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-03ba810b7f464a06b5d8787af2e8b64e | ord-aff4bb6560f44a6c9e3a0009d8d22301 | Nc1ccc(Br)cn1.O=C(Cl)c1ccccc1[N+](=O)[O-]>>O=C(Nc1ccc(Br)cn1)c1ccccc1[N+](=O)[O-] | [N+](=O)([O-])C1=C(C(=O)Cl)C=CC=C1.NC1=NC=C(C=C1)Br.N1=CC=CC=C1>>BrC=1C=CC(=NC1)NC(=O)C1=C(C=CC=C1)[N+](=O)[O-] | [NH2:3][c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][n:10]1.Cl[C:2](=[O:1])[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[N+:17](=[O:18])[O-:19]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][n:10]1)[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[N+:17](=[O:18])[O-:19] | Nc1ccc(Br)cn1.O=C(Cl)c1ccccc1[N+](=O)[O-] | O=C(Nc1ccc(Br)cn1)c1ccccc1[N+](=O)[O-] | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccccn1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10])-[c:3](:[c:4]):[c:5] | 77.9 | [{"value": 77.0, "product": "BrC=1C=CC(=NC1)NC(=O)C1=C(C=CC=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.9, "product": "BrC=1C=CC(=NC1)NC(=O)C1=C(C=CC=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-nitrobenzoyl chloride (3.70 g, 20 mmol, 1.0 equiv), 2-amino-5-bromopyridine (3.50 g, 1.0 equiv), pyridine (10 mL) in 25 mL of methylene chloride was stirred overnight. The volatile was evaporated, flash chromatography on silica gel gave N-(5-bromo-2-pyridinyl)-(2-nitro)phenylcarboxamide (5.02 g, 77%). M... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccccc1 | HCl | C(Cl)Cl | null | null | Nc1ccc(Br)cn1.O=C(Cl)c1ccccc1[N+](=O)[O-]>C(Cl)Cl>O=C(Nc1ccc(Br)cn1)c1ccccc1[N+](=O)[O-] |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-d06354339c1c4248aa2e70c96f4c2652 | CC1=CC(=O)OC1=O.Nc1ccc(Br)cn1>>CC1=CC(=O)N(c2ccc(Br)cn2)C1=O | C1(\C(\C)=C/C(=O)O1)=O.NC1=NC=C(C=C1)Br>>BrC=1C=CC(=NC1)N1C(C(=CC1=O)C)=O | O1[C:4](=[O:5])[CH:3]=[C:2]([CH3:1])[C:14]1=[O:15].[NH2:6][c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][n:13]1>>[CH3:1][C:2]1=[CH:3][C:4](=[O:5])[N:6]([c:7]2[cH:8][cH:9][c:10]([Br:11])[cH:12][n:13]2)[C:14]1=[O:15] | CC1=CC(=O)OC1=O.Nc1ccc(Br)cn1 | CC1=CC(=O)N(c2ccc(Br)cn2)C1=O | null | null | C1(=CC=CC=C1)C | Acylation | OtherReaction | cab1acd179957d4f5c27ba23f314ee257f7d508deff2838c7964b1019063e651 | 2a4a20e639c386292668b0b265a8e1b50d707d5f0576437dc5ade3e7fd444d29 | O=C1C=CC(=O)N1c1ccccn1 | [C;D1;H3:1]-[C:2]1=[C:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-O-[C;H0;D3;+0:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[#7;a:11]:[c:12]>>[C;D1;H3:1]-[C:2]1=[C:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[N;H0;D3;+0:8](-[c:9](:[c:10]):[#7;a:11]:[c:12])-[C;H0;D3;+0:6]-1=[O;D1;H0:7] | 71 | [{"value": 71.0, "product": "BrC=1C=CC(=NC1)N1C(C(=CC1=O)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.8, "product": "BrC=1C=CC(=NC1)N1C(C(=CC1=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of citraconic anhydride (1.00 mL, 11.1 mmol) and 2-amino-5-bromopyridine (1.93 g, 11.2 mmol) in toluene (60 mL) was heated to reflux overnight. The solution was cooled down, filtered. The filtrate was concentrated in vacuo to give a solid (2.10 g, yield: 71%). MS 267 and 269 (M+H).
Conditions: See reaction.no... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Substituted dicarboximide | C1=CCOC1 | C1=CC[NH]C1 | C1=CC[NH]C1.c1ccncc1 | HO- | C1(=CC=CC=C1)C | null | null | CC1=CC(=O)OC1=O.Nc1ccc(Br)cn1>C1(=CC=CC=C1)C>CC1=CC(=O)N(c2ccc(Br)cn2)C1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-a9b6035cb27d4c51a725621d2aa97cec | Nc1ccc(Cl)cn1.O=c1[nH]c2ccc(Cl)cc2c(=O)o1>>Nc1ccc(Cl)cc1C(=O)Nc1ccc(Cl)cn1 | ClC1=CC=C2C(C(=O)OC(N2)=O)=C1.NC1=NC=C(C=C1)Cl.C[Si](C)(C)[N-][Si](C)(C)C.[K+].C1(=CC=CC=C1)C>>NC1=C(C=C(C=C1)Cl)C(=O)NC1=NC=C(C=C1)Cl | [NH2:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][n:18]1.O=c1o[c:9](=[O:10])[c:8]2[c:2]([nH:1]1)[cH:3][cH:4][c:5]([Cl:6])[cH:7]2>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([Cl:6])[cH:7][c:8]1[C:9](=[O:10])[NH:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][n:18]1 | Nc1ccc(Cl)cn1.O=c1[nH]c2ccc(Cl)cc2c(=O)o1 | Nc1ccc(Cl)cc1C(=O)Nc1ccc(Cl)cn1 | null | null | O1CCCC1 | Acylation | OtherReaction | b4c245015e48b9b60756b62e3f8985928af86452315d98417a25faace320d9ae | b609a70ccab739990a9ccc4ea2adcc77011bcd0c07154489a12420f7c0e7382e | O=C(Nc1ccccn1)c1ccccc1 | O=c1:[nH;D2;+0:1]:[c:2](:[c:3]):[c:4](:[c:5]):[c;H0;D3;+0:6](=[O;D1;H0:7]):o:1.[NH2;D1;+0:8]-[c:9](:[c:10]):[#7;a:11]:[c:12]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4](-[C;H0;D3;+0:6](=[O;D1;H0:7])-[NH;D2;+0:8]-[c:9](:[c:10]):[#7;a:11]:[c:12]):[c:5] | 100 | [{"value": 100.0, "product": "NC1=C(C=C(C=C1)Cl)C(=O)NC1=NC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.7, "product": "NC1=C(C=C(C=C1)Cl)C(=O)NC1=NC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 0.5 | HOUR | To a solution of 2-amino-5-chloropyridine (328 mg, 2.55 mmol) in tetrahydrofuran (5 ml) was 0.5M potassium bis(trimethylsilyl)amide in toluene (10 ml, 5.05 mmol) dropwise at −78° C. After stirred for additional 0.5 hr at −78° C., the mixture was added 5-chloroisatoic anhydride (0.5 g, 2.55 mmol) at −78° C. The mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary amide.Primary amine | c1ccc2ncocc2c1 | c1ccccc1 | c1ccccc1.c1ccncc1 | Other | O1CCCC1 | -78 | 0.5 | Nc1ccc(Cl)cn1.O=c1[nH]c2ccc(Cl)cc2c(=O)o1>O1CCCC1>Nc1ccc(Cl)cc1C(=O)Nc1ccc(Cl)cn1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-521deda5768143b9ba3ef322a90cc5ba | CNCCN.N#Cc1ccc(C(=O)Nc2ccc(Cl)cc2C(=O)Nc2ccc(Cl)cn2)cc1>>CN1CCN=C1c1ccc(C(=O)Nc2ccc(Cl)cc2C(=O)Nc2ccc(Cl)cn2)cc1 | CNCCN.ClC1=CC(=C(C=C1)NC(=O)C1=CC=C(C=C1)C#N)C(NC1=NC=C(C=C1)Cl)=O.S.IC>>ClC1=CC(=C(C=C1)NC(=O)C1=CC=C(C=C1)C=1N(CCN1)C)C(NC1=NC=C(C=C1)Cl)=O | N[CH2:4][CH2:3][NH:2][CH3:1].[N:5]#[C:6][c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[NH:13][c:14]2[cH:15][cH:16][c:17]([Cl:18])[cH:19][c:20]2[C:21](=[O:22])[NH:23][c:24]2[cH:25][cH:26][c:27]([Cl:28])[cH:29][n:30]2)[cH:31][cH:32]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]=[C:6]1[c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[NH:13][c:14]2... | CNCCN.N#Cc1ccc(C(=O)Nc2ccc(Cl)cc2C(=O)Nc2ccc(Cl)cn2)cc1 | CN1CCN=C1c1ccc(C(=O)Nc2ccc(Cl)cc2C(=O)Nc2ccc(Cl)cn2)cc1 | null | null | N1=CC=CC=C1.CO.C(C)(=O)O.C(C)N(CC)CC | Heteroatom Alkylation and Arylation | OtherReaction | c60ad675bbef0aae4bc6f7e7229a0d6b3b6a784179e30b9e067ffd6151067a5c | 4290e5b2bf07838a6d478b39c42778e9467fef0b3ea75c8d873e295925a35d9e | O=C(Nc1ccccc1C(=O)Nc1ccccn1)c1ccc(C2=NCCN2)cc1 | N-[CH2;D2;+0:1]-[C:2]-[NH;D2;+0:3]-[C;D1;H3:4].[N;H0;D1;+0:5]#[C;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:4]-[N;H0;D3;+0:3]1-[C:2]-[CH2;D2;+0:1]-[N;H0;D2;+0:5]=[C;H0;D3;+0:6]-1-[c:7](:[c:8]):[c:9] | null | [] | null | null | 8 | HOUR | To a solution of the compound of N-{4-chloro-2-[N-(5-chloro(2-pyridyl))carbamoyl]phenyl}(4-cyanophenyl)carboxamide (683 mg, 1.66 mmol) in anhydrous pyridine (10 ml) and triethyl amine (1 ml) was saturated with hydrogen sulfide gas at 0° C. The mixture was stirred at r.t. overnight. After the evaporated the solvent, the... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine.Secondary amine | Tertiary amine | null | C1=NCC[NH]1 | C1=NCC[NH]1.c1ccccc1.c1ccccc1.c1ccncc1 | Other | N1=CC=CC=C1.CO.C(C)(=O)O.C(C)N(CC)CC | null | 8 | CNCCN.N#Cc1ccc(C(=O)Nc2ccc(Cl)cc2C(=O)Nc2ccc(Cl)cn2)cc1>N1=CC=CC=C1.CO.C(C)(=O)O.C(C)N(CC)CC>CN1CCN=C1c1ccc(C(=O)Nc2ccc(Cl)cc2C(=O)Nc2ccc(Cl)cn2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-bd09f05c6fa3401a81f8a51176430386 | Cc1ccc([N+](=O)[O-])c(C(=O)O)c1.Nc1ccc(Cl)cn1>>Cc1ccc([N+](=O)[O-])c(C(=O)Nc2ccc(Cl)cn2)c1 | CC=1C=CC(=C(C(=O)O)C1)[N+](=O)[O-].C(C(=O)Cl)(=O)Cl.NC1=NC=C(C=C1)Cl.N1=CC=CC=C1>>ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC(=C1)C)[N+](=O)[O-] | O[C:10]([c:9]1[c:5]([N+:6](=[O:7])[O-:8])[cH:4][cH:3][c:2]([CH3:1])[cH:20]1)=[O:11].[NH2:12][c:13]1[cH:14][cH:15][c:16]([Cl:17])[cH:18][n:19]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([N+:6](=[O:7])[O-:8])[c:9]([C:10](=[O:11])[NH:12][c:13]2[cH:14][cH:15][c:16]([Cl:17])[cH:18][n:19]2)[cH:20]1 | Cc1ccc([N+](=O)[O-])c(C(=O)O)c1.Nc1ccc(Cl)cn1 | Cc1ccc([N+](=O)[O-])c(C(=O)Nc2ccc(Cl)cn2)c1 | null | CN(C=O)C | ClCCl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccn1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10])-[c:3](:[c:4]):[c:5] | 92 | [{"value": 92.0, "product": "ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC(=C1)C)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.9, "product": "ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC(=C1)C)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 5-methyl-2-nitrobenzoic acid (1 g, 5.52 mmol) in dichloromethane (5 ml) was added oxalyl chloride (0.964 ml, 11.04 mmol) and a few drops of dimethylformamide. The mixture was stirred at r.t. for 2 hrs. After the evaporation of the solvent, the residue was dissolved in dichloromethane (5 ml). 2-amino-5-... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccncc1 | HO- | CN(C=O)C.ClCCl | null | 2 | Cc1ccc([N+](=O)[O-])c(C(=O)O)c1.Nc1ccc(Cl)cn1>CN(C=O)C.ClCCl>Cc1ccc([N+](=O)[O-])c(C(=O)Nc2ccc(Cl)cn2)c1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-24b595b9283a44c19b23094563f6a21c | Cc1ccc([N+](=O)[O-])c(C(=O)Nc2ccc(Cl)cn2)c1>>Nc1ccccc1C(=O)Nc1ccccn1.[Cl-] | ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC(=C1)C)[N+](=O)[O-].[H][H]>>NC1=C(C=CC=C1)C(=O)NC1=NC=CC=C1.[Cl-] | C[c:5]1[cH:4][cH:3][c:2]([N+:1](=O)[O-])[c:7]([C:8](=[O:9])[NH:10][c:11]2[cH:12][cH:13][c:14]([Cl:17])[cH:15][n:16]2)[cH:6]1>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[NH:10][c:11]1[cH:12][cH:13][cH:14][cH:15][n:16]1.[Cl-:17] | Cc1ccc([N+](=O)[O-])c(C(=O)Nc2ccc(Cl)cn2)c1 | Nc1ccccc1C(=O)Nc1ccccn1.[Cl-] | null | [Pt] | CO | Functional Group Interconversion | OtherReaction | 7335ad64e689ca4e08d92da67da5a4ba3d7b1ae27a9bb5d9a29f9de23a6b4f9a | f3a5ba2ad2c4d7897d16c1f6f55c603d6dd39035ce4ed56632c5b924cbe6ba83 | O=C(Nc1ccccn1)c1ccccc1 | C-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](-[N+;H0;D3:5](=O)-[O-]):[c:6](-[C:7](=[O;D1;H0:8])-[#7:9]-[c:10]2:[#7;a:11]:[c:12]:[c;H0;D3;+0:13](-[Cl;H0;D1;+0:14]):[c:15]:[c:16]:2):[c:17]:1>>[Cl-;H0;D0:14].[NH2;D1;+0:5]-[c:4]1:[c:3]:[c:2]:[cH;D2;+0:1]:[c:17]:[c:6]:1-[C:7](=[O;D1;H0:8])-[#7:9]-[c:10]1:[#7;a:11]:[c:12]:[cH;D2;+0:1... | null | [] | null | null | null | null | To a solution of the compound of N-(5-chloro(2-pyridyl))(5-methyl-2-nitrophenyl)carboxamide (1.48 g, 5.1 mmol) in methanol (10 ml) was added 5% Pt/C (1.48 g, 0.19 mmol). The mixture was applied hydrogen balloon at r.t. for 2 hrs. After the filtration by Celite, the filtrate was concentrated to give (2-aminophenyl)-N-(2... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Nitro group | Primary amine | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | Other | [Pt].CO | null | null | Cc1ccc([N+](=O)[O-])c(C(=O)Nc2ccc(Cl)cn2)c1>[Pt].CO>Nc1ccccc1C(=O)Nc1ccccn1.[Cl-] |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-fc958fa311974f6596f2ee991a7694ea | CNCCN.Cc1ccc(NC(=O)c2ccc(C#N)cc2)c(C(=O)Nc2ccc(Cl)cn2)c1>>Cc1ccc(NC(=O)c2ccc(C3=NCCN3C)cc2)c(C(=O)Nc2ccc(Cl)cn2)c1 | ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC(=C1)C)NC(=O)C1=CC=C(C=C1)C#N.Cl.CNCCN>>ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC(=C1)C)NC(=O)C1=CC=C(C=C1)C=1N(CCN1)C | [NH2:14][CH2:15][CH2:16][NH:17][CH3:18].N#[C:13][c:12]1[cH:11][cH:10][c:9]([C:7]([NH:6][c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:32][c:21]2[C:22](=[O:23])[NH:24][c:25]2[cH:26][cH:27][c:28]([Cl:29])[cH:30][n:31]2)=[O:8])[cH:20][cH:19]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12]([C:13]3=[N:14... | CNCCN.Cc1ccc(NC(=O)c2ccc(C#N)cc2)c(C(=O)Nc2ccc(Cl)cn2)c1 | Cc1ccc(NC(=O)c2ccc(C3=NCCN3C)cc2)c(C(=O)Nc2ccc(Cl)cn2)c1 | null | null | CO.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | c60ad675bbef0aae4bc6f7e7229a0d6b3b6a784179e30b9e067ffd6151067a5c | 4290e5b2bf07838a6d478b39c42778e9467fef0b3ea75c8d873e295925a35d9e | O=C(Nc1ccccc1C(=O)Nc1ccccn1)c1ccc(C2=NCCN2)cc1 | N#[C;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C:7]-[C:8]-[NH2;D1;+0:9]>>[C;D1;H3:5]-[N;H0;D3;+0:6]1-[C:7]-[C:8]-[N;H0;D2;+0:9]=[C;H0;D3;+0:1]-1-[c:2](:[c:3]):[c:4] | null | [] | null | null | 8 | HOUR | To a lotion of the compound of N-{2-[N-(5-chloro(2-pyridyl))carbamoyl]-4-methylphenyl}(4-cyanophenyl)carboxamide (830 mg, 2.1 mmol) in anhydrous methanol (5 ml) and ethyl acetate (10 ml) was saturated with hydrogen chloride gas at 0° C. The mixture was stirred at r.t. overnight. After the evaporated the solvent, the re... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine.Secondary amine | Tertiary amine | null | C1=NCC[NH]1 | c1ccccc1.c1ccccc1.C1=NCC[NH]1.c1ccncc1 | Other | CO.C(C)(=O)OCC | null | 8 | CNCCN.Cc1ccc(NC(=O)c2ccc(C#N)cc2)c(C(=O)Nc2ccc(Cl)cn2)c1>CO.C(C)(=O)OCC>Cc1ccc(NC(=O)c2ccc(C3=NCCN3C)cc2)c(C(=O)Nc2ccc(Cl)cn2)c1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-a210a4371d564766a8f0071baf727a04 | COc1cc(C(=O)O)c([N+](=O)[O-])c(OC)c1OC.Nc1ccc(Br)cn1>>COc1cc(C(=O)Nc2ccc(Br)cn2)c([N+](=O)[O-])c(OC)c1OC | COC=1C(=C(C(=O)O)C=C(C1OC)OC)[N+](=O)[O-].C(C(=O)Cl)(=O)Cl.NC1=NC=C(C=C1)Br.N1=CC=CC=C1>>BrC=1C=CC(=NC1)NC(=O)C1=C(C(=C(C(=C1)OC)OC)OC)[N+](=O)[O-] | O[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:23]([O:24][CH3:25])[c:20]([O:21][CH3:22])[c:16]1[N+:17](=[O:18])[O-:19])=[O:7].[NH2:8][c:9]1[cH:10][cH:11][c:12]([Br:13])[cH:14][n:15]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][c:12]([Br:13])[cH:14][n:15]2)[c:16]([N+:17](=[O:18])[O-:19])[c:20]([O:21... | COc1cc(C(=O)O)c([N+](=O)[O-])c(OC)c1OC.Nc1ccc(Br)cn1 | COc1cc(C(=O)Nc2ccc(Br)cn2)c([N+](=O)[O-])c(OC)c1OC | null | CN(C=O)C | ClCCl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccn1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 2 | HOUR | To a solution of 3,4,5-trimethoxy-2-nitrobenzoic acid (0.5 g, 1.95 mmol) in dichloromethane (5 ml) was added oxalyl chloride (0.34 ml, 3.9 mmol) and a few drops of dimethylformamide. The mixture was stirred at r.t. for 2 hrs. After the evaporation of the solvent, the residue was dissolved in dichloromethane (5 ml). 2-a... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccncc1 | HO- | CN(C=O)C.ClCCl | null | 2 | COc1cc(C(=O)O)c([N+](=O)[O-])c(OC)c1OC.Nc1ccc(Br)cn1>CN(C=O)C.ClCCl>COc1cc(C(=O)Nc2ccc(Br)cn2)c([N+](=O)[O-])c(OC)c1OC |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-f6ff2f43c9804f5a977194ab3f2eb2d2 | COc1cc(C(=O)Nc2ccc(Br)cn2)c([N+](=O)[O-])c(OC)c1OC>>COc1cc(C(=O)Nc2ccc(Br)cn2)c(N)c(OC)c1OC | BrC=1C=CC(=NC1)NC(=O)C1=C(C(=C(C(=C1)OC)OC)OC)[N+](=O)[O-]>>NC1=C(C=C(C(=C1OC)OC)OC)C(=O)NC1=NC=C(C=C1)Br | O=[N+:17]([O-])[c:16]1[c:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][c:12]([Br:13])[cH:14][n:15]2)[cH:4][c:3]([O:2][CH3:1])[c:21]([O:22][CH3:23])[c:18]1[O:19][CH3:20]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][c:12]([Br:13])[cH:14][n:15]2)[c:16]([NH2:17])[c:18]([O:19][CH3:20])[c:21]1[O:22][CH... | COc1cc(C(=O)Nc2ccc(Br)cn2)c([N+](=O)[O-])c(OC)c1OC | COc1cc(C(=O)Nc2ccc(Br)cn2)c(N)c(OC)c1OC | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | C(C)(=O)OCC | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(Nc1ccccn1)c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]-[C:5](-[#7:6])=[O;D1;H0:7]>>[#7:6]-[C:5](=[O;D1;H0:7])-[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | 77.7 | [{"value": 77.0, "product": "NC1=C(C=C(C(=C1OC)OC)OC)C(=O)NC1=NC=C(C=C1)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.7, "product": "NC1=C(C=C(C(=C1OC)OC)OC)C(=O)NC1=NC=C(C=C1)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of the compound of N-(5-bromo(2-pyridyl))(3,4,5-trimethoxy-2-nitrophenyl)carboxamide (790 mg, 1.92 mmol) in ethyl acetate (5 ml) was added tin chloride (II) hydrate (1.73 g, 7.67 mmol). The mixture was stirred under reflux condition for 2 hrs. After filtered by Celite, the filtrate was added 1N sodium hyd... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccncc1 | Other | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.C(C)(=O)OCC | null | null | COc1cc(C(=O)Nc2ccc(Br)cn2)c([N+](=O)[O-])c(OC)c1OC>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.C(C)(=O)OCC>COc1cc(C(=O)Nc2ccc(Br)cn2)c(N)c(OC)c1OC |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-958271ca3f154d7696885840af850fec | CNCCN.COc1cc(C(=O)Nc2ccc(Br)cn2)c(NC(=O)c2ccc(C#N)cc2)c(OC)c1OC>>COc1cc(C(=O)Nc2ccc(Br)cn2)c(NC(=O)c2ccc(C3=NCCN3C)cc2)c(OC)c1OC | BrC=1C=CC(=NC1)NC(=O)C1=CC(=C(C(=C1NC(=O)C1=CC=C(C=C1)C#N)OC)OC)OC.Cl.CNCCN>>BrC=1C=CC(=NC1)NC(=O)C1=CC(=C(C(=C1NC(=O)C1=CC=C(C=C1)C=1N(CCN1)C)OC)OC)OC | [NH2:25][CH2:26][CH2:27][NH:28][CH3:29].N#[C:24][c:23]1[cH:22][cH:21][c:20]([C:18]([NH:17][c:16]2[c:5]([C:6](=[O:7])[NH:8][c:9]3[cH:10][cH:11][c:12]([Br:13])[cH:14][n:15]3)[cH:4][c:3]([O:2][CH3:1])[c:35]([O:36][CH3:37])[c:32]2[O:33][CH3:34])=[O:19])[cH:31][cH:30]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[NH:8][c:9]... | CNCCN.COc1cc(C(=O)Nc2ccc(Br)cn2)c(NC(=O)c2ccc(C#N)cc2)c(OC)c1OC | COc1cc(C(=O)Nc2ccc(Br)cn2)c(NC(=O)c2ccc(C3=NCCN3C)cc2)c(OC)c1OC | null | null | CO.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | c60ad675bbef0aae4bc6f7e7229a0d6b3b6a784179e30b9e067ffd6151067a5c | 4290e5b2bf07838a6d478b39c42778e9467fef0b3ea75c8d873e295925a35d9e | O=C(Nc1ccccc1C(=O)Nc1ccccn1)c1ccc(C2=NCCN2)cc1 | N#[C;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C:7]-[C:8]-[NH2;D1;+0:9]>>[C;D1;H3:5]-[N;H0;D3;+0:6]1-[C:7]-[C:8]-[N;H0;D2;+0:9]=[C;H0;D3;+0:1]-1-[c:2](:[c:3]):[c:4] | 32 | [{"value": 32.0, "product": "BrC=1C=CC(=NC1)NC(=O)C1=CC(=C(C(=C1NC(=O)C1=CC=C(C=C1)C=1N(CCN1)C)OC)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 31.7, "product": "BrC=1C=CC(=NC1)NC(=O)C1=CC(=C(C(=C1NC(=O)C1=CC=C(C=C1)C=1N(CCN1)C)OC)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of the compound of N-{6-[N-(5-bromo(2-pyridyl))carbamoyl]-2,3,4-trimethoxyphenyl}(4-cyanophenyl)carboxamide (680 mg, 1.33 mmol) in anhydrous methanol (5 ml) and ethyl acetate (10 ml) was saturated with hydrogen chloride gas at 0° C. The mixture was stirred at r.t. overnight. After the evaporated the solve... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine.Secondary amine | Tertiary amine | null | C1=NCC[NH]1 | c1ccccc1.c1ccncc1.c1ccccc1.C1=NCC[NH]1 | Other | CO.C(C)(=O)OCC | null | 8 | CNCCN.COc1cc(C(=O)Nc2ccc(Br)cn2)c(NC(=O)c2ccc(C#N)cc2)c(OC)c1OC>CO.C(C)(=O)OCC>COc1cc(C(=O)Nc2ccc(Br)cn2)c(NC(=O)c2ccc(C3=NCCN3C)cc2)c(OC)c1OC |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-432e5e98f72e4755bd8a27be74a5a6c8 | CC(C)(C)NS(=O)(=O)c1ccccc1-c1ccc(C(=O)O)cc1.Nc1ccc(Cl)cc1C(=O)Nc1ccc(Cl)cn1>>CC(C)(C)NS(=O)(=O)c1ccccc1-c1ccc(C(=O)Nc2ccc(Cl)cc2C(=O)Nc2ccc(Cl)cn2)cc1 | C(C)(C)(C)NS(=O)(=O)C1=C(C=CC=C1)C1=CC=C(C(=O)O)C=C1.C(C(=O)Cl)(=O)Cl.NC1=C(C=C(C=C1)Cl)C(=O)NC1=NC=C(C=C1)Cl.N1=CC=CC=C1>>C(C)(C)(C)NS(=O)(=O)C1=C(C=CC=C1)C1=CC=C(C=C1)C(=O)NC1=C(C=C(C=C1)Cl)C(=O)NC1=NC=C(C=C1)Cl | O[C:19]([c:18]1[cH:17][cH:16][c:15](-[c:14]2[c:9]([S:6]([NH:5][C:2]([CH3:1])([CH3:3])[CH3:4])(=[O:7])=[O:8])[cH:10][cH:11][cH:12][cH:13]2)[cH:40][cH:39]1)=[O:20].[NH2:21][c:22]1[cH:23][cH:24][c:25]([Cl:26])[cH:27][c:28]1[C:29](=[O:30])[NH:31][c:32]1[cH:33][cH:34][c:35]([Cl:36])[cH:37][n:38]1>>[CH3:1][C:2]([CH3:3])([CH3... | CC(C)(C)NS(=O)(=O)c1ccccc1-c1ccc(C(=O)O)cc1.Nc1ccc(Cl)cc1C(=O)Nc1ccc(Cl)cn1 | CC(C)(C)NS(=O)(=O)c1ccccc1-c1ccc(C(=O)Nc2ccc(Cl)cc2C(=O)Nc2ccc(Cl)cn2)cc1 | null | CN(C=O)C | ClCCl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1C(=O)Nc1ccccn1)c1ccc(-c2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH2;D1;+0:11]):[c:12]>>[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]):[c:12] | null | [] | null | null | 2 | HOUR | To a solution of 4-{2-{[(tert-butyl)amino}sulfonyl}phenyl}benzoic acid (167 mg, 0.5 mmol) in dichloromethane (5 ml) was added oxalyl chloride (0.09 ml, 1 mmol) and a few drops of dimethylformamide. The mixture was stirred at r.t. for 2 hrs. After the evaporation of the solvent, the residue was dissolved in dichlorometh... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccncc1 | HO- | CN(C=O)C.ClCCl | null | 2 | CC(C)(C)NS(=O)(=O)c1ccccc1-c1ccc(C(=O)O)cc1.Nc1ccc(Cl)cc1C(=O)Nc1ccc(Cl)cn1>CN(C=O)C.ClCCl>CC(C)(C)NS(=O)(=O)c1ccccc1-c1ccc(C(=O)Nc2ccc(Cl)cc2C(=O)Nc2ccc(Cl)cn2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-51b3463d197f4d3383bc60335e37cfca | CC(C)(C)NS(=O)(=O)c1ccccc1-c1ccc(C(=O)Nc2ccc(Cl)cc2C(=O)Nc2ccc(Cl)cn2)cc1>>NS(=O)(=O)c1ccccc1-c1ccc(C(=O)Nc2ccc(Cl)cc2C(=O)Nc2ccc(Cl)cn2)cc1 | C(C)(C)(C)NS(=O)(=O)C1=C(C=CC=C1)C1=CC=C(C=C1)C(=O)NC1=C(C=C(C=C1)Cl)C(=O)NC1=NC=C(C=C1)Cl>>ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC(=C1)Cl)NC(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)S(N)(=O)=O | CC(C)(C)[NH:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1-[c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[NH:17][c:18]2[cH:19][cH:20][c:21]([Cl:22])[cH:23][c:24]2[C:25](=[O:26])[NH:27][c:28]2[cH:29][cH:30][c:31]([Cl:32])[cH:33][n:34]2)[cH:35][cH:36]1>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9... | CC(C)(C)NS(=O)(=O)c1ccccc1-c1ccc(C(=O)Nc2ccc(Cl)cc2C(=O)Nc2ccc(Cl)cn2)cc1 | NS(=O)(=O)c1ccccc1-c1ccc(C(=O)Nc2ccc(Cl)cc2C(=O)Nc2ccc(Cl)cn2)cc1 | null | null | FC(C(=O)O)(F)F | Deprotection | Tert-butyl deprotection of amine | f7e1da1b4c254f1e6d5afbf8cb56733a4fabd145b80e971e3b7e31007de9e7d6 | 278d0fb11b582c058ac903379d7fbe11ab8c395937a204965031cf0c344845a9 | O=C(Nc1ccccc1C(=O)Nc1ccccn1)c1ccc(-c2ccccc2)cc1 | C-C(-C)(-C)-[NH;D2;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5]>>[NH2;D1;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5] | 25 | [{"value": 25.0, "product": "ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC(=C1)Cl)NC(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)S(N)(=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | The mixture of the compound of (2-{[4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)phenyl]carbonylamino}-5-chlorophenyl)-N-(5-chloro(2-pyridyl))carboxamide example 12 (0.5 mmol) in trifluoroacetic acid (5 ml) was stirred at r.t. for 5 hrs. After the evaporation of solvent, the crude residue was purified by RP-HPLC to give N-... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Sulfonamide | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccncc1 | Other | FC(C(=O)O)(F)F | null | 5 | CC(C)(C)NS(=O)(=O)c1ccccc1-c1ccc(C(=O)Nc2ccc(Cl)cc2C(=O)Nc2ccc(Cl)cn2)cc1>FC(C(=O)O)(F)F>NS(=O)(=O)c1ccccc1-c1ccc(C(=O)Nc2ccc(Cl)cc2C(=O)Nc2ccc(Cl)cn2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-99c3ae0889fe4420b0409a609b3092ec | N#Cc1ccccc1-c1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1>>N=C(N)c1ccccc1-c1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1 | S.ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC=C1)NC(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)C#N.N1=CC=CC=C1.CI>>ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC=C1)NC(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)C(=N)N | [N:1]#[C:2][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1-[c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])[NH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]2[C:23](=[O:24])[NH:25][c:26]2[cH:27][cH:28][c:29]([Cl:30])[cH:31][n:32]2)[cH:33][cH:34]1>>[NH:1]=[C:2]([NH2:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1-[c:10]1[cH:11][cH:12][c:13]([C:1... | N#Cc1ccccc1-c1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1 | N=C(N)c1ccccc1-c1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1 | null | null | C(C)(=O)O.CO.CC(=O)C.CCN(CC)CC | Functional Group Addition | OtherReaction | b3aaef1538bea73aa85740ccbb089c1b6ca4b164a10fd32235acb6c78d1de6d9 | d1a81d2cc57b1a744f94f80261b8629cf532e8b73012860cc8db4db5903fee1a | O=C(Nc1ccccc1C(=O)Nc1ccccn1)c1ccc(-c2ccccc2)cc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[N;D1;H2:6]-[C;H0;D3;+0:2](=[NH;D1;+0:1])-[c:3](:[c:4]):[c:5] | 15 | [{"value": 15.0, "product": "ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC=C1)NC(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)C(=N)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | DAY | A stream of H2S (g) was bubbled through a 0° C. solution of N-{2-[N-(5-chloro(2-pyridyl))carbamoyl]phenyl}[4-(2-cyanophenyl)phenyl]carboxamide (100 mg, 0.22 mmol, 1.0 equiv.) in 9 mL pyridine and 1 mL NEt3 until saturation. The mixture was stirred at rt for 1 day and evaporated. The resulting residue was treated with M... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccncc1 | Other | C(C)(=O)O.CO.CC(=O)C.CCN(CC)CC | null | 24 | N#Cc1ccccc1-c1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1>C(C)(=O)O.CO.CC(=O)C.CCN(CC)CC>N=C(N)c1ccccc1-c1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-e9e8ade37fa045e6b205871fa78eff47 | N#Cc1ccccc1-c1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1.NO>>O=C(Nc1ccccc1C(=O)Nc1ccc(Cl)cn1)c1ccc(-c2ccccc2C=NNO)cc1 | ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC=C1)NC(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)C#N.Cl.ON.C(C)N(CC)CC>>ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC=C1)NC(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)C=NNO | [O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[C:10](=[O:11])[NH:12][c:13]1[cH:14][cH:15][c:16]([Cl:17])[cH:18][n:19]1)[c:20]1[cH:21][cH:22][c:23](-[c:24]2[cH:25][cH:26][cH:27][cH:28][c:29]2[C:30]#[N:31])[cH:34][cH:35]1.[NH2:32][OH:33]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[C:10](=[O:11])[NH:12... | N#Cc1ccccc1-c1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1.NO | O=C(Nc1ccccc1C(=O)Nc1ccc(Cl)cn1)c1ccc(-c2ccccc2C=NNO)cc1 | null | null | C(C)O | Miscellaneous | OtherReaction | 5ebc8ae9c43671ddb0100b0cbc1ec0c40d1e187e38be7171f745b68f0dc6a2a1 | 58f66636c1d89ede1b1e759542791677a2888499f20f253f7f8ee20c2e377b3e | O=C(Nc1ccccc1C(=O)Nc1ccccn1)c1ccc(-c2ccccc2)cc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[O;D1;H1:7]>>[O;D1;H1:7]-[NH;D2;+0:6]-[N;H0;D2;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5] | 27.5 | [{"value": 27.5, "product": "ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC=C1)NC(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)C=NNO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 27.4, "product": "ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC=C1)NC(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)C=NNO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | DAY | A mixture of N-{2-[N-(5-chloro(2-pyridyl))carbamoyl]phenyl}[4-(2-cyanophenyl)phenyl]carboxamide (14 mg, 0.03 mmol, 1.0 equiv.), hydroxyamine hydrochloride (6.25 mg, 0.09 mmol, 3.0 equiv.) and triethyl amine (0.03 mL, 0.3 mmol, 10.0 equiv.) in ethanol (3 mL) was stirred at rt for 6 days, concentrated and HPLC (C18 rever... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine | Hydrazone | null | null | c1ccccc1.c1ccncc1.c1ccccc1.c1ccccc1 | null | C(C)O | null | 144 | N#Cc1ccccc1-c1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1.NO>C(C)O>O=C(Nc1ccccc1C(=O)Nc1ccc(Cl)cn1)c1ccc(-c2ccccc2C=NNO)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-e07f07c233194fffb8fe4e88631f016a | N#Cc1ccccc1-c1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1>>NCc1ccccc1-c1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1 | ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC=C1)NC(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)C#N.[BH4-].[Na+]>>NCC1=C(C=CC=C1)C1=CC=C(C=C1)C(=O)NC1=C(C=CC=C1)C(NC1=NC=C(C=C1)Cl)=O | [N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1-[c:9]1[cH:10][cH:11][c:12]([C:13](=[O:14])[NH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[C:22](=[O:23])[NH:24][c:25]2[cH:26][cH:27][c:28]([Cl:29])[cH:30][n:31]2)[cH:32][cH:33]1>>[NH2:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1-[c:9]1[cH:10][cH:11][c:12]([C:13](=[O:14... | N#Cc1ccccc1-c1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1 | NCc1ccccc1-c1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1 | null | [Co](Cl)Cl | CN(C)C=O | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | O=C(Nc1ccccc1C(=O)Nc1ccccn1)c1ccc(-c2ccccc2)cc1 | [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] | 43.1 | [{"value": 43.0, "product": "NCC1=C(C=CC=C1)C1=CC=C(C=C1)C(=O)NC1=C(C=CC=C1)C(NC1=NC=C(C=C1)Cl)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.1, "product": "NCC1=C(C=CC=C1)C1=CC=C(C=C1)C(=O)NC1=C(C=CC=C1)C(NC1=NC=C(C=C1)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | A mixture of N-{2-[N-(5-chloro(2-pyridyl))carbamoyl]phenyl}[4-(2-cyanophenyl)phenyl]carboxamide (200 mg, 0.442 mmol, 1.0 equiv.), cobalt chloride (86 mg, 0.664 mmol, 1.5 equiv.) and sodium borohydride (50 mg, 1.33 mmol, 3.0 equiv.) in DMF (15 mL) was stirred at 0° C. to rt for 3 days. The reaction was quenched with ice... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccncc1 | null | [Co](Cl)Cl.CN(C)C=O | null | 72 | N#Cc1ccccc1-c1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1>[Co](Cl)Cl.CN(C)C=O>NCc1ccccc1-c1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-a33abca967ae4d04826e526108b5ff3e | N#Cc1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1>>NCc1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1 | ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC=C1)NC(=O)C1=CC=C(C=C1)C#N.[BH4-].[Na+]>>NCC1=CC=C(C=C1)C(=O)NC1=C(C=CC=C1)C(NC1=NC=C(C=C1)Cl)=O | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[C:16](=[O:17])[NH:18][c:19]2[cH:20][cH:21][c:22]([Cl:23])[cH:24][n:25]2)[cH:26][cH:27]1>>[NH2:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[C:16](=[O:17])[NH:18][c:19]2[cH:20... | N#Cc1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1 | NCc1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1 | null | [Co](Cl)Cl | CN(C)C=O | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | O=C(Nc1ccccc1C(=O)Nc1ccccn1)c1ccccc1 | [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] | 32.3 | [{"value": 30.0, "product": "NCC1=CC=C(C=C1)C(=O)NC1=C(C=CC=C1)C(NC1=NC=C(C=C1)Cl)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.3, "product": "NCC1=CC=C(C=C1)C(=O)NC1=C(C=CC=C1)C(NC1=NC=C(C=C1)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | A mixture of N-{2-[N-(5-chloro(2-pyridyl))carbamoyl]phenyl}(4-cyanophenyl)carboxamide (1 g, 2.6 mmol, 1.0 equiv.), cobalt chloride (0.5 g, 3.85 mmol, 1.5 equiv.) and sodium borohydride (0.295 g, 7.8 mmol, 3.0 equiv.) in DMF (20 mL) was stirred at 0° C. to rt for 2.5 hr. The reaction was quenched with ice cubes, diluted... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccccc1.c1ccccc1.c1ccncc1 | null | [Co](Cl)Cl.CN(C)C=O | null | 2.5 | N#Cc1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1>[Co](Cl)Cl.CN(C)C=O>NCc1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-1546da5dfd1f4983ae13230c459a50de | CSC1=NCCN1.NCc1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1>>O=C(Nc1ccccc1C(=O)Nc1ccc(Cl)cn1)c1ccc(CNC2=NCCN2)cc1 | NCC1=CC=C(C=C1)C(=O)NC1=C(C=CC=C1)C(NC1=NC=C(C=C1)Cl)=O.I.CSC=1NCCN1.C(C)N(CC)CC>>ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC=C1)NC(=O)C1=CC=C(C=C1)CNC=1NCCN1 | CS[C:26]1=[N:27][CH2:28][CH2:29][NH:30]1.[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[C:10](=[O:11])[NH:12][c:13]1[cH:14][cH:15][c:16]([Cl:17])[cH:18][n:19]1)[c:20]1[cH:21][cH:22][c:23]([CH2:24][NH2:25])[cH:31][cH:32]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[C:10](=[O:11])[NH:12][c:13]1[cH:14]... | CSC1=NCCN1.NCc1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1 | O=C(Nc1ccccc1C(=O)Nc1ccc(Cl)cn1)c1ccc(CNC2=NCCN2)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | b8b2c7cb02682d6c06684e6c7b2dfb49c6d9023dd6b43e4d41769a82c503b02f | 88e0224d19b2dce8f9987d52554afb32090d36ff7ee19e89dc5bf66d30974ec4 | O=C(Nc1ccccc1C(=O)Nc1ccccn1)c1ccc(CNC2=NCCN2)cc1 | C-S-[C;H0;D3;+0:1]1=[#7:2]-[C:3]-[C:4]-[#7:5]-1.[NH2;D1;+0:6]-[C:7]-[c:8]>>[c:8]-[C:7]-[NH;D2;+0:6]-[C;H0;D3;+0:1]1=[#7:2]-[C:3]-[C:4]-[#7:5]-1 | 15 | [{"value": 15.0, "product": "ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC=C1)NC(=O)C1=CC=C(C=C1)CNC=1NCCN1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 14.3, "product": "ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC=C1)NC(=O)C1=CC=C(C=C1)CNC=1NCCN1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of [4-(aminomethyl)phenyl]-N-{2-[N-(5-chloro(2-pyridyl))carbamoyl]phenyl}carboxamide (80 mg, 0.21 mmol), 2-methylthio-2-imidazoline hydriodide (77 mg, 0.315 mmol, 1.5 equiv.) and triethyl amine (0.5 mL) in 1 mL DMF was stirred at room temperature overnight, concentrated to dryness and HPLC (C18 reversed phase... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide | Secondary amine | C1=NCCN1 | C1=NCCN1 | c1ccccc1.c1ccncc1.c1ccccc1.C1=NCCN1 | Other | CN(C)C=O | null | 8 | CSC1=NCCN1.NCc1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1>CN(C)C=O>O=C(Nc1ccccc1C(=O)Nc1ccc(Cl)cn1)c1ccc(CNC2=NCCN2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-30a4b1acec744fe7ac7ca91be30e3f4f | CSC1=NCCN1C.NCc1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1>>CN1CCN=C1NCc1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1 | NCC1=CC=C(C=C1)C(=O)NC1=C(C=CC=C1)C(NC1=NC=C(C=C1)Cl)=O.CN1C(=NCC1)SC.CCN(CC)CC>>ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC=C1)NC(=O)C1=CC=C(C=C1)CNC=1N(CCN1)C | CS[C:6]1=[N:5][CH2:4][CH2:3][N:2]1[CH3:1].[NH2:7][CH2:8][c:9]1[cH:10][cH:11][c:12]([C:13](=[O:14])[NH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[C:22](=[O:23])[NH:24][c:25]2[cH:26][cH:27][c:28]([Cl:29])[cH:30][n:31]2)[cH:32][cH:33]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]=[C:6]1[NH:7][CH2:8][c:9]1[cH:10][cH:11][c:12]([C:1... | CSC1=NCCN1C.NCc1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1 | CN1CCN=C1NCc1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1 | null | null | N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | 3d9229dd690869c9ac61e6b6820af19abd0e765828a31068efa43748fe7d0ebd | 88e0224d19b2dce8f9987d52554afb32090d36ff7ee19e89dc5bf66d30974ec4 | O=C(Nc1ccccc1C(=O)Nc1ccccn1)c1ccc(CNC2=NCCN2)cc1 | C-S-[C;H0;D3;+0:1]1=[#7:2]-[C:3]-[C:4]-[#7:5]-1-[C;D1;H3:6].[NH2;D1;+0:7]-[C:8]-[c:9]>>[C;D1;H3:6]-[#7:5]1-[C:4]-[C:3]-[#7:2]=[C;H0;D3;+0:1]-1-[NH;D2;+0:7]-[C:8]-[c:9] | 65 | [{"value": 65.0, "product": "ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC=C1)NC(=O)C1=CC=C(C=C1)CNC=1N(CCN1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.6, "product": "ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC=C1)NC(=O)C1=CC=C(C=C1)CNC=1N(CCN1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 8 | HOUR | A mixture of [4-(aminomethyl)phenyl]-N-{2-[N-(5-chloro(2-pyridyl))carbamoyl]phenyl}carboxamide (74 mg, 0.195 mmol), 1-methyl-2-methylthio-2-imidazoline (25 mg, 0.195 mmol), NEt3 (2 mL) and pyridine (5 mL) was stirred at 80° C. overnight, concentrated and HPLC (C18 reversed phase) eluting with 0.1% TFA in H2O/CH3CN gave... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide | Secondary amine | C1=NCC[NH]1 | C1=NCC[NH]1 | C1=NCC[NH]1.c1ccccc1.c1ccccc1.c1ccncc1 | Other | N1=CC=CC=C1 | 80 | 8 | CSC1=NCCN1C.NCc1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1>N1=CC=CC=C1>CN1CCN=C1NCc1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-f5114e14d5ad490499ca327d32a64c19 | Nc1ccc(Br)cn1.O=C(O)c1cc(F)ccc1[N+](=O)[O-]>>O=C(Nc1ccc(Br)cn1)c1cc(F)ccc1[N+](=O)[O-] | FC=1C=CC(=C(C(=O)O)C1)[N+](=O)[O-].NC1=NC=C(C=C1)Br.P(=O)(Cl)(Cl)Cl>>BrC=1C=CC(=NC1)NC(=O)C1=C(C=CC(=C1)F)[N+](=O)[O-] | [NH2:3][c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][n:10]1.O[C:2](=[O:1])[c:11]1[cH:12][c:13]([F:14])[cH:15][cH:16][c:17]1[N+:18](=[O:19])[O-:20]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][n:10]1)[c:11]1[cH:12][c:13]([F:14])[cH:15][cH:16][c:17]1[N+:18](=[O:19])[O-:20] | Nc1ccc(Br)cn1.O=C(O)c1cc(F)ccc1[N+](=O)[O-] | O=C(Nc1ccc(Br)cn1)c1cc(F)ccc1[N+](=O)[O-] | null | null | N1=CC=CC=C1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccn1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10])-[c:3](:[c:4]):[c:5] | 68.1 | [{"value": 68.0, "product": "BrC=1C=CC(=NC1)NC(=O)C1=C(C=CC(=C1)F)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.1, "product": "BrC=1C=CC(=NC1)NC(=O)C1=C(C=CC(=C1)F)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 5-fluoro-2-nitrobenzoic acid (10.0 g, 54 mmol, 1.0 equiv), 2-amino-5-bromopyridine (12.2 g, 1.3 equiv), in 80 mL of pyridine was treated with phosphorous oxychloride (25.3 g, 3.0 equiv) for 30 min. The volatile was evaporated and the residue was redissolved into EtOAc., washed with 1N HCl, saturated aqueo... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccccc1 | HO- | N1=CC=CC=C1 | null | null | Nc1ccc(Br)cn1.O=C(O)c1cc(F)ccc1[N+](=O)[O-]>N1=CC=CC=C1>O=C(Nc1ccc(Br)cn1)c1cc(F)ccc1[N+](=O)[O-] |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-82bf9b1954454b0fb3915cb4422c3e72 | COc1ccc(NC(=O)c2ccc(C#N)cc2)c(C(=O)Nc2ccc(Cl)cn2)c1.NO>>COc1ccc(NC(=O)c2ccc(C(N)=NO)cc2)c(C(=O)Nc2ccc(Cl)cn2)c1 | ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC(=C1)OC)NC(=O)C1=CC=C(C=C1)C#N.Cl.ON.CCN(CC)CC>>NC(C1=CC=C(C=C1)C(=O)NC1=C(C=C(C=C1)OC)C(=O)NC1=NC=C(C=C1)Cl)=NO | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]([C:14]#[N:15])[cH:18][cH:19]2)[c:20]([C:21](=[O:22])[NH:23][c:24]2[cH:25][cH:26][c:27]([Cl:28])[cH:29][n:30]2)[cH:31]1.[NH2:16][OH:17]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]([C:14]([NH2:15])=[... | COc1ccc(NC(=O)c2ccc(C#N)cc2)c(C(=O)Nc2ccc(Cl)cn2)c1.NO | COc1ccc(NC(=O)c2ccc(C(N)=NO)cc2)c(C(=O)Nc2ccc(Cl)cn2)c1 | null | null | CCO | Heteroatom Alkylation and Arylation | Amidoxime from nitrile and hydroxylamine | 5f2123b5002b6939ec57e4f55921371a47c78c3ff253c724d87881638fedcd4f | ad3f1127a4d99506976df608684863fb1e08b35faede2d4e31cf4ca96393cd2e | O=C(Nc1ccccc1C(=O)Nc1ccccn1)c1ccccc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[O;D1;H1:7]>>[NH2;D1;+0:1]-[C;H0;D3;+0:2](=[N;H0;D2;+0:6]-[O;D1;H1:7])-[c:3](:[c:4]):[c:5] | null | [] | 60 | CELSIUS | 8 | HOUR | To a suspension of compound N-(5-chloro(2-pyridyl)) {2-[(4-cyanophenyl)carbonylamino]-5-methoxyphenyl}carboxamide (150 mg) in EtOH (10 mL) was added hydroxyamine hydrochloride (80 mg) and Et3N (200 μL). The mixture was stirred at 60° C. overnight and the reaction was complete. The solvent was evaporated and the crude m... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine | Primary amine.Oxime | null | null | c1ccccc1.c1ccccc1.c1ccncc1 | null | CCO | 60 | 8 | COc1ccc(NC(=O)c2ccc(C#N)cc2)c(C(=O)Nc2ccc(Cl)cn2)c1.NO>CCO>COc1ccc(NC(=O)c2ccc(C(N)=NO)cc2)c(C(=O)Nc2ccc(Cl)cn2)c1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-972574041085479993d5ed752d7b11c2 | COc1ccc(NC(=O)c2ccc(C#N)cc2)c(C(=O)Nc2ccc(Cl)cn2)c1>>N#Cc1ccc(C(=O)Nc2ccc(O)cc2C(=O)Nc2ccc(Cl)cn2)cc1 | ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC(=C1)OC)NC(=O)C1=CC=C(C=C1)C#N.B(Br)(Br)Br>>ClC=1C=CC(=NC1)NC(=O)C1=CC(=CC=C1NC(=O)C1=CC=C(C=C1)C#N)O | C[O:14][c:13]1[cH:12][cH:11][c:10]([NH:9][C:7]([c:6]2[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:28][cH:27]2)=[O:8])[c:16]([C:17](=[O:18])[NH:19][c:20]2[cH:21][cH:22][c:23]([Cl:24])[cH:25][n:26]2)[cH:15]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][c:13]([OH:14])[cH:15][c:16]2[C:17](=[O:18])[NH:1... | COc1ccc(NC(=O)c2ccc(C#N)cc2)c(C(=O)Nc2ccc(Cl)cn2)c1 | N#Cc1ccc(C(=O)Nc2ccc(O)cc2C(=O)Nc2ccc(Cl)cn2)cc1 | null | null | C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C(Nc1ccccc1C(=O)Nc1ccccn1)c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 90 | [{"value": 90.0, "product": "ClC=1C=CC(=NC1)NC(=O)C1=CC(=CC=C1NC(=O)C1=CC=C(C=C1)C#N)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 72 | HOUR | To a suspension of compound N-(5-chloro(2-pyridyl)){2-[(4-cyanophenyl)-carbonylamino]-5-methoxyphenyl}carboxamide (500 mg, 1.2 mmol) in DCM (100 mL) at −78° C. was added BBr3 (2 mL). The mixture was stirred at ambient temperatures for 72 hours. The solid was collected by filtration and was washed by DCM and water, drie... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1ccccc1.c1ccncc1 | Other | C(Cl)Cl | null | 72 | COc1ccc(NC(=O)c2ccc(C#N)cc2)c(C(=O)Nc2ccc(Cl)cn2)c1>C(Cl)Cl>N#Cc1ccc(C(=O)Nc2ccc(O)cc2C(=O)Nc2ccc(Cl)cn2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-94770809738c4b598943bd373eeaa201 | Nc1ccc(Cl)cn1.O=c1[nH]c2ccc(Cl)cc2c(=O)o1>>Nc1ccc(Cl)cc1C(=O)Nc1ccc(Cl)cn1 | ClC1=CC=C2C(C(=O)OC(N2)=O)=C1.NC1=NC=C(C=C1)Cl.C[Si](C)(C)[N-][Si](C)(C)C.[K+].C1(=CC=CC=C1)C>>NC1=C(C=C(C=C1)Cl)C(=O)NC1=NC=C(C=C1)Cl | [NH2:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][n:18]1.O=c1o[c:9](=[O:10])[c:8]2[c:2]([nH:1]1)[cH:3][cH:4][c:5]([Cl:6])[cH:7]2>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([Cl:6])[cH:7][c:8]1[C:9](=[O:10])[NH:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][n:18]1 | Nc1ccc(Cl)cn1.O=c1[nH]c2ccc(Cl)cc2c(=O)o1 | Nc1ccc(Cl)cc1C(=O)Nc1ccc(Cl)cn1 | null | null | O1CCCC1 | Acylation | OtherReaction | b4c245015e48b9b60756b62e3f8985928af86452315d98417a25faace320d9ae | b609a70ccab739990a9ccc4ea2adcc77011bcd0c07154489a12420f7c0e7382e | O=C(Nc1ccccn1)c1ccccc1 | O=c1:[nH;D2;+0:1]:[c:2](:[c:3]):[c:4](:[c:5]):[c;H0;D3;+0:6](=[O;D1;H0:7]):o:1.[NH2;D1;+0:8]-[c:9](:[c:10]):[#7;a:11]:[c:12]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4](-[C;H0;D3;+0:6](=[O;D1;H0:7])-[NH;D2;+0:8]-[c:9](:[c:10]):[#7;a:11]:[c:12]):[c:5] | null | [] | -78 | CELSIUS | 0.5 | HOUR | To a solution of 2-amino-5-chloropyridine (787 mg, 6.1 mmol) in tetrahydrofuran (5 ml) was added 0.5M potassium bis(trimethylsilyl)amide in toluene (20 ml, 10.1 mmol) dropwise at −78° C. After stirred for additional 0.5 hr at −78° C., the mixture was added 5-chloroisatoic anhydride (1 g, 5.1 mmol) at −78° C. The mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary amide.Primary amine | c1ccc2ncocc2c1 | c1ccccc1 | c1ccccc1.c1ccncc1 | Other | O1CCCC1 | -78 | 0.5 | Nc1ccc(Cl)cn1.O=c1[nH]c2ccc(Cl)cc2c(=O)o1>O1CCCC1>Nc1ccc(Cl)cc1C(=O)Nc1ccc(Cl)cn1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-48fd1d68fa0249118488f86d53172bd6 | N#Cc1ccc(C(=O)O)c(F)c1.Nc1ccc(Cl)cc1C(=O)Nc1ccc(Cl)cn1>>N#Cc1ccc(C(=O)Nc2ccc(Cl)cc2C(=O)Nc2ccc(Cl)cn2)c(F)c1 | FC1=C(C(=O)O)C=CC(=C1)C#N.NC1=C(C=C(C=C1)Cl)C(=O)NC1=NC=C(C=C1)Cl.N1=CC=CC=C1>>ClC1=CC(=C(C=C1)NC(=O)C1=C(C=C(C=C1)C#N)F)C(NC1=NC=C(C=C1)Cl)=O | O[C:7]([c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:29][c:27]1[F:28])=[O:8].[NH2:9][c:10]1[cH:11][cH:12][c:13]([Cl:14])[cH:15][c:16]1[C:17](=[O:18])[NH:19][c:20]1[cH:21][cH:22][c:23]([Cl:24])[cH:25][n:26]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][c:13]([Cl:14])[cH:15][c:16]2[C:17](=[O:18]... | N#Cc1ccc(C(=O)O)c(F)c1.Nc1ccc(Cl)cc1C(=O)Nc1ccc(Cl)cn1 | N#Cc1ccc(C(=O)Nc2ccc(Cl)cc2C(=O)Nc2ccc(Cl)cn2)c(F)c1 | null | null | ClCCl.S(=O)(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1C(=O)Nc1ccccn1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH2;D1;+0:11]):[c:12]>>[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]):[c:12] | 111.3 | [{"value": 78.0, "product": "ClC1=CC(=C(C=C1)NC(=O)C1=C(C=C(C=C1)C#N)F)C(NC1=NC=C(C=C1)Cl)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 111.3, "product": "ClC1=CC(=C(C=C1)NC(=O)C1=C(C=C(C=C1)C#N)F)C(NC1=NC=C(C=C1)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of 2-fluoro-4-cyanobenzoic acid (1 g, 6.06 mmol) in thionyl chloride (5 ml) was refluxed for 2 hr. After concentration, the residue was dissolved in dichloromethane (5 ml). And a solution of the compound of (2-amino-5-chlorophenyl)-N-(5-chloro(2-pyridyl))carboxamide (1.2 g, 4.25 mmol) in dichloromethane (10 ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccncc1 | HO- | ClCCl.S(=O)(Cl)Cl | null | 8 | N#Cc1ccc(C(=O)O)c(F)c1.Nc1ccc(Cl)cc1C(=O)Nc1ccc(Cl)cn1>ClCCl.S(=O)(Cl)Cl>N#Cc1ccc(C(=O)Nc2ccc(Cl)cc2C(=O)Nc2ccc(Cl)cn2)c(F)c1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-a52a3fbcacdd46b986124493621699a2 | COC(=O)c1sccc1N.N#Cc1ccc(C(=O)Cl)cc1>>COC(=O)c1sccc1NC(=O)c1ccc(C#N)cc1 | C(#N)C1=CC=C(C(=O)Cl)C=C1.NC1=C(SC=C1)C(=O)OC.C(C)N(CC)CC>>C(#N)C1=CC=C(C=C1)C(=O)NC1=C(SC=C1)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[s:6][cH:7][cH:8][c:9]1[NH2:10].Cl[C:11](=[O:12])[c:13]1[cH:14][cH:15][c:16]([C:17]#[N:18])[cH:19][cH:20]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[s:6][cH:7][cH:8][c:9]1[NH:10][C:11](=[O:12])[c:13]1[cH:14][cH:15][c:16]([C:17]#[N:18])[cH:19][cH:20]1 | COC(=O)c1sccc1N.N#Cc1ccc(C(=O)Cl)cc1 | COC(=O)c1sccc1NC(=O)c1ccc(C#N)cc1 | null | null | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccsc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[#16;a:10]:[c:11]:[c:12]:[c:13]:1-[NH2;D1;+0:14]>>[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[#16;a:10]:[c:11]:[c:12]:[c:13]:1-[NH;D2;+0:14]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 91 | [{"value": 91.0, "product": "C(#N)C1=CC=C(C=C1)C(=O)NC1=C(SC=C1)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.5, "product": "C(#N)C1=CC=C(C=C1)C(=O)NC1=C(SC=C1)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A mixture of 4-cyanobenzoyl chloride (1.0500 g, 6.4 mmol), methyl 3-aminothiophenecarboxylate (1.0000 g, 6.4 mmol), and triethylamine (1 mL, 7.0 mmol) in dichloromethane was stirred at room temperature for 18 hours. The mixture was poured into a separatory funnel and washed by 1 N HCl. The organic layers were combined,... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccsc1.c1ccccc1 | HCl | ClCCl | null | 18 | COC(=O)c1sccc1N.N#Cc1ccc(C(=O)Cl)cc1>ClCCl>COC(=O)c1sccc1NC(=O)c1ccc(C#N)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-9aa9d5290cb44ccb99afcc55ad44795e | CC(C)(C)NS(=O)(=O)c1ccccc1-c1ccc(C(=O)Cl)cc1.Nc1ccsc1C(=O)Nc1cc(Cl)ccn1>>NS(=O)(=O)c1ccccc1-c1ccc(C(=O)Nc2ccsc2C(=O)Nc2ccc(Cl)cn2)cc1 | C(C)(C)(C)NS(=O)(=O)C1=C(C=CC=C1)C1=CC=C(C(=O)Cl)C=C1.NC1=C(SC=C1)C(=O)NC1=NC=CC(=C1)Cl.N1=CC=CC=C1.ClCCl.ClCCl>>ClC=1C=CC(=NC1)NC(=O)C=1SC=CC1NC(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)S(N)(=O)=O | CC(C)(C)[NH:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1-[c:11]1[cH:12][cH:13][c:14]([C:15](Cl)=[O:16])[cH:33][cH:34]1.[NH2:17][c:18]1[cH:19][cH:20][s:21][c:22]1[C:23](=[O:24])[NH:25][c:26]1[cH:27][c:29]([Cl:30])[cH:28][cH:31][n:32]1>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1-[c:... | CC(C)(C)NS(=O)(=O)c1ccccc1-c1ccc(C(=O)Cl)cc1.Nc1ccsc1C(=O)Nc1cc(Cl)ccn1 | NS(=O)(=O)c1ccccc1-c1ccc(C(=O)Nc2ccsc2C(=O)Nc2ccc(Cl)cn2)cc1 | null | null | null | Acylation | OtherReaction | 62b79e27f73e217708be777171a101fdbc2ae1e8bb0a9b0fa120e1de8f226bfb | 5bed3f68e2efbf0da9a9b01be7a80f098581b44c7deee6d8009e459217c3f840 | O=C(Nc1ccsc1C(=O)Nc1ccccn1)c1ccc(-c2ccccc2)cc1 | C-C(-C)(-C)-[NH;D2;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5].Cl-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10].[Cl;D1;H0:11]-[c;H0;D3;+0:12]1:[cH;D2;+0:13]:[c:14](-[#7:15]-[C:16](=[O;D1;H0:17])-[c:18]2:[#16;a:19]:[c:20]:[c:21]:[c:22]:2-[NH2;D1;+0:23]):[#7;a:24]:[cH;D2;+0:25]:[cH;D2;+0:26]:1>>[Cl;D1;H0:11]-[c;H... | null | [] | null | null | null | null | A solution of 4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)benzoyl chloride (1 equiv), 3-amino-2-(4-chloro-2-pyridinyl)aminocarbonyl thiophene (1 equiv), pyridine (5 equiv) in dichloromethane was stirred at rt overnight. The mixture was diluted with dichloromethane, washed with water, dried over Na2SO4, filtered and evapor... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Sulfonamide.Aromatic halide.Primary amine | Sulfonamide.Aromatic halide.Secondary amide | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccccc1.c1ccsc1.c1ccncc1 | HCl | null | null | null | CC(C)(C)NS(=O)(=O)c1ccccc1-c1ccc(C(=O)Cl)cc1.Nc1ccsc1C(=O)Nc1cc(Cl)ccn1>>NS(=O)(=O)c1ccccc1-c1ccc(C(=O)Nc2ccsc2C(=O)Nc2ccc(Cl)cn2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-e3397632786e4f3d840b2b82c219eed2 | CC1=CC(=O)OC1=O.Nc1ccc(Br)cn1>>CC1=CC(=O)N(c2ccc(Br)cn2)C1=O | C1(\C(\C)=C/C(=O)O1)=O.NC1=NC=C(C=C1)Br>>BrC=1C=CC(=NC1)N1C(C(=CC1=O)C)=O | O1[C:4](=[O:5])[CH:3]=[C:2]([CH3:1])[C:14]1=[O:15].[NH2:6][c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][n:13]1>>[CH3:1][C:2]1=[CH:3][C:4](=[O:5])[N:6]([c:7]2[cH:8][cH:9][c:10]([Br:11])[cH:12][n:13]2)[C:14]1=[O:15] | CC1=CC(=O)OC1=O.Nc1ccc(Br)cn1 | CC1=CC(=O)N(c2ccc(Br)cn2)C1=O | null | null | C1(=CC=CC=C1)C | Acylation | OtherReaction | cab1acd179957d4f5c27ba23f314ee257f7d508deff2838c7964b1019063e651 | 2a4a20e639c386292668b0b265a8e1b50d707d5f0576437dc5ade3e7fd444d29 | O=C1C=CC(=O)N1c1ccccn1 | [C;D1;H3:1]-[C:2]1=[C:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-O-[C;H0;D3;+0:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[#7;a:11]:[c:12]>>[C;D1;H3:1]-[C:2]1=[C:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[N;H0;D3;+0:8](-[c:9](:[c:10]):[#7;a:11]:[c:12])-[C;H0;D3;+0:6]-1=[O;D1;H0:7] | 71 | [{"value": 71.0, "product": "BrC=1C=CC(=NC1)N1C(C(=CC1=O)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.8, "product": "BrC=1C=CC(=NC1)N1C(C(=CC1=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of citraconic anhydride (1.00 mL, 11.1 mmol) and 2-amino-5-bromopyridine (1.93 g, 11.2 mmol) in toluene (60 mL) was heated to reflux overnight. The solution was cooled down, filtered. The filtrate was concentrated in vacuo to give a solid (2.10 g, yield: 71%). MS 267 and 269 (M+H).
Conditions: See reaction.no... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Substituted dicarboximide | C1=CCOC1 | C1=CC[NH]C1 | C1=CC[NH]C1.c1ccncc1 | HO- | C1(=CC=CC=C1)C | null | null | CC1=CC(=O)OC1=O.Nc1ccc(Br)cn1>C1(=CC=CC=C1)C>CC1=CC(=O)N(c2ccc(Br)cn2)C1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-0cd93d207e004979a92ba2c0b525333b | N#Cc1cccc(O)c1.O=[N+]([O-])c1ccccc1F>>N#Cc1cccc(Oc2ccccc2[N+](=O)[O-])c1 | FC1=C(C=CC=C1)[N+](=O)[O-].OC=1C=C(C#N)C=CC1.C(=O)([O-])[O-].[K+].[K+]>>[N+](=O)([O-])C1=C(OC=2C=C(C#N)C=CC2)C=CC=C1 | [N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([OH:8])[cH:18]1.F[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[N+:15](=[O:16])[O-:17]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[N+:15](=[O:16])[O-:17])[cH:18]1 | N#Cc1cccc(O)c1.O=[N+]([O-])c1ccccc1F | N#Cc1cccc(Oc2ccccc2[N+](=O)[O-])c1 | null | null | CCOC(=O)C.CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | e4ea1e38252bc3b9c5ec04486386725e6570ab3860d45e337a1d131319bbf0fc | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ccccc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]):[c:2]:[c:3] | 99.2 | [{"value": 99.0, "product": "[N+](=O)([O-])C1=C(OC=2C=C(C#N)C=CC2)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.2, "product": "[N+](=O)([O-])C1=C(OC=2C=C(C#N)C=CC2)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 3 | HOUR | To a solution of 2-fluoro nitrobenzene (1.41 g, 10 mmol, 1.0 equiv) and 3-hydroxybenzonitrile (1.19 g, 1.0 equiv) in 10 mL of DMF was added K2CO3 (2.76 g, 2 equiv). After stirring at 60° C. for 3 h, the mixture was diluted with EtOAc and washed with H2O. The organic layer was dried over MgSO4, filtered and evaporated t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HF | CCOC(=O)C.CN(C)C=O | 60 | 3 | N#Cc1cccc(O)c1.O=[N+]([O-])c1ccccc1F>CCOC(=O)C.CN(C)C=O>N#Cc1cccc(Oc2ccccc2[N+](=O)[O-])c1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-a8a6e596c40a42de81190832f7c60776 | N#Cc1cccc(Oc2ccccc2[N+](=O)[O-])c1>>N#Cc1cccc(Oc2ccccc2N)c1 | [N+](=O)([O-])C1=C(OC=2C=C(C#N)C=CC2)C=CC=C1.O.O.Cl[Sn]Cl>>NC1=C(OC=2C=C(C#N)C=CC2)C=CC=C1 | O=[N+:15]([O-])[c:14]1[c:9]([O:8][c:7]2[cH:6][cH:5][cH:4][c:3]([C:2]#[N:1])[cH:16]2)[cH:10][cH:11][cH:12][cH:13]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[NH2:15])[cH:16]1 | N#Cc1cccc(Oc2ccccc2[N+](=O)[O-])c1 | N#Cc1cccc(Oc2ccccc2N)c1 | null | null | CCO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(Oc2ccccc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 99 | [{"value": 99.0, "product": "NC1=C(OC=2C=C(C#N)C=CC2)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.9, "product": "NC1=C(OC=2C=C(C#N)C=CC2)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3-(2-nitrophenoxy)benzonitrile (1.21 g, 5 mmol, 1.0 equiv) in 30 mL of EtOH was treated with SnCl2.2H2O (3-38 g, 3 equiv) at reflux for 4 h. The volatile was evaporated and the residue was redissolved in EtOAc, washed with saturated aqueous NaHCO3 and 1N NaOH. The organic layer was dried over MgSO4, filte... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | CCO | null | null | N#Cc1cccc(Oc2ccccc2[N+](=O)[O-])c1>CCO>N#Cc1cccc(Oc2ccccc2N)c1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-95c8195467304d848c25fbc20d6485d1 | Fc1ccc2c3c([nH]c2c1)CNCC3>>Fc1ccc2c(c1)[nH]c1cnccc12 | FC1=CC=C2C=3CCNCC3NC2=C1>>FC1=CC=C2C=3C=CN=CC3NC2=C1 | [F:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[nH:8][c:9]1[c:14]2[CH2:13][CH2:12][NH:11][CH2:10]1>>[F:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[nH:8][c:9]1[cH:10][n:11][cH:12][cH:13][c:14]21 | Fc1ccc2c3c([nH]c2c1)CNCC3 | Fc1ccc2c(c1)[nH]c1cnccc12 | null | [Pd] | null | Oxidation | OtherReaction | 49cd6b747906212b33e37895c90915d6d06eae54435fd41a9563191b791d0a0e | 45f806b8e00071c3429c43b3544e10767c5f82b269d7c53bc7fada9a5eb3b8c6 | c1ccc2c(c1)[nH]c1cnccc12 | [#7;a:1]1:[c:2]:[c:3]:[c:4]2:[c:5]:1-[CH2;D2;+0:6]-[NH;D2;+0:7]-[CH2;D2;+0:8]-[CH2;D2;+0:9]-2>>[#7;a:1]1:[c:2]:[c:3]:[c:4]2:[cH;D2;+0:9]:[cH;D2;+0:8]:[n;H0;D2;+0:7]:[cH;D2;+0:6]:[c:5]:1:2 | 88 | [{"value": 88.0, "product": "FC1=CC=C2C=3C=CN=CC3NC2=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.5, "product": "FC1=CC=C2C=3C=CN=CC3NC2=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 7-fluoro-2,3,4,9-tetrahydro-1H-β-carboline (3.5 g, 18.42 mmol) was suspended in xylenes (60 ml) in a 250 ml round-bottom flask equipped with a condenser that was open to the atmosphere, and heated. To this hot reaction mixture was added Pd/C (10 wt %, 0.2 eq, 700 mg) and the mixture refluxed in xylenes overnight (12-14... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | null | c1ccc2c3c([nH]c2c1)CNCC3 | c1ccc2c(c1)[nH]c1cnccc12 | c1ccc2c(c1)[nH]c1cnccc12 | null | [Pd] | null | null | Fc1ccc2c3c([nH]c2c1)CNCC3>[Pd]>Fc1ccc2c(c1)[nH]c1cnccc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-b635247e1c454b27ad6122238f839d06 | CO.O=[N+]([O-])c1c(F)c(Cl)cc2c1[nH]c1cnccc12>>COc1c(Cl)cc2c([nH]c3cnccc32)c1[N+](=O)[O-] | O.CO.[H-].[Na+].ClC=1C=C2C=3C=CN=CC3NC2=C(C1F)[N+](=O)[O-]>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1OC)[N+](=O)[O-] | [CH3:1][OH:2].F[c:3]1[c:4]([Cl:5])[cH:6][c:7]2[c:8]([nH:9][c:10]3[cH:11][n:12][cH:13][cH:14][c:15]23)[c:16]1[N+:17](=[O:18])[O-:19]>>[CH3:1][O:2][c:3]1[c:4]([Cl:5])[cH:6][c:7]2[c:8]([nH:9][c:10]3[cH:11][n:12][cH:13][cH:14][c:15]23)[c:16]1[N+:17](=[O:18])[O-:19] | CO.O=[N+]([O-])c1c(F)c(Cl)cc2c1[nH]c1cnccc12 | COc1c(Cl)cc2c([nH]c3cnccc32)c1[N+](=O)[O-] | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | fb66b9ea00ae64d918ad46a3013245b82db1faee7bd623c477afa2b63f708680 | 23dafde907f7a74dc1d4cc65967b00a9b318897fe61a3d3c4a9fddf320485f17 | c1ccc2c(c1)[nH]c1cnccc12 | F-[c;H0;D3;+0:1]1:[c:2](-[#7;+:3]):[c:4](:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]):[c:9]:[c:10]:[c:11]:1-[Cl;D1;H0:12].[C;D1;H3:13]-[OH;D1;+0:14]>>[#7;+:3]-[c:2]1:[c:4](:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]):[c:9]:[c:10]:[c:11](-[Cl;D1;H0:12]):[c;H0;D3;+0:1]:1-[O;H0;D2;+0:14]-[C;D1;H3:13] | 97 | [{"value": 97.0, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1OC)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.7, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1OC)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | Methanol (0.462 ml, 11.4 mmol) was added to a stirring suspension of NaH (684 mg, 17.1 mmol) in DMF (10 ml) under an argon atmosphere. The resulting solution was allowed to stir at RT for 20 min. 6-chloro-7-fluoro-8-nitro-9H-β-carboline (500 mg, 1.9 mmol) was added to the stirring solution and the resulting mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Methanol | Ether | c1ccc2c(c1)[nH]c1cnccc12 | c1ccc2c(c1)[nH]c1cnccc12 | c1ccc2c(c1)[nH]c1cnccc12 | HF | CN(C)C=O | null | 0.333333 | CO.O=[N+]([O-])c1c(F)c(Cl)cc2c1[nH]c1cnccc12>CN(C)C=O>COc1c(Cl)cc2c([nH]c3cnccc32)c1[N+](=O)[O-] |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-becf4864ac49431f98c4bd814a232da9 | COc1c(Cl)cc2c([nH]c3cnccc32)c1[N+](=O)[O-]>>COc1c(Cl)cc2c([nH]c3cnccc32)c1N | ClC=1C=C2C=3C=CN=CC3NC2=C(C1OC)[N+](=O)[O-].[H][H].C(=O)(O)[O-].[Na+]>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1OC)N | O=[N+:17]([O-])[c:16]1[c:3]([O:2][CH3:1])[c:4]([Cl:5])[cH:6][c:7]2[c:8]1[nH:9][c:10]1[cH:11][n:12][cH:13][cH:14][c:15]21>>[CH3:1][O:2][c:3]1[c:4]([Cl:5])[cH:6][c:7]2[c:8]([nH:9][c:10]3[cH:11][n:12][cH:13][cH:14][c:15]23)[c:16]1[NH2:17] | COc1c(Cl)cc2c([nH]c3cnccc32)c1[N+](=O)[O-] | COc1c(Cl)cc2c([nH]c3cnccc32)c1N | null | [Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2c(c1)[nH]c1cnccc12 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]:[c:8]:[#7;a:9]>>[#7;a:9]:[c:8]:[c:7]:[#7;a:6]:[c:4](:[c:5]):[c:2](-[NH2;D1;+0:1]):[c:3] | 112.3 | [{"value": 112.3, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1OC)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 6-chloro-7-methoxy-8-nitro-9H-β-carboline (510 mg, 1.84 mmol) was suspended in 50 ml of methanol and 100 mg of Pd/C (10%) was added. The flask was fitted with a balloon of hydrogen and the reaction mixture was stirred overnight at RT. Upon filtration through a pad of celite and evaporation of the methanol, a dark brown... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2c(c1)[nH]c1cnccc12 | Other | [Pd].CO | null | 8 | COc1c(Cl)cc2c([nH]c3cnccc32)c1[N+](=O)[O-]>[Pd].CO>COc1c(Cl)cc2c([nH]c3cnccc32)c1N |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-dbeb848e8fc94ab2bca7c131609a2899 | COc1c(Cl)cc2c([nH]c3cnccc32)c1N.Cc1ncccc1C(=O)O>>COc1c(Cl)cc2c([nH]c3cnccc32)c1NC(=O)c1cccnc1C | ClC=1C=C2C=3C=CN=CC3NC2=C(C1OC)N.CCN=C=NCCCN(C)C.CC1=C(C(=O)O)C=CC=N1>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1OC)NC(C1=C(N=CC=C1)C)=O | [CH3:1][O:2][c:3]1[c:4]([Cl:5])[cH:6][c:7]2[c:8]([nH:9][c:10]3[cH:11][n:12][cH:13][cH:14][c:15]23)[c:16]1[NH2:17].O[C:18](=[O:19])[c:20]1[cH:21][cH:22][cH:23][n:24][c:25]1[CH3:26]>>[CH3:1][O:2][c:3]1[c:4]([Cl:5])[cH:6][c:7]2[c:8]([nH:9][c:10]3[cH:11][n:12][cH:13][cH:14][c:15]23)[c:16]1[NH:17][C:18](=[O:19])[c:20]1[cH:2... | COc1c(Cl)cc2c([nH]c3cnccc32)c1N.Cc1ncccc1C(=O)O | COc1c(Cl)cc2c([nH]c3cnccc32)c1NC(=O)c1cccnc1C | null | null | N1=CC=CC=C1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1cccc2c1[nH]c1cnccc12)c1cccnc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[C;D1;H3:6]):[#7;a:7]:[c:8].[#7;a:9]:[c:10]:[c:11]:[#7;a:12]:[c:13](:[c:14]):[c:15](-[NH2;D1;+0:16]):[c:17]>>[#7;a:9]:[c:10]:[c:11]:[#7;a:12]:[c:13](:[c:14]):[c:15](-[NH;D2;+0:16]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[C;D1;H3:6]):[#7;a:7]:[c:8]):[c:17] | 50 | [{"value": 50.0, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1OC)NC(C1=C(N=CC=C1)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | 6-chloro-7-methoxy-9H-β-carbolin-8-ylamine (100 mg, 0.4 mmol), EDCI (125 mg, 0.64 mmol) and 2-methyl nicotinic acid (66 mg, 0.48 mmol) were taken in a round-bottom flask and suspended in pyridine (2 ml). The resulting mixture was heated at 80° C. overnight. The pyridine was then removed by rotary evaporation and 5% Na2... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2c(c1)[nH]c1cnccc12.c1ccncc1 | HO- | N1=CC=CC=C1 | 80 | null | COc1c(Cl)cc2c([nH]c3cnccc32)c1N.Cc1ncccc1C(=O)O>N1=CC=CC=C1>COc1c(Cl)cc2c([nH]c3cnccc32)c1NC(=O)c1cccnc1C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-64f20c9068f249069d4f82b9cd087d27 | COc1c(Cl)cc2c([nH]c3cnccc32)c1N.Cc1ncncc1C(=O)O>>COc1c(Cl)cc2c([nH]c3cnccc32)c1NC(=O)c1cncnc1C | ClC=1C=C2C=3C=CN=CC3NC2=C(C1OC)N.CC1=NC=NC=C1C(=O)O>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1OC)NC(=O)C=1C(=NC=NC1)C | [CH3:1][O:2][c:3]1[c:4]([Cl:5])[cH:6][c:7]2[c:8]([nH:9][c:10]3[cH:11][n:12][cH:13][cH:14][c:15]23)[c:16]1[NH2:17].O[C:18](=[O:19])[c:20]1[cH:21][n:22][cH:23][n:24][c:25]1[CH3:26]>>[CH3:1][O:2][c:3]1[c:4]([Cl:5])[cH:6][c:7]2[c:8]([nH:9][c:10]3[cH:11][n:12][cH:13][cH:14][c:15]23)[c:16]1[NH:17][C:18](=[O:19])[c:20]1[cH:21... | COc1c(Cl)cc2c([nH]c3cnccc32)c1N.Cc1ncncc1C(=O)O | COc1c(Cl)cc2c([nH]c3cnccc32)c1NC(=O)c1cncnc1C | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1cccc2c1[nH]c1cnccc12)c1cncnc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:1-[C;D1;H3:9].[#7;a:10]:[c:11]:[c:12]:[#7;a:13]:[c:14](:[c:15]):[c:16](-[NH2;D1;+0:17]):[c:18]>>[#7;a:10]:[c:11]:[c:12]:[#7;a:13]:[c:14](:[c:15]):[c:16](-[NH;D2;+0:17]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:1-[C;D... | 80 | [{"value": 80.0, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1OC)NC(=O)C=1C(=NC=NC1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The desired compound was prepared according to Method A from 6-chloro-7-methoxy-9H-beta-carbolin-8-ylamine and 4-methyl-5-pyrimidine carboxylic acid in 80% yield.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2c(c1)[nH]c1cnccc12.c1cncnc1 | HO- | null | null | null | COc1c(Cl)cc2c([nH]c3cnccc32)c1N.Cc1ncncc1C(=O)O>>COc1c(Cl)cc2c([nH]c3cnccc32)c1NC(=O)c1cncnc1C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-43669270af0443af8dcc4c27264a3edb | CC[O-].O=[N+]([O-])c1c(F)c(Cl)cc2c1[nH]c1cnccc12>>CCOc1c(Cl)cc2c([nH]c3cnccc32)c1[N+](=O)[O-] | [O-]CC.[Na+].ClC=1C=C2C=3C=CN=CC3NC2=C(C1F)[N+](=O)[O-].Cl>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1OCC)[N+](=O)[O-] | [CH3:1][CH2:2][O-:3].F[c:4]1[c:5]([Cl:6])[cH:7][c:8]2[c:9]([nH:10][c:11]3[cH:12][n:13][cH:14][cH:15][c:16]23)[c:17]1[N+:18](=[O:19])[O-:20]>>[CH3:1][CH2:2][O:3][c:4]1[c:5]([Cl:6])[cH:7][c:8]2[c:9]([nH:10][c:11]3[cH:12][n:13][cH:14][cH:15][c:16]23)[c:17]1[N+:18](=[O:19])[O-:20] | CC[O-].O=[N+]([O-])c1c(F)c(Cl)cc2c1[nH]c1cnccc12 | CCOc1c(Cl)cc2c([nH]c3cnccc32)c1[N+](=O)[O-] | null | null | CS(=O)C.O | Heteroatom Alkylation and Arylation | OtherReaction | 1f0182aba60bda71c1cacefb53d4629b0f8909ff869c59859818a59c4bf2c769 | 51fd03eb6a688046e417b9ed09ea0e72062396d005af1318b9b5f376a97da959 | c1ccc2c(c1)[nH]c1cnccc12 | F-[c;H0;D3;+0:1]1:[c:2](-[#7;+:3]):[c:4](:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]):[c:9]:[c:10]:[c:11]:1-[Cl;D1;H0:12].[C;D1;H3:13]-[C:14]-[O-;H0;D1:15]>>[#7;+:3]-[c:2]1:[c:4](:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]):[c:9]:[c:10]:[c:11](-[Cl;D1;H0:12]):[c;H0;D3;+0:1]:1-[O;H0;D2;+0:15]-[C:14]-[C;D1;H3:13] | 40 | [{"value": 40.0, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1OCC)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Sodium ethoxide (232 mg, 3.4 mmol) was added to a solution of 6-chloro-7-fluoro-8-nitro-9H-β-carboline (200 mg, 0.76 mmol) in DMSO (4 ml) and the reaction mixture allowed to stir overnight. The reaction mixture was diluted with water and the pH of the solution was adjusted to about 4 by adding 1N HCl. The aqueous solut... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Ether | c1ccc2c(c1)[nH]c1cnccc12 | c1ccc2c(c1)[nH]c1cnccc12 | c1ccc2c(c1)[nH]c1cnccc12 | Other | CS(=O)C.O | null | 8 | CC[O-].O=[N+]([O-])c1c(F)c(Cl)cc2c1[nH]c1cnccc12>CS(=O)C.O>CCOc1c(Cl)cc2c([nH]c3cnccc32)c1[N+](=O)[O-] |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-a246859ab003474d815d88040d024039 | CCOc1c(Cl)cc2c([nH]c3cnccc32)c1N.Cc1ncccc1C(=O)O>>CCOc1c(Cl)cc2c([nH]c3cnccc32)c1NC(=O)c1cccnc1C | ClC=1C=C2C=3C=CN=CC3NC2=C(C1OCC)N.CC1=C(C(=O)O)C=CC=N1>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1OCC)NC(C1=C(N=CC=C1)C)=O | [CH3:1][CH2:2][O:3][c:4]1[c:5]([Cl:6])[cH:7][c:8]2[c:9]([nH:10][c:11]3[cH:12][n:13][cH:14][cH:15][c:16]23)[c:17]1[NH2:18].O[C:19](=[O:20])[c:21]1[cH:22][cH:23][cH:24][n:25][c:26]1[CH3:27]>>[CH3:1][CH2:2][O:3][c:4]1[c:5]([Cl:6])[cH:7][c:8]2[c:9]([nH:10][c:11]3[cH:12][n:13][cH:14][cH:15][c:16]23)[c:17]1[NH:18][C:19](=[O:... | CCOc1c(Cl)cc2c([nH]c3cnccc32)c1N.Cc1ncccc1C(=O)O | CCOc1c(Cl)cc2c([nH]c3cnccc32)c1NC(=O)c1cccnc1C | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1cccc2c1[nH]c1cnccc12)c1cccnc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[C;D1;H3:6]):[#7;a:7]:[c:8].[#7;a:9]:[c:10]:[c:11]:[#7;a:12]:[c:13](:[c:14]):[c:15](-[NH2;D1;+0:16]):[c:17]>>[#7;a:9]:[c:10]:[c:11]:[#7;a:12]:[c:13](:[c:14]):[c:15](-[NH;D2;+0:16]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[C;D1;H3:6]):[#7;a:7]:[c:8]):[c:17] | 40 | [{"value": 40.0, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1OCC)NC(C1=C(N=CC=C1)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The desired compound was prepared according to Method A from 6-chloro-7-ethoxy-9H-β-carbolin-8-ylamine and 2-methylnicotinic acid in 40% yield.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2c(c1)[nH]c1cnccc12.c1ccncc1 | HO- | null | null | null | CCOc1c(Cl)cc2c([nH]c3cnccc32)c1N.Cc1ncccc1C(=O)O>>CCOc1c(Cl)cc2c([nH]c3cnccc32)c1NC(=O)c1cccnc1C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-88fe38c5b72d4d6db3a391486d78fc65 | CN1CCNCC1.O=[N+]([O-])c1c(F)c(Cl)cc2c1[nH]c1cnccc12>>CN1CCN(c2c(Cl)cc3c([nH]c4cnccc43)c2[N+](=O)[O-])CC1 | CS(=O)C.ClC=1C=C2C=3C=CN=CC3NC2=C(C1F)[N+](=O)[O-].CN1CCNCC1.CCN(C(C)C)C(C)C>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1N1CCN(CC1)C)[N+](=O)[O-] | [CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:23][CH2:24]1.F[c:6]1[c:7]([Cl:8])[cH:9][c:10]2[c:11]([nH:12][c:13]3[cH:14][n:15][cH:16][cH:17][c:18]23)[c:19]1[N+:20](=[O:21])[O-:22]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[c:7]([Cl:8])[cH:9][c:10]3[c:11]([nH:12][c:13]4[cH:14][n:15][cH:16][cH:17][c:18]34)[c:19]2[N+:20](=[O:21])[O... | CN1CCNCC1.O=[N+]([O-])c1c(F)c(Cl)cc2c1[nH]c1cnccc12 | CN1CCN(c2c(Cl)cc3c([nH]c4cnccc43)c2[N+](=O)[O-])CC1 | null | null | O | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 77d260fc2f8702014dbc060ee1f8e9930a9aeacb102b3b42c4765e2337dbc842 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cc2c(cn1)[nH]c1cc(N3CCNCC3)ccc12 | F-[c;H0;D3;+0:1]1:[c:2](-[#7;+:3]):[c:4](:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]):[c:9]:[c:10]:[c:11]:1-[Cl;D1;H0:12].[#7:13]1-[C:14]-[C:15]-[NH;D2;+0:16]-[C:17]-[C:18]-1>>[#7;+:3]-[c:2]1:[c:4](:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]):[c:9]:[c:10]:[c:11](-[Cl;D1;H0:12]):[c;H0;D3;+0:1]:1-[N;H0;D3;+0:16]1-[C:15]-[C:14]-[#7:13]-[C:18]-[C:1... | 91 | [{"value": 91.0, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1N1CCN(CC1)C)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.4, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1N1CCN(CC1)C)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a DMSO solution (4 ml) of 200 mg (0.755 mmol) of 6-chloro-7-fluoro-8-nitro-9H-β-carboline was added 1-methylpiperazine (226 mg, 2.26 mmol) and DIEA (400 mg, 3.09 mmol) via a syringe. The reaction was allowed to stir at RT overnight. Upon addition of water, an orange solid precipitated out. The solid was filtered, wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1ccc2c(c1)[nH]c1cnccc12 | C1C[NH]CC[NH]1.c1ccc2c(c1)[nH]c1cnccc12 | C1C[NH]CC[NH]1.c1ccc2c(c1)[nH]c1cnccc12 | HF | O | null | 8 | CN1CCNCC1.O=[N+]([O-])c1c(F)c(Cl)cc2c1[nH]c1cnccc12>O>CN1CCN(c2c(Cl)cc3c([nH]c4cnccc43)c2[N+](=O)[O-])CC1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-999c390fd09a4602b272acf153fb1264 | CN1CCN(c2c(Cl)cc3c([nH]c4cnccc43)c2[N+](=O)[O-])CC1>>CN1CCN(c2c(Cl)cc3c([nH]c4cnccc43)c2N)CC1 | ClC=1C=C2C=3C=CN=CC3NC2=C(C1N1CCN(CC1)C)[N+](=O)[O-]>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1N1CCN(CC1)C)N | O=[N+:20]([O-])[c:19]1[c:6]([N:5]2[CH2:4][CH2:3][N:2]([CH3:1])[CH2:22][CH2:21]2)[c:7]([Cl:8])[cH:9][c:10]2[c:11]1[nH:12][c:13]1[cH:14][n:15][cH:16][cH:17][c:18]21>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[c:7]([Cl:8])[cH:9][c:10]3[c:11]([nH:12][c:13]4[cH:14][n:15][cH:16][cH:17][c:18]34)[c:19]2[NH2:20])[CH2:21][CH2:22]1 | CN1CCN(c2c(Cl)cc3c([nH]c4cnccc43)c2[N+](=O)[O-])CC1 | CN1CCN(c2c(Cl)cc3c([nH]c4cnccc43)c2N)CC1 | null | [Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1cc2c(cn1)[nH]c1cc(N3CCNCC3)ccc12 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]:[c:8]:[#7;a:9]>>[#7;a:9]:[c:8]:[c:7]:[#7;a:6]:[c:4](:[c:5]):[c:2](-[NH2;D1;+0:1]):[c:3] | 55.2 | [{"value": 55.0, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1N1CCN(CC1)C)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.2, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1N1CCN(CC1)C)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Suspended 236 mg of 6-chloro-7-(4-methyl-piperazin-1-yl)-8-nitro-9H-β-carboline in 100 ml of methanol and added 10% Pd/C(48 mg) under argon. The flask was flushed with hydrogen (3×) and the reaction mixture was stirred under a hydrogen atmosphere at RT overnight. The reaction mixture was filtered and Pd/C was removed u... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | C1C[NH]CC[NH]1.c1ccc2c(c1)[nH]c1cnccc12 | Other | [Pd].CO | null | 8 | CN1CCN(c2c(Cl)cc3c([nH]c4cnccc43)c2[N+](=O)[O-])CC1>[Pd].CO>CN1CCN(c2c(Cl)cc3c([nH]c4cnccc43)c2N)CC1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-e81169359fb94455a9946173265fc171 | CN1CCN(c2c(Cl)cc3c([nH]c4cnccc43)c2N)CC1.O=C(O)c1cccnc1Cl>>CN1CCN(c2c(Cl)cc3c([nH]c4cnccc43)c2NC(=O)c2cccnc2Cl)CC1 | ClC=1C=C2C=3C=CN=CC3NC2=C(C1N1CCN(CC1)C)N.ClC1=C(C(=O)O)C=CC=N1>>ClC1=C(C(=O)NC=2C(=C(C=C3C=4C=CN=CC4NC23)Cl)N2CCN(CC2)C)C=CC=N1 | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[c:7]([Cl:8])[cH:9][c:10]3[c:11]([nH:12][c:13]4[cH:14][n:15][cH:16][cH:17][c:18]34)[c:19]2[NH2:20])[CH2:30][CH2:31]1.O[C:21](=[O:22])[c:23]1[cH:24][cH:25][cH:26][n:27][c:28]1[Cl:29]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[c:7]([Cl:8])[cH:9][c:10]3[c:11]([nH:12][c:13]4[cH:14][n:15... | CN1CCN(c2c(Cl)cc3c([nH]c4cnccc43)c2N)CC1.O=C(O)c1cccnc1Cl | CN1CCN(c2c(Cl)cc3c([nH]c4cnccc43)c2NC(=O)c2cccnc2Cl)CC1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1c(N2CCNCC2)ccc2c1[nH]c1cnccc12)c1cccnc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[Cl;D1;H0:6]):[#7;a:7]:[c:8].[#7;a:9]:[c:10]:[c:11]:[#7;a:12]:[c:13](:[c:14]):[c:15](-[NH2;D1;+0:16]):[c:17]>>[#7;a:9]:[c:10]:[c:11]:[#7;a:12]:[c:13](:[c:14]):[c:15](-[NH;D2;+0:16]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[Cl;D1;H0:6]):[#7;a:7]:[c:8]):[c:17] | 25 | [{"value": 25.0, "product": "ClC1=C(C(=O)NC=2C(=C(C=C3C=4C=CN=CC4NC23)Cl)N2CCN(CC2)C)C=CC=N1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The desired compound was prepared according to Method A from 6-chloro-7-(4-methyl-piperazin-1-yl)-8-amino-9H-β-carboline and 2-chloro-nicotinic acid in 25% yield.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1C[NH]CC[NH]1.c1ccc2c(c1)[nH]c1cnccc12.c1ccncc1 | HO- | null | null | null | CN1CCN(c2c(Cl)cc3c([nH]c4cnccc43)c2N)CC1.O=C(O)c1cccnc1Cl>>CN1CCN(c2c(Cl)cc3c([nH]c4cnccc43)c2NC(=O)c2cccnc2Cl)CC1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-893383a6f6244cf79604ae38fdab3519 | CN1C(=O)CC(C(=O)O)C1(C)C.Nc1cc(Cl)cc2c1[nH]c1cnccc12>>CN1C(=O)CC(C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)C1(C)C | ClC=1C=C2C=3C=CN=CC3NC2=C(C1)N.CN1C(C(CC1=O)C(=O)O)(C)C>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)C1C(N(C(C1)=O)C)(C)C | O[C:7]([CH:6]1[CH2:5][C:3](=[O:4])[N:2]([CH3:1])[C:24]1([CH3:25])[CH3:26])=[O:8].[NH2:9][c:10]1[cH:11][c:12]([Cl:13])[cH:14][c:15]2[c:16]1[nH:17][c:18]1[cH:19][n:20][cH:21][cH:22][c:23]21>>[CH3:1][N:2]1[C:3](=[O:4])[CH2:5][CH:6]([C:7](=[O:8])[NH:9][c:10]2[cH:11][c:12]([Cl:13])[cH:14][c:15]3[c:16]2[nH:17][c:18]2[cH:19][... | CN1C(=O)CC(C(=O)O)C1(C)C.Nc1cc(Cl)cc2c1[nH]c1cnccc12 | CN1C(=O)CC(C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)C1(C)C | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1CC(C(=O)Nc2cccc3c2[nH]c2cnccc23)CN1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[#7:5]-[C:6](=[O;D1;H0:7])-[C:8]-1.[#7;a:9]:[c:10]:[c:11]:[#7;a:12]:[c:13](:[c:14]):[c:15](-[NH2;D1;+0:16]):[c:17]>>[#7;a:9]:[c:10]:[c:11]:[#7;a:12]:[c:13](:[c:14]):[c:15](-[NH;D2;+0:16]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[#7:5]-[C:6](=[O;D1;H0:7])-[C:8]-1):[c:17] | 68 | [{"value": 68.0, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)C1C(N(C(C1)=O)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The desired compound was prepared according to Method B from 6-chloro-9H-β-carboline-8-ylamine and 1,2,2-trimethyl-5-oxo-pyrrolidine-3-carboxylic acid in 68% yield.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CC[NH]C1.c1ccc2c(c1)[nH]c1cnccc12 | HO- | null | null | null | CN1C(=O)CC(C(=O)O)C1(C)C.Nc1cc(Cl)cc2c1[nH]c1cnccc12>>CN1C(=O)CC(C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)C1(C)C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-d46c8f0fc93a42c984faa43c8c9ef0d6 | N[C@@H](CO)C(=O)OCc1ccccc1.O=Cc1ccccc1>>O=C(OCc1ccccc1)[C@H](CO)NCc1ccccc1 | C(#N)[BH3-].[Na+].Cl.C(C1=CC=CC=C1)OC([C@@H](N)CO)=O.C(C1=CC=CC=C1)=O.C(C)(=O)[O-].[Na+]>>C(C1=CC=CC=C1)OC([C@@H](NCC1=CC=CC=C1)CO)=O | [O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[C@H:11]([CH2:12][OH:13])[NH2:14].O=[CH:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[C@H:11]([CH2:12][OH:13])[NH:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | N[C@@H](CO)C(=O)OCc1ccccc1.O=Cc1ccccc1 | O=C(OCc1ccccc1)[C@H](CO)NCc1ccccc1 | null | null | CO | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | O=C(CNCc1ccccc1)OCc1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[NH2;D1;+0:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11]>>[C:5]-[C:6](-[NH;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11] | 81 | [{"value": 81.0, "product": "C(C1=CC=CC=C1)OC([C@@H](NCC1=CC=CC=C1)CO)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | To a mixture of L-serine-benzyl ester-HCl (2.3 g), benzaldehyde(1.05 eq.) and sodium acetate (1 eq.) in methanol was added sodium cyanoborohydride (1.0 eq.). The resulting mixture was stirred at ambient temperature for 15 hrs, then partitioned into ether and aqueous saturated sodium bicarbonate. The separated organic p... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1 | Other | CO | null | 15 | N[C@@H](CO)C(=O)OCc1ccccc1.O=Cc1ccccc1>CO>O=C(OCc1ccccc1)[C@H](CO)NCc1ccccc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-77e443df8e2d403b81623c641b5e9394 | C=C(C)CBr.II.O=C(OCc1ccccc1)[C@H](CO)NCc1ccccc1>>CC1(CI)CN(Cc2ccccc2)C(C(=O)OCc2ccccc2)CO1 | C(C1=CC=CC=C1)OC([C@@H](NCC1=CC=CC=C1)CO)=O.C(C1=CC=CC=C1)OC([C@@H](NCC1=CC=CC=C1)CO)=O.BrCC(=C)C.C(=O)([O-])[O-].[K+].[K+].II.BrCC(=C)C>>C(C1=CC=CC=C1)OC(=O)C1N(CC(OC1)(C)CI)CC1=CC=CC=C1 | Br[CH2:3][C:2]([CH3:1])=[CH2:5].I[I:4].[NH:6]([CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[C@H:14]([C:15](=[O:16])[O:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)[CH2:25][OH:26]>>[CH3:1][C:2]1([CH2:3][I:4])[CH2:5][N:6]([CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[CH:14]([C:15](=[O:16])[O:17][CH2:18]... | C=C(C)CBr.II.O=C(OCc1ccccc1)[C@H](CO)NCc1ccccc1 | CC1(CI)CN(Cc2ccccc2)C(C(=O)OCc2ccccc2)CO1 | null | null | CC#N.CCOC(=O)C.CCCCCC | Heteroatom Alkylation and Arylation | OtherReaction | 7fdda7499cb691fc9e08dbb17c4964c805059d7ec826a851e5e7c3a7d1683064 | 2b3f9402e95e7d2bbee1f40b67bc1facac10e2ef69e32213d57db76c382e04d4 | O=C(OCc1ccccc1)C1COCCN1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](-[C;D1;H3:3])=[CH2;D1;+0:4].I-[I;H0;D1;+0:5].[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C@H;D3;+0:10](-[C:11]-[OH;D1;+0:12])-[NH;D2;+0:13]-[C:14]-[c:15]>>[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[CH;D3;+0:10]1-[C:11]-[O;H0;D2;+0:12]-[C;H0;D4;+0:2](-[C;D1;H3:3])(-[CH2;D2;+0:1]-[I;H0;D1;+0:5])-[CH2;D2;+0:4... | 64 | [{"value": 64.0, "product": "C(C1=CC=CC=C1)OC(=O)C1N(CC(OC1)(C)CI)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 72 | HOUR | To a solution of N-benzyl-serine benzyl ester (Intermediate 16, 6.35 g) in 90 ml of MeCN at ambient temperature was added 3-bromo-2-methyl-propene (5.6 ml), KI (740 mg) and K2CO3 (7.7 g). The reaction mixture was stirred at ambient temperature for 72 hrs. 1 ml of 3-bromo-2-methyl-propene was added and the reaction mixt... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol.Secondary amine.Vinyl | Primary halide.Ether.Tertiary amine | null | C1COCC[NH]1 | C1COCC[NH]1.c1ccccc1.c1ccccc1 | HBr.I- | CC#N.CCOC(=O)C.CCCCCC | null | 72 | C=C(C)CBr.II.O=C(OCc1ccccc1)[C@H](CO)NCc1ccccc1>CC#N.CCOC(=O)C.CCCCCC>CC1(CI)CN(Cc2ccccc2)C(C(=O)OCc2ccccc2)CO1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-de82173cc7804e4cae31af4e4fc9d489 | CC1(CI)CN(Cc2ccccc2)C(C(=O)OCc2ccccc2)CO1>>CC1(C)CN(Cc2ccccc2)C(C(=O)OCc2ccccc2)CO1 | C(C1=CC=CC=C1)OC(=O)C1N(CC(OC1)(C)CI)CC1=CC=CC=C1.C(C1=CC=CC=C1)OC(=O)C1N(CC(OC1)(C)CI)CC1=CC=CC=C1.C(CCC)[SnH](CCCC)CCCC.CC(C)(C#N)N=NC(C)(C)C#N>>C(C1=CC=CC=C1)OC(=O)C1N(CC(OC1)(C)C)CC1=CC=CC=C1 | I[CH2:3][C:2]1([CH3:1])[CH2:4][N:5]([CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[CH:13]([C:14](=[O:15])[O:16][CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[CH2:24][O:25]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][N:5]([CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[CH:13]([C:14](=[O:15])[O:16][CH2:17][c:18]2[cH:19][cH:... | CC1(CI)CN(Cc2ccccc2)C(C(=O)OCc2ccccc2)CO1 | CC1(C)CN(Cc2ccccc2)C(C(=O)OCc2ccccc2)CO1 | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | Dehalogenation | 72a5231b07f184f0ef4a0648badd4176f521b95f1ba3340a0f90d8894af47260 | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | O=C(OCc1ccccc1)C1COCCN1Cc1ccccc1 | I-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])(-[#8:4]-[C:5])-[C:6]-[#7:7]>>[#7:7]-[C:6]-[C:2](-[C;D1;H3:3])(-[CH3;D1;+0:1])-[#8:4]-[C:5] | 85 | [{"value": 85.0, "product": "C(C1=CC=CC=C1)OC(=O)C1N(CC(OC1)(C)C)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 4-benzyl-6-iodomethyl-6-methyl-morpholine-3-carboxylic acid benzyl ester (Intermediate 17, 1.23 g) and tributyltin hydride (1.8 ml, 2.5 eq.) in 11 ml of toluene under gentle reflux was added over 1.5 hr a solution of AIBN in toluene (25 mg/1 ml). The mixture was allowed to cool down and was concentrate... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | C1COCC[NH]1.c1ccccc1.c1ccccc1 | I- | C1(=CC=CC=C1)C | null | null | CC1(CI)CN(Cc2ccccc2)C(C(=O)OCc2ccccc2)CO1>C1(=CC=CC=C1)C>CC1(C)CN(Cc2ccccc2)C(C(=O)OCc2ccccc2)CO1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-d6731d9b8e144b0e9b60dee94349263b | CC1(C)CN(Cc2ccccc2)C(C(=O)OCc2ccccc2)CO1>>CC1(C)CNC(C(=O)O)CO1 | C(C1=CC=CC=C1)OC(=O)C1N(CC(OC1)(C)C)CC1=CC=CC=C1.C(C1=CC=CC=C1)OC(=O)C1N(CC(OC1)(C)C)CC1=CC=CC=C1>>CC1(OCC(NC1)C(=O)O)C | c1ccc(C[N:5]2[CH2:4][C:2]([CH3:1])([CH3:3])[O:11][CH2:10][CH:6]2[C:7](=[O:8])[O:9]Cc2ccccc2)cc1>>[CH3:1][C:2]1([CH3:3])[CH2:4][NH:5][CH:6]([C:7](=[O:8])[OH:9])[CH2:10][O:11]1 | CC1(C)CN(Cc2ccccc2)C(C(=O)OCc2ccccc2)CO1 | CC1(C)CNC(C(=O)O)CO1 | null | [OH-].[OH-].[Pd+2] | CC(=O)O.CO | Deprotection | OtherReaction | fd133f20ece8af39de6ac98d2595c0684237870ac067b15eea0f5f441e9a4923 | 3d8e4bece6e5ac07ee91a76d9cf0561ba741378ef06008fae89f75f1d764c0c9 | C1COCCN1 | [O;D1;H0:1]=[C:2](-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1)-[C:4]1-[C:5]-[#8:6]-[C:7]-[C:8]-[N;H0;D3;+0:9]-1-C-c1:c:c:c:c:c:1>>[O;D1;H0:1]=[C:2](-[OH;D1;+0:3])-[C:4]1-[C:5]-[#8:6]-[C:7]-[C:8]-[NH;D2;+0:9]-1 | 95.4 | [{"value": 95.0, "product": "CC1(OCC(NC1)C(=O)O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.4, "product": "CC1(OCC(NC1)C(=O)O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 72 | HOUR | To a solution of 4-benzyl-6,6-dimethyl-morpholine-3-carboxylic acid benzyl ester (Intermediate 18, 1.25 g) in 40 ml of 10% AcOH/MeOH (under nitrogen) was added 250 mg of 20% Pd(OH)2 on charcoal. The reaction mixture was purged with hydrogen (balloon) and was stirred at ambient temperature for 72 hrs. To the resulting g... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Tertiary amine | Carboxylic acid.Secondary amine | c1ccccc1.C1COCC[NH]1.c1ccccc1 | C1COCCN1 | C1COCCN1 | Other | [OH-].[OH-].[Pd+2].CC(=O)O.CO | null | 72 | CC1(C)CN(Cc2ccccc2)C(C(=O)OCc2ccccc2)CO1>[OH-].[OH-].[Pd+2].CC(=O)O.CO>CC1(C)CNC(C(=O)O)CO1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-922f4d1b3fc74bca99bd38351a87de4c | C=O.CC1(C)CNC(C(=O)O)CO1>>CN1CC(C)(C)OCC1C(=O)O | C=O.CC1(OCC(NC1)C(=O)O)C.CC1(OCC(NC1)C(=O)O)C>>CN1C(COC(C1)(C)C)C(=O)O | O=[CH2:1].[NH:2]1[CH2:3][C:4]([CH3:5])([CH3:6])[O:7][CH2:8][CH:9]1[C:10](=[O:11])[OH:12]>>[CH3:1][N:2]1[CH2:3][C:4]([CH3:5])([CH3:6])[O:7][CH2:8][CH:9]1[C:10](=[O:11])[OH:12] | C=O.CC1(C)CNC(C(=O)O)CO1 | CN1CC(C)(C)OCC1C(=O)O | null | [Pd] | C(C)O | Heteroatom Alkylation and Arylation | Eschweiler-Clarke Secondary Amine Methylation | fdddc65917853749f4468b50c6d27df95b134f4ca23d77fbc7927a814b9768f6 | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | C1COCCN1 | O=[CH2;D1;+0:1].[O;D1;H0:2]=[C:3](-[O;D1;H1:4])-[C:5]1-[C:6]-[#8:7]-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[CH3;D1;+0:1]-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#8:7]-[C:6]-[C:5]-1-[C:3](=[O;D1;H0:2])-[O;D1;H1:4] | 97 | [{"value": 97.0, "product": "CN1C(COC(C1)(C)C)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | To a suspension of 6,6-dimethyl-morpholine-3-carboxylic acid (Intermediate 19, 540 mg) in 17 ml of ethanol (under nitrogen) was added 100 mg of 10% Pd on charcoal and 830 ul (˜3 eq.) of 37% aqueous formaldehyde. The mixture was purged with hydrogen (balloon) and stirred at ambient temperature for 5 hrs. To the resultin... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | C1COCCN1 | C1COCC[NH]1 | C1COCC[NH]1 | Other | [Pd].C(C)O | null | 5 | C=O.CC1(C)CNC(C(=O)O)CO1>[Pd].C(C)O>CN1CC(C)(C)OCC1C(=O)O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-7af62963344d437cb6f1e896ba44c546 | CN1CC(C)(C)OCC1C(=O)O.Nc1cc(Cl)cc2c1[nH]c1cnccc12>>CN1CC(C)(C)OCC1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 | ClC=1C=C2C=3C=CN=CC3NC2=C(C1)N.CN1C(COC(C1)(C)C)C(=O)O>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)C1N(CC(OC1)(C)C)C | O[C:10]([CH:9]1[N:2]([CH3:1])[CH2:3][C:4]([CH3:5])([CH3:6])[O:7][CH2:8]1)=[O:11].[NH2:12][c:13]1[cH:14][c:15]([Cl:16])[cH:17][c:18]2[c:19]1[nH:20][c:21]1[cH:22][n:23][cH:24][cH:25][c:26]21>>[CH3:1][N:2]1[CH2:3][C:4]([CH3:5])([CH3:6])[O:7][CH2:8][CH:9]1[C:10](=[O:11])[NH:12][c:13]1[cH:14][c:15]([Cl:16])[cH:17][c:18]2[c:... | CN1CC(C)(C)OCC1C(=O)O.Nc1cc(Cl)cc2c1[nH]c1cnccc12 | CN1CC(C)(C)OCC1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1cccc2c1[nH]c1cnccc12)C1COCCN1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4]-[#8:5])-[#7:6](-[C;D1;H3:7])-[C:8].[#7;a:9]:[c:10]:[c:11]:[#7;a:12]:[c:13](:[c:14]):[c:15](-[NH2;D1;+0:16]):[c:17]>>[#7;a:9]:[c:10]:[c:11]:[#7;a:12]:[c:13](:[c:14]):[c:15](-[NH;D2;+0:16]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4]-[#8:5])-[#7:6](-[C;D1;H3:7])-[C:8]):[c:17] | 61 | [{"value": 61.0, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)C1N(CC(OC1)(C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The desired compound was prepared according to Method B from 6-chloro-9H-β-carboline-8-ylamine and 4,6,6-trimethyl-morpholine-3-carboxylic acid in 61% yield.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1COCC[NH]1.c1ccc2c(c1)[nH]c1cnccc12 | HO- | null | null | null | CN1CC(C)(C)OCC1C(=O)O.Nc1cc(Cl)cc2c1[nH]c1cnccc12>>CN1CC(C)(C)OCC1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-652727651c6a4c0ca4ce9fbe27907fd7 | O=[N+]([O-])c1c(F)c(Cl)cc2c1[nH]c1cnccc12.OCC1CC1>>O=[N+]([O-])c1c(OCC2CC2)c(Cl)cc2c1[nH]c1cnccc12 | O.C1(CC1)CO.[H-].[Na+].ClC=1C=C2C=3C=CN=CC3NC2=C(C1F)[N+](=O)[O-]>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1OCC1CC1)[N+](=O)[O-] | F[c:5]1[c:4]([N+:2](=[O:1])[O-:3])[c:15]2[c:14]([cH:13][c:11]1[Cl:12])[c:22]1[c:17]([nH:16]2)[cH:18][n:19][cH:20][cH:21]1.[OH:6][CH2:7][CH:8]1[CH2:9][CH2:10]1>>[O:1]=[N+:2]([O-:3])[c:4]1[c:5]([O:6][CH2:7][CH:8]2[CH2:9][CH2:10]2)[c:11]([Cl:12])[cH:13][c:14]2[c:15]1[nH:16][c:17]1[cH:18][n:19][cH:20][cH:21][c:22]21 | O=[N+]([O-])c1c(F)c(Cl)cc2c1[nH]c1cnccc12.OCC1CC1 | O=[N+]([O-])c1c(OCC2CC2)c(Cl)cc2c1[nH]c1cnccc12 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | eb9f6ceb14d04281e24cbf4d6354ca29ee2394b373406b20c365e94506dd7cee | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1cc2c(cn1)[nH]c1cc(OCC3CC3)ccc12 | F-[c;H0;D3;+0:1]1:[c:2](-[Cl;D1;H0:3]):[c:4]:[c:5]:[c:6](:[#7;a:7]:[c:8]:[c:9]:[#7;a:10]):[c:11]:1-[#7;+:12].[C:13]-[C:14]-[OH;D1;+0:15]>>[#7;+:12]-[c:11]1:[c:6](:[#7;a:7]:[c:8]:[c:9]:[#7;a:10]):[c:5]:[c:4]:[c:2](-[Cl;D1;H0:3]):[c;H0;D3;+0:1]:1-[O;H0;D2;+0:15]-[C:14]-[C:13] | 85 | [{"value": 85.0, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1OCC1CC1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.5, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1OCC1CC1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | Cyclopropylmethyl alcohol (0.921 ml, 11.4 mmol) was added to a stirring suspension of NaH (455 mg, 11.4 mmol) in DMF (20 ml) under an argon atmosphere. The resulting solution was allowed to stir at RT for 20 min. 6-chloro-7-fluoro-8-nitro-9H-β-carboline (500 mg, 1.9 mmol) was added to the stirring solution and the resu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccc2c(c1)[nH]c1cnccc12 | c1ccc2c(c1)[nH]c1cnccc12 | C1CC1.c1ccc2c(c1)[nH]c1cnccc12 | HF | CN(C)C=O | null | 0.333333 | O=[N+]([O-])c1c(F)c(Cl)cc2c1[nH]c1cnccc12.OCC1CC1>CN(C)C=O>O=[N+]([O-])c1c(OCC2CC2)c(Cl)cc2c1[nH]c1cnccc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-f36f8b53201943fe85c6b7396fde7d0e | O=[N+]([O-])c1c(OCC2CC2)c(Cl)cc2c1[nH]c1cnccc12>>Nc1c(OCC2CC2)c(Cl)cc2c1[nH]c1cnccc12 | ClC=1C=C2C=3C=CN=CC3NC2=C(C1OCC1CC1)[N+](=O)[O-].[H][H].C(=O)(O)[O-].[Na+]>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1OCC1CC1)N | O=[N+:1]([O-])[c:2]1[c:3]([O:4][CH2:5][CH:6]2[CH2:7][CH2:8]2)[c:9]([Cl:10])[cH:11][c:12]2[c:13]1[nH:14][c:15]1[cH:16][n:17][cH:18][cH:19][c:20]21>>[NH2:1][c:2]1[c:3]([O:4][CH2:5][CH:6]2[CH2:7][CH2:8]2)[c:9]([Cl:10])[cH:11][c:12]2[c:13]1[nH:14][c:15]1[cH:16][n:17][cH:18][cH:19][c:20]21 | O=[N+]([O-])c1c(OCC2CC2)c(Cl)cc2c1[nH]c1cnccc12 | Nc1c(OCC2CC2)c(Cl)cc2c1[nH]c1cnccc12 | null | [Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1cc2c(cn1)[nH]c1cc(OCC3CC3)ccc12 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]:[c:8]:[#7;a:9]>>[#7;a:9]:[c:8]:[c:7]:[#7;a:6]:[c:4](:[c:5]):[c:2](-[NH2;D1;+0:1]):[c:3] | 80.1 | [{"value": 80.0, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1OCC1CC1)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.1, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1OCC1CC1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 6-chloro-7-cyclopropylmethoxy-8-nitro-9H-β-carboline (510 mg, 1.61 mmol) was suspended in 12 ml of methanol and 100 mg of Pd/C(10%) was added. The flask was fitted with a balloon of hydrogen and the reaction mixture was stirred overnight at RT. Upon filtration through a pad of celite and evaporation of the methanol, a ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | C1CC1.c1ccc2c(c1)[nH]c1cnccc12 | Other | [Pd].CO | null | 8 | O=[N+]([O-])c1c(OCC2CC2)c(Cl)cc2c1[nH]c1cnccc12>[Pd].CO>Nc1c(OCC2CC2)c(Cl)cc2c1[nH]c1cnccc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-970f2d8f6a31410c9eb7931d5d8ac635 | Cc1ncccc1C(=O)O.Nc1c(OCC2CC2)c(Cl)cc2c1[nH]c1cnccc12>>Cc1ncccc1C(=O)Nc1c(OCC2CC2)c(Cl)cc2c1[nH]c1cnccc12 | ClC=1C=C2C=3C=CN=CC3NC2=C(C1OCC1CC1)N.CC1=C(C(=O)O)C=CC=N1>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1OCC1CC1)NC(C1=C(N=CC=C1)C)=O | O[C:8]([c:7]1[c:2]([CH3:1])[n:3][cH:4][cH:5][cH:6]1)=[O:9].[NH2:10][c:11]1[c:12]([O:13][CH2:14][CH:15]2[CH2:16][CH2:17]2)[c:18]([Cl:19])[cH:20][c:21]2[c:22]1[nH:23][c:24]1[cH:25][n:26][cH:27][cH:28][c:29]21>>[CH3:1][c:2]1[n:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[NH:10][c:11]1[c:12]([O:13][CH2:14][CH:15]2[CH2:16][CH2:1... | Cc1ncccc1C(=O)O.Nc1c(OCC2CC2)c(Cl)cc2c1[nH]c1cnccc12 | Cc1ncccc1C(=O)Nc1c(OCC2CC2)c(Cl)cc2c1[nH]c1cnccc12 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1c(OCC2CC2)ccc2c1[nH]c1cnccc12)c1cccnc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[C;D1;H3:6]):[#7;a:7]:[c:8].[#7;a:9]:[c:10]:[c:11]:[#7;a:12]:[c:13](:[c:14]):[c:15](-[NH2;D1;+0:16]):[c:17]>>[#7;a:9]:[c:10]:[c:11]:[#7;a:12]:[c:13](:[c:14]):[c:15](-[NH;D2;+0:16]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[C;D1;H3:6]):[#7;a:7]:[c:8]):[c:17] | 40 | [{"value": 40.0, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1OCC1CC1)NC(C1=C(N=CC=C1)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The desired compound was prepared according to Method A from 6-chloro-7-cyclopropylmethoxy-9H-β-carbolin-8-ylamine and 2-methylnicotinic acid in a 40-60% yield.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccncc1.C1CC1.c1ccc2c(c1)[nH]c1cnccc12 | HO- | null | null | null | Cc1ncccc1C(=O)O.Nc1c(OCC2CC2)c(Cl)cc2c1[nH]c1cnccc12>>Cc1ncccc1C(=O)Nc1c(OCC2CC2)c(Cl)cc2c1[nH]c1cnccc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-4fd2ab0b382a4a5fafaa30220b5f686c | O=[N+]([O-])c1c(F)c(Cl)cc2c1[nH]c1cnccc12>>Nc1c(F)c(Cl)cc2c1[nH]c1cnccc12 | ClC=1C=C2C=3C=CN=CC3NC2=C(C1F)[N+](=O)[O-]>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1F)N | O=[N+:1]([O-])[c:2]1[c:3]([F:4])[c:5]([Cl:6])[cH:7][c:8]2[c:9]1[nH:10][c:11]1[cH:12][n:13][cH:14][cH:15][c:16]21>>[NH2:1][c:2]1[c:3]([F:4])[c:5]([Cl:6])[cH:7][c:8]2[c:9]1[nH:10][c:11]1[cH:12][n:13][cH:14][cH:15][c:16]21 | O=[N+]([O-])c1c(F)c(Cl)cc2c1[nH]c1cnccc12 | Nc1c(F)c(Cl)cc2c1[nH]c1cnccc12 | null | [Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2c(c1)[nH]c1cnccc12 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]:[c:8]:[#7;a:9]>>[#7;a:9]:[c:8]:[c:7]:[#7;a:6]:[c:4](:[c:5]):[c:2](-[NH2;D1;+0:1]):[c:3] | 90.3 | [{"value": 90.3, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1F)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | A slurry of 6-chloro-7-fluoro-8-nitro-9H-β-carboline (500 mg, 1.88 mmol) in MeOH (25 ml) was degassed with argon. Palladium on charcoal (20% w/w on C, 50 mg) was added and the reaction vessel was flushed with hydrogen. The slurry was stirred under a balloon of hydrogen for 6 hr, then filtered through celite and concent... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2c(c1)[nH]c1cnccc12 | Other | [Pd].CO | null | 6 | O=[N+]([O-])c1c(F)c(Cl)cc2c1[nH]c1cnccc12>[Pd].CO>Nc1c(F)c(Cl)cc2c1[nH]c1cnccc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-212676db6bac4ade867f66bfad747cd6 | Cc1ncccc1C(=O)O.Nc1c(F)c(Cl)cc2c1[nH]c1cnccc12>>Cc1ncccc1C(=O)Nc1c(F)c(Cl)cc2c1[nH]c1cnccc12 | C1=CC(=NN=C1NN)N(CCO)CCO.Cl.Cl.CC1=C(C(=O)O)C=CC=N1.ClC=1C=C2C=3C=CN=CC3NC2=C(C1F)N.CCN=C=NCCCN(C)C>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1F)NC(C1=C(N=CC=C1)C)=O | O[C:8]([c:7]1[c:2]([CH3:1])[n:3][cH:4][cH:5][cH:6]1)=[O:9].[NH2:10][c:11]1[c:12]([F:13])[c:14]([Cl:15])[cH:16][c:17]2[c:18]1[nH:19][c:20]1[cH:21][n:22][cH:23][cH:24][c:25]21>>[CH3:1][c:2]1[n:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[NH:10][c:11]1[c:12]([F:13])[c:14]([Cl:15])[cH:16][c:17]2[c:18]1[nH:19][c:20]1[cH:21][n:22... | Cc1ncccc1C(=O)O.Nc1c(F)c(Cl)cc2c1[nH]c1cnccc12 | Cc1ncccc1C(=O)Nc1c(F)c(Cl)cc2c1[nH]c1cnccc12 | null | null | N1=CC=CC=C1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1cccc2c1[nH]c1cnccc12)c1cccnc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[C;D1;H3:6]):[#7;a:7]:[c:8].[#7;a:9]:[c:10]:[c:11]:[#7;a:12]:[c:13](:[c:14]):[c:15](-[NH2;D1;+0:16]):[c:17]>>[#7;a:9]:[c:10]:[c:11]:[#7;a:12]:[c:13](:[c:14]):[c:15](-[NH;D2;+0:16]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[C;D1;H3:6]):[#7;a:7]:[c:8]):[c:17] | null | [] | 100 | CELSIUS | null | null | A solution of 6-chloro-7-fluoro-9H-β-carbolin-8-ylamine (100 mg, 0.424 mmol) in pyridine (2.5 ml) was stirred at RT. 2-methyl nicotinic acid (70 mg, 0.509 mmol) was added, followed by EDCI (130 mg, 0.678 mmol). The suspension was stirred at 100° C. for a day. The pyridine was removed under reduced pressure and the resu... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccc2c(c1)[nH]c1cnccc12 | HO- | N1=CC=CC=C1 | 100 | null | Cc1ncccc1C(=O)O.Nc1c(F)c(Cl)cc2c1[nH]c1cnccc12>N1=CC=CC=C1>Cc1ncccc1C(=O)Nc1c(F)c(Cl)cc2c1[nH]c1cnccc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-831366161355451eb87675e81341adfa | C[S-].O=[N+]([O-])c1c(F)c(Cl)cc2c1[nH]c1cnccc12>>CSc1c(Cl)cc2c([nH]c3cnccc32)c1[N+](=O)[O-] | ClC=1C=C2C=3C=CN=CC3NC2=C(C1F)[N+](=O)[O-].ClC=1C=C2C=3C=CN=CC3NC2=C(C1F)[N+](=O)[O-].CN(C)C=O.C[S-].[Na+]>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1SC)[N+](=O)[O-] | [CH3:1][S-:2].F[c:3]1[c:4]([Cl:5])[cH:6][c:7]2[c:8]([nH:9][c:10]3[cH:11][n:12][cH:13][cH:14][c:15]23)[c:16]1[N+:17](=[O:18])[O-:19]>>[CH3:1][S:2][c:3]1[c:4]([Cl:5])[cH:6][c:7]2[c:8]([nH:9][c:10]3[cH:11][n:12][cH:13][cH:14][c:15]23)[c:16]1[N+:17](=[O:18])[O-:19] | C[S-].O=[N+]([O-])c1c(F)c(Cl)cc2c1[nH]c1cnccc12 | CSc1c(Cl)cc2c([nH]c3cnccc32)c1[N+](=O)[O-] | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 278a1f60937c998ec02609c16c07f994a421fa5a3ed90fcfbeacdee2ebaa3bd2 | 1813ae14fbd9cacead4dcfaf9efbd2467a19b3e216836766b78aa6647dcfb48a | c1ccc2c(c1)[nH]c1cnccc12 | F-[c;H0;D3;+0:1]1:[c:2](-[#7;+:3]):[c:4](:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]):[c:9]:[c:10]:[c:11]:1-[Cl;D1;H0:12].[C;D1;H3:13]-[S-;H0;D1:14]>>[#7;+:3]-[c:2]1:[c:4](:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]):[c:9]:[c:10]:[c:11](-[Cl;D1;H0:12]):[c;H0;D3;+0:1]:1-[S;H0;D2;+0:14]-[C;D1;H3:13] | 91.8 | [{"value": 91.8, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1SC)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | A 250 ml round-bottom flask with magnetic stirrer was charged with 6-chloro-7-fluoro-8-nitro-β-carboline (Intermediate 5, 3.959 g, 14.9 mmol) and 100 ml anhydrous DMF. The resulting orange mixture was cooled to 0° C. (ice and water bath) and sodium thiomethoxide (1.809 g, 25.8 mmol) in powder form was added slowly ther... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Monosulfide | c1ccc2c(c1)[nH]c1cnccc12 | c1ccc2c(c1)[nH]c1cnccc12 | c1ccc2c(c1)[nH]c1cnccc12 | Other | O | 0 | 1 | C[S-].O=[N+]([O-])c1c(F)c(Cl)cc2c1[nH]c1cnccc12>O>CSc1c(Cl)cc2c([nH]c3cnccc32)c1[N+](=O)[O-] |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-fe7796a45668470a88b977caac4dbba7 | CSc1c(Cl)cc2c([nH]c3cnccc32)c1N.Cc1ncccc1C(=O)O>>CSc1c(Cl)cc2c([nH]c3cnccc32)c1NC(=O)c1cccnc1C | Cl.CN(CCCN=C=NCC)C.ClC=1C=C2C=3C=CN=CC3NC2=C(C1SC)N.ClC=1C=C2C=3C=CN=CC3NC2=C(C1SC)N.CC1=C(C(=O)O)C=CC=N1.O>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1SC)NC(C1=C(N=CC=C1)C)=O | [CH3:1][S:2][c:3]1[c:4]([Cl:5])[cH:6][c:7]2[c:8]([nH:9][c:10]3[cH:11][n:12][cH:13][cH:14][c:15]23)[c:16]1[NH2:17].O[C:18](=[O:19])[c:20]1[cH:21][cH:22][cH:23][n:24][c:25]1[CH3:26]>>[CH3:1][S:2][c:3]1[c:4]([Cl:5])[cH:6][c:7]2[c:8]([nH:9][c:10]3[cH:11][n:12][cH:13][cH:14][c:15]23)[c:16]1[NH:17][C:18](=[O:19])[c:20]1[cH:2... | CSc1c(Cl)cc2c([nH]c3cnccc32)c1N.Cc1ncccc1C(=O)O | CSc1c(Cl)cc2c([nH]c3cnccc32)c1NC(=O)c1cccnc1C | null | null | CO.N1=CC=CC=C1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1cccc2c1[nH]c1cnccc12)c1cccnc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[C;D1;H3:6]):[#7;a:7]:[c:8].[#7;a:9]:[c:10]:[c:11]:[#7;a:12]:[c:13](:[c:14]):[c:15](-[NH2;D1;+0:16]):[c:17]>>[#7;a:9]:[c:10]:[c:11]:[#7;a:12]:[c:13](:[c:14]):[c:15](-[NH;D2;+0:16]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[C;D1;H3:6]):[#7;a:7]:[c:8]):[c:17] | 89.5 | [{"value": 89.5, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1SC)NC(C1=C(N=CC=C1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 18 | HOUR | A 250 ml round-bottom flask with magnetic stirrer was charged with 6-chloro-7-methylsulfanyl-9H-β-carbolin-8-ylamine (Intermediate 28, 2.336 g, 8.86 mmol) and 2-methylnicotinic acid (3.219 g, 23.4 mmol) in 80 ml anhydrous pyridine. To the resulting reaction mixture at RT was added solid 1-(3-dimethylaminopropyl)-3-ethy... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2c(c1)[nH]c1cnccc12.c1ccncc1 | HO- | CO.N1=CC=CC=C1 | 100 | 18 | CSc1c(Cl)cc2c([nH]c3cnccc32)c1N.Cc1ncccc1C(=O)O>CO.N1=CC=CC=C1>CSc1c(Cl)cc2c([nH]c3cnccc32)c1NC(=O)c1cccnc1C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-e3ed8d18dc2b4a6db03c647fd794b654 | CC[S-].O=[N+]([O-])c1c(F)c(Cl)cc2c1[nH]c1cnccc12>>CCSc1c(Cl)cc2c([nH]c3cnccc32)c1[N+](=O)[O-] | ClC=1C=C2C=3C=CN=CC3NC2=C(C1F)[N+](=O)[O-].[S-]CC.[Na+].O>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1SCC)[N+](=O)[O-] | [CH3:1][CH2:2][S-:3].F[c:4]1[c:5]([Cl:6])[cH:7][c:8]2[c:9]([nH:10][c:11]3[cH:12][n:13][cH:14][cH:15][c:16]23)[c:17]1[N+:18](=[O:19])[O-:20]>>[CH3:1][CH2:2][S:3][c:4]1[c:5]([Cl:6])[cH:7][c:8]2[c:9]([nH:10][c:11]3[cH:12][n:13][cH:14][cH:15][c:16]23)[c:17]1[N+:18](=[O:19])[O-:20] | CC[S-].O=[N+]([O-])c1c(F)c(Cl)cc2c1[nH]c1cnccc12 | CCSc1c(Cl)cc2c([nH]c3cnccc32)c1[N+](=O)[O-] | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 278a1f60937c998ec02609c16c07f994a421fa5a3ed90fcfbeacdee2ebaa3bd2 | 1813ae14fbd9cacead4dcfaf9efbd2467a19b3e216836766b78aa6647dcfb48a | c1ccc2c(c1)[nH]c1cnccc12 | F-[c;H0;D3;+0:1]1:[c:2](-[#7;+:3]):[c:4](:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]):[c:9]:[c:10]:[c:11]:1-[Cl;D1;H0:12].[C;D1;H3:13]-[C:14]-[S-;H0;D1:15]>>[#7;+:3]-[c:2]1:[c:4](:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]):[c:9]:[c:10]:[c:11](-[Cl;D1;H0:12]):[c;H0;D3;+0:1]:1-[S;H0;D2;+0:15]-[C:14]-[C;D1;H3:13] | 81.2 | [{"value": 79.0, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1SCC)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.2, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1SCC)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 45 | MINUTE | A 25 ml round-bottom flask with a magnetic stirrer was charged with 6-chloro-7-fluoro-8-nitro-9H-β-carboline (102 mg, 0.38 mmol) in 5 ml of anhydrous DMF. To the resulting orange mixture at RT was slowly added sodium thioethoxide (80% pure, 69.7 mg, 0.66 mmol) in powder form. The reaction mixture was stirred at RT for ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Monosulfide | c1ccc2c(c1)[nH]c1cnccc12 | c1ccc2c(c1)[nH]c1cnccc12 | c1ccc2c(c1)[nH]c1cnccc12 | Other | CN(C)C=O | null | 0.75 | CC[S-].O=[N+]([O-])c1c(F)c(Cl)cc2c1[nH]c1cnccc12>CN(C)C=O>CCSc1c(Cl)cc2c([nH]c3cnccc32)c1[N+](=O)[O-] |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-99de42632e8e4623a5dd2ee602d10fb0 | CCSc1c(Cl)cc2c([nH]c3cnccc32)c1[N+](=O)[O-]>>CCSc1c(Cl)cc2c([nH]c3cnccc32)c1N | C.ClC=1C=C2C=3C=CN=CC3NC2=C(C1SCC)[N+](=O)[O-].[Cl-].[NH4+]>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1SCC)N | O=[N+:18]([O-])[c:17]1[c:4]([S:3][CH2:2][CH3:1])[c:5]([Cl:6])[cH:7][c:8]2[c:9]1[nH:10][c:11]1[cH:12][n:13][cH:14][cH:15][c:16]21>>[CH3:1][CH2:2][S:3][c:4]1[c:5]([Cl:6])[cH:7][c:8]2[c:9]([nH:10][c:11]3[cH:12][n:13][cH:14][cH:15][c:16]23)[c:17]1[NH2:18] | CCSc1c(Cl)cc2c([nH]c3cnccc32)c1[N+](=O)[O-] | CCSc1c(Cl)cc2c([nH]c3cnccc32)c1N | null | [Fe] | C(C)(=O)OCC.C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2c(c1)[nH]c1cnccc12 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]:[c:8]:[#7;a:9]>>[#7;a:9]:[c:8]:[c:7]:[#7;a:6]:[c:4](:[c:5]):[c:2](-[NH2;D1;+0:1]):[c:3] | 100 | [{"value": 99.0, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1SCC)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.0, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1SCC)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 20 | HOUR | A 50 ml round-bottom flask with magnetic stirrer was charged with 6-chloro-7-ethylsulfanyl-8-nitro-9H-β-carboline (85.0 mg, 0.28 mmol) in 10 ml anhydrous ethanol. To the resulting orange mixture at RT was added 0.33 M aqueous ammonium chloride (2.0 ml, 0.66 mmol) and iron powder (680 mg, 12.2 mmol). The reaction mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2c(c1)[nH]c1cnccc12 | Other | [Fe].C(C)(=O)OCC.C(C)O | 60 | 20 | CCSc1c(Cl)cc2c([nH]c3cnccc32)c1[N+](=O)[O-]>[Fe].C(C)(=O)OCC.C(C)O>CCSc1c(Cl)cc2c([nH]c3cnccc32)c1N |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-44615147f6f746779af7e52873f60a22 | CCSc1c(Cl)cc2c([nH]c3cnccc32)c1N.Cc1ncccc1C(=O)O>>CCSc1c(Cl)cc2c([nH]c3cnccc32)c1NC(=O)c1cccnc1C | O.ClC=1C=C2C=3C=CN=CC3NC2=C(C1SCC)N.CC1=C(C(=O)O)C=CC=N1.Cl.CN(CCCN=C=NCC)C>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1SCC)NC(C1=C(N=CC=C1)C)=O | [CH3:1][CH2:2][S:3][c:4]1[c:5]([Cl:6])[cH:7][c:8]2[c:9]([nH:10][c:11]3[cH:12][n:13][cH:14][cH:15][c:16]23)[c:17]1[NH2:18].O[C:19](=[O:20])[c:21]1[cH:22][cH:23][cH:24][n:25][c:26]1[CH3:27]>>[CH3:1][CH2:2][S:3][c:4]1[c:5]([Cl:6])[cH:7][c:8]2[c:9]([nH:10][c:11]3[cH:12][n:13][cH:14][cH:15][c:16]23)[c:17]1[NH:18][C:19](=[O:... | CCSc1c(Cl)cc2c([nH]c3cnccc32)c1N.Cc1ncccc1C(=O)O | CCSc1c(Cl)cc2c([nH]c3cnccc32)c1NC(=O)c1cccnc1C | null | null | CO.N1=CC=CC=C1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1cccc2c1[nH]c1cnccc12)c1cccnc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[C;D1;H3:6]):[#7;a:7]:[c:8].[#7;a:9]:[c:10]:[c:11]:[#7;a:12]:[c:13](:[c:14]):[c:15](-[NH2;D1;+0:16]):[c:17]>>[#7;a:9]:[c:10]:[c:11]:[#7;a:12]:[c:13](:[c:14]):[c:15](-[NH;D2;+0:16]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[C;D1;H3:6]):[#7;a:7]:[c:8]):[c:17] | 40.7 | [{"value": 38.0, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1SCC)NC(C1=C(N=CC=C1)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.7, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1SCC)NC(C1=C(N=CC=C1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 2.5 | HOUR | A 25 ml round-bottom flask with magnetic stirrer was charged with 6-chloro-7-ethylsulfanyl-9H-β-carbolin-8-ylamine (37.2 mg, 0.13 mmol) and 2-methylnicotinic acid (36.2 mg, 0.26 mmol) in 3 ml anhydrous pyridine. To the resulting light-orange mixture at RT was added solid 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hy... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2c(c1)[nH]c1cnccc12.c1ccncc1 | HO- | CO.N1=CC=CC=C1 | 80 | 2.5 | CCSc1c(Cl)cc2c([nH]c3cnccc32)c1N.Cc1ncccc1C(=O)O>CO.N1=CC=CC=C1>CCSc1c(Cl)cc2c([nH]c3cnccc32)c1NC(=O)c1cccnc1C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-bc514ad0e3e84d83be2220180f062766 | CN(C)CCS.O=[N+]([O-])c1c(F)c(Cl)cc2c1[nH]c1cnccc12>>CN(C)CCSc1c(Cl)cc2c([nH]c3cnccc32)c1[N+](=O)[O-] | C(CCC)[Li].O.Cl.CN(CCS)C.ClC=1C=C2C=3C=CN=CC3NC2=C(C1F)[N+](=O)[O-].ClC=1C=C2C=3C=CN=CC3NC2=C(C1F)[N+](=O)[O-]>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1SCCN(C)C)[N+](=O)[O-] | [CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][SH:6].F[c:7]1[c:8]([Cl:9])[cH:10][c:11]2[c:12]([nH:13][c:14]3[cH:15][n:16][cH:17][cH:18][c:19]23)[c:20]1[N+:21](=[O:22])[O-:23]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][S:6][c:7]1[c:8]([Cl:9])[cH:10][c:11]2[c:12]([nH:13][c:14]3[cH:15][n:16][cH:17][cH:18][c:19]23)[c:20]1[N+:21](=[O:22])[O... | CN(C)CCS.O=[N+]([O-])c1c(F)c(Cl)cc2c1[nH]c1cnccc12 | CN(C)CCSc1c(Cl)cc2c([nH]c3cnccc32)c1[N+](=O)[O-] | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 3da7ce1aea3b8504c3ad35910fac5c4b5425645a60840f47f11ee73ab00296e4 | b7fe376f7aad2517725eef26ab981e4baa6c31c5f38fdf89e7c52a4a2c6cc1d2 | c1ccc2c(c1)[nH]c1cnccc12 | F-[c;H0;D3;+0:1]1:[c:2](-[#7;+:3]):[c:4](:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]):[c:9]:[c:10]:[c:11]:1-[Cl;D1;H0:12].[C:13]-[C:14]-[SH;D1;+0:15]>>[#7;+:3]-[c:2]1:[c:4](:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]):[c:9]:[c:10]:[c:11](-[Cl;D1;H0:12]):[c;H0;D3;+0:1]:1-[S;H0;D2;+0:15]-[C:14]-[C:13] | 84 | [{"value": 83.0, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1SCCN(C)C)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.0, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1SCCN(C)C)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | A 25 ml round-bottom flask with magnetic stirrer was charged with 6-chloro-7-fluoro-8-nitro-9H-β-carboline (98 mg, 0.37 mmol) in 2 ml of anhydrous DMF. A second 10 ml round-bottom flask with magnetic stirrer was charged with 2-dimethylamino-ethanethiol hydrochloride (100 mg, 0.70 mmol) in 2 ml anhydrous DMF. To the res... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aliphatic thiol | Monosulfide | c1ccc2c(c1)[nH]c1cnccc12 | c1ccc2c(c1)[nH]c1cnccc12 | c1ccc2c(c1)[nH]c1cnccc12 | HF | CN(C)C=O | null | 0.083333 | CN(C)CCS.O=[N+]([O-])c1c(F)c(Cl)cc2c1[nH]c1cnccc12>CN(C)C=O>CN(C)CCSc1c(Cl)cc2c([nH]c3cnccc32)c1[N+](=O)[O-] |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-6cee690533f34e0b838930aeaf183eee | CN(C)CCSc1c(Cl)cc2c([nH]c3cnccc32)c1[N+](=O)[O-]>>CN(C)CCSc1c(Cl)cc2c([nH]c3cnccc32)c1N | C.ClC=1C=C2C=3C=CN=CC3NC2=C(C1SCCN(C)C)[N+](=O)[O-].[Cl-].[NH4+]>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1SCCN(C)C)N | O=[N+:21]([O-])[c:20]1[c:7]([S:6][CH2:5][CH2:4][N:2]([CH3:1])[CH3:3])[c:8]([Cl:9])[cH:10][c:11]2[c:12]1[nH:13][c:14]1[cH:15][n:16][cH:17][cH:18][c:19]21>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][S:6][c:7]1[c:8]([Cl:9])[cH:10][c:11]2[c:12]([nH:13][c:14]3[cH:15][n:16][cH:17][cH:18][c:19]23)[c:20]1[NH2:21] | CN(C)CCSc1c(Cl)cc2c([nH]c3cnccc32)c1[N+](=O)[O-] | CN(C)CCSc1c(Cl)cc2c([nH]c3cnccc32)c1N | null | [Fe] | C(C)(=O)OCC.C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2c(c1)[nH]c1cnccc12 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]:[c:8]:[#7;a:9]>>[#7;a:9]:[c:8]:[c:7]:[#7;a:6]:[c:4](:[c:5]):[c:2](-[NH2;D1;+0:1]):[c:3] | 107 | [{"value": 107.0, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1SCCN(C)C)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 20 | HOUR | A 50 ml round-bottom flask with a magnetic stirrer was charged with [2-(6-chloro-8-nitro-9H-β-carbolin-7-ylsulfanyl)-ethyl]-dimethyl-amine (106 mg, 0.30 mmol) in 8 ml of anhydrous ethanol. To the resulting orange mixture at RT was added 0.33 M aqueous ammonium chloride (1.95 ml, 0.64 mmol) and iron powder (540 mg, 9.67... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2c(c1)[nH]c1cnccc12 | Other | [Fe].C(C)(=O)OCC.C(C)O | 60 | 20 | CN(C)CCSc1c(Cl)cc2c([nH]c3cnccc32)c1[N+](=O)[O-]>[Fe].C(C)(=O)OCC.C(C)O>CN(C)CCSc1c(Cl)cc2c([nH]c3cnccc32)c1N |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-3ffd78dd4f844473bdb2ea6319713d8b | C=O.Nc1cc(Cl)cc2c1[nH]c1cnccc12.O=C(O)[C@@H]1COCCN1>>CN1CCOC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 | ClC=1C=C2C=3C=CN=CC3NC2=C(C1)N.[H][H].[H][H].CCN=C=NCCCN(C)C.C=O.N1[C@@H](COCC1)C(=O)O>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)[C@H]1N(CCOC1)C | O=[CH2:1].[NH2:10][c:11]1[cH:12][c:13]([Cl:14])[cH:15][c:16]2[c:17]1[nH:18][c:19]1[cH:20][n:21][cH:22][cH:23][c:24]21.O[C:8]([C@H:7]1[NH:2][CH2:3][CH2:4][O:5][CH2:6]1)=[O:9]>>[CH3:1][N:2]1[CH2:3][CH2:4][O:5][CH2:6][C@H:7]1[C:8](=[O:9])[NH:10][c:11]1[cH:12][c:13]([Cl:14])[cH:15][c:16]2[c:17]1[nH:18][c:19]1[cH:20][n:21][... | C=O.Nc1cc(Cl)cc2c1[nH]c1cnccc12.O=C(O)[C@@H]1COCCN1 | CN1CCOC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 | null | [OH-].[OH-].[Pd+2] | CCOC(=O)C.O.CCO.N1=CC=CC=C1 | Acylation | OtherReaction | 1140aa8e8a72239787370cdb74da1e146344133144d5b62cd65b1ad8eb815c35 | a78fd64159b1fe951d321c8198aec02a42ac5f4d2ec5f5a84b6bc592c4e1891e | O=C(Nc1cccc2c1[nH]c1cnccc12)[C@@H]1COCCN1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[#8:5]-[C:6]-[C:7]-[NH;D2;+0:8]-1.O=[CH2;D1;+0:9].[#7;a:10]:[c:11]:[c:12]:[#7;a:13]:[c:14](:[c:15]):[c:16](-[NH2;D1;+0:17]):[c:18]>>[#7;a:10]:[c:11]:[c:12]:[#7;a:13]:[c:14](:[c:15]):[c:16](-[NH;D2;+0:17]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[#8:5]-[C:6]-[C:7]-[N;H0;D3;+0... | 54.5 | [{"value": 54.5, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)[C@H]1N(CCOC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | A slurry of morpholine-3(S)-carboxylic acid (3.00 g, 22.9 mmol) in EtOH (115 ml) was stirred at RT. A solution of aqueous CH2O (3.42 ml, 45.8 mmol, 37% w/w in H2O) was added, followed by Pd(OH)2 (600 mg, 20% w/w on charcoal). The flask was charged with hydrogen (1 atm) and the grey slurry was stirred for 24 hr at RT un... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Carboxylic acid.Primary amine.Secondary amine | Secondary amide.Tertiary amine | C1COCCN1 | C1COCC[NH]1 | C1COCC[NH]1.c1ccc2c(c1)[nH]c1cnccc12 | HO- | [OH-].[OH-].[Pd+2].CCOC(=O)C.O.CCO.N1=CC=CC=C1 | null | 24 | C=O.Nc1cc(Cl)cc2c1[nH]c1cnccc12.O=C(O)[C@@H]1COCCN1>[OH-].[OH-].[Pd+2].CCOC(=O)C.O.CCO.N1=CC=CC=C1>CN1CCOC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-2b280253fe694eeb9c97b4f613f7983b | CC(C)(C)OC(=O)N1CCOC[C@H]1C(=O)O.Nc1cc(Cl)cc2c1[nH]c1cnccc12>>CC(C)(C)OC(=O)N1CCOC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 | CCN=C=NCCCN(C)C.CCOC(=O)C.C(C)(C)(C)OC(=O)N1[C@@H](COCC1)C(=O)O.ClC=1C=C2C=3C=CN=CC3NC2=C(C1)N>>C(C)(C)(C)OC(=O)N1[C@@H](COCC1)C(NC=1C=C(C=C2C=3C=CN=CC3NC12)Cl)=O | O[C:14]([C@H:13]1[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10][O:11][CH2:12]1)=[O:15].[NH2:16][c:17]1[cH:18][c:19]([Cl:20])[cH:21][c:22]2[c:23]1[nH:24][c:25]1[cH:26][n:27][cH:28][cH:29][c:30]21>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][O:11][CH2:12][C@H:13]1[C:14](=... | CC(C)(C)OC(=O)N1CCOC[C@H]1C(=O)O.Nc1cc(Cl)cc2c1[nH]c1cnccc12 | CC(C)(C)OC(=O)N1CCOC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 | null | null | O.[Cl-].[Na+].O.N1=CC=CC=C1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1cccc2c1[nH]c1cnccc12)[C@@H]1COCCN1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4]-[#8:5])-[#7:6](-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[C;D1;H3:13])-[C:14].[#7;a:15]:[c:16]:[c:17]:[#7;a:18]:[c:19](:[c:20]):[c:21](-[NH2;D1;+0:22]):[c:23]>>[#7;a:15]:[c:16]:[c:17]:[#7;a:18]:[c:19](:[c:20]):[c:21](-[NH;D2;+0:22]-[C;H0;D3;+0:1](=[O;D1... | null | [] | null | null | 14 | HOUR | A solution of morpholine-3(S),4-dicarboxylic acid 4-tert-butyl ester (2.83 g, 12.7 mmol) in pyridine (106 ml) was stirred at RT. 6-chloro-9H-β-carbolin-8-ylamine (2.30 g, 10.6 mmol) was added, followed by EDCI (4.06 g, 21.2 mmol). The clear orange-to-brown solution was stirred at RT for 14 hr. The solution was diluted ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1COCC[NH]1.c1ccc2c(c1)[nH]c1cnccc12 | HO- | O.[Cl-].[Na+].O.N1=CC=CC=C1 | null | 14 | CC(C)(C)OC(=O)N1CCOC[C@H]1C(=O)O.Nc1cc(Cl)cc2c1[nH]c1cnccc12>O.[Cl-].[Na+].O.N1=CC=CC=C1>CC(C)(C)OC(=O)N1CCOC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-50d4c2e26ecd476e9c7e1be4b22dd7e7 | CC(C)(C)OC(=O)N1CCC[C@@H]1C=O.CC(C)(C)OC(=O)N1CCOC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12>>CC(C)(C)OC(=O)N1CCC[C@@H]1CN1CCOC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 | C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+].FC(C(=O)O)(F)F.C(C)(C)(C)OC(=O)N1[C@@H](COCC1)C(NC=1C=C(C=C2C=3C=CN=CC3NC12)Cl)=O.C(C)(C)(C)OC(=O)N1[C@@H](C=O)CCC1>>C(C)(C)(C)OC(=O)N1[C@H](CCC1)CN1[C@@H](COCC1)C(NC=1C=C(C=C2C=3C=CN=CC3NC12)Cl)=O | O=[CH:13][C@@H:12]1[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10][CH2:11]1.CC(C)(C)OC(=O)[N:14]1[CH2:15][CH2:16][O:17][CH2:18][C@H:19]1[C:20](=[O:21])[NH:22][c:23]1[cH:24][c:25]([Cl:26])[cH:27][c:28]2[c:29]1[nH:30][c:31]1[cH:32][n:33][cH:34][cH:35][c:36]21>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:... | CC(C)(C)OC(=O)N1CCC[C@@H]1C=O.CC(C)(C)OC(=O)N1CCOC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 | CC(C)(C)OC(=O)N1CCC[C@@H]1CN1CCOC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 | null | null | C1CCOC1.CO.C(Cl)Cl.C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 07a8dd0a63a2f032256383ed14d5b2300f3182a12f0d3bca1f1edfc26fa061f9 | cf54569061a197ba9f3cab07727ad571966e8f550ff4245a3fd82ef36fe97477 | O=C(Nc1cccc2c1[nH]c1cnccc12)[C@@H]1COCCN1C[C@H]1CCCN1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#8:4]-[C:5]-[C:6]-1-[C:7](=[O;D1;H0:8])-[#7:9]-[c:10]:[c:11]:[#7;a:12].O=[CH;D2;+0:13]-[C:14](-[C:15])-[#7:16](-[C:17](=[O;D1;H0:18])-[#8:19]-[C:20](-[C;D1;H3:21])(-[C;D1;H3:22])-[C;D1;H3:23])-[C:24]>>[#7;a:12]:[c:11]:[c:10]-[#7:9]-[C:7](=[O;D1;H0:8])-[C:6]1-[C:5]-[#8:4]... | 76.7 | [{"value": 76.7, "product": "C(C)(C)(C)OC(=O)N1[C@H](CCC1)CN1[C@@H](COCC1)C(NC=1C=C(C=C2C=3C=CN=CC3NC12)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 45 | MINUTE | A solution of 3(S)-(6-chloro-9H-β-carbolin-8-ylcarbamoyl)-morpholine-4-carboxylic acid tert-butyl ester (1.00 g, 2.32 mmol) in CH2Cl2 (6 ml) was stirred at RT. Trifluoroacetic acid (6 ml) was added and the solution was stirred at RT for 45 min, then concentrated to a residue. The residue was concentrated once more from... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Carbamic ester.Ether.Boc | Tertiary amine | C1COCC[NH]1 | C1COCC[NH]1 | C1CC[NH]C1.C1COCC[NH]1.c1ccc2c(c1)[nH]c1cnccc12 | HO- | C1CCOC1.CO.C(Cl)Cl.C(Cl)Cl | null | 0.75 | CC(C)(C)OC(=O)N1CCC[C@@H]1C=O.CC(C)(C)OC(=O)N1CCOC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12>C1CCOC1.CO.C(Cl)Cl.C(Cl)Cl>CC(C)(C)OC(=O)N1CCC[C@@H]1CN1CCOC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-d432fcaf3af3447bbf3a4599b44cc9a3 | CC(C)(C)OC(=O)NC1CCCC1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12>>N[C@H]1CCC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 | ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)C1C(CCC1)NC(=O)OC(C)(C)C>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)[C@H]1[C@H](CCC1)N | CC(C)(C)OC(=O)[NH:1][CH:2]1[CH2:3][CH2:4][CH2:5][CH:6]1[C:7](=[O:8])[NH:9][c:10]1[cH:11][c:12]([Cl:13])[cH:14][c:15]2[c:16]1[nH:17][c:18]1[cH:19][n:20][cH:21][cH:22][c:23]21>>[NH2:1][C@H:2]1[CH2:3][CH2:4][CH2:5][C@H:6]1[C:7](=[O:8])[NH:9][c:10]1[cH:11][c:12]([Cl:13])[cH:14][c:15]2[c:16]1[nH:17][c:18]1[cH:19][n:20][cH:2... | CC(C)(C)OC(=O)NC1CCCC1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 | N[C@H]1CCC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 | null | null | FC(C(=O)O)(F)F | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C(Nc1cccc2c1[nH]c1cnccc12)C1CCCC1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[CH;D3;+0:2]1-[C:3]-[C:4]-[C:5]-[CH;D3;+0:6]-1-[C:7](=[O;D1;H0:8])-[#7:9]-[c:10]:[c:11]:[#7;a:12]>>[#7;a:12]:[c:11]:[c:10]-[#7:9]-[C:7](=[O;D1;H0:8])-[C@@H;D3;+0:6]1-[C:5]-[C:4]-[C:3]-[C@@H;D3;+0:2]-1-[NH2;D1;+0:1] | 106.1 | [{"value": 106.1, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)[C@H]1[C@H](CCC1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of 2-(tert-butoxycarbonylamino)-cyclopentanecarboxylic acid (6-chloro-9H-β-carbolin-8-yl) amide (736 mg, 1.72 mmol) in trifluoroacetic acid (5 ml) was stirred at RT for 20 min, then concentrated to an orange oil. The oil was dissolved in MeOH (5 ml) and neutralized with a saturated aqueous sodium bicarbonate... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | C1CCCC1.c1ccc2c(c1)[nH]c1cnccc12 | HO- | FC(C(=O)O)(F)F | null | 0.5 | CC(C)(C)OC(=O)NC1CCCC1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12>FC(C(=O)O)(F)F>N[C@H]1CCC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-89d195654d274ffc9909fd1658d0890f | CC(C)(C)OC(=O)N[C@H]1CCCC[C@H]1C(=O)O.Nc1cc(Cl)cc2c1[nH]c1cnccc12.[Na+]>>NC1CCCCC1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12.[Na+] | FC(C(=O)O)(F)F.ClC=1C=C2C=3C=CN=CC3NC2=C(C1)N.CCN=C=NCCCN(C)C.C(C)(C)(C)OC(=O)N[C@@H]1[C@@H](CCCC1)C(=O)O.C(=O)([O-])[O-].[Na+].[Na+]>>C(=O)([O-])[O-].[Na+].[Na+].ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)C1C(CCCC1)N | CC(C)(C)OC(=O)[NH:1][C@H:2]1[CH2:3][CH2:4][CH2:5][CH2:6][C@H:7]1[C:8](O)=[O:9].[NH2:10][c:11]1[cH:12][c:13]([Cl:14])[cH:15][c:16]2[c:17]1[nH:18][c:19]1[cH:20][n:21][cH:22][cH:23][c:24]21.[Na+:29]>>[NH2:1][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH:7]1[C:8](=[O:9])[NH:10][c:11]1[cH:12][c:13]([Cl:14])[cH:15][c:16]2[c:17]1[nH:... | CC(C)(C)OC(=O)N[C@H]1CCCC[C@H]1C(=O)O.Nc1cc(Cl)cc2c1[nH]c1cnccc12.[Na+] | NC1CCCCC1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12.[Na+] | null | null | CCOC(=O)C.O.CO.C(Cl)Cl.N1=CC=CC=C1 | Acylation | OtherReaction | b4c20342f55b434660078663f02be082076e2ff9b9068db91acc0b381022a32e | e525bb030a9f5f4a2fc47bce923bf921a3769ce3300b3fa2600575194671a3f3 | O=C(Nc1cccc2c1[nH]c1cnccc12)C1CCCCC1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C@H;D3;+0:2]1-[C:3]-[C:4]-[C:5]-[C:6]-[C@H;D3;+0:7]-1-[C;H0;D3;+0:8](-O)=[O;D1;H0:9].[#7;a:10]:[c:11]:[c:12]:[#7;a:13]:[c:14](:[c:15]):[c:16](-[NH2;D1;+0:17]):[c:18]>>[#7;a:10]:[c:11]:[c:12]:[#7;a:13]:[c:14](:[c:15]):[c:16](-[NH;D2;+0:17]-[C;H0;D3;+0:8](=[O;D1;H0:9])-[CH;D3;+0:7]1-[C:6... | null | [] | null | null | 16 | HOUR | A solution of cis-2-(tert-butoxycarbonylamino)-cyclohexane carboxylic acid (255 mg, 1.05 mmol) in pyridine (10 ml) was stirred at RT. 6-chloro-9H-β-carbolin-8-ylamine (218 mg, 1.00 mmol) was added, followed by EDCI (315 mg, 1.64 mmol) and the slightly turbid pale orange solution was stirred at RT for 16 hr. The solutio... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Primary amine.Boc | Secondary amide.Primary amine | null | null | C1CCCCC1.c1ccc2c(c1)[nH]c1cnccc12 | HO- | CCOC(=O)C.O.CO.C(Cl)Cl.N1=CC=CC=C1 | null | 16 | CC(C)(C)OC(=O)N[C@H]1CCCC[C@H]1C(=O)O.Nc1cc(Cl)cc2c1[nH]c1cnccc12.[Na+]>CCOC(=O)C.O.CO.C(Cl)Cl.N1=CC=CC=C1>NC1CCCCC1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12.[Na+] |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-a9c8b2ef391f41859897bec5f3ce5352 | O.O=C(c1ccccc1)N1CCc2c([nH]c3ccc(Cl)cc23)C1>>O=C1CN(C(=O)c2ccccc2)Cc2[nH]c3ccc(Cl)cc3c21 | ClC=1C=C2C=3CCN(CC3NC2=CC1)C(=O)C1=CC=CC=C1.C(#N)C1=C(C(=O)C(=C(C1=O)Cl)Cl)C#N.C1CCOC1.O>>C(C1=CC=CC=C1)(=O)N1CC=2NC3=CC=C(C=C3C2C(C1)=O)Cl | [OH2:1].[CH2:2]1[CH2:3][N:4]([C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[CH2:13][c:14]2[nH:15][c:16]3[cH:17][cH:18][c:19]([Cl:20])[cH:21][c:22]3[c:23]21>>[O:1]=[C:2]1[CH2:3][N:4]([C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[CH2:13][c:14]2[nH:15][c:16]3[cH:17][cH:18][c:19]([Cl:20])[cH:21][c:22]3[c:2... | O.O=C(c1ccccc1)N1CCc2c([nH]c3ccc(Cl)cc23)C1 | O=C1CN(C(=O)c2ccccc2)Cc2[nH]c3ccc(Cl)cc3c21 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 94fb5a061868702b7ba4b162fda0d481a656d3f8461c89d8da115f78d870c628 | a196f7191876ee39420290ab9d6c2b9eeb3251b37ae345fc435efba1949a85d9 | O=C1CN(C(=O)c2ccccc2)Cc2[nH]c3ccccc3c21 | [O;D1;H0:1]=[C:2]-[#7:3]1-[C:4]-[c:5]2:[#7;a:6]:[c:7]:[c:8]:[c:9]:2-[CH2;D2;+0:10]-[C:11]-1.[OH2;D0;+0:12]>>[O;D1;H0:1]=[C:2]-[#7:3]1-[C:4]-[c:5]2:[#7;a:6]:[c:7]:[c:8]:[c:9]:2-[C;H0;D3;+0:10](=[O;H0;D1;+0:12])-[C:11]-1 | 75.1 | [{"value": 75.0, "product": "C(C1=CC=CC=C1)(=O)N1CC=2NC3=CC=C(C=C3C2C(C1)=O)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.1, "product": "C(C1=CC=CC=C1)(=O)N1CC=2NC3=CC=C(C=C3C2C(C1)=O)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 2 | HOUR | (6-chloro-1,3,4,9-tetrahydro-β-carbolin-2-yl)-phenyl-methanone (1.76 g, 5.66 mmol, 1 equiv.) and DDQ (2.31 g, 10.2 mmol, 1.8 equiv.) were mixed as solids and cooled to −78° C. 15 ml of a 9:1 THF/H2O solution was cooled to −78° C. and the resulting slurry was added to the cooled solids followed by an additional 15 ml of... | 10.6084/m9.figshare.5104873.v1 | null | null | Ketone | c1ccc2c3c(nc2c1)C[N]CC3 | c1ccc2c3c(nc2c1)C[N]CC3 | c1ccccc1.c1ccc2c3c(nc2c1)C[N]CC3 | null | C1CCOC1 | -78 | 2 | O.O=C(c1ccccc1)N1CCc2c([nH]c3ccc(Cl)cc23)C1>C1CCOC1>O=C1CN(C(=O)c2ccccc2)Cc2[nH]c3ccc(Cl)cc3c21 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-7898338d32e44508a9b26d36d2f6cd9f | NN.O=C1CN(C(=O)c2ccccc2)Cc2[nH]c3ccc(Cl)cc3c21>>Nc1cncc2[nH]c3ccc(Cl)cc3c12 | C(C1=CC=CC=C1)(=O)N1CC=2NC3=CC=C(C=C3C2C(C1)=O)Cl.NN>>NC1=CN=CC=2NC3=CC=C(C=C3C12)Cl | N[NH2:1].O=C(c1ccccc1)[N:4]1[CH2:3][C:2](=O)[c:15]2[c:6]([nH:7][c:8]3[cH:9][cH:10][c:11]([Cl:12])[cH:13][c:14]32)[CH2:5]1>>[NH2:1][c:2]1[cH:3][n:4][cH:5][c:6]2[nH:7][c:8]3[cH:9][cH:10][c:11]([Cl:12])[cH:13][c:14]3[c:15]12 | NN.O=C1CN(C(=O)c2ccccc2)Cc2[nH]c3ccc(Cl)cc3c21 | Nc1cncc2[nH]c3ccc(Cl)cc3c12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 74c41a61e84a9469a525e15f8dfef263462c61ba637c9c616d03a23850e3333b | 2a646b944ed492fc0f255d8794451efd5267945a96cfe9177952895f86f62143 | c1ccc2c(c1)[nH]c1cnccc12 | N-[NH2;D1;+0:1].O=C(-[N;H0;D3;+0:2]1-[CH2;D2;+0:3]-[C;H0;D3;+0:4](=O)-[c:5]2:[c:6]:[c:7]:[#7;a:8]:[c:9]:2-[CH2;D2;+0:10]-1)-c1:c:c:c:c:c:1>>[NH2;D1;+0:1]-[c;H0;D3;+0:4]1:[cH;D2;+0:3]:[n;H0;D2;+0:2]:[cH;D2;+0:10]:[c:9]2:[#7;a:8]:[c:7]:[c:6]:[c:5]:2:1 | 30 | [{"value": 30.0, "product": "NC1=CN=CC=2NC3=CC=C(C=C3C12)Cl", "details": "PERCENTYIELD", "is_desired": false}] | 130 | CELSIUS | 8 | HOUR | Crude 2-benzoyl-6-chloro-1,2,3,9-tetrahydro-β-carbolin-4-one (4 g) was dissolved in 30 ml of anhydrous hydrazine and stirred at reflux (130° C. oil bath) under N2 for 6 hours, after which the reaction mixture was allowed to cool to room temperature and sit overnight. The precipitated yellow solids were removed by filtr... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Tertiary amide | Primary amine | c1ccccc1.c1ccc2c3c(nc2c1)C[N]CC3 | c1ccc2c(c1)[nH]c1cnccc12 | c1ccc2c(c1)[nH]c1cnccc12 | HO- | null | 130 | 8 | NN.O=C1CN(C(=O)c2ccccc2)Cc2[nH]c3ccc(Cl)cc3c21>>Nc1cncc2[nH]c3ccc(Cl)cc3c12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-f4a8badd434f420299d63634ba616cce | O=C(Nc1cncc2[nH]c3ccc(Cl)cc3c12)C(F)(F)F.O=N[O-]>>O=C(Nc1cncc2[nH]c3c([N+](=O)[O-])cc(Cl)cc3c12)C(F)(F)F | ClC=1C=C2C=3C(=CN=CC3NC2=CC1)NC(C(F)(F)F)=O.N(=O)[O-].[Na+]>>ClC=1C=C2C=3C(=CN=CC3NC2=C(C1)[N+](=O)[O-])NC(C(F)(F)F)=O | [O:1]=[C:2]([NH:3][c:4]1[cH:5][n:6][cH:7][c:8]2[nH:9][c:10]3[cH:11][cH:15][c:16]([Cl:17])[cH:18][c:19]3[c:20]12)[C:21]([F:22])([F:23])[F:24].[N:12](=[O:13])[O-:14]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][n:6][cH:7][c:8]2[nH:9][c:10]3[c:11]([N+:12](=[O:13])[O-:14])[cH:15][c:16]([Cl:17])[cH:18][c:19]3[c:20]12)[C:21]([F:22])([F:2... | O=C(Nc1cncc2[nH]c3ccc(Cl)cc3c12)C(F)(F)F.O=N[O-] | O=C(Nc1cncc2[nH]c3c([N+](=O)[O-])cc(Cl)cc3c12)C(F)(F)F | null | null | C(=O)(C(F)(F)F)O | Heteroatom Alkylation and Arylation | Aromatic nitration with NO2 salt | 27d40c1a20be8489ca12a83b18d23e1c4bd9993bff3d46a4c37aaa2b269b5ab4 | 1afb031e90b32de55305394c30af064cce0ffa4f7a6ceb037d1648f24219cbc1 | c1ccc2c(c1)[nH]c1cnccc12 | [#7;a:1]:[c:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9].[O;-;D1;H0:10]-[N;H0;D2;+0:11]=[O;D1;H0:12]>>[#7;a:1]:[c:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c;H0;D3;+0:7](-[N+;H0;D3:11](-[O;-;D1;H0:10])=[O;D1;H0:12]):[c:8]:[c:9] | 92 | [{"value": 92.0, "product": "ClC=1C=C2C=3C(=CN=CC3NC2=C(C1)[N+](=O)[O-])NC(C(F)(F)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.0, "product": "ClC=1C=C2C=3C(=CN=CC3NC2=C(C1)[N+](=O)[O-])NC(C(F)(F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | N-(6-chloro-9H-β-carbolin-4-yl)-2,2,2-trifluoro-acetamide (125 mg, 0.4 mmol, 1 equiv.) was dissolved in 2 ml TFA and NaNO2 (541 mg, 7.84 mmol, 2 equiv.) was added in one portion. The solution was stirred at room temperature for 4 hr. Volatiles were removed by rotovap, and the resulting oily orange solids were suspended... | 10.6084/m9.figshare.5104873.v1 | null | Nitroso | Nitro group | c1ccc2c(c1)[nH]c1cnccc12 | c1ccc2c(c1)[nH]c1cnccc12 | c1ccc2c(c1)[nH]c1cnccc12 | null | C(=O)(C(F)(F)F)O | null | 4 | O=C(Nc1cncc2[nH]c3ccc(Cl)cc3c12)C(F)(F)F.O=N[O-]>C(=O)(C(F)(F)F)O>O=C(Nc1cncc2[nH]c3c([N+](=O)[O-])cc(Cl)cc3c12)C(F)(F)F |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-43960de9c44a4b3286a26c07d143e575 | O=C(Nc1cncc2[nH]c3c([N+](=O)[O-])cc(Cl)cc3c12)C(F)(F)F>>Nc1cc(Cl)cc2c1[nH]c1cncc(NC(=O)C(F)(F)F)c12 | ClC=1C=C2C=3C(=CN=CC3NC2=C(C1)[N+](=O)[O-])NC(C(F)(F)F)=O>>NC=1C=C(C=C2C=3C(=CN=CC3NC12)NC(C(F)(F)F)=O)Cl | O=[N+:1]([O-])[c:2]1[cH:3][c:4]([Cl:5])[cH:6][c:7]2[c:8]1[nH:9][c:10]1[cH:11][n:12][cH:13][c:14]([NH:15][C:16](=[O:17])[C:18]([F:19])([F:20])[F:21])[c:22]21>>[NH2:1][c:2]1[cH:3][c:4]([Cl:5])[cH:6][c:7]2[c:8]1[nH:9][c:10]1[cH:11][n:12][cH:13][c:14]([NH:15][C:16](=[O:17])[C:18]([F:19])([F:20])[F:21])[c:22]21 | O=C(Nc1cncc2[nH]c3c([N+](=O)[O-])cc(Cl)cc3c12)C(F)(F)F | Nc1cc(Cl)cc2c1[nH]c1cncc(NC(=O)C(F)(F)F)c12 | null | null | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2c(c1)[nH]c1cnccc12 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]:[c:8]:[#7;a:9]>>[#7;a:9]:[c:8]:[c:7]:[#7;a:6]:[c:4](:[c:5]):[c:2](-[NH2;D1;+0:1]):[c:3] | 95 | [{"value": 95.0, "product": "NC=1C=C(C=C2C=3C(=CN=CC3NC12)NC(C(F)(F)F)=O)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.7, "product": "NC=1C=C(C=C2C=3C(=CN=CC3NC12)NC(C(F)(F)F)=O)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | The crude N-(6-chloro-8-nitro-9H-β-carbolin-4-yl)-2,2,2-trifluoro-acetamide (130 mg, 0.36 mmol) was dissolved in 7 ml of MeOH and the reaction vessel was vacuum purged 3× with N2. Platinum (20 mg, 20% wt. on activated carbon) was added quickly, and the reaction vessel was again vacuum purged 3× with N2, followed by 3 a... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2c(c1)[nH]c1cnccc12 | Other | CO | null | 8 | O=C(Nc1cncc2[nH]c3c([N+](=O)[O-])cc(Cl)cc3c12)C(F)(F)F>CO>Nc1cc(Cl)cc2c1[nH]c1cncc(NC(=O)C(F)(F)F)c12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-729d7e71038f4e0fbe7010d97014baa8 | Cc1ncccc1C(=O)O.Nc1cc(Cl)cc2c1[nH]c1cncc(NC(=O)C(F)(F)F)c12>>Cc1ncccc1C(=O)Nc1cc(Cl)cc2c1[nH]c1cncc(NC(=O)C(F)(F)F)c12 | NC=1C=C(C=C2C=3C(=CN=CC3NC12)NC(C(F)(F)F)=O)Cl.CC1=C(C(=O)O)C=CC=N1.CCN=C=NCCCN(C)C>>ClC=1C=C2C=3C(=CN=CC3NC2=C(C1)NC(C1=C(N=CC=C1)C)=O)NC(C(F)(F)F)=O | O[C:8]([c:7]1[c:2]([CH3:1])[n:3][cH:4][cH:5][cH:6]1)=[O:9].[NH2:10][c:11]1[cH:12][c:13]([Cl:14])[cH:15][c:16]2[c:17]1[nH:18][c:19]1[cH:20][n:21][cH:22][c:23]([NH:24][C:25](=[O:26])[C:27]([F:28])([F:29])[F:30])[c:31]21>>[CH3:1][c:2]1[n:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[NH:10][c:11]1[cH:12][c:13]([Cl:14])[cH:15][c:... | Cc1ncccc1C(=O)O.Nc1cc(Cl)cc2c1[nH]c1cncc(NC(=O)C(F)(F)F)c12 | Cc1ncccc1C(=O)Nc1cc(Cl)cc2c1[nH]c1cncc(NC(=O)C(F)(F)F)c12 | null | null | N1=CC=CC=C1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1cccc2c1[nH]c1cnccc12)c1cccnc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[C;D1;H3:6]):[#7;a:7]:[c:8].[#7;a:9]:[c:10]:[c:11]:[#7;a:12]:[c:13](:[c:14]):[c:15](-[NH2;D1;+0:16]):[c:17]>>[#7;a:9]:[c:10]:[c:11]:[#7;a:12]:[c:13](:[c:14]):[c:15](-[NH;D2;+0:16]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[C;D1;H3:6]):[#7;a:7]:[c:8]):[c:17] | 33.4 | [{"value": 3.0, "product": "ClC=1C=C2C=3C(=CN=CC3NC2=C(C1)NC(C1=C(N=CC=C1)C)=O)NC(C(F)(F)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 33.4, "product": "ClC=1C=C2C=3C(=CN=CC3NC2=C(C1)NC(C1=C(N=CC=C1)C)=O)NC(C(F)(F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | N-(8-amino-6-chloro-9H-β-carbolin-4-yl)-2,2,2-trifluoro-acetamide (90 mg, 0.274 mmol, 1 equiv.) and 2-methylnicotinic acid (45 mg, 0.329 mmol, 1.2 equiv.) were dissolved in 1.5 ml of anhydrous pyridine under N2. EDCI (84 mg, 0.438 mmol, 1.6 equiv.) was added in one portion and the reaction mixture was stirred at room t... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccc2c(c1)[nH]c1cnccc12 | HO- | N1=CC=CC=C1 | null | 2 | Cc1ncccc1C(=O)O.Nc1cc(Cl)cc2c1[nH]c1cncc(NC(=O)C(F)(F)F)c12>N1=CC=CC=C1>Cc1ncccc1C(=O)Nc1cc(Cl)cc2c1[nH]c1cncc(NC(=O)C(F)(F)F)c12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-0ba7be200a0745fa8dcb6c2a37b8dd3a | Cc1ncccc1C(=O)O.Nc1cc(Cl)cc2c1[nH]c1cncc(NC(=O)C(F)(F)F)c12>>O=C(Nc1cc(Cl)cc2c1[nH]c1cncc(NC(=O)C(F)(F)F)c12)c1cccnc1 | NC=1C=C(C=C2C=3C(=CN=CC3NC12)NC(C(F)(F)F)=O)Cl.CC1=C(C(=O)O)C=CC=N1.CCN=C=NCCCN(C)C>>ClC=1C=C2C=3C(=CN=CC3NC2=C(C1)NC(C1=CN=CC=C1)=O)NC(C(F)(F)F)=O | C[c:30]1[c:25]([C:2](O)=[O:1])[cH:26][cH:27][cH:28][n:29]1.[NH2:3][c:4]1[cH:5][c:6]([Cl:7])[cH:8][c:9]2[c:10]1[nH:11][c:12]1[cH:13][n:14][cH:15][c:16]([NH:17][C:18](=[O:19])[C:20]([F:21])([F:22])[F:23])[c:24]21>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][c:6]([Cl:7])[cH:8][c:9]2[c:10]1[nH:11][c:12]1[cH:13][n:14][cH:15][c:16]([NH:1... | Cc1ncccc1C(=O)O.Nc1cc(Cl)cc2c1[nH]c1cncc(NC(=O)C(F)(F)F)c12 | O=C(Nc1cc(Cl)cc2c1[nH]c1cncc(NC(=O)C(F)(F)F)c12)c1cccnc1 | null | null | N1=CC=CC=C1 | Acylation | OtherReaction | b405a961806bf7c0480e9ba70bff09e2357d2e443a48745daf408dff4513f433 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1cccc2c1[nH]c1cnccc12)c1cccnc1 | C-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[C;H0;D3;+0:5](-O)=[O;D1;H0:6]):[c:7].[#7;a:8]:[c:9]:[c:10]:[#7;a:11]:[c:12](:[c:13]):[c:14](-[NH2;D1;+0:15]):[c:16]>>[#7;a:8]:[c:9]:[c:10]:[#7;a:11]:[c:12](:[c:13]):[c:14](-[NH;D2;+0:15]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[c:4](:[c:7]):[cH;D2;+0:1]:[#7;a:2]:[c:3]):[c:16] | 32 | [{"value": 32.0, "product": "ClC=1C=C2C=3C(=CN=CC3NC2=C(C1)NC(C1=CN=CC=C1)=O)NC(C(F)(F)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.0, "product": "ClC=1C=C2C=3C(=CN=CC3NC2=C(C1)NC(C1=CN=CC=C1)=O)NC(C(F)(F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | N-(8-amino-6-chloro-9H-β-carbolin-4-yl)-2,2,2-trifluoro-acetamide (90 mg, 0.274 mmol, 1 equiv.) and 2-methylnicotinic acid (40 mg, 0.329 mmol, 1.2 equiv.) were dissolved in 1.5 ml of anhydrous pyridine under N2. EDCI (84 mg, 0.438 mmol, 1.6 equiv.) was added in one portion and the reaction mixture was stirred at room t... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | c1ccncc1 | c1ccncc1 | c1ccc2c(c1)[nH]c1cnccc12.c1ccncc1 | HO- | N1=CC=CC=C1 | null | 2 | Cc1ncccc1C(=O)O.Nc1cc(Cl)cc2c1[nH]c1cncc(NC(=O)C(F)(F)F)c12>N1=CC=CC=C1>O=C(Nc1cc(Cl)cc2c1[nH]c1cncc(NC(=O)C(F)(F)F)c12)c1cccnc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-49d4afb4172b4e4e82801fe1f568d711 | O=C(Nc1cc(Cl)cc2c1[nH]c1cncc(NC(=O)C(F)(F)F)c12)c1cccnc1>>Cc1ncccc1C(=O)Nc1cc(Cl)cc2c1[nH]c1cncc(N)c12 | O.ClC=1C=C2C=3C(=CN=CC3NC2=C(C1)NC(C1=CN=CC=C1)=O)NC(C(F)(F)F)=O.C(=O)([O-])[O-].[K+].[K+]>>NC1=CN=CC=2NC3=C(C=C(C=C3C12)Cl)NC(C1=C(N=CC=C1)C)=O | O=C(C(F)(F)F)[NH:24][c:23]1[cH:22][n:21][cH:20][c:19]2[nH:18][c:17]3[c:11]([NH:10][C:8]([c:7]4[cH:2][n:3][cH:4][cH:5][cH:6]4)=[O:9])[cH:12][c:13]([Cl:14])[cH:15][c:16]3[c:25]21>>[CH3:1][c:2]1[n:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[NH:10][c:11]1[cH:12][c:13]([Cl:14])[cH:15][c:16]2[c:17]1[nH:18][c:19]1[cH:20][n:21][cH... | O=C(Nc1cc(Cl)cc2c1[nH]c1cncc(NC(=O)C(F)(F)F)c12)c1cccnc1 | Cc1ncccc1C(=O)Nc1cc(Cl)cc2c1[nH]c1cncc(N)c12 | null | null | CO | Functional Group Interconversion | OtherReaction | 7bdade8e10f63ec35b6f5b02073a2818fdc259338138d32e1d3670d7016f6d6a | 93e9ea1ae4bf2c4ff35caff092b0418f72119be3ac8ebfa7d8fb2a9b49b6c3cb | O=C(Nc1cccc2c1[nH]c1cnccc12)c1cccnc1 | F-C(-F)(-F)-C(=O)-[NH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[c:6](:[#7;a:7]:[c:8]:[c:9]-[#7:10]-[C:11](=[O;D1;H0:12])-[c:13](:[c:14]):[cH;D2;+0:15]:[#7;a:16]:[c:17]):[c:18]:1>>[C;D1;H3:19]-[c;H0;D3;+0:15](:[#7;a:16]:[c:17]):[c:13](-[C:11](=[O;D1;H0:12])-[#7:10]-[c:9]:[c:8]:[#7;a:7]:[c:6]1:[c:5]:[#7;a:4]:[c:3]:[c:2](-[NH... | 56 | [{"value": 56.0, "product": "NC1=CN=CC=2NC3=C(C=C(C=C3C12)Cl)NC(C1=C(N=CC=C1)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.6, "product": "NC1=CN=CC=2NC3=C(C=C(C=C3C12)Cl)NC(C1=C(N=CC=C1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | N-[6-chloro-4-(2,2,2-trifluoro-acetylamino)-9H-β-carbolin-8-yl]-nicotinamide (41 mg, 0.092 mmol, 1 equiv.) was suspended in 5 ml of MeOH and a 2 ml aqueous solution of K2CO3 (127 mg, 0.92 mmol, 10 equiv.) was added thereto. The resulting clear solution was heated at 60° C. for 16 hr and then allowed to cool to RT. Addi... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Secondary amide | Primary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccc2c(c1)[nH]c1cnccc12 | Other | CO | 60 | null | O=C(Nc1cc(Cl)cc2c1[nH]c1cncc(NC(=O)C(F)(F)F)c12)c1cccnc1>CO>Cc1ncccc1C(=O)Nc1cc(Cl)cc2c1[nH]c1cncc(N)c12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-fdd49f50cce6498b86f686e7514911b8 | O=C(Nc1cc(Cl)cc2c1[nH]c1cncc(NC(=O)C(F)(F)F)c12)c1cccnc1>>Nc1cncc2[nH]c3c(NC(=O)c4cccnc4)cc(Cl)cc3c12 | ClC=1C=C2C=3C(=CN=CC3NC2=C(C1)NC(C1=CN=CC=C1)=O)NC(C(F)(F)F)=O.C(=O)([O-])[O-].[K+].[K+]>>NC1=CN=CC=2NC3=C(C=C(C=C3C12)Cl)NC(C1=CN=CC=C1)=O | O=C(C(F)(F)F)[NH:1][c:2]1[cH:3][n:4][cH:5][c:6]2[nH:7][c:8]3[c:9]([NH:10][C:11](=[O:12])[c:13]4[cH:14][cH:15][cH:16][n:17][cH:18]4)[cH:19][c:20]([Cl:21])[cH:22][c:23]3[c:24]12>>[NH2:1][c:2]1[cH:3][n:4][cH:5][c:6]2[nH:7][c:8]3[c:9]([NH:10][C:11](=[O:12])[c:13]4[cH:14][cH:15][cH:16][n:17][cH:18]4)[cH:19][c:20]([Cl:21])[c... | O=C(Nc1cc(Cl)cc2c1[nH]c1cncc(NC(=O)C(F)(F)F)c12)c1cccnc1 | Nc1cncc2[nH]c3c(NC(=O)c4cccnc4)cc(Cl)cc3c12 | null | null | CO | Reduction | Hydrogenolysis of amides/imides/carbamates | 44b36597c7daf0608965c52c8db8a9220c21d9447ce54e0af375898475f3493f | caaeb83af2cb178156ae90fe7f610a106cd4bb5397d23f56d37a7fe11e2668ed | O=C(Nc1cccc2c1[nH]c1cnccc12)c1cccnc1 | F-C(-F)(-F)-C(=O)-[NH;D2;+0:1]-[c:2]1:[c:3]:[c:4](:[#7;a:5]):[c:6]:[#7;a:7]:[c:8]:1>>[#7;a:5]:[c:4]1:[c:3]:[c:2](-[NH2;D1;+0:1]):[c:8]:[#7;a:7]:[c:6]:1 | 10 | [{"value": 10.0, "product": "NC1=CN=CC=2NC3=C(C=C(C=C3C12)Cl)NC(C1=CN=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 9.4, "product": "NC1=CN=CC=2NC3=C(C=C(C=C3C12)Cl)NC(C1=CN=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | N-[6-chloro-4-(2,2,2-trifluoro-acetylamino)-9H-β-carbolin-8-yl]-nicotinamide (38 mg, 0.088 mmol, 1 equiv.) was suspended in 5 ml of MeOH and a 2 ml aqueous solution of K2CO3 (121 mg, 0.92 mmol, 10 equiv.) was added thereto. The resulting clear solution was heated at 60° C. for 11 hr. After cooling to RT, fine solids pr... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Secondary amide | Primary amine | null | null | c1ccncc1.c1ccc2c(c1)[nH]c1cnccc12 | Other | CO | 60 | null | O=C(Nc1cc(Cl)cc2c1[nH]c1cncc(NC(=O)C(F)(F)F)c12)c1cccnc1>CO>Nc1cncc2[nH]c3c(NC(=O)c4cccnc4)cc(Cl)cc3c12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-1a045f84366a4f88ac017f6c5af9c4fc | CC(C)(C)OC(=O)n1cc(CC#N)c2ccccc21.CI>>CC(C#N)c1cn(C(=O)OC(C)(C)C)c2ccccc12 | O.C[Si](C)(C)[N-][Si](C)(C)C.[Na+].C(C)(C)(C)OC(=O)N1C=C(C2=CC=CC=C12)CC#N.IC>>C(C)(C)(C)OC(=O)N1C=C(C2=CC=CC=C12)C(C)C#N | [CH2:2]([C:3]#[N:4])[c:5]1[cH:6][n:7]([C:8](=[O:9])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]12.I[CH3:1]>>[CH3:1][CH:2]([C:3]#[N:4])[c:5]1[cH:6][n:7]([C:8](=[O:9])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]12 | CC(C)(C)OC(=O)n1cc(CC#N)c2ccccc21.CI | CC(C#N)c1cn(C(=O)OC(C)(C)C)c2ccccc12 | null | null | C1CCOC1.CCOC(=O)C | C-C Coupling | Methylation with MeI_secondary | 0e09d968095a587418cca2841b1e4f096e8103de8fbb60e833faf1fb3df36a41 | 410ec9b1cc243569e4ff568c248f0b402403802e002b4018f576af3f6960507b | c1ccc2[nH]ccc2c1 | I-[CH3;D1;+0:1].[#8:2]-[C:3](=[O;D1;H0:4])-[#7;a:5]1:[c:6]:[c:7]:[c:8](-[CH2;D2;+0:9]-[C:10]#[N;D1;H0:11]):[c:12]:1>>[#8:2]-[C:3](=[O;D1;H0:4])-[#7;a:5]1:[c:6]:[c:7]:[c:8](-[CH;D3;+0:9](-[CH3;D1;+0:1])-[C:10]#[N;D1;H0:11]):[c:12]:1 | 79.4 | [{"value": 79.4, "product": "C(C)(C)(C)OC(=O)N1C=C(C2=CC=CC=C12)C(C)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | A stirred solution of 3-cyanomethyl-indole-1-carboxylic acid tert-butyl ester (2.15 g, 8.39 mmol) in THF (40 ml) was cooled to −78° C. under an argon atmosphere. Sodium bis(trimethylsilyl)amide (1 M in THF, 10 ml, 10 mmol) was added thereto and the cold solution was stirred for 30 minutes. Iodomethane (627 uL, 10 mmol)... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1c[nH]c2ccccc12 | HI | C1CCOC1.CCOC(=O)C | 0 | 0.5 | CC(C)(C)OC(=O)n1cc(CC#N)c2ccccc21.CI>C1CCOC1.CCOC(=O)C>CC(C#N)c1cn(C(=O)OC(C)(C)C)c2ccccc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-5a8b7785a1c44cd4a637d2c07fb8374d | CC1CNCc2[nH]c3ccccc3c21>>Cc1cncc2[nH]c3ccccc3c12 | CC1CNCC=2NC3=CC=CC=C3C12>>CC1=CN=CC=2NC3=CC=CC=C3C12 | [CH3:1][CH:2]1[CH2:3][NH:4][CH2:5][c:6]2[nH:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[c:14]21>>[CH3:1][c:2]1[cH:3][n:4][cH:5][c:6]2[nH:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[c:14]12 | CC1CNCc2[nH]c3ccccc3c21 | Cc1cncc2[nH]c3ccccc3c12 | null | [Pd] | null | Oxidation | OtherReaction | 523352700f59a97369e704a2d9a8c0a34702d7e100a14629f0bde803b65f20e2 | 45f806b8e00071c3429c43b3544e10767c5f82b269d7c53bc7fada9a5eb3b8c6 | c1ccc2c(c1)[nH]c1cnccc12 | [C;D1;H3:1]-[CH;D3;+0:2]1-[CH2;D2;+0:3]-[NH;D2;+0:4]-[CH2;D2;+0:5]-[c:6]2:[#7;a:7]:[c:8]:[c:9]:[c:10]:2-1>>[C;D1;H3:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[n;H0;D2;+0:4]:[cH;D2;+0:5]:[c:6]2:[#7;a:7]:[c:8]:[c:9]:[c:10]:2:1 | 98.5 | [{"value": 98.5, "product": "CC1=CN=CC=2NC3=CC=CC=C3C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 160 | CELSIUS | 24 | HOUR | 4-methyl-2,3,4,9-tetrahydro-1H-β-carboline (214 mg, 1.17 mmol) was suspended in xylenes (10 ml). Pd (10% wt. on carbon, 21 mg) catalyst was added thereto and the reaction mixture was stirred at 160° C. for 24 hours, then cooled to RT and filtered through celite. The filtrate was concentrated to dryness to give 4-methyl... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | null | c1ccc2c3c(nc2c1)CNCC3 | c1ccc2c(c1)[nH]c1cnccc12 | c1ccc2c(c1)[nH]c1cnccc12 | null | [Pd] | 160 | 24 | CC1CNCc2[nH]c3ccccc3c21>[Pd]>Cc1cncc2[nH]c3ccccc3c12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-6c4fa2e590f5443b9ababf7aea0a81bf | Cc1cncc2[nH]c3ccccc3c12.O=C1CCC(=O)N1Cl>>Cc1cncc2[nH]c3ccc(Cl)cc3c12 | CC1=CN=CC=2NC3=CC=CC=C3C12.C1CC(=O)N(C1=O)Cl.C([O-])(O)=O.[Na+]>>ClC=1C=C2C=3C(=CN=CC3NC2=CC1)C | [CH3:1][c:2]1[cH:3][n:4][cH:5][c:6]2[nH:7][c:8]3[cH:9][cH:10][cH:11][cH:13][c:14]3[c:15]12.O=C1CCC(=O)N1[Cl:12]>>[CH3:1][c:2]1[cH:3][n:4][cH:5][c:6]2[nH:7][c:8]3[cH:9][cH:10][c:11]([Cl:12])[cH:13][c:14]3[c:15]12 | Cc1cncc2[nH]c3ccccc3c12.O=C1CCC(=O)N1Cl | Cc1cncc2[nH]c3ccc(Cl)cc3c12 | null | null | Cl | Functional Group Interconversion | Chlorination | 0c7815949c87db4c10c2c62b5e92cc3444285641e2a838b0bc2e29f461599b8f | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccc2c(c1)[nH]c1cnccc12 | O=C1-C-C-C(=O)-N-1-[Cl;H0;D1;+0:1].[#7;a:2]:[c:3]1:[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]:1>>[#7;a:2]:[c:3]1:[c:4]:[c:5]:[c;H0;D3;+0:6](-[Cl;H0;D1;+0:1]):[c:7]:[c:8]:1 | 93.7 | [{"value": 93.7, "product": "ClC=1C=C2C=3C(=CN=CC3NC2=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-methyl-9H-β-carboline (97 mg, 0.532 mmol) was dissolved in HCl (1N, 4 ml) and stirred at RT. NCS (85 mg, 0.637 mmol) was added thereto and the reaction mixture was stirred for 5 hr. Saturated sodium bicarbonate solution (20 ml) was added thereto and the reaction mixture was extracted twice with EtOAc (100 ml). The co... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ccc2c(c1)[nH]c1cnccc12.C1CCNC1 | c1ccc2c(c1)[nH]c1cnccc12 | c1ccc2c(c1)[nH]c1cnccc12 | HO- | Cl | null | null | Cc1cncc2[nH]c3ccccc3c12.O=C1CCC(=O)N1Cl>Cl>Cc1cncc2[nH]c3ccc(Cl)cc3c12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-9040f27fcadd491cafbf69bcb116f9b7 | Cc1cncc2[nH]c3c([N+](=O)[O-])cc(Cl)cc3c12>>Cc1cncc2[nH]c3c(N)cc(Cl)cc3c12 | ClC=1C=C2C=3C(=CN=CC3NC2=C(C1)[N+](=O)[O-])C>>ClC=1C=C2C=3C(=CN=CC3NC2=C(C1)N)C | O=[N+:10]([O-])[c:9]1[c:8]2[nH:7][c:6]3[cH:5][n:4][cH:3][c:2]([CH3:1])[c:16]3[c:15]2[cH:14][c:12]([Cl:13])[cH:11]1>>[CH3:1][c:2]1[cH:3][n:4][cH:5][c:6]2[nH:7][c:8]3[c:9]([NH2:10])[cH:11][c:12]([Cl:13])[cH:14][c:15]3[c:16]12 | Cc1cncc2[nH]c3c([N+](=O)[O-])cc(Cl)cc3c12 | Cc1cncc2[nH]c3c(N)cc(Cl)cc3c12 | null | [Pt] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2c(c1)[nH]c1cnccc12 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]:[c:8]:[#7;a:9]>>[#7;a:9]:[c:8]:[c:7]:[#7;a:6]:[c:4](:[c:5]):[c:2](-[NH2;D1;+0:1]):[c:3] | 93.3 | [{"value": 93.3, "product": "ClC=1C=C2C=3C(=CN=CC3NC2=C(C1)N)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | A solution of 6-chloro-4-methyl-8-nitro-9H-β-carboline (80 mg, 0.31 mmol) in MeOH (10 ml) was stirred at RT. Platinum (10% wt. on carbon, 24 mg) catalyst was added thereto and the reaction vessel was capped and vacuum purged 3 times with argon, followed similarly by hydrogen. The reaction mixture was stirred 1.5 hr und... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2c(c1)[nH]c1cnccc12 | Other | [Pt].CO | null | 1.5 | Cc1cncc2[nH]c3c([N+](=O)[O-])cc(Cl)cc3c12>[Pt].CO>Cc1cncc2[nH]c3c(N)cc(Cl)cc3c12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-6ae8c9d0d8654400b65d536d16c21f9b | Cc1cncc2[nH]c3c(N)cc(Cl)cc3c12.O=C(Cl)c1cccnc1>>Cc1cncc2[nH]c3c(NC(=O)c4cccnc4)cc(Cl)cc3c12 | CCOC(=O)C.ClC=1C=C2C=3C(=CN=CC3NC2=C(C1)N)C.Cl.C(C1=CN=CC=C1)(=O)Cl>>ClC=1C=C2C=3C(=CN=CC3NC2=C(C1)NC(C1=CN=CC=C1)=O)C | [CH3:1][c:2]1[cH:3][n:4][cH:5][c:6]2[nH:7][c:8]3[c:9]([NH2:10])[cH:19][c:20]([Cl:21])[cH:22][c:23]3[c:24]12.Cl[C:11](=[O:12])[c:13]1[cH:14][cH:15][cH:16][n:17][cH:18]1>>[CH3:1][c:2]1[cH:3][n:4][cH:5][c:6]2[nH:7][c:8]3[c:9]([NH:10][C:11](=[O:12])[c:13]4[cH:14][cH:15][cH:16][n:17][cH:18]4)[cH:19][c:20]([Cl:21])[cH:22][c:... | Cc1cncc2[nH]c3c(N)cc(Cl)cc3c12.O=C(Cl)c1cccnc1 | Cc1cncc2[nH]c3c(NC(=O)c4cccnc4)cc(Cl)cc3c12 | null | null | O.N1=CC=CC=C1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1cccc2c1[nH]c1cnccc12)c1cccnc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7].[#7;a:8]:[c:9]:[c:10]:[#7;a:11]:[c:12](:[c:13]):[c:14](-[NH2;D1;+0:15]):[c:16]>>[#7;a:8]:[c:9]:[c:10]:[#7;a:11]:[c:12](:[c:13]):[c:14](-[NH;D2;+0:15]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7]):[c:16] | 8.1 | [{"value": 8.1, "product": "ClC=1C=C2C=3C(=CN=CC3NC2=C(C1)NC(C1=CN=CC=C1)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | A solution of 6-chloro-4-methyl-9H-β-carbolin-8-ylamine (43 mg, 0.19 mmol) in pyridine (4 ml) was stirred at RT under an argon atmosphere. Nicotinoyl chloride hydrochloride (40 mg, 0.22 mmol) was added thereto and the reaction mixture was stirred for 12 hr. The solution was diluted with H2O (5 ml) and poured into a sep... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccc2c(c1)[nH]c1cnccc12 | HCl | O.N1=CC=CC=C1 | null | 12 | Cc1cncc2[nH]c3c(N)cc(Cl)cc3c12.O=C(Cl)c1cccnc1>O.N1=CC=CC=C1>Cc1cncc2[nH]c3c(NC(=O)c4cccnc4)cc(Cl)cc3c12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-a27e6a4f7bd746fdaef7e84f334dece2 | CC(C)(C)OC(=O)N1CC(C)(C)OCC1C(=O)O.Nc1cc(Cl)cc2c1[nH]c1cnccc12>>CC(C)(C)OC(=O)N1CC(C)(C)OC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 | ClC=1C=C2C=3C=CN=CC3NC2=C(C1)N.C(C)(C)(C)OC(=O)N1C(COC(C1)(C)C)C(=O)O>>C(C)(C)(C)OC(=O)N1CC(OC[C@H]1C(NC=1C=C(C=C2C=3C=CN=CC3NC12)Cl)=O)(C)C | O[C:16]([CH:15]1[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][C:10]([CH3:11])([CH3:12])[O:13][CH2:14]1)=[O:17].[NH2:18][c:19]1[cH:20][c:21]([Cl:22])[cH:23][c:24]2[c:25]1[nH:26][c:27]1[cH:28][n:29][cH:30][cH:31][c:32]21>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][C:10]([CH3:11])([CH3:... | CC(C)(C)OC(=O)N1CC(C)(C)OCC1C(=O)O.Nc1cc(Cl)cc2c1[nH]c1cnccc12 | CC(C)(C)OC(=O)N1CC(C)(C)OC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1cccc2c1[nH]c1cnccc12)[C@@H]1COCCN1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3]1-[C:4]-[#8:5]-[C:6]-[C:7]-[#7:8]-1-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12](-[C;D1;H3:13])(-[C;D1;H3:14])-[C;D1;H3:15].[#7;a:16]:[c:17]:[c:18]:[#7;a:19]:[c:20](:[c:21]):[c:22](-[NH2;D1;+0:23]):[c:24]>>[#7;a:16]:[c:17]:[c:18]:[#7;a:19]:[c:20](:[c:21]):[c:22](-[NH;D2;+0:23]-[C;H0;D3... | 87 | [{"value": 87.0, "product": "C(C)(C)(C)OC(=O)N1CC(OC[C@H]1C(NC=1C=C(C=C2C=3C=CN=CC3NC12)Cl)=O)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The desired compound was prepared according to Method C from 6-chloro-9H-β-carboline-8-ylamine and 6,6-dimethyl-morpholine-3,4-dicarboxylic acid 4-tert-butyl ester in 87% yield.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1COCC[NH]1.c1ccc2c(c1)[nH]c1cnccc12 | HO- | null | null | null | CC(C)(C)OC(=O)N1CC(C)(C)OCC1C(=O)O.Nc1cc(Cl)cc2c1[nH]c1cnccc12>>CC(C)(C)OC(=O)N1CC(C)(C)OC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-4a68d3ab7de74215a577f8527d987335 | CC(=O)OC(C)=O.CC(N)CN1CC(C)(C)OCC1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12>>CC(=O)N[C@@H](C)CN1CC(C)(C)OC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 | ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)C1N(CC(OC1)(C)C)CC(C)N.C(C)(=O)OC(C)=O>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)[C@H]1N(CC(OC1)(C)C)C[C@H](C)NC(C)=O | CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][CH:5]([CH3:6])[CH2:7][N:8]1[CH2:9][C:10]([CH3:11])([CH3:12])[O:13][CH2:14][CH:15]1[C:16](=[O:17])[NH:18][c:19]1[cH:20][c:21]([Cl:22])[cH:23][c:24]2[c:25]1[nH:26][c:27]1[cH:28][n:29][cH:30][cH:31][c:32]21>>[CH3:1][C:2](=[O:3])[NH:4][C@@H:5]([CH3:6])[CH2:7][N:8]1[CH2:9][C:10]([CH3:11])... | CC(=O)OC(C)=O.CC(N)CN1CC(C)(C)OCC1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 | CC(=O)N[C@@H](C)CN1CC(C)(C)OC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 | null | null | null | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | O=C(Nc1cccc2c1[nH]c1cnccc12)[C@@H]1COCCN1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#7:4]-[C:5]-[CH;D3;+0:6](-[C;D1;H3:7])-[NH2;D1;+0:8]>>[#7:4]-[C:5]-[C@H;D3;+0:6](-[C;D1;H3:7])-[NH;D2;+0:8]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | null | [] | null | null | null | null | The desired compound was prepared according to the previous example from 4-(2-Amino-propyl)-6,6-dimethyl-morpholine-3-carboxylic acid (6-chloro-9H-β-carbolin-8yl)-amide (3 CF3COOH salt) and acetic anhydride.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | C1COCC[NH]1.c1ccc2c(c1)[nH]c1cnccc12 | HO- | null | null | null | CC(=O)OC(C)=O.CC(N)CN1CC(C)(C)OCC1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12>>CC(=O)N[C@@H](C)CN1CC(C)(C)OC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-f0e5fa4ede3b47dca9055aebff913347 | C[C@H](N)CN1CC(C)(C)OC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12.Cc1ncccc1C(=O)O>>Cc1ncccc1C(=O)N[C@@H](C)CN1CC(C)(C)OC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 | FC(C(=O)O)(F)F.ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)[C@H]1N(CC(OC1)(C)C)C[C@H](C)N.CC1=C(C(=O)O)C=CC=N1>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)[C@H]1N(CC(OC1)(C)C)C[C@H](C)NC(=O)C=1C(=NC=CC1)C | [NH2:10][C@@H:11]([CH3:12])[CH2:13][N:14]1[CH2:15][C:16]([CH3:17])([CH3:18])[O:19][CH2:20][C@H:21]1[C:22](=[O:23])[NH:24][c:25]1[cH:26][c:27]([Cl:28])[cH:29][c:30]2[c:31]1[nH:32][c:33]1[cH:34][n:35][cH:36][cH:37][c:38]21.O[C:8]([c:7]1[c:2]([CH3:1])[n:3][cH:4][cH:5][cH:6]1)=[O:9]>>[CH3:1][c:2]1[n:3][cH:4][cH:5][cH:6][c:... | C[C@H](N)CN1CC(C)(C)OC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12.Cc1ncccc1C(=O)O | Cc1ncccc1C(=O)N[C@@H](C)CN1CC(C)(C)OC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCN1CCOC[C@H]1C(=O)Nc1cccc2c1[nH]c1cnccc12)c1cccnc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[C;D1;H3:6]):[#7;a:7]:[c:8].[C:9]-[C:10](-[C;D1;H3:11])-[NH2;D1;+0:12]>>[C:9]-[C:10](-[C;D1;H3:11])-[NH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[C;D1;H3:6]):[#7;a:7]:[c:8] | 75 | [{"value": 75.0, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)[C@H]1N(CC(OC1)(C)C)C[C@H](C)NC(=O)C=1C(=NC=CC1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The desired compound was prepared according to Method E from (S)-4-((S)-2-Amino-propyl)-6,6-dimethyl-morpholine-3-carboxylic acid (6-chloro-9H-beta-carbolin-8-yl)-amide trifluoroacetate salt and 2-methyl-nicotinic acid in 75% yield.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccncc1.C1COCC[NH]1.c1ccc2c(c1)[nH]c1cnccc12 | HO- | null | null | null | C[C@H](N)CN1CC(C)(C)OC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12.Cc1ncccc1C(=O)O>>Cc1ncccc1C(=O)N[C@@H](C)CN1CC(C)(C)OC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-511991e8196149f8bbc6a6fd32b06b34 | COC(=O)Cl.C[C@H](N)CN1CC(C)(C)OC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12>>COC(=O)N[C@@H](C)CN1CC(C)(C)OC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 | O.C(Cl)Cl.Cl.ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)[C@H]1N(CC(OC1)(C)C)C[C@H](C)N.ClC(=O)OC>>COC(N[C@H](CN1CC(OC[C@H]1C(NC=1C=C(C=C2C=3C=CN=CC3NC12)Cl)=O)(C)C)C)=O | Cl[C:3]([O:2][CH3:1])=[O:4].[NH2:5][C@@H:6]([CH3:7])[CH2:8][N:9]1[CH2:10][C:11]([CH3:12])([CH3:13])[O:14][CH2:15][C@H:16]1[C:17](=[O:18])[NH:19][c:20]1[cH:21][c:22]([Cl:23])[cH:24][c:25]2[c:26]1[nH:27][c:28]1[cH:29][n:30][cH:31][cH:32][c:33]21>>[CH3:1][O:2][C:3](=[O:4])[NH:5][C@@H:6]([CH3:7])[CH2:8][N:9]1[CH2:10][C:11]... | COC(=O)Cl.C[C@H](N)CN1CC(C)(C)OC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 | COC(=O)N[C@@H](C)CN1CC(C)(C)OC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 | null | null | N1=CC=CC=C1 | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | O=C(Nc1cccc2c1[nH]c1cnccc12)[C@@H]1COCCN1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[C:5]-[C:6](-[C;D1;H3:7])-[NH2;D1;+0:8]>>[C:5]-[C:6](-[C;D1;H3:7])-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4] | 77 | [{"value": 77.0, "product": "COC(N[C@H](CN1CC(OC[C@H]1C(NC=1C=C(C=C2C=3C=CN=CC3NC12)Cl)=O)(C)C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of (S)-4-((S)-2-Amino-propyl)-6,6-dimethyl-morpholine-3 carboxylic acid (6-chloro-9H-beta-carbolin-8-yl)-amide hydrochloride salt (3.45 g, 6.59 mmole) in 68 ml of dry pyridine, was added in three portions over 1.5 hr, a 3M DCM solution of methyl chloroformate (9.2 ml, 27.6 mmole, 4.2 eq). After 2 h, 10 ml... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | C1COCC[NH]1.c1ccc2c(c1)[nH]c1cnccc12 | HCl | N1=CC=CC=C1 | null | 2 | COC(=O)Cl.C[C@H](N)CN1CC(C)(C)OC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12>N1=CC=CC=C1>COC(=O)N[C@@H](C)CN1CC(C)(C)OC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-1b856251211042118c2fe543f99e5df8 | C[C@H](N)CN1CC(C)(C)OC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12.Cc1ccncc1C(=O)O>>Cc1ccncc1C(=O)N[C@@H](C)CN1CC(C)(C)OC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 | FC(C(=O)O)(F)F.ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)[C@H]1N(CC(OC1)(C)C)C[C@H](C)N.CC1=CC=NC=C1C(=O)O>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)[C@H]1N(CC(OC1)(C)C)C[C@H](C)NC(=O)C=1C=NC=CC1C | [NH2:10][C@@H:11]([CH3:12])[CH2:13][N:14]1[CH2:15][C:16]([CH3:17])([CH3:18])[O:19][CH2:20][C@H:21]1[C:22](=[O:23])[NH:24][c:25]1[cH:26][c:27]([Cl:28])[cH:29][c:30]2[c:31]1[nH:32][c:33]1[cH:34][n:35][cH:36][cH:37][c:38]21.O[C:8]([c:7]1[c:2]([CH3:1])[cH:3][cH:4][n:5][cH:6]1)=[O:9]>>[CH3:1][c:2]1[cH:3][cH:4][n:5][cH:6][c:... | C[C@H](N)CN1CC(C)(C)OC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12.Cc1ccncc1C(=O)O | Cc1ccncc1C(=O)N[C@@H](C)CN1CC(C)(C)OC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCN1CCOC[C@H]1C(=O)Nc1cccc2c1[nH]c1cnccc12)c1cccnc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7].[C:8]-[C:9](-[C;D1;H3:10])-[NH2;D1;+0:11]>>[C:8]-[C:9](-[C;D1;H3:10])-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | 79 | [{"value": 79.0, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)[C@H]1N(CC(OC1)(C)C)C[C@H](C)NC(=O)C=1C=NC=CC1C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The desired compound was prepared according to Method E from (S)-4-((S)-2-Amino-propyl)-6,6-dimethyl-morpholine-3-carboxylic acid (6-chloro-9H-beta-carbolin-8-yl)-amide trifluoroacetate salt and 4-methyl-nicotinic acid in 79% yield.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccncc1.C1COCC[NH]1.c1ccc2c(c1)[nH]c1cnccc12 | HO- | null | null | null | C[C@H](N)CN1CC(C)(C)OC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12.Cc1ccncc1C(=O)O>>Cc1ccncc1C(=O)N[C@@H](C)CN1CC(C)(C)OC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-dc48c1aa823841a2aefa898d79268900 | CC(C)(C)OC(=O)N1CC(C)(C)OCC1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12>>CC1(C)CNC(C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1 | C(C)(C)(C)OC(=O)N1CC(OCC1C(NC=1C=C(C=C2C=3C=CN=CC3NC12)Cl)=O)(C)C.Cl.CCOCC>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)C1NCC(OC1)(C)C | CC(C)(C)OC(=O)[N:5]1[CH2:4][C:2]([CH3:1])([CH3:3])[O:25][CH2:24][CH:6]1[C:7](=[O:8])[NH:9][c:10]1[cH:11][c:12]([Cl:13])[cH:14][c:15]2[c:16]1[nH:17][c:18]1[cH:19][n:20][cH:21][cH:22][c:23]21>>[CH3:1][C:2]1([CH3:3])[CH2:4][NH:5][CH:6]([C:7](=[O:8])[NH:9][c:10]2[cH:11][c:12]([Cl:13])[cH:14][c:15]3[c:16]2[nH:17][c:18]2[cH:... | CC(C)(C)OC(=O)N1CC(C)(C)OCC1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 | CC1(C)CNC(C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1 | null | null | CO.O1CCOCC1 | Reduction | Boc amine deprotection | 711003132a3fa45641804f0f1112f2c6083a93e7723a03dc1bfa10a86d322b68 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=C(Nc1cccc2c1[nH]c1cnccc12)C1COCCN1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#8:4]-[C:5]-[C:6]-1-[C:7](=[O;D1;H0:8])-[#7:9]-[c:10]:[c:11]:[#7;a:12]>>[#7;a:12]:[c:11]:[c:10]-[#7:9]-[C:7](=[O;D1;H0:8])-[C:6]1-[C:5]-[#8:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1 | 119.2 | [{"value": 99.0, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)C1NCC(OC1)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 119.2, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)C1NCC(OC1)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a clear brown solution of 5-(6-chloro-9H-β-carbolin-8-ylcarbamoyl)-2,2-dimethyl-morpholine-4-carboxylic acid tert-butyl ester (10.4 g, 22.7 mmol) in methanol (41 mL) was added HCl in dioxane (4M, 91 mL). The reaction was stirred for 30 minutes at room temperature, during which time a pale brown precipitate began to ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1COCC[NH]1 | C1COCCN1 | C1COCCN1.c1ccc2c(c1)[nH]c1cnccc12 | HO- | CO.O1CCOCC1 | null | 0.5 | CC(C)(C)OC(=O)N1CC(C)(C)OCC1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12>CO.O1CCOCC1>CC1(C)CNC(C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-ff9c6f32cd5a4c24819f000ea55e2c8b | CC(C)(C)OC(=O)N1CC(C)(C)OCC1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12.CCC(C=O)NC(=O)OC(C)(C)C>>CCC(N)CN1CC(C)(C)OCC1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 | C(C)(C)(C)OC(=O)N1CC(OCC1C(NC=1C=C(C=C2C=3C=CN=CC3NC12)Cl)=O)(C)C.C(C)(C)(C)OC(NC(CC)C=O)=O>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)C1N(CC(OC1)(C)C)CC(CC)N | CC(C)(C)OC(=O)[N:6]1[CH2:7][C:8]([CH3:9])([CH3:10])[O:11][CH2:12][CH:13]1[C:14](=[O:15])[NH:16][c:17]1[cH:18][c:19]([Cl:20])[cH:21][c:22]2[c:23]1[nH:24][c:25]1[cH:26][n:27][cH:28][cH:29][c:30]21.CC(C)(C)OC(=O)[NH:4][CH:3]([CH2:2][CH3:1])[CH:5]=O>>[CH3:1][CH2:2][CH:3]([NH2:4])[CH2:5][N:6]1[CH2:7][C:8]([CH3:9])([CH3:10])... | CC(C)(C)OC(=O)N1CC(C)(C)OCC1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12.CCC(C=O)NC(=O)OC(C)(C)C | CCC(N)CN1CC(C)(C)OCC1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | c22af3bcded745a2ef0ab806662eb69a5ce6d90965df4d21f23275b1defe0c0c | 60a50d1b1b66a3cdcbad6664ebf06a1f4154a3f50ef2ff881074ba8a50b0b949 | O=C(Nc1cccc2c1[nH]c1cnccc12)C1COCCN1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#8:4]-[C:5]-[C:6]-1-[C:7](=[O;D1;H0:8])-[#7:9]-[c:10]:[c:11]:[#7;a:12].C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:13]-[C:14](-[C:15])-[CH;D2;+0:16]=O>>[#7;a:12]:[c:11]:[c:10]-[#7:9]-[C:7](=[O;D1;H0:8])-[C:6]1-[C:5]-[#8:4]-[C:3]-[C:2]-[N;H0;D3;+0:1]-1-[CH2;D2;+0:16]-[C:14](-[C:15])-[N... | null | [] | null | null | null | null | Method C was followed, using 5-(6-chloro-9H-β-carbolin-8-ylcarbamoyl)-2,2-dimethyl-morpholine-4-carboxylic acid tert-butyl ester and the appropriate aldehyde, (1-formyl-propyl)-carbamic acid tert-butyl ester.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Carbamic ester.Carbamic ester.Ether.Ether.Boc.Boc | Primary amine.Tertiary amine | C1COCC[NH]1 | C1COCC[NH]1 | C1COCC[NH]1.c1ccc2c(c1)[nH]c1cnccc12 | HO- | null | null | null | CC(C)(C)OC(=O)N1CC(C)(C)OCC1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12.CCC(C=O)NC(=O)OC(C)(C)C>>CCC(N)CN1CC(C)(C)OCC1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-86d07ec1acad4deaa6bd9c111eed8bdd | CCC(N)CN1CC(C)(C)OCC1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12.Cc1ncccc1C(=O)O>>CCC(CN1CC(C)(C)OCC1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12)NC(=O)c1cccnc1C | ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)C1N(CC(OC1)(C)C)CC(CC)N.CC1=C(C(=O)O)C=CC=N1.CCN=C=NCCCN(C)C>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)C1N(CC(OC1)(C)C)CC(CC)NC(=O)C=1C(=NC=CC1)C | [CH3:1][CH2:2][CH:3]([CH2:4][N:5]1[CH2:6][C:7]([CH3:8])([CH3:9])[O:10][CH2:11][CH:12]1[C:13](=[O:14])[NH:15][c:16]1[cH:17][c:18]([Cl:19])[cH:20][c:21]2[c:22]1[nH:23][c:24]1[cH:25][n:26][cH:27][cH:28][c:29]21)[NH2:30].O[C:31](=[O:32])[c:33]1[cH:34][cH:35][cH:36][n:37][c:38]1[CH3:39]>>[CH3:1][CH2:2][CH:3]([CH2:4][N:5]1[C... | CCC(N)CN1CC(C)(C)OCC1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12.Cc1ncccc1C(=O)O | CCC(CN1CC(C)(C)OCC1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12)NC(=O)c1cccnc1C | null | null | O.N1=CC=CC=C1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCN1CCOCC1C(=O)Nc1cccc2c1[nH]c1cnccc12)c1cccnc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[C;D1;H3:6]):[#7;a:7]:[c:8].[C:9]-[C:10](-[C:11])-[NH2;D1;+0:12]>>[C:9]-[C:10](-[C:11])-[NH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[C;D1;H3:6]):[#7;a:7]:[c:8] | 80.5 | [{"value": 71.0, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)C1N(CC(OC1)(C)C)CC(CC)NC(=O)C=1C(=NC=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.5, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)C1N(CC(OC1)(C)C)CC(CC)NC(=O)C=1C(=NC=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": fal... | null | null | 8 | HOUR | To a solution of 4-(2-amino-butyl)-6,6-dimethyl-morpholine-3-carboxylic acid (6-chloro-9H-β-carbolin-8-yl)-amide (100 mg, 0.233 mmol) in pyridine (4 mL) was added 2-methyl-nicotinic acid (38.4 mg, 0.280 mmol) and EDCI (71.5 mg, 0.373 mmol). The solution was stirred overnight at room temperature, then diluted with water... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1COCC[NH]1.c1ccc2c(c1)[nH]c1cnccc12.c1ccncc1 | HO- | O.N1=CC=CC=C1 | null | 8 | CCC(N)CN1CC(C)(C)OCC1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12.Cc1ncccc1C(=O)O>O.N1=CC=CC=C1>CCC(CN1CC(C)(C)OCC1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12)NC(=O)c1cccnc1C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-2cf74021c1fb4b08a135f3920f25b9d6 | CC(C)(C)OC(=O)N1CC(C)(C)OCC1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12.CC(C)C(C=O)NC(=O)OC(C)(C)C>>CC(C)C(N)CN1CC(C)(C)OCC1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 | C(C)(C)(C)OC(=O)N1CC(OCC1C(NC=1C=C(C=C2C=3C=CN=CC3NC12)Cl)=O)(C)C.C(C)(C)(C)OC(NC(C(C)C)C=O)=O>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)C1N(CC(OC1)(C)C)CC(C(C)C)N | CC(C)(C)OC(=O)[N:7]1[CH2:8][C:9]([CH3:10])([CH3:11])[O:12][CH2:13][CH:14]1[C:15](=[O:16])[NH:17][c:18]1[cH:19][c:20]([Cl:21])[cH:22][c:23]2[c:24]1[nH:25][c:26]1[cH:27][n:28][cH:29][cH:30][c:31]21.CC(C)(C)OC(=O)[NH:5][CH:4]([CH:2]([CH3:1])[CH3:3])[CH:6]=O>>[CH3:1][CH:2]([CH3:3])[CH:4]([NH2:5])[CH2:6][N:7]1[CH2:8][C:9]([... | CC(C)(C)OC(=O)N1CC(C)(C)OCC1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12.CC(C)C(C=O)NC(=O)OC(C)(C)C | CC(C)C(N)CN1CC(C)(C)OCC1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | c22af3bcded745a2ef0ab806662eb69a5ce6d90965df4d21f23275b1defe0c0c | 60a50d1b1b66a3cdcbad6664ebf06a1f4154a3f50ef2ff881074ba8a50b0b949 | O=C(Nc1cccc2c1[nH]c1cnccc12)C1COCCN1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#8:4]-[C:5]-[C:6]-1-[C:7](=[O;D1;H0:8])-[#7:9]-[c:10]:[c:11]:[#7;a:12].C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:13]-[C:14](-[C:15])-[CH;D2;+0:16]=O>>[#7;a:12]:[c:11]:[c:10]-[#7:9]-[C:7](=[O;D1;H0:8])-[C:6]1-[C:5]-[#8:4]-[C:3]-[C:2]-[N;H0;D3;+0:1]-1-[CH2;D2;+0:16]-[C:14](-[C:15])-[N... | null | [] | null | null | null | null | Method C was followed, using 5-(6-chloro-9H-β-carbolin-8-ylcarbamoyl)-2,2-dimethyl-morpholine-4-carboxylic acid tert-butyl ester and the appropriate aldehyde, (1-formyl-2-methyl-propyl)-carbamic acid tert-butyl ester.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Carbamic ester.Carbamic ester.Ether.Ether.Boc.Boc | Primary amine.Tertiary amine | C1COCC[NH]1 | C1COCC[NH]1 | C1COCC[NH]1.c1ccc2c(c1)[nH]c1cnccc12 | HO- | null | null | null | CC(C)(C)OC(=O)N1CC(C)(C)OCC1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12.CC(C)C(C=O)NC(=O)OC(C)(C)C>>CC(C)C(N)CN1CC(C)(C)OCC1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-8c05c8b7442241ab9e8f8efb8e990e3f | CC(C)C(N)CN1CC(C)(C)OCC1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12.Cc1ncccc1C(=O)O>>Cc1ncccc1C(=O)NC(CN1CC(C)(C)OCC1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12)C(C)C | ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)C1N(CC(OC1)(C)C)CC(C(C)C)N.CC1=C(C(=O)O)C=CC=N1.CCN=C=NCCCN(C)C>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)C1N(CC(OC1)(C)C)CC(C(C)C)NC(=O)C=1C(=NC=CC1)C | [NH2:10][CH:11]([CH2:12][N:13]1[CH2:14][C:15]([CH3:16])([CH3:17])[O:18][CH2:19][CH:20]1[C:21](=[O:22])[NH:23][c:24]1[cH:25][c:26]([Cl:27])[cH:28][c:29]2[c:30]1[nH:31][c:32]1[cH:33][n:34][cH:35][cH:36][c:37]21)[CH:38]([CH3:39])[CH3:40].O[C:8]([c:7]1[c:2]([CH3:1])[n:3][cH:4][cH:5][cH:6]1)=[O:9]>>[CH3:1][c:2]1[n:3][cH:4][... | CC(C)C(N)CN1CC(C)(C)OCC1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12.Cc1ncccc1C(=O)O | Cc1ncccc1C(=O)NC(CN1CC(C)(C)OCC1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12)C(C)C | null | null | CCOC(=O)C.O.N1=CC=CC=C1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCN1CCOCC1C(=O)Nc1cccc2c1[nH]c1cnccc12)c1cccnc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[C;D1;H3:6]):[#7;a:7]:[c:8].[C:9]-[C:10](-[C:11])-[NH2;D1;+0:12]>>[C:9]-[C:10](-[C:11])-[NH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[C;D1;H3:6]):[#7;a:7]:[c:8] | 77 | [{"value": 77.0, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)C1N(CC(OC1)(C)C)CC(C(C)C)NC(=O)C=1C(=NC=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.7, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)C1N(CC(OC1)(C)C)CC(C(C)C)NC(=O)C=1C(=NC=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired... | null | null | 6.5 | HOUR | To a solution of 4-(2-amino-3-methyl-butyl)-6,6-dimethyl-morpholine-3-carboxylic acid (6-chloro-9H-β-carbolin-8-yl)-amide (1.47 g, 3.31 mmol) in pyridine (35 mL) was added 2-methyl-nicotinic acid (544 mg, 3.97 mmol) and EDCI (1.02 g, 5.30 mmol). The solution was stirred 6.5 hours at room temperature, then diluted with ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccncc1.C1COCC[NH]1.c1ccc2c(c1)[nH]c1cnccc12 | HO- | CCOC(=O)C.O.N1=CC=CC=C1 | null | 6.5 | CC(C)C(N)CN1CC(C)(C)OCC1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12.Cc1ncccc1C(=O)O>CCOC(=O)C.O.N1=CC=CC=C1>Cc1ncccc1C(=O)NC(CN1CC(C)(C)OCC1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12)C(C)C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-de19231c6bd74670afea944e8f43a29e | C[C@@H](CN1CC(C)(C)OC[C@H]1C(=O)O)NC(=O)OC(C)(C)C.Cc1cncc2[nH]c3c(N)cc(Cl)cc3c12>>Cc1cncc2[nH]c3c(NC(=O)[C@@H]4COC(C)(C)CN4C[C@H](C)NC(=O)OC(C)(C)C)cc(Cl)cc3c12 | CCN=C=NCCCN(C)C.C(C)(C)(C)OC(=O)N[C@H](CN1[C@@H](COC(C1)(C)C)C(=O)O)C.CC1(OC[C@H](NC1)C(=O)O)C.ClC=1C=C2C=3C(=CN=CC3NC2=C(C1)N)C>>C(C)(C)(C)OC(N[C@H](CN1CC(OC[C@H]1C(NC=1C=C(C=C2C=3C(=CN=CC3NC12)C)Cl)=O)(C)C)C)=O | O[C:11](=[O:12])[C@@H:13]1[CH2:14][O:15][C:16]([CH3:17])([CH3:18])[CH2:19][N:20]1[CH2:21][C@H:22]([CH3:23])[NH:24][C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31].[CH3:1][c:2]1[cH:3][n:4][cH:5][c:6]2[nH:7][c:8]3[c:9]([NH2:10])[cH:32][c:33]([Cl:34])[cH:35][c:36]3[c:37]12>>[CH3:1][c:2]1[cH:3][n:4][cH:5][c:6]2[nH:7... | C[C@@H](CN1CC(C)(C)OC[C@H]1C(=O)O)NC(=O)OC(C)(C)C.Cc1cncc2[nH]c3c(N)cc(Cl)cc3c12 | Cc1cncc2[nH]c3c(NC(=O)[C@@H]4COC(C)(C)CN4C[C@H](C)NC(=O)OC(C)(C)C)cc(Cl)cc3c12 | null | null | CO.C(Cl)Cl.N1=CC=CC=C1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1cccc2c1[nH]c1cnccc12)[C@@H]1COCCN1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4]-[#8:5])-[#7:6](-[C:7])-[C:8].[#7;a:9]:[c:10]:[c:11]:[#7;a:12]:[c:13](:[c:14]):[c:15](-[NH2;D1;+0:16]):[c:17]>>[#7;a:9]:[c:10]:[c:11]:[#7;a:12]:[c:13](:[c:14]):[c:15](-[NH;D2;+0:16]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4]-[#8:5])-[#7:6](-[C:7])-[C:8]):[c:17] | 62.7 | [{"value": 62.7, "product": "C(C)(C)(C)OC(N[C@H](CN1CC(OC[C@H]1C(NC=1C=C(C=C2C=3C(=CN=CC3NC12)C)Cl)=O)(C)C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of (S)-4-((S)-2-tert-butoxycarbonylamino-propyl)-6,6-dimethyl-morpholine-3-carboxylic acid (3.316 g, 10.5 mmol) (prepared by reductively alkylating (S)-6,6-dimethyl-morpholine-3-carboxylic acid with N-(tert-butoxycarbonyl)-L-alanal) in anhydrous pyridine (75 mL) was stirred at room temperature. 6-chloro-4-me... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1COCC[NH]1.c1ccc2c(c1)[nH]c1cnccc12 | HO- | CO.C(Cl)Cl.N1=CC=CC=C1 | null | null | C[C@@H](CN1CC(C)(C)OC[C@H]1C(=O)O)NC(=O)OC(C)(C)C.Cc1cncc2[nH]c3c(N)cc(Cl)cc3c12>CO.C(Cl)Cl.N1=CC=CC=C1>Cc1cncc2[nH]c3c(NC(=O)[C@@H]4COC(C)(C)CN4C[C@H](C)NC(=O)OC(C)(C)C)cc(Cl)cc3c12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-89abf249a0f54f24b8c894f543473385 | CCC[CH2][Sn]([Cl])([CH2]CCC)[CH2]CCC.Fc1cncc(F)c1>>CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1c(F)cncc1F | C(CCC)[Sn](CCCC)(CCCC)Cl.C(CCC)[Li].C(C)(C)NC(C)C.FC=1C=NC=C(C1)F>>FC=1C=NC=C(C1[Sn](CCCC)(CCCC)CCCC)F | [Cl][Sn:5]([CH2:4][CH2:3][CH2:2][CH3:1])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:10][CH2:11][CH2:12][CH3:13].[cH:14]1[c:15]([F:16])[cH:17][n:18][cH:19][c:20]1[F:21]>>[CH3:1][CH2:2][CH2:3][CH2:4][Sn:5]([CH2:6][CH2:7][CH2:8][CH3:9])([CH2:10][CH2:11][CH2:12][CH3:13])[c:14]1[c:15]([F:16])[cH:17][n:18][cH:19][c:20]1[F:21] | CCC[CH2][Sn]([Cl])([CH2]CCC)[CH2]CCC.Fc1cncc(F)c1 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1c(F)cncc1F | null | null | C1CCOC1.O | Functional Group Interconversion | OtherReaction | 157ed86a47fdc4e2a8a8cbaf40c9e8c836526372fc356d6404550bda901a11a9 | 8ed099106fd03cd2d2d78800a2ee5fc34a9ebd85fa643ab7cdafec1855cc2f69 | c1ccncc1 | [C:1]-[C:2]-[Sn;H0;D4;+0:3](-[Cl])(-[C:4]-[C:5])-[C:6]-[C:7].[F;D1;H0:8]-[c:9]1:[c:10]:[#7;a:11]:[c:12]:[c:13](-[F;D1;H0:14]):[cH;D2;+0:15]:1>>[C:1]-[C:2]-[Sn;H0;D4;+0:3](-[C:4]-[C:5])(-[C:6]-[C:7])-[c;H0;D3;+0:15]1:[c:9](-[F;D1;H0:8]):[c:10]:[#7;a:11]:[c:12]:[c:13]:1-[F;D1;H0:14] | 89.5 | [{"value": 88.0, "product": "FC=1C=NC=C(C1[Sn](CCCC)(CCCC)CCCC)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.5, "product": "FC=1C=NC=C(C1[Sn](CCCC)(CCCC)CCCC)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 30 | MINUTE | n-Butyl lithium (1.0 eq, 76 mmol, 47.6 mL, 1.6 M in hexanes) was added via dropping funnel to a solution of diisopropylamine (1.05 eq, 80 mmol, 11.2 mL) in THF (300 mL) at −78° C. under nitrogen (N2). The solution was stirred for 30 min at −78° C., then a solution of 3,5-difluoropyridine (1.05 eq, 80 mmol, 9.2 g) in TH... | 10.6084/m9.figshare.5104873.v1 | null | Tin | Tin | c1ccncc1 | c1ccncc1 | c1ccncc1 | HCl | C1CCOC1.O | -78 | 0.5 | CCC[CH2][Sn]([Cl])([CH2]CCC)[CH2]CCC.Fc1cncc(F)c1>C1CCOC1.O>CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1c(F)cncc1F |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-981b4dc1e0c84bf89a142b850617dd70 | Fc1cncc2[nH]c3ccc(Cl)cc3c12>>O=[N+]([O-])c1cc(Cl)cc2c1[nH]c1cncc(F)c12 | C([O-])(O)=O.[Na+].[N+](=O)([O-])[O-].[Na+].ClC=1C=C2C=3C(=CN=CC3NC2=CC1)F.CO>>ClC=1C=C2C=3C(=CN=CC3NC2=C(C1)[N+](=O)[O-])F | [cH:4]1[cH:5][c:6]([Cl:7])[cH:8][c:9]2[c:10]1[nH:11][c:12]1[cH:13][n:14][cH:15][c:16]([F:17])[c:18]21>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([Cl:7])[cH:8][c:9]2[c:10]1[nH:11][c:12]1[cH:13][n:14][cH:15][c:16]([F:17])[c:18]21 | Fc1cncc2[nH]c3ccc(Cl)cc3c12 | O=[N+]([O-])c1cc(Cl)cc2c1[nH]c1cncc(F)c12 | null | null | FC(C(=O)O)(F)F | Functional Group Addition | OtherReaction | 3933ccedcb89087e8369e8b96a6fdb15b3900ebc2ce7ca0a1f7fac4c3c421e4c | 22f3183026a2d99c91ec0c53f0059a15c8421016bd62c8ab45281362b96dc686 | c1ccc2c(c1)[nH]c1cnccc12 | [#7;a:1]:[c:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[#7;a:1]:[c:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c;H0;D3;+0:7](-[#7;+:10](-[O;-;D1;H0:11])=[O;D1;H0:12]):[c:8]:[c:9] | 102.2 | [{"value": 102.2, "product": "ClC=1C=C2C=3C(=CN=CC3NC2=C(C1)[N+](=O)[O-])F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 15 | MINUTE | Sodium nitrate (1.5 eq, 53 mmol, 4.5 g) was added portionwise to a solution of Intermediate 65 (1.0 eq, 35 mmol, 7.8 g) in trifluoroacetic acid (200 mL) and the resulting mixture heated at 70° C. for 3 h. After cooling to RT the trifluoroacetic acid was removed on a rotary evaporator to afford a crude solid which was s... | 10.6084/m9.figshare.5104873.v1 | null | null | Nitro group | c1ccc2c(c1)[nH]c1cnccc12 | c1ccc2c(c1)[nH]c1cnccc12 | c1ccc2c(c1)[nH]c1cnccc12 | Other | FC(C(=O)O)(F)F | 70 | 0.25 | Fc1cncc2[nH]c3ccc(Cl)cc3c12>FC(C(=O)O)(F)F>O=[N+]([O-])c1cc(Cl)cc2c1[nH]c1cncc(F)c12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-534f3688ab12471ab15900e5214ec6b6 | O=[N+]([O-])c1cc(Cl)cc2c1[nH]c1cncc(F)c12>>Nc1cc(Cl)cc2c1[nH]c1cncc(F)c12 | ClC=1C=C2C=3C(=CN=CC3NC2=C(C1)[N+](=O)[O-])F.C(=O)[O-].[NH4+].C([O-])(O)=O.[Na+].[Cl-].[Na+]>>ClC=1C=C2C=3C(=CN=CC3NC2=C(C1)N)F | O=[N+:1]([O-])[c:2]1[cH:3][c:4]([Cl:5])[cH:6][c:7]2[c:8]1[nH:9][c:10]1[cH:11][n:12][cH:13][c:14]([F:15])[c:16]21>>[NH2:1][c:2]1[cH:3][c:4]([Cl:5])[cH:6][c:7]2[c:8]1[nH:9][c:10]1[cH:11][n:12][cH:13][c:14]([F:15])[c:16]21 | O=[N+]([O-])c1cc(Cl)cc2c1[nH]c1cncc(F)c12 | Nc1cc(Cl)cc2c1[nH]c1cncc(F)c12 | null | null | CO.C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2c(c1)[nH]c1cnccc12 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]:[c:8]:[#7;a:9]>>[#7;a:9]:[c:8]:[c:7]:[#7;a:6]:[c:4](:[c:5]):[c:2](-[NH2;D1;+0:1]):[c:3] | 70.3 | [{"value": 70.0, "product": "ClC=1C=C2C=3C(=CN=CC3NC2=C(C1)N)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.3, "product": "ClC=1C=C2C=3C(=CN=CC3NC2=C(C1)N)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | 15 | MINUTE | Sulfated platinum (˜0.1 eq, 1 g) was added to a suspension of 6-chloro-4-fluoro-8-nitro-9H-β-carboline (1.0 eq, 35 mmol, 9.3 g) and ammonium formate (3.0 eq, 105 mmol, 6.6 g) in ethanol (175 mL) and the resulting mixture heated at 75° C. for 4 h. After cooling to RT the mixture was filtered through a short plug of Celi... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2c(c1)[nH]c1cnccc12 | Other | CO.C(C)O | 75 | 0.25 | O=[N+]([O-])c1cc(Cl)cc2c1[nH]c1cncc(F)c12>CO.C(C)O>Nc1cc(Cl)cc2c1[nH]c1cncc(F)c12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-5063a34e8e444b9699047499e466ff58 | CC1(C)CN[C@H](C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1.O=CC(=O)O>>CC1(C)CN(CC(=O)O)[C@H](C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1 | ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)[C@H]1NCC(OC1)(C)C.C(C)N(CC)CC.C(#N)[BH3-].[Na+].C(C=O)(=O)O>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)[C@@H]1COC(CN1CC(=O)O)(C)C | [CH3:1][C:2]1([CH3:3])[CH2:4][NH:5][C@H:10]([C:11](=[O:12])[NH:13][c:14]2[cH:15][c:16]([Cl:17])[cH:18][c:19]3[c:20]2[nH:21][c:22]2[cH:23][n:24][cH:25][cH:26][c:27]32)[CH2:28][O:29]1.O=[CH:6][C:7](=[O:8])[OH:9]>>[CH3:1][C:2]1([CH3:3])[CH2:4][N:5]([CH2:6][C:7](=[O:8])[OH:9])[C@H:10]([C:11](=[O:12])[NH:13][c:14]2[cH:15][c... | CC1(C)CN[C@H](C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1.O=CC(=O)O | CC1(C)CN(CC(=O)O)[C@H](C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1 | null | null | CO.O | Heteroatom Alkylation and Arylation | reductive amination | 073d98e7dcd77aafeef71a76da7e61b2751c934600f6fff04db700a08f3e4453 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | O=C(Nc1cccc2c1[nH]c1cnccc12)[C@@H]1COCCN1 | O=[CH;D2;+0:1]-[C:2](=[O;D1;H0:3])-[O;D1;H1:4].[#7;a:5]:[c:6]:[c:7]-[#7:8]-[C:9](=[O;D1;H0:10])-[C:11]1-[C:12]-[#8:13]-[C:14]-[C:15]-[NH;D2;+0:16]-1>>[#7;a:5]:[c:6]:[c:7]-[#7:8]-[C:9](=[O;D1;H0:10])-[C:11]1-[C:12]-[#8:13]-[C:14]-[C:15]-[N;H0;D3;+0:16]-1-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[O;D1;H1:4] | 72 | [{"value": 71.0, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)[C@@H]1COC(CN1CC(=O)O)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.0, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)[C@@H]1COC(CN1CC(=O)O)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | To a suspension of (S)-6,6-Dimethyl-morpholine-3-carboxylic acid (6-chloro-9H-beta-carbolin-8-yl)-amide (2.6 g, 6.0 mmoles) in 60 ml of methanol was added 1.7 ml of triethylamine (2.0 eq.), sodium cyanoborohydride (575 mg, 9.1 mmoles) and glyoxylic acid (780 mg, 8.5 mmoles). The reaction mixture was stirred at ambient ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1COCCN1 | C1COCC[NH]1 | C1COCC[NH]1.c1ccc2c(c1)[nH]c1cnccc12 | Other | CO.O | null | 1.5 | CC1(C)CN[C@H](C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1.O=CC(=O)O>CO.O>CC1(C)CN(CC(=O)O)[C@H](C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-1192430b6c8e43849ca85c195b6c749f | C1CCNC1.CC1(C)CN(CC(=O)O)[C@H](C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1>>CC1(C)CN(CC(=O)N2CCCC2)[C@H](C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1 | ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)[C@@H]1COC(CN1CC(=O)O)(C)C.N1CCCC1>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)[C@H]1N(CC(OC1)(C)C)CC(N1CCCC1)=O | [NH:9]1[CH2:10][CH2:11][CH2:12][CH2:13]1.O[C:7]([CH2:6][N:5]1[CH2:4][C:2]([CH3:1])([CH3:3])[O:33][CH2:32][C@H:14]1[C:15](=[O:16])[NH:17][c:18]1[cH:19][c:20]([Cl:21])[cH:22][c:23]2[c:24]1[nH:25][c:26]1[cH:27][n:28][cH:29][cH:30][c:31]21)=[O:8]>>[CH3:1][C:2]1([CH3:3])[CH2:4][N:5]([CH2:6][C:7](=[O:8])[N:9]2[CH2:10][CH2:11... | C1CCNC1.CC1(C)CN(CC(=O)O)[C@H](C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1 | CC1(C)CN(CC(=O)N2CCCC2)[C@H](C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | a590d96426a2fbaed42913d9daf8a16471a16de4978200f1d35a30a10009ebe7 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(Nc1cccc2c1[nH]c1cnccc12)[C@@H]1COCCN1CC(=O)N1CCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4].[C:5]1-[C:6]-[C:7]-[C:8]-[NH;D2;+0:9]-1>>[#7:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:9]1-[C:5]-[C:6]-[C:7]-[C:8]-1 | 82 | [{"value": 82.0, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)[C@H]1N(CC(OC1)(C)C)CC(N1CCCC1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The desired compound was prepared according to Method F from [(S)-5-(6-Chloro-9H-beta-carbolin-8-ylcarbamoyl)-2,2-dimethyl-morpholin-4-yl]-acetic acid and pyrrolidine in 82% yield.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCNC1 | C1CC[NH]C1 | C1COCC[NH]1.C1CC[NH]C1.c1ccc2c(c1)[nH]c1cnccc12 | HO- | null | null | null | C1CCNC1.CC1(C)CN(CC(=O)O)[C@H](C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1>>CC1(C)CN(CC(=O)N2CCCC2)[C@H](C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-86725e0e521e4e15b28a05337dd003f8 | C1CCNCC1.CC1(C)CN(CC(=O)O)[C@H](C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1>>CC1(C)CN(CC(=O)N2CCCCC2)[C@H](C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1 | ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)[C@@H]1COC(CN1CC(=O)O)(C)C.N1CCCCC1>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)[C@H]1N(CC(OC1)(C)C)CC(N1CCCCC1)=O | [NH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1.O[C:7]([CH2:6][N:5]1[CH2:4][C:2]([CH3:1])([CH3:3])[O:34][CH2:33][C@H:15]1[C:16](=[O:17])[NH:18][c:19]1[cH:20][c:21]([Cl:22])[cH:23][c:24]2[c:25]1[nH:26][c:27]1[cH:28][n:29][cH:30][cH:31][c:32]21)=[O:8]>>[CH3:1][C:2]1([CH3:3])[CH2:4][N:5]([CH2:6][C:7](=[O:8])[N:9]2[CH2:10... | C1CCNCC1.CC1(C)CN(CC(=O)O)[C@H](C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1 | CC1(C)CN(CC(=O)N2CCCCC2)[C@H](C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | fbfce93ec1ece674255bb96c5cec09ad611382b41cf117dfe580015e21744a71 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(Nc1cccc2c1[nH]c1cnccc12)[C@@H]1COCCN1CC(=O)N1CCCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[#7:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:7](-[C:6]-[C:5])-[C:8]-[C:9] | 90 | [{"value": 90.0, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)[C@H]1N(CC(OC1)(C)C)CC(N1CCCCC1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The desired compound was prepared according to Method F from [(S)-5-(6-Chloro-9H-beta-carbolin-8-ylcarbamoyl)-2,2-dimethyl-morpholin-4-yl]-acetic acid and piperidine in 90% yield.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | C1COCC[NH]1.C1CC[NH]CC1.c1ccc2c(c1)[nH]c1cnccc12 | HO- | null | null | null | C1CCNCC1.CC1(C)CN(CC(=O)O)[C@H](C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1>>CC1(C)CN(CC(=O)N2CCCCC2)[C@H](C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-bfedcd2a84d44b00a677751687926cb9 | C1COCCN1.CC1(C)CN(CC(=O)O)[C@H](C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1>>CC1(C)CN(CC(=O)N2CCOCC2)[C@H](C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1 | ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)[C@@H]1COC(CN1CC(=O)O)(C)C.N1CCOCC1>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)[C@H]1N(CC(OC1)(C)C)CC(=O)N1CCOCC1 | [NH:9]1[CH2:10][CH2:11][O:12][CH2:13][CH2:14]1.O[C:7]([CH2:6][N:5]1[CH2:4][C:2]([CH3:1])([CH3:3])[O:34][CH2:33][C@H:15]1[C:16](=[O:17])[NH:18][c:19]1[cH:20][c:21]([Cl:22])[cH:23][c:24]2[c:25]1[nH:26][c:27]1[cH:28][n:29][cH:30][cH:31][c:32]21)=[O:8]>>[CH3:1][C:2]1([CH3:3])[CH2:4][N:5]([CH2:6][C:7](=[O:8])[N:9]2[CH2:10][... | C1COCCN1.CC1(C)CN(CC(=O)O)[C@H](C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1 | CC1(C)CN(CC(=O)N2CCOCC2)[C@H](C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | 2ef483949e7ba3e5f888cf14cdce25fa611f75be09fdf1854a473be519821b59 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(Nc1cccc2c1[nH]c1cnccc12)[C@@H]1COCCN1CC(=O)N1CCOCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4].[#8:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[#7:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#8:5]-[C:10]-[C:9]-1 | 86 | [{"value": 86.0, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)[C@H]1N(CC(OC1)(C)C)CC(=O)N1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The desired compound was prepared according to Method F from [(S)-5-(6-Chloro-9H-beta-carbolin-8-ylcarbamoyl)-2,2-dimethyl-morpholin-4-yl]-acetic acid and morpholine in 86% yield.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1COCCN1 | C1COCC[NH]1 | C1COCC[NH]1.C1COCC[NH]1.c1ccc2c(c1)[nH]c1cnccc12 | HO- | null | null | null | C1COCCN1.CC1(C)CN(CC(=O)O)[C@H](C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1>>CC1(C)CN(CC(=O)N2CCOCC2)[C@H](C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-fdc31d4a04884c65be3b0a14626b16d8 | CC1(C)CN(CC(=O)O)[C@H](C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1.CNCCO>>CN(CCO)C(=O)CN1CC(C)(C)OC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 | ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)[C@@H]1COC(CN1CC(=O)O)(C)C.CNCCO>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)[C@H]1N(CC(OC1)(C)C)CC(N(C)CCO)=O | O[C:6](=[O:7])[CH2:8][N:9]1[CH2:10][C:11]([CH3:12])([CH3:13])[O:14][CH2:15][C@H:16]1[C:17](=[O:18])[NH:19][c:20]1[cH:21][c:22]([Cl:23])[cH:24][c:25]2[c:26]1[nH:27][c:28]1[cH:29][n:30][cH:31][cH:32][c:33]21.[CH3:1][NH:2][CH2:3][CH2:4][OH:5]>>[CH3:1][N:2]([CH2:3][CH2:4][OH:5])[C:6](=[O:7])[CH2:8][N:9]1[CH2:10][C:11]([CH3... | CC1(C)CN(CC(=O)O)[C@H](C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1.CNCCO | CN(CCO)C(=O)CN1CC(C)(C)OC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(Nc1cccc2c1[nH]c1cnccc12)[C@@H]1COCCN1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C;D1;H3:8]>>[#7:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:7](-[C;D1;H3:8])-[C:6]-[C:5] | 55 | [{"value": 55.0, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)[C@H]1N(CC(OC1)(C)C)CC(N(C)CCO)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The desired compound was prepared according to Method F from [(S)-5-(6-Chloro-9H-beta-carbolin-8-ylcarbamoyl)-2,2-dimethyl-morpholin-4-yl]-acetic acid and 2-methylamino-ethanol in 55% yield.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | C1COCC[NH]1.c1ccc2c(c1)[nH]c1cnccc12 | HO- | null | null | null | CC1(C)CN(CC(=O)O)[C@H](C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1.CNCCO>>CN(CCO)C(=O)CN1CC(C)(C)OC[C@H]1C(=O)Nc1cc(Cl)cc2c1[nH]c1cnccc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-44c3725d926f4530a664ee1f3c677576 | CC1(C)CN(CC(=O)O)[C@H](C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1.Nc1cccnc1>>CC1(C)CN(CC(=O)Nc2cccnc2)[C@H](C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1 | ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)[C@@H]1COC(CN1CC(=O)O)(C)C.NC=1C=NC=CC1>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)[C@H]1N(CC(OC1)(C)C)CC(NC=1C=NC=CC1)=O | O[C:7]([CH2:6][N:5]1[CH2:4][C:2]([CH3:1])([CH3:3])[O:35][CH2:34][C@H:16]1[C:17](=[O:18])[NH:19][c:20]1[cH:21][c:22]([Cl:23])[cH:24][c:25]2[c:26]1[nH:27][c:28]1[cH:29][n:30][cH:31][cH:32][c:33]21)=[O:8].[NH2:9][c:10]1[cH:11][cH:12][cH:13][n:14][cH:15]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][N:5]([CH2:6][C:7](=[O:8])[NH:9][c:10]... | CC1(C)CN(CC(=O)O)[C@H](C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1.Nc1cccnc1 | CC1(C)CN(CC(=O)Nc2cccnc2)[C@H](C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CN1CCOC[C@H]1C(=O)Nc1cccc2c1[nH]c1cnccc12)Nc1cccnc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]:[#7;a:9]:[c:10]>>[#7:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8]:[#7;a:9]:[c:10] | 55 | [{"value": 55.0, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)[C@H]1N(CC(OC1)(C)C)CC(NC=1C=NC=CC1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The desired compound was prepared according to Method F from [(S)-5-(6-Chloro-9H-beta-carbolin-8-ylcarbamoyl)-2,2-dimethyl-morpholin-4-yl]-acetic acid and 3-aminopyridine. The product was isolated as hydrochloride salt in 55% yield.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1COCC[NH]1.c1ccncc1.c1ccc2c(c1)[nH]c1cnccc12 | HO- | null | null | null | CC1(C)CN(CC(=O)O)[C@H](C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1.Nc1cccnc1>>CC1(C)CN(CC(=O)Nc2cccnc2)[C@H](C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-5ff6e38a931646ee87264518ffe95579 | CC1(C)CN(CC(=O)O)[C@H](C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1.NCc1ccncc1>>CC1(C)CN(CC(=O)NCc2ccncc2)[C@H](C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1 | ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)[C@@H]1COC(CN1CC(=O)O)(C)C.NCC1=CC=NC=C1>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)[C@H]1N(CC(OC1)(C)C)CC(NCC1=CC=NC=C1)=O | O[C:7]([CH2:6][N:5]1[CH2:4][C:2]([CH3:1])([CH3:3])[O:36][CH2:35][C@H:17]1[C:18](=[O:19])[NH:20][c:21]1[cH:22][c:23]([Cl:24])[cH:25][c:26]2[c:27]1[nH:28][c:29]1[cH:30][n:31][cH:32][cH:33][c:34]21)=[O:8].[NH2:9][CH2:10][c:11]1[cH:12][cH:13][n:14][cH:15][cH:16]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][N:5]([CH2:6][C:7](=[O:8])[NH:... | CC1(C)CN(CC(=O)O)[C@H](C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1.NCc1ccncc1 | CC1(C)CN(CC(=O)NCc2ccncc2)[C@H](C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CN1CCOC[C@H]1C(=O)Nc1cccc2c1[nH]c1cnccc12)NCc1ccncc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4].[NH2;D1;+0:5]-[C:6]-[c:7]>>[#7:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[C:6]-[c:7] | 53 | [{"value": 53.0, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)[C@H]1N(CC(OC1)(C)C)CC(NCC1=CC=NC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The desired compound was prepared according to Method F from [(S)-5-(6-Chloro-9H-beta-carbolin-8-ylcarbamoyl)-2,2-dimethyl-morpholin-4-yl]-acetic acid and 4-(aminomethyl)pyridine. The product was isolated as hydrochloride salt in 53% yield.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1COCC[NH]1.c1ccncc1.c1ccc2c(c1)[nH]c1cnccc12 | HO- | null | null | null | CC1(C)CN(CC(=O)O)[C@H](C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1.NCc1ccncc1>>CC1(C)CN(CC(=O)NCc2ccncc2)[C@H](C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-33dc103cec324a1ca3caf890d6d35bbd | CC1(C)CN(CC(=O)O)C(C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1.OCC1CCNCC1>>CC1(C)CN(CC(=O)N2CCC(CO)CC2)C(C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1 | O.ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)C1COC(CN1CC(=O)O)(C)C.N1CCC(CC1)CO.C(CCl)Cl>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)C1N(CC(OC1)(C)C)CC(=O)N1CCC(CC1)CO | O[C:7]([CH2:6][N:5]1[CH2:4][C:2]([CH3:1])([CH3:3])[O:36][CH2:35][CH:17]1[C:18](=[O:19])[NH:20][c:21]1[cH:22][c:23]([Cl:24])[cH:25][c:26]2[c:27]1[nH:28][c:29]1[cH:30][n:31][cH:32][cH:33][c:34]21)=[O:8].[NH:9]1[CH2:10][CH2:11][CH:12]([CH2:13][OH:14])[CH2:15][CH2:16]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][N:5]([CH2:6][C:7](=[O:8... | CC1(C)CN(CC(=O)O)C(C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1.OCC1CCNCC1 | CC1(C)CN(CC(=O)N2CCC(CO)CC2)C(C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1 | null | null | N1=CC=CC=C1 | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | fbfce93ec1ece674255bb96c5cec09ad611382b41cf117dfe580015e21744a71 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(Nc1cccc2c1[nH]c1cnccc12)C1COCCN1CC(=O)N1CCCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[#7:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:7](-[C:6]-[C:5])-[C:8]-[C:9] | 62 | [{"value": 62.0, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)C1N(CC(OC1)(C)C)CC(=O)N1CCC(CC1)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.6, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)C1N(CC(OC1)(C)C)CC(=O)N1CCC(CC1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | [5-(6-Chloro-9H-beta-carbolin-8-ylcarbamoyl)-2,2-dimethyl-morpholin-4-yl]-acetic acid (200 mg, 0.48 mmol) and piperidin-4-yl-methanol (111 mg, 0.96 mmol) were dissolved in pyridine (4 mL). The resulting yellow solution was stirred at room temperature for 10 min and then EDC (184 mg, 0.96 mmol) was added in a single por... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | C1COCC[NH]1.C1CC[NH]CC1.c1ccc2c(c1)[nH]c1cnccc12 | HO- | N1=CC=CC=C1 | null | 0.166667 | CC1(C)CN(CC(=O)O)C(C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1.OCC1CCNCC1>N1=CC=CC=C1>CC1(C)CN(CC(=O)N2CCC(CO)CC2)C(C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-f451cb243ac244ca9c1117bdd2491195 | CC1(C)CN(CC(=O)O)C(C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1.CN1CCNCC1>>CN1CCN(C(=O)CN2CC(C)(C)OCC2C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CC1 | ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)C1COC(CN1CC(=O)O)(C)C.CN1CCNCC1>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)C1N(CC(OC1)(C)C)CC(=O)N1CCN(CC1)C | O[C:6](=[O:7])[CH2:8][N:9]1[CH2:10][C:11]([CH3:12])([CH3:13])[O:14][CH2:15][CH:16]1[C:17](=[O:18])[NH:19][c:20]1[cH:21][c:22]([Cl:23])[cH:24][c:25]2[c:26]1[nH:27][c:28]1[cH:29][n:30][cH:31][cH:32][c:33]21.[CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:34][CH2:35]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[CH2:8][N:9]2[CH2... | CC1(C)CN(CC(=O)O)C(C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1.CN1CCNCC1 | CN1CCN(C(=O)CN2CC(C)(C)OCC2C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CC1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | be4b86020a065d99e289e528d425e25dd0737bea0f2fd81bb05a4d03f92a7d75 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(Nc1cccc2c1[nH]c1cnccc12)C1COCCN1CC(=O)N1CCNCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[#7:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5]-[C:10]-[C:9]-1 | 12 | [{"value": 12.0, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)C1N(CC(OC1)(C)C)CC(=O)N1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The desired compound was prepared using [5-(6-Chloro-9H-beta-carbolin-8-ylcarbamoyl)-2,2-dimethyl-morpholin-4-yl]-acetic acid and 1-methyl piperazine following Method F in 12% yield.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.C1COCC[NH]1.c1ccc2c(c1)[nH]c1cnccc12 | HO- | null | null | null | CC1(C)CN(CC(=O)O)C(C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1.CN1CCNCC1>>CN1CCN(C(=O)CN2CC(C)(C)OCC2C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CC1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-497f81d843fd40b38b68639b9989b285 | CC1(C)CN(CC(=O)O)C(C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1.CC1CNCC(C)O1>>CC1CN(C(=O)CN2CC(C)(C)OCC2C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CC(C)O1 | ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)C1COC(CN1CC(=O)O)(C)C.CC1CNCC(O1)C>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)C1N(CC(OC1)(C)C)CC(=O)N1CC(OC(C1)C)C | O[C:5](=[O:6])[CH2:7][N:8]1[CH2:9][C:10]([CH3:11])([CH3:12])[O:13][CH2:14][CH:15]1[C:16](=[O:17])[NH:18][c:19]1[cH:20][c:21]([Cl:22])[cH:23][c:24]2[c:25]1[nH:26][c:27]1[cH:28][n:29][cH:30][cH:31][c:32]21.[CH3:1][CH:2]1[CH2:3][NH:4][CH2:33][CH:34]([CH3:35])[O:36]1>>[CH3:1][CH:2]1[CH2:3][N:4]([C:5](=[O:6])[CH2:7][N:8]2[C... | CC1(C)CN(CC(=O)O)C(C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1.CC1CNCC(C)O1 | CC1CN(C(=O)CN2CC(C)(C)OCC2C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CC(C)O1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | 2ef483949e7ba3e5f888cf14cdce25fa611f75be09fdf1854a473be519821b59 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(Nc1cccc2c1[nH]c1cnccc12)C1COCCN1CC(=O)N1CCOCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4].[#8:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[#7:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:8]1-[C:9]-[C:10]-[#8:5]-[C:6]-[C:7]-1 | null | [] | null | null | null | null | The desired compound was prepared using [5-(6-Chloro-9H-beta-carbolin-8-ylcarbamoyl)-2,2-dimethyl-morpholin-4-yl]-acetic acid and 2,6-dimethyl morpholine following Method F. Chromatographic purification gave the desired product in 70-80% yield.
Conditions: See reaction.notes.procedure_details.
Workup: The desired compo... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1COCCN1 | C1COCC[NH]1 | C1COCC[NH]1.C1COCC[NH]1.c1ccc2c(c1)[nH]c1cnccc12 | HO- | null | null | null | CC1(C)CN(CC(=O)O)C(C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1.CC1CNCC(C)O1>>CC1CN(C(=O)CN2CC(C)(C)OCC2C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CC(C)O1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-8b72ff95936842d0a95d831f3c3c8d3b | CC1(C)CN(CC(=O)O)C(C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1.N[C@H]1CC[C@H](O)CC1>>CC1(C)CN(CC(=O)N[C@@H]2CC[C@@H](O)CC2)C(C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1 | C(CCl)Cl.ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)C1COC(CN1CC(=O)O)(C)C.Cl.N[C@@H]1CC[C@H](CC1)O.C(C)(C)N(CC)C(C)C>>ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)C1N(CC(OC1)(C)C)CC(N[C@@H]1CC[C@H](CC1)O)=O | O[C:7]([CH2:6][N:5]1[CH2:4][C:2]([CH3:1])([CH3:3])[O:36][CH2:35][CH:17]1[C:18](=[O:19])[NH:20][c:21]1[cH:22][c:23]([Cl:24])[cH:25][c:26]2[c:27]1[nH:28][c:29]1[cH:30][n:31][cH:32][cH:33][c:34]21)=[O:8].[NH2:9][C@H:10]1[CH2:11][CH2:12][C@H:13]([OH:14])[CH2:15][CH2:16]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][N:5]([CH2:6][C:7](=[O... | CC1(C)CN(CC(=O)O)C(C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1.N[C@H]1CC[C@H](O)CC1 | CC1(C)CN(CC(=O)N[C@@H]2CC[C@@H](O)CC2)C(C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1 | null | null | O.N1=CC=CC=C1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CN1CCOCC1C(=O)Nc1cccc2c1[nH]c1cnccc12)NC1CCCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4].[C:5]-[C:6](-[NH2;D1;+0:7])-[C:8]>>[#7:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6](-[C:5])-[C:8] | 60 | [{"value": 59.0, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)C1N(CC(OC1)(C)C)CC(N[C@@H]1CC[C@H](CC1)O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.0, "product": "ClC=1C=C2C=3C=CN=CC3NC2=C(C1)NC(=O)C1N(CC(OC1)(C)C)CC(N[C@@H]1CC[C@H](CC1)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | null | null | null | null | [5-(6-Chloro-9H-beta-carbolin-8-ylcarbamoyl)-2,2-dimethyl-morpholin-4-yl]-acetic acid (200 mg, 0.48 mmol), trans-4-aminocyclohexanol hydrochloride (145 mg, 0.96 mmol) and diisopropylethylamine (124 mg, 167 uL, 0.96 mmol) were dissolved in pyridine (4 mL) and stirred at room temperature10 min. EDC (184 mg) was added and... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1COCC[NH]1.C1CCCCC1.c1ccc2c(c1)[nH]c1cnccc12 | HO- | O.N1=CC=CC=C1 | null | null | CC1(C)CN(CC(=O)O)C(C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1.N[C@H]1CC[C@H](O)CC1>O.N1=CC=CC=C1>CC1(C)CN(CC(=O)N[C@@H]2CC[C@@H](O)CC2)C(C(=O)Nc2cc(Cl)cc3c2[nH]c2cnccc23)CO1 |
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