dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bff2a076ce534e20a3ef04c541e07fc6 | N.O=C(NS(=O)(=O)c1ccc(Cl)c([N+](=O)[O-])c1)c1ccc(-c2ccc(F)cc2)cc1>>Nc1ccc(S(=O)(=O)NC(=O)c2ccc(-c3ccc(F)cc3)cc2)cc1[N+](=O)[O-] | ClC1=C(C=C(C=C1)S(=O)(=O)NC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)F)[N+](=O)[O-].N>>NC1=C(C=C(C=C1)S(=O)(=O)NC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)F)[N+](=O)[O-] | [NH3:1].Cl[c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[NH:9][C:10](=[O:11])[c:12]2[cH:13][cH:14][c:15](-[c:16]3[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]3)[cH:23][cH:24]2)[cH:25][c:26]1[N+:27](=[O:28])[O-:29]>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[NH:9][C:10](=[O:11])[c:12]2[cH:13][cH:14][c:15](-[c:16]3... | N.O=C(NS(=O)(=O)c1ccc(Cl)c([N+](=O)[O-])c1)c1ccc(-c2ccc(F)cc2)cc1 | Nc1ccc(S(=O)(=O)NC(=O)c2ccc(-c3ccc(F)cc3)cc2)cc1[N+](=O)[O-] | null | null | CO.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 5cea7b75c7f95cc50fd74029efa1cddce51f01200160afa4aaecfa45e52a1621 | c5668f64a1395fa45312378ed819baaeafc354cdb673b20226ea2853ed14db5d | O=C(NS(=O)(=O)c1ccccc1)c1ccc(-c2ccccc2)cc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[NH3;D0;+0:7]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH2;D1;+0:7]):[c:2]:[c:3] | null | [] | 0 | CELSIUS | null | null | A solution of Example 1D (1.0 g) in methanol (10 mL) and concentrated aqueous ammonia (3 mL) was heated in a sealed pressure tube to 60° C. for 16 hours, cooled to 0° C., diluted with ethyl acetate (100 mL), washed with water (30 mL) and brine (10 mL), dried (MgSO4), filtered, and concentrated to provide the desired pr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Primary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | HCl | CO.C(C)(=O)OCC | 0 | null | N.O=C(NS(=O)(=O)c1ccc(Cl)c([N+](=O)[O-])c1)c1ccc(-c2ccc(F)cc2)cc1>CO.C(C)(=O)OCC>Nc1ccc(S(=O)(=O)NC(=O)c2ccc(-c3ccc(F)cc3)cc2)cc1[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8d3b28bfd0764d53ae5724cb43a3f362 | Nc1ccc(S(=O)(=O)NC(=O)c2ccc(-c3ccc(F)cc3)cc2)cc1[N+](=O)[O-].O=C(Cl)C12CC3CC(CC(C3)C1)C2>>O=C(NS(=O)(=O)c1ccc(NC(=O)C23CC4CC(CC(C4)C2)C3)c([N+](=O)[O-])c1)c1ccc(-c2ccc(F)cc2)cc1 | C12(CC3CC(CC(C1)C3)C2)C(=O)Cl.NC1=C(C=C(C=C1)S(=O)(=O)NC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)F)[N+](=O)[O-].[H-].[Na+].Cl>>FC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)NS(=O)(=O)C1=CC(=C(C=C1)NC(=O)C12CC3CC(CC(C1)C3)C2)[N+](=O)[O-] | [O:1]=[C:2]([NH:3][S:4](=[O:5])(=[O:6])[c:7]1[cH:8][cH:9][c:10]([NH2:11])[c:24]([N+:25](=[O:26])[O-:27])[cH:28]1)[c:29]1[cH:30][cH:31][c:32](-[c:33]2[cH:34][cH:35][c:36]([F:37])[cH:38][cH:39]2)[cH:40][cH:41]1.Cl[C:12](=[O:13])[C:14]12[CH2:15][CH:16]3[CH2:17][CH:18]([CH2:19][CH:20]([CH2:21]3)[CH2:22]1)[CH2:23]2>>[O:1]=[... | Nc1ccc(S(=O)(=O)NC(=O)c2ccc(-c3ccc(F)cc3)cc2)cc1[N+](=O)[O-].O=C(Cl)C12CC3CC(CC(C3)C1)C2 | O=C(NS(=O)(=O)c1ccc(NC(=O)C23CC4CC(CC(C4)C2)C3)c([N+](=O)[O-])c1)c1ccc(-c2ccc(F)cc2)cc1 | null | null | O1CCOCC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NS(=O)(=O)c1ccc(NC(=O)C23CC4CC(CC(C4)C2)C3)cc1)c1ccc(-c2ccccc2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C:5])-[C:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10])(-[C:5])-[C:6] | null | [] | null | null | 30 | MINUTE | A solution of Example 380A (101 mg, 0.25 mmol) in TBF (3 mL) was treated with 60% sodium hydride in oil (40 mg, 1.0 mmol), stirred for 30 minutes, treated with 1-adamantanecarbonyl chloride (60 mg, 0.30 mmol), stirred for 30 minutes, adjusted to pH<7 with 4M HCl in dioxane (0.5 mL), filtered, and concentrated. The conc... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccccc1.C1C2CC3CC1CC(C2)C3 | HCl | O1CCOCC1 | null | 0.5 | Nc1ccc(S(=O)(=O)NC(=O)c2ccc(-c3ccc(F)cc3)cc2)cc1[N+](=O)[O-].O=C(Cl)C12CC3CC(CC(C3)C1)C2>O1CCOCC1>O=C(NS(=O)(=O)c1ccc(NC(=O)C23CC4CC(CC(C4)C2)C3)c([N+](=O)[O-])c1)c1ccc(-c2ccc(F)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5097bcb7a27844ffac144da89958c1e3 | COC(=O)c1ccc(B(O)O)cc1.Cc1c(C#N)sc2ccc(Cl)cc12>>COC(=O)c1ccc(-c2ccc3sc(C#N)c(C)c3c2)cc1 | ClC=1C=CC2=C(C(=C(S2)C#N)C)C1.COC(=O)C1=CC=C(C=C1)B(O)O.C(C)(C)(C)P(C1=C(C=CC=C1)C1=CC=CC=C1)C(C)(C)C.[F-].[K+]>>C(#N)C=1SC2=C(C1C)C=C(C=C2)C2=CC=C(C(=O)OC)C=C2 | OB(O)[c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:22][cH:21]1.Cl[c:9]1[cH:10][cH:11][c:12]2[s:13][c:14]([C:15]#[N:16])[c:17]([CH3:18])[c:19]2[cH:20]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]3[s:13][c:14]([C:15]#[N:16])[c:17]([CH3:18])[c:19]3[cH:20]2)[cH:21][cH:22]1 | COC(=O)c1ccc(B(O)O)cc1.Cc1c(C#N)sc2ccc(Cl)cc12 | COC(=O)c1ccc(-c2ccc3sc(C#N)c(C)c3c2)cc1 | null | CC(=O)[O-].CC(=O)[O-].[Pd+2] | C1CCOC1 | C-C Coupling | Suzuki coupling with boronic acids | a1259a94b31ac9f1988cb839e0910c5b2437b7522341904299ff46277eacea87 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc3sccc3c2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#16;a:5]):[c:6]:[c:7]:1.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#16;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:7]:[c:6]:1 | null | [] | null | null | null | null | A mixture of Example 401A (557 mg, 2.68 mmol), (4-methoxycarbonylphenyl)-boronic acid (675 mg, 3.75 mmol), Pd(OAc)2 (36 mg, 0.16 mmol), 2-(di-tert-butylphosphino)biphenyl (63 mg, 0.21 mmol), and KF (467 mg, 8.04 mmol) in THF (10mL) was heated to 60° C. for 16 hours and concentrated The concentrate was purified by flash... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2sccc2c1 | c1ccccc1.c1ccc2sccc2c1 | c1ccccc1.c1ccc2sccc2c1 | HCl.B | CC(=O)[O-].CC(=O)[O-].[Pd+2].C1CCOC1 | null | null | COC(=O)c1ccc(B(O)O)cc1.Cc1c(C#N)sc2ccc(Cl)cc12>CC(=O)[O-].CC(=O)[O-].[Pd+2].C1CCOC1>COC(=O)c1ccc(-c2ccc3sc(C#N)c(C)c3c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1ce22d6cab7d4438bd93a5a0416d7bf2 | CI.COC(=O)c1ccc(-c2ccc(CO)cc2OC)cc1>>COCc1ccc(-c2ccc(C(=O)OC)cc2)c(OC)c1 | OCC1=CC(=C(C=C1)C1=CC=C(C=C1)C(=O)OC)OC.[H-].[Na+].CI.Cl>>COC1=C(C=CC(=C1)COC)C1=CC=C(C=C1)C(=O)OC | I[CH3:1].[OH:2][CH2:3][c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([C:12](=[O:13])[O:14][CH3:15])[cH:16][cH:17]2)[c:18]([O:19][CH3:20])[cH:21]1>>[CH3:1][O:2][CH2:3][c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([C:12](=[O:13])[O:14][CH3:15])[cH:16][cH:17]2)[c:18]([O:19][CH3:20])[cH:21]1 | CI.COC(=O)c1ccc(-c2ccc(CO)cc2OC)cc1 | COCc1ccc(-c2ccc(C(=O)OC)cc2)c(OC)c1 | null | null | O1CCOCC1.C1CCOC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 31b37b19ff6de58cf584e89bae19f862b01d058b473835fea10bbd4c0a53fd14 | f3e76c16e7df5a83f618c93f8745117d548e410efce45e89753f2c180a9b20f8 | c1ccc(-c2ccccc2)cc1 | I-[CH3;D1;+0:1].[OH;D1;+0:2]-[C:3]-[c:4]>>[CH3;D1;+0:1]-[O;H0;D2;+0:2]-[C:3]-[c:4] | null | [] | null | null | 30 | MINUTE | A solution of Example 417A (142 mg, 0.5 mmol) in THF (3 mL) at room temperature was treated with 60% sodium hydride in oil (40 mg, 1.0 mmol) and methyl iodide (0.30 mmol), stirred for 30 minutes, adjusted to pH<7 with 4M HCl in dioxane (0.5 mL), filtered, and concentrated. The concentrate was purified by flash column c... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HI | O1CCOCC1.C1CCOC1 | null | 0.5 | CI.COC(=O)c1ccc(-c2ccc(CO)cc2OC)cc1>O1CCOCC1.C1CCOC1>COCc1ccc(-c2ccc(C(=O)OC)cc2)c(OC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7b00705408e44469941c490f5be2f99e | COC(=O)c1ccc(C2=CCC3(CC2)OCCO3)cc1>>COC(=O)c1ccc(C2=CCC(=O)CC2)cc1 | O1CCOC12CC=C(CC2)C2=CC=C(C(=O)OC)C=C2.C1(=CC=C(C=C1)S(=O)(=O)O)C>>O=C1CC=C(CC1)C1=CC=C(C(=O)OC)C=C1 | C1C[O:13][C:12]2(O1)[CH2:11][CH:10]=[C:9]([c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:17][cH:16]1)[CH2:15][CH2:14]2>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9]2=[CH:10][CH2:11][C:12](=[O:13])[CH2:14][CH2:15]2)[cH:16][cH:17]1 | COC(=O)c1ccc(C2=CCC3(CC2)OCCO3)cc1 | COC(=O)c1ccc(C2=CCC(=O)CC2)cc1 | null | null | CC(=O)C | Miscellaneous | Ketal hydrolysis to ketone | 28bfec55e245adc574605e1d0e9aea134d32b54ad000fbfecce09d058b7f56f3 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1CC=C(c2ccccc2)CC1 | [c:1]-[C:2]1=[C:3]-[C:4]-[C;H0;D4;+0:5]2(-O-C-C-[O;H0;D2;+0:6]-2)-[C:7]-[C:8]-1>>[O;H0;D1;+0:6]=[C;H0;D3;+0:5]1-[C:4]-[C:3]=[C:2](-[c:1])-[C:8]-[C:7]-1 | null | [] | null | null | null | null | A solution of Example 420B (2.2 g) and p-toluenesulfonic acid (100 mg) in acetone (10 mL) was heated to reflux for 10 hours, filtered through a pad of silica gel (20 g), and concentrated to provide the desired product.
Conditions: See reaction.notes.procedure_details.
Workup: to reflux for 10 hours; filtered through a ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1=CCC2(CC1)OCCO2 | C1=CCCCC1 | c1ccccc1.C1=CCCCC1 | HO- | CC(=O)C | null | null | COC(=O)c1ccc(C2=CCC3(CC2)OCCO3)cc1>CC(=O)C>COC(=O)c1ccc(C2=CCC(=O)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-21e914593c374e0cac9a20bb9660e89a | COC(=O)c1ccc(C2=CCC(=O)CC2)cc1>>COC(=O)c1ccc(C2=CCC(C)(O)CC2)cc1 | O=C1CC=C(CC1)C1=CC=C(C(=O)OC)C=C1.C[Li].[Cl-].[Ce+3].[Cl-].[Cl-].[Cl-].[Li+]>>OC1(CC=C(CC1)C1=CC=C(C(=O)OC)C=C1)C | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9]2=[CH:10][CH2:11][C:12](=[O:14])[CH2:15][CH2:16]2)[cH:17][cH:18]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9]2=[CH:10][CH2:11][C:12]([CH3:13])([OH:14])[CH2:15][CH2:16]2)[cH:17][cH:18]1 | COC(=O)c1ccc(C2=CCC(=O)CC2)cc1 | COC(=O)c1ccc(C2=CCC(C)(O)CC2)cc1 | null | null | C(C)(=O)OCC.C(C)OCC.C1CCOC1 | Miscellaneous | OtherReaction | 82f307c2771f24472352179bfdcbd50ca1b6a8d7cf7b2748b565724a523407a8 | 8811b4d793f7cfa9f0f1f47a008648edabb54f371f76dfa680dd5b2e1564c6c5 | C1=C(c2ccccc2)CCCC1 | [O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:3]-[C:4]=[C:5](-[c:6])-[C:7]-[C:8]-1>>[C;D1;H3:9]-[C;H0;D4;+0:2]1(-[OH;D1;+0:1])-[C:3]-[C:4]=[C:5](-[c:6])-[C:7]-[C:8]-1 | null | [] | null | null | null | null | A suspension of anhydrous cerium(III) chloride (2.71 g, 11 mmol) in THF (10 mL) at −78° C. was slowly treated with 1.5M methyllithium complexed with lithium chloride in diethyl ether (6.7 mL), warmed to room temperature over 2 hours, and added to a solution of Example 420C (1.15 g, 5.0mmol) in THF (10 mL) at −78° C. Th... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol | C1=CCCCC1 | C1=CCCCC1 | c1ccccc1.C1=CCCCC1 | Other | C(C)(=O)OCC.C(C)OCC.C1CCOC1 | null | null | COC(=O)c1ccc(C2=CCC(=O)CC2)cc1>C(C)(=O)OCC.C(C)OCC.C1CCOC1>COC(=O)c1ccc(C2=CCC(C)(O)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b476166e14714a7e91095eac307ce4e4 | COC(=O)[C@H](CSc1ccccc1)Nc1ccc(S(N)(=O)=O)cc1[N+](=O)[O-]>>NS(=O)(=O)c1ccc(NC(CO)CSc2ccccc2)c([N+](=O)[O-])c1 | NS(=O)(=O)C1=CC(=C(C=C1)N[C@@H](CSC1=CC=CC=C1)C(=O)OC)[N+](=O)[O-].[BH4-].[Li+]>>OCC(CSC1=CC=CC=C1)NC1=C(C=C(C=C1)S(=O)(=O)N)[N+](=O)[O-] | CO[C:11]([C@@H:10]([NH:9][c:8]1[cH:7][cH:6][c:5]([S:2]([NH2:1])(=[O:3])=[O:4])[cH:25][c:21]1[N+:22](=[O:23])[O-:24])[CH2:13][S:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)=[O:12]>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][CH:10]([CH2:11][OH:12])[CH2:13][S:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20... | COC(=O)[C@H](CSc1ccccc1)Nc1ccc(S(N)(=O)=O)cc1[N+](=O)[O-] | NS(=O)(=O)c1ccc(NC(CO)CSc2ccccc2)c([N+](=O)[O-])c1 | null | null | CO.C(C)(=O)OCC.C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(NCCSc2ccccc2)cc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C@@H;D3;+0:3](-[#7:4]-[c:5])-[C:6]-[#16:7]>>[#16:7]-[C:6]-[CH;D3;+0:3](-[#7:4]-[c:5])-[CH2;D2;+0:1]-[OH;D1;+0:2] | null | [] | null | null | 3 | HOUR | A solution of Example 434A (1.42 g, 3.45 mmol) in THF (10 mL) and methanol (1 mL) at room temperature was slowly treated with lithium borohydride (100 mg), stirred for 3 hours, as diluted with ethyl acetate (100 mL), washed with water (45 mL) and brine (10 mL), dried (MgSO4), filtered, and concentrated to provide the d... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.c1ccccc1 | Other | CO.C(C)(=O)OCC.C1CCOC1 | null | 3 | COC(=O)[C@H](CSc1ccccc1)Nc1ccc(S(N)(=O)=O)cc1[N+](=O)[O-]>CO.C(C)(=O)OCC.C1CCOC1>NS(=O)(=O)c1ccc(NC(CO)CSc2ccccc2)c([N+](=O)[O-])c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-87ebc5f3cd504bc8920c2b08ab1bf8b6 | NS(=O)(=O)c1ccc(NC(CO)CSc2ccccc2)c([N+](=O)[O-])c1.[N-]=[N+]=[N-]>>[N-]=[N+]=NCC(CSc1ccccc1)Nc1ccc(S(N)(=O)=O)cc1[N+](=O)[O-] | OCC(CSC1=CC=CC=C1)NC1=C(C=C(C=C1)S(=O)(=O)N)[N+](=O)[O-].C(C)(C)N(C(C)C)CC.CS(=O)(=O)Cl.[N-]=[N+]=[N-].[Na+]>>N(=[N+]=[N-])CC(CSC1=CC=CC=C1)NC1=C(C=C(C=C1)S(=O)(=O)N)[N+](=O)[O-] | O[CH2:4][CH:5]([CH2:6][S:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[NH:14][c:15]1[cH:16][cH:17][c:18]([S:19]([NH2:20])(=[O:21])=[O:22])[cH:23][c:24]1[N+:25](=[O:26])[O-:27].[N-:1]=[N+:2]=[N-:3]>>[N-:1]=[N+:2]=[N:3][CH2:4][CH:5]([CH2:6][S:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[NH:14][c:15]1[cH:16][cH:17][c:18]([... | NS(=O)(=O)c1ccc(NC(CO)CSc2ccccc2)c([N+](=O)[O-])c1.[N-]=[N+]=[N-] | [N-]=[N+]=NCC(CSc1ccccc1)Nc1ccc(S(N)(=O)=O)cc1[N+](=O)[O-] | null | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC | ClCCl.CN(C)C=O.C(C)(=O)OCC | Functional Group Addition | OtherReaction | f9a80609465600bf0decaa33fd5de5feaf004c5d380786fc66eb0efb9e034bbe | 9decb3955913485691906a27715d754335868709c17a134aab1e5b87ceb0a1d6 | c1ccc(NCCSc2ccccc2)cc1 | O-[CH2;D2;+0:1]-[C:2](-[#7:3])-[C:4].[N-;H0;D1:5]=[#7;+:6]=[N;-;D1;H0:7]>>[#7:3]-[C:2](-[C:4])-[CH2;D2;+0:1]-[N;H0;D2;+0:5]=[#7;+:6]=[N;-;D1;H0:7] | null | [] | 50 | CELSIUS | 1 | HOUR | A solution of Example 434B (1.01 g, 2.6 mmol) and N,N-diisopropylethylamine (0.70 mL, 4.0 mmol) in dichloromethane (5 mL) and DMF (5 mL) at room temperature was treated with methanesulfonyl chloride (0.22 mL, 2.90 mmol), stirred for 1 hour, and concentrated to remove the dichloromethane. The resulting DMF solution was ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Azide | null | null | c1ccccc1.c1ccccc1 | HO- | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC.ClCCl.CN(C)C=O.C(C)(=O)OCC | 50 | 1 | NS(=O)(=O)c1ccc(NC(CO)CSc2ccccc2)c([N+](=O)[O-])c1.[N-]=[N+]=[N-]>[I-].C(CCC)[N+](CCCC)(CCCC)CCCC.ClCCl.CN(C)C=O.C(C)(=O)OCC>[N-]=[N+]=NCC(CSc1ccccc1)Nc1ccc(S(N)(=O)=O)cc1[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-333c17c03f8044eb9956ea3aae74859d | BrCc1ccccc1.COC(=O)C(CO)NC(=O)OC(C)(C)C>>COC(=O)[C@H](COCc1ccccc1)NC(=O)OC(C)(C)C | N(C(CO)C(=O)OC)C(=O)OC(C)(C)C.C(C1=CC=CC=C1)Br>>C(C1=CC=CC=C1)OC[C@H](NC(=O)OC(C)(C)C)C(=O)OC | Br[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][OH:7])[NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22]>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][O:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22] | BrCc1ccccc1.COC(=O)C(CO)NC(=O)OC(C)(C)C | COC(=O)[C@H](COCc1ccccc1)NC(=O)OC(C)(C)C | null | [Ag]=O | ClCCl | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]-[C:9]-[OH;D1;+0:10]>>[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]-[C:9]-[O;H0;D2;+0:10]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 2 | DAY | A mixture of BOC-DL-Ser-OMe (434 mg, 2.0 mmol), benzyl bromide (513 mg, 3.0 mmol), and silver oxide (695 mg, 3.0 mmol) in dichloromethane (10 mL) at room temperature was stirred for 2 days, filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 20% ethyl acetate/hexan... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | c1ccccc1 | HBr | [Ag]=O.ClCCl | null | 48 | BrCc1ccccc1.COC(=O)C(CO)NC(=O)OC(C)(C)C>[Ag]=O.ClCCl>COC(=O)[C@H](COCc1ccccc1)NC(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cb05855d74514f13ba559f79a9468752 | COC(=O)c1ccc(-c2ccc(C=O)cc2OC)cc1.C[Si](C)(C)[N-][Si](C)(C)C>>C=Cc1ccc(-c2ccc(C(=O)OC)cc2)c(OC)c1 | C(=O)C1=CC(=C(C=C1)C1=CC=C(C=C1)C(=O)OC)OC.C[Si](C)(C)[N-][Si](C)(C)C.[Li+]>>COC1=C(C=CC(=C1)C=C)C1=CC=C(C=C1)C(=O)OC | O=[CH:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C:11](=[O:12])[O:13][CH3:14])[cH:15][cH:16]2)[c:17]([O:18][CH3:19])[cH:20]1.C[Si](C)(C)[N-][Si](C)(C)[CH3:1]>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C:11](=[O:12])[O:13][CH3:14])[cH:15][cH:16]2)[c:17]([O:18][CH3:19])[cH:20]1 | COC(=O)c1ccc(-c2ccc(C=O)cc2OC)cc1.C[Si](C)(C)[N-][Si](C)(C)C | C=Cc1ccc(-c2ccc(C(=O)OC)cc2)c(OC)c1 | null | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | C1CCOC1 | C-C Coupling | OtherReaction | 65846b40393caf810f4a2d80980311afbe6a487d5b2731f135215f55a25e4832 | 37f02ff997533d11a1e569347ef78cf65235ab0024b34a145afdaafd2d3d15ac | c1ccc(-c2ccccc2)cc1 | C-[Si](-C)(-C)-[N-]-[Si](-C)(-C)-[CH3;D1;+0:1].O=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[CH2;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | 30 | MINUTE | A suspension of methyltriphenylphosphonium bromide (785 mg, 2.2 mmoL) in THF (5 mL) was treated with 1M lithium bis(trimethylsilyl)amide in THF (2.2 mL), stirred for 30 minutes, treated with a solution of Example 122I (540 mg, 2.0 mmol) in TB (2 mL), stirred for 1 hour, and filtered through a pad of silica gel (20 g). ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Silyl protective group.Silyl protective group | Vinyl | null | null | c1ccccc1.c1ccccc1 | HO- | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C1CCOC1 | null | 0.5 | COC(=O)c1ccc(-c2ccc(C=O)cc2OC)cc1.C[Si](C)(C)[N-][Si](C)(C)C>[Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C1CCOC1>C=Cc1ccc(-c2ccc(C(=O)OC)cc2)c(OC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-68ccfbd23c22430fbe233f1b14b1e167 | C=Cc1ccc(-c2ccc(C(=O)OC)cc2)c(OC)c1.OO>>COC(=O)c1ccc(-c2ccc(CCO)cc2OC)cc1 | COC1=C(C=CC(=C1)C=C)C1=CC=C(C=C1)C(=O)OC.B.C([O-])([O-])=O.[Na+].[Na+].OO>>OCCC1=CC(=C(C=C1)C1=CC=C(C=C1)C(=O)OC)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([CH:13]=[CH2:14])[cH:16][c:17]2[O:18][CH3:19])[cH:20][cH:21]1.O[OH:15]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([CH2:13][CH2:14][OH:15])[cH:16][c:17]2[O:18][CH3:19])[cH:20][cH:21]1 | C=Cc1ccc(-c2ccc(C(=O)OC)cc2)c(OC)c1.OO | COC(=O)c1ccc(-c2ccc(CCO)cc2OC)cc1 | null | null | C(C)(=O)OCC.C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 6aaa6688cc4965019d9400c93c20e1d817a445418a6601722f66df7d420427e9 | 4ceb30033bcfd57c382fe05e353b68e7f657859dbacaaa785451a244b2657476 | c1ccc(-c2ccccc2)cc1 | O-[OH;D1;+0:1].[CH2;D1;+0:2]=[CH;D2;+0:3]-[c:4](:[c:5]):[c:6]>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[c:4](:[c:5]):[c:6] | null | [] | 60 | CELSIUS | null | null | A solution of Example 445A (228 mg) and 1M borane in THF (1.2 mL) in THF (2 mL) at room temperature was stirred for 5 hours, and treated sequentially with 2M sodium carbonate (1 mL) and 33% hydrogen peroxide (1 mL). The mixture was heated to 60° C. for 1 hour, diluted with ethyl acetate (100 mL), washed with water (45 ... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide.Vinyl | Primary alcohol | null | null | c1ccccc1.c1ccccc1 | Other | C(C)(=O)OCC.C1CCOC1 | 60 | null | C=Cc1ccc(-c2ccc(C(=O)OC)cc2)c(OC)c1.OO>C(C)(=O)OCC.C1CCOC1>COC(=O)c1ccc(-c2ccc(CCO)cc2OC)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a6219332344d417b859e800de0151d39 | COC(=O)c1ccc(-c2ccc(CCCO[Si](C)(C)C(C)(C)C)cc2OC)cc1>>COc1cc(CCCO[Si](C)(C)C(C)(C)C)ccc1-c1ccc(C(=O)O)cc1 | [Si](C)(C)(C(C)(C)C)OCCCC1=CC(=C(C=C1)C1=CC=C(C=C1)C(=O)OC)OC.[Li+].[OH-]>>[Si](C)(C)(C(C)(C)C)OCCCC1=CC(=C(C=C1)C1=CC=C(C=C1)C(=O)O)OC | C[O:26][C:24]([c:23]1[cH:22][cH:21][c:20](-[c:19]2[c:3]([O:2][CH3:1])[cH:4][c:5]([CH2:6][CH2:7][CH2:8][O:9][Si:10]([CH3:11])([CH3:12])[C:13]([CH3:14])([CH3:15])[CH3:16])[cH:17][cH:18]2)[cH:28][cH:27]1)=[O:25]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][CH2:7][CH2:8][O:9][Si:10]([CH3:11])([CH3:12])[C:13]([CH3:14])([CH3:15])[... | COC(=O)c1ccc(-c2ccc(CCCO[Si](C)(C)C(C)(C)C)cc2OC)cc1 | COc1cc(CCCO[Si](C)(C)C(C)(C)C)ccc1-c1ccc(C(=O)O)cc1 | null | null | C(C)(=O)OCC.C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2ccccc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | 3 | HOUR | A mixture of Example 451A (828 mg, 2.0 mmol) and 1M LiOH (3 mL) in THF (10 mL) was heated to 50° C., stirred for 3 hours, diluted with ethyl acetate, washed with saturated sodium monobasic phosphate (10 mL), dried (MgSO4), filtered, and concentrated to provide the desired product.
Conditions: See reaction.notes.procedu... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | Other | C(C)(=O)OCC.C1CCOC1 | null | 3 | COC(=O)c1ccc(-c2ccc(CCCO[Si](C)(C)C(C)(C)C)cc2OC)cc1>C(C)(=O)OCC.C1CCOC1>COc1cc(CCCO[Si](C)(C)C(C)(C)C)ccc1-c1ccc(C(=O)O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f393d314843f45daae93ff7e9eb80178 | COC(=O)c1ccc(C2=CCN(C(=O)OC(C)(C)C)CC2)cc1.NS(=O)(=O)c1ccc(NCCSc2ccccc2)c([N+](=O)[O-])c1>>CC(C)(C)OC(=O)N1CC=C(c2ccc(C(=O)NS(=O)(=O)c3ccc(NCCSc4ccccc4)c([N+](=O)[O-])c3)cc2)CC1 | [N+](=O)([O-])C=1C=C(C=CC1NCCSC1=CC=CC=C1)S(=O)(=O)N.CCN=C=NCCCN(C)C.COC(=O)C1=CC=C(C=C1)C=1CCN(CC1)C(=O)OC(C)(C)C.[Li+].[OH-]>>[N+](=O)([O-])C=1C=C(C=CC1NCCSC1=CC=CC=C1)S(=O)(=O)NC(=O)C1=CC=C(C=C1)C=1CCN(CC1)C(=O)OC(C)(C)C | CO[C:16]([c:15]1[cH:14][cH:13][c:12]([C:11]2=[CH:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:44][CH2:43]2)[cH:42][cH:41]1)=[O:17].[NH2:18][S:19](=[O:20])(=[O:21])[c:22]1[cH:23][cH:24][c:25]([NH:26][CH2:27][CH2:28][S:29][c:30]2[cH:31][cH:32][cH:33][cH:34][cH:35]2)[c:36]([N+:37](=[O:38])[O-:39])... | COC(=O)c1ccc(C2=CCN(C(=O)OC(C)(C)C)CC2)cc1.NS(=O)(=O)c1ccc(NCCSc2ccccc2)c([N+](=O)[O-])c1 | CC(C)(C)OC(=O)N1CC=C(c2ccc(C(=O)NS(=O)(=O)c3ccc(NCCSc4ccccc4)c([N+](=O)[O-])c3)cc2)CC1 | null | CN(C)C=1C=CN=CC1 | O.C(C)(=O)OCC.ClC(C)Cl.CO.C1CCOC1 | Acylation | Aminolysis of esters | 5894ae7814242c4644e19aff394b08853b52e43b2f0bde0de031dced0ee91450 | 2dc8f17ecc2e722c5c3a62b720a5408c74a550fd92fbcd682ac09cdbc0305937 | O=C(NS(=O)(=O)c1ccc(NCCSc2ccccc2)cc1)c1ccc(C2=CCNCC2)cc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[#16:7](=[O;D1;H0:8])(=[O;D1;H0:9])-[c:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[#16:7](=[O;D1;H0:8])(=[O;D1;H0:9])-[c:10])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 16 | HOUR | A mixture of Example 455B (1 g, 3.1 mmol) and LiOH (0.264 mg 6.2 mmol) in THF (15 mL), methanol (2.5 mL), and water (1.5 mL) was heated to 50° C. for 3 hours and concentrated. The concentrate was dissolved in DMF (10 mL) and treated with a mixture of Example 77B (1.059 g, 3mmol), EDCI (1.146 g, 6 mmol), and DMAP (1.830... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Ester | Sulfonamide.Secondary amide | null | null | C1=CC[NH]CC1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | CN(C)C=1C=CN=CC1.O.C(C)(=O)OCC.ClC(C)Cl.CO.C1CCOC1 | null | 16 | COC(=O)c1ccc(C2=CCN(C(=O)OC(C)(C)C)CC2)cc1.NS(=O)(=O)c1ccc(NCCSc2ccccc2)c([N+](=O)[O-])c1>CN(C)C=1C=CN=CC1.O.C(C)(=O)OCC.ClC(C)Cl.CO.C1CCOC1>CC(C)(C)OC(=O)N1CC=C(c2ccc(C(=O)NS(=O)(=O)c3ccc(NCCSc4ccccc4)c([N+](=O)[O-])c3)cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-35b3679ab5b0449ea4e1d0eaec1f9fdb | N#C[O-].NCCCC[C@H](CSc1ccccc1)Nc1ccc(S(=O)(=O)NC(=O)c2ccc(N3CCC4(CCCC4)CC3)cc2)cc1[N+](=O)[O-]>>NC(=O)NCCCC[C@H](CSc1ccccc1)Nc1ccc(S(=O)(=O)NC(=O)c2ccc(N3CCC4(CCCC4)CC3)cc2)cc1[N+](=O)[O-] | NCCCC[C@H](CSC1=CC=CC=C1)NC1=C(C=C(C=C1)S(=O)(=O)NC(C1=CC=C(C=C1)N1CCC2(CCCC2)CC1)=O)[N+](=O)[O-].[O-]C#N.[K+].O>>NC(=O)NCCCC[C@H](CSC1=CC=CC=C1)NC1=C(C=C(C=C1)S(=O)(=O)NC(C1=CC=C(C=C1)N1CCC2(CCCC2)CC1)=O)[N+](=O)[O-] | [N:1]#[C:2][O-:3].[NH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C@H:9]([CH2:10][S:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[NH:18][c:19]1[cH:20][cH:21][c:22]([S:23](=[O:24])(=[O:25])[NH:26][C:27](=[O:28])[c:29]2[cH:30][cH:31][c:32]([N:33]3[CH2:34][CH2:35][C:36]4([CH2:37][CH2:38][CH2:39][CH2:40]4)[CH2:41][CH2:42]3)[cH:43][c... | N#C[O-].NCCCC[C@H](CSc1ccccc1)Nc1ccc(S(=O)(=O)NC(=O)c2ccc(N3CCC4(CCCC4)CC3)cc2)cc1[N+](=O)[O-] | NC(=O)NCCCC[C@H](CSc1ccccc1)Nc1ccc(S(=O)(=O)NC(=O)c2ccc(N3CCC4(CCCC4)CC3)cc2)cc1[N+](=O)[O-] | null | null | CO | Acylation | OtherReaction | f8798d1193af6f9b314ac8855e814716b90ff3758bcfa29778cc632fcaa83b7a | 5efe06db19c806d9e9798893351dc14c0cc48f1e8f8c857f54c6171e86c96a1b | O=C(NS(=O)(=O)c1ccc(NCCSc2ccccc2)cc1)c1ccc(N2CCC3(CCCC3)CC2)cc1 | [C:1]-[C:2]-[NH2;D1;+0:3].[N;H0;D1;+0:4]#[C;H0;D2;+0:5]-[O-;H0;D1:6]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:5](-[NH2;D1;+0:4])=[O;H0;D1;+0:6] | null | [] | null | null | null | null | A solution of Example 287 (60 mg, 0.1 mmol) and potassium cyanate (20 mg, 0.25 mmol) in methanol (1 mL) was stirred at 55° C. for 1.5 hours, cooled to room temperature, treated with water, and extracted with dichloromethane. The combined extracts were washed with saturated sodium bicarbonate, dried (MgSO4), filtered, a... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine | Urea | null | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CCC2(C1)CC[NH]CC2 | null | CO | null | null | N#C[O-].NCCCC[C@H](CSc1ccccc1)Nc1ccc(S(=O)(=O)NC(=O)c2ccc(N3CCC4(CCCC4)CC3)cc2)cc1[N+](=O)[O-]>CO>NC(=O)NCCCC[C@H](CSc1ccccc1)Nc1ccc(S(=O)(=O)NC(=O)c2ccc(N3CCC4(CCCC4)CC3)cc2)cc1[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-244e338b6ba5467ab1f9666d165202d8 | CC(C)(C)OC(=O)/C=C/[C@H](CSc1ccccc1)NC(=O)OC(C)(C)C>>CC(C)(C)OC(=O)N[C@H](CCC(=O)O)CSc1ccccc1 | C(C)(C)(C)OC(=O)N[C@H](/C=C/C(=O)OC(C)(C)C)CSC1=CC=CC=C1>>C(C)(C)(C)OC(=O)N[C@H](CCC(=O)O)CSC1=CC=CC=C1 | CC(C)(C)[O:14][C:12](/[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][S:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)=[O:13]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]([CH2:10][CH2:11][C:12](=[O:13])[OH:14])[CH2:15][S:16][c:17]1[cH:18][cH:19][cH:20][cH:21][... | CC(C)(C)OC(=O)/C=C/[C@H](CSc1ccccc1)NC(=O)OC(C)(C)C | CC(C)(C)OC(=O)N[C@H](CCC(=O)O)CSc1ccccc1 | null | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Cl-].[Rh] | null | Deprotection | OtherReaction | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | c1ccccc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])/[CH;D2;+0:4]=[CH;D2;+0:5]/[C:6](-[C:7])-[#7:8]-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12](-[C;D1;H3:13])(-[C;D1;H3:14])-[C;D1;H3:15]>>[C:7]-[C:6](-[#7:8]-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12](-[C;D1;H3:13])(-[C;D1;H3:14])-[C;D1;H3:15])-[CH2;D2;+0:5]-[CH2;D2;+0:4]-[C:2](=[O;D1;H0:3]... | null | [] | null | null | 24 | HOUR | A mixture of Example 480A (5 g, 13.2 mmol) and Wilkinson's catalyst (1 g) in tolune (125 mL) was stirred under H2at 60° C. for 18 hours, cooled, filtered through silica gel, and concentrated. The concentrate was dissolved in 3:1:1 THF/water/MeOH (150 mL), treated with with a 10-fold excess of LiOH, and stirred for 24 h... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | c1ccccc1 | Other | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Cl-].[Rh] | null | 24 | CC(C)(C)OC(=O)/C=C/[C@H](CSc1ccccc1)NC(=O)OC(C)(C)C>C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Cl-].[Rh]>CC(C)(C)OC(=O)N[C@H](CCC(=O)O)CSc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bd546c45247d43fb9d71ec8beb332979 | COC(=O)c1ccc(-c2ccc(CCO)cc2OC)cc1>>COC(=O)c1ccc(-c2ccc(CC=O)cc2OC)cc1 | OCCC1=CC(=C(C=C1)C1=CC=C(C=C1)C(=O)OC)OC.CC(=O)OI1(C=2C=CC=CC2C(=O)O1)(OC(=O)C)OC(=O)C>>COC1=C(C=CC(=C1)CC=O)C1=CC=C(C=C1)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([CH2:13][CH2:14][OH:15])[cH:16][c:17]2[O:18][CH3:19])[cH:20][cH:21]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([CH2:13][CH:14]=[O:15])[cH:16][c:17]2[O:18][CH3:19])[cH:20][cH:21]1 | COC(=O)c1ccc(-c2ccc(CCO)cc2OC)cc1 | COC(=O)c1ccc(-c2ccc(CC=O)cc2OC)cc1 | null | null | ClCCl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccc(-c2ccccc2)cc1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[c:4]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[C:3]-[c:4] | null | [] | null | null | 90 | MINUTE | A solution of Example 491B (2.47 g, 8.63 mmol) in dichloromethane (25 mL) at room temperature was treated with Dess-Martin periodinane (4.03 g, 9.49 mmol), stirred for 90 minutes, and concentrated The concentrate was purified by flash column chromatography on silica gel with 1:1 ethyl acetate/hexanes to provide the des... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1.c1ccccc1 | null | ClCCl | null | 1.5 | COC(=O)c1ccc(-c2ccc(CCO)cc2OC)cc1>ClCCl>COC(=O)c1ccc(-c2ccc(CC=O)cc2OC)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-463b713c69c341fd8ab16bd434ac5757 | CC(C)(C)OC(=O)N1CCNCC1.COC(=O)c1ccc(-c2ccc(CC=O)cc2OC)cc1>>COC(=O)c1ccc(-c2ccc(CCN3CCN(C(=O)OC(C)(C)C)CC3)cc2OC)cc1 | COC1=C(C=CC(=C1)CC=O)C1=CC=C(C=C1)C(=O)OC.N1(CCNCC1)C(=O)OC(C)(C)C.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>COC1=C(C=CC(=C1)CCN1CCN(CC1)C(=O)OC(C)(C)C)C1=CC=C(C=C1)C(=O)OC | [NH:15]1[CH2:16][CH2:17][N:18]([C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:26][CH2:27]1.O=[CH:14][CH2:13][c:12]1[cH:11][cH:10][c:9](-[c:8]2[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:33][cH:32]2)[c:29]([O:30][CH3:31])[cH:28]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][c... | CC(C)(C)OC(=O)N1CCNCC1.COC(=O)c1ccc(-c2ccc(CC=O)cc2OC)cc1 | COC(=O)c1ccc(-c2ccc(CCN3CCN(C(=O)OC(C)(C)C)CC3)cc2OC)cc1 | null | null | ClCCCl | Heteroatom Alkylation and Arylation | reductive amination | 7a1842565a3c73c1d6bba5dccafef60d48e9eaf6e4a0871f60e828bcbdf26fb1 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(-c2ccc(CCN3CCNCC3)cc2)cc1 | O=[CH;D2;+0:1]-[C:2]-[c:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[c:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | null | [] | null | null | 16 | HOUR | A solution of Example 491C (400 mg, 1.41 mmol) and tert-butyl 1-piperazinecarboxylate (289 mg, 1.55 mmol) in 1,2-dichloroethane (5mL) at room temperature was treated with sodium triacetoxyborohydride (329 mg, 1.55 mmol), and stirred for 16 hours. The solution was purified by flash column chromatography on silica gel wi... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.c1ccccc1.C1C[NH]CC[NH]1 | Other | ClCCCl | null | 16 | CC(C)(C)OC(=O)N1CCNCC1.COC(=O)c1ccc(-c2ccc(CC=O)cc2OC)cc1>ClCCCl>COC(=O)c1ccc(-c2ccc(CCN3CCN(C(=O)OC(C)(C)C)CC3)cc2OC)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6e76420ede2d46449fa7caf17eec7309 | CC(C)(C)OC(=O)c1ccc(F)cc1.OC1(c2ccccc2)CCNCC1>>CC(C)(C)OC(=O)c1ccc(N2CCC(O)(c3ccccc3)CC2)cc1 | OC1(CCNCC1)C1=CC=CC=C1.C(C)(C)(C)OC(C1=CC=C(C=C1)F)=O.C([O-])([O-])=O.[K+].[K+]>>OC1(CCN(CC1)C1=CC=C(C(=O)OC(C)(C)C)C=C1)C1=CC=CC=C1 | F[c:11]1[cH:10][cH:9][c:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[cH:26][cH:25]1.[NH:12]1[CH2:13][CH2:14][C:15]([OH:16])([c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[CH2:23][CH2:24]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([N:12]2[CH2:13][CH2:14][C:15]([OH:16])([c:17]3[cH:1... | CC(C)(C)OC(=O)c1ccc(F)cc1.OC1(c2ccccc2)CCNCC1 | CC(C)(C)OC(=O)c1ccc(N2CCC(O)(c3ccccc3)CC2)cc1 | null | null | CS(=O)C.C(C)OCC | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | ad5ec9c4592e4dee5877fc4f1309a503a378773e18ebc21adf780b709f6e28c5 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(C2CCN(c3ccccc3)CC2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:9]-[C:10] | null | [] | 125 | CELSIUS | 16 | HOUR | A solution of 4-hydroxy-4-phenyl piperidine (221 mg, 1.25 mmol) in DMSO (1 mL) was treated with tert-butyl-4-fluorobenzoate (196 mg, 1.00 mmol) and powdered potassium carbonate (173 mg, 1.25 mmol), stirred vigorously at 125° C. for 16 hours, cooled to room temperature, diluted with diethyl ether, washed with brine, dri... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.C1CCNCC1 | c1ccccc1.C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1 | HF | CS(=O)C.C(C)OCC | 125 | 16 | CC(C)(C)OC(=O)c1ccc(F)cc1.OC1(c2ccccc2)CCNCC1>CS(=O)C.C(C)OCC>CC(C)(C)OC(=O)c1ccc(N2CCC(O)(c3ccccc3)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9d85b669c2214a29b20c5d1fbbd89044 | CC(C)(C)OC(=O)c1ccc(N2CCC(O)(c3ccccc3)CC2)cc1>>O=C(O)c1ccc(N2CCC(O)(c3ccccc3)CC2)cc1 | OC1(CCN(CC1)C1=CC=C(C(=O)OC(C)(C)C)C=C1)C1=CC=CC=C1>>OC1(CCN(CC1)C1=CC=C(C(=O)O)C=C1)C1=CC=CC=C1 | CC(C)(C)[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]([N:8]2[CH2:9][CH2:10][C:11]([OH:12])([c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[CH2:19][CH2:20]2)[cH:21][cH:22]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([N:8]2[CH2:9][CH2:10][C:11]([OH:12])([c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[CH2:19][CH2:20]2)[cH:21][cH:2... | CC(C)(C)OC(=O)c1ccc(N2CCC(O)(c3ccccc3)CC2)cc1 | O=C(O)c1ccc(N2CCC(O)(c3ccccc3)CC2)cc1 | null | null | C(=O)(C(F)(F)F)O | Deprotection | Deprotection of carboxylic acid | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | c1ccc(C2CCN(c3ccccc3)CC2)cc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | null | null | A solution of Example 493A (0.32 g, 0.91 mmol) in TFA (2 mL) at room temperature was stirred for 1 hour, and concentrated. The concentrate was azeotropically distilled with toluene three times and dried to provide the desired product. MS (ESI(+)) m/e 298 (M+H)+.
Conditions: See reaction.notes.procedure_details.
Workup:... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1 | Other | C(=O)(C(F)(F)F)O | null | null | CC(C)(C)OC(=O)c1ccc(N2CCC(O)(c3ccccc3)CC2)cc1>C(=O)(C(F)(F)F)O>O=C(O)c1ccc(N2CCC(O)(c3ccccc3)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6fc64735f1c047d6841d9d765cf70abe | CC(C)(C)OC(=O)N1CCC(=O)CC1>>CC1(O)CCN(C(=O)OC(C)(C)C)CC1 | C[Mg]Br.O=C1CCN(CC1)C(=O)OC(C)(C)C.[NH4+].[Cl-]>>OC1(CCN(CC1)C(=O)OC(C)(C)C)C | [C:2]1(=[O:3])[CH2:4][CH2:5][N:6]([C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[CH2:14][CH2:15]1>>[CH3:1][C:2]1([OH:3])[CH2:4][CH2:5][N:6]([C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[CH2:14][CH2:15]1 | CC(C)(C)OC(=O)N1CCC(=O)CC1 | CC1(O)CCN(C(=O)OC(C)(C)C)CC1 | null | null | C(C)OCC | Miscellaneous | OtherReaction | dfefed99c59b497159616052101f24c8ee451a3c3938a028396dd346c800e3a6 | 8811b4d793f7cfa9f0f1f47a008648edabb54f371f76dfa680dd5b2e1564c6c5 | C1CCNCC1 | [O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:3]-[C:4]-[#7:5]-[C:6]-[C:7]-1>>[C;D1;H3:8]-[C;H0;D4;+0:2]1(-[OH;D1;+0:1])-[C:3]-[C:4]-[#7:5]-[C:6]-[C:7]-1 | null | [] | null | null | 18 | HOUR | A solution of 3M methyl magnesium bromide in diethyl ether (2.0 mL) in diethyl ether (3 mL) at 0° C. was treated with a solution of tert-butyl 4-oxo-1-piperidinecarboxylate (1.0 g, 5.00 mmol) in diethyl ether (5 mL), warmed to room temperature, stirred for 18 hours, treated with saturated NH4Cl, and extracted with diet... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol | C1CC[NH]CC1 | C1CC[NH]CC1 | C1CC[NH]CC1 | Other | C(C)OCC | null | 18 | CC(C)(C)OC(=O)N1CCC(=O)CC1>C(C)OCC>CC1(O)CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-72f9d7eccb6240f287d432ceb20a86d6 | COc1cc(CCN2CCN(C(=O)OC(C)(C)C)CC2)ccc1-c1ccc(C(=O)NS(=O)(=O)c2ccc(N[C@H](CCN(C)C)CSc3ccccc3)c([N+](=O)[O-])c2)cc1>>COc1cc(CCN2CCNCC2)ccc1-c1ccc(C(=O)NS(=O)(=O)c2ccc(N[C@H](CCN(C)C)CSc3ccccc3)c([N+](=O)[O-])c2)cc1 | CN(CC[C@H](CSC1=CC=CC=C1)NC1=C(C=C(C=C1)S(=O)(=O)NC(=O)C1=CC=C(C=C1)C1=C(C=C(C=C1)CCN1CCN(CC1)C(=O)OC(C)(C)C)OC)[N+](=O)[O-])C>>CN(CC[C@H](CSC1=CC=CC=C1)NC1=C(C=C(C=C1)S(=O)(=O)NC(=O)C1=CC=C(C=C1)C1=C(C=C(C=C1)CCN1CCNCC1)OC)[N+](=O)[O-])C | CC(C)(C)OC(=O)[N:11]1[CH2:10][CH2:9][N:8]([CH2:7][CH2:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[c:16](-[c:17]3[cH:18][cH:19][c:20]([C:21](=[O:22])[NH:23][S:24](=[O:25])(=[O:26])[c:27]4[cH:28][cH:29][c:30]([NH:31][C@H:32]([CH2:33][CH2:34][N:35]([CH3:36])[CH3:37])[CH2:38][S:39][c:40]5[cH:41][cH:42][cH:43][cH:44][cH:45]5)[c:46]([... | COc1cc(CCN2CCN(C(=O)OC(C)(C)C)CC2)ccc1-c1ccc(C(=O)NS(=O)(=O)c2ccc(N[C@H](CCN(C)C)CSc3ccccc3)c([N+](=O)[O-])c2)cc1 | COc1cc(CCN2CCNCC2)ccc1-c1ccc(C(=O)NS(=O)(=O)c2ccc(N[C@H](CCN(C)C)CSc3ccccc3)c([N+](=O)[O-])c2)cc1 | null | null | O1CCOCC1.Cl | Reduction | Boc amine deprotection | 2c25e19aee181a3c5131cfdfda27035fd54d4379a11d745dfb75d386bacfd500 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=C(NS(=O)(=O)c1ccc(NCCSc2ccccc2)cc1)c1ccc(-c2ccc(CCN3CCNCC3)cc2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1>>[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:1]-[C:2]-[C:3]-1 | null | [] | null | null | null | null | A solution of Example 491F (284 mg, 0.34 mmol) in 1,4-dioxane (1.5 mL) and 4M HCl (1.5 mL) at room temperature was stirred for 16 hours. The solution was purified by flash column chromatography on silica gel with 80:20:0.5 dichloromethane/methanol/concentrated ammonium hydroxide to provide the desired product. MS (ESI)... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | c1ccccc1.C1C[NH]CCN1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | O1CCOCC1.Cl | null | null | COc1cc(CCN2CCN(C(=O)OC(C)(C)C)CC2)ccc1-c1ccc(C(=O)NS(=O)(=O)c2ccc(N[C@H](CCN(C)C)CSc3ccccc3)c([N+](=O)[O-])c2)cc1>O1CCOCC1.Cl>COc1cc(CCN2CCNCC2)ccc1-c1ccc(C(=O)NS(=O)(=O)c2ccc(N[C@H](CCN(C)C)CSc3ccccc3)c([N+](=O)[O-])c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d68fb9f122fd402c93a8c8a38a6587a0 | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.O=C1CNCCN1>>CC(C)(C)OC(=O)N1CCNC(=O)C1 | N1C(CNCC1)=O.O(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C>>O=C1CN(CCN1)C(=O)OC(C)(C)C | CC(C)(C)OC(=O)O[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[NH:8]1[CH2:9][CH2:10][NH:11][C:12](=[O:13])[CH2:14]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][C:12](=[O:13])[CH2:14]1 | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.O=C1CNCCN1 | CC(C)(C)OC(=O)N1CCNC(=O)C1 | null | null | C(C)#N | Protection | Boc amine protection with Boc anhydride | 6b6bceeda760b13c0e0d3785668f44a028e616c30bc5b09d93a2450415ad5022 | 7c9d9ba915c29b1020a278f50f3c8f9cc1fd09ebab5bff22f0c1b047d4ae169a | O=C1CNCCN1 | C-C(-C)(-C)-O-C(=O)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[O;D1;H0:8]=[C:9]1-[#7:10]-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-1>>[C;D1;H3:5]-[C:4](-[C;D1;H3:6])(-[C;D1;H3:7])-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:13]1-[C:14]-[C:9](=[O;D1;H0:8])-[#7:10]-[C:11]-[C:12]-1 | null | [] | null | null | 3 | HOUR | A solution of Example 500A (500 mg, 4.99 mmol) in acetonitrile (25 mL) at room temperature was treated with BOC2O (1198 mg, 5.49 mmol), stirred for 3 hours, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 95:5 ethyl acetate/methanol to provide the desired product.
Condit... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Carbonic Ester.Carbonic Ester.Secondary amine.Boc.Boc | Carbamic ester | C1CNCCN1 | C1C[NH]CCN1 | C1C[NH]CCN1 | HO- | C(C)#N | null | 3 | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.O=C1CNCCN1>C(C)#N>CC(C)(C)OC(=O)N1CCNC(=O)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-39c52997c4d64128b0ec907743324cfd | C=CCOC1(CC=C)CCN(C(=O)OC(C)(C)C)CC1>>CC(C)(C)OC(=O)N1CCC2(CC=CCO2)CC1 | C(C=C)C1(CCN(CC1)C(=O)OC(C)(C)C)OCC=C>>O1CC=CCC12CCN(CC2)C(=O)OC(C)(C)C | C=[CH:13][CH2:12][C:11]1([O:16][CH2:15][CH:14]=C)[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:18][CH2:17]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11]2([CH2:12][CH:13]=[CH:14][CH2:15][O:16]2)[CH2:17][CH2:18]1 | C=CCOC1(CC=C)CCN(C(=O)OC(C)(C)C)CC1 | CC(C)(C)OC(=O)N1CCC2(CC=CCO2)CC1 | null | null | C1=CC=CC=C1 | C-C Coupling | OtherReaction | ce2b403338073b1a94caab8e44a26ee04764997d0593da03d3176d1f623e82cf | 67a23c4de67c22dcd6bc1d4c033efdcf679af248440c3b10e6768679c5f73280 | C1=CCC2(CCNCC2)OC1 | C=[CH;D2;+0:1]-[C:2]-[C:3]-[#8:4]-[C:5]-[CH;D2;+0:6]=C>>[#8:4]1-[C:3]-[C:2]-[CH;D2;+0:1]=[CH;D2;+0:6]-[C:5]-1 | null | [] | null | null | 18 | HOUR | A solution of Example 518B (0.79 g, 2.81 mmol) in degassed benzene (100 mL) at room temperature was treated with bis-tricyclohexylphosphine benzylidene ruthenium (IV) dichloride (150 mg), stirred for 18 hours, and concentrated The concentrate was purified by flash column chromatography on silica gel with 10%-25% ethyl ... | 10.6084/m9.figshare.5104873.v1 | null | Allyl.Allyl | null | null | C1=CCC2(CC[NH]CC2)OC1 | C1=CCC2(CC[NH]CC2)OC1 | Other | C1=CC=CC=C1 | null | 18 | C=CCOC1(CC=C)CCN(C(=O)OC(C)(C)C)CC1>C1=CC=CC=C1>CC(C)(C)OC(=O)N1CCC2(CC=CCO2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ce224a7eabf04ad5997f3efe1cb72212 | CCOC(=O)C1CCN(C(=O)OC(C)(C)C)CC1.CI>>CCOC(=O)C1(C)CCN(C(=O)OC(C)(C)C)CC1 | CI.N1(CCC(CC1)C(=O)OCC)C(=O)OC(C)(C)C.[Li+].CC(C)[N-]C(C)C.C1CCCCC1>>CC1(CCN(CC1)C(=O)OC(C)(C)C)C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][CH2:19]1.I[CH3:7]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1([CH3:7])[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][CH2:19]1 | CCOC(=O)C1CCN(C(=O)OC(C)(C)C)CC1.CI | CCOC(=O)C1(C)CCN(C(=O)OC(C)(C)C)CC1 | null | null | C1CCOC1 | C-C Coupling | Methylation with MeI_tertiary | 6bdbd896659a1d85611ac4aba77b405f65bed934821cffd10e318213ab724706 | 49d6f28766066d07dffbcc6f4da77792f6ba67b4de619800bad651525d6fe2e7 | C1CCNCC1 | I-[CH3;D1;+0:1].[C:2]-[#8:3]-[C:4](=[O;D1;H0:5])-[CH;D3;+0:6]1-[C:7]-[C:8]-[#7:9]-[C:10]-[C:11]-1>>[C:2]-[#8:3]-[C:4](=[O;D1;H0:5])-[C;H0;D4;+0:6]1(-[CH3;D1;+0:1])-[C:7]-[C:8]-[#7:9]-[C:10]-[C:11]-1 | null | [] | null | null | 30 | MINUTE | A solution of Example 532A (2.1 g, 8.1 mmol) in THF (81 mL) at −78° C. was treated dropwise with 1.5M LDA in cyclohexane (6.0 mL, 8.9 mmol), stirred for 30 minutes, treated dropwise with methyl iodide (0.76 mL, 12.1 mmol), stirred for 2.5 hours, quenched with saturated NH4Cl, and extracted with diethyl ether. The combi... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | C1CC[NH]CC1 | C1CC[NH]CC1 | C1CC[NH]CC1 | HI | C1CCOC1 | null | 0.5 | CCOC(=O)C1CCN(C(=O)OC(C)(C)C)CC1.CI>C1CCOC1>CCOC(=O)C1(C)CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c9a185424ee24b58b45040fed79c6a82 | CCOC(=O)C1(C)CCN(C(=O)OC(C)(C)C)CC1>>CCOC(=O)C1(C)CCNCC1 | CC1(CCN(CC1)C(=O)OC(C)(C)C)C(=O)OCC>>CC1(CCNCC1)C(=O)OCC | CC(C)(C)OC(=O)[N:10]1[CH2:9][CH2:8][C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])([CH3:7])[CH2:12][CH2:11]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1([CH3:7])[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]1 | CCOC(=O)C1(C)CCN(C(=O)OC(C)(C)C)CC1 | CCOC(=O)C1(C)CCNCC1 | null | null | Cl.O1CCOCC1 | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | C1CCNCC1 | C-C(-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] | null | [] | null | null | null | null | A solution of Example 532B (2.1 g, 8.0 mmol) in 4M HCl in dioxane (10 mL) at room temperature was stirred for 3 hours and concentrated to provide the desired product. MS (DCI) mne 171 (M+H)+.
Conditions: See reaction.notes.procedure_details.
Workup: concentrated | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | C1CCNCC1 | HO- | Cl.O1CCOCC1 | null | null | CCOC(=O)C1(C)CCN(C(=O)OC(C)(C)C)CC1>Cl.O1CCOCC1>CCOC(=O)C1(C)CCNCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-13c4913959d247738f507fd2a658886d | BrCc1ccccc1.O=C(O)c1ccc(F)cc1>>O=C(OCc1ccccc1)c1ccc(F)cc1 | FC1=CC=C(C(=O)O)C=C1.C(C1=CC=CC=C1)Br.C([O-])([O-])=O.[Cs+].[Cs+]>>FC1=CC=C(C(=O)OCC2=CC=CC=C2)C=C1 | Br[CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1.[O:1]=[C:2]([OH:3])[c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]1>>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]1 | BrCc1ccccc1.O=C(O)c1ccc(F)cc1 | O=C(OCc1ccccc1)c1ccc(F)cc1 | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 06c4f868ad4646eea8208ecb83f54ca035dd62d04f0d8101641a4f487f2c695c | 8446834f0edd1e71a2dcaffc09b80c7367abf3407263a8998354a2d20c1766bb | O=C(OCc1ccccc1)c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6](-[OH;D1;+0:7])-[c:8]>>[O;D1;H0:5]=[C:6](-[c:8])-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 24 | HOUR | A mixture of 4-fluorobenzoic acid (4.9 g, 35.3 mmol), benzyl bromide (3.8 mL, 31.7 mmol), and cesium carbonate (17.2 g, 53 mmol) in DMF (50 mL,) at room temperature was stirred for 24 hours, diluted with water, and extracted with diethyl ether. The combined extracts were washed with brine, dried (MgSO4), filtered, and ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Ester | null | null | c1ccccc1.c1ccccc1 | HBr | O.CN(C)C=O | null | 24 | BrCc1ccccc1.O=C(O)c1ccc(F)cc1>O.CN(C)C=O>O=C(OCc1ccccc1)c1ccc(F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5ac43e5e93c54008ba4c942b6b3598b4 | CC1(C(=O)O)CCN(c2ccc(C(=O)NS(=O)(=O)c3ccc(NCCSc4ccccc4)c([N+](=O)[O-])c3)cc2)CC1>>CC1(CO)CCN(c2ccc(C(=O)NS(=O)(=O)c3ccc(NCCSc4ccccc4)c([N+](=O)[O-])c3)cc2)CC1 | [BH4-].[Na+].CC1(CCN(CC1)C1=CC=C(C=C1)C(=O)NS(=O)(=O)C1=CC(=C(C=C1)NCCSC1=CC=CC=C1)[N+](=O)[O-])C(=O)O.CN1CCOCC1.ClC(=O)OCC(C)C>>OCC1(CCN(CC1)C1=CC=C(C(=O)NS(=O)(=O)C2=CC(=C(C=C2)NCCSC2=CC=CC=C2)[N+](=O)[O-])C=C1)C | O=[C:3]([C:2]1([CH3:1])[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][c:11]([C:12](=[O:13])[NH:14][S:15](=[O:16])(=[O:17])[c:18]3[cH:19][cH:20][c:21]([NH:22][CH2:23][CH2:24][S:25][c:26]4[cH:27][cH:28][cH:29][cH:30][cH:31]4)[c:32]([N+:33](=[O:34])[O-:35])[cH:36]3)[cH:37][cH:38]2)[CH2:39][CH2:40]1)[OH:4]>>[CH3:1][C:2]1([CH2:3][... | CC1(C(=O)O)CCN(c2ccc(C(=O)NS(=O)(=O)c3ccc(NCCSc4ccccc4)c([N+](=O)[O-])c3)cc2)CC1 | CC1(CO)CCN(c2ccc(C(=O)NS(=O)(=O)c3ccc(NCCSc4ccccc4)c([N+](=O)[O-])c3)cc2)CC1 | null | null | O.COCCOC | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | O=C(NS(=O)(=O)c1ccc(NCCSc2ccccc2)cc1)c1ccc(N2CCCCC2)cc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[C:3](-[C;D1;H3:4])(-[C:5])-[C:6]>>[C:5]-[C:3](-[C;D1;H3:4])(-[CH2;D2;+0:1]-[O;D1;H1:2])-[C:6] | null | [] | -15 | CELSIUS | 15 | MINUTE | A solution of Example 532H (35 mg, 0.06 mmol), 4-methylmorpholine (0.007 mL, 0.06 mmol), and DME (0.3 mL) at −15° C. was treated dropwise with isobutyl chloroformate (0.008 mL, 0.06 mmol), stirred for 15 minutes, and filtered. The filter cake was washed with DME and the filtrate and washings were combined. The solution... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | C1CC[NH]CC1.c1ccccc1.c1ccccc1.c1ccccc1 | Other | O.COCCOC | -15 | 0.25 | CC1(C(=O)O)CCN(c2ccc(C(=O)NS(=O)(=O)c3ccc(NCCSc4ccccc4)c([N+](=O)[O-])c3)cc2)CC1>O.COCCOC>CC1(CO)CCN(c2ccc(C(=O)NS(=O)(=O)c3ccc(NCCSc4ccccc4)c([N+](=O)[O-])c3)cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f6782bcb88384b5ca2b69805ae1eddde | NCCCC[C@H](CSc1ccccc1)Nc1ccc(S(=O)(=O)NC(=O)c2ccc(N3CCC4(CCCC4)CC3)cc2)cc1[N+](=O)[O-]>>N=C(N)NCCCC[C@H](CSc1ccccc1)Nc1ccc(S(=O)(=O)NC(=O)c2ccc(N3CCC4(CCCC4)CC3)cc2)cc1[N+](=O)[O-] | NCCCC[C@H](CSC1=CC=CC=C1)NC1=C(C=C(C=C1)S(=O)(=O)NC(C1=CC=C(C=C1)N1CCC2(CCCC2)CC1)=O)[N+](=O)[O-].C(C)(C)N(CC)C(C)C.CN(C)C=O>>NC(=N)NCCCC[C@H](CSC1=CC=CC=C1)NC1=C(C=C(C=C1)S(=O)(=O)NC(C1=CC=C(C=C1)N1CCC2(CCCC2)CC1)=O)[N+](=O)[O-] | [NH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C@H:9]([CH2:10][S:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[NH:18][c:19]1[cH:20][cH:21][c:22]([S:23](=[O:24])(=[O:25])[NH:26][C:27](=[O:28])[c:29]2[cH:30][cH:31][c:32]([N:33]3[CH2:34][CH2:35][C:36]4([CH2:37][CH2:38][CH2:39][CH2:40]4)[CH2:41][CH2:42]3)[cH:43][cH:44]2)[cH:45][c:4... | NCCCC[C@H](CSc1ccccc1)Nc1ccc(S(=O)(=O)NC(=O)c2ccc(N3CCC4(CCCC4)CC3)cc2)cc1[N+](=O)[O-] | N=C(N)NCCCC[C@H](CSc1ccccc1)Nc1ccc(S(=O)(=O)NC(=O)c2ccc(N3CCC4(CCCC4)CC3)cc2)cc1[N+](=O)[O-] | null | null | null | Functional Group Addition | OtherReaction | 4fbd61810687f265a1928bdad0d611b8a3b0a276707821eb7e74c90a9b8fe484 | c15d00b2143ff6be17711701b3a1268fe1c3598f83b20a6cd29a72406090607e | O=C(NS(=O)(=O)c1ccc(NCCSc2ccccc2)cc1)c1ccc(N2CCC3(CCCC3)CC2)cc1 | [C:1]-[C:2]-[NH2;D1;+0:3]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C:4](=[N;D1;H1:5])-[N;D1;H2:6] | null | [] | null | null | null | null | A solution of Example 287 (30 mg, 0.05 mmol), aminoiminosulfonic acid (7 mg, 0.055 mmol), diisopropylethylamine (0.02 M1), and DMF (0.3 mL) at room temperature was stirred for 24 hours and concentrated. The concentrate was purified by reverse phase chromatography with 0-90% methanol/0.1% aqueous TFA to provide the desi... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Primary amine.Secondary amine | null | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CCC2(C1)CC[NH]CC2 | Other | null | null | null | NCCCC[C@H](CSc1ccccc1)Nc1ccc(S(=O)(=O)NC(=O)c2ccc(N3CCC4(CCCC4)CC3)cc2)cc1[N+](=O)[O-]>>N=C(N)NCCCC[C@H](CSc1ccccc1)Nc1ccc(S(=O)(=O)NC(=O)c2ccc(N3CCC4(CCCC4)CC3)cc2)cc1[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a3e814fd460140f39cfae15c1ddd4afb | CCC(CC)(CO)CO.COC(=O)c1c(O)c(O)c(C(=O)OC)n1Cc1ccccc1>>CCC1(CC)COc2c(c(C(=O)OC)n(Cc3ccccc3)c2C(=O)OC)OC1 | C(C)C(CO)(CO)CC.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.N(=NC(=O)OCC)C(=O)OCC.COC(=O)C=1N(C(=C(C1O)O)C(=O)OC)CC1=CC=CC=C1.N1C=CC=C1>>COC(=O)C=1N(C(=C2OCC(COC12)(CC)CC)C(=O)OC)CC1=CC=CC=C1 | O[CH2:6][C:3]([CH2:2][CH3:1])([CH2:4][CH3:5])[CH2:29]O.[OH:7][c:8]1[c:9]([OH:28])[c:10]([C:11](=[O:12])[O:13][CH3:14])[n:15]([CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[c:23]1[C:24](=[O:25])[O:26][CH3:27]>>[CH3:1][CH2:2][C:3]1([CH2:4][CH3:5])[CH2:6][O:7][c:8]2[c:9]([c:10]([C:11](=[O:12])[O:13][CH3:14])[n:15]([... | CCC(CC)(CO)CO.COC(=O)c1c(O)c(O)c(C(=O)OC)n1Cc1ccccc1 | CCC1(CC)COc2c(c(C(=O)OC)n(Cc3ccccc3)c2C(=O)OC)OC1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 1215c3f6aac7ca34fe457aa8add81c0a0f0dc07e98a78a57957222af48a54bc4 | cd35ce5731247dee33d5ad312c41487245b509adde46d8f559cf867afeb9eba2 | c1ccc(Cn2cc3c(c2)OCCCO3)cc1 | O-[CH2;D2;+0:1]-[C:2](-[C:3])(-[C:4])-[CH2;D2;+0:5]-O.[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[#7;a:10](-[C:11]):[c:12](-[C:13](-[#8:14])=[O;D1;H0:15]):[c:16](-[OH;D1;+0:17]):[c:18]:1-[OH;D1;+0:19]>>[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[#7;a:10](-[C:11]):[c:12](-[C:13](-[#8:14])=[O;D1;H0:15]):[c:16]2:[c:18]:1-[O;H0;D2;+0:19]-[C... | null | [] | null | null | null | null | In the present method, 1-Benzyl-3,4-dihydroxy-1H-pyrrole-2,5-dicarboxylic acid dimethyl ester, the pyrrole derivative labeled A4 in FIG. 4 (hereinafter referred to as compound A4) is first synthesized from commercially available chemicals according to prior art techniques (see A. Merz, R. Schropp, E. Dotterl, “3,4-Dial... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Primary alcohol.Aromatic alcohol.Aromatic alcohol | Ether.Ether | null | C1COc2c[nH]cc2OC1 | C1COc2c[nH]cc2OC1.c1ccccc1 | HO- | O1CCCC1 | null | null | CCC(CC)(CO)CO.COC(=O)c1c(O)c(O)c(C(=O)OC)n1Cc1ccccc1>O1CCCC1>CCC1(CC)COc2c(c(C(=O)OC)n(Cc3ccccc3)c2C(=O)OC)OC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4fcabc0faaaa4506ae4a26616316fe02 | COC(=O)c1sc(C(=O)OC)c(O)c1O.C[Si]1(C)COc2cscc2OC1>>COC(=O)c1sc(C(=O)OC)c2c1OC[Si](C)(C)CO2 | C[Si]1(COC2=CSC=C2OC1)C.COC(=O)C=1SC(=C(C1O)O)C(=O)OC.S1C=CC=C1.OC(O)[SiH](C)C.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.CCOC(=O)/N=N/C(=O)OCC>>COC(=O)C=1SC(=C2OC[Si](COC12)(C)C)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[s:6][c:7]([C:8](=[O:9])[O:10][CH3:11])[c:12]([OH:20])[c:13]1[OH:14].c1scc2c1O[CH2:15][Si:16]([CH3:17])([CH3:18])[CH2:19]O2>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[s:6][c:7]([C:8](=[O:9])[O:10][CH3:11])[c:12]2[c:13]1[O:14][CH2:15][Si:16]([CH3:17])([CH3:18])[CH2:19][O:20]2 | COC(=O)c1sc(C(=O)OC)c(O)c1O.C[Si]1(C)COc2cscc2OC1 | COC(=O)c1sc(C(=O)OC)c2c1OC[Si](C)(C)CO2 | null | null | O.C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 7b6137ae600039f3bd8723aafc5c687f499e1388e832f227c897cac93b63c5f3 | e37a086490c02521b04b2676ff92ea843071e75d56b8b4bb1a6a949554462337 | c1scc2c1OC[SiH2]CO2 | [#8:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[#16;a:5]:[c:6](-[C:7](-[#8:8])=[O;D1;H0:9]):[c:10](-[OH;D1;+0:11]):[c:12]:1-[OH;D1;+0:13].[C;D1;H3:14]-[#14:15]1(-[C;D1;H3:16])-[CH2;D2;+0:17]-O-c2:c:s:c:c:2-O-[CH2;D2;+0:18]-1>>[#8:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[#16;a:5]:[c:6](-[C:7](-[#8:8])=[O;D1;H0:9]):[c:10]2:[c:12]:1-[O;H0;D2;+0... | null | [] | null | null | null | null | A synthesis for 6,6-dimethyl-6,7-dihydro-5H-4,8-dioxa-2-thia-6-sila-azulene, a silicon-containing EC monomer generally related to 3,4-alkylenedioxythiophene, is shown in FIG. 7. First, 3,4-Dihydroxy-thiophene-2,5-dicarboxylic acid dimethyl ester, the thiophene derivative labeled A7 in FIG. 7 (hereinafter referred to as... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Aromatic alcohol.Aromatic alcohol | Ether.Ether | c1scc2c1OC[Si]CO2 | c1scc2c1OC[Si]CO2 | c1scc2c1OC[Si]CO2 | Other | O.C1CCOC1 | null | null | COC(=O)c1sc(C(=O)OC)c(O)c1O.C[Si]1(C)COc2cscc2OC1>O.C1CCOC1>COC(=O)c1sc(C(=O)OC)c2c1OC[Si](C)(C)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a3fb00f4f2f34bf4924744098467e41c | CC(=O)N1c2ccccc2[C@H](Nc2ccccc2)C[C@@H]1C.O=C(Cl)c1ccco1>>CC(=O)N1c2ccccc2[C@H](N(C(=O)c2ccco2)c2ccccc2)C[C@@H]1C | C[C@@H]1N(C2=CC=CC=C2[C@@H](C1)NC1=CC=CC=C1)C(C)=O.O1C(=CC=C1)C(=O)Cl.N1=CC=CC=C1>>C(C)(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C(=O)C=1OC=CC1)C1=CC=CC=C1)C | [CH3:1][C:2](=[O:3])[N:4]1[c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[C@H:11]([NH:12][c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[CH2:26][C@@H:27]1[CH3:28].Cl[C:13](=[O:14])[c:15]1[cH:16][cH:17][cH:18][o:19]1>>[CH3:1][C:2](=[O:3])[N:4]1[c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[C@H:11]([N:12]([C:13](=[O:14])[c:15]2[cH:16][cH:17][... | CC(=O)N1c2ccccc2[C@H](Nc2ccccc2)C[C@@H]1C.O=C(Cl)c1ccco1 | CC(=O)N1c2ccccc2[C@H](N(C(=O)c2ccco2)c2ccccc2)C[C@@H]1C | null | null | C1(=CC=CC=C1)C | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccco1)N(c1ccccc1)[C@@H]1CCNc2ccccc21 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6].[C:7]-[C:8](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12])-[c:13]>>[C:7]-[C:8](-[N;H0;D3;+0:9](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6])-[c:10](:[c:11]):[c:12])-[c:13] | 40 | [{"value": 40.0, "product": "C(C)(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C(=O)C=1OC=CC1)C1=CC=CC=C1)C", "details": "PERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | A round bottom flask under nitrogen atmosphere was charged with cis-(2-methyl-4-phenylamino-3,4-dihydro-2H-quinolin-1-yl)-ethanone (0.163 g, 0.58 mmol, 1.0 equiv) and 2-furoyl chloride (0.285 mL, 2.9 mmol, 5.0 equ), pyridine (1.0 equiv.) and dry toluene (3 mL). The solution was heated to 90° C. for 15 h. The reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccc2c(c1)CCC[NH]2.c1ccoc1.c1ccccc1 | HCl | C1(=CC=CC=C1)C | 90 | null | CC(=O)N1c2ccccc2[C@H](Nc2ccccc2)C[C@@H]1C.O=C(Cl)c1ccco1>C1(=CC=CC=C1)C>CC(=O)N1c2ccccc2[C@H](N(C(=O)c2ccco2)c2ccccc2)C[C@@H]1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7f925bc2320b4136acc246d65c313632 | CC(=O)N1c2ccccc2[C@@H](Nc2ccccc2)C[C@@H]1C.O=C(Cl)c1ccco1>>CC(=O)N1c2ccccc2[C@@H](N(C(=O)c2ccco2)c2ccccc2)C[C@@H]1C | C[C@@H]1N(C2=CC=CC=C2[C@H](C1)NC1=CC=CC=C1)C(C)=O.O1C(=CC=C1)C(=O)Cl.N1=CC=CC=C1>>C(C)(=O)N1[C@H](C[C@@H](C2=CC=CC=C12)N(C(=O)C=1OC=CC1)C1=CC=CC=C1)C | [CH3:1][C:2](=[O:3])[N:4]1[c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[C@@H:11]([NH:12][c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[CH2:26][C@@H:27]1[CH3:28].Cl[C:13](=[O:14])[c:15]1[cH:16][cH:17][cH:18][o:19]1>>[CH3:1][C:2](=[O:3])[N:4]1[c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[C@@H:11]([N:12]([C:13](=[O:14])[c:15]2[cH:16][cH:17... | CC(=O)N1c2ccccc2[C@@H](Nc2ccccc2)C[C@@H]1C.O=C(Cl)c1ccco1 | CC(=O)N1c2ccccc2[C@@H](N(C(=O)c2ccco2)c2ccccc2)C[C@@H]1C | null | null | C1(=CC=CC=C1)C | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccco1)N(c1ccccc1)[C@H]1CCNc2ccccc21 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6].[C:7]-[C:8](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12])-[c:13]>>[C:7]-[C:8](-[N;H0;D3;+0:9](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6])-[c:10](:[c:11]):[c:12])-[c:13] | 34 | [{"value": 34.0, "product": "C(C)(=O)N1[C@H](C[C@@H](C2=CC=CC=C12)N(C(=O)C=1OC=CC1)C1=CC=CC=C1)C", "details": "PERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | A round bottom flask under nitrogen atmosphere was charged with (±)-trans-1-(2-methyl-4-phenylamino-3,4-dihydro-2H-quinolin-1-yl)-ethanone (0.110 g, 0.39 mmol, 1.0 equiv) and 2-furoyl chloride (0.193 mL, 1.9 mmol, 5.0 equ), pyridine (1.0 equ.) and dry toluene (5 mL). The solution was heated to 50° C. for 5 h. The react... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccc2c(c1)CCC[NH]2.c1ccoc1.c1ccccc1 | HCl | C1(=CC=CC=C1)C | 50 | null | CC(=O)N1c2ccccc2[C@@H](Nc2ccccc2)C[C@@H]1C.O=C(Cl)c1ccco1>C1(=CC=CC=C1)C>CC(=O)N1c2ccccc2[C@@H](N(C(=O)c2ccco2)c2ccccc2)C[C@@H]1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8ce7c8db5ccf4775a9f4dd546229a7a7 | CCN(C(C)C)C(C)C.C[C@H]1C[C@@H](Nc2ccccc2)c2ccccc2N1.O.O=C(Cl)c1ccco1>>CC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccco2)c2ccccc21 | O.O1C(=CC=C1)C(=O)Cl.C[C@@H]1NC2=CC=CC=C2[C@@H](C1)NC1=CC=CC=C1.C(C)(C)N(CC)C(C)C>>O1C(=CC=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C(C)=O)C1=CC=CC=C1)C | CC(C)N(C(C)C)[CH2:2][CH3:1].[NH:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[C@@H:11]1[CH2:12][C@H:13]([CH3:14])[NH:15][c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]21.[OH2:3].Cl[C:16](=[O:17])[c:18]1[cH:19][cH:20][cH:21][o:22]1>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[C@@H:11]1[CH2:12][C@H:13]([CH3:... | CCN(C(C)C)C(C)C.C[C@H]1C[C@@H](Nc2ccccc2)c2ccccc2N1.O.O=C(Cl)c1ccco1 | CC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccco2)c2ccccc21 | null | null | ClCCl | Acylation | OtherReaction | d8fe791f0ca395497d722fb06b6ec821702194f4b653cb7bc63fa1b8371151dd | b1100398e30c6073eb2aa2e07cf07ab6770186d13e62a1cc70d851532cad5c0b | O=C(c1ccco1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-C(-C)-N(-[CH2;D2;+0:1]-[C;D1;H3:2])-C(-C)-C.Cl-[C;H0;D3;+0:3](=[O;D1;H0:4])-[c:5](:[c:6]):[#8;a:7]:[c:8].[C;D1;H3:9]-[C:10]1-[C:11]-[C:12](-[NH;D2;+0:13]-[c:14](:[c:15]):[c:16])-[c:17]:[c:18](:[c:19])-[NH;D2;+0:20]-1.[OH2;D0;+0:21]>>[C;D1;H3:9]-[C:10]1-[C:11]-[C:12](-[N;H0;D3;+0:13](-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;H... | 83 | [{"value": 83.0, "product": "O1C(=CC=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C(C)=O)C1=CC=CC=C1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To a solution of (±)-cis-(2-Methyl-1,2,3,4-tetrahydro-quinolin-4-yl)-phenyl-amine (430 mg, 1.83 mmol) in dichloromethane (18 mL) at room temperature was added diisopropylethylamine (318 uL, 1.83 mmol) followed by 2-furoyl chloride. It was allowed to let stir at room temperature for 12 h. The mixture was poured into wat... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine.Secondary amine.Tertiary amine | Tertiary amide.Tertiary amide | c1ccc2c(c1)CCCN2 | c1ccc2c(c1)CCC[NH]2 | c1ccccc1.c1ccoc1.c1ccc2c(c1)CCC[NH]2 | HCl | ClCCl | null | 12 | CCN(C(C)C)C(C)C.C[C@H]1C[C@@H](Nc2ccccc2)c2ccccc2N1.O.O=C(Cl)c1ccco1>ClCCl>CC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccco2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1fb80b431d5b444e92a070f5b8a78d59 | CC(=O)Cl.C[C@H]1C[C@@H](Nc2ccccc2)c2ccccc2N1C(=O)c1ccco1>>CC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccco2)c2ccccc21 | O.C(C)(=O)Cl.O1C(=CC=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)NC1=CC=CC=C1)C.C(C)(C)N(CC)C(C)C>>O1C(=CC=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C(C)=O)C1=CC=CC=C1)C | Cl[C:2]([CH3:1])=[O:3].[NH:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[C@@H:11]1[CH2:12][C@H:13]([CH3:14])[N:15]([C:16](=[O:17])[c:18]2[cH:19][cH:20][cH:21][o:22]2)[c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]21>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[C@@H:11]1[CH2:12][C@H:13]([CH3:14])[N:15]([C:1... | CC(=O)Cl.C[C@H]1C[C@@H](Nc2ccccc2)c2ccccc2N1C(=O)c1ccco1 | CC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccco2)c2ccccc21 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccco1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:10]>>[C:4]-[C:5](-[N;H0;D3;+0:6](-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[c:7](:[c:8]):[c:9])-[c:10] | 61.4 | [{"value": 57.0, "product": "O1C(=CC=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C(C)=O)C1=CC=CC=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.4, "product": "O1C(=CC=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C(C)=O)C1=CC=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of (±)-cis-furan-2-yl-(2-methyl-4-phenylamino-3,4-dihydro-2H-quinolin-1-yl)-methanone (360 mg, 1.0 mmol) in methylene chloride (5 mL) was added diisopropylethylamine (1.9 mL, 10 mmol) followed by acetyl chloride (388 uL, 5 mmol). The mixture was stirred at room temperature over night. The mixture was pour... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccoc1.c1ccc2c(c1)CCC[NH]2 | HCl | C(Cl)Cl | null | null | CC(=O)Cl.C[C@H]1C[C@@H](Nc2ccccc2)c2ccccc2N1C(=O)c1ccco1>C(Cl)Cl>CC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccco2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2575977be9a34eada0d3c030887879c7 | CC[C@H]1C[C@@H](N(C(C)=O)c2ccccc2)c2ccccc2N1C(=O)c1sc(-c2cnccn2)nc1C>>CC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2sc(-c3cnccn3)nc2C)c2ccccc21 | C(C)[C@@H]1N(C2=CC=CC=C2[C@@H](C1)N(C(C)=O)C1=CC=CC=C1)C(=O)C1=C(N=C(S1)C1=NC=CN=C1)C.O1C(=CC=C1)C(=O)Cl>>C[C@@H]1N(C2=CC=CC=C2[C@@H](C1)N(C(C)=O)C1=CC=CC=C1)C(=O)C1=C(N=C(S1)C1=NC=CN=C1)C | C[CH2:14][C@H:13]1[CH2:12][C@@H:11]([N:4]([C:2]([CH3:1])=[O:3])[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[c:35]2[c:30]([cH:31][cH:32][cH:33][cH:34]2)[N:15]1[C:16](=[O:17])[c:18]1[s:19][c:20](-[c:21]2[cH:22][n:23][cH:24][cH:25][n:26]2)[n:27][c:28]1[CH3:29]>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[... | CC[C@H]1C[C@@H](N(C(C)=O)c2ccccc2)c2ccccc2N1C(=O)c1sc(-c2cnccn2)nc1C | CC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2sc(-c3cnccn3)nc2C)c2ccccc21 | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C(c1cnc(-c2cnccn2)s1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-[CH2;D2;+0:1]-[C:2](-[C:3])-[#7:4](-[C:5]=[O;D1;H0:6])-[c:7]>>[C:3]-[C:2](-[CH3;D1;+0:1])-[#7:4](-[C:5]=[O;D1;H0:6])-[c:7] | null | [] | null | null | null | null | (±)-Cis-N-[2-ethyl-1-(4-methyl-2-pyrazin-2-yl-thiazole-5-carbonyl)-1,2,3,4-tetrahydro-quinolin-4-yl]-N-phenyl-acetamide was made following general procedure A, substituting 4-methyl-2-(2-pyrazinyl)-1,3-thiazole-5-carbonyl chloride for 2-furoyl chloride.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1cscn1.c1cnccn1.c1ccc2c(c1)CCC[NH]2 | Other | null | null | null | CC[C@H]1C[C@@H](N(C(C)=O)c2ccccc2)c2ccccc2N1C(=O)c1sc(-c2cnccn2)nc1C>>CC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2sc(-c3cnccn3)nc2C)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d28d66c20b9943fc926c65ed8495c10c | CC1CC(N(C(=O)CO)c2ccccc2)c2ccccc2N1C(=O)c1ccc(F)cc1>>C[C@H]1C[C@@H](N(C(=O)CO)c2ccccc2)c2ccccc2N1C(=O)c1ccc(F)cc1 | C(C)(=O)OCC(=O)Cl.FC1=CC=C(C(=O)N2C(CC(C3=CC=CC=C23)N(C(CO)=O)C2=CC=CC=C2)C)C=C1.FC1=CC=C(C(=O)Cl)C=C1.C(C)(=O)Cl.O1C(=CC=C1)C(=O)Cl>>FC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(CO)=O)C2=CC=CC=C2)C)C=C1 | [CH3:1][CH:2]1[CH2:3][CH:4]([N:5]([C:6](=[O:7])[CH2:8][OH:9])[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[N:22]1[C:23](=[O:24])[c:25]1[cH:26][cH:27][c:28]([F:29])[cH:30][cH:31]1>>[CH3:1][C@H:2]1[CH2:3][C@@H:4]([N:5]([C:6](=[O:7])[CH2:8][OH:9])[c:10]2[cH:11][cH:12][cH:13][cH:14]... | CC1CC(N(C(=O)CO)c2ccccc2)c2ccccc2N1C(=O)c1ccc(F)cc1 | C[C@H]1C[C@@H](N(C(=O)CO)c2ccccc2)c2ccccc2N1C(=O)c1ccc(F)cc1 | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | null | null | [] | null | null | null | null | (±)-N-[1-(4-fluoro-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-2-hydroxy-N-phenyl-acetamide was made following general procedure A substituting 4-fluorobenzoyl chloride for 2-furoyl chloride and acetoxyacetyl chloride for acetyl chloride.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ccc2c(c1)CCC[NH]2.c1ccccc1 | null | null | null | null | CC1CC(N(C(=O)CO)c2ccccc2)c2ccccc2N1C(=O)c1ccc(F)cc1>>C[C@H]1C[C@@H](N(C(=O)CO)c2ccccc2)c2ccccc2N1C(=O)c1ccc(F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4e35c2b5ec1047f3870898d97fed7bac | CC[C@H]1C[C@@H](C(C)C(=O)Nc2ccccc2)c2ccccc2N1C(=O)c1cccnc1>>CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2cccnc2)c2ccccc21 | C(CC)(=O)Cl.C(C)[C@@H]1N(C2=CC=CC=C2[C@@H](C1)C(C(=O)NC1=CC=CC=C1)C)C(=O)C=1C=NC=CC1.N1=CC(=CC=C1)Cl.C(C)(=O)Cl.O1C(=CC=C1)C(=O)Cl>>C[C@@H]1N(C2=CC=CC=C2[C@@H](C1)N(C(CC)=O)C1=CC=CC=C1)C(=O)C=1C=NC=CC1 | C[CH2:15][C@H:14]1[CH2:13][C@@H:12]([CH:2]([CH3:1])[C:3](=[O:4])[NH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[c:30]2[c:25]([cH:26][cH:27][cH:28][cH:29]2)[N:16]1[C:17](=[O:18])[c:19]1[cH:20][cH:21][cH:22][n:23][cH:24]1>>[CH3:1][CH2:2][C:3](=[O:4])[N:5]([c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@H:14](... | CC[C@H]1C[C@@H](C(C)C(=O)Nc2ccccc2)c2ccccc2N1C(=O)c1cccnc1 | CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2cccnc2)c2ccccc21 | null | null | null | Miscellaneous | OtherReaction | 32fece39de0f49f9e7ef15a495d62763f3f0bef4f24bac43aae52b9d127b312f | 7fae2ddae661851fbaf2a59d877a8345033038358ec191ec2c5e2351a33f569b | O=C(c1cccnc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-[CH2;D2;+0:1]-[C:2]1-[C:3]-[C@@H;D3;+0:4](-[CH;D3;+0:5](-[C;D1;H3:6])-[C:7](=[O;D1;H0:8])-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12])-[c:13](:[c:14]):[c:15]-[#7:16]-1-[C:17]=[O;D1;H0:18]>>[C;D1;H3:6]-[CH2;D2;+0:5]-[C:7](=[O;D1;H0:8])-[N;H0;D3;+0:9](-[C@@H;D3;+0:4]1-[C:3]-[C:2](-[CH3;D1;+0:1])-[#7:16](-[C:17]=[O;D1;H0:18])-[... | null | [] | null | null | null | null | (±)-Cis-[2-ethyl-1-(pyridine-3-carbonyl)-1,2,3,4-tetrahydro-quinolin-4-yl]-N-phenyl-propionamide was made following general procedure A substituting 3-pyridinyl chloride for 2-furoyl chloride and propionyl chloride for acetyl chloride.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Tertiary amide | c1ccc2c(c1)CCC[NH]2 | c1ccc2c(c1)CCC[NH]2 | c1ccccc1.c1ccncc1.c1ccc2c(c1)CCC[NH]2 | Other | null | null | null | CC[C@H]1C[C@@H](C(C)C(=O)Nc2ccccc2)c2ccccc2N1C(=O)c1cccnc1>>CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2cccnc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-367a282312274d3c879236cf8fb82974 | CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OC)c(F)c2)c2ccccc21.COc1ccc(C(=O)Cl)cc1F>>CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2cccc(OCF)c2)c2ccccc21 | C(CC)(=O)Cl.FC=1C=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(CC)=O)C2=CC=CC=C2)C)C=CC1OC.FC=1C=C(C(=O)Cl)C=CC1OC.C(C)(=O)Cl.O1C(=CC=C1)C(=O)Cl>>FCOC=1C=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(CC)=O)C2=CC=CC=C2)C)C=CC1 | CO[c:22]1[cH:21][cH:20][c:19]([C:17]([N:16]2[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:5]([C:3]([CH2:2][CH3:1])=[O:4])[c:6]3[cH:7][cH:8][cH:9][cH:10][cH:11]3)[c:33]3[c:28]2[cH:29][cH:30][cH:31][cH:32]3)=[O:18])[cH:27][c:23]1F.C[O:24]c1ccc(C(=O)Cl)c[c:25]1[F:26]>>[CH3:1][CH2:2][C:3](=[O:4])[N:5]([c:6]1[cH:7][cH:8][cH:9][cH... | CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OC)c(F)c2)c2ccccc21.COc1ccc(C(=O)Cl)cc1F | CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2cccc(OCF)c2)c2ccccc21 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 43b1f9bddc90103cd7ddd41a698fada63f32dc28dcbb28e997d1056d00d6eb4a | c9d3c1c0489a34084c35312557f2d1d020968105c809839f4243dffc35982739 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-O-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](-[C:5](-[#7:6])=[O;D1;H0:7]):[c:8]:[c;H0;D3;+0:9]:1-F.C-[O;H0;D2;+0:10]-c1:c:c:c(-C(-Cl)=O):c:[c;H0;D3;+0:11]:1-[F;D1;H0:12]>>[#7:6]-[C:5](=[O;D1;H0:7])-[c:4]1:[c:3]:[c:2]:[cH;D2;+0:1]:[c;H0;D3;+0:9](-[O;H0;D2;+0:10]-[CH2;D2;+0:11]-[F;D1;H0:12]):[c:8]:1 | null | [] | null | null | null | null | (±)-Cis-N-[1-(3-fluoro-4-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-phenyl-propionamide was made following general procedure A substituting 3-fluoro-4-methoxybenzoyl chloride for 2-furoyl chloride and propionyl chloride for acetyl chloride.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aromatic halide.Aromatic halide.Ether.Ether | Primary halide.Ether | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HF | null | null | null | CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OC)c(F)c2)c2ccccc21.COc1ccc(C(=O)Cl)cc1F>>CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2cccc(OCF)c2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-73fd8fecce2d48ac93c09fc0a7960966 | CCOC(=O)N1CCC(c2ccc(C(=O)N3c4ccccc4[C@H](N(C(=O)CC)c4ccccc4)C[C@@H]3C)cc2)CC1>>CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(C3CCNCC3)cc2)c2ccccc21 | C(C)OC(=O)N1CCC(CC1)C1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C(CC)=O)C1=CC=CC=C1)C.C(C)OC(=O)N1CCC(CC1)C1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C(CC)=O)C1=CC=CC=C1)C.I[Si](C)(C)C>>C[C@@H]1N(C2=CC=CC=C2[C@@H](C1)N(C(CC)=O)C1=CC=CC=C1)C(C1=CC=C(C=C1)C1CCNCC1)=O | CCOC(=O)[N:26]1[CH2:25][CH2:24][CH:23]([c:22]2[cH:21][cH:20][c:19]([C:17]([N:16]3[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:5]([C:3]([CH2:2][CH3:1])=[O:4])[c:6]4[cH:7][cH:8][cH:9][cH:10][cH:11]4)[c:36]4[c:31]3[cH:32][cH:33][cH:34][cH:35]4)=[O:18])[cH:30][cH:29]2)[CH2:28][CH2:27]1>>[CH3:1][CH2:2][C:3](=[O:4])[N:5]([c:6]1[c... | CCOC(=O)N1CCC(c2ccc(C(=O)N3c4ccccc4[C@H](N(C(=O)CC)c4ccccc4)C[C@@H]3C)cc2)CC1 | CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(C3CCNCC3)cc2)c2ccccc21 | null | null | C(C)#N | Reduction | Hydrogenolysis of tertiary amines | 6dc5c07be2bf2a2ccc4ff166fd44281ea50e6dda805f74758334dcde1ad7a582 | 20c36f41eeb07c3ba4437b51ba72e8ff3c22d0b27e7197b0e9af3127f331149f | O=C(c1ccc(C2CCNCC2)cc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | 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] | null | [] | null | null | null | null | (±)-Cis-N-[2-methyl-1-(4-piperidin-4-yl-benzoyl)-1,2,3,4-tetrahydro-quinolin-4-yl]-N-phenyl-propionamide was prepared from (±)-cis-4-{4-[2-methyl-4-(phenyl-propionyl-amino)-3,4-dihydro-2H-quinoline-1-carbonyl]-phenyl}-piperidine-1-carboxylic acid ethyl ester. (±)-Cis-4-{4-[2-methyl-4-(phenyl-propionyl-amino)-3,4-dihydr... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccccc1.c1ccccc1.C1CCNCC1.c1ccc2c(c1)CCC[NH]2 | HO- | C(C)#N | null | null | CCOC(=O)N1CCC(c2ccc(C(=O)N3c4ccccc4[C@H](N(C(=O)CC)c4ccccc4)C[C@@H]3C)cc2)CC1>C(C)#N>CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(C3CCNCC3)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-827d3689fd1b434982c9c48ed847e029 | CC(=O)Cl.NN1CCCCC1>>NC(=O)CN1CCCCC1 | C([O-])(O)=O.[Na+].C(C)(C)N(CC)C(C)C.N1(CCCCC1)N.C(C)(=O)Cl>>N1(CCCCC1)CC(=O)N | Cl[C:2](=[O:3])[CH3:4].[NH2:1][N:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1>>[NH2:1][C:2](=[O:3])[CH2:4][N:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1 | CC(=O)Cl.NN1CCCCC1 | NC(=O)CN1CCCCC1 | null | null | C(Cl)Cl | Acylation | OtherReaction | 8b7d5514d87a925c0420829af26733388dfd75f01a0767d3fe8956f101d6629c | e5c25677803e61babaad51b064f83863eb4497268195d36f9f21f00b1069e47a | C1CCNCC1 | Cl-[C;H0;D3;+0:1](-[CH3;D1;+0:2])=[O;D1;H0:3].[C:4]-[C:5]-[N;H0;D3;+0:6](-[NH2;D1;+0:7])-[C:8]-[C:9]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:2]-[C;H0;D3;+0:1](-[NH2;D1;+0:7])=[O;D1;H0:3])-[C:8]-[C:9] | 100 | [{"value": 100.0, "product": "N1(CCCCC1)CC(=O)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of the piperidine amine obtained above (676 mg, 1.59 mmol) in methylene chloride (25 mL) was added diisopropylethylamine (616 mg, 849 uL, 4.77 mmol), followed by acetyl chloride (162 mg, 156 uL, 2.06 mmol). The mixture was stirred at room temperature over night. The reaction mixture was poured into satura... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Hydrazine | Primary amide.Tertiary amine | C1CC[NH]CC1 | C1CC[NH]CC1 | C1CC[NH]CC1 | HCl | C(Cl)Cl | null | null | CC(=O)Cl.NN1CCCCC1>C(Cl)Cl>NC(=O)CN1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-74cf2a8ed51c46379e5143067e800f17 | CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc([N+](=O)[O-])cc2)c2ccccc21>>CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N)cc2)c2ccccc21 | C[C@@H]1N(C2=CC=CC=C2[C@@H](C1)N(C(CC)=O)C1=CC=CC=C1)C(C1=CC=C(C=C1)[N+](=O)[O-])=O>>NC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(CC)=O)C2=CC=CC=C2)C)C=C1 | O=[N+:23]([O-])[c:22]1[cH:21][cH:20][c:19]([C:17]([N:16]2[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:5]([C:3]([CH2:2][CH3:1])=[O:4])[c:6]3[cH:7][cH:8][cH:9][cH:10][cH:11]3)[c:31]3[c:26]2[cH:27][cH:28][cH:29][cH:30]3)=[O:18])[cH:25][cH:24]1>>[CH3:1][CH2:2][C:3](=[O:4])[N:5]([c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[C@@H:12]1... | CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc([N+](=O)[O-])cc2)c2ccccc21 | CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N)cc2)c2ccccc21 | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 86 | [{"value": 86.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | (±)-Cis-N-[1-(4-amino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-phenyl-propionamide was prepared from (±)-cis-N-[2-methylmethyl-1-(4-nitro-benzoyl)-1,2,3,4-tetrahydro-quinolin-4-yl]-N-phenyl-propionamide. (±)-Cis-N-[2-methyl-1-(4-nitro-benzoyl)-1,2,3,4-tetrahydro-quinolin-4-yl]-N-phenyl-propionamide (200 mg... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | [Pd].C(C)O | null | null | CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc([N+](=O)[O-])cc2)c2ccccc21>[Pd].C(C)O>CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8829c1768c024d90ac6b20c3195368cf | CC(=O)Cl.CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N)cc2)c2ccccc21>>CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(NC(C)=O)cc2)c2ccccc21 | C(C)N(CC)CC.NC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(CC)=O)C2=CC=CC=C2)C)C=C1.NC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(CC)=O)C2=CC=CC=C2)C)C=C1.C(C)(=O)Cl>>C(C)(=O)NC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(CC)=O)C2=CC=CC=C2)C)C=C1 | Cl[C:24]([CH3:25])=[O:26].[CH3:1][CH2:2][C:3](=[O:4])[N:5]([c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([NH2:23])[cH:27][cH:28]2)[c:29]2[cH:30][cH:31][cH:32][cH:33][c:34]21>>[CH3:1][CH2:2][C:3](=[O:4])[N:5]([c:6]1[cH:7][cH:8][cH:9][cH:10][... | CC(=O)Cl.CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N)cc2)c2ccccc21 | CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(NC(C)=O)cc2)c2ccccc21 | null | null | O1CCCC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 46 | [{"value": 46.0, "product": "C(C)(=O)NC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(CC)=O)C2=CC=CC=C2)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | (±)-Cis-N-[1-(4-acetylamino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-phenyl-propionamide was prepared from (±)-cis-N-[1-(4-amino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-phenyl-propionamide. To a solution of (±)-cis-N-[1-(4-amino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-phenyl-pro... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HCl | O1CCCC1 | null | 8 | CC(=O)Cl.CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N)cc2)c2ccccc21>O1CCCC1>CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(NC(C)=O)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-afd5bdb5e9ec4016b8f7918cf852fbd9 | CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N)cc2)c2ccccc21.CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N)cc2)c2ccccc21.CCC(=O)O>>CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(-n3c(C)ccc3C)cc2)c2ccccc21 | NC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(CC)=O)C2=CC=CC=C2)C)C=C1.NC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(CC)=O)C2=CC=CC=C2)C)C=C1.C(CC)(=O)O.C1=CC=CC=C1>>CC=1N(C(=CC1)C)C1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(CC)=O)C2=CC=CC=C2)C)C=C1 | [CH3:1][CH2:2][C:3](=[O:4])[N:5]([c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([NH2:23])[cH:30][cH:31]2)[c:32]2[cH:33][cH:34][cH:35][cH:36][c:37]21.Nc1ccc(C(=O)N2c3ccccc3[C@H](N(C(=O)[CH2:28][CH3:29])c3ccccc3)C[C@@H]2[CH3:25])cc1.O=[C:24](O... | CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N)cc2)c2ccccc21.CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N)cc2)c2ccccc21.CCC(=O)O | CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(-n3c(C)ccc3C)cc2)c2ccccc21 | null | null | null | C-C Coupling | OtherReaction | 16a13f13bd674386af51fe2e696231ee34c5fd93d09332408df064455b84a965 | b0c8191f272b36b270edc62d5fbc09fbff0891556a7d8513b38018083a26d939 | O=C(c1ccc(-n2cccc2)cc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | N-c1:c:c:c(-C(=O)-N2-[C@H](-[CH3;D1;+0:1])-C-[C@H](-N(-C(=O)-[CH2;D2;+0:2]-[C;D1;H3:3])-c3:c:c:c:c:c:3)-c3:c:c:c:c:c:3-2):c:c:1.O-[C;H0;D3;+0:4](=O)-[CH2;D2;+0:5]-[CH3;D1;+0:6].[NH2;D1;+0:7]-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[C;D1;H3:3]-[c;H0;D3;+0:2]1:[cH;D2;+0:6]:[cH;D2;+0:5]:[c;H0;D3;+0:4](-[CH3;D1;+0:1])... | 80 | [{"value": 80.0, "product": "CC=1N(C(=CC1)C)C1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(CC)=O)C2=CC=CC=C2)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | (±)-Cis-N-{1-[4-(2,5-dimethyl-pyrrol-1-yl)-benzoyl]-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl}-N-phenyl-propionamide was prepared from (±)-cis-N-[1-(4-amino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-phenyl-propionamide. A solution of (±)-cis-N-[1-(4-amino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary amide.Tertiary amide.Primary amine.Primary amine | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCCN2 | c1ccc[nH]1 | c1ccccc1.c1ccccc1.c1ccc[nH]1.c1ccc2c(c1)CCC[NH]2 | HO- | null | null | null | CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N)cc2)c2ccccc21.CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N)cc2)c2ccccc21.CCC(=O)O>>CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(-n3c(C)ccc3C)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b6c2f061c4224b129271530af5a78add | CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N)cc2)c2ccccc21.CCC(C=O)CC>>CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(NCC(CC)CC)cc2)c2ccccc21 | C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+].NC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(CC)=O)C2=CC=CC=C2)C)C=C1.C(C)C(C=O)CC.NC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(CC)=O)C2=CC=CC=C2)C)C=C1.C(C)(=O)O>>C(C)C(CNC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(CC)=O)C2=CC=CC=C2)C)C=C1)CC | [CH3:1][CH2:2][C:3](=[O:4])[N:5]([c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([NH2:23])[cH:30][cH:31]2)[c:32]2[cH:33][cH:34][cH:35][cH:36][c:37]21.O=[CH:24][CH:25]([CH2:26][CH3:27])[CH2:28][CH3:29]>>[CH3:1][CH2:2][C:3](=[O:4])[N:5]([c:6]1[... | CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N)cc2)c2ccccc21.CCC(C=O)CC | CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(NCC(CC)CC)cc2)c2ccccc21 | null | null | ClCCl | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | O=[CH;D2;+0:1]-[C:2](-[C:3])-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:3]-[C:2](-[C:4])-[CH2;D2;+0:1]-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 83 | [{"value": 83.0, "product": "C(C)C(CNC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(CC)=O)C2=CC=CC=C2)C)C=C1)CC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | (±)-Cis-N-{1-[4-(2-ethyl-butylamino)-benzoyl]-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl}-N-phenyl-propionamide was prepared from (±)-cis-N-[1-(4-amino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-phenyl-propionamide. To a solution of (±)-cis-N-[1-(4-Amino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-p... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | ClCCl | null | null | CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N)cc2)c2ccccc21.CCC(C=O)CC>ClCCl>CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(NCC(CC)CC)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-290a98cf79694152b7a09c981c128001 | CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N)cc2)c2ccccc21.CCC=O>>CCCNc1ccc(C(=O)N2c3ccccc3[C@H](N(C(=O)CC)c3ccccc3)C[C@@H]2C)cc1 | C(C)C(C=O)CC.C(C)C(CNC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(CC)=O)C2=CC=CC=C2)C)C=C1)CC.NC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(CC)=O)C2=CC=CC=C2)C)C=C1.C(CC)=O>>C[C@@H]1N(C2=CC=CC=C2[C@@H](C1)N(C(CC)=O)C1=CC=CC=C1)C(C1=CC=C(C=C1)NCCC)=O | [NH2:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[N:11]2[c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[C@H:18]([N:19]([C:20](=[O:21])[CH2:22][CH3:23])[c:24]3[cH:25][cH:26][cH:27][cH:28][cH:29]3)[CH2:30][C@@H:31]2[CH3:32])[cH:33][cH:34]1.O=[CH:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[N... | CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N)cc2)c2ccccc21.CCC=O | CCCNc1ccc(C(=O)N2c3ccccc3[C@H](N(C(=O)CC)c3ccccc3)C[C@@H]2C)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | O=[CH;D2;+0:1]-[C:2]-[C;D1;H3:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | (±)-Cis-N-[2-methyl-1-(4-propylamino-benzoyl)-1,2,3,4-tetrahydro-quinolin-4-yl]-N-phenyl-propionamide was prepared from (±)-cis-N-[1-(4-amino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-phenyl-propionamide utilizing the reductive amination conditions described for the synthesis of (±)-cis-N-{1-[4-(2-ethyl-but... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | null | null | null | CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N)cc2)c2ccccc21.CCC=O>>CCCNc1ccc(C(=O)N2c3ccccc3[C@H](N(C(=O)CC)c3ccccc3)C[C@@H]2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4ac644dd7a2141dea55bcae060251f8c | CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N)cc2)c2ccccc21.COC(=O)C(C)Br>>COC(=O)C(C)Nc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccccc3)C[C@@H]2C)cc1 | NC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(CC)=O)C2=CC=CC=C2)C)C=C1.NC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(CC)=O)C2=CC=CC=C2)C)C=C1.C([O-])([O-])=O.[K+].[K+].BrC(C(=O)OC)C.O>>COC(C(C)NC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=CC=C1)C(C)=O)C)=O | C[CH2:24][C:23]([N:22]([C@H:21]1[c:20]2[c:15]([cH:16][cH:17][cH:18][cH:19]2)[N:14]([C:12]([c:11]2[cH:10][cH:9][c:8]([NH2:7])[cH:36][cH:35]2)=[O:13])[C@@H:33]([CH3:34])[CH2:32]1)[c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1)=[O:25].Br[CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH3:6]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH3:6])[NH:7][... | CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N)cc2)c2ccccc21.COC(=O)C(C)Br | COC(=O)C(C)Nc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccccc3)C[C@@H]2C)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 9460f8aba9fd9df7be6d8646a415233de3960f11da8401461639ab4fc047b682 | ce839c3e1095e851f2e0a7549fc2029a1d2ad47a8a3c3a46b00a63b754bc5ab7 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Br-[CH;D3;+0:1](-[C;D1;H3:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6].C-[CH2;D2;+0:7]-[C:8](=[O;D1;H0:9])-[#7:10](-[C:11])-[c:12].[NH2;D1;+0:13]-[c:14](:[c:15]):[c:16]>>[C;D1;H3:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:1](-[C;D1;H3:2])-[NH;D2;+0:13]-[c:14](:[c:15]):[c:16].[C:11]-[#7:10](-[c:12])-[C:8](-[CH3;D1;+0:7])=[O;... | 87 | [{"value": 87.0, "product": "COC(C(C)NC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=CC=C1)C(C)=O)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | (±)-Cis-2-{4-[4-(acetyl-phenyl-amino)-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl]-phenylamino}-propionic acid methyl ester was prepared from (±)-cis-N-[1-(4-amino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-phenyl-propionamide. A mixture of (±)-cis-N-[1-(4-amino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ester.Primary amine | Ester.Secondary amine | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HBr | CN(C=O)C | 100 | null | CCC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N)cc2)c2ccccc21.COC(=O)C(C)Br>CN(C=O)C>COC(=O)C(C)Nc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccccc3)C[C@@H]2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d0d62d144b904d71baaab5ea2a058acc | COc1cccc(CBr)c1.C[C@H]1C[C@@H](Nc2ccccc2)c2ccccc2N1>>COc1cccc(CN2c3ccccc3[C@H](N(C(C)=O)c3ccccc3)C[C@@H]2C)c1 | C([O-])([O-])=O.[K+].[K+].C[C@@H]1NC2=CC=CC=C2[C@@H](C1)NC1=CC=CC=C1.CN(C=O)C.BrCC1=CC(=CC=C1)OC.[I-].[K+]>>COC=1C=C(CN2[C@H](C[C@H](C3=CC=CC=C23)N(C(C)=O)C2=CC=CC=C2)C)C=CC1 | Br[CH2:8][c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:30]1.[NH:9]1[c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[C@H:16]([NH:17][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[CH2:27][C@@H:28]1[CH3:29]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][N:9]2[c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[C@H:16]([N:17]([C:18]([C... | COc1cccc(CBr)c1.C[C@H]1C[C@@H](Nc2ccccc2)c2ccccc2N1 | COc1cccc(CN2c3ccccc3[C@H](N(C(C)=O)c3ccccc3)C[C@@H]2C)c1 | null | null | null | Acylation | OtherReaction | 89ca2ffbea3ec23ad760d7d7bda55bf4f95e7326c1643fb731ace5c8f5519feb | 8edf1c26d504354a50dce45786b72c1940be701838dd8c41b265bdb7308b60c1 | c1ccc(CN2CC[C@@H](Nc3ccccc3)c3ccccc32)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[C:6]1-[C:7]-[C:8](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12])-[c:13]:[c:14](:[c:15])-[NH;D2;+0:16]-1>>[C;D1;H3:17]-[C:18](=[O;D1;H0:19])-[N;H0;D3;+0:9](-[C:8]1-[C:7]-[C:6](-[C;D1;H3:5])-[N;H0;D3;+0:16](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[c:14](:[c:15]):[c:13]-1)-[c:10](:[c:1... | null | [] | null | null | null | null | (±)-Cis-N-[1-(3-methoxy-benzyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-phenyl-acetamide was synthesized by dissolving (±)-cis-(2-methyl-1,2,3,4-tetrahydroquinol-4-yl)aniline in dimethylformamide and adding potassium carbonate (1.0-10.0 equiv.), and the 1-bromomethyl-3-methoxy-benzene (1.1-3.0 equiv), catalytic po... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine.Secondary amine | Tertiary amide.Tertiary amine | c1ccc2c(c1)CCCN2 | c1ccc2c(c1)CCC[NH]2 | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Br- | null | null | null | COc1cccc(CBr)c1.C[C@H]1C[C@@H](Nc2ccccc2)c2ccccc2N1>>COc1cccc(CN2c3ccccc3[C@H](N(C(C)=O)c3ccccc3)C[C@@H]2C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c31dcfe8f0c146db87d63e5e85a21e53 | CCN=C=O.COc1cccc(C(=O)N2c3ccccc3[C@H](Nc3ccccc3)C[C@@H]2C)c1>>CCNC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2cccc(OC)c2)c2ccccc21 | C(C)(=O)Cl.COC=1C=C(C=CC1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)NC1=CC=CC=C1)C.C(C)N=C=O>>C(C)NC(N(C1=CC=CC=C1)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC(=CC=C1)OC)=O)C)=O | [CH3:1][CH2:2][N:3]=[C:4]=[O:5].[NH:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[C@@H:13]1[CH2:14][C@H:15]([CH3:16])[N:17]([C:18](=[O:19])[c:20]2[cH:21][cH:22][cH:23][c:24]([O:25][CH3:26])[cH:27]2)[c:28]2[cH:29][cH:30][cH:31][cH:32][c:33]21>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[N:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]... | CCN=C=O.COc1cccc(C(=O)N2c3ccccc3[C@H](Nc3ccccc3)C[C@@H]2C)c1 | CCNC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2cccc(OC)c2)c2ccccc21 | null | null | CN(C)C=O | Acylation | Urea synthesis via isocyanate and secondary amine | 288f31369c46060b9009e57afc96d52a76d6a0243a2e1197ab47b0221bb8a3ee | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | [C;D1;H3:1]-[C:2]-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5].[C:6]-[C:7](-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11])-[c:12]>>[C:6]-[C:7](-[N;H0;D3;+0:8](-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:3]-[C:2]-[C;D1;H3:1])-[c:9](:[c:10]):[c:11])-[c:12] | null | [] | 90 | CELSIUS | null | null | (±)-Cis-3-ethyl-1-[1-(3-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-1-phenyl-urea was synthesized using general procedure A, substituting ethyl isocyanate for acetyl chloride using the following procedure. To a solution of (±)-cis-(3-methoxy-phenyl)-(2-methyl-4-anilino-3,4-dihydro-2H-quinolin-1-yl)-meth... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | null | CN(C)C=O | 90 | null | CCN=C=O.COc1cccc(C(=O)N2c3ccccc3[C@H](Nc3ccccc3)C[C@@H]2C)c1>CN(C)C=O>CCNC(=O)N(c1ccccc1)[C@@H]1C[C@H](C)N(C(=O)c2cccc(OC)c2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-06f6d363cb3f4d8fbdd4a0ddadbf7f8f | C=CNC(=O)OCc1ccccc1.CC=O.Nc1ccccc1>>C[C@H]1C[C@@H](NC(=O)OCc2ccccc2)c2ccccc2N1 | C(C1=CC=CC=C1)OC(NC=C)=O.NC1=CC=CC=C1.[O-]S(=O)(=O)[O-].[Na+].[Na+].B(F)(F)F.CCOCC.C(C)=O>>C(C1=CC=CC=C1)OC(N[C@@H]1C[C@@H](NC2=CC=CC=C12)C)=O | [CH2:3]=[CH:4][NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.O=[CH:2][CH3:1].[cH:16]1[cH:17][cH:18][cH:19][cH:20][c:21]1[NH2:22]>>[CH3:1][C@H:2]1[CH2:3][C@@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[NH:22]1 | C=CNC(=O)OCc1ccccc1.CC=O.Nc1ccccc1 | C[C@H]1C[C@@H](NC(=O)OCc2ccccc2)c2ccccc2N1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 10a367808e4d8a02f921e4f22ccec96cb0760c79632f6e1bfbd759fd1bea15ff | afc6fb3b06bcafaed087853b7812fac61e988e823b4d4d1a5152296d73d10689 | O=C(N[C@@H]1CCNc2ccccc21)OCc1ccccc1 | O=[CH;D2;+0:1]-[C;D1;H3:2].[#8:3]-[C:4](=[O;D1;H0:5])-[#7:6]-[CH;D2;+0:7]=[CH2;D1;+0:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[cH;D2;+0:12]:[c:13]:[c:14]>>[#8:3]-[C:4](=[O;D1;H0:5])-[#7:6]-[C@@H;D3;+0:7]1-[CH2;D2;+0:8]-[C@H;D3;+0:1](-[C;D1;H3:2])-[NH;D2;+0:9]-[c:10](:[c:11]):[c;H0;D3;+0:12]-1:[c:13]:[c:14] | 33.8 | [{"value": 33.0, "product": "C(C1=CC=CC=C1)OC(N[C@@H]1C[C@@H](NC2=CC=CC=C12)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 33.8, "product": "C(C1=CC=CC=C1)OC(N[C@@H]1C[C@@H](NC2=CC=CC=C12)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -25 | CELSIUS | 1 | HOUR | Aniline (3.64 mL, 39.97 mmol, 1.0 equ) was dissolved in methylene chloride (100 mL) and Na2SO4 (2 g) was added and cooled to −25° C. Acetaldehyde (2.23 mL, 39.97 mmol, 1.0 equ.) was added to the solution and stirred for 1 h at −25° C. Sodium sulfate was filtered off and N-vinyl-carbamic acid benzyl ester (7.07 g, 39.97... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aldehyde.Primary amine | Secondary amine | c1ccccc1 | c1ccc2c(c1)CCCN2 | c1ccccc1.c1ccc2c(c1)CCCN2 | HO- | C(Cl)Cl | -25 | 1 | C=CNC(=O)OCc1ccccc1.CC=O.Nc1ccccc1>C(Cl)Cl>C[C@H]1C[C@@H](NC(=O)OCc2ccccc2)c2ccccc2N1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cd63f102ed484888810a8935670de1da | CN(C)c1ccc(C(=O)Cl)cc1.C[C@H]1C[C@@H](NC(=O)OCc2ccccc2)c2ccccc2N1>>C[C@H]1C[C@@H](NC(=O)OCc2ccccc2)c2ccccc2N1C(=O)c1ccc(N(C)C)cc1 | O.CN(C1=CC=C(C(=O)Cl)C=C1)C.C(C1=CC=CC=C1)OC(N[C@@H]1C[C@@H](NC2=CC=CC=C12)C)=O.C(C)(C)N(CC)C(C)C>>C(C1=CC=CC=C1)OC(N[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)N(C)C)=O)C)=O | Cl[C:23](=[O:24])[c:25]1[cH:26][cH:27][c:28]([N:29]([CH3:30])[CH3:31])[cH:32][cH:33]1.[CH3:1][C@H:2]1[CH2:3][C@@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[NH:22]1>>[CH3:1][C@H:2]1[CH2:3][C@@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]2[cH:11]... | CN(C)c1ccc(C(=O)Cl)cc1.C[C@H]1C[C@@H](NC(=O)OCc2ccccc2)c2ccccc2N1 | C[C@H]1C[C@@H](NC(=O)OCc2ccccc2)c2ccccc2N1C(=O)c1ccc(N(C)C)cc1 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | 20af49e2ebd8e13ce8273786fd70e980d9c80eb9362be37fe2fe9cf2d75c9b8d | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(N[C@@H]1CCN(C(=O)c2ccccc2)c2ccccc21)OCc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7](-[C;D1;H3:8])-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[C:6]-[C:7](-[C;D1;H3:8])-[N;H0;D3;+0:9](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[c:10](:[c:11]):[c:12] | 89 | [{"value": 89.0, "product": "C(C1=CC=CC=C1)OC(N[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)N(C)C)=O)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of (±)-cis-(2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl)-carbamic acid benzyl ester (500 mg, 1.68 mmol) in methylene chloride (20 mL) at room temperature was added diisopropylethylamine (542 mg, 749 uL, 4.2 mmol) followed by 4-dimethylaminobenzoyl chloride and stirred at room temperature until no starting m... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)CCCN2 | c1ccc2c(c1)CCC[NH]2 | c1ccccc1.c1ccc2c(c1)CCC[NH]2.c1ccccc1 | HCl | C(Cl)Cl | null | null | CN(C)c1ccc(C(=O)Cl)cc1.C[C@H]1C[C@@H](NC(=O)OCc2ccccc2)c2ccccc2N1>C(Cl)Cl>C[C@H]1C[C@@H](NC(=O)OCc2ccccc2)c2ccccc2N1C(=O)c1ccc(N(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4e4a6aa273e64d5ea72cc4632fb25e8e | C[C@H]1C[C@@H](NC(=O)OCc2ccccc2)c2ccccc2N1C(=O)c1ccc(N(C)C)cc1>>C[C@H]1C[C@@H](N)c2ccccc2N1C(=O)c1ccc(N(C)C)cc1 | C(C1=CC=CC=C1)OC(N[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)N(C)C)=O)C)=O>>CN(C1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N)C)C=C1)C | O=C(OCc1ccccc1)[NH:5][C@@H:4]1[CH2:3][C@H:2]([CH3:1])[N:12]([C:13](=[O:14])[c:15]2[cH:16][cH:17][c:18]([N:19]([CH3:20])[CH3:21])[cH:22][cH:23]2)[c:11]2[c:6]1[cH:7][cH:8][cH:9][cH:10]2>>[CH3:1][C@H:2]1[CH2:3][C@@H:4]([NH2:5])[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[N:12]1[C:13](=[O:14])[c:15]1[cH:16][cH:17][c:18]([N:19]([... | C[C@H]1C[C@@H](NC(=O)OCc2ccccc2)c2ccccc2N1C(=O)c1ccc(N(C)C)cc1 | C[C@H]1C[C@@H](N)c2ccccc2N1C(=O)c1ccc(N(C)C)cc1 | null | null | C(C)O | Reduction | Hydrogenolysis of amides/imides/carbamates | 087b6600ba91d3df931fe6979f2445c192cbfd59e04fd2d8a10f7c7573ac669f | 4e549866ec1acadec4c84aaf8495992a28ec78d8ea5ef1b9f44dd843b0dcb7d4 | O=C(c1ccccc1)N1CCCc2ccccc21 | O=C(-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:1]-[C:2](-[C:3])-[c:4]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[c:4] | 92 | [{"value": 92.0, "product": "CN(C1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N)C)C=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.8, "product": "CN(C1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N)C)C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | (±)-Cis-[1-(4-dimethylamino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-carbamic acid benzyl ester (665 mg, 1.49 mmol) was dissolved in ethanol (30 mL). The resulting solution was evacuated and backfilled with argon. A catalytic amount of palladium on carbon (10%) was added. The vessel was once again evacuated ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | c1ccccc1 | null | c1ccc2c(c1)CCC[NH]2.c1ccccc1 | HO- | C(C)O | null | 18 | C[C@H]1C[C@@H](NC(=O)OCc2ccccc2)c2ccccc2N1C(=O)c1ccc(N(C)C)cc1>C(C)O>C[C@H]1C[C@@H](N)c2ccccc2N1C(=O)c1ccc(N(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-96b71d3e08354fd7bf6e627018cf69a0 | C[C@H]1C[C@@H](N)c2ccccc2N1C(=O)c1ccc(N(C)C)cc1.OB(O)c1ccc(Cl)cc1>>C[C@H]1C[C@@H](Nc2ccc(Cl)cc2)c2ccccc2N1C(=O)c1ccc(N(C)C)cc1 | C(C)(=O)OCC.CN(C1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N)C)C=C1)C.ClC1=CC=C(C=C1)B(O)O.N1=CC=CC=C1>>CN(C1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)NC2=CC=C(C=C2)Cl)C)C=C1)C | [CH3:1][C@H:2]1[CH2:3][C@@H:4]([NH2:5])[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[N:19]1[C:20](=[O:21])[c:22]1[cH:23][cH:24][c:25]([N:26]([CH3:27])[CH3:28])[cH:29][cH:30]1.OB(O)[c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1>>[CH3:1][C@H:2]1[CH2:3][C@@H:4]([NH:5][c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[c:13]2[c... | C[C@H]1C[C@@H](N)c2ccccc2N1C(=O)c1ccc(N(C)C)cc1.OB(O)c1ccc(Cl)cc1 | C[C@H]1C[C@@H](Nc2ccc(Cl)cc2)c2ccccc2N1C(=O)c1ccc(N(C)C)cc1 | null | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-] | CN(C)C=O | Heteroatom Alkylation and Arylation | Petasis reaction with amines and boronic acids | f5ae67a51de553a156f239a36ff1b30b0ec21b32d6467ebb95abe227e16748df | e74ce03b343a41c63fb42720bde3cd7e68ada25a9dc3f3bcf817625520d2a637 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | O-B(-O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7](-[NH2;D1;+0:8])-[c:9]>>[C:6]-[C:7](-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[c:9] | 22 | [{"value": 22.0, "product": "CN(C1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)NC2=CC=C(C=C2)Cl)C)C=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 21.0, "product": "CN(C1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)NC2=CC=C(C=C2)Cl)C)C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 1 | HOUR | To a solution of (±)-cis-1-(4-dimethylamino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-4-aminoquinoline (423 mg, 1.36 mmol) in DMF (15 mL, dry) was added 4-chlorophenylboronic acid (425 mg, 2.72 mmol), pyridine (322 mg, 330 uL, 4.08 mmol) and copper(II)acetate (494 mg, 2.72 mmol). The heterogeneous green mixture was stirred ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Boronic acid | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2c(c1)CCC[NH]2.c1ccccc1 | HO-.B | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].CN(C)C=O | 60 | 1 | C[C@H]1C[C@@H](N)c2ccccc2N1C(=O)c1ccc(N(C)C)cc1.OB(O)c1ccc(Cl)cc1>C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].CN(C)C=O>C[C@H]1C[C@@H](Nc2ccc(Cl)cc2)c2ccccc2N1C(=O)c1ccc(N(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-120369491031444abd6f94e7364ffc57 | CC(=O)Cl.C[C@H]1C[C@@H](Nc2ccc(Cl)cc2)c2ccccc2N1C(=O)c1ccc(N(C)C)cc1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N(C)C)cc2)c2ccccc21 | C(C)(=O)Cl.CN(C1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)NC2=CC=C(C=C2)Cl)C)C=C1)C.C(C)(C)N(CC)C(C)C>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)N(C)C)=O)C | Cl[C:2]([CH3:1])=[O:3].[NH:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([N:23]([CH3:24])[CH3:25])[cH:26][cH:27]2)[c:28]2[cH:29][cH:30][cH:31][cH:32][c:33]21>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]... | CC(=O)Cl.C[C@H]1C[C@@H](Nc2ccc(Cl)cc2)c2ccccc2N1C(=O)c1ccc(N(C)C)cc1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N(C)C)cc2)c2ccccc21 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:10]>>[C:4]-[C:5](-[N;H0;D3;+0:6](-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[c:7](:[c:8]):[c:9])-[c:10] | 34 | [{"value": 34.0, "product": "ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)N(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a solution of (±)-cis-1-(4-dimethylamino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-4-(N-4-chlorophenyl)aminoquinoline (120 mg, 0.29 mmol) in methylene chloride (2 mL) was added diisopropylethylamine (37 mg, 0.051 mL, 0.29 mmol) followed by acetyl chloride (2 mL). The mixture was stirred at rt 4 h. The mixture was concent... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HCl | C(Cl)Cl | null | 4 | CC(=O)Cl.C[C@H]1C[C@@H](Nc2ccc(Cl)cc2)c2ccccc2N1C(=O)c1ccc(N(C)C)cc1>C(Cl)Cl>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N(C)C)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fb8da0d1463e4b68b7ddae520b71cfb7 | COc1cccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)c1>>COc1cccc(C(=O)N2c3ccccc3C(N(C(C)=O)c3ccc(Cl)cc3)CC2C)c1 | ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC(=CC=C1)OC)=O)C.CN(C1=CC=C(C(=O)Cl)C=C1)C>>ClC1=CC=C(C=C1)N(C(C)=O)C1CC(N(C2=CC=CC=C12)C(C1=CC(=CC=C1)OC)=O)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]2[c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[C@H:17]([N:18]([C:19]([CH3:20])=[O:21])[c:22]3[cH:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]3)[CH2:29][C@@H:30]2[CH3:31])[cH:32]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]2[c:11]3[cH:12][cH:13][cH:... | COc1cccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)c1 | COc1cccc(C(=O)N2c3ccccc3C(N(C(C)=O)c3ccc(Cl)cc3)CC2C)c1 | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C(c1ccccc1)N1CCC(Nc2ccccc2)c2ccccc21 | null | null | [] | null | null | null | null | (±)-Cis-N-(4-chloro-phenyl)-N-[1-(3-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide was made following general procedure B, substituting 3-methoxybenzoyl chloride for 4-dimethylaminobenzoyl chloride.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | null | null | null | null | COc1cccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)c1>>COc1cccc(C(=O)N2c3ccccc3C(N(C(C)=O)c3ccc(Cl)cc3)CC2C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3480cf13a267421ab349ad761778e341 | CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.CCOC(=O)CCCBr>>CCOC(=O)CCCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(=O)CC)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | [H-].[Na+].C(C)O.ClC1=CC=C(C=C1)N(C(CC)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)O)=O)C.ClC1=CC=C(C=C1)N(C(CC)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)O)=O)C.BrCCCC(=O)OCC>>C(C)OC(CCCOC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C(CC)=O)C1=CC=C(C=C1)Cl)C)=O | [OH:9][c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])[N:16]2[c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]3[C@H:23]([N:24]([C:25](=[O:26])[CH2:27][CH3:28])[c:29]3[cH:30][cH:31][c:32]([Cl:33])[cH:34][cH:35]3)[CH2:36][C@@H:37]2[CH3:38])[cH:39][cH:40]1.Br[CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5]>>[CH3:1][CH2:2][O:3][C:... | CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.CCOC(=O)CCCBr | CCOC(=O)CCCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(=O)CC)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4](-[#8:5])=[O;D1;H0:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:5]-[C:4](=[O;D1;H0:6])-[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10] | 98 | [{"value": 98.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | (±)-Cis-4-(4-{4-[(4-chloro-phenyl)-propionyl-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-butyric acid ethyl ester was prepared from (±)-cis-N-(4-chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-propionamide. (±)-Cis-N-(4-chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methy... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HBr | CN(C)C=O | null | 0.5 | CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.CCOC(=O)CCCBr>CN(C)C=O>CCOC(=O)CCCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(=O)CC)c3ccc(Cl)cc3)C[C@@H]2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-71b3d92592b640719bd69b02e377bc0e | CCOC(=O)CCCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(=O)CC)c3ccc(Cl)cc3)C[C@@H]2C)cc1>>CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCC(=O)O)cc2)c2ccccc21 | C(C)OC(CCCOC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C(CC)=O)C1=CC=C(C=C1)Cl)C)=O.C(C)OC(CCCOC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C(CC)=O)C1=CC=C(C=C1)Cl)C)=O.C([O-])([O-])=O.[K+].[K+]>>ClC1=CC=C(C=C1)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCCCC(=O)O)C=C1)C)C(CC)=O | CC[O:30][C:28]([CH2:27][CH2:26][CH2:25][O:24][c:23]1[cH:22][cH:21][c:20]([C:18]([N:17]2[C@@H:15]([CH3:16])[CH2:14][C@@H:13]([N:5]([C:3]([CH2:2][CH3:1])=[O:4])[c:6]3[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]3)[c:38]3[c:33]2[cH:34][cH:35][cH:36][cH:37]3)=[O:19])[cH:32][cH:31]1)=[O:29]>>[CH3:1][CH2:2][C:3](=[O:4])[N:5]([c:6... | CCOC(=O)CCCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(=O)CC)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCC(=O)O)cc2)c2ccccc21 | null | null | O.CO | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 31 | [{"value": 31.0, "product": "ClC1=CC=C(C=C1)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCCCC(=O)O)C=C1)C)C(CC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | (±)-Cis-4-(4-{4-[(4-chloro-phenyl)-propionyl-amino]-2-methyl-3,4-dihydro-2H-quinoline1-carbonyl}-phenoxy)-butyric acid was prepared from (±)-cis-4-(4-{4-[(4-chloro-phenyl)-propionyl-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-butyric acid ethyl ester. Potassium carbonate (300 mg) was dissolved in wate... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | O.CO | null | null | CCOC(=O)CCCOc1ccc(C(=O)N2c3ccccc3[C@H](N(C(=O)CC)c3ccc(Cl)cc3)C[C@@H]2C)cc1>O.CO>CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCC(=O)O)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-51e47f6a1a494e2faa6806a79f4a4d80 | CC(C)(CO)CBr.CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCC(C)(C)CO)cc2)c2ccccc21 | C([O-])([O-])=O.[K+].[K+].ClC1=CC=C(C=C1)N(C(CC)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)O)=O)C.ClC1=CC=C(C=C1)N(C(CC)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)O)=O)C.BrCC(CO)(C)C>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCC(CO)(C)C)=O)C | Br[CH2:24][C:25]([CH3:26])([CH3:27])[CH2:28][OH:29].C[CH2:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([OH:23])[cH:30][cH:31]2)[c:32]2[cH:33][cH:34][cH:35][cH:36][c:37]21>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][... | CC(C)(CO)CBr.CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCC(C)(C)CO)cc2)c2ccccc21 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Br-[CH2;D2;+0:1]-[C:2](-[C:3])(-[C;D1;H3:4])-[C;D1;H3:5].C-[CH2;D2;+0:6]-[C:7](=[O;D1;H0:8])-[#7:9](-[C:10])-[c:11].[OH;D1;+0:12]-[c:13](:[c:14]):[c:15]>>[C:10]-[#7:9](-[c:11])-[C:7](-[CH3;D1;+0:6])=[O;D1;H0:8].[C:3]-[C:2](-[C;D1;H3:4])(-[C;D1;H3:5])-[CH2;D2;+0:1]-[O;H0;D2;+0:12]-[c:13](:[c:14]):[c:15] | 44 | [{"value": 44.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | null | null | (±)-Cis-N-(4-chloro-phenyl)-N-{1-[4-(3-hydroxy-2,2-dimethyl-propoxy)-benzoyl]-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl}-acetamide was prepared from (±)-cis-N-(4-chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-propionamide. (±)-Cis-N-(4-chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HBr | CN(C)C=O | 95 | null | CC(C)(CO)CBr.CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21>CN(C)C=O>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCC(C)(C)CO)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f033a46294a4424e8a38ee9aaa52c684 | CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.COC(=O)C(C)(C)CBr>>COC(=O)C(C)(C)COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | COC(C(CBr)(C)C)=O.ClC1=CC=C(C=C1)N(C(CC)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)O)=O)C.ClC1=CC=C(C=C1)N(C(CC)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)O)=O)C.C([O-])([O-])=O.[K+].[K+]>>COC(C(COC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C)(C)C)=O | C[CH2:26][C:25]([N:24]([C@H:23]1[c:22]2[c:17]([cH:18][cH:19][cH:20][cH:21]2)[N:16]([C:14]([c:13]2[cH:12][cH:11][c:10]([OH:9])[cH:39][cH:38]2)=[O:15])[C@@H:36]([CH3:37])[CH2:35]1)[c:28]1[cH:29][cH:30][c:31]([Cl:32])[cH:33][cH:34]1)=[O:27].Br[CH2:8][C:5]([C:3]([O:2][CH3:1])=[O:4])([CH3:6])[CH3:7]>>[CH3:1][O:2][C:3](=[O:4... | CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.COC(=O)C(C)(C)CBr | COC(=O)C(C)(C)COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Br-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[C:5](=[O;D1;H0:6])-[#8:7]-[C;D1;H3:8].C-[CH2;D2;+0:9]-[C:10](=[O;D1;H0:11])-[#7:12](-[C:13])-[c:14].[OH;D1;+0:15]-[c:16](:[c:17]):[c:18]>>[C;D1;H3:8]-[#8:7]-[C:5](=[O;D1;H0:6])-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[CH2;D2;+0:1]-[O;H0;D2;+0:15]-[c:16](:[c:17]):[c:18].[C:1... | 8 | [{"value": 8.0, "product": "COC(C(COC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | null | null | (±)-Cis-3-(4-{4-[acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-2,2-dimethyl-propionic acid methyl ester was prepared from (±)-cis-N-(4-chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-propionamide. (±)-Cis-N-(4-chloro-phenyl)-N-[1-(4-hydroxy-ben... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HBr | CN(C)C=O | 95 | null | CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21.COC(=O)C(C)(C)CBr>CN(C)C=O>COC(=O)C(C)(C)COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-32e3e8d4fa7245f6885e553fcbc5041c | CC(=O)Cl.COc1cccc(C(=O)N2c3ccccc3[C@H](Nc3ccccn3)C[C@@H]2C)c1>>COc1cccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccccn3)C[C@@H]2C)c1 | COC=1C=C(C=CC1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)NC1=NC=CC=C1)C.C(C)(=O)Cl>>COC=1C=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(C)=O)C2=NC=CC=C2)C)C=CC1 | Cl[C:19]([CH3:20])=[O:21].[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]2[c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[C@H:17]([NH:18][c:22]3[cH:23][cH:24][cH:25][cH:26][n:27]3)[CH2:28][C@@H:29]2[CH3:30])[cH:31]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]2[c:11]3[cH:12][cH:13][cH:14][cH:... | CC(=O)Cl.COc1cccc(C(=O)N2c3ccccc3[C@H](Nc3ccccn3)C[C@@H]2C)c1 | COc1cccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccccn3)C[C@@H]2C)c1 | null | null | null | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccn2)c2ccccc21 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5](-[NH;D2;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10])-[c:11]>>[C:4]-[C:5](-[N;H0;D3;+0:6](-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[c:7](:[c:8]):[#7;a:9]:[c:10])-[c:11] | null | [] | null | null | null | null | Pd2(dba)3 (0.05 equ.), and rac-BINAP (0.1 equ.) were added to a flask with degassed toluene and stirred for 1 h. To the above solution was added 2-bromopyridine (1.1 equ.) and NaOtBu (1.1 equ.) and stirred for 30 min. (±)-Cis-(4-amino-2-methyl-3,4-dihydro-2H-quinolin-1-yl)-(3-methoxy-phenyl)-methanone was dissolved in ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccncc1.c1ccc2c(c1)CCC[NH]2 | HCl | null | null | null | CC(=O)Cl.COc1cccc(C(=O)N2c3ccccc3[C@H](Nc3ccccn3)C[C@@H]2C)c1>>COc1cccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccccn3)C[C@@H]2C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-263b4f7f4c5245ea8effe447b074428c | CCC(=O)Cl.COc1cccc(C(=O)N2c3ccccc3[C@H](Nc3ccc(Cl)cn3)C[C@@H]2C)c1>>COc1cccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cn3)C[C@@H]2C)c1 | ClC=1C=CC(=NC1)N[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC(=CC=C1)OC)C.C(CC)(=O)Cl>>ClC=1C=CC(=NC1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC(=CC=C1)OC)=O)C | C[CH2:20][C:19](Cl)=[O:21].[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]2[c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[C@H:17]([NH:18][c:22]3[cH:23][cH:24][c:25]([Cl:26])[cH:27][n:28]3)[CH2:29][C@@H:30]2[CH3:31])[cH:32]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]2[c:11]3[cH:12][cH:13][c... | CCC(=O)Cl.COc1cccc(C(=O)N2c3ccccc3[C@H](Nc3ccc(Cl)cn3)C[C@@H]2C)c1 | COc1cccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cn3)C[C@@H]2C)c1 | null | null | null | Acylation | OtherReaction | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccn2)c2ccccc21 | C-[CH2;D2;+0:1]-[C;H0;D3;+0:2](-Cl)=[O;D1;H0:3].[C:4]-[C:5](-[NH;D2;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10])-[c:11]>>[C:4]-[C:5](-[N;H0;D3;+0:6](-[C;H0;D3;+0:2](-[CH3;D1;+0:1])=[O;D1;H0:3])-[c:7](:[c:8]):[#7;a:9]:[c:10])-[c:11] | null | [] | null | null | null | null | To a flask was added Pd2(dba)3 (molar 0.05 equ.), and rac-BINAP (0.1 equ.) in degassed toluene and stirred for 1 h. To the above solution was added 2,5-dichloropyridinepyridine (1.1 equ.) and NaOtBu (1.1 equ.) and stirred for 30 min. The corresponding amine, (±)-cis-(4-amino-2-methyl-3,4-dihydro-2H-quinolin-1-yl)-(3-me... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccncc1.c1ccc2c(c1)CCC[NH]2 | HCl | null | null | null | CCC(=O)Cl.COc1cccc(C(=O)N2c3ccccc3[C@H](Nc3ccc(Cl)cn3)C[C@@H]2C)c1>>COc1cccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cn3)C[C@@H]2C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-38ef0511f95740f39c826894bf1ee9e4 | COc1ccc(C(=O)N2c3cccc(C)c3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1>>COc1ccc(C(=O)N2c3cc(C)ccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | CN(C1=CC=C(C(=O)Cl)C=C1)C.ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC(=C12)C)C(C1=CC=C(C=C1)OC)=O)C.NC1=CC=CC=C1.COC1=CC=C(C(=O)Cl)C=C1>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC(=CC=C12)C)C(C1=CC=C(C=C1)OC)=O)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[N:9]2[c:10]3[cH:11][cH:15][cH:14][c:12]([CH3:13])[c:16]3[C@H:17]([N:18]([C:19]([CH3:20])=[O:21])[c:22]3[cH:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]3)[CH2:29][C@@H:30]2[CH3:31])[cH:32][cH:33]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[N:9]2[c:10]3[cH:11][c:12]([C... | COc1ccc(C(=O)N2c3cccc(C)c3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | COc1ccc(C(=O)N2c3cc(C)ccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | null | null | null | Miscellaneous | OtherReaction | 79503c5bbd93d082bf8197f3441c50e1f6cf2c3dcd153866fb3370eae24e26fc | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | [C;D1;H3:1]-[c;H0;D3;+0:2]1:[c:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[c:6]2:[c;H0;D3;+0:7]:1-[C:8](-[#7:9]-[C:10](-[C;D1;H3:11])=[O;D1;H0:12])-[C:13]-[C:14]-[#7:15]-2-[C:16]=[O;D1;H0:17]>>[C;D1;H3:1]-[c;H0;D3;+0:2]1:[c:3]:[cH;D2;+0:4]:[c;H0;D3;+0:7]2:[c:6](:[cH;D2;+0:5]:1)-[#7:15](-[C:16]=[O;D1;H0:17])-[C:14]-[C:13]-[C:8]-2-[#7... | null | [] | null | null | null | null | (±)-Cis-N-(4-chloro-phenyl)-N-[1-(4-methoxy-benzoyl)-2,5-dimethyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide was made following general procedure B, substituting 3-toluidine for aniline and 4-methoxybenzoyl chloride for 4-dimethylaminobenzoyl chloride. The reaction was non-selective and also (±)-cis-N-(4-chloro-phenyl... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2c(c1)CCC[NH]2 | c1ccc2c(c1)CCC[NH]2 | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | null | null | null | null | COc1ccc(C(=O)N2c3cccc(C)c3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1>>COc1ccc(C(=O)N2c3cc(C)ccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e910182a178145818307b5e304d64f29 | CN(C)c1ccc(C(=O)Cl)cc1.COc1ccc(C(=O)Cl)cc1.Nc1ccccc1>>COc1ccc(C(=O)N2c3cccc(C)c3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | COC1=CC=C(C(=O)Cl)C=C1.ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC(=CC=C12)C)C(C1=CC=C(C=C1)OC)=O)C.CN(C1=CC=C(C(=O)Cl)C=C1)C.NC1=CC=CC=C1>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC(=C12)C)C(C1=CC=C(C=C1)OC)=O)C.ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC(=CC=C12)C)C(C1=CC=C(C=C1)OC)=O)C | [C:48](=[O:54])([c:58]1[cH:57][cH:56][c:55]([N:51]([CH3:50])[CH3:53])[cH:61][cH:60]1)[Cl:59].Cl[C:40]([c:39]1[cH:38][cH:37][c:36]([O:35][CH3:34])[cH:66][cH:65]1)=[O:41].[NH2:42][c:43]1[cH:44][cH:45][cH:46][cH:47][cH:49]1>>[CH3:34][O:35][c:36]1[cH:37][cH:38][c:39]([C:40](=[O:41])[N:42]2[c:43]3[cH:44][cH:45][cH:46][c:47]... | CN(C)c1ccc(C(=O)Cl)cc1.COc1ccc(C(=O)Cl)cc1.Nc1ccccc1 | COc1ccc(C(=O)N2c3cccc(C)c3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | null | null | null | Acylation | OtherReaction | c02605f28509cb45c0705e3739d0c93f15e46daff81767c35772be1a402979f0 | 727332e0bdbab460e01b92629aaea07cc604a97aa6e2606a2b027cd820543559 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[CH3;D1;+0:6]-[N;H0;D3;+0:7](-[CH3;D1;+0:8])-[c:9]1:[c:10]:[c:11]:[c;H0;D3;+0:12](-[C;H0;D3;+0:13](-[Cl;H0;D1;+0:14])=[O;H0;D1;+0:15]):[c:16]:[c:17]:1.[NH2;D1;+0:18]-[c:19]1:[c:20]:[c:21]:[c:22]:[cH;D2;+0:23]:[cH;D2;+0:24]:1>>[C;D1;H3:25]-[C:26]1-[C:27]-[C@@H;D3;+0:6]... | null | [] | null | null | null | null | (±)-Cis-N-(4-chloro-phenyl)-N-[1-(4-methoxy-benzoyl)-2,7-dimethyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide was made following general procedure B, substituting 3-toluidine for aniline and 4-methoxybenzoyl chloride for 4-dimethylaminobenzoyl chloride. The reaction was non-selective, and also (±)-cis-N-(4-chloro-pheny... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary amine.Tertiary amine | Aromatic halide.Tertiary amide.Tertiary amide | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccc2c(c1)CCC[NH]2 | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | null | null | null | null | CN(C)c1ccc(C(=O)Cl)cc1.COc1ccc(C(=O)Cl)cc1.Nc1ccccc1>>COc1ccc(C(=O)N2c3cccc(C)c3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1a23ecf6bd324c0486f05fa17bd820c7 | CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccc(OCC(=O)OC)cc21>>CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccc(OCC(=O)O)cc21 | COC(COC=1C=C2[C@@H](C[C@@H](N(C2=CC1)C(C1=CC=C(C=C1)F)=O)C)N(C(CC)=O)C1=CC=C(C=C1)Cl)=O.COC(COC=1C=C2[C@@H](C[C@@H](N(C2=CC1)C(C1=CC=C(C=C1)F)=O)C)N(C(CC)=O)C1=CC=C(C=C1)Cl)=O.[OH-].[Na+]>>ClC1=CC=C(C=C1)N([C@@H]1C[C@@H](N(C2=CC=C(C=C12)OCC(=O)O)C(C1=CC=C(C=C1)F)=O)C)C(CC)=O | C[O:35][C:33]([CH2:32][O:31][c:30]1[cH:29][cH:28][c:27]2[c:37]([cH:36]1)[C@H:13]([N:5]([C:3]([CH2:2][CH3:1])=[O:4])[c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1)[CH2:14][C@H:15]([CH3:16])[N:17]2[C:18](=[O:19])[c:20]1[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]1)=[O:34]>>[CH3:1][CH2:2][C:3](=[O:4])[N:5]([c:6]1[cH:7][cH:... | CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccc(OCC(=O)OC)cc21 | CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccc(OCC(=O)O)cc21 | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 94 | [{"value": 94.0, "product": "ClC1=CC=C(C=C1)N([C@@H]1C[C@@H](N(C2=CC=C(C=C12)OCC(=O)O)C(C1=CC=C(C=C1)F)=O)C)C(CC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | (±)-Cis-[4-[(4-chloro-phenyl)-propionyl-amino]-1-(4-fluoro-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-6-yloxy]-acetic acid was prepared from (±)-cis-[4-[(4-chloro-phenyl)-propionyl-amino]-1-(4-fluoro-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-6-yloxy]-acetic acid methyl ester. To a solution of (±)-cis-[4-[(4-chlo... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | CO | null | 3 | CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccc(OCC(=O)OC)cc21>CO>CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccc(OCC(=O)O)cc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-50b82e49bcce46dd8ab596a9d676d6fe | CCOC(=O)C(C)(C)Oc1ccc2c(c1)[C@H](N(C(=O)CC)c1ccc(Cl)cc1)C[C@H](C)N2C(=O)c1ccc(F)cc1>>CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccc(OC(C)(C)C(=O)O)cc21 | ClC1=CC=C(C=C1)N([C@@H]1C[C@@H](N(C2=CC=C(C=C12)OCC(=O)O)C(C1=CC=C(C=C1)F)=O)C)C(CC)=O.C(C)OC(C(C)(C)OC=1C=C2[C@@H](C[C@@H](N(C2=CC1)C(C1=CC=C(C=C1)F)=O)C)N(C(CC)=O)C1=CC=C(C=C1)Cl)=O>>ClC1=CC=C(C=C1)N([C@@H]1C[C@@H](N(C2=CC=C(C=C12)OC(C(=O)O)(C)C)C(C1=CC=C(C=C1)F)=O)C)C(CC)=O | CC[O:37][C:35]([C:32]([O:31][c:30]1[cH:29][cH:28][c:27]2[c:39]([cH:38]1)[C@H:13]([N:5]([C:3]([CH2:2][CH3:1])=[O:4])[c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1)[CH2:14][C@H:15]([CH3:16])[N:17]2[C:18](=[O:19])[c:20]1[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]1)([CH3:33])[CH3:34])=[O:36]>>[CH3:1][CH2:2][C:3](=[O:4])[N:... | CCOC(=O)C(C)(C)Oc1ccc2c(c1)[C@H](N(C(=O)CC)c1ccc(Cl)cc1)C[C@H](C)N2C(=O)c1ccc(F)cc1 | CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccc(OC(C)(C)C(=O)O)cc21 | null | null | null | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | null | null | (±)-Cis-2-[4-[(4-chloro-phenyl)-propionyl-amino]-1-(4-fluoro-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-6-yloxy]-2-methyl-propionic acid was prepared from (±)-cis-2-[4-[(4-chloro-phenyl)-propionyl-amino]-1-(4-fluoro-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-6-yloxy]-2-methyl-propionic acid ethyl ester. The sapon... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | null | null | null | CCOC(=O)C(C)(C)Oc1ccc2c(c1)[C@H](N(C(=O)CC)c1ccc(Cl)cc1)C[C@H](C)N2C(=O)c1ccc(F)cc1>>CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccc(OC(C)(C)C(=O)O)cc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c7dd50cda3cc4df084e203a5b26f899c | CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccc(OCC(=O)OC)cc21.N>>CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccc(OCC(N)=O)cc21 | COC(COC=1C=C2[C@@H](C[C@@H](N(C2=CC1)C(C1=CC=C(C=C1)F)=O)C)N(C(CC)=O)C1=CC=C(C=C1)Cl)=O.N>>C(N)(=O)COC=1C=C2[C@@H](C[C@@H](N(C2=CC1)C(C1=CC=C(C=C1)F)=O)C)N(C(CC)=O)C1=CC=C(C=C1)Cl | CO[C:33]([CH2:32][O:31][c:30]1[cH:29][cH:28][c:27]2[c:37]([cH:36]1)[C@H:13]([N:5]([C:3]([CH2:2][CH3:1])=[O:4])[c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1)[CH2:14][C@H:15]([CH3:16])[N:17]2[C:18](=[O:19])[c:20]1[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]1)=[O:35].[NH3:34]>>[CH3:1][CH2:2][C:3](=[O:4])[N:5]([c:6]1[cH:7]... | CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccc(OCC(=O)OC)cc21.N | CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccc(OCC(N)=O)cc21 | null | null | CO | Acylation | OtherReaction | d5b10d4f469e7a196a3b04a6a9e159a7d90514b6df5b50c1197d4b1b774c04e1 | adc0ef6f6c1340dd2dbab737c85bf17fc842769181c5db1a2b4f82b391b28f9f | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4].[NH3;D0;+0:5]>>[#8:4]-[C:3]-[C;H0;D3;+0:1](-[NH2;D1;+0:5])=[O;D1;H0:2] | 76 | [{"value": 76.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | (±)-Cis-N-[6-carbamoylmethoxy-1-(4-fluoro-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-(4-chloro-phenyl)-propionamide was prepared from (±)-cis-4-[(4-chloro-phenyl)-propionyl-amino]-1-(4-fluoro-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-6-yloxy]-acetic acid ester. To solid (±)-cis-[4-[(4-chloro-phenyl)-prop... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HO- | CO | null | null | CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccc(OCC(=O)OC)cc21.N>CO>CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccc(OCC(N)=O)cc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9db6d5d4165a41d9a889c82f20e21d81 | CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccc(N3CCOCC3)cc21.CCC(=O)N(c1ccc(N(CC)CC)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccc(N(CC)CC)cc21>>CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccc(N(CC)CC)cc21 | N1CCOCC1.C(C)N(C=1C=C2[C@@H](C[C@@H](N(C2=CC1)C(C1=CC=C(C=C1)F)=O)C)N(C(CC)=O)C1=CC=C(C=C1)N(CC)CC)CC.ClC1=CC=C(C=C1)N(C(CC)=O)[C@@H]1C[C@@H](N(C2=CC=C(C=C12)N1CCOCC1)C(C1=CC=C(C=C1)F)=O)C.C(C)NCC>>ClC1=CC=C(C=C1)N(C(CC)=O)[C@@H]1C[C@@H](N(C2=CC=C(C=C12)N(CC)CC)C(C1=CC=C(C=C1)F)=O)C | C1C[N:31]([c:30]2[cH:29][cH:28][c:27]3[c:37]([cH:36]2)[C@H:13]([N:5]([C:3]([CH2:2][CH3:1])=[O:4])[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[CH2:14][C@H:15]([CH3:16])[N:17]3[C:18](=[O:19])[c:20]2[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]2)CCO1.CCC(=O)N(c1ccc(N(CC)CC)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccc(N([... | CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccc(N3CCOCC3)cc21.CCC(=O)N(c1ccc(N(CC)CC)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccc(N(CC)CC)cc21 | CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccc(N(CC)CC)cc21 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | efd76e2963b786dd6171a8a72562617283a1971e96ecbb3998266ebedcfc7125 | c53cfac120282988daea7947474e4981c55c68780205307a9609d5cf214b3a48 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-C-C(=O)-N(-[C@H]1-C-[C@H](-C)-N(-C(=O)-c2:c:c:c(-F):c:c:2)-c2:c:c:c(-N(-[CH2;D2;+0:1]-[C;D1;H3:2])-[CH2;D2;+0:3]-[C;D1;H3:4]):c:c:2-1)-c1:c:c:c(-N(-C-C)-C-C):c:c:1.[c:5]:[c:6](-[N;H0;D3;+0:7]1-C-C-O-C-C-1):[c:8]>>[C;D1;H3:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7](-[CH2;D2;+0:3]-[C;D1;H3:4])-[c:6](:[c:5]):[c:8] | null | [] | null | null | null | null | (±)-Cis-N-[6-diethylamino-1-(4-fluoro-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N(4-diethylamino-phenyl)-propionamide was made in the same way as (±)-cis-N-(4-chloro-phenyl)-N-[1 -(4-fluoro-benzoyl)-2-methyl-6-morpholin-4-yl-1,2,3,4-tetrahydro-quinolin-4-yl]-propionamide except diethylamine was substituted fo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Tertiary amide.Tertiary amide.Tertiary amine.Tertiary amine.Tertiary amine | Tertiary amine | C1COCC[NH]1.c1ccccc1.c1ccccc1.c1ccc2c(c1)CCCN2 | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HF | null | null | null | CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccc(N3CCOCC3)cc21.CCC(=O)N(c1ccc(N(CC)CC)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccc(N(CC)CC)cc21>>CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccc(N(CC)CC)cc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7f80f4ca960246edae8c256394ee132e | C=CC(=O)OC.CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccc(C=CC(=O)O)cc21>>CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccc(C=CC(=O)OC)cc21 | ClC1=CC=C(C=C1)N([C@@H]1C[C@@H](N(C2=CC=C(C=C12)C=CC(=O)O)C(C1=CC=C(C=C1)F)=O)C)C(CC)=O.BrC=1C=C2[C@@H](C[C@@H](N(C2=CC1)C(C1=CC=C(C=C1)F)=O)C)N(C(CC)=O)C1=CC=C(C=C1)Cl.BrC=1C=C2[C@@H](C[C@@H](N(C2=CC1)C(C1=CC=C(C=C1)F)=O)C)N(C(CC)=O)C1=CC=C(C=C1)Cl.C1(=CC=CC=C1)P(CCCP(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.C(C=C)(=O)OC>>... | [CH2:31]=[CH:32][C:33](=[O:34])[O:35][CH3:36].O=C(O)C=C[c:30]1[cH:29][cH:28][c:27]2[c:38]([cH:37]1)[C@H:13]([N:5]([C:3]([CH2:2][CH3:1])=[O:4])[c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1)[CH2:14][C@H:15]([CH3:16])[N:17]2[C:18](=[O:19])[c:20]1[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]1>>[CH3:1][CH2:2][C:3](=[O:4])[N:... | C=CC(=O)OC.CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccc(C=CC(=O)O)cc21 | CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccc(C=CC(=O)OC)cc21 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | CN(C)C=O | C-C Coupling | O-methylation | 4e23d12bae162def895de92701734e7f85ca2550b29fa0799f377287203cdcfc | 271e3ba7f993df4472e473adf24569183d3aab0b5124850797c108a882536876 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | O-C(=O)-C=C-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C:10]=[CH2;D1;+0:11]>>[C;D1;H3:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C:10]=[CH;D2;+0:11]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 44 | [{"value": 44.0, "product": "COC(C=CC=1C=C2[C@@H](C[C@@H](N(C2=CC1)C(C1=CC=C(C=C1)F)=O)C)N(C(CC)=O)C1=CC=C(C=C1)Cl)=O", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | (±)-Cis-3-[4-[(4-chloro-phenyl)-propionyl-amino]-1-(4-fluoro-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-6-yl]-acrylic acid was made from (±)-cis-N-[6-bromo-1-(4-fluoro-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-(4-chloro-phenyl)-propionamide. To a solution of (±)-cis-N-[6-bromo-1-(4-fluoro-benzoyl)-2-meth... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Vinyl | null | c1ccc2c(c1)CCC[NH]2 | c1ccc2c(c1)CCC[NH]2 | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HO- | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].CN(C)C=O | 80 | null | C=CC(=O)OC.CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccc(C=CC(=O)O)cc21>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].CN(C)C=O>CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccc(C=CC(=O)OC)cc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f314d735920a44cca0e0786ce89d3265 | CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccc(C=CC(=O)OC)cc21>>CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccc(C=CC(=O)O)cc21 | COC(C=CC=1C=C2[C@@H](C[C@@H](N(C2=CC1)C(C1=CC=C(C=C1)F)=O)C)N(C(CC)=O)C1=CC=C(C=C1)Cl)=O.C(=O)([O-])[O-].[K+].[K+]>>ClC1=CC=C(C=C1)N([C@@H]1C[C@@H](N(C2=CC=C(C=C12)C=CC(=O)O)C(C1=CC=C(C=C1)F)=O)C)C(CC)=O | C[O:35][C:33]([CH:32]=[CH:31][c:30]1[cH:29][cH:28][c:27]2[c:37]([cH:36]1)[C@H:13]([N:5]([C:3]([CH2:2][CH3:1])=[O:4])[c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1)[CH2:14][C@H:15]([CH3:16])[N:17]2[C:18](=[O:19])[c:20]1[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]1)=[O:34]>>[CH3:1][CH2:2][C:3](=[O:4])[N:5]([c:6]1[cH:7][cH... | CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccc(C=CC(=O)OC)cc21 | CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccc(C=CC(=O)O)cc21 | null | null | O.CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]=[C:5]-[c:6]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[C:4]=[C:5]-[c:6] | 9.1 | [{"value": 9.1, "product": "ClC1=CC=C(C=C1)N([C@@H]1C[C@@H](N(C2=CC=C(C=C12)C=CC(=O)O)C(C1=CC=C(C=C1)F)=O)C)C(CC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of (±)-cis-3-[4-[(4-chloro-phenyl)-propionyl-amino]-1-(4-fluoro-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-6-yl]-acrylic acid methyl ester (110 mg, 0.21 mmol) in 4 ml methanol was added 50 mg K2CO3, (0.36 mmol, in 2 ml water). The resulting reaction mixture was stirred at room temperature overnight. Th... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | O.CO | null | 8 | CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccc(C=CC(=O)OC)cc21>O.CO>CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccc(C=CC(=O)O)cc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-54ae29eb40e94ac4b695192d33829aa6 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N(C)C)cc2)c2cc(N3CCOCC3)ccc21.CCN(CC)c1ccc(N(C(C)=O)[C@@H]2C[C@H](C)N(C(=O)c3ccc(N(C)C)cc3)c3cc(N(CC)CC)ccc32)cc1.CCNCC>>CCN(CC)c1ccc2c(c1)N(C(=O)c1ccc(N(C)C)cc1)[C@@H](C)C[C@H]2N(C(C)=O)c1ccc(Cl)cc1 | N1CCOCC1.C(C)N(C1=CC=C2[C@@H](C[C@@H](N(C2=C1)C(C1=CC=C(C=C1)N(C)C)=O)C)N(C(C)=O)C1=CC=C(C=C1)N(CC)CC)CC.ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC(=CC=C12)N1CCOCC1)C(C1=CC=C(C=C1)N(C)C)=O)C.C(C)NCC>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC(=CC=C12)N(CC)CC)C(C1=CC=C(C=C1)N(C)C)=O)C | C1C[N:3]([c:6]2[cH:7][cH:8][c:9]3[c:10]([cH:11]2)[N:12]([C:13](=[O:14])[c:15]2[cH:16][cH:17][c:18]([N:19]([CH3:20])[CH3:21])[cH:22][cH:23]2)[C@@H:24]([CH3:25])[CH2:26][C@H:27]3[N:28]([C:29]([CH3:30])=[O:31])[c:32]2[cH:33][cH:34][c:35]([Cl:36])[cH:37][cH:38]2)CCO1.CCN(CC)c1ccc(N(C(C)=O)[C@@H]2C[C@H](C)N(C(=O)c3ccc(N(C)C... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N(C)C)cc2)c2cc(N3CCOCC3)ccc21.CCN(CC)c1ccc(N(C(C)=O)[C@@H]2C[C@H](C)N(C(=O)c3ccc(N(C)C)cc3)c3cc(N(CC)CC)ccc32)cc1.CCNCC | CCN(CC)c1ccc2c(c1)N(C(=O)c1ccc(N(C)C)cc1)[C@@H](C)C[C@H]2N(C(C)=O)c1ccc(Cl)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 11d320f23afe6af73b55c140707bb309928e9754a7f161babb31980236480ee6 | a231863537e19cc9af31abf5655fd391c5eedc0dcaffbdb0906d38ebe6000b4b | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-C-N(-C-C)-c1:c:c:c(-N(-C(-C)=O)-[C@H]2-C-[C@H](-C)-N(-C(=O)-c3:c:c:c(-N(-C)-C):c:c:3)-c3:c:c(-N(-C-C)-[CH2;D2;+0:1]-[C;D1;H3:2]):c:c:c:3-2):c:c:1.C-C-N-[CH2;D2;+0:3]-[C;D1;H3:4].[c:5]:[c:6](-[N;H0;D3;+0:7]1-C-C-O-C-C-1):[c:8]>>[C;D1;H3:4]-[CH2;D2;+0:3]-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[C;D1;H3:2])-[c:6](:[c:5]):[c:8] | null | [] | null | null | null | null | (±)-Cis-N-[7-diethylamino-1-(4-dimethylamino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-(4-diethylamino-phenyl)-acetamide was made in the same way as (±)-cis-N-(4-chloro-phenyl)-N-[1-(4-dimethylamino-benzoyl)-2-methyl-7-morpholin-4-yl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide except diethylamine was substi... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Tertiary amide.Tertiary amide.Secondary amine.Tertiary amine.Tertiary amine.Tertiary amine.Tertiary amine | Tertiary amine | C1COCC[NH]1.c1ccccc1.c1ccccc1.c1ccc2c(c1)CCCN2 | null | c1ccccc1.c1ccc2c(c1)CCC[NH]2.c1ccccc1 | HO- | null | null | null | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N(C)C)cc2)c2cc(N3CCOCC3)ccc21.CCN(CC)c1ccc(N(C(C)=O)[C@@H]2C[C@H](C)N(C(=O)c3ccc(N(C)C)cc3)c3cc(N(CC)CC)ccc32)cc1.CCNCC>>CCN(CC)c1ccc2c(c1)N(C(=O)c1ccc(N(C)C)cc1)[C@@H](C)C[C@H]2N(C(C)=O)c1ccc(Cl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f15c55a7229a43138f1c1bb39467f81b | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N(C)C)cc2)c2cc(O)ccc21.CCOC(=O)CCCBr>>CCOC(=O)COc1ccc2c(c1)N(C(=O)c1ccc(N(C)C)cc1)[C@@H](C)C[C@H]2N(C(C)=O)c1ccc(Cl)cc1 | C(C)OC(CCCOC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C(CC)=O)C1=CC=C(C=C1)Cl)C)=O.ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC(=CC=C12)O)C(C1=CC=C(C=C1)N(C)C)=O)C.BrCCCC(=O)OCC>>C(C)OC(COC1=CC=C2[C@@H](C[C@@H](N(C2=C1)C(C1=CC=C(C=C1)N(C)C)=O)C)N(C1=CC=C(C=C1)Cl)C(C)=O)=O | [OH:7][c:8]1[cH:9][cH:10][c:11]2[c:12]([cH:13]1)[N:14]([C:15](=[O:16])[c:17]1[cH:18][cH:19][c:20]([N:21]([CH3:22])[CH3:23])[cH:24][cH:25]1)[C@@H:26]([CH3:27])[CH2:28][C@H:29]2[N:30]([C:31]([CH3:32])=[O:33])[c:34]1[cH:35][cH:36][c:37]([Cl:38])[cH:39][cH:40]1.BrCC[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5]>>[CH3:1][CH2:2][O:... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N(C)C)cc2)c2cc(O)ccc21.CCOC(=O)CCCBr | CCOC(=O)COc1ccc2c(c1)N(C(=O)c1ccc(N(C)C)cc1)[C@@H](C)C[C@H]2N(C(C)=O)c1ccc(Cl)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Br-C-C-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | null | [] | null | null | null | null | (±)-Cis-[4-[acetyl-(4-chloro-phenyl)-amino]-1-(4-dimethylamino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-7-yloxy]-acetic acid ethyl ester was prepared from (±)-cis-N-(4-chloro-phenyl)-N-[1-(4-dimethylamino-benzoyl)-7-hydroxy-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide, following the alkylation conditions d... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1ccccc1.c1ccc2c(c1)CCC[NH]2.c1ccccc1 | HBr | null | null | null | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N(C)C)cc2)c2cc(O)ccc21.CCOC(=O)CCCBr>>CCOC(=O)COc1ccc2c(c1)N(C(=O)c1ccc(N(C)C)cc1)[C@@H](C)C[C@H]2N(C(C)=O)c1ccc(Cl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-69c1f7f68d5c4a3da58579363c6ad4b0 | CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccc(OCC(N)=O)cc21.CCOC(=O)COc1ccc2c(c1)N(C(=O)c1ccc(N(C)C)cc1)[C@@H](C)C[C@H]2N(C(C)=O)c1ccc(Cl)cc1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N(C)C)cc2)c2cc(OCC(N)=O)ccc21 | C(N)(=O)COC=1C=C2[C@@H](C[C@@H](N(C2=CC1)C(C1=CC=C(C=C1)F)=O)C)N(C(CC)=O)C1=CC=C(C=C1)Cl.C(C)OC(COC1=CC=C2[C@@H](C[C@@H](N(C2=C1)C(C1=CC=C(C=C1)N(C)C)=O)C)N(C1=CC=C(C=C1)Cl)C(C)=O)=O>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC(=CC=C12)OCC(=O)N)C(C1=CC=C(C=C1)N(C)C)=O)C)C1=CC=C(C=C1)Cl | CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)[c:38]2[c:28]1[cH:29][c:30]([O:31][CH2:32][C:33]([NH2:34])=[O:35])[cH:36][cH:37]2.CCOC(=O)COc1ccc2c(c1)[N:16]([C:17](=[O:18])[c:19]1[cH:20][cH:21][c:22]([N:23]([CH3:24])[CH3:25])[cH:26][cH:27]1)[C@@H:14]([CH3:15])[CH2:13][C@H:12]2[N:4]([C:2]([CH3:1])=[O:3])[c:5]1... | CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccc(OCC(N)=O)cc21.CCOC(=O)COc1ccc2c(c1)N(C(=O)c1ccc(N(C)C)cc1)[C@@H](C)C[C@H]2N(C(C)=O)c1ccc(Cl)cc1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N(C)C)cc2)c2cc(OCC(N)=O)ccc21 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 105408e964ac437f824a9922364526f556e96df203889ba34fcbafd6bba50fb9 | 75d17ddc511236e829264b8c8a9fcc5f5e6ae3e810b5d027a6937e62de8e6d83 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-C-C(=O)-N(-[C@H]1-C-[C@H](-C)-N(-C(=O)-c2:c:c:c(-F):c:c:2)-[c;H0;D3;+0:1]2:[c:2]:[c:3]:[c:4]:[c:5]:[c;H0;D3;+0:6]:2-1)-c1:c:c:c(-Cl):c:c:1.C-C-O-C(=O)-C-O-c1:c:c:c2:c(:c:1)-[N;H0;D3;+0:7](-[C:8](=[O;D1;H0:9])-[c:10])-[C:11](-[C;D1;H3:12])-[C:13]-[C@H;D3;+0:14]-2-[#7:15](-[c:16])-[C:17](-[C;D1;H3:18])=[O;D1;H0:19]>>[C... | null | [] | null | null | null | null | (±)-Cis-2-[4-[acetyl-(4-chloro-phenyl)-amino]-1-(4-dimethylamino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-7-yloxy]-acetamide was prepared from (±)-cis-[4-[acetyl-(4-chloro-phenyl)-amino]-1-(4-dimethylamino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-7-yloxy]-acetic acid ethyl ester, via the same amidation proced... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ester.Ether.Tertiary amide.Tertiary amide.Tertiary amide | Tertiary amide | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCCN2.c1ccc2c(c1)CCC[NH]2 | c1ccc2c(c1)CCC[NH]2 | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HF | null | null | null | CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccc(OCC(N)=O)cc21.CCOC(=O)COc1ccc2c(c1)N(C(=O)c1ccc(N(C)C)cc1)[C@@H](C)C[C@H]2N(C(C)=O)c1ccc(Cl)cc1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N(C)C)cc2)c2cc(OCC(N)=O)ccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ea57e68332c645b999b433b378d1e26d | CCOC(=O)COc1ccc2c(c1)N(C(=O)c1ccc(N(C)C)cc1)[C@@H](C)C[C@H]2N(C(C)=O)c1ccc(Cl)cc1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N(C)C)cc2)c2cc(OCC(=O)O)ccc21 | ClC1=CC=C(C=C1)N([C@@H]1C[C@@H](N(C2=CC=C(C=C12)OCC(=O)O)C(C1=CC=C(C=C1)F)=O)C)C(CC)=O.C(C)OC(COC1=CC=C2[C@@H](C[C@@H](N(C2=C1)C(C1=CC=C(C=C1)N(C)C)=O)C)N(C1=CC=C(C=C1)Cl)C(C)=O)=O>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC(=CC=C12)OCC(=O)O)C(C1=CC=C(C=C1)N(C)C)=O)C)C1=CC=C(C=C1)Cl | CC[O:35][C:33]([CH2:32][O:31][c:30]1[cH:29][c:28]2[c:38]([cH:37][cH:36]1)[C@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[CH2:13][C@H:14]([CH3:15])[N:16]2[C:17](=[O:18])[c:19]1[cH:20][cH:21][c:22]([N:23]([CH3:24])[CH3:25])[cH:26][cH:27]1)=[O:34]>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6]... | CCOC(=O)COc1ccc2c(c1)N(C(=O)c1ccc(N(C)C)cc1)[C@@H](C)C[C@H]2N(C(C)=O)c1ccc(Cl)cc1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N(C)C)cc2)c2cc(OCC(=O)O)ccc21 | null | null | null | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | null | null | (±)-Cis-[4-[acetyl-(4-chloro-phenyl)-amino]-1-(4-dimethylamino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-7-yloxy]-acetic acid was prepared from (±)-cis-[4-[acetyl-(4-chloro-phenyl)-amino]-1-(4-dimethylamino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-7-yloxy]-acetic acid ethyl ester following the saponification p... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | null | null | null | CCOC(=O)COc1ccc2c(c1)N(C(=O)c1ccc(N(C)C)cc1)[C@@H](C)C[C@H]2N(C(C)=O)c1ccc(Cl)cc1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(N(C)C)cc2)c2cc(OCC(=O)O)ccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5315f5b4e1174f36bad95a4458c713f7 | CCC(=O)OC[C@H]1C[C@@H](N(C(=O)CC)c2ccc(Cl)cc2)c2ccccc2N1C(=O)c1ccc(F)cc1>>CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](CO)N(C(=O)c2ccc(F)cc2)c2ccccc21 | ClC1=CC=C(C=C1)N([C@@H]1C[C@@H](N(C2=CC=C(C=C12)OCC(=O)O)C(C1=CC=C(C=C1)F)=O)C)C(CC)=O.ClC1=CC=C(C=C1)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)F)=O)COC(CC)=O)C(CC)=O>>ClC1=CC=C(C=C1)N(C(CC)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)F)=O)CO | CCC(=O)[O:17][CH2:16][C@H:15]1[CH2:14][C@@H:13]([N:5]([C:3]([CH2:2][CH3:1])=[O:4])[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[c:33]2[c:28]([cH:29][cH:30][cH:31][cH:32]2)[N:18]1[C:19](=[O:20])[c:21]1[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]1>>[CH3:1][CH2:2][C:3](=[O:4])[N:5]([c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11]... | CCC(=O)OC[C@H]1C[C@@H](N(C(=O)CC)c2ccc(Cl)cc2)c2ccccc2N1C(=O)c1ccc(F)cc1 | CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](CO)N(C(=O)c2ccc(F)cc2)c2ccccc21 | null | null | null | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[C:3]-[#7:4]>>[#7:4]-[C:3]-[C:2]-[OH;D1;+0:1] | null | [] | null | null | null | null | (±)-Cis-N-(4-chloro-phenyl)-N-[1-(4-fluoro-benzoyl)-2-hydroxymethyl-1,2,3,4-tetrahydro-quinolin-4-yl]-propionamide was prepared from (±)-cis-propionic acid 4-[(4-chloro-phenyl)-propionyl-amino]-1-(4-fluoro-benzoyl)-1,2,3,4-tetrahydro-quinolin-2-ylmethyl ester using the saponification conditions utilized in the synthesi... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HO- | null | null | null | CCC(=O)OC[C@H]1C[C@@H](N(C(=O)CC)c2ccc(Cl)cc2)c2ccccc2N1C(=O)c1ccc(F)cc1>>CCC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](CO)N(C(=O)c2ccc(F)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8401052c572846aba0ef57c8ae4131d5 | C[C@@H](COS(C)(=O)=O)NC(=O)OC(C)(C)C.[C-]#N>>C[C@@H](CC#N)NC(=O)OC(C)(C)C | C(C)(C)(C)OC(=O)N[C@H](COS(=O)(=O)C)C.[C-]#N.[Na+]>>C(C)(C)(C)OC(N[C@H](CC#N)C)=O | CS(=O)(=O)O[CH2:3][C@H:2]([CH3:1])[NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13].[C-:4]#[N:5]>>[CH3:1][C@@H:2]([CH2:3][C:4]#[N:5])[NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13] | C[C@@H](COS(C)(=O)=O)NC(=O)OC(C)(C)C.[C-]#N | C[C@@H](CC#N)NC(=O)OC(C)(C)C | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | CN(C=O)C | C-C Coupling | OtherReaction | 18f4bbb9c586d5002707644e5539611116bc9c01fc56c5a56ec0d1b0251f5f0b | 89d1e6e004e8ba10561e22cfb8893e96c375691951aae8f42243dfb0e0a04eec | null | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])-[#7:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11].[C-;H0;D1:12]#[N;D1;H0:13]>>[C;D1;H3:9]-[C:8](-[C;D1;H3:10])(-[C;D1;H3:11])-[#8:7]-[C:5](=[O;D1;H0:6])-[#7:4]-[C:2](-[C;D1;H3:3])-[CH2;D2;+0:1]-[C;H0;D2;+0:12]#[N;D1;H0:13] | null | [] | 35 | CELSIUS | 30 | MINUTE | Sodium cyanide (48.92 g, 0.421 mol) was added to dimethylformamide (DMF) (420 mL) and the mixture was stirred at 35° C. for 30 minutes. Tetrabutylammonium bromide (5.22 g, 0.016 mol) was added and the reaction mixture was stirred for an additional 2 h at 35° C. Methanesulfonic acid 2-(S)-tert-butoxycarbonylamino-propyl... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate | Nitrile | null | null | null | MsOH.HO- | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.CN(C=O)C | 35 | 0.5 | C[C@@H](COS(C)(=O)=O)NC(=O)OC(C)(C)C.[C-]#N>[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.CN(C=O)C>C[C@@H](CC#N)NC(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f96025ccacd64add8eb14a33108935cc | C[C@@H](CC#N)Nc1ccccc1.O=S(=O)(O)O>>C[C@@H](CC(N)=O)Nc1ccccc1 | C1(=CC=CC=C1)N[C@H](CC#N)C.S(O)(O)(=O)=O>>C1(=CC=CC=C1)N[C@H](CC(=O)N)C | [CH3:1][C@@H:2]([CH2:3][C:4]#[N:5])[NH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1.O=S(=O)(O)[OH:6]>>[CH3:1][C@@H:2]([CH2:3][C:4]([NH2:5])=[O:6])[NH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1 | C[C@@H](CC#N)Nc1ccccc1.O=S(=O)(O)O | C[C@@H](CC(N)=O)Nc1ccccc1 | null | null | O.C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 1d1793919e847ed86dcb16487e62464531560dbf4782f9a5875bfe7e0477a3ec | d6f9d146e8ef95e62f1a3ab55a7e3b4ceec8856a5f71b6dccd4ad850f945b658 | c1ccccc1 | O-S(=O)(=O)-[OH;D1;+0:1].[C:2]-[C:3]-[C;H0;D2;+0:4]#[N;H0;D1;+0:5]>>[C:2]-[C:3]-[C;H0;D3;+0:4](-[NH2;D1;+0:5])=[O;H0;D1;+0:1] | null | [] | null | null | 0.5 | HOUR | To a solution of (S)-3-phenylamino-butyronitrile (6.06 g, 0.0378 mol) in toluene (150 mL) was added a cooled solution of conc. sulfuric acid in H2O (20.12 mL H2SO4/3 mL)—(The ratio of toluene to acid/H2O is very important and should be followed strictly). Stir the biphasic mixture at room temperature for 0.5 h and warm... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amide | null | null | c1ccccc1 | Other | O.C1(=CC=CC=C1)C | null | 0.5 | C[C@@H](CC#N)Nc1ccccc1.O=S(=O)(O)O>O.C1(=CC=CC=C1)C>C[C@@H](CC(N)=O)Nc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8e1b62f87d064f4ca032f3815c55bcc1 | C[C@@H](CC(N)=O)Nc1ccccc1.O=C(Cl)OCc1ccccc1>>C[C@@H](CC(=O)NC(=O)OCc1ccccc1)Nc1ccccc1 | CC(C)([O-])C.[Li+].ClC(=O)OCC1=CC=CC=C1.C1(=CC=CC=C1)N[C@H](CC(=O)N)C.CC(C)([O-])C.[Li+]>>C(C1=CC=CC=C1)OC(NC(C[C@H](C)NC1=CC=CC=C1)=O)=O | [CH3:1][C@@H:2]([CH2:3][C:4](=[O:5])[NH2:6])[NH:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1.Cl[C:7](=[O:8])[O:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][C@@H:2]([CH2:3][C:4](=[O:5])[NH:6][C:7](=[O:8])[O:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[NH:17][c:18]1[cH:19][cH:20][cH:21][cH:2... | C[C@@H](CC(N)=O)Nc1ccccc1.O=C(Cl)OCc1ccccc1 | C[C@@H](CC(=O)NC(=O)OCc1ccccc1)Nc1ccccc1 | null | null | C1CCOC1 | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | ad1c02b16132fcebf06978727b6e3537fe24971c1b6b51ebd3c2feb87bf80211 | e0859034a1689c5b5e475fb10c80f10698b9f2f1df4607fb1088ad38d4759eaf | O=C(CCNc1ccccc1)NC(=O)OCc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[C:5]-[C:6](-[NH2;D1;+0:7])=[O;D1;H0:8]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6](-[C:5])=[O;D1;H0:8] | 82 | [{"value": 82.0, "product": "C(C1=CC=CC=C1)OC(NC(C[C@H](C)NC1=CC=CC=C1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | -10 | CELSIUS | null | null | A clean, dry and nitrogen gas purged flask was charged with (S)-3-phenylamino-butyramide (3.25 g, 0.018 mmol) in THF (65 mL) and the mixture was cooled to −10° C. Benzyl chloroformate (3.12 mL, 0.022 mmol) was then added followed by the slow addition of 1.0 M lithium tert-butoxide in THF solution (18 mL). The lithium t... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amide | Carbamic ester | null | null | c1ccccc1.c1ccccc1 | HCl | C1CCOC1 | -10 | null | C[C@@H](CC(N)=O)Nc1ccccc1.O=C(Cl)OCc1ccccc1>C1CCOC1>C[C@@H](CC(=O)NC(=O)OCc1ccccc1)Nc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-78c8ee5d4b2b4815abd0fa19411ab3ed | C[C@@H](CC(=O)NC(=O)OCc1ccccc1)Nc1ccccc1>>C[C@H]1C[C@@H](NC(=O)OCc2ccccc2)c2ccccc2N1 | C(C1=CC=CC=C1)OC(NC(C[C@H](C)NC1=CC=CC=C1)=O)=O.[BH4-].[Na+]>>C(C1=CC=CC=C1)OC(N[C@@H]1C[C@@H](NC2=CC=CC=C12)C)=O | O=[C:4]([CH2:3][C@H:2]([CH3:1])[NH:22][c:21]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1>>[CH3:1][C@H:2]1[CH2:3][C@@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[NH:22]1 | C[C@@H](CC(=O)NC(=O)OCc1ccccc1)Nc1ccccc1 | C[C@H]1C[C@@H](NC(=O)OCc2ccccc2)c2ccccc2N1 | null | null | C(C)O | C-C Coupling | OtherReaction | 97f8a9f9c50150a80669192eed2907fad81281a5555d63457333226a47ae997c | d9206c89bc8c29af05511b9e2eee5a949354ced9cafb338d4a7bf26515a328e5 | O=C(N[C@@H]1CCNc2ccccc21)OCc1ccccc1 | O=[C;H0;D3;+0:1](-[#7:2]-[C:3](-[#8:4])=[O;D1;H0:5])-[C:6]-[C:7]-[#7:8]-[c:9](:[c:10]):[cH;D2;+0:11]:[c:12]:[c:13]>>[#8:4]-[C:3](=[O;D1;H0:5])-[#7:2]-[C@@H;D3;+0:1]1-[C:6]-[C:7]-[#7:8]-[c:9](:[c:10]):[c;H0;D3;+0:11]-1:[c:12]:[c:13] | 94 | [{"value": 94.0, "product": "C(C1=CC=CC=C1)OC(N[C@@H]1C[C@@H](NC2=CC=CC=C12)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -10 | CELSIUS | 6 | HOUR | A clean, dry flask was charged with (S)-(3-phenylamino-butyryl)-carbamic acid benzyl ester (0.821 g, 2.63 mmol) followed by reagent grade ethanol (20 mL) and cooled to −10° C. Sodium borohydride (0.070 g, 1.84 mmol) was added to the solution in one portion. Nitrogen gas purging is maintained for 5 minutes. A solution o... | 10.6084/m9.figshare.5104873.v1 | null | Unsubstituted dicarboximide | null | c1ccccc1 | c1ccc2c(c1)CCCN2 | c1ccccc1.c1ccc2c(c1)CCCN2 | Other | C(C)O | -10 | 6 | C[C@@H](CC(=O)NC(=O)OCc1ccccc1)Nc1ccccc1>C(C)O>C[C@H]1C[C@@H](NC(=O)OCc2ccccc2)c2ccccc2N1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-96f5bfdea7b8462ea145cfeac3af6291 | CCOC(C)=O.C[C@H]1C[C@@H](N)c2ccccc2N1C(=O)c1ccc(F)cc1.OB(O)c1ccc(Cl)cc1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccccc21 | C(C)(=O)OCC.N[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)F)C.ClC1=CC=C(C=C1)B(O)O.N1=CC=CC=C1>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)F)=O)C | CCO[C:2]([CH3:1])=[O:3].[NH2:4][C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([F:23])[cH:24][cH:25]2)[c:26]2[cH:27][cH:28][cH:29][cH:30][c:31]21.OB(O)[c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1... | CCOC(C)=O.C[C@H]1C[C@@H](N)c2ccccc2N1C(=O)c1ccc(F)cc1.OB(O)c1ccc(Cl)cc1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccccc21 | null | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-] | CN(C)C=O | Acylation | OtherReaction | d5b79df0bcad37b68666465f98bdbf09561dfcc3b18a2acc5b3be323501cddff | d21a41b88b3a6857658a80208e904dc455b890b23aaf7d742d8a593a93afbd98 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-C-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].O-B(-O)-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8].[C:9]-[C:10](-[NH2;D1;+0:11])-[c:12]>>[C:9]-[C:10](-[N;H0;D3;+0:11](-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8])-[c:12] | 18 | [{"value": 18.0, "product": "ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)F)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 1 | HOUR | To a solution of (2S,4R)-(4-amino-2-methyl-3,4-dihydro-2H-quinolin-1-yl)-(4-fluoro-phenyl)-methanone (1.0 g, 3.5 mmol) in DMF (20 mL, dry) was added 4-chlorophenylboronic acid (1.1 g, 7.0 mmol), pyridine (850 uL, 10.5 mmol) and copper(II)acetate (1.27 g, 7.0 mmol). The heterogeneous green mixture was stirred open to ai... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine.Boronic acid | Tertiary amide | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HO-.B | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].CN(C)C=O | 60 | 1 | CCOC(C)=O.C[C@H]1C[C@@H](N)c2ccccc2N1C(=O)c1ccc(F)cc1.OB(O)c1ccc(Cl)cc1>C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].CN(C)C=O>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b0470e7758a04de497501c90395f8ef7 | CC(=O)Cl.C[C@H]1C[C@@H](Nc2ccc(Cl)cc2)c2ccccc2N1C(=O)c1ccc(F)cc1>>CC(=O)N(c1ccc(Cl)cc1)C1CC(C)N(C(=O)c2ccc(F)cc2)c2ccccc21 | C(C)(=O)Cl.ClC1=CC=C(C=C1)N[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)F)C.C(C)(C)N(CC)C(C)C>>ClC1=CC=C(C=C1)N(C(C)=O)C1CC(N(C2=CC=CC=C12)C(C1=CC=C(C=C1)F)=O)C | Cl[C:2]([CH3:1])=[O:3].[NH:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([F:23])[cH:24][cH:25]2)[c:26]2[cH:27][cH:28][cH:29][cH:30][c:31]21>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[CH:12]1[CH2:13]... | CC(=O)Cl.C[C@H]1C[C@@H](Nc2ccc(Cl)cc2)c2ccccc2N1C(=O)c1ccc(F)cc1 | CC(=O)N(c1ccc(Cl)cc1)C1CC(C)N(C(=O)c2ccc(F)cc2)c2ccccc21 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccccc1)N1CCC(Nc2ccccc2)c2ccccc21 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[c:4]:[c:5](-[NH;D2;+0:6]-[C@@H;D3;+0:7]1-[C:8]-[C:9]-[#7:10]-[c:11]:[c:12]-1:[c:13]):[c:14]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[N;H0;D3;+0:6](-[CH;D3;+0:7]1-[C:8]-[C:9]-[#7:10]-[c:11]:[c:12]-1:[c:13])-[c:5](:[c:4]):[c:14] | 72 | [{"value": 71.0, "product": "ClC1=CC=C(C=C1)N(C(C)=O)C1CC(N(C2=CC=CC=C12)C(C1=CC=C(C=C1)F)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.0, "product": "ClC1=CC=C(C=C1)N(C(C)=O)C1CC(N(C2=CC=CC=C12)C(C1=CC=C(C=C1)F)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a solution of (2S,4R)-[4-(4-chloro-phenylamino)-2-methyl-3,4-dihydro-2H-quinolin-1-yl]-(4-fluoro-phenyl)-methanone (250 mg, 0.636 mmol) in methylene chloride (5 mL) was added diisopropylethylamine (120 uL, 0.70 mmol) followed by acetyl chloride (90 uL, 1.27 mmol). The mixture was stirred at rt 4 h. The mixture was c... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HCl | C(Cl)Cl | null | 4 | CC(=O)Cl.C[C@H]1C[C@@H](Nc2ccc(Cl)cc2)c2ccccc2N1C(=O)c1ccc(F)cc1>C(Cl)Cl>CC(=O)N(c1ccc(Cl)cc1)C1CC(C)N(C(=O)c2ccc(F)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bae6b406dd2747c996157f43a18e49cc | CCC(=O)N(c1ccc(Cl)cc1)C1CC(C)N(C(=O)c2ccc(OCCCC(=O)O)cc2)c2ccccc21>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCC(=O)O)cc2)c2ccccc21 | FC1=CC=C(C(=O)Cl)C=C1.ClC1=CC=C(C=C1)N(C1CC(N(C2=CC=CC=C12)C(=O)C1=CC=C(OCCCC(=O)O)C=C1)C)C(CC)=O>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(OCCCC(=O)O)C=C1)C)C1=CC=C(C=C1)Cl | C[CH2:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[CH:12]1[CH2:13][CH:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([O:23][CH2:24][CH2:25][CH2:26][C:27](=[O:28])[OH:29])[cH:30][cH:31]2)[c:32]2[cH:33][cH:34][cH:35][cH:36][c:37]21>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]... | CCC(=O)N(c1ccc(Cl)cc1)C1CC(C)N(C(=O)c2ccc(OCCCC(=O)O)cc2)c2ccccc21 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCC(=O)O)cc2)c2ccccc21 | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C:5])-[c:6]>>[C:5]-[#7:4](-[c:6])-[C:2](-[CH3;D1;+0:1])=[O;D1;H0:3] | null | [] | null | null | null | null | (2S,4R)-4-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-butyric acid was prepared was made following general procedure C, substituting 4-methoxybenzoyl chloride for 4-fluorobenzoyl chloride. Further elaboration to the acid was done following the same procedure as describe... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | null | null | null | CCC(=O)N(c1ccc(Cl)cc1)C1CC(C)N(C(=O)c2ccc(OCCCC(=O)O)cc2)c2ccccc21>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCCCC(=O)O)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aed14fa894c74c0081111ee7611cf940 | BrCc1ccncc1.COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCc3ccncc3)cc2)c2ccccc21 | C(C)O.[H-].[Na+].ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C.BrCC1=CC=NC=C1>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OCC1=CC=NC=C1)=O)C | BrC[c:25]1[cH:26][cH:27][n:28][cH:29][cH:30]1.[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([O:23][CH3:24])[cH:31][cH:32]2)[c:33]2[cH:34][cH:35][cH:36][cH:37][c:38]21>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][... | BrCc1ccncc1.COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCc3ccncc3)cc2)c2ccccc21 | null | null | CN(C)C=O | C-C Coupling | OtherReaction | 9282e47746c7b9fca3e9abca83ead5e293ef27502e62bd81a3cdbf12d8372825 | 2c1c1647472d7e3cff37f0f3aad955b760f0ad2f8b7aa7e7825b1c0344bab3bb | O=C(c1ccc(OCc2ccncc2)cc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Br-C-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1.[CH3;D1;+0:7]-[#8:8]-[c:9]>>[c:9]-[#8:8]-[CH2;D2;+0:7]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1 | null | [] | null | null | 30 | MINUTE | The phenol was dissolved in DMF (5 mL) at room temperature. Sodium hydride (60% in oil) was added and the mixture allowed to stir 30 min. 4-Bromomethyl-pyridine was added and the reaction was allowed to stir over night. Ethanol was added and the reaction was concentrated in vacuo. The residue was partitioned between et... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether | Ether | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccccc1.c1ccncc1.c1ccc2c(c1)CCC[NH]2 | HBr | CN(C)C=O | null | 0.5 | BrCc1ccncc1.COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1>CN(C)C=O>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OCc3ccncc3)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-52c7f3ae7670408d9755bccd1a1bed37 | CCC(=O)N(c1ccccc1)C1CC(C)N(C(=O)c2ccc(O)cc2)c2ccccc21.O=C(Cl)c1ccc(F)cc1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21 | FC1=CC=C(C(=O)Cl)C=C1.C1(=CC=CC=C1)O.OC1=CC=C(C(=O)N2C(CC(C3=CC=CC=C23)N(C(CC)=O)C2=CC=CC=C2)C)C=C1>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)O)=O)C | C[CH2:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][cH:8][cH:10][cH:11]1)[CH:12]1[CH2:13][CH:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([OH:23])[cH:24][cH:25]2)[c:26]2[cH:27][cH:28][cH:29][cH:30][c:31]21.O=C(c1ccc(F)cc1)[Cl:9]>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H... | CCC(=O)N(c1ccccc1)C1CC(C)N(C(=O)c2ccc(O)cc2)c2ccccc21.O=C(Cl)c1ccc(F)cc1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21 | null | null | null | Functional Group Interconversion | OtherReaction | 91851756c52985d744aa40d2d8891afc4047f94a007ece2d25e4ce655531031f | dceb12a388b2a36b2ea72c892c8b5aa97f970ff7bfb3715e72f5be3e6fa67402 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C:5])-[c:6]1:[c:7]:[c:8]:[cH;D2;+0:9]:[c:10]:[c:11]:1.F-c1:c:c:c(-C(=O)-[Cl;H0;D1;+0:12]):c:c:1>>[C:5]-[#7:4](-[C:2](-[CH3;D1;+0:1])=[O;D1;H0:3])-[c:6]1:[c:7]:[c:8]:[c;H0;D3;+0:9](-[Cl;H0;D1;+0:12]):[c:10]:[c:11]:1 | null | [] | null | null | null | null | (2S,4R)-N-(4-Chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide was prepared was made following general procedure C, substituting 3-methoxybenzoyl chloride for 4-fluorobenzoyl chloride. Further elaboration to the phenol was done following the same procedure as described for (±)... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aromatic halide | Aromatic halide | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HF | null | null | null | CCC(=O)N(c1ccccc1)C1CC(C)N(C(=O)c2ccc(O)cc2)c2ccccc21.O=C(Cl)c1ccc(F)cc1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(O)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-258b5262bc1b4c1995a55ec514facab1 | CC(=O)c1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(C(C)(C)O)cc2)c2ccccc21 | C[Mg]Br.C(C)(=O)C1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(C)=O)C2=CC=C(C=C2)Cl)C)C=C1.C(C)(=O)C1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(C)=O)C2=CC=C(C=C2)Cl)C)C=C1.[Cl-].[NH4+]>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)C(C)(C)O)=O)C | [CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([C:23]([CH3:24])=[O:26])[cH:27][cH:28]2)[c:29]2[cH:30][cH:31][cH:32][cH:33][c:34]21>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@... | CC(=O)c1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(C(C)(C)O)cc2)c2ccccc21 | null | null | C1CCOC1 | Miscellaneous | OtherReaction | 7e61014f084ef66fe8691c8f1abaf493e11079effe9d87ae329e041d937b8b3a | 8811b4d793f7cfa9f0f1f47a008648edabb54f371f76dfa680dd5b2e1564c6c5 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | [C;D1;H3:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4](:[c:5]):[c:6]>>[C;D1;H3:1]-[C;H0;D4;+0:2](-[C;D1;H3:7])(-[OH;D1;+0:3])-[c:4](:[c:5]):[c:6] | 24 | [{"value": 24.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | (2S,4R)-N-(4-Chloro-phenyl)-N-{1-[4-(1-hydroxy-1-methyl-ethyl)-benzoyl]-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl}-acetamide was prepared from (2S,4R)-N-[1-(4-acetyl-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-(4-chloro-phenyl)-acetamide. (2S,4R)-N-[1-(4-Acetyl-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | C1CCOC1 | 0 | 2 | CC(=O)c1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1>C1CCOC1>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(C(C)(C)O)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4f0a98b5259a41a8ba3de6adcfa42b29 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(C=CC(=O)O)cc2)c2ccccc21>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(CCC(=O)O)cc2)c2ccccc21 | C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)C=CC(=O)O)C)C1=CC=C(C=C1)Cl.C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)C=CC(=O)O)C)C1=CC=C(C=C1)Cl>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)CCC(=O)O)C)C1=CC=C(C=C1)Cl | [CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([CH:23]=[CH:24][C:25](=[O:26])[OH:27])[cH:28][cH:29]2)[c:30]2[cH:31][cH:32][cH:33][cH:34][c:35]21>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:1... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(C=CC(=O)O)cc2)c2ccccc21 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(CCC(=O)O)cc2)c2ccccc21 | null | C(Cl)Cl.[Pd] | CCO | Reduction | Hydrogenation (double to single) | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | [O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[CH;D2;+0:4]=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8] | 99 | [{"value": 99.0, "product": "C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)CCC(=O)O)C)C1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | (2S,4R)-3-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenyl)-propionic acid was prepared from (2S,4R)-3-(4-{4-[acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenyl)-acrylic acid. A solution of (2S,4R)-3-(4-{4-[acetyl-(4-chloro-phenyl)-amino]-2-me... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | null | C(Cl)Cl.[Pd].CCO | null | 1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(C=CC(=O)O)cc2)c2ccccc21>C(Cl)Cl.[Pd].CCO>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(CCC(=O)O)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6265fcbda6b84c8bb5e65fe278b1e988 | COC(=O)C=Cc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(C=CC(=O)O)cc2)c2ccccc21 | FC1=CC=C(C(=O)Cl)C=C1.COC(C=CC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C1=CC=C(C=C1)Cl)C(C)=O)C)=O.[Li+].[OH-]>>C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)C=CC(=O)O)C)C1=CC=C(C=C1)Cl | C[O:27][C:25]([CH:24]=[CH:23][c:22]1[cH:21][cH:20][c:19]([C:17]([N:16]2[C@@H:14]([CH3:15])[CH2:13][C@@H:12]([N:4]([C:2]([CH3:1])=[O:3])[c:5]3[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]3)[c:35]3[c:30]2[cH:31][cH:32][cH:33][cH:34]3)=[O:18])[cH:29][cH:28]1)=[O:26]>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:... | COC(=O)C=Cc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(C=CC(=O)O)cc2)c2ccccc21 | null | null | C1CCOC1.CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]=[C:5]-[c:6]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[C:4]=[C:5]-[c:6] | 99 | [{"value": 99.0, "product": "C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)C=CC(=O)O)C)C1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.1, "product": "C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)C=CC(=O)O)C)C1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "... | null | null | null | null | (2S,4R)-3-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenyl)-acrylic acid was prepared following general procedure C, substituting 3-(4-chlorocarbonyl-phenyl)-acrylic acid methyl ester for 4-fluorobenzoyl chloride. The ester was hydrolyzed as follows. To a solution of (2S,4R)-3... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | C1CCOC1.CO | null | null | COC(=O)C=Cc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Cl)cc3)C[C@@H]2C)cc1>C1CCOC1.CO>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(C=CC(=O)O)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e71a2a67cf1645d3b3e373d992e9d838 | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3cccc(C#N)c3)C[C@@H]2C)cc1.O=C(Cl)c1ccc(F)cc1>>COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3cccc(CN)c3)C[C@@H]2C)cc1 | C(#N)C=1C=C(C=CC1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C.C(#N)C=1C=C(C=CC1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C.[BH4-].[Na+].FC1=CC=C(C(=O)Cl)C=C1>>C(#N)C=1C=C(C=CC1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C.NCC=1C=C(C=CC1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=... | C(c1[cH:57][cH:56][cH:55][c:54]([N:50]([C@H:49]2[c:48]3[c:43]([cH:44][cH:45][cH:46][cH:47]3)[N:42]([C:40]([c:39]3[cH:38][cH:37][c:36]([O:35][CH3:34])[cH:66][cH:65]3)=[O:41])[C@@H:63]([CH3:64])[CH2:62]2)[C:51]([CH3:52])=[O:53])[cH:61]1)#[N:60].O=[C:59](Cl)[c:58]1ccc(F)cc1>>[CH3:34][O:35][c:36]1[cH:37][cH:38][c:39]([C:40... | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3cccc(C#N)c3)C[C@@H]2C)cc1.O=C(Cl)c1ccc(F)cc1 | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3cccc(CN)c3)C[C@@H]2C)cc1 | null | [Co](Cl)Cl | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | b216327a21510acfef04d829ba4e934585cd7a21b66b2c5734a3dc14ea5d17bd | 30938830d4a4929ce2292ebee3b8ab24d74bb12b8b4fc72ec5814d3becc1c450 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Cl-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:c:c:c(-F):c:c:1.[C;D1;H3:3]-[C:4](=[O;D1;H0:5])-[#7:6]-[c:7]1:[c:8]:[c:9]:[cH;D2;+0:10]:c(-C#[N;H0;D1;+0:11]):[cH;D2;+0:12]:1>>[C;D1;H3:3]-[C:4](=[O;D1;H0:5])-[#7:6]-[c:7]1:[c:8]:[c:9]:[cH;D2;+0:10]:[c;H0;D3;+0:2](-[CH2;D2;+0:1]-[NH2;D1;+0:11]):[cH;D2;+0:12]:1 | 10 | [{"value": 10.0, "product": "NCC=1C=C(C=CC1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | (2S,4R)-N-(3-Aminomethyl-phenyl)-N-[1-(4-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide was prepared from (2S,4R)-N-(3-cyano-phenyl)-N-[1-(4-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide. (2S,4R)-N-(3-cyano-phenyl)-N-[1-(4-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quino... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aromatic halide.Nitrile | Primary amine | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | [Co](Cl)Cl.C(C)O | null | 0.5 | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3cccc(C#N)c3)C[C@@H]2C)cc1.O=C(Cl)c1ccc(F)cc1>[Co](Cl)Cl.C(C)O>COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3cccc(CN)c3)C[C@@H]2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e81126a2972b4b7b9b10dc3e1743a4d9 | CN(C)c1ccccc1-c1ccccc1P(C1CCCCC1)C1CCCCC1.COC(=O)COc1ccc(Br)cc1.COc1ccc(C(=O)N2c3ccccc3[C@H](N)C[C@@H]2C)cc1>>COC(=O)COc1ccc(N(C(C)=O)C2CC(C)N(C(=O)c3ccc(OC)cc3)c3ccccc32)cc1 | N[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)OC)C.COC(COC1=CC=C(C=C1)Br)=O.C1(CCCCC1)P(C1=C(C=CC=C1)C1=C(C=CC=C1)N(C)C)C1CCCCC1.C([O-])([O-])=O.[Cs+].[Cs+]>>COC(COC1=CC=C(C=C1)N(C1CC(N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C)C(C)=O)=O | CN(c1ccccc1-c1ccccc1P(C1CCCCC1)C1CCCCC1)[CH3:13].Br[c:10]1[cH:9][cH:8][c:7]([O:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[cH:37][cH:36]1.[NH2:11][C@@H:15]1[CH2:16][C@H:17]([CH3:18])[N:19]([C:20](=[O:21])[c:22]2[cH:23][cH:24][c:25]([O:26][CH3:27])[cH:28][cH:29]2)[c:30]2[cH:31][cH:32][cH:33][cH:34][c:35]21>>[CH3:1][O:2][C:3](=[... | CN(C)c1ccccc1-c1ccccc1P(C1CCCCC1)C1CCCCC1.COC(=O)COc1ccc(Br)cc1.COc1ccc(C(=O)N2c3ccccc3[C@H](N)C[C@@H]2C)cc1 | COC(=O)COc1ccc(N(C(C)=O)C2CC(C)N(C(=O)c3ccc(OC)cc3)c3ccccc32)cc1 | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | null | Acylation | OtherReaction | abd1394f6614c07911880959c73166f1d80d55d529360e81d9eb77f2886869ee | a542a495d08c4dba580c830cb345c6604739448dfac19f34f92ca5bf1236ec6f | O=C(c1ccccc1)N1CCC(Nc2ccccc2)c2ccccc21 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-N(-[CH3;D1;+0:6])-c1:c:c:c:c:c:1-c1:c:c:c:c:c:1-P(-C1-C-C-C-C-C-1)-C1-C-C-C-C-C-1.[NH2;D1;+0:7]-[C@@H;D3;+0:8]1-[C:9]-[C:10]-[#7:11]-[c:12]:[c:13]-1:[c:14]>>[CH3;D1;+0:6]-[C:15](=[O;D1;H0:16])-[N;H0;D3;+0:7](-[CH;D3;+0:8]1-[C:9]-[C:10]-[#7:11]-[c:12]:[c:13]-1:[c:14])-[c;H0;... | 368.1 | [{"value": 24.0, "product": "COC(COC1=CC=C(C=C1)N(C1CC(N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C)C(C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 368.1, "product": "COC(COC1=CC=C(C=C1)N(C1CC(N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C)C(C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 24 | HOUR | (2S,4R)-(4-Amino-2-methyl-3,4-dihydro-2H-quinolin-1-yl)-(4-methoxyphenyl)-methanone (100 mg, 0.34 mmol), methyl-2-(4-bromophenoxy)-acetate (91 mg, 0.37 mmol), Pd2(dba)3 (17 mg, 0.02 mmol), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (8 mg, 0.00002 mol) and cesium carbonate (0.163 g, 0.0005 mol) were taken in... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine.Tertiary amine | Tertiary amide | c1ccccc1.c1ccccc1.C1CCCCC1.C1CCCCC1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HBr | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | 100 | 24 | CN(C)c1ccccc1-c1ccccc1P(C1CCCCC1)C1CCCCC1.COC(=O)COc1ccc(Br)cc1.COc1ccc(C(=O)N2c3ccccc3[C@H](N)C[C@@H]2C)cc1>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]>COC(=O)COc1ccc(N(C(C)=O)C2CC(C)N(C(=O)c3ccc(OC)cc3)c3ccccc32)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d44b3b37fcab42e6b0f744bd0f650667 | COC(=O)COc1ccc(N(C(C)=O)[C@@H]2C[C@H](C)N(C(=O)c3ccc(OC)cc3)c3ccccc32)cc1>>COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(OCC(=O)O)cc3)C[C@@H]2C)cc1 | Cl.COC(COC1=CC=C(C=C1)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C)C(C)=O)=O.[OH-].[Na+]>>C(C)(=O)N(C1=CC=C(OCC(=O)O)C=C1)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C | C[O:29][C:27]([CH2:26][O:25][c:24]1[cH:23][cH:22][c:21]([N:17]([C@H:16]2[c:15]3[c:10]([cH:11][cH:12][cH:13][cH:14]3)[N:9]([C:7]([c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:36][cH:35]3)=[O:8])[C@@H:33]([CH3:34])[CH2:32]2)[C:18]([CH3:19])=[O:20])[cH:31][cH:30]1)=[O:28]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[N:9]... | COC(=O)COc1ccc(N(C(C)=O)[C@@H]2C[C@H](C)N(C(=O)c3ccc(OC)cc3)c3ccccc32)cc1 | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(OCC(=O)O)cc3)C[C@@H]2C)cc1 | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 89 | [{"value": 89.0, "product": "C(C)(=O)N(C1=CC=C(OCC(=O)O)C=C1)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.7, "product": "C(C)(=O)N(C1=CC=C(OCC(=O)O)C=C1)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C", "details": "CALCULATEDPERCENTYIELD", "is... | null | null | 18 | HOUR | (2S,4R)-(4-{Acetyl-[1-(4-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-amino}-phenoxy)-acetic acid was prepared from (2S,4R)-(4-{acetyl-[1-(4-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-amino}-phenoxy)-acetic acid methyl ester (15 mg, 0.03 mmol). The methyl ester was dissolved in methanol (1... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | CO | null | 18 | COC(=O)COc1ccc(N(C(C)=O)[C@@H]2C[C@H](C)N(C(=O)c3ccc(OC)cc3)c3ccccc32)cc1>CO>COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(OCC(=O)O)cc3)C[C@@H]2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-696adee031184bf4b13a8623daac27c8 | COC(=O)C(C)(C)c1ccc(N(C(C)=O)C2CC(C)N(C(=O)c3ccc(OC)cc3)c3ccccc32)cc1>>COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(C(C)(C)C(=O)O)cc3)C[C@@H]2C)cc1 | COC(COC1=CC=C(C=C1)Br)=O.COC(C(C)(C)C1=CC=C(C=C1)N(C1CC(N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C)C(C)=O)=O.C(C)(=O)N(C1=CC=C(OCC(=O)O)C=C1)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C>>C(C)(=O)N(C1=CC=C(C=C1)C(C(=O)O)(C)C)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C | C[O:30][C:28]([C:25]([c:24]1[cH:23][cH:22][c:21]([N:17]([CH:16]2[c:15]3[c:10]([cH:11][cH:12][cH:13][cH:14]3)[N:9]([C:7]([c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:37][cH:36]3)=[O:8])[CH:34]([CH3:35])[CH2:33]2)[C:18]([CH3:19])=[O:20])[cH:32][cH:31]1)([CH3:26])[CH3:27])=[O:29]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O... | COC(=O)C(C)(C)c1ccc(N(C(C)=O)C2CC(C)N(C(=O)c3ccc(OC)cc3)c3ccccc32)cc1 | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(C(C)(C)C(=O)O)cc3)C[C@@H]2C)cc1 | null | null | null | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | null | null | (2S,4R)-2-(4-{Acetyl-[1-(4-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-amino}-phenyl)-2-methyl-propionic acid was prepared via saponification of 2-(4-{acetyl-[1-(4-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]amino}-phenyl)-2-methyl-propionic acid methyl ester, as described in the synthesi... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | null | null | null | COC(=O)C(C)(C)c1ccc(N(C(C)=O)C2CC(C)N(C(=O)c3ccc(OC)cc3)c3ccccc32)cc1>>COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(C(C)(C)C(=O)O)cc3)C[C@@H]2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1170fa84bc654bc192bedb726b3595fa | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(CCC(=O)O)cc2)c2ccccc21.COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Br)cc3)C[C@@H]2C)cc1>>COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(CCC(=O)O)cc3)C[C@@H]2C)cc1 | ClC1=CC=C(C=C1)N(C1CC(N(C2=CC=C(C=C12)C=CC(=O)O)C(C1=CC=C(C=C1)F)=O)C)C(CC)=O.C(C)(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)CCC(=O)O)C)C1=CC=C(C=C1)Cl.BrC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C.BrC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C.C(C... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc([CH2:25][CH2:26][C:27](=[O:28])[OH:29])cc2)c2ccccc21.Br[c:24]1[cH:23][cH:22][c:21]([N:17]([C@H:16]2[c:15]3[c:10]([cH:11][cH:12][cH:13][cH:14]3)[N:9]([C:7]([c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:36][cH:35]3)=[O:8])[C@@H:33]([CH3:34])[CH2:32]2)[C:18]([CH3:19])=[O:20])[c... | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(CCC(=O)O)cc2)c2ccccc21.COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Br)cc3)C[C@@H]2C)cc1 | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(CCC(=O)O)cc3)C[C@@H]2C)cc1 | null | null | null | C-C Coupling | OtherReaction | f5c50fc2c2386f32cfff3e799dacf9c36794fb59889488b2f3e337b8f2d1b5e2 | 421f33baaa7a49fff154f8252433aba113450bc8a477e8366c5f908df290b3b2 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-C(=O)-N(-[C@H]1-C-[C@H](-C)-N(-C(=O)-c2:c:c:c(-[CH2;D2;+0:6]-[C:7]-[C:8](=[O;D1;H0:9])-[O;D1;H1:10]):c:c:2)-c2:c:c:c:c:c:2-1)-c1:c:c:c(-Cl):c:c:1>>[O;D1;H0:9]=[C:8](-[O;D1;H1:10])-[C:7]-[CH2;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | (2S,4R)-3-(4-{Acetyl-[1-(4-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-amino}-phenyl)-propionic acid was prepared from (2S,4R)-N-(4-bromo-phenyl)-N-[1-(4-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide. (2S,4R)-N-(4-Bromo-phenyl)-N-[1-(4-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Tertiary amide.Tertiary amide | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCCN2.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HCl.Br- | null | null | null | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(CCC(=O)O)cc2)c2ccccc21.COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(Br)cc3)C[C@@H]2C)cc1>>COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(CCC(=O)O)cc3)C[C@@H]2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-35c49c134b2142b981b72b68aabeb3d5 | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(CCC(=O)O)cc3)C[C@@H]2C)cc1.[NH4+]>>COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(CCC(N)=O)cc3)C[C@@H]2C)cc1 | C(C)(=O)N(C1=CC=C(C=C1)CCC(=O)O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C.C(C)(=O)N(C1=CC=C(C=C1)CCC(=O)O)C1CC(N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F.C=1C=CC2=C(C1)N=NN2O.[NH4+].[Cl-].CCN(C(C)C)C(C)C>>C(C)(=O)N(C1=CC=C(C=C1)CCC(=O)N)[C@@H]1C[C@@H](N(C2=... | O[C:27]([CH2:26][CH2:25][c:24]1[cH:23][cH:22][c:21]([N:17]([C@H:16]2[c:15]3[c:10]([cH:11][cH:12][cH:13][cH:14]3)[N:9]([C:7]([c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:36][cH:35]3)=[O:8])[C@@H:33]([CH3:34])[CH2:32]2)[C:18]([CH3:19])=[O:20])[cH:31][cH:30]1)=[O:29].[NH4+:28]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8]... | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(CCC(=O)O)cc3)C[C@@H]2C)cc1.[NH4+] | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(CCC(N)=O)cc3)C[C@@H]2C)cc1 | null | null | CN(C=O)C | Acylation | Carboxylic acid to amide conversion | 1283aef55d7ee699f097a8e5267689198c76ba671644401547f902657820236d | cb0a71c3fb37a76e96fbd81aae6f95a28398a03d1ad2c8e877085e735efb98f1 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH4+;D0:5]>>[C:4]-[C:3]-[C;H0;D3;+0:1](-[NH2;D1;+0:5])=[O;D1;H0:2] | 82 | [{"value": 82.0, "product": "C(C)(=O)N(C1=CC=C(C=C1)CCC(=O)N)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | (2S,4R)-3-(4-{Acetyl-[1-(4-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-amino}-phenyl)-propionamide was prepared from (2S,4R)-3-(4-{Acetyl-[1-(4-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-amino}-phenyl)-propionic acid. To a solution of 3-(4-{acetyl-[1-(4-methoxy-benzoyl)-2-methyl-1,2,3,4... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HO- | CN(C=O)C | null | null | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(CCC(=O)O)cc3)C[C@@H]2C)cc1.[NH4+]>CN(C=O)C>COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3ccc(CCC(N)=O)cc3)C[C@@H]2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0a31dbd4a1ce4c0f8c119144d42ce7ca | COc1cccc(C(=O)N2c3ccccc3C(O)CC2(C)C)c1.Nc1ccccc1>>COc1cccc(C(=O)N2c3ccccc3C(Nc3ccccc3)CC2(C)C)c1 | NC1=CC=CC=C1.OC1CC(N(C2=CC=CC=C12)C(=O)C1=CC(=CC=C1)OC)(C)C.I[Si](C)(C)C>>CC1(N(C2=CC=CC=C2C(C1)NC1=CC=CC=C1)C(=O)C1=CC(=CC=C1)OC)C | O[CH:17]1[c:16]2[c:11]([cH:12][cH:13][cH:14][cH:15]2)[N:10]([C:8]([c:7]2[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:29]2)=[O:9])[C:26]([CH3:27])([CH3:28])[CH2:25]1.[NH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]2[c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[C... | COc1cccc(C(=O)N2c3ccccc3C(O)CC2(C)C)c1.Nc1ccccc1 | COc1cccc(C(=O)N2c3ccccc3C(Nc3ccccc3)CC2(C)C)c1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | 965275ebca7bef7025897935012fa8cddebfeed57437f060749dfe3d0afc55f2 | c4940c2a97a655ce3fe0da51f34327276f5fad64d656fcfdbcd714b6aae5a34d | O=C(c1ccccc1)N1CCC(Nc2ccccc2)c2ccccc21 | O-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[c:5]:[c:6]-1:[c:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[c:7]:[c:6]1:[c:5]-[#7:4]-[C:3]-[C:2]-[CH;D3;+0:1]-1-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 24.3 | [{"value": 24.0, "product": "CC1(N(C2=CC=CC=C2C(C1)NC1=CC=CC=C1)C(=O)C1=CC(=CC=C1)OC)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 24.3, "product": "CC1(N(C2=CC=CC=C2C(C1)NC1=CC=CC=C1)C(=O)C1=CC(=CC=C1)OC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 6 | HOUR | To a chilled solution of (4-hydroxy-2,2-dimethyl-3,4-dihydro-2H-quinolin-1-yl)-(3-methoxy-phenyl)-methanone (500 mg, 1.6 mmol) in 10 ml dichloromethane was added slowly 0.8 ml iodotrimethylsilane (5.6 mmol) at 0° C. The resulting reaction mixture was stirred at 0° C. for 6 hours. Then the mixture was concentrated under... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Primary amine | Secondary amine | c1ccc2c(c1)CCC[NH]2 | c1ccc2c(c1)CCC[NH]2 | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HO- | ClCCl | 0 | 6 | COc1cccc(C(=O)N2c3ccccc3C(O)CC2(C)C)c1.Nc1ccccc1>ClCCl>COc1cccc(C(=O)N2c3ccccc3C(Nc3ccccc3)CC2(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-742d5628a0184da99e04baf470b05eb8 | CC(=O)Cl.COc1cccc(C(=O)N2c3ccccc3C(Nc3ccccc3)CC2(C)C)c1>>COc1cccc(C(=O)N2c3ccccc3C(N(C(C)=O)c3ccccc3)CC2(C)C)c1 | O.C(C)(=O)Cl.CC1(N(C2=CC=CC=C2C(C1)NC1=CC=CC=C1)C(=O)C1=CC(=CC=C1)OC)C.C(C)(C)N(CC)C(C)C>>COC=1C=C(C(=O)N2C(CC(C3=CC=CC=C23)N(C(C)=O)C2=CC=CC=C2)(C)C)C=CC1 | Cl[C:19]([CH3:20])=[O:21].[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]2[c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[CH:17]([NH:18][c:22]3[cH:23][cH:24][cH:25][cH:26][cH:27]3)[CH2:28][C:29]2([CH3:30])[CH3:31])[cH:32]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]2[c:11]3[cH:12][cH:13][cH:... | CC(=O)Cl.COc1cccc(C(=O)N2c3ccccc3C(Nc3ccccc3)CC2(C)C)c1 | COc1cccc(C(=O)N2c3ccccc3C(N(C(C)=O)c3ccccc3)CC2(C)C)c1 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccccc1)N1CCC(Nc2ccccc2)c2ccccc21 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:10]>>[C:4]-[C:5](-[N;H0;D3;+0:6](-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[c:7](:[c:8]):[c:9])-[c:10] | null | [] | null | null | null | null | To a solution of (2,2-dimethyl-4-phenylamino-3,4-dihydro-2H-quinolin-1-yl)-(3-methoxy-phenyl)-methanone in methylene chloride (5 mL) was added diisopropylethylamine followed by acetyl chloride. The mixture was stirred at room temperature over night. The mixture was poured into water and extracted with dichloromethane. ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HCl | C(Cl)Cl | null | null | CC(=O)Cl.COc1cccc(C(=O)N2c3ccccc3C(Nc3ccccc3)CC2(C)C)c1>C(Cl)Cl>COc1cccc(C(=O)N2c3ccccc3C(N(C(C)=O)c3ccccc3)CC2(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2d590b77661e4103beba86070db7f71d | CC=O.COc1ccc(C(=O)N2c3ccccc3[C@H](N)C[C@@H]2C)cc1.O=C(Cl)c1ccc(Cl)cc1>>CCN(C(=O)c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OC)cc2)c2ccccc21 | N[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)OC)C.C(C)=O.C(C)(C)N(C(C)C)CC.ClC1=CC=C(C(=O)Cl)C=C1.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>ClC1=CC=C(C(=O)N([C@@H]2C[C@@H](N(C3=CC=CC=C23)C(C2=CC=C(C=C2)OC)=O)C)CC)C=C1 | O=[CH:2][CH3:1].[NH2:3][C@@H:13]1[CH2:14][C@H:15]([CH3:16])[N:17]([C:18](=[O:19])[c:20]2[cH:21][cH:22][c:23]([O:24][CH3:25])[cH:26][cH:27]2)[c:28]2[cH:29][cH:30][cH:31][cH:32][c:33]21.Cl[C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1>>[CH3:1][CH2:2][N:3]([C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11]... | CC=O.COc1ccc(C(=O)N2c3ccccc3[C@H](N)C[C@@H]2C)cc1.O=C(Cl)c1ccc(Cl)cc1 | CCN(C(=O)c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OC)cc2)c2ccccc21 | null | null | ClCCl | Acylation | OtherReaction | 5a782b9f09c0c68997bbc9f3e2598567a6cca607f878381642f196bf4e3a3b46 | 08f3c3a23435387659fcbdc4547b30dce7a692aa89292d226cb9f3beec91047a | O=C(N[C@@H]1CCN(C(=O)c2ccccc2)c2ccccc21)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].O=[CH;D2;+0:6]-[C;D1;H3:7].[C:8]-[C:9](-[NH2;D1;+0:10])-[c:11]>>[C:8]-[C:9](-[N;H0;D3;+0:10](-[CH2;D2;+0:6]-[C;D1;H3:7])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[c:11] | 25.4 | [{"value": 24.0, "product": "ClC1=CC=C(C(=O)N([C@@H]2C[C@@H](N(C3=CC=CC=C23)C(C2=CC=C(C=C2)OC)=O)C)CC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 25.4, "product": "ClC1=CC=C(C(=O)N([C@@H]2C[C@@H](N(C3=CC=CC=C23)C(C2=CC=C(C=C2)OC)=O)C)CC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": fal... | null | null | 30 | MINUTE | (2S,4R)-4-Chloro-N-ethyl-N-[1-(4-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-benzamide was synthesized as described in general procedure C, except following benzyl carbamate removal the amine was modified in the following manner. To a solution of (2S,4R)-(4-amino-2-methyl-3,4-dihydro-2H-quinolin-1-yl)-(... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Primary amine | Tertiary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HCl | ClCCl | null | 0.5 | CC=O.COc1ccc(C(=O)N2c3ccccc3[C@H](N)C[C@@H]2C)cc1.O=C(Cl)c1ccc(Cl)cc1>ClCCl>CCN(C(=O)c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(OC)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5eb6560d5d354efb8accb8043354880f | CC(=O)Cl.COc1ccc(C(=O)N2CCC(Nc3ccccc3)c3ccccc32)cc1>>COc1cccc(C(=O)N2CCC(N(C(C)=O)c3ccccc3)c3ccccc32)c1 | O.C(C)(=O)Cl.C1(=CC=CC=C1)NC1CCN(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)OC.C(C)(C)N(CC)C(C)C>>COC=1C=C(C(=O)N2CCC(C3=CC=CC=C23)N(C(C)=O)C2=CC=CC=C2)C=CC1 | Cl[C:15]([CH3:16])=[O:17].[CH3:1][O:2][c:3]1[cH:4][cH:30][c:7]([C:8](=[O:9])[N:10]2[CH2:11][CH2:12][CH:13]([NH:14][c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[c:24]3[cH:25][cH:26][cH:27][cH:28][c:29]32)[cH:6][cH:5]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]2[CH2:11][CH2:12][CH:13]([N:14]([C:15]([CH... | CC(=O)Cl.COc1ccc(C(=O)N2CCC(Nc3ccccc3)c3ccccc32)cc1 | COc1cccc(C(=O)N2CCC(N(C(C)=O)c3ccccc3)c3ccccc32)c1 | null | null | C(Cl)Cl | Acylation | OtherReaction | 5e65d40c7d6c6b6e2f59d40eb17a883d54c27c2d7477ec806a56130f69d6b17e | 3db22b1160729ed8a5947d95ae3cc1125e44d4a7f588d068ea1e59774dc755bf | O=C(c1ccccc1)N1CCC(Nc2ccccc2)c2ccccc21 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C;D1;H3:4]-[#8:5]-[c;H0;D3;+0:6]1:[cH;D2;+0:7]:[cH;D2;+0:8]:[c:9](-[C:10](=[O;D1;H0:11])-[#7:12]2-[C:13]-[C:14]-[C:15](-[NH;D2;+0:16]-[c:17](:[c:18]):[c:19])-[c:20]:[c:21]-2):[c:22]:[cH;D2;+0:23]:1>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[N;H0;D3;+0:16](-[C:15]1-[C:14]-[C:... | null | [] | null | null | null | null | To a solution of (4-phenylamino-3,4-dihydro-2H-quinolin-1-yl)-(4-methoxy-phenyl)-methanone in methylene chloride was added diisopropylethylamine followed by acetyl chloride. The mixture was stirred at room temperature over night. The mixture was poured into water and extracted with dichloromethane. The extracts were wa... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Secondary amine | Ether.Tertiary amide | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HCl | C(Cl)Cl | null | null | CC(=O)Cl.COc1ccc(C(=O)N2CCC(Nc3ccccc3)c3ccccc32)cc1>C(Cl)Cl>COc1cccc(C(=O)N2CCC(N(C(C)=O)c3ccccc3)c3ccccc32)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f649d38764ca405192464d9bfecda86b | C[C@@H]1CC(=O)O1.Nc1ccccc1>>C[C@@H](CC(=O)O)Nc1ccccc1 | NC1=CC=CC=C1.C1(C[C@@H](C)O1)=O.C(=O)([O-])[O-].[K+].[K+]>>C1(=CC=CC=C1)N[C@H](CC(=O)O)C | [CH3:1][C@@H:2]1[CH2:3][C:4](=[O:5])[O:6]1.[NH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[CH3:1][C@@H:2]([CH2:3][C:4](=[O:5])[OH:6])[NH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1 | C[C@@H]1CC(=O)O1.Nc1ccccc1 | C[C@@H](CC(=O)O)Nc1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 0ecd4f20532980ca9a1e759f7de022b3f8b73a123ab3bb9fa09d76ccf580e32d | 73c1447270f630809b051744bf93d0489db5238d09a5e3d5f3ef6001adc8b63b | c1ccccc1 | [C;D1;H3:1]-[C@@H;D3;+0:2]1-[C:3]-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-1.[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C;D1;H3:1]-[C@@H;D3;+0:2](-[C:3]-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | null | [] | 80.85 | CELSIUS | null | null | A jacketed 30-L 3-neck bottom-valve cylindrical reactor equipped with overhead stirrer, reflux condenser, addition funnel, and N2 inlet was flushed with N2. Water (8.7 L) was charged followed by aniline (423 L, 4.9 mol). Stirring was initiated and the internal temperature set for 80° C. After the internal temperature r... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Carboxylic acid.Secondary amine | C1COC1 | null | c1ccccc1 | null | null | 80.85 | null | C[C@@H]1CC(=O)O1.Nc1ccccc1>>C[C@@H](CC(=O)O)Nc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5ac1040694054d8ca141260d7b6e629a | CCOC(C)=O.C[C@H]1C[C@@H](N)c2ccccc2N1C(=O)c1ccc(F)cc1.OB(O)c1ccc(Cl)cc1>>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccccc21 | C(C)(=O)OCC.N[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)F)C.ClC1=CC=C(C=C1)B(O)O.N1=CC=CC=C1>>ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)F)=O)C | CCO[C:2]([CH3:1])=[O:3].[NH2:4][C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([F:23])[cH:24][cH:25]2)[c:26]2[cH:27][cH:28][cH:29][cH:30][c:31]21.OB(O)[c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1... | CCOC(C)=O.C[C@H]1C[C@@H](N)c2ccccc2N1C(=O)c1ccc(F)cc1.OB(O)c1ccc(Cl)cc1 | CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccccc21 | null | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-] | CN(C)C=O | Acylation | OtherReaction | d5b79df0bcad37b68666465f98bdbf09561dfcc3b18a2acc5b3be323501cddff | d21a41b88b3a6857658a80208e904dc455b890b23aaf7d742d8a593a93afbd98 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | C-C-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].O-B(-O)-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8].[C:9]-[C:10](-[NH2;D1;+0:11])-[c:12]>>[C:9]-[C:10](-[N;H0;D3;+0:11](-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8])-[c:12] | 18 | [{"value": 18.0, "product": "ClC1=CC=C(C=C1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)F)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 1 | HOUR | To a solution of (2S,4R)-(4-amino-2-methyl-3,4-dihydro-2H-quinolin-1-yl)-(4-fluoro-phenyl)-methanone (1.0 g, 3.5 mmol) in DMF (20 mL, dry) was added 4-chlorophenylboronic acid (1.1 g, 7.0 mmol), pyridine (850 uL, 10.5 mmol) and copper(II)acetate (1.27 g, 7.0 mmol). The heterogeneous green mixture was stirred open to ai... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine.Boronic acid | Tertiary amide | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HO-.B | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].CN(C)C=O | 60 | 1 | CCOC(C)=O.C[C@H]1C[C@@H](N)c2ccccc2N1C(=O)c1ccc(F)cc1.OB(O)c1ccc(Cl)cc1>C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].CN(C)C=O>CC(=O)N(c1ccc(Cl)cc1)[C@@H]1C[C@H](C)N(C(=O)c2ccc(F)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7d5cd33344af40e2a4eb5b7e6e8f6f65 | CC(=O)Cl.C[C@H]1C[C@@H](Nc2ccc(Cl)cc2)c2ccccc2N1C(=O)c1ccc(F)cc1>>CC(=O)N(c1ccc(Cl)cc1)C1CC(C)N(C(=O)c2ccc(F)cc2)c2ccccc21 | ClC1=CC=C(C=C1)N[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(=O)C1=CC=C(C=C1)F)C.C(C)(C)N(CC)C(C)C.C(C)(=O)Cl>>ClC1=CC=C(C=C1)N(C(C)=O)C1CC(N(C2=CC=CC=C12)C(C1=CC=C(C=C1)F)=O)C | Cl[C:2]([CH3:1])=[O:3].[NH:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@H:14]([CH3:15])[N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([F:23])[cH:24][cH:25]2)[c:26]2[cH:27][cH:28][cH:29][cH:30][c:31]21>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[CH:12]1[CH2:13]... | CC(=O)Cl.C[C@H]1C[C@@H](Nc2ccc(Cl)cc2)c2ccccc2N1C(=O)c1ccc(F)cc1 | CC(=O)N(c1ccc(Cl)cc1)C1CC(C)N(C(=O)c2ccc(F)cc2)c2ccccc21 | null | null | null | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccccc1)N1CCC(Nc2ccccc2)c2ccccc21 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[c:4]:[c:5](-[NH;D2;+0:6]-[C@@H;D3;+0:7]1-[C:8]-[C:9]-[#7:10]-[c:11]:[c:12]-1:[c:13]):[c:14]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[N;H0;D3;+0:6](-[CH;D3;+0:7]1-[C:8]-[C:9]-[#7:10]-[c:11]:[c:12]-1:[c:13])-[c:5](:[c:4]):[c:14] | 71 | [{"value": 71.0, "product": "ClC1=CC=C(C=C1)N(C(C)=O)C1CC(N(C2=CC=CC=C12)C(C1=CC=C(C=C1)F)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a solution of (2S,4R)-[4-(4-chloro-phenylamino)-2-methyl-3,4-dihydro-2H-quinolin-1-yl]-(4-fluoro-phenyl)-methanone (250 mg, 0.636 mmol) in acetyl chloride (5 mL) was added diisopropylethylamine (120 uL, 0.70 mmol). The mixture was stirred at rt 4 h. The mixture was concentrated under reduced pressure, dissolved in e... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HCl | null | null | 4 | CC(=O)Cl.C[C@H]1C[C@@H](Nc2ccc(Cl)cc2)c2ccccc2N1C(=O)c1ccc(F)cc1>>CC(=O)N(c1ccc(Cl)cc1)C1CC(C)N(C(=O)c2ccc(F)cc2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9b1f9a27aafd474ebbeca7ef6221b5ab | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3cccc(C#N)c3)C[C@@H]2C)cc1>>COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3cccc(CN)c3)C[C@@H]2C)cc1 | C(#N)C=1C=C(C=CC1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C.[BH4-].[Na+]>>NCC=1C=C(C=CC1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[N:9]2[c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[C@H:16]([N:17]([C:18]([CH3:19])=[O:20])[c:21]3[cH:22][cH:23][cH:24][c:25]([C:26]#[N:27])[cH:28]3)[CH2:29][C@@H:30]2[CH3:31])[cH:32][cH:33]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[N:9]2[c:10]3[cH:11][cH:12][cH:1... | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3cccc(C#N)c3)C[C@@H]2C)cc1 | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3cccc(CN)c3)C[C@@H]2C)cc1 | null | [Co](Cl)Cl | null | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[NH2;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | N-(3-cyanophenyl)-N-[(2S,4R)-1-(4-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]acetamide was further treated with cobalt(II)chloride and sodium borohydride (1 eq, 3 eq) to afford N-[3-(aminomethyl)phenyl]-N-[(2S,4R)-1-(4-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]acetamide.
Conditions: See rea... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | null | [Co](Cl)Cl | null | null | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3cccc(C#N)c3)C[C@@H]2C)cc1>[Co](Cl)Cl>COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3cccc(CN)c3)C[C@@H]2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-90dfa87f2f53498d924aed3d71d1ebad | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3cccc(CN)c3)C[C@@H]2C)cc1.O=C(O)CO>>COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3cccc(CNC(=O)CO)c3)C[C@@H]2C)cc1 | C=1C=CC2=C(C1)N=NN2O.NCC=1C=C(C=CC1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C.C(CO)(=O)O.CCN=C=NCCCN(C)C>>C(CO)(=O)NCC=1C=C(C=CC1)N(C(C)=O)[C@@H]1C[C@@H](N(C2=CC=CC=C12)C(C1=CC=C(C=C1)OC)=O)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[N:9]2[c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[C@H:16]([N:17]([C:18]([CH3:19])=[O:20])[c:21]3[cH:22][cH:23][cH:24][c:25]([CH2:26][NH2:27])[cH:32]3)[CH2:33][C@@H:34]2[CH3:35])[cH:36][cH:37]1.O=[C:28]([OH:29])[CH2:30][OH:31]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O... | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3cccc(CN)c3)C[C@@H]2C)cc1.O=C(O)CO | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3cccc(CNC(=O)CO)c3)C[C@@H]2C)cc1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(c1ccccc1)N1CC[C@@H](Nc2ccccc2)c2ccccc21 | O=[C;H0;D3;+0:1](-[OH;D1;+0:2])-[C:3]-[O;D1;H1:4].[NH2;D1;+0:5]-[C:6]-[c:7]>>[O;D1;H1:4]-[C:3]-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[NH;D2;+0:5]-[C:6]-[c:7] | null | [] | null | null | null | null | N-[3-(aminomethyl)phenyl]-N-[(2S,4R)-1-(4-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]acetamide was then further coupled with glycolic acid using coupling reagent such as EDCI with HOBt to afford N-{3-[(glycoloylamino)methyl]phenyl}-N-[(2S,4R)-1-(4-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]a... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HO- | null | null | null | COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3cccc(CN)c3)C[C@@H]2C)cc1.O=C(O)CO>>COc1ccc(C(=O)N2c3ccccc3[C@H](N(C(C)=O)c3cccc(CNC(=O)CO)c3)C[C@@H]2C)cc1 |
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