | CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(CCc1ccccc1)SC(C)=O>Cl>Nc1ccc(CC(C(=O)O)C(S)CCc2ccccc2)cn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d892903084fa44d4a6cbbfbe8d170525 | CCOC(=O)C(CSC(C)=O)Cc1ccc(NC(=O)OC(C)(C)C)nc1>>CCOC(=O)C(CSSCC(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OCC)Cc1ccc(NC(=O)OC(C)(C)C)nc1 | C(C)OC(C(CSC(C)=O)CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O>>C(C)OC(C(CSSCC(CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)C(=O)OCC)CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O | [CH3:1][C:21]([O:20][C:18]([NH:17][c:16]1[cH:15][cH:14][c:13]([CH2:12][CH:11]([CH2:10][S:8][C:7](=[O:3])[CH3:6])[C:27](=[O:28])[O:29][CH2:30][CH3:31])[cH:26][n:25]1)=[O:19])([CH3:44])[CH3:46]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][S:8][S:9][CH2:10][CH:11]([CH2:12][c:13]1[cH:14][cH:15][c:16]([NH:17][C:18](=[O:1... | CCOC(=O)C(CSC(C)=O)Cc1ccc(NC(=O)OC(C)(C)C)nc1 | CCOC(=O)C(CSSCC(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OCC)Cc1ccc(NC(=O)OC(C)(C)C)nc1 | null | null | N.C(C)O | Aromatic Heterocycle Formation | OtherReaction | f51249a6ca6aaf9e7fb879c7f314cb9d7ab9a38383a2907a4b02eb9292a80fd9 | c22b949ae843194c3f276d513a86e11389e124517503f4146b378302562b0caa | c1cncc(CCCSSCCCc2cccnc2)c1 | [#7:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;H0;D4;+0:5](-[CH3;D1;+0:6])(-[CH3;D1;+0:7])-[CH3;D1;+0:8].[C:9]-[C:10](-[CH2;D2;+0:11]-[S;H0;D2;+0:12]-[C;H0;D3;+0:13](-[CH3;D1;+0:14])=[O;H0;D1;+0:15])-[C:16](=[O;D1;H0:17])-[#8:18]-[C:19]>>[#7:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;H0;D4;+0:5](-[C;D1;H3:20])(-[C;D1;H3:21])-[C;D1;H3:22].... | 98 | [{"value": 98.0, "product": "C(C)OC(C(CSSCC(CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)C(=O)OCC)CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.7, "product": "C(C)OC(C(CSSCC(CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)C(=O)OCC)CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD",... | null | null | 160 | MINUTE | 3-Acetylsulfanyl-2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-propionic acid ethyl ester (150 mg, 0.392 mmol) was dissolved in ethanol (15 mL) saturated with NH3 (g). After stirring for 160 min., the mixture was concentrated under reduced pressure. The residue was dissolved in EtOH (10 mL) whereafter a solution of... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Carbo-thioester.Boc | Carbamic ester.Ester.Ether.Ether.Disulfide.Boc.Boc | null | c1ccncc1 | c1ccncc1.c1ccncc1 | Other | N.C(C)O | null | 2.666667 | CCOC(=O)C(CSC(C)=O)Cc1ccc(NC(=O)OC(C)(C)C)nc1>N.C(C)O>CCOC(=O)C(CSSCC(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OCC)Cc1ccc(NC(=O)OC(C)(C)C)nc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-72e6ad47645f40be8af30f229f1b433d | CCOC(=O)C(CSSCC(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OCC)Cc1ccc(NC(=O)OC(C)(C)C)nc1>>CCOC(=O)C(CSSCC(Cc1ccc(N)nc1)C(=O)OCC)Cc1ccc(N)nc1 | Cl.C(C)OC(C(CSSCC(CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)C(=O)OCC)CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O>>C(C)OC(C(CSSCC(CC=1C=NC(=CC1)N)C(=O)OCC)CC=1C=NC(=CC1)N)=O | CC(C)(C)OC(=O)[NH:17][c:16]1[cH:15][cH:14][c:13]([CH2:12][CH:11]([CH2:10][S:9][S:8][CH2:7][CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:25][c:26]2[cH:27][cH:28][c:29]([NH:30]C(=O)OC(C)(C)C)[n:31][cH:32]2)[C:20](=[O:21])[O:22][CH2:23][CH3:24])[cH:19][n:18]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][S:8][S:9][CH2:10... | CCOC(=O)C(CSSCC(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OCC)Cc1ccc(NC(=O)OC(C)(C)C)nc1 | CCOC(=O)C(CSSCC(Cc1ccc(N)nc1)C(=O)OCC)Cc1ccc(N)nc1 | null | null | C(C)OC(C)=O | Reduction | OtherReaction | 46afa823531eb720870dfe550968a278ca78b2d48230eadae217f678fe9f4703 | ca6ddca0ebc9d1ff371f32035a46f1304744e0bd3993a09d469e1a625d8e0ac3 | c1cncc(CCCSSCCCc2cccnc2)c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10] | 98.4 | [{"value": 98.0, "product": "C(C)OC(C(CSSCC(CC=1C=NC(=CC1)N)C(=O)OCC)CC=1C=NC(=CC1)N)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.4, "product": "C(C)OC(C(CSSCC(CC=1C=NC(=CC1)N)C(=O)OCC)CC=1C=NC(=CC1)N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 19 | HOUR | Etylacetate saturated with HCl (g) (15 mL) was added to a solution of 3-[3-(6tert-butoxycarbonylamino-pyridin-3-yl)-2-ethoxycarbonyl-propyldisulfanyl]-2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-propionic acid ethyl ester (130 mg, 0.191 mmol) in ethylacetate (7 mL) at 0° C. The reaction was allowed to attain room... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carbamic ester.Ether.Ether.Boc.Boc | Primary amine.Primary amine | null | null | c1ccncc1.c1ccncc1 | HO- | C(C)OC(C)=O | null | 19 | CCOC(=O)C(CSSCC(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OCC)Cc1ccc(NC(=O)OC(C)(C)C)nc1>C(C)OC(C)=O>CCOC(=O)C(CSSCC(Cc1ccc(N)nc1)C(=O)OCC)Cc1ccc(N)nc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0b93bfa366994cbcb9be4fd35009ee6f | CC(C)(C)C(=O)Nc1ccc(Br)cn1.CCCC(=O)N(C)OC>>CCCC(=O)c1ccc(NC(=O)C(C)(C)C)nc1 | Cl.BrC=1C=CC(=NC1)NC(C(C)(C)C)=O.C(CCC)[Li].C(O)([O-])=O.[Na+].CON(C(CCC)=O)C>>C(CCC)(=O)C=1C=CC(=NC1)NC(C(C)(C)C)=O | Br[c:6]1[cH:7][cH:8][c:9]([NH:10][C:11](=[O:12])[C:13]([CH3:14])([CH3:15])[CH3:16])[n:17][cH:18]1.CON(C)[C:4]([CH2:3][CH2:2][CH3:1])=[O:5]>>[CH3:1][CH2:2][CH2:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([NH:10][C:11](=[O:12])[C:13]([CH3:14])([CH3:15])[CH3:16])[n:17][cH:18]1 | CC(C)(C)C(=O)Nc1ccc(Br)cn1.CCCC(=O)N(C)OC | CCCC(=O)c1ccc(NC(=O)C(C)(C)C)nc1 | null | null | C(C)OCC | C-C Coupling | OtherReaction | aeedefb516da447a7938cf0e8e86abd66c9a6aa8bd6688105f56ff15f4aef307 | 7d9aa59f8ecc532475d910f9ab122332ecbb7f9444a37371b7c1bac80798d342 | c1ccncc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.C-O-N(-C)-[C;H0;D3;+0:7](=[O;D1;H0:8])-[C:9]-[C:10]>>[C:10]-[C:9]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1 | 71.6 | [{"value": 71.0, "product": "C(CCC)(=O)C=1C=CC(=NC1)NC(C(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.6, "product": "C(CCC)(=O)C=1C=CC(=NC1)NC(C(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 45 | MINUTE | A solution of N-(5-bromopyridin-2-yl)-2,2-dimethyl-propionamide (3.582 g, 13.9 mmol) in diethyl ether (36 mL) was cooled to −78° C. under argon and n-butyllithium (1.6 M, 19 mL, 30.4 mmol) was added dropwise within 20 min. 5 min after complete addition the mixture was allowed to warm up to 0° C. N-Methoxy-N-methyl buty... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amide | Ketone | c1ccncc1 | c1ccncc1 | c1ccncc1 | HBr | C(C)OCC | 0 | 0.75 | CC(C)(C)C(=O)Nc1ccc(Br)cn1.CCCC(=O)N(C)OC>C(C)OCC>CCCC(=O)c1ccc(NC(=O)C(C)(C)C)nc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8bbed489c50749129939c6d97a7a2daf | CCCC(=O)c1ccc(NC(=O)C(C)(C)C)nc1>>CCCC(O)c1ccc(NC(=O)C(C)(C)C)nc1 | C(CCC)(=O)C=1C=CC(=NC1)NC(C(C)(C)C)=O.C(C)O.Cl>>OC(CCC)C=1C=CC(=NC1)NC(C(C)(C)C)=O | [CH3:1][CH2:2][CH2:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([NH:10][C:11](=[O:12])[C:13]([CH3:14])([CH3:15])[CH3:16])[n:17][cH:18]1>>[CH3:1][CH2:2][CH2:3][CH:4]([OH:5])[c:6]1[cH:7][cH:8][c:9]([NH:10][C:11](=[O:12])[C:13]([CH3:14])([CH3:15])[CH3:16])[n:17][cH:18]1 | CCCC(=O)c1ccc(NC(=O)C(C)(C)C)nc1 | CCCC(O)c1ccc(NC(=O)C(C)(C)C)nc1 | null | null | null | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccncc1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[c:5](:[c:6]):[c:7]:[#7;a:8]:[c:9]>>[C:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[c:5](:[c:6]):[c:7]:[#7;a:8]:[c:9] | 41.2 | [{"value": 41.0, "product": "OC(CCC)C=1C=CC(=NC1)NC(C(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 41.2, "product": "OC(CCC)C=1C=CC(=NC1)NC(C(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 40 | MINUTE | To a solution of N-(5-butyryl-pyridin-2-yl)-2,2-dimethyl-propionamide (2.47 g, 9.95 mmol) in ethanol (20 mL) sodium borohydride (185 mg, 5.0 mmol) was added. After 40 min stirring at room temperature the mixture was acidified with 1 N hydrochloric acid to pH 2 and stirred for 10 min. After neutralisation with sodium hy... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1ccncc1 | null | null | null | 0.666667 | CCCC(=O)c1ccc(NC(=O)C(C)(C)C)nc1>>CCCC(O)c1ccc(NC(=O)C(C)(C)C)nc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ab020df43bc749e3bbf89b8e358a001a | CCCC(O)c1ccc(NC(=O)C(C)(C)C)nc1.ClC(Cl)Cl>>CCCC(Cl)c1ccc(NC(=O)C(C)(C)C)nc1.Cl | OC(CCC)C=1C=CC(=NC1)NC(C(C)(C)C)=O.ClC(Cl)Cl>>Cl.ClC(CCC)C=1C=CC(=NC1)NC(C(C)(C)C)=O | O[CH:4]([CH2:3][CH2:2][CH3:1])[c:6]1[cH:7][cH:8][c:9]([NH:10][C:11](=[O:12])[C:13]([CH3:14])([CH3:15])[CH3:16])[n:17][cH:18]1.ClC([Cl:5])[Cl:19]>>[CH3:1][CH2:2][CH2:3][CH:4]([Cl:5])[c:6]1[cH:7][cH:8][c:9]([NH:10][C:11](=[O:12])[C:13]([CH3:14])([CH3:15])[CH3:16])[n:17][cH:18]1.[ClH:19] | CCCC(O)c1ccc(NC(=O)C(C)(C)C)nc1.ClC(Cl)Cl | CCCC(Cl)c1ccc(NC(=O)C(C)(C)C)nc1.Cl | null | null | S(=O)(Cl)Cl | Functional Group Interconversion | Alcohol to chloride_CHCl3 | 21a2cf65174465e5d66ce487d21cbd5d0779ed9e669efc78d92c0c58648032a9 | fbe33b9c7b8cf82c00b21d6367c8b006fc874ec83ccdb0a0e6af1a5f630000b7 | c1ccncc1 | Cl-C(-[Cl;H0;D1;+0:1])-[Cl;H0;D1;+0:2].O-[CH;D3;+0:3](-[C:4]-[C:5])-[c:6](:[c:7]):[c:8]:[#7;a:9]:[c:10]>>[C:5]-[C:4]-[CH;D3;+0:3](-[Cl;H0;D1;+0:2])-[c:6](:[c:7]):[c:8]:[#7;a:9]:[c:10].[ClH;D0;+0:1] | null | [] | 55 | CELSIUS | null | null | To a solution of N-[5-(1-hydroxy-butyl)-pyridin-2-yl]-2,2-dimethyl-propionamide (1.025 g, 4.09 mmol) in trichloromethane (12 mL), thionylchloride (6 mL) was added and the mixture was heated to 55° C. for 1 h. Then the solution was concentrated under reduced pressure to leave crude N-[5-(1-chloro-butyl)-pyridin-2-yl]-2,... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary halide.Secondary halide.Secondary alcohol | Secondary halide | null | null | c1ccncc1 | HCl | S(=O)(Cl)Cl | 55 | null | CCCC(O)c1ccc(NC(=O)C(C)(C)C)nc1.ClC(Cl)Cl>S(=O)(Cl)Cl>CCCC(Cl)c1ccc(NC(=O)C(C)(C)C)nc1.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f22ffc0d44394ac888688756a345b4ba | CCCC(c1ccc(NC(=O)C(C)(C)C)nc1)C(C(=O)OCC)C(=O)OCC>>CCCC(c1ccc(NC(=O)C(C)(C)C)nc1)C(C(=O)O)C(=O)OCC | O.C(C)OC(C(C(=O)OCC)C(CCC)C=1C=NC(=CC1)NC(C(C)(C)C)=O)=O.[OH-].[K+]>>C(C)OC(C(C(=O)O)C(CCC)C=1C=NC(=CC1)NC(C(C)(C)C)=O)=O | CC[O:21][C:19]([CH:18]([CH:4]([CH2:3][CH2:2][CH3:1])[c:5]1[cH:6][cH:7][c:8]([NH:9][C:10](=[O:11])[C:12]([CH3:13])([CH3:14])[CH3:15])[n:16][cH:17]1)[C:22](=[O:23])[O:24][CH2:25][CH3:26])=[O:20]>>[CH3:1][CH2:2][CH2:3][CH:4]([c:5]1[cH:6][cH:7][c:8]([NH:9][C:10](=[O:11])[C:12]([CH3:13])([CH3:14])[CH3:15])[n:16][cH:17]1)[CH... | CCCC(c1ccc(NC(=O)C(C)(C)C)nc1)C(C(=O)OCC)C(=O)OCC | CCCC(c1ccc(NC(=O)C(C)(C)C)nc1)C(C(=O)O)C(=O)OCC | null | null | ClCCl.[Cl-].[Na+].O.C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccncc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7]>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 41 | [{"value": 41.0, "product": "C(C)OC(C(C(=O)O)C(CCC)C=1C=NC(=CC1)NC(C(C)(C)C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | This crude 2-{1-[6-(2,2-dimethyl-propionylamino)-pyridin-3-yl]-butyl}-malonic acid diethyl ester was dissolved in a mixture of dichloromethane (2.5 mL) and ethanol (5 mL) at 0° C. and a solution of potassium hydroxide (87%, 111 mg, 5.4 mmol) in ethanol (4 mL) was added. The mixture was allowed to warm up slowly to room... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccncc1 | Other | ClCCl.[Cl-].[Na+].O.C(C)O | null | 24 | CCCC(c1ccc(NC(=O)C(C)(C)C)nc1)C(C(=O)OCC)C(=O)OCC>ClCCl.[Cl-].[Na+].O.C(C)O>CCCC(c1ccc(NC(=O)C(C)(C)C)nc1)C(C(=O)O)C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7e95140ca4c5406b80a15afc1355eca2 | CCCC(c1ccc(NC(=O)C(C)(C)C)nc1)C(C(=O)O)C(=O)OCC>>C=C(C(=O)OCC)C(CCC)c1ccc(NC(=O)C(C)(C)C)nc1 | N1CCCCC1.C(C)OC(C(C(=O)O)C(CCC)C=1C=NC(=CC1)NC(C(C)(C)C)=O)=O.C=O>>C(C)OC(C(=C)C(CCC)C=1C=NC(=CC1)NC(C(C)(C)C)=O)=O | O=[C:1](O)[CH:2]([C:3](=[O:4])[O:5][CH2:6][CH3:7])[CH:8]([CH2:9][CH2:10][CH3:11])[c:12]1[cH:13][cH:14][c:15]([NH:16][C:17](=[O:18])[C:19]([CH3:20])([CH3:21])[CH3:22])[n:23][cH:24]1>>[CH2:1]=[C:2]([C:3](=[O:4])[O:5][CH2:6][CH3:7])[CH:8]([CH2:9][CH2:10][CH3:11])[c:12]1[cH:13][cH:14][c:15]([NH:16][C:17](=[O:18])[C:19]([CH... | CCCC(c1ccc(NC(=O)C(C)(C)C)nc1)C(C(=O)O)C(=O)OCC | C=C(C(=O)OCC)C(CCC)c1ccc(NC(=O)C(C)(C)C)nc1 | null | null | C1CCOC1 | Miscellaneous | OtherReaction | 485594ce7bba157615ffbb01ccede84a4e638576571b5d04649a06f3d4b7bce0 | 55e5b5078322f9f4fb0a7e9b5fc8a8cb9084e9135b447b8c441ad0800765792e | c1ccncc1 | O-[C;H0;D3;+0:1](=O)-[CH;D3;+0:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[C:7](-[C:8])-[c:9]:[c:10]:[#7;a:11]>>[#7;a:11]:[c:10]:[c:9]-[C:7](-[C:8])-[C;H0;D3;+0:2](=[CH2;D1;+0:1])-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6] | 85 | [{"value": 85.0, "product": "C(C)OC(C(=C)C(CCC)C=1C=NC(=CC1)NC(C(C)(C)C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.8, "product": "C(C)OC(C(=C)C(CCC)C=1C=NC(=CC1)NC(C(C)(C)C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a solution of 2-{1-[6-(2,2-dimethyl-propionylamino)-pyridin-3-yl]-butyl}-malonic acid monoethyl ester (712 mg, 1.95 mmol) in THF (6.5 mL) at 0° C. formaldehyde (37% in water, 0.3 mL) was added within 5 min. Stirring was continued for 10 min, then piperidine (0.26 mL, 2.63 mmol) was added dropwise within 10 min. The ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester | Ester.Vinyl | null | null | c1ccncc1 | Other | C1CCOC1 | null | 0.166667 | CCCC(c1ccc(NC(=O)C(C)(C)C)nc1)C(C(=O)O)C(=O)OCC>C1CCOC1>C=C(C(=O)OCC)C(CCC)c1ccc(NC(=O)C(C)(C)C)nc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2fe91ed6f0d34deca63adedf15b027ff | CCCC(c1ccc(NC(=O)C(C)(C)C)nc1)C(CSC(C)=O)C(=O)OCC>>CCCC(c1ccc(N)nc1)C(CS)C(=O)O | C(C)OC(C(C(CCC)C=1C=NC(=CC1)NC(C(C)(C)C)=O)CSC(C)=O)=O>>NC1=CC=C(C=N1)C(C(C(=O)O)CS)CCC | CC[O:17][C:15]([CH:12]([CH:4]([CH2:3][CH2:2][CH3:1])[c:5]1[cH:6][cH:7][c:8]([NH:9]C(=O)C(C)(C)C)[n:10][cH:11]1)[CH2:13][S:14]C(C)=O)=[O:16]>>[CH3:1][CH2:2][CH2:3][CH:4]([c:5]1[cH:6][cH:7][c:8]([NH2:9])[n:10][cH:11]1)[CH:12]([CH2:13][SH:14])[C:15](=[O:16])[OH:17] | CCCC(c1ccc(NC(=O)C(C)(C)C)nc1)C(CSC(C)=O)C(=O)OCC | CCCC(c1ccc(N)nc1)C(CS)C(=O)O | null | null | Cl | Reduction | OtherReaction | ffd06b16d1d7c1b14809fdc8490e62678cc3fe0cabd87ec335abf144ed764387 | b789f08c9fd13b1928e1d0ebdad16f9af390e5c4dda6d5e72eebf47184f97c16 | c1ccncc1 | C-C(-C)(-C)-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].C-C-[O;H0;D2;+0:6]-[C:7](=[O;D1;H0:8])-[C:9]-[C:10]-[S;H0;D2;+0:11]-C(-C)=O>>[NH2;D1;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:8]=[C:7](-[OH;D1;+0:6])-[C:9]-[C:10]-[SH;D1;+0:11] | 97 | [{"value": 97.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Acetylsulfanylmethyl-3-[6-(2,2-dimethyl-propionylamino)-pyridin-3-yl]-hexanoic acid ethyl ester (40.4 mg, 99 μmol) was dissolved under argon in aqueous hydrochloric acid (37%, 4.2 mL) and heated under reflux for 2 h. Concentration under reduced pressure (0.3 torr, 40° C.) gave the title compound as the hydrochloride ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amide.Carbo-thioester | Carboxylic acid.Primary amine.Aliphatic thiol | null | null | c1ccncc1 | HO- | Cl | null | null | CCCC(c1ccc(NC(=O)C(C)(C)C)nc1)C(CSC(C)=O)C(=O)OCC>Cl>CCCC(c1ccc(N)nc1)C(CS)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c46d7f258e53470bbb2ffe1789913e62 | CCOC(=O)CC(=O)OCC.Nc1ncc(C=O)s1>>CCOC(=O)C(=Cc1cnc(N)s1)C(=O)OCC | NC=1SC(=CN1)C=O.C(CC(=O)OCC)(=O)OCC.N1CCCCC1.C(C)(=O)O>>C(C)OC(C(C(=O)OCC)=CC1=CN=C(S1)N)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:14](=[O:15])[O:16][CH2:17][CH3:18].O=[CH:7][c:8]1[cH:9][n:10][c:11]([NH2:12])[s:13]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH:7][c:8]1[cH:9][n:10][c:11]([NH2:12])[s:13]1)[C:14](=[O:15])[O:16][CH2:17][CH3:18] | CCOC(=O)CC(=O)OCC.Nc1ncc(C=O)s1 | CCOC(=O)C(=Cc1cnc(N)s1)C(=O)OCC | null | null | CN(C)C=O.C(Cl)Cl.CCOC(=O)C.C(C)O | C-C Coupling | Aldol condensation | 4308c3bc8a698ffc0b4a25652616c227140ef668f7c572096e661e9937e780ad | fae8d7810715ce1cb0ea563a010deed21a5c5db9b9f45a5f7ae1c022defa3e22 | c1cscn1 | O=[CH;D2;+0:1]-[c:2]1:[#16;a:3]:[c:4]:[#7;a:5]:[c:6]:1.[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[CH2;D2;+0:11]-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15]>>[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[C;H0;D3;+0:11](=[CH;D2;+0:1]-[c:2]1:[#16;a:3]:[c:4]:[#7;a:5]:[c:6]:1)-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15] | 18.2 | [{"value": 18.0, "product": "C(C)OC(C(C(=O)OCC)=CC1=CN=C(S1)N)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 18.2, "product": "C(C)OC(C(C(=O)OCC)=CC1=CN=C(S1)N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 96 | HOUR | To a solution of 2-amino-thiazole-5-carbaldehyde (47%; 6 g; 23 mmol) in CH2Cl2 (30 mL) and DMF (30 mL), was added 4A molecular sieves, diethyl malonate (3.5 mL; 23 mmol), piperidine (1.1 mL; 11.5 mmol) and acetic acid (0.7 mL; 11.5 mmol). The reaction mixture was stirred at room temperature for 96 hours. Then EtOAc was... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester.Ester | Ester.Ester | null | null | c1cscn1 | HO- | CN(C)C=O.C(Cl)Cl.CCOC(=O)C.C(C)O | null | 96 | CCOC(=O)CC(=O)OCC.Nc1ncc(C=O)s1>CN(C)C=O.C(Cl)Cl.CCOC(=O)C.C(C)O>CCOC(=O)C(=Cc1cnc(N)s1)C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-643806574dc7417cbf0983e0af62a5ee | CCOC(=O)C(=Cc1cnc(N)s1)C(=O)OCC>>CCOC(=O)C(Cc1cnc(N)s1)C(=O)OCC | Cl.[BH3-]C#N.[Na+].C(C)OC(C(C(=O)OCC)=CC1=CN=C(S1)N)=O.CC1=C(C=C(C(=C1Br)O)Br)C2(C=3C=CC=CC3S(=O)(=O)O2)C=4C=C(C(=C(C4C)Br)O)Br>>C(C)OC(C(C(=O)OCC)CC1=CN=C(S1)N)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH:7][c:8]1[cH:9][n:10][c:11]([NH2:12])[s:13]1)[C:14](=[O:15])[O:16][CH2:17][CH3:18]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][n:10][c:11]([NH2:12])[s:13]1)[C:14](=[O:15])[O:16][CH2:17][CH3:18] | CCOC(=O)C(=Cc1cnc(N)s1)C(=O)OCC | CCOC(=O)C(Cc1cnc(N)s1)C(=O)OCC | null | null | C(C)O | Reduction | Hydrogenation (double to single) | 82d6ec73b59717a4a572168cc06c459bbf2eccbd024f338a2f5997dd52a87917 | 2ba235e232c824470a3666c07c146a899d7a673d93a41942db554b50d7062398 | c1cscn1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:5](=[CH;D2;+0:6]-[c:7]1:[#16;a:8]:[c:9]:[#7;a:10]:[c:11]:1)-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:5](-[CH2;D2;+0:6]-[c:7]1:[#16;a:8]:[c:9]:[#7;a:10]:[c:11]:1)-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15] | 87.8 | [{"value": 87.8, "product": "C(C)OC(C(C(=O)OCC)CC1=CN=C(S1)N)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.4, "product": "C(C)OC(C(C(=O)OCC)CC1=CN=C(S1)N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | NaCNBH3 (1.88 g; 29.9 mmol) was added to a stirred solution of 2-(2-amino-thiazol-5-ylmethylene)-malonic acid diethyl ester (1.13 g; 4.2 mmol) in ethanol at 0° C. The pH of the solution was monitored by addition of a small amount of Bromocresol Green to the solution. Concentrated HCl was added dropwise until the soluti... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Ester.Ester | null | null | c1cscn1 | null | C(C)O | null | 5 | CCOC(=O)C(=Cc1cnc(N)s1)C(=O)OCC>C(C)O>CCOC(=O)C(Cc1cnc(N)s1)C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-26c4cbffa7844871ab7a014911a09649 | CCOC(=O)C(Cc1cnc(NC(=O)OC(C)(C)C)s1)C(=O)OCC>>CCOC(=O)C(Cc1cnc(NC(=O)OC(C)(C)C)s1)C(=O)O | C(C)OC(C(C(=O)OCC)CC1=CN=C(S1)NC(=O)OC(C)(C)C)=O.[OH-].[K+]>>C(C)OC(C(C(=O)O)CC1=CN=C(S1)NC(=O)OC(C)(C)C)=O | CC[O:23][C:21]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][c:8]1[cH:9][n:10][c:11]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[s:20]1)=[O:22]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][n:10][c:11]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[s:20]1)[C:21](=[O:... | CCOC(=O)C(Cc1cnc(NC(=O)OC(C)(C)C)s1)C(=O)OCC | CCOC(=O)C(Cc1cnc(NC(=O)OC(C)(C)C)s1)C(=O)O | null | null | C1CCOC1.C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1cscn1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7]>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 66.4 | [{"value": 66.4, "product": "C(C)OC(C(C(=O)O)CC1=CN=C(S1)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.5, "product": "C(C)OC(C(C(=O)O)CC1=CN=C(S1)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 96 | HOUR | 2-(2-tert-Butoxycarbonylamino-thiazol-5-ylmethyl)-malonic acid diethyl ester (158 mg; 0.43 mmol) was dissolved in ethanol (1 mL) and THF (0.5 mL), and a solution of KOH (24 mg; 0.43 mmol) in ethanol (0.14 mL) was added at 0° C. The reaction mixture was stirred at room temperature for 96 hours, and then poured onto ice-... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cscn1 | Other | C1CCOC1.C(C)O | null | 96 | CCOC(=O)C(Cc1cnc(NC(=O)OC(C)(C)C)s1)C(=O)OCC>C1CCOC1.C(C)O>CCOC(=O)C(Cc1cnc(NC(=O)OC(C)(C)C)s1)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4a82f4f0a3034c1299a779581fcf48d0 | CCOC(=O)C(Cc1cnc(NC(=O)OC(C)(C)C)s1)C(=O)O>>C=C(Cc1cnc(NC(=O)OC(C)(C)C)s1)C(=O)OCC | C(C)OC(C(C(=O)O)CC1=CN=C(S1)NC(=O)OC(C)(C)C)=O.C=O.C(Cl)Cl.C(C)NCC>>C(C)OC(C(=C)CC1=CN=C(S1)NC(=O)OC(C)(C)C)=O | O=[C:1](O)[CH:2]([CH2:3][c:4]1[cH:5][n:6][c:7]([NH:8][C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[s:16]1)[C:17](=[O:18])[O:19][CH2:20][CH3:21]>>[CH2:1]=[C:2]([CH2:3][c:4]1[cH:5][n:6][c:7]([NH:8][C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[s:16]1)[C:17](=[O:18])[O:19][CH2:20][CH3:21] | CCOC(=O)C(Cc1cnc(NC(=O)OC(C)(C)C)s1)C(=O)O | C=C(Cc1cnc(NC(=O)OC(C)(C)C)s1)C(=O)OCC | null | null | O | Miscellaneous | OtherReaction | 485594ce7bba157615ffbb01ccede84a4e638576571b5d04649a06f3d4b7bce0 | 55e5b5078322f9f4fb0a7e9b5fc8a8cb9084e9135b447b8c441ad0800765792e | c1cscn1 | O-[C;H0;D3;+0:1](=O)-[CH;D3;+0:2](-[C:3]-[c:4](:[#16;a:5]):[c:6]:[#7;a:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11]>>[#16;a:5]:[c:4](-[C:3]-[C;H0;D3;+0:2](=[CH2;D1;+0:1])-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11]):[c:6]:[#7;a:7] | 81.8 | [{"value": 80.9, "product": "C(C)OC(C(=C)CC1=CN=C(S1)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.8, "product": "C(C)OC(C(=C)CC1=CN=C(S1)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a mixture of 2-(2-tert- butoxycarbonylamino-thiazol-5-ylmethyl)-malonic acid monoethyl ester (94 mg; 0.27 mmol), a 36% aqueous solution of formaldehyde (36 μl; 1.2 mmol), CH2Cl2 (0.2 mL) and water (0.2 mL) was added at 0° C. diethyl amine (30 μl; 0.40 mmol). The reaction mixture was stirred at room temperature overn... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester | Ester.Vinyl | null | null | c1cscn1 | Other | O | null | 8 | CCOC(=O)C(Cc1cnc(NC(=O)OC(C)(C)C)s1)C(=O)O>O>C=C(Cc1cnc(NC(=O)OC(C)(C)C)s1)C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2f5983c35a314e8b8afc593cf555a77b | C=C(C(=O)OCC)C(N)c1cnc(C(=O)OC(C)(C)C)s1.CC(O)=S>>CCOC(=O)C(CSC(C)=O)Cc1sc(C(=O)OC(C)(C)C)nc1N | C(C)N(CC)CC.C(C)OC(C(=C)C(C1=CN=C(S1)C(=O)OC(C)(C)C)N)=O.C(C)(=S)O>>C(C)OC(C(CC1=C(N=C(S1)C(=O)OC(C)(C)C)N)CSC(C)=O)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH2:7])[CH:12]([c:13]1[s:14][c:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[n:23][cH:24]1)[NH2:25].[S:8]=[C:9]([CH3:10])[OH:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][S:8][C:9]([CH3:10])=[O:11])[CH2:12][c:13]1[s:14][c:15]([C:16](=[O:17])[O:18][C:19]([CH3:... | C=C(C(=O)OCC)C(N)c1cnc(C(=O)OC(C)(C)C)s1.CC(O)=S | CCOC(=O)C(CSC(C)=O)Cc1sc(C(=O)OC(C)(C)C)nc1N | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | f942b9e608bdff24c4c937c8b840d1efbd0f94c7d37a90f1cb5f475b1e7212df | 85374cd39fc99eec945b5a8d7455ef5f8d0ed8170c44c1bbf34e480c1a8312b6 | c1cscn1 | [#8:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[#16;a:5]:[c:6](-[CH;D3;+0:7](-[NH2;D1;+0:8])-[C;H0;D3;+0:9](=[CH2;D1;+0:10])-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14]):[cH;D2;+0:15]:[#7;a:16]:1.[C;D1;H3:17]-[C;H0;D3;+0:18](-[OH;D1;+0:19])=[S;H0;D1;+0:20]>>[#8:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[#16;a:5]:[c:6](-[CH2;D2;+0:7]-[CH;D3;+0:9](-[CH... | 51.6 | [{"value": 51.6, "product": "C(C)OC(C(CC1=C(N=C(S1)C(=O)OC(C)(C)C)N)CSC(C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | Triethyl amine (32 μl; 0.23 mmol) was added to a solution of 2-(2-tert-butoxycarbonyl-amino-thiazol-5-ylmethyl)-acrylic acid ethyl ester (67 mg; 0.21 mmol) in thioacetic acid (0.4 mL) at 0° C. The reaction mixture was stirred at room temperature for 48 hours, and then poured onto ice-water. The aqueous layer was extrac... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine.Thiocarbonyl.Vinyl | Ester.Primary amine.Carbo-thioester | c1cscn1 | c1cscn1 | c1cscn1 | null | null | null | 48 | C=C(C(=O)OCC)C(N)c1cnc(C(=O)OC(C)(C)C)s1.CC(O)=S>>CCOC(=O)C(CSC(C)=O)Cc1sc(C(=O)OC(C)(C)C)nc1N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ed286a2851e74deaa693747f1fda9665 | CCOC(=O)C(CSC(C)=O)Cc1cnc(NC(=O)OC(C)(C)C)s1>>Nc1ncc(CC(CS)C(=O)O)s1 | C(C)OC(C(CC1=CN=C(S1)NC(=O)OC(C)(C)C)CSC(C)=O)=O>>NC=1SC(=CN1)CC(C(=O)O)CS | CC[O:12][C:10]([CH:7]([CH2:6][c:5]1[cH:4][n:3][c:2]([NH:1]C(=O)OC(C)(C)C)[s:13]1)[CH2:8][S:9]C(C)=O)=[O:11]>>[NH2:1][c:2]1[n:3][cH:4][c:5]([CH2:6][CH:7]([CH2:8][SH:9])[C:10](=[O:11])[OH:12])[s:13]1 | CCOC(=O)C(CSC(C)=O)Cc1cnc(NC(=O)OC(C)(C)C)s1 | Nc1ncc(CC(CS)C(=O)O)s1 | null | null | Cl | Reduction | OtherReaction | df63f36502c6e187beb1211487c3f0937031934a12a3c506c12c51a17b700a31 | 9a7c4efef36aa8beb2b85c58cd3924b350f3ef529d4eb0778d927167159d9d8b | c1cscn1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2]1:[#16;a:3]:[c:4]:[c:5]:[#7;a:6]:1.C-C-[O;H0;D2;+0:7]-[C:8](=[O;D1;H0:9])-[C:10]-[C:11]-[S;H0;D2;+0:12]-C(-C)=O>>[NH2;D1;+0:1]-[c:2]1:[#16;a:3]:[c:4]:[c:5]:[#7;a:6]:1.[O;D1;H0:9]=[C:8](-[OH;D1;+0:7])-[C:10]-[C:11]-[SH;D1;+0:12] | 33.3 | [{"value": 21.0, "product": "NC=1SC(=CN1)CC(C(=O)O)CS", "details": "PERCENTYIELD", "is_desired": false}, {"value": 33.3, "product": "NC=1SC(=CN1)CC(C(=O)O)CS", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-acetylsulfanylmethyl-3-(2-tert-butoxycarbonylamino-thiazol-5-yl)-propionic acid ethyl ester (43 mg; 0.11 mmol) in concentrated HCl (1.5 mL) was refluxed under argon for 1.5 hours. The reaction mixture was allowed to cool to room temperature and concentrated under reduced pressure to yield 30 mg of the c... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ether.Carbo-thioester.Boc | Carboxylic acid.Primary amine.Aliphatic thiol | null | null | c1cscn1 | HO- | Cl | null | null | CCOC(=O)C(CSC(C)=O)Cc1cnc(NC(=O)OC(C)(C)C)s1>Cl>Nc1ncc(CC(CS)C(=O)O)s1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-35a49464e9924d568c49d65afdf8ac83 | Fc1cccc(CBr)c1F.Nc1nc(S)nc(S)c1N>>Nc1nc(SCc2cccc(F)c2F)nc(SCc2cccc(F)c2F)c1N | O.FC1=C(CBr)C=CC=C1F.[OH-].[K+].NC=1C(=NC(=NC1N)S)S>>FC1=C(C=CC=C1F)CSC1=NC(=C(C(=N1)N)N)SCC1=C(C(=CC=C1)F)F | Br[CH2:6][c:7]1[cH:8][cH:9][cH:10][c:11]([F:12])[c:13]1[F:14].[NH2:1][c:25]1[n:3][c:2]([SH:5])[n:15][c:20]([SH:17])[c:19]1[NH2:28]>>[NH2:1][c:2]1[n:3][c:4]([S:5][CH2:6][c:7]2[cH:8][cH:9][cH:10][c:11]([F:12])[c:13]2[F:14])[n:15][c:16]([S:17][CH2:18][c:19]2[cH:20][cH:21][cH:22][c:23]([F:24])[c:25]2[F:26])[c:27]1[NH2:28] | Fc1cccc(CBr)c1F.Nc1nc(S)nc(S)c1N | Nc1nc(SCc2cccc(F)c2F)nc(SCc2cccc(F)c2F)c1N | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | 875d14edb3f41b02cab3bee580744195e96455e2ec6673b4e538282063d3ec9b | 7d872a8e5ff13f87c57e0f742a5e94fef0b487962cafda8a7ce4985bc36e2144 | c1ccc(CSc2ccnc(SCc3ccccc3)n2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[c;H0;D3;+0:6]1:[n;H0;D2;+0:7]:[c;H0;D3;+0:8](-[SH;D1;+0:9]):[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[SH;D1;+0:12]):[c;H0;D3;+0:13]:1-[NH2;D1;+0:14]>>[F;D1;H0:15]-[c:16]1:[c:17]:[c:18]:[cH;D2;+0:11]:[c;H0;D3;+0:13](-[C:19]-[S;H0;D2;+0:12]-[c:20]2:[n;H0;D2;+0:10]:[c:21](-[S;H0... | 64.7 | [{"value": 64.7, "product": "FC1=C(C=CC=C1F)CSC1=NC(=C(C(=N1)N)N)SCC1=C(C(=CC=C1)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of potassium hydroxide powder (7.72 g) in methanol (250 ml) was added first 5,6-diamino-2,4-pyrimidinedithiol (10.9 g) followed by 2,3-difluorobenzyl bromide (22.5 g). The reaction mixture was stirred for one hour at room temperature then poured into water (500 ml), giving a brown precipitate. This was is... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine.Primary amine.Aromatic thiol.Aromatic thiol | Aromatic halide.Aromatic halide.Primary amine.Primary amine.Monosulfide.Monosulfide | c1cncnc1 | c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1.c1ccccc1 | Br- | CO | null | 1 | Fc1cccc(CBr)c1F.Nc1nc(S)nc(S)c1N>CO>Nc1nc(SCc2cccc(F)c2F)nc(SCc2cccc(F)c2F)c1N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d60e4e9c520c41e3a9a992d14b316b33 | N#CCBr.Nc1nc(SCc2cccc(F)c2F)nc(SCc2cccc(F)c2F)c1N>>N#CCNc1c(N)nc(SCc2cccc(F)c2F)nc1SCc1cccc(F)c1F | FC1=C(C=CC=C1F)CSC1=NC(=C(C(=N1)N)N)SCC1=C(C(=CC=C1)F)F.C(C)(C)N(CC)C(C)C.BrCC#N>>NC1=NC(=NC(=C1NCC#N)SCC1=C(C(=CC=C1)F)F)SCC1=C(C(=CC=C1)F)F | Br[CH2:3][C:2]#[N:1].[NH2:4][c:5]1[c:6]([NH2:7])[n:8][c:9]([S:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][c:16]([F:17])[c:18]2[F:19])[n:20][c:21]1[S:22][CH2:23][c:24]1[cH:25][cH:26][cH:27][c:28]([F:29])[c:30]1[F:31]>>[N:1]#[C:2][CH2:3][NH:4][c:5]1[c:6]([NH2:7])[n:8][c:9]([S:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][c:16]([F:... | N#CCBr.Nc1nc(SCc2cccc(F)c2F)nc(SCc2cccc(F)c2F)c1N | N#CCNc1c(N)nc(SCc2cccc(F)c2F)nc1SCc1cccc(F)c1F | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CSc2ccnc(SCc3ccccc3)n2)cc1 | Br-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3].[#16:4]-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9](-[N;D1;H2:10]):[c:11]:1-[NH2;D1;+0:12]>>[#16:4]-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9](-[N;D1;H2:10]):[c:11]:1-[NH;D2;+0:12]-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3] | null | [] | null | null | null | null | A solution of the product of example 1 step a) (5.0 g), diisopropylethylamine (2.8 ml) and bromoacetonitrile (1.1 ml) in DMSO (50 ml) was heated at 100° C. for 5 hours. After cooling, the reaction mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride. The organic phase was dried over mag... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1cncnc1.c1ccccc1.c1ccccc1 | HBr | CS(=O)C | null | null | N#CCBr.Nc1nc(SCc2cccc(F)c2F)nc(SCc2cccc(F)c2F)c1N>CS(=O)C>N#CCNc1c(N)nc(SCc2cccc(F)c2F)nc1SCc1cccc(F)c1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5fd2ccf2dc594170826f4d7c291c7658 | N#CCNc1c(N)nc(SCc2cccc(F)c2F)nc1SCc1cccc(F)c1F>>Nc1cnc2c(SCc3cccc(F)c3F)nc(SCc3cccc(F)c3F)nc2n1 | NC1=NC(=NC(=C1NCC#N)SCC1=C(C(=CC=C1)F)F)SCC1=C(C(=CC=C1)F)F.[OH-].[K+]>>FC1=C(C=CC=C1F)CSC1=NC2=NC(=CN=C2C(=N1)SCC1=C(C(=CC=C1)F)F)N | [N:1]#[C:2][CH2:3][NH:4][c:5]1[c:6]([S:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][c:13]([F:14])[c:15]2[F:16])[n:17][c:18]([S:19][CH2:20][c:21]2[cH:22][cH:23][cH:24][c:25]([F:26])[c:27]2[F:28])[n:29][c:30]1[NH2:31]>>[NH2:1][c:2]1[cH:3][n:4][c:5]2[c:6]([S:7][CH2:8][c:9]3[cH:10][cH:11][cH:12][c:13]([F:14])[c:15]3[F:16])[n:17][c... | N#CCNc1c(N)nc(SCc2cccc(F)c2F)nc1SCc1cccc(F)c1F | Nc1cnc2c(SCc3cccc(F)c3F)nc(SCc3cccc(F)c3F)nc2n1 | null | null | ClCCl.CO | Aromatic Heterocycle Formation | OtherReaction | 959c4cb5cae311498051af91f0407d3da6b771c1846aa46cc57a0413e3c563dc | 74a4ef8489c7a5bc461b413b04c386abf402fddb095353fa9e4f523f588e3236 | c1ccc(CSc2nc(SCc3ccccc3)c3nccnc3n2)cc1 | [#16:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6](-[NH2;D1;+0:7]):[c:8]:1-[NH;D2;+0:9]-[CH2;D2;+0:10]-[C;H0;D2;+0:11]#[N;H0;D1;+0:12]>>[#16:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]2:[n;H0;D2;+0:7]:[c;H0;D3;+0:11](-[NH2;D1;+0:12]):[cH;D2;+0:10]:[n;H0;D2;+0:9]:[c:8]:2:1 | null | [] | null | null | null | null | A solution of the product from example 1 step b) (1.35 g) and potassium hydroxide (114 mg) in methanol (50 ml) and dichloromethane (20 ml) was stirred at room temperature for 24 hours. After evaporation in vacuo, the residue was purified by silica gel flash column chromatography, eluting with 5:1 dichloromethane:ethyl ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine.Secondary amine | Primary amine | c1cncnc1 | c1cnc2ncncc2n1 | c1ccccc1.c1cnc2ncncc2n1.c1ccccc1 | null | ClCCl.CO | null | null | N#CCNc1c(N)nc(SCc2cccc(F)c2F)nc1SCc1cccc(F)c1F>ClCCl.CO>Nc1cnc2c(SCc3cccc(F)c3F)nc(SCc3cccc(F)c3F)nc2n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f99cb156d7224367b03f8c191091bbb7 | NC(CO)CO.Nc1cnc2c(SCc3cccc(F)c3F)nc(SCc3cccc(F)c3F)nc2n1>>N.Nc1cnc2c(NC(CO)CO)nc(SCc3cccc(F)c3F)nc2n1 | FC1=C(C=CC=C1F)CSC1=NC2=NC(=CN=C2C(=N1)SCC1=C(C(=CC=C1)F)F)N.NC(CO)CO>>N.NC1=CN=C2C(=NC(=NC2=N1)SCC1=C(C(=CC=C1)F)F)NC(CO)CO | [NH2:8][CH:9]([CH2:10][OH:11])[CH2:12][OH:13].Fc1cccc(CS[c:7]2[n:1][c:15]([S:16][CH2:17][c:18]3[cH:19][cH:20][cH:21][c:22]([F:23])[c:24]3[F:25])[n:26][c:27]3[c:6]2[n:5][cH:4][c:3]([NH2:2])[n:28]3)c1F>>[NH3:1].[NH2:2][c:3]1[cH:4][n:5][c:6]2[c:7]([NH:8][CH:9]([CH2:10][OH:11])[CH2:12][OH:13])[n:14][c:15]([S:16][CH2:17][c:... | NC(CO)CO.Nc1cnc2c(SCc3cccc(F)c3F)nc(SCc3cccc(F)c3F)nc2n1 | N.Nc1cnc2c(NC(CO)CO)nc(SCc3cccc(F)c3F)nc2n1 | null | null | CN1C=NC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | 39abd0ccb46aac6f605b6272676358933db093ca6b086fa512654dbf19ac3c17 | de5bfea8ca514452862a61adfdec3997beea2eface0f02e0a2cf4d45ec96d562 | c1ccc(CSc2ncc3nccnc3n2)cc1 | F-c1:c:c:c:c(-C-S-[c;H0;D3;+0:1]2:[n;H0;D2;+0:2]:[c;H0;D3;+0:3](-[#16:4]-[C:5]):[#7;a:6]:[c:7]3:[#7;a:8]:[c:9]:[c:10]:[#7;a:11]:[c:12]:3:2):c:1-F.[C:13]-[C:14](-[C:15])-[NH2;D1;+0:16]>>[C:13]-[C:14](-[C:15])-[NH;D2;+0:16]-[c;H0;D3;+0:1]1:[#7;a:17]:[c;H0;D3;+0:3](-[#16:4]-[C:5]):[#7;a:6]:[c:7]2:[#7;a:8]:[c:9]:[c:10]:[#7... | 39.2 | [{"value": 39.2, "product": "NC1=CN=C2C(=NC(=NC2=N1)SCC1=C(C(=CC=C1)F)F)NC(CO)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of the product from example 1, step (c) (0.12 g) and serinol (330 mg) in 1-methylimidazole (1 ml) was heated at 130° C. for 90 minutes. After cooling, the reaction mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride. The organic phase was dried over magnesium sulphate, filte... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Monosulfide.Monosulfide | Secondary amine.Monosulfide | c1ccccc1.c1cnc2ncncc2n1 | c1cnc2ncncc2n1 | c1cnc2ncncc2n1.c1ccccc1 | HF | CN1C=NC=C1 | null | null | NC(CO)CO.Nc1cnc2c(SCc3cccc(F)c3F)nc(SCc3cccc(F)c3F)nc2n1>CN1C=NC=C1>N.Nc1cnc2c(NC(CO)CO)nc(SCc3cccc(F)c3F)nc2n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b1480fa09b40490e844336d04e3d4254 | CC(N)(CO)CO.Nc1cnc2c(SCc3cccc(F)c3F)nc(SCc3cccc(F)c3F)nc2n1>>CC(CO)(CO)Nc1nc(SCc2cccc(F)c2F)nc2nc(N)cnc12 | FC1=C(C=CC=C1F)CSC1=NC2=NC(=CN=C2C(=N1)SCC1=C(C(=CC=C1)F)F)N.NC(CO)(CO)C>>NC1=CN=C2C(=NC(=NC2=N1)SCC1=C(C(=CC=C1)F)F)NC(CO)(CO)C | [CH3:1][C:2]([CH2:3][OH:4])([CH2:5][OH:6])[NH2:7].Fc1cccc(CS[c:8]2[n:9][c:10]([S:11][CH2:12][c:13]3[cH:14][cH:15][cH:16][c:17]([F:18])[c:19]3[F:20])[n:21][c:22]3[n:23][c:24]([NH2:25])[cH:26][n:27][c:28]23)c1F>>[CH3:1][C:2]([CH2:3][OH:4])([CH2:5][OH:6])[NH:7][c:8]1[n:9][c:10]([S:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][c... | CC(N)(CO)CO.Nc1cnc2c(SCc3cccc(F)c3F)nc(SCc3cccc(F)c3F)nc2n1 | CC(CO)(CO)Nc1nc(SCc2cccc(F)c2F)nc2nc(N)cnc12 | null | null | CN1C=NC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | eac9d9049a37d474bff6cf1242828e8e6a051f0ff56b69f3289eb8bb2609b1af | c6f16693960bae0efb1af2931acd0c695f0f746d607e6b85d00f057afa9e72a0 | c1ccc(CSc2ncc3nccnc3n2)cc1 | F-c1:c:c:c:c(-C-S-[c;H0;D3;+0:1]2:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]3:[#7;a:6]:[c:7]:[c:8]:[#7;a:9]:[c:10]:3:2):c:1-F.[C:11]-[C:12](-[C:13])(-[C;D1;H3:14])-[NH2;D1;+0:15]>>[C:11]-[C:12](-[C:13])(-[C;D1;H3:14])-[NH;D2;+0:15]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[#7;a:6]:[c:7]:[c:8]:[#7;a:9]:[c:10]:2:1 | null | [] | null | null | null | null | A solution of the product from example 1, step (c) (0.25 g) and 2-amino-2-methyl-1,3-propanediol (0.28 ml) in N-methylimidazole (1 ml) was heated in a microwave at 160° C. for 95 minutes. After cooling, the reaction mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride. The organic phase... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Monosulfide | Secondary amine | c1ccccc1.c1cnc2ncncc2n1 | c1cnc2ncncc2n1 | c1ccccc1.c1cnc2ncncc2n1 | HF | CN1C=NC=C1 | null | null | CC(N)(CO)CO.Nc1cnc2c(SCc3cccc(F)c3F)nc(SCc3cccc(F)c3F)nc2n1>CN1C=NC=C1>CC(CO)(CO)Nc1nc(SCc2cccc(F)c2F)nc2nc(N)cnc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-17e0d1ecf4ff4543b216d3fbe834abf2 | C[C@H](CO)Nc1nc(S(=O)(=O)Cc2cccc(F)c2F)nc2nc(N)cnc12.Cc1ccc(CS)o1>>Cc1ccc(CSc2nc(N[C@H](C)CO)c3ncc(N)nc3n2)o1 | NC1=CN=C2C(=NC(=NC2=N1)S(=O)(=O)CC1=C(C(=CC=C1)F)F)N[C@@H](CO)C.CC1=CC=C(O1)CS.CC(C)([O-])C.[K+]>>NC1=CN=C2C(=NC(=NC2=N1)SCC=1OC(=CC1)C)N[C@@H](CO)C | O=S(=O)(Cc1cccc(F)c1F)[c:8]1[n:9][c:10]([NH:11][C@H:12]([CH3:13])[CH2:14][OH:15])[c:16]2[n:17][cH:18][c:19]([NH2:20])[n:21][c:22]2[n:23]1.[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][SH:7])[o:24]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][S:7][c:8]2[n:9][c:10]([NH:11][C@H:12]([CH3:13])[CH2:14][OH:15])[c:16]3[n:17][cH:18][c:19]... | C[C@H](CO)Nc1nc(S(=O)(=O)Cc2cccc(F)c2F)nc2nc(N)cnc12.Cc1ccc(CS)o1 | Cc1ccc(CSc2nc(N[C@H](C)CO)c3ncc(N)nc3n2)o1 | null | null | CS(=O)C.C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | d76597ff8073dc2c252ca00cf01f220ab3f2c2fe6d3c436ae87a81ebb3fa99c1 | bc860fac18574184cfbf29285a0dea0bf44dac7ecd1757c8a429854f361bafbe | c1coc(CSc2ncc3nccnc3n2)c1 | F-c1:c:c:c:c(-C-S(=O)(=O)-[c;H0;D3;+0:1]2:[#7;a:2]:[c:3]3:[#7;a:4]:[c:5]:[c:6]:[#7;a:7]:[c:8]:3:[c:9]:[#7;a:10]:2):c:1-F.[#8;a:11]:[c:12]-[C:13]-[SH;D1;+0:14]>>[#8;a:11]:[c:12]-[C:13]-[S;H0;D2;+0:14]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[#7;a:4]:[c:5]:[c:6]:[#7;a:7]:[c:8]:2:[c:9]:[#7;a:10]:1 | null | [] | null | null | 1 | HOUR | A solution of the product from example 10, step (a) (0.18 g) and 5-methyl-2-furanmethanethiol (75 mg) in anhydrous DMSO (3 ml) was treated with potassium t-butoxide solution in THF (1.0 M, 0.44 ml) and stirred at room temperature for 1 hour. The solution was purified directly by preparative reversed phase HPLC on a Wat... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aliphatic thiol.Sulfone | Monosulfide | c1ccccc1.c1cnc2ncncc2n1 | c1cnc2ncncc2n1 | c1ccoc1.c1cnc2ncncc2n1 | HF | CS(=O)C.C1CCOC1 | null | 1 | C[C@H](CO)Nc1nc(S(=O)(=O)Cc2cccc(F)c2F)nc2nc(N)cnc12.Cc1ccc(CS)o1>CS(=O)C.C1CCOC1>Cc1ccc(CSc2nc(N[C@H](C)CO)c3ncc(N)nc3n2)o1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3042970ef6b7426bbb55b07168a0c8b5 | C[C@H](CO)Nc1nc(S(=O)(=O)Cc2cccc(F)c2F)nc2nc(N)cnc12.Sc1cccs1>>C[C@H](CO)Nc1nc(SCc2cccs2)nc2nc(N)cnc12 | NC1=CN=C2C(=NC(=NC2=N1)S(=O)(=O)CC1=C(C(=CC=C1)F)F)N[C@@H](CO)C.S1C(=CC=C1)S.CC(C)([O-])C.[K+]>>NC1=CN=C2C(=NC(=NC2=N1)SCC=1SC=CC1)N[C@@H](CO)C | O=[S:9](=O)([c:8]1[n:7][c:6]([NH:5][C@H:2]([CH3:1])[CH2:3][OH:4])[c:23]2[c:17]([n:16]1)[n:18][c:19]([NH2:20])[cH:21][n:22]2)[CH2:10]c1cccc(F)c1F.S[c:11]1[cH:12][cH:13][cH:14][s:15]1>>[CH3:1][C@H:2]([CH2:3][OH:4])[NH:5][c:6]1[n:7][c:8]([S:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][s:15]2)[n:16][c:17]2[n:18][c:19]([NH2:20])[... | C[C@H](CO)Nc1nc(S(=O)(=O)Cc2cccc(F)c2F)nc2nc(N)cnc12.Sc1cccs1 | C[C@H](CO)Nc1nc(SCc2cccs2)nc2nc(N)cnc12 | null | null | CS(=O)C.C1CCOC1 | C-C Coupling | OtherReaction | 36a4950e2924e1b8772d99e8ae64968da89b14f62c0af89c871015d51fc74468 | e5e0c2a4e00c80963b86db95a92f51ad89bbc2254c7953d22b0042761e20e589 | c1csc(CSc2ncc3nccnc3n2)c1 | F-c1:c:c:c:c(-[CH2;D2;+0:1]-[S;H0;D4;+0:2](=O)(=O)-[c:3]2:[#7;a:4]:[c:5](:[#7;a:6]):[c:7](:[#7;a:8]):[c:9]:[#7;a:10]:2):c:1-F.S-[c;H0;D3;+0:11]1:[#16;a:12]:[c:13]:[c:14]:[c:15]:1>>[#7;a:6]:[c:5]1:[#7;a:4]:[c:3](-[S;H0;D2;+0:2]-[CH2;D2;+0:1]-[c;H0;D3;+0:11]2:[#16;a:12]:[c:13]:[c:14]:[c:15]:2):[#7;a:10]:[c:9]:[c:7]:1:[#7... | null | [] | null | null | 1 | HOUR | A solution of the product from Example 10, step (a) (0.18 g) and 2-thienylmercaptan (70 mg) in anhydrous DMSO (3 ml) was treated with potassium t-butoxide solution in THF (1.0 M, 0.44 ml) and stirred at room temperature for 1 hour. The solution was purified directly by preparative reversed phase HPLC on a Waters 19×50 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic thiol.Sulfone | Monosulfide | c1ccccc1.c1ccsc1 | c1ccsc1 | c1ccsc1.c1cnc2ncncc2n1 | HF | CS(=O)C.C1CCOC1 | null | 1 | C[C@H](CO)Nc1nc(S(=O)(=O)Cc2cccc(F)c2F)nc2nc(N)cnc12.Sc1cccs1>CS(=O)C.C1CCOC1>C[C@H](CO)Nc1nc(SCc2cccs2)nc2nc(N)cnc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a8c82af914864d3bb1fb466e1bacd794 | Fc1c(Cl)cccc1CBr.Nc1nc(S)nc(S)c1N>>Nc1nc(SCc2cccc(Cl)c2F)nc(SCc2cccc(Cl)c2F)c1N | O.ClC=1C(=C(CBr)C=CC1)F.[OH-].[K+].NC=1C(=NC(=NC1N)S)S>>ClC=1C(=C(C=CC1)CSC1=NC(=C(C(=N1)N)N)SCC1=C(C(=CC=C1)Cl)F)F | Br[CH2:6][c:7]1[cH:8][cH:9][cH:10][c:11]([Cl:12])[c:13]1[F:14].[NH2:1][c:23]1[n:3][c:2]([SH:5])[n:15][c:19]([SH:17])[c:25]1[NH2:28]>>[NH2:1][c:2]1[n:3][c:4]([S:5][CH2:6][c:7]2[cH:8][cH:9][cH:10][c:11]([Cl:12])[c:13]2[F:14])[n:15][c:16]([S:17][CH2:18][c:19]2[cH:20][cH:21][cH:22][c:23]([Cl:24])[c:25]2[F:26])[c:27]1[NH2:2... | Fc1c(Cl)cccc1CBr.Nc1nc(S)nc(S)c1N | Nc1nc(SCc2cccc(Cl)c2F)nc(SCc2cccc(Cl)c2F)c1N | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | 875d14edb3f41b02cab3bee580744195e96455e2ec6673b4e538282063d3ec9b | 7d872a8e5ff13f87c57e0f742a5e94fef0b487962cafda8a7ce4985bc36e2144 | c1ccc(CSc2ccnc(SCc3ccccc3)n2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[c;H0;D3;+0:6]1:[n;H0;D2;+0:7]:[c;H0;D3;+0:8](-[SH;D1;+0:9]):[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[SH;D1;+0:12]):[c;H0;D3;+0:13]:1-[NH2;D1;+0:14]>>[Cl;D1;H0:15]-[c;H0;D3;+0:6]1:[c:16]:[c:17]:[c:18]:[c;H0;D3;+0:11](-[C:19]-[S;H0;D2;+0:12]-[c:20]2:[n;H0;D2;+0:10]:[c:21](-[S;... | 83.4 | [{"value": 83.4, "product": "ClC=1C(=C(C=CC1)CSC1=NC(=C(C(=N1)N)N)SCC1=C(C(=CC=C1)Cl)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of potassium hydroxide powder (2.5 g) in methanol (80 ml) was added first 5,6-diamino-2,4-pyrimidinedithiol (3.6 g) followed by 3-chloro-2-fluorobenzyl bromide (6.3 g). The reaction mixture was stirred for one hour at room temperature then poured into water (180 ml), giving a brown precipitate. This was i... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine.Primary amine.Aromatic thiol.Aromatic thiol | Aromatic halide.Aromatic halide.Primary amine.Primary amine.Monosulfide.Monosulfide | c1cncnc1 | c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1.c1ccccc1 | Br- | CO | null | 1 | Fc1c(Cl)cccc1CBr.Nc1nc(S)nc(S)c1N>CO>Nc1nc(SCc2cccc(Cl)c2F)nc(SCc2cccc(Cl)c2F)c1N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-647e8eb37a8b4bd2ad684e9511d1df3d | N#CCBr.Nc1nc(SCc2cccc(Cl)c2F)nc(SCc2cccc(Cl)c2F)c1N>>N#CCNc1c(N)nc(SCc2cccc(Cl)c2F)nc1SCc1cccc(Cl)c1F | ClC=1C(=C(C=CC1)CSC1=NC(=C(C(=N1)N)N)SCC1=C(C(=CC=C1)Cl)F)F.C(C)(C)N(CC)C(C)C.BrCC#N>>NC1=NC(=NC(=C1NCC#N)SCC1=C(C(=CC=C1)Cl)F)SCC1=C(C(=CC=C1)Cl)F | Br[CH2:3][C:2]#[N:1].[NH2:4][c:5]1[c:6]([NH2:7])[n:8][c:9]([S:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][c:16]([Cl:17])[c:18]2[F:19])[n:20][c:21]1[S:22][CH2:23][c:24]1[cH:25][cH:26][cH:27][c:28]([Cl:29])[c:30]1[F:31]>>[N:1]#[C:2][CH2:3][NH:4][c:5]1[c:6]([NH2:7])[n:8][c:9]([S:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][c:16]([... | N#CCBr.Nc1nc(SCc2cccc(Cl)c2F)nc(SCc2cccc(Cl)c2F)c1N | N#CCNc1c(N)nc(SCc2cccc(Cl)c2F)nc1SCc1cccc(Cl)c1F | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CSc2ccnc(SCc3ccccc3)n2)cc1 | Br-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3].[#16:4]-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9](-[N;D1;H2:10]):[c:11]:1-[NH2;D1;+0:12]>>[#16:4]-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9](-[N;D1;H2:10]):[c:11]:1-[NH;D2;+0:12]-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3] | null | [] | 100 | CELSIUS | null | null | To a solution of the product of example 13, step (a) (4.2 g) and diisopropylethylamine (1.2 ml) in dioxan (40 ml) was added bromoacetonitrile (1.2 g) and the mixture heated at 100° C. for 23 hours. After cooling, the red reaction solution was adsorbed onto silica and purified by silica gel flash column chromatography, ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1cncnc1.c1ccccc1.c1ccccc1 | HBr | O1CCOCC1 | 100 | null | N#CCBr.Nc1nc(SCc2cccc(Cl)c2F)nc(SCc2cccc(Cl)c2F)c1N>O1CCOCC1>N#CCNc1c(N)nc(SCc2cccc(Cl)c2F)nc1SCc1cccc(Cl)c1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8b0ef7003d124452b8d43d2ab90b786d | N#CCNc1c(N)nc(SCc2cccc(Cl)c2F)nc1SCc1cccc(Cl)c1F>>Nc1cnc2c(SCc3cccc(Cl)c3F)nc(SCc3cccc(Cl)c3F)nc2n1 | NC1=NC(=NC(=C1NCC#N)SCC1=C(C(=CC=C1)Cl)F)SCC1=C(C(=CC=C1)Cl)F.[OH-].[K+]>>ClC=1C(=C(C=CC1)CSC1=NC2=NC(=CN=C2C(=N1)SCC1=C(C(=CC=C1)Cl)F)N)F | [N:1]#[C:2][CH2:3][NH:4][c:5]1[c:6]([S:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][c:13]([Cl:14])[c:15]2[F:16])[n:17][c:18]([S:19][CH2:20][c:21]2[cH:22][cH:23][cH:24][c:25]([Cl:26])[c:27]2[F:28])[n:29][c:30]1[NH2:31]>>[NH2:1][c:2]1[cH:3][n:4][c:5]2[c:6]([S:7][CH2:8][c:9]3[cH:10][cH:11][cH:12][c:13]([Cl:14])[c:15]3[F:16])[n:17... | N#CCNc1c(N)nc(SCc2cccc(Cl)c2F)nc1SCc1cccc(Cl)c1F | Nc1cnc2c(SCc3cccc(Cl)c3F)nc(SCc3cccc(Cl)c3F)nc2n1 | null | null | ClCCl.CO | Aromatic Heterocycle Formation | OtherReaction | 959c4cb5cae311498051af91f0407d3da6b771c1846aa46cc57a0413e3c563dc | 74a4ef8489c7a5bc461b413b04c386abf402fddb095353fa9e4f523f588e3236 | c1ccc(CSc2nc(SCc3ccccc3)c3nccnc3n2)cc1 | [#16:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6](-[NH2;D1;+0:7]):[c:8]:1-[NH;D2;+0:9]-[CH2;D2;+0:10]-[C;H0;D2;+0:11]#[N;H0;D1;+0:12]>>[#16:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]2:[n;H0;D2;+0:7]:[c;H0;D3;+0:11](-[NH2;D1;+0:12]):[cH;D2;+0:10]:[n;H0;D2;+0:9]:[c:8]:2:1 | null | [] | null | null | null | null | A solution of the product from example 13, step (b) (1.4 g) and potassium hydroxide (110 mg) in methanol (80 ml) and dichloromethane (120 ml) was stirred at room temperature for 24 hours. After evaporation in vacuo, the residue rendered the subtitled compound as a pale yellow solid (1.4 g).
Conditions: See reaction.not... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine.Secondary amine | Primary amine | c1cncnc1 | c1cnc2ncncc2n1 | c1ccccc1.c1cnc2ncncc2n1.c1ccccc1 | null | ClCCl.CO | null | null | N#CCNc1c(N)nc(SCc2cccc(Cl)c2F)nc1SCc1cccc(Cl)c1F>ClCCl.CO>Nc1cnc2c(SCc3cccc(Cl)c3F)nc(SCc3cccc(Cl)c3F)nc2n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c721c7a16cd34905bedb5b9e54870cd9 | CCCN(CCC)C1CCc2cccc(O)c2C1.CCCN(CCC)C1CCc2cccc(O)c2C1.CCCN(CCC)C1CCc2cccc(O)c2C1.O=C(c1ccc(F)cc1)C1CCN(CCn2c(=O)[nH]c3ccccc3c2=O)CC1.O=C1CC2(CCCC2)CC(=O)N1CCCCN1CCN(c2ncccn2)CC1>>CCCC(C)C1(CC)C(=O)NC(=O)NC1=O | CCCN(CCCl)C1CCC2=C(C1)C(=CC=C2)OC.C=1C=NC(=NC1)N2CCN(CC2)CCCCN3C(=O)CC4(CCCC4)CC3=O.N[C@@H](CCC(=O)[O-])C(=O)[O-].CCCN(CCC)C1CCC=2C=CC=C(C2C1)O.C=1C=NC(=NC1)N2CCN(CC2)CCCCN3C(=O)CC4(CCCC4)CC3=O.C=1C=CC2=C(C1)C(=O)N(C(=O)N2)CCN3CCC(CC3)C(=O)C=4C=CC(=CC4)F.CCCN(CCC)C1CCC=2C=CC=C(C2C1)O.CCCN(CCC)C1CCC=2C=CC=C(C2C1)O.CCCN(... | CCCN(C1CCc2cccc(O)c2C1)[CH2:3][CH2:2][CH3:1].CCCN(CCC)C1CCc2cccc(O)c2[CH2:7]1.CCCN(CC[CH3:8])C1CCc2cccc(O)c2C1.O=C(c1ccc(F)cc1)[CH:4]1CCN(CC[n:11]2[c:9](=[O:10])[c:6]3cccc[c:15]3[nH:14][c:12]2=[O:13])C[CH2:5]1.O=C1CC2(CCCC2)CC(=[O:16])N1CCCCN1CCN(c2ncccn2)CC1>>[CH3:1][CH2:2][CH2:3][CH:4]([CH3:5])[C:6]1([CH2:7][CH3:8])[... | CCCN(CCC)C1CCc2cccc(O)c2C1.CCCN(CCC)C1CCc2cccc(O)c2C1.CCCN(CCC)C1CCc2cccc(O)c2C1.O=C(c1ccc(F)cc1)C1CCN(CCn2c(=O)[nH]c3ccccc3c2=O)CC1.O=C1CC2(CCCC2)CC(=O)N1CCCCN1CCN(c2ncccn2)CC1 | CCCC(C)C1(CC)C(=O)NC(=O)NC1=O | null | null | null | C-C Coupling | OtherReaction | 6c4f434b79f267148f88424ed894da1764fe14accd6774ad630178836800bdc2 | 1b159b79fcfb115eaaa8a1249b69813c8a7ca624bb6273e822122106a13cf2d9 | O=C1CC(=O)NC(=O)N1 | C-C-C-N(-C-C-C)-C1-C-C-c2:c:c:c:c(-O):c:2-[CH2;D2;+0:1]-1.C-C-C-N(-C-C-[CH3;D1;+0:2])-C1-C-C-c2:c:c:c:c(-O):c:2-C-1.C-C-C-N(-[CH2;D2;+0:3]-[C:4]-[C;D1;H3:5])-C1-C-C-c2:c:c:c:c(-O):c:2-C-1.F-c1:c:c:c(-C(=O)-[CH;D3;+0:6]2-C-C-N(-C-C-[n;H0;D3;+0:7]3:[c;H0;D3;+0:8](=[O;D1;H0:9]):[nH;D2;+0:10]:[c;H0;D3;+0:11]4:c:c:c:c:[c;H0... | null | [] | null | null | 24 | HOUR | The mechanism(s) and site(s) whereby 5HT1A agonistic drugs act to improve respiration following SCI remain to be further investigated. However, the beneficial effects of 8-OH-DPAT and buspirone on p.i. respiration that we observed can not be owned to possible neuronal protection for two reasons. First, by 24 hours and ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Substituted dicarboximide.Aromatic alcohol.Aromatic alcohol.Aromatic alcohol.Tertiary amine.Tertiary amine.Tertiary amine.Tertiary amine.Tertiary amine.Tertiary amine | Urea.Unsubstituted dicarboximide.Unsubstituted dicarboximide | c1ccc2c(c1)CCCC2.c1ccc2c(c1)CCCC2.c1ccc2c(c1)CCCC2.c1ccccc1.C1CCNCC1.c1ncc2ccccc2n1.C1CCC2(C1)CCNCC2.C1CNCCN1.c1cncnc1 | C1CNCNC1 | C1CNCNC1 | HF | null | null | 24 | CCCN(CCC)C1CCc2cccc(O)c2C1.CCCN(CCC)C1CCc2cccc(O)c2C1.CCCN(CCC)C1CCc2cccc(O)c2C1.O=C(c1ccc(F)cc1)C1CCN(CCn2c(=O)[nH]c3ccccc3c2=O)CC1.O=C1CC2(CCCC2)CC(=O)N1CCCCN1CCN(c2ncccn2)CC1>>CCCC(C)C1(CC)C(=O)NC(=O)NC1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-633610f700a141bdb66e0a21ff49bc7a | Fc1ccc(S)cc1.O=C1CCO1>>O=C(O)CCSc1ccc(F)cc1 | FC1=CC=C(C=C1)S.C1(CCO1)=O.[H-].[Na+]>>FC1=CC=C(C=C1)SCCC(=O)O | [SH:6][c:7]1[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]1.[O:1]=[C:2]1[O:3][CH2:5][CH2:4]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][S:6][c:7]1[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]1 | Fc1ccc(S)cc1.O=C1CCO1 | O=C(O)CCSc1ccc(F)cc1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | ee53ca213e38c18d543bd709672de517d667f47b5955431ef3bc3d91afe366bd | 05628bef7dd0f55088da5387721deff8811cd1b517cb22d3428864d9538ab16d | c1ccccc1 | [O;D1;H0:1]=[C:2]1-[C:3]-[CH2;D2;+0:4]-[O;H0;D2;+0:5]-1.[SH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:1]=[C:2](-[OH;D1;+0:5])-[C:3]-[CH2;D2;+0:4]-[S;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | 89 | [{"value": 89.0, "product": "FC1=CC=C(C=C1)SCCC(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.4, "product": "FC1=CC=C(C=C1)SCCC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | p-Fluorothiophenol (5 g, 40 mmol) and β-propiolactone (2.8 g, 40 mmol) were dissolved in THF (36 mL of freshly distilled) and then placed in an ice bath. 95% sodium hydride (1 g, 42.9 mmol) was added in small portions over 1 hour. The reaction was allowed to stir at 0° C. for 2 hours, then placed in the freezer overnig... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Aromatic thiol | Carboxylic acid.Monosulfide | C1COC1 | null | c1ccccc1 | null | C1CCOC1 | 0 | 2 | Fc1ccc(S)cc1.O=C1CCO1>C1CCOC1>O=C(O)CCSc1ccc(F)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-091b452045f94ad992f472ac19b451ac | O=C(O)CCS(=O)(=O)c1ccc(F)cc1>>O=C1CCSc2ccc(F)cc21 | Cl.C(C(=O)Cl)(=O)Cl.FC1=CC=C(C=C1)S(=O)(=O)CCC(=O)O.[Al+3].[Cl-].[Cl-].[Cl-]>>FC=1C=CC2=C(C(CCS2)=O)C1 | O=[S:5](=O)([CH2:4][CH2:3][C:2](O)=[O:1])[c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]1>>[O:1]=[C:2]1[CH2:3][CH2:4][S:5][c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][c:12]21 | O=C(O)CCS(=O)(=O)c1ccc(F)cc1 | O=C1CCSc2ccc(F)cc21 | null | CN(C=O)C | ClCCl.O | Reduction | OtherReaction | 3ef38121e38dc9ec41a651ba1ce4461afbd8a5a4ca5897b56b2e53ecf8a0723e | 01b4e013f887efb034169525990ec8cb923d898b053e77e8ebf10f956dd2688c | O=C1CCSc2ccccc21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[S;H0;D4;+0:5](=O)(=O)-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[C:3]-[C:4]-[S;H0;D2;+0:5]-[c:6](:[c:7]):[c;H0;D3;+0:8]-1:[c:9]:[c:10] | 93.3 | [{"value": 93.0, "product": "FC=1C=CC2=C(C(CCS2)=O)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.3, "product": "FC=1C=CC2=C(C(CCS2)=O)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 0.5 | HOUR | 3-[(4-fluorophenyl)sulfonyl]propanoic acid (3 g, 15 mmol) was dissolved in dichloromethane (30 mL) and cooled to 0° C. in an ice bath. Oxalyl chloride (10 mL) was added slowly, dimethyl formamide (1 drop) was added and the reaction mixture was stirred at 0° C. for 0.5 hours. At which point the reaction was concentrated... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Sulfone | Ketone.Monosulfide | c1ccccc1 | c1ccc2c(c1)CCCS2 | c1ccc2c(c1)CCCS2 | HO- | CN(C=O)C.ClCCl.O | 0 | 0.5 | O=C(O)CCS(=O)(=O)c1ccc(F)cc1>CN(C=O)C.ClCCl.O>O=C1CCSc2ccc(F)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-73e9fdec864a4a3cb7643dbaad973852 | O=C1CCSc2ccc(F)cc21>>O=C1CCSc2ccc(F)cc2N1 | S(O)(O)(=O)=O.FC=1C=CC2=C(C(CCS2)=O)C1.C(C)(=O)O.[N-]=[N+]=[N-].[Na+]>>FC=1C=CC2=C(NC(CCS2)=O)C1 | [O:1]=[C:2]1[CH2:3][CH2:4][S:5][c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][c:12]21>>[O:1]=[C:2]1[CH2:3][CH2:4][S:5][c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][c:12]2[NH:13]1 | O=C1CCSc2ccc(F)cc21 | O=C1CCSc2ccc(F)cc2N1 | null | null | null | Functional Group Addition | Schmidt ketone amide | 4982e5375548573cd395ae4cf6a0d33b202acad7f25bd7beb27f06a6bf26b504 | 2eb609f54422c0279557c5451dffbcf43fa7dc53a915eee10665042f34f6a171 | O=C1CCSc2ccccc2N1 | [O;D1;H0:1]=[C;H0;D3;+0:2]1-[C:3]-[C:4]-[#16:5]-[c:6](:[c:7]):[c;H0;D3;+0:8]-1:[c:9]:[c:10]>>[O;D1;H0:1]=[C;H0;D3;+0:2]1-[#7:11]-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:6](:[c:7])-[#16:5]-[C:4]-[C:3]-1 | 75.1 | [{"value": 24.0, "product": "FC=1C=CC2=C(NC(CCS2)=O)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.1, "product": "FC=1C=CC2=C(NC(CCS2)=O)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 1.5 | HOUR | 6-fluoro-2,3-dihydro-4H-1-benzothiopyran-4-one (100 mg, 0.54 mmol) was dissolved in acetic acid (0.5 mL, 1.1 eq), sodium azide (71.2 mg, 1.1 mmol) was added and mixture was heated to 50° C. Sulfuric acid (0.13 mL, 4.3 eq) was added slowly and stirred at 50° C. for 1.5 hours. Ice chips (150 mg) were added and a green so... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary amide | c1ccc2c(c1)CCCS2 | c1ccc2c(c1)NCCCS2 | c1ccc2c(c1)NCCCS2 | Other | null | 50 | 1.5 | O=C1CCSc2ccc(F)cc21>>O=C1CCSc2ccc(F)cc2N1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4072b995d7cd4225ad276ba347375802 | O=C1CCSc2ccc(F)cc2N1>>Fc1ccc2c(c1)NCCCS2 | FC=1C=CC2=C(NC(CCS2)=O)C1.COCCO[AlH2-]OCCOC.[Na+].[OH-].[Na+]>>FC=1C=CC2=C(NCCCS2)C1 | O=[C:9]1[NH:8][c:6]2[c:5]([cH:4][cH:3][c:2]([F:1])[cH:7]2)[S:12][CH2:11][CH2:10]1>>[F:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[NH:8][CH2:9][CH2:10][CH2:11][S:12]2 | O=C1CCSc2ccc(F)cc2N1 | Fc1ccc2c(c1)NCCCS2 | null | null | C1(=CC=CC=C1)C | Reduction | Reduction of secondary amides to amines | 327269ad544aa25c24fe8654d1342f272e584acd0c109aaad1c29b1e159471bb | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1ccc2c(c1)NCCCS2 | O=[C;H0;D3;+0:1](-[#7:2]-[c:3])-[C:4]-[C:5]-[#16:6]>>[#16:6]-[C:5]-[C:4]-[CH2;D2;+0:1]-[#7:2]-[c:3] | 93 | [{"value": 93.0, "product": "FC=1C=CC2=C(NCCCS2)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.2, "product": "FC=1C=CC2=C(NCCCS2)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 10 | MINUTE | 7-fluoro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one (76 mg, 0.38 mmol) dissolved in toluene (1 mL) and cooled to 0° C. in an ice bath. Red-Al (275 mL, 0.91 mmol) was added and then the reaction allowed to warm to room temperature. The reaction was heated at reflux for 1.5 hours. 1 N sodium hydoxide was added slowly until... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1ccc2c(c1)NCCCS2 | c1ccc2c(c1)NCCCS2 | c1ccc2c(c1)NCCCS2 | Other | C1(=CC=CC=C1)C | 0 | 0.166667 | O=C1CCSc2ccc(F)cc2N1>C1(=CC=CC=C1)C>Fc1ccc2c(c1)NCCCS2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2b1821aff72a4f1a911f040b4d3ed9ed | Fc1ccc2c(c1)NCCCS2>>O=NN1CCCSc2ccc(F)cc21 | FC=1C=CC2=C(NCCCS2)C1.N(=O)[O-].[Na+].O>>FC=1C=CC2=C(N(CCCS2)N=O)C1 | [NH:3]1[CH2:4][CH2:5][CH2:6][S:7][c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][c:14]21>>[O:1]=[N:2][N:3]1[CH2:4][CH2:5][CH2:6][S:7][c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][c:14]21 | Fc1ccc2c(c1)NCCCS2 | O=NN1CCCSc2ccc(F)cc21 | null | null | C(C)(=O)O | Miscellaneous | OtherReaction | e933581c68e2d2624c7bcb7a2890835c7f7022717670ab9b019ad2682d091c0d | 797765290ff12ff8fc5d8a85352c4763898223fe8d7887a890f0208d031bd39f | c1ccc2c(c1)NCCCS2 | [#16:1]-[c:2]:[c:3](:[c:4])-[NH;D2;+0:5]-[C:6]-[C:7]>>[#16:1]-[c:2]:[c:3](:[c:4])-[N;H0;D3;+0:5](-[#7:8]=[O;D1;H0:9])-[C:6]-[C:7] | 92 | [{"value": 92.0, "product": "FC=1C=CC2=C(N(CCCS2)N=O)C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 7-fluoro-2,3,4,5-tetrahydro-1,5-benzothiazepine (423 mg, 2.3 mmol) was dissolved in acetic acid (1.15 mL) at 0° C. in an ice bath. 2.7 M aqueous sodium nitrite (1 mL) was added and this was stirred over night. Water was added (100 mL) and extracted with dichloromethane (3×50 mL), the organics were combined and concentr... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Hydrazone | c1ccc2c(c1)NCCCS2 | c1ccc2c(c1)[NH]CCCS2 | c1ccc2c(c1)[NH]CCCS2 | Other | C(C)(=O)O | null | null | Fc1ccc2c(c1)NCCCS2>C(C)(=O)O>O=NN1CCCSc2ccc(F)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4e843f65c8ef4057bfad5f051d6bccd1 | O=NN1CCCSc2ccc(F)cc21>>NN1CCCSc2ccc(F)cc21 | FC=1C=CC2=C(N(CCCS2)N=O)C1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>FC=1C=CC2=C(N(CCCS2)N)C1 | O=[N:1][N:2]1[CH2:3][CH2:4][CH2:5][S:6][c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][c:13]21>>[NH2:1][N:2]1[CH2:3][CH2:4][CH2:5][S:6][c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][c:13]21 | O=NN1CCCSc2ccc(F)cc21 | NN1CCCSc2ccc(F)cc21 | null | null | C1CCOC1 | Reduction | OtherReaction | 5407f493a1ccf8dd5d07d54ae38e6a10270ea7ce5de5a6b7714c1deac546b85e | e98fc89254846fe35f9c53f13405831fb1e12dbc5358868ae840bffa7ffc2275 | c1ccc2c(c1)NCCCS2 | O=[N;H0;D2;+0:1]-[#7:2](-[C:3])-[c:4]>>[C:3]-[#7:2](-[NH2;D1;+0:1])-[c:4] | 112.6 | [{"value": 95.0, "product": "FC=1C=CC2=C(N(CCCS2)N)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 112.6, "product": "FC=1C=CC2=C(N(CCCS2)N)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | 7-fluoro-5-nitroso-2,3,4,5-tetrahydro-1,5-benzothiazepine (449 mg, 2.11 mmol) was suspended in THF (1 mL of freshly distilled) and cooled to 0° C. in an ice bath. Lithium aluminum hydride (80 mg, 2.11 mmol) was added in a portion-wise fashion. The flask was removed from the ice bath and allowed to warm to room temperat... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone | Hydrazine | null | null | c1ccc2c(c1)[NH]CCCS2 | Other | C1CCOC1 | 0 | 2 | O=NN1CCCSc2ccc(F)cc21>C1CCOC1>NN1CCCSc2ccc(F)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-acd0943576a54db99571271876df319f | CN1CCN2c3c(cccc31)C1CNCCC12.O=C(CCCCl)c1ccncc1>>CN1CCN2c3c(cccc31)[C@@H]1CN(CCCC(=O)c3ccncc3)CC[C@@H]12.Cl | ClCCCC(=O)C1=CC=NC=C1.CN1CCN2C=3C(=CC=CC13)C1C2CCNC1.N>>Cl.CN1CCN2C=3C(=CC=CC13)[C@H]1[C@@H]2CCN(C1)CCCC(=O)C1=CC=NC=C1 | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]2[c:6]3[c:7]([cH:8][cH:9][cH:10][c:11]31)[CH:12]1[CH2:13][NH:14][CH2:26][CH2:27][CH:28]21.[CH2:15]([CH2:16][CH2:17][C:18](=[O:19])[c:20]1[cH:21][cH:22][n:23][cH:24][cH:25]1)[Cl:29]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]2[c:6]3[c:7]([cH:8][cH:9][cH:10][c:11]31)[C@@H:12]1[CH2:13][N:14]([CH2:15]... | CN1CCN2c3c(cccc31)C1CNCCC12.O=C(CCCCl)c1ccncc1 | CN1CCN2c3c(cccc31)[C@@H]1CN(CCCC(=O)c3ccncc3)CC[C@@H]12.Cl | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | a97d495f7862a71e9bc2e8bc24239129fbebbff974d2ecda702b0d097e507f2e | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CCCN1CC[C@H]2[C@@H](C1)c1cccc3c1N2CCN3)c1ccncc1 | [C:1]-[C:2]-[NH;D2;+0:3]-[C:4]-[C:5].[Cl;H0;D1;+0:6]-[CH2;D2;+0:7]-[C:8]-[C:9]-[C:10]=[O;D1;H0:11]>>[C:1]-[C:2]-[N;H0;D3;+0:3](-[CH2;D2;+0:7]-[C:8]-[C:9]-[C:10]=[O;D1;H0:11])-[C:4]-[C:5].[ClH;D0;+0:6] | null | [] | null | null | null | null | The title compound was prepared from addition of the of 4-chloro-1-(4-pyridyl)butan-1-one to 3-methyl-2,3,6b,7,8,9,10,10a-octahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline following General procedure A of Example 197. 1H NMR (300 MHz, CDCl3) δ 8.79 (dd, J=4.4 Hz, 1.8 Hz, 2H), 7.74 (dd, J=4.4 Hz, 1.4 Hz, 2H), 6... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1cc2c3c(c1)C1CNCCC1N3CC[NH]2 | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC[NH]2 | c1ccncc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC[NH]2 | null | null | null | null | CN1CCN2c3c(cccc31)C1CNCCC12.O=C(CCCCl)c1ccncc1>>CN1CCN2c3c(cccc31)[C@@H]1CN(CCCC(=O)c3ccncc3)CC[C@@H]12.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c1237ae787b7416880d73365bdf5766f | CCOC(=O)N1CCc2c(c3cccc4c3n2CC(=O)N4)C1>>CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CC(=O)N3 | N1C=CC2=CC=CC=C12.[BH3-]C#N.[Na+].[OH-].[Na+].C(C)OC(=O)N1CC2=C(N3CC(NC=4C=CC=C2C34)=O)CC1.C1C(=O)NC2=CC=CC=C2N1.O=C1CCN(CC1)C(=O)OCC>>O=C1NC=2C=CC=C3C2N(C1)[C@@H]1[C@H]3CN(CC1)C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][c:9]2[c:10]([c:12]3[cH:13][cH:14][cH:15][c:16]4[c:17]3[n:18]2[CH2:19][C:20](=[O:21])[NH:22]4)[CH2:11]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][C@H:9]2[C@@H:10]([CH2:11]1)[c:12]1[cH:13][cH:14][cH:15][c:16]3[c:17]1[N:18]2[CH2:19][C:20](=[O:21])[NH:22]3 | CCOC(=O)N1CCc2c(c3cccc4c3n2CC(=O)N4)C1 | CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CC(=O)N3 | null | null | O.C(=O)(C(F)(F)F)O | Reduction | OtherReaction | 6fe5078fa337973e230c6466957c05e6e5e019f7173f54dc2b3cce93e1834287 | 3f9bd1254c561719832bd71149feb4e99c5764db1feb47bf9fbdfb1c414d602b | O=C1CN2c3c(cccc3[C@@H]3CNCC[C@@H]32)N1 | [#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[c;H0;D3;+0:6]2:[c:7](:[c:8]):[c:9]3:[c:10]-[#7:11]-[C:12](=[O;D1;H0:13])-[C:14]-[n;H0;D3;+0:15]:3:[c;H0;D3;+0:16]:2-[C:17]-[C:18]-1>>[#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C@@H;D3;+0:6]2-[C@H;D3;+0:16](-[C:17]-[C:18]-1)-[N;H0;D3;+0:15]1-[C:14]-[C:12](=[O;D1;H0:13])-[#7:11]-[... | 77 | [{"value": 77.0, "product": "O=C1NC=2C=CC=C3C2N(C1)[C@@H]1[C@H]3CN(CC1)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 4 | HOUR | The procedure described in Example 4, Steps E through G, was utilized to prepare ethyl-2-oxo-2,3,9,10-tetrahydro-1H-pyrido[3′,4′:4,5]-pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylate from the corresponding amine, 1,3,4-trihydroquinoxalin-2-one, and ethyl 4-oxopiperidinecarboxylate. This indole (5.74 g, 19.2 mmol) was dis... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1cc2c3c(c1)c1c(n3CCN2)CC[NH]C1 | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCN2 | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCN2 | null | O.C(=O)(C(F)(F)F)O | 0 | 4 | CCOC(=O)N1CCc2c(c3cccc4c3n2CC(=O)N4)C1>O.C(=O)(C(F)(F)F)O>CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CC(=O)N3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-12df34174e834b04869816319f84fd12 | CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CC(=O)N3>>CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CCN3 | [OH-].[Na+].C(C)OC(=O)N1C[C@@H]2[C@@H](N3CC(NC=4C=CC=C2C34)=O)CC1>>C1CNC=2C=CC=C3C2N1[C@@H]1[C@H]3CN(CC1)C(=O)OCC | O=[C:20]1[CH2:19][N:18]2[C@H:9]3[CH2:8][CH2:7][N:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:11][C@H:10]3[c:12]3[cH:13][cH:14][cH:15][c:16]([c:17]32)[NH:21]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][C@H:9]2[C@@H:10]([CH2:11]1)[c:12]1[cH:13][cH:14][cH:15][c:16]3[c:17]1[N:18]2[CH2:19][CH2:20][NH:21]3 | CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CC(=O)N3 | CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CCN3 | null | null | Cl | Reduction | Reduction of secondary amides to amines | 3fc258628225fc072bacea46d1ccbddbad979132c401173fe10d2fa5f864f536 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCN2 | O=[C;H0;D3;+0:1]1-[#7:2]-[c:3]:[c:4]-[#7:5](-[C:6])-[C:7]-1>>[C:6]-[#7:5]1-[C:7]-[CH2;D2;+0:1]-[#7:2]-[c:3]:[c:4]-1 | 98 | [{"value": 98.0, "product": "C1CNC=2C=CC=C3C2N1[C@@H]1[C@H]3CN(CC1)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.7, "product": "C1CNC=2C=CC=C3C2N1[C@@H]1[C@H]3CN(CC1)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To ethyl-(6bR,10aS)-2-oxo-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylate (4.41 g, 14.6 mmol) was added 1M BH3 THF complex solution (36.6 mL). The reaction was heated under reflux for 5 hr. After the reaction cooled down to r.t, 6N HCl (40 mL) was added dropwise with chillin... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCN2 | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCN2 | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCN2 | Other | Cl | null | null | CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CC(=O)N3>Cl>CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CCN3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-381d5b1427f5455c8194fd5d9e7a1e45 | CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CCN3>>c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCN2 | C1CNC=2C=CC=C3C2N1[C@@H]1[C@H]3CN(CC1)C(=O)OCC.[OH-].[K+]>>C1CNC=2C=CC=C3C2N1[C@@H]1[C@H]3CNCC1 | CCOC(=O)[N:9]1[CH2:8][C@H:7]2[c:5]3[c:4]4[c:3]([cH:2][cH:1][cH:6]3)[NH:16][CH2:15][CH2:14][N:13]4[C@H:12]2[CH2:11][CH2:10]1>>[cH:1]1[cH:2][c:3]2[c:4]3[c:5]([cH:6]1)[C@@H:7]1[CH2:8][NH:9][CH2:10][CH2:11][C@@H:12]1[N:13]3[CH2:14][CH2:15][NH:16]2 | CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CCN3 | c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCN2 | null | null | C(CCC)O | Reduction | Hydrogenolysis of tertiary amines | a9ee7e2fb016852f1063ead53001c74f536ec15fff5e5d851222774ac6dbe6b7 | 20c36f41eeb07c3ba4437b51ba72e8ff3c22d0b27e7197b0e9af3127f331149f | c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCN2 | 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] | 87.7 | [{"value": 78.0, "product": "C1CNC=2C=CC=C3C2N1[C@@H]1[C@H]3CNCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.7, "product": "C1CNC=2C=CC=C3C2N1[C@@H]1[C@H]3CNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 119 | CELSIUS | null | null | To ethyl (6bR,10aS)-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylate (4.10 g, 14.3 mmol) was added n-butanol (18.0 mL) and KOH powder (3.0 g). The reaction was heated at 119° C. in a sealed tube for 18 hr. The solvent was removed under reduced pressure. To the residue was add... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Secondary amine | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCN2 | c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCN2 | c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCN2 | HO- | C(CCC)O | 119 | null | CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CCN3>C(CCC)O>c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCN2 |
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