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-41677c4f3045402cbb69067e5b147a3b | CCOC(=O)CCN(c1nc(SC)ncc1C(=O)OCC)C1CCCCC1>>CCOC(=O)C1CN(C2CCCCC2)c2nc(SC)ncc2C1=O | Cl.[Na].C(C)OC(=O)C=1C(=NC(=NC1)SC)N(CCC(=O)OCC)C1CCCCC1.CC(C)([O-])C.[Na+]>>C(C)OC(=O)C1C(C2=C(N=C(N=C2)SC)N(C1)C1CCCCC1)=O | CCO[C:23]([c:22]1[c:15]([N:8]([CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[n:16][c:17]([S:18][CH3:19])[n:20][cH:21]1)=[O:24]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][N:8]([CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[c:15]2[n:16][c:17]([S:18][CH3:19])[n:20]... | CCOC(=O)CCN(c1nc(SC)ncc1C(=O)OCC)C1CCCCC1 | CCOC(=O)C1CN(C2CCCCC2)c2nc(SC)ncc2C1=O | null | null | C(C)(C)(C)O.C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | 30bc859f342e7454d65786ffc9dd9e1f370c7689a335282691882093ec0ad590 | 6f130a746a78d10ca37f94948711de2b0c76f45052ca887b0e681c66276a7764 | O=C1CCN(C2CCCCC2)c2ncncc21 | C-C-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-[#7:9]-[C:10]-[CH2;D2;+0:11]-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15]>>[C:15]-[#8:14]-[C:12](=[O;D1;H0:13])-[CH;D3;+0:11]1-[C:10]-[#7:9]-[c:8]2:[#7;a:7]:[c:6]:[#7;a:5]:[c:4]:[c:3]:2-[C;H0;D3;+0:1]-1=[O;D1;H0:2] | 63 | [{"value": 42.0, "product": "C(C)OC(=O)C1C(C2=C(N=C(N=C2)SC)N(C1)C1CCCCC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.0, "product": "C(C)OC(=O)C1C(C2=C(N=C(N=C2)SC)N(C1)C1CCCCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 10 | MINUTE | Sodium (25 wt % dispersion in paraffin wax, 0.10 g, 3.8 mmol) was added to t-butanol (1.8 mL) at rt. After 10 minutes, a solution of 4-[cyclohexyl-(2-ethoxycarbonyl-ethyl)-amino]-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester (1.0 g, 2.5 mmol) in 10 mL of toluene was added to the sodium t-butoxide solution a... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Ketone | null | c1ncc2c(n1)[NH]CCC2 | C1CCCCC1.c1ncc2c(n1)[NH]CCC2 | HO- | C(C)(C)(C)O.C1(=CC=CC=C1)C | 90 | 0.166667 | CCOC(=O)CCN(c1nc(SC)ncc1C(=O)OCC)C1CCCCC1>C(C)(C)(C)O.C1(=CC=CC=C1)C>CCOC(=O)C1CN(C2CCCCC2)c2nc(SC)ncc2C1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-23ec465f1d48481894c1f7294e49f135 | CCOC(=O)C1CN(C2CCCCC2)c2nc(SC)ncc2C1=O>>CCOC(=O)c1cn(C2CCCCC2)c2nc(SC)ncc2c1=O | BrBr.C(C)OC(=O)C1C(C2=C(N=C(N=C2)SC)N(C1)C1CCCCC1)=O.C(C)(C)N(CC)C(C)C>>C(C)OC(=O)C=1C(C2=C(N=C(N=C2)SC)N(C1)C1CCCCC1)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][N:8]([CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[c:15]2[n:16][c:17]([S:18][CH3:19])[n:20][cH:21][c:22]2[C:23]1=[O:24]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8]([CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[c:15]2[n:16][c:17]([S:18][CH3:19])[n:20][cH:21][... | CCOC(=O)C1CN(C2CCCCC2)c2nc(SC)ncc2C1=O | CCOC(=O)c1cn(C2CCCCC2)c2nc(SC)ncc2c1=O | null | null | ClCCl | Oxidation | OtherReaction | e6fdfa5ad0e8b814bf3d3d5cf077356d203a162eff2c4a4b9336450468009711 | 90d664ba841914112433e4101d37ffefd1e45e7dce983b85577c7f1d5a635093 | O=c1ccn(C2CCCCC2)c2ncncc12 | [C:1]-[C:2](-[N;H0;D3;+0:3]1-[CH2;D2;+0:4]-[CH;D3;+0:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9])-[C;H0;D3;+0:10](=[O;D1;H0:11])-[c:12]2:[c:13]:[#7;a:14]:[c:15]:[#7;a:16]:[c:17]:2-1)-[C:18]>>[C:1]-[C:2](-[n;H0;D3;+0:3]1:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9]):[c;H0;D3;+0:10](=[O;D1;H0:11]):[c:12]2:[c:13... | 102 | [{"value": 87.0, "product": "C(C)OC(=O)C=1C(C2=C(N=C(N=C2)SC)N(C1)C1CCCCC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 102.0, "product": "C(C)OC(=O)C=1C(C2=C(N=C(N=C2)SC)N(C1)C1CCCCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | Bromine (0.15 g, 0.94 mmol) was added to a solution of 8-cyclohexyl-2-methylsulfanyl-5-oxo-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (0.28 g, 0.79 mmol) in dichloromethane (10 mL). After 5 min, the solution was concentrated and the crude residue was redissolved in dichloromethane (10 mL) ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Tertiary amine | Ester | c1ncc2c(n1)[NH]CCC2 | c1cnc2ncncc2c1 | C1CCCCC1.c1cnc2ncncc2c1 | null | ClCCl | null | 0.083333 | CCOC(=O)C1CN(C2CCCCC2)c2nc(SC)ncc2C1=O>ClCCl>CCOC(=O)c1cn(C2CCCCC2)c2nc(SC)ncc2c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-1ac2aa84f60741819c22e5410f4c6a75 | CCOC(=O)c1cn(C2CCCCC2)c2nc(SC)ncc2c1=O.O=C(OO)c1cccc(Cl)c1>>CCOC(=O)c1cn(C2CCCCC2)c2nc(S(C)(=O)=O)ncc2c1=O | C1=CC(=CC(=C1)Cl)C(=O)OO.C(C)OC(=O)C=1C(C2=C(N=C(N=C2)SC)N(C1)C1CCCCC1)=O.[O-]S(=O)[O-].[Na+].[Na+]>>C(C)OC(=O)C=1C(C2=C(N=C(N=C2)S(=O)(=O)C)N(C1)C1CCCCC1)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8]([CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[c:15]2[n:16][c:17]([S:18][CH3:19])[n:22][cH:23][c:24]2[c:25]1=[O:26].OOC(c1cccc(Cl)c1)=[O:21]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8]([CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[c:15]2[n:16][c:17]([S:18]... | CCOC(=O)c1cn(C2CCCCC2)c2nc(SC)ncc2c1=O.O=C(OO)c1cccc(Cl)c1 | CCOC(=O)c1cn(C2CCCCC2)c2nc(S(C)(=O)=O)ncc2c1=O | null | null | ClCCl | Oxidation | OtherReaction | 84855dd3f46d7f633669ce7b0a2d1343353729d5975dd53fd20abc6eb43ece69 | dc6f43112eef310adb122ebf81e1733b34eff292ed27058fb45445842d61d3da | O=c1ccn(C2CCCCC2)c2ncncc12 | Cl-c1:c:c:c:c(-C(=[O;H0;D1;+0:1])-O-O):c:1.[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[S;H0;D2;+0:6]-[C;D1;H3:7]):[#7;a:8]:[c:9]>>[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[S;H0;D4;+0:6](-[C;D1;H3:7])(=[O;D1;H0:10])=[O;H0;D1;+0:1]):[#7;a:8]:[c:9] | null | [] | null | null | 2 | HOUR | m-CPBA (0.33 g, 1.5 mmol of a 70% w/w mixture) was added to a solution of 8-cyclohexyl-2-methylsulfanyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (0.206 g, 0.59 mmol) in dichloromethane (15 mL). After 2 hours, a 10% solution of Na2SO3 (1 mL) was added and the mixture was partitioned betwee... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide.Monosulfide | Sulfone | c1ccccc1 | null | C1CCCCC1.c1cnc2ncncc2c1 | HCl | ClCCl | null | 2 | CCOC(=O)c1cn(C2CCCCC2)c2nc(SC)ncc2c1=O.O=C(OO)c1cccc(Cl)c1>ClCCl>CCOC(=O)c1cn(C2CCCCC2)c2nc(S(C)(=O)=O)ncc2c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-9fb48450b6fe4c8b84ee8a7abcc9cfee | CCOC(=O)c1cn(C2CCCCC2)c2nc(S(C)(=O)=O)ncc2c1=O.NCCCn1ccnc1>>CCOC(=O)c1cn(C2CCCCC2)c2nc(NCCCn3ccnc3)ncc2c1=O | N1(C=NC=C1)CCCN.C(C)OC(=O)C=1C(C2=C(N=C(N=C2)S(=O)(=O)C)N(C1)C1CCCCC1)=O>>C(C)OC(=O)C=1C(C2=C(N=C(N=C2)NCCCN2C=NC=C2)N(C1)C1CCCCC1)=O | CS(=O)(=O)[c:17]1[n:16][c:15]2[n:8]([CH:9]3[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]3)[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:30](=[O:31])[c:29]2[cH:28][n:27]1.[NH2:18][CH2:19][CH2:20][CH2:21][n:22]1[cH:23][cH:24][n:25][cH:26]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8]([CH:9]2[CH2:10][CH2:11][CH2:12][CH... | CCOC(=O)c1cn(C2CCCCC2)c2nc(S(C)(=O)=O)ncc2c1=O.NCCCn1ccnc1 | CCOC(=O)c1cn(C2CCCCC2)c2nc(NCCCn3ccnc3)ncc2c1=O | null | null | CO.C(C)(=O)O | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1ccn(C2CCCCC2)c2nc(NCCCn3ccnc3)ncc12 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]:[#7;a:4]):[#7;a:5]:[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[#7;a:5]:[c:6] | 170.1 | [{"value": 170.1, "product": "C(C)OC(=O)C=1C(C2=C(N=C(N=C2)NCCCN2C=NC=C2)N(C1)C1CCCCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3-imidazol-1-yl-propylamine (6 μL, 0.036 mmol) and 8-cyclohexyl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (30 mg, 0.08 mmol) in 0.5 mL of acetic acid was heated to 110° C. for 0.5 hour. After cooling to room temperature, the mixture was dissolved in 2 mL of ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | C1CCCCC1.c1cnc2ncncc2c1.c1c[nH]cn1 | HO- | CO.C(C)(=O)O | null | null | CCOC(=O)c1cn(C2CCCCC2)c2nc(S(C)(=O)=O)ncc2c1=O.NCCCn1ccnc1>CO.C(C)(=O)O>CCOC(=O)c1cn(C2CCCCC2)c2nc(NCCCn3ccnc3)ncc2c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-7501ff3274a64db19fe67e0d2b6967e4 | CCOC(=O)c1cn(C2CCCCC2)c2nc(NCCCn3ccnc3)ncc2c1=O.N>>NC(=O)c1cn(C2CCCCC2)c2nc(NCCCn3ccnc3)ncc2c1=O | C(C)OC(=O)C=1C(C2=C(N=C(N=C2)NCCCN2C=NC=C2)N(C1)C1CCCCC1)=O.N>>C1(CCCCC1)N1C=C(C(C2=C1N=C(N=C2)NCCCN2C=NC=C2)=O)C(=O)N | CCO[C:2](=[O:3])[c:4]1[cH:5][n:6]([CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[c:13]2[n:14][c:15]([NH:16][CH2:17][CH2:18][CH2:19][n:20]3[cH:21][cH:22][n:23][cH:24]3)[n:25][cH:26][c:27]2[c:28]1=[O:29].[NH3:1]>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][n:6]([CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[c:13]2[n:14][c:15]([NH... | CCOC(=O)c1cn(C2CCCCC2)c2nc(NCCCn3ccnc3)ncc2c1=O.N | NC(=O)c1cn(C2CCCCC2)c2nc(NCCCn3ccnc3)ncc2c1=O | null | null | CO | Acylation | OtherReaction | d5b10d4f469e7a196a3b04a6a9e159a7d90514b6df5b50c1197d4b1b774c04e1 | adc0ef6f6c1340dd2dbab737c85bf17fc842769181c5db1a2b4f82b391b28f9f | O=c1ccn(C2CCCCC2)c2nc(NCCCn3ccnc3)ncc12 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6](-[C:7]):[c:8]:[#7;a:9].[NH3;D0;+0:10]>>[#7;a:9]:[c:8]:[#7;a:6](-[C:7]):[c:5]:[c:3](-[C;H0;D3;+0:1](-[NH2;D1;+0:10])=[O;D1;H0:2]):[c:4] | 95 | [{"value": 95.0, "product": "C1(CCCCC1)N1C=C(C(C2=C1N=C(N=C2)NCCCN2C=NC=C2)=O)C(=O)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 8-Cyclohexyl-2-(3-imidazol-1-yl-propylamino)-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (4.5 mg, 0.011 mmol) was added to 1.0 mL of 7 N ammonia in methanol. The mixture was stirred in a sealed tube at room temperature overnight. The solvent was evaporated to leave a white solid of 8-cyclohe... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary amide | null | null | C1CCCCC1.c1cnc2ncncc2c1.c1c[nH]cn1 | HO- | CO | null | 8 | CCOC(=O)c1cn(C2CCCCC2)c2nc(NCCCn3ccnc3)ncc2c1=O.N>CO>NC(=O)c1cn(C2CCCCC2)c2nc(NCCCn3ccnc3)ncc2c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-eb360499e0074ed69a9c2ddd2a649271 | CCOC(=O)c1cn(C2CCCCC2)c2nc(S(C)(=O)=O)ncc2c1=O.CN(C)CCCN>>CCOC(=O)c1cn(C2CCCCC2)c2nc(NCCCN(C)C)ncc2c1=O | CN(CCCN)C.C(C)OC(=O)C=1C(C2=C(N=C(N=C2)S(=O)(=O)C)N(C1)C1CCCCC1)=O>>C(C)OC(=O)C=1C(C2=C(N=C(N=C2)NCCCN(C)C)N(C1)C1CCCCC1)=O | CS(=O)(=O)[c:17]1[n:16][c:15]2[n:8]([CH:9]3[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]3)[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:28](=[O:29])[c:27]2[cH:26][n:25]1.[NH2:18][CH2:19][CH2:20][CH2:21][N:22]([CH3:23])[CH3:24]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8]([CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:1... | CCOC(=O)c1cn(C2CCCCC2)c2nc(S(C)(=O)=O)ncc2c1=O.CN(C)CCCN | CCOC(=O)c1cn(C2CCCCC2)c2nc(NCCCN(C)C)ncc2c1=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1ccn(C2CCCCC2)c2ncncc12 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]:[#7;a:4]):[#7;a:5]:[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[#7;a:5]:[c:6] | 85 | [{"value": 85.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure outlined in Example 28 Step F, the title compound was prepared from N′,N′-dimethyl-propane-1,3-diamine and 8-cyclohexyl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (Example 35 Step E, 20 mg, 0.05 mmol). 8-Cyclohexyl-2-(3-dimethylamino-propylamino)-5-oxo-... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | C1CCCCC1.c1cnc2ncncc2c1 | HO- | null | null | null | CCOC(=O)c1cn(C2CCCCC2)c2nc(S(C)(=O)=O)ncc2c1=O.CN(C)CCCN>>CCOC(=O)c1cn(C2CCCCC2)c2nc(NCCCN(C)C)ncc2c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-c4849fba64a44787b6809841dc512196 | CCOC(=O)c1cn(C2CCCCC2)c2nc(S(C)(=O)=O)ncc2c1=O.NCCCN1CCOCC1>>CCOC(=O)c1cn(C2CCCCC2)c2nc(NCCCN3CCOCC3)ncc2c1=O | N1(CCOCC1)CCCN.C(C)OC(=O)C=1C(C2=C(N=C(N=C2)S(=O)(=O)C)N(C1)C1CCCCC1)=O>>C(C)OC(=O)C=1C(C2=C(N=C(N=C2)NCCCN2CCOCC2)N(C1)C1CCCCC1)=O | CS(=O)(=O)[c:17]1[n:16][c:15]2[n:8]([CH:9]3[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]3)[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:31](=[O:32])[c:30]2[cH:29][n:28]1.[NH2:18][CH2:19][CH2:20][CH2:21][N:22]1[CH2:23][CH2:24][O:25][CH2:26][CH2:27]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8]([CH:9]2[CH2:10][CH2:11]... | CCOC(=O)c1cn(C2CCCCC2)c2nc(S(C)(=O)=O)ncc2c1=O.NCCCN1CCOCC1 | CCOC(=O)c1cn(C2CCCCC2)c2nc(NCCCN3CCOCC3)ncc2c1=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1ccn(C2CCCCC2)c2nc(NCCCN3CCOCC3)ncc12 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]:[#7;a:4]):[#7;a:5]:[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[#7;a:5]:[c:6] | 85 | [{"value": 85.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure outlined in Example 28 Step F, the title compound was prepared from 3-morpholin-4-yl-propylamine and 8-cyclohexyl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (from Example 35 Step E, 20 mg, 0.045 mmol). 8-Cyclohexyl-2-(3-morpholin-4-yl-propylamino)-5-oxo... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | C1CCCCC1.c1cnc2ncncc2c1.C1COCC[NH]1 | HO- | null | null | null | CCOC(=O)c1cn(C2CCCCC2)c2nc(S(C)(=O)=O)ncc2c1=O.NCCCN1CCOCC1>>CCOC(=O)c1cn(C2CCCCC2)c2nc(NCCCN3CCOCC3)ncc2c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-a50a8a6cd38747b999ed237db3251bb2 | CCOC(=O)c1cn(C2CCCCC2)c2nc(S(C)(=O)=O)ncc2c1=O.COCCCN>>CCOC(=O)c1cn(C2CCCCC2)c2nc(NCCCOC)ncc2c1=O | COCCCN.C(C)OC(=O)C=1C(C2=C(N=C(N=C2)S(=O)(=O)C)N(C1)C1CCCCC1)=O>>C(C)OC(=O)C=1C(C2=C(N=C(N=C2)NCCCOC)N(C1)C1CCCCC1)=O | CS(=O)(=O)[c:17]1[n:16][c:15]2[n:8]([CH:9]3[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]3)[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:27](=[O:28])[c:26]2[cH:25][n:24]1.[NH2:18][CH2:19][CH2:20][CH2:21][O:22][CH3:23]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8]([CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[c:15]... | CCOC(=O)c1cn(C2CCCCC2)c2nc(S(C)(=O)=O)ncc2c1=O.COCCCN | CCOC(=O)c1cn(C2CCCCC2)c2nc(NCCCOC)ncc2c1=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1ccn(C2CCCCC2)c2ncncc12 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]:[#7;a:4]):[#7;a:5]:[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[#7;a:5]:[c:6] | 80 | [{"value": 80.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure outlined in Example 28 Step F, the title compound was prepared from 3-methoxy-propylamine and 8-cyclohexyl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (from Example 35 (Step E) above, 30 mg, 0.08 mmol). 8-Cyclohexyl-2-(3-methoxy-propylamino)-5-oxo-5,8-di... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | C1CCCCC1.c1cnc2ncncc2c1 | HO- | null | null | null | CCOC(=O)c1cn(C2CCCCC2)c2nc(S(C)(=O)=O)ncc2c1=O.COCCCN>>CCOC(=O)c1cn(C2CCCCC2)c2nc(NCCCOC)ncc2c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-37d1f52a056b469fadc08257880cf203 | CCOC(=O)c1cn(C2CCCCC2)c2nc(S(C)(=O)=O)ncc2c1=O.CN1CCN(CCCN)CC1>>CCOC(=O)c1cn(C2CCCCC2)c2nc(NCCCN3CCN(C)CC3)ncc2c1=O | CN1CCN(CC1)CCCN.C(C)OC(=O)C=1C(C2=C(N=C(N=C2)S(=O)(=O)C)N(C1)C1CCCCC1)=O>>C(C)OC(=O)C=1C(C2=C(N=C(N=C2)NCCCN2CCN(CC2)C)N(C1)C1CCCCC1)=O | CS(=O)(=O)[c:17]1[n:16][c:15]2[n:8]([CH:9]3[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]3)[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:32](=[O:33])[c:31]2[cH:30][n:29]1.[NH2:18][CH2:19][CH2:20][CH2:21][N:22]1[CH2:23][CH2:24][N:25]([CH3:26])[CH2:27][CH2:28]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8]([CH:9]2[CH2:1... | CCOC(=O)c1cn(C2CCCCC2)c2nc(S(C)(=O)=O)ncc2c1=O.CN1CCN(CCCN)CC1 | CCOC(=O)c1cn(C2CCCCC2)c2nc(NCCCN3CCN(C)CC3)ncc2c1=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1ccn(C2CCCCC2)c2nc(NCCCN3CCNCC3)ncc12 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]:[#7;a:4]):[#7;a:5]:[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[#7;a:5]:[c:6] | 80 | [{"value": 80.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure outlined in Example 28 Step F, the title compound was prepared from 3-(4-methyl-piperazin-1-yl)-propylamine and 8-cyclohexyl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (20 mg, 0.04 mmol). 8-Cyclohexyl-2-[3-(4-methyl-piperazin-1-yl)-propylamino]-5-oxo-5,... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | C1CCCCC1.c1cnc2ncncc2c1.C1C[NH]CC[NH]1 | HO- | null | null | null | CCOC(=O)c1cn(C2CCCCC2)c2nc(S(C)(=O)=O)ncc2c1=O.CN1CCN(CCCN)CC1>>CCOC(=O)c1cn(C2CCCCC2)c2nc(NCCCN3CCN(C)CC3)ncc2c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-8de9f3b5c61f436c8e8ff7bbdfc0f2a1 | CCOC(=O)c1cn(C2CCCCC2)c2nc(S(C)(=O)=O)ncc2c1=O.NCCCN1CCCC1>>CCOC(=O)c1cn(C2CCCCC2)c2nc(NCCCN3CCCC3)ncc2c1=O | N1(CCCC1)CCCN.C(C)OC(=O)C=1C(C2=C(N=C(N=C2)S(=O)(=O)C)N(C1)C1CCCCC1)=O>>C(C)OC(=O)C=1C(C2=C(N=C(N=C2)NCCCN2CCCC2)N(C1)C1CCCCC1)=O | CS(=O)(=O)[c:17]1[n:16][c:15]2[n:8]([CH:9]3[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]3)[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:30](=[O:31])[c:29]2[cH:28][n:27]1.[NH2:18][CH2:19][CH2:20][CH2:21][N:22]1[CH2:23][CH2:24][CH2:25][CH2:26]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8]([CH:9]2[CH2:10][CH2:11][CH2:1... | CCOC(=O)c1cn(C2CCCCC2)c2nc(S(C)(=O)=O)ncc2c1=O.NCCCN1CCCC1 | CCOC(=O)c1cn(C2CCCCC2)c2nc(NCCCN3CCCC3)ncc2c1=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1ccn(C2CCCCC2)c2nc(NCCCN3CCCC3)ncc12 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]:[#7;a:4]):[#7;a:5]:[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[#7;a:5]:[c:6] | 85 | [{"value": 85.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure outlined in Example 28 Step F, the title compound was prepared from 3-pyrrolidin-1-yl-propylamine and 8-cyclohexyl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (20 mg, 0.05 mmol). 8-Cyclohexyl-5-oxo-2-(3-pyrrolidin-1-yl-propylamino)-5,8-dihydro-pyrido[2,3... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | C1CCCCC1.c1cnc2ncncc2c1.C1CC[NH]C1 | HO- | null | null | null | CCOC(=O)c1cn(C2CCCCC2)c2nc(S(C)(=O)=O)ncc2c1=O.NCCCN1CCCC1>>CCOC(=O)c1cn(C2CCCCC2)c2nc(NCCCN3CCCC3)ncc2c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-598cffb0827443bfbc52db9b81b62db8 | CCOC(=O)c1cn(C2CCCCC2)c2nc(S(C)(=O)=O)ncc2c1=O.COCCN>>CCOC(=O)c1cn(C2CCCCC2)c2nc(NCCOC)ncc2c1=O | COCCN.C(C)OC(=O)C=1C(C2=C(N=C(N=C2)S(=O)(=O)C)N(C1)C1CCCCC1)=O>>C(C)OC(=O)C=1C(C2=C(N=C(N=C2)NCCOC)N(C1)C1CCCCC1)=O | CS(=O)(=O)[c:17]1[n:16][c:15]2[n:8]([CH:9]3[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]3)[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:26](=[O:27])[c:25]2[cH:24][n:23]1.[NH2:18][CH2:19][CH2:20][O:21][CH3:22]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8]([CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[c:15]2[n:16][... | CCOC(=O)c1cn(C2CCCCC2)c2nc(S(C)(=O)=O)ncc2c1=O.COCCN | CCOC(=O)c1cn(C2CCCCC2)c2nc(NCCOC)ncc2c1=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1ccn(C2CCCCC2)c2ncncc12 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]:[#7;a:4]):[#7;a:5]:[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[#7;a:5]:[c:6] | 80 | [{"value": 80.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure outlined in Example 28 Step F, the title compound was prepared from 2-methoxy-ethylamine and 8-cyclohexyl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (27 mg, 0.07 mmol). 8-Cyclohexyl-5-oxo-2-(2-methoxy-ethylamino)-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-ca... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | C1CCCCC1.c1cnc2ncncc2c1 | HO- | null | null | null | CCOC(=O)c1cn(C2CCCCC2)c2nc(S(C)(=O)=O)ncc2c1=O.COCCN>>CCOC(=O)c1cn(C2CCCCC2)c2nc(NCCOC)ncc2c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-0325c45435ff4ca4a98f12cfd7a32f52 | CCOC(=O)c1cn(C2CCCCC2)c2nc(S(C)(=O)=O)ncc2c1=O.NCCN1CCCC1>>CCOC(=O)c1cn(C2CCCCC2)c2nc(NCCN3CCCC3)ncc2c1=O | N1(CCCC1)CCN.C(C)OC(=O)C=1C(C2=C(N=C(N=C2)S(=O)(=O)C)N(C1)C1CCCCC1)=O>>C(C)OC(=O)C=1C(C2=C(N=C(N=C2)NCCN2CCCC2)N(C1)C1CCCCC1)=O | CS(=O)(=O)[c:17]1[n:16][c:15]2[n:8]([CH:9]3[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]3)[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:29](=[O:30])[c:28]2[cH:27][n:26]1.[NH2:18][CH2:19][CH2:20][N:21]1[CH2:22][CH2:23][CH2:24][CH2:25]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8]([CH:9]2[CH2:10][CH2:11][CH2:12][CH2:1... | CCOC(=O)c1cn(C2CCCCC2)c2nc(S(C)(=O)=O)ncc2c1=O.NCCN1CCCC1 | CCOC(=O)c1cn(C2CCCCC2)c2nc(NCCN3CCCC3)ncc2c1=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1ccn(C2CCCCC2)c2nc(NCCN3CCCC3)ncc12 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]:[#7;a:4]):[#7;a:5]:[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[#7;a:5]:[c:6] | 80 | [{"value": 80.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure outlined in Example 28 Step F, the title compound was prepared from 2-pyrrolidin-1-yl-ethylamine and 8-cyclohexyl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (25 mg, 0.07 mmol). 8-Cyclohexyl-5-oxo-2-(2-pyrrolidin-1-yl-ethylamino)-5,8-dihydro-pyrido[2,3-d... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | C1CCCCC1.c1cnc2ncncc2c1.C1CC[NH]C1 | HO- | null | null | null | CCOC(=O)c1cn(C2CCCCC2)c2nc(S(C)(=O)=O)ncc2c1=O.NCCN1CCCC1>>CCOC(=O)c1cn(C2CCCCC2)c2nc(NCCN3CCCC3)ncc2c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-0912ed3cd556424e952f30aad94113c4 | CCOC(=O)c1cn(C2CCCCC2)c2nc(S(C)(=O)=O)ncc2c1=O.COc1ccc(CCN)cc1>>CCOC(=O)c1cn(C2CCCCC2)c2nc(NCCc3ccc(OC)cc3)ncc2c1=O | COC1=CC=C(C=C1)CCN.C(C)OC(=O)C=1C(C2=C(N=C(N=C2)S(=O)(=O)C)N(C1)C1CCCCC1)=O>>C(C)OC(=O)C=1C(C2=C(N=C(N=C2)NCCC2=CC=C(C=C2)OC)N(C1)C1CCCCC1)=O | CS(=O)(=O)[c:17]1[n:16][c:15]2[n:8]([CH:9]3[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]3)[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:32](=[O:33])[c:31]2[cH:30][n:29]1.[NH2:18][CH2:19][CH2:20][c:21]1[cH:22][cH:23][c:24]([O:25][CH3:26])[cH:27][cH:28]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8]([CH:9]2[CH2:10][CH2... | CCOC(=O)c1cn(C2CCCCC2)c2nc(S(C)(=O)=O)ncc2c1=O.COc1ccc(CCN)cc1 | CCOC(=O)c1cn(C2CCCCC2)c2nc(NCCc3ccc(OC)cc3)ncc2c1=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1ccn(C2CCCCC2)c2nc(NCCc3ccccc3)ncc12 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]:[#7;a:4]):[#7;a:5]:[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[#7;a:5]:[c:6] | 85 | [{"value": 85.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure outlined in Example 28 Step F, the title compound was prepared from 2-(4-methoxy-phenyl)-ethylamine and 8-cyclohexyl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (from Example 35 (Step E), 35 mg, 0.09 mmol). 8-Cyclohexyl-5-oxo-2-[2-(4-methoxy-phenyl)-ethy... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | C1CCCCC1.c1cnc2ncncc2c1.c1ccccc1 | HO- | null | null | null | CCOC(=O)c1cn(C2CCCCC2)c2nc(S(C)(=O)=O)ncc2c1=O.COc1ccc(CCN)cc1>>CCOC(=O)c1cn(C2CCCCC2)c2nc(NCCc3ccc(OC)cc3)ncc2c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-9ce6fc1cc68d47d58102841dd0dba082 | CCOC(=O)c1cn(C2CCCCC2)c2nc(S(C)(=O)=O)ncc2c1=O.NCCN1CCCCC1>>CCOC(=O)c1cn(C2CCCCC2)c2nc(NCCN3CCCCC3)ncc2c1=O | N1(CCCCC1)CCN.C(C)OC(=O)C=1C(C2=C(N=C(N=C2)S(=O)(=O)C)N(C1)C1CCCCC1)=O>>C(C)OC(=O)C=1C(C2=C(N=C(N=C2)NCCN2CCCCC2)N(C1)C1CCCCC1)=O | CS(=O)(=O)[c:17]1[n:16][c:15]2[n:8]([CH:9]3[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]3)[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:30](=[O:31])[c:29]2[cH:28][n:27]1.[NH2:18][CH2:19][CH2:20][N:21]1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8]([CH:9]2[CH2:10][CH2:11][CH2:1... | CCOC(=O)c1cn(C2CCCCC2)c2nc(S(C)(=O)=O)ncc2c1=O.NCCN1CCCCC1 | CCOC(=O)c1cn(C2CCCCC2)c2nc(NCCN3CCCCC3)ncc2c1=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1ccn(C2CCCCC2)c2nc(NCCN3CCCCC3)ncc12 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]:[#7;a:4]):[#7;a:5]:[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[#7;a:5]:[c:6] | 80 | [{"value": 80.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure outlined in Example 28 Step F, the title compound was prepared from 2-piperidin-1-yl-ethylamine and 8-cyclohexyl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (25 mg, 0.06 mmol). 8-Cyclohexyl-5-oxo-2-(2-piperidin-1-yl-ethylamino)-5,8-dihydro-pyrido[2,3-d]p... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | C1CCCCC1.c1cnc2ncncc2c1.C1CC[NH]CC1 | HO- | null | null | null | CCOC(=O)c1cn(C2CCCCC2)c2nc(S(C)(=O)=O)ncc2c1=O.NCCN1CCCCC1>>CCOC(=O)c1cn(C2CCCCC2)c2nc(NCCN3CCCCC3)ncc2c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-4c8adea079444a19ada5a509e02edf4d | CCOC(=O)c1cn(C2CCCCC2)c2nc(S(C)(=O)=O)ncc2c1=O.NCCN1CCOCC1>>CCOC(=O)c1cn(C2CCCCC2)c2nc(NCCN3CCOCC3)ncc2c1=O | N1(CCOCC1)CCN.C(C)OC(=O)C=1C(C2=C(N=C(N=C2)S(=O)(=O)C)N(C1)C1CCCCC1)=O>>C(C)OC(=O)C=1C(C2=C(N=C(N=C2)NCCN2CCOCC2)N(C1)C1CCCCC1)=O | CS(=O)(=O)[c:17]1[n:16][c:15]2[n:8]([CH:9]3[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]3)[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:30](=[O:31])[c:29]2[cH:28][n:27]1.[NH2:18][CH2:19][CH2:20][N:21]1[CH2:22][CH2:23][O:24][CH2:25][CH2:26]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8]([CH:9]2[CH2:10][CH2:11][CH2:12]... | CCOC(=O)c1cn(C2CCCCC2)c2nc(S(C)(=O)=O)ncc2c1=O.NCCN1CCOCC1 | CCOC(=O)c1cn(C2CCCCC2)c2nc(NCCN3CCOCC3)ncc2c1=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1ccn(C2CCCCC2)c2nc(NCCN3CCOCC3)ncc12 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]:[#7;a:4]):[#7;a:5]:[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[#7;a:5]:[c:6] | 80 | [{"value": 80.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure outlined in Example 28 Step F, the title compound was prepared from 2-morpholin-4-yl-ethylamine and 8-cyclohexyl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (30 mg, 0.08 mmol). 8-Cyclohexyl-5-oxo-2-(2-morpholin-4-yl-ethylamino)-5,8-dihydro-pyrido[2,3-d]p... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | C1CCCCC1.c1cnc2ncncc2c1.C1COCC[NH]1 | HO- | null | null | null | CCOC(=O)c1cn(C2CCCCC2)c2nc(S(C)(=O)=O)ncc2c1=O.NCCN1CCOCC1>>CCOC(=O)c1cn(C2CCCCC2)c2nc(NCCN3CCOCC3)ncc2c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-0cd2521c5a3847ab8129827e4d8d4efa | CCOC(=O)c1cn(C2CCCCC2)c2nc(S(C)(=O)=O)ncc2c1=O.COc1cc(CN)cc(OC)c1>>CCOC(=O)c1cn(C2CCCCC2)c2nc(NCc3cc(OC)cc(OC)c3)ncc2c1=O | COC=1C=C(CN)C=C(C1)OC.C(C)OC(=O)C=1C(C2=C(N=C(N=C2)S(=O)(=O)C)N(C1)C1CCCCC1)=O>>C(C)OC(=O)C=1C(C2=C(N=C(N=C2)NCC2=CC(=CC(=C2)OC)OC)N(C1)C1CCCCC1)=O | CS(=O)(=O)[c:17]1[n:16][c:15]2[n:8]([CH:9]3[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]3)[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:33](=[O:34])[c:32]2[cH:31][n:30]1.[NH2:18][CH2:19][c:20]1[cH:21][c:22]([O:23][CH3:24])[cH:25][c:26]([O:27][CH3:28])[cH:29]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8]([CH:9]2[CH2:... | CCOC(=O)c1cn(C2CCCCC2)c2nc(S(C)(=O)=O)ncc2c1=O.COc1cc(CN)cc(OC)c1 | CCOC(=O)c1cn(C2CCCCC2)c2nc(NCc3cc(OC)cc(OC)c3)ncc2c1=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1ccn(C2CCCCC2)c2nc(NCc3ccccc3)ncc12 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]:[#7;a:4]):[#7;a:5]:[c:6].[NH2;D1;+0:7]-[C:8]-[c:9]>>[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[C:8]-[c:9]):[#7;a:5]:[c:6] | 90 | [{"value": 90.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure outlined in Example 28 Step F, the title compound was prepared from 3,5-dimethoxy-benzylamine and 8-cyclohexyl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (33 mg, 0.08 mmol). 8-Cyclohexyl-5-oxo-2-(3,5-dimethoxy-benzylamino)-5,8-dihydro-pyrido[2,3-d]pyrim... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | C1CCCCC1.c1cnc2ncncc2c1.c1ccccc1 | HO- | null | null | null | CCOC(=O)c1cn(C2CCCCC2)c2nc(S(C)(=O)=O)ncc2c1=O.COc1cc(CN)cc(OC)c1>>CCOC(=O)c1cn(C2CCCCC2)c2nc(NCc3cc(OC)cc(OC)c3)ncc2c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-875efa1e71a84f36936757e075bf886b | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCCn3ccnc3)ncc2c1=O.CON>>CONC(=O)c1cn(C2CCCCC2)c2nc(NCCCn3ccnc3)ncc2c1=O | C(C)N(CC)CC.Cl.CON.C(C)OC(=O)C=1C(C2=C(N=C(N=C2)NCCCN2C=NC=C2)N(C1)C=1C=C2CCCC2=CC1)=O>>CONC(=O)C=1C(C2=C(N=C(N=C2)NCCCN2C=NC=C2)N(C1)C1CCCCC1)=O | CCO[C:4](=[O:5])[c:6]1[cH:7][n:8](-[c:9]2ccc3[c:11]([cH:10]2)[CH2:12][CH2:13][CH2:14]3)[c:15]2[n:16][c:17]([NH:18][CH2:19][CH2:20][CH2:21][n:22]3[cH:23][cH:24][n:25][cH:26]3)[n:27][cH:28][c:29]2[c:30]1=[O:31].[CH3:1][O:2][NH2:3]>>[CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[cH:7][n:8]([CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][C... | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCCn3ccnc3)ncc2c1=O.CON | CONC(=O)c1cn(C2CCCCC2)c2nc(NCCCn3ccnc3)ncc2c1=O | null | null | CO.O | Acylation | OtherReaction | d76aca16c292f8e470416a61b142a0781cc827b67f9b3af327adb14f492c7a50 | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | O=c1ccn(C2CCCCC2)c2nc(NCCCn3ccnc3)ncc12 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]2:[c:6]:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]:2:[n;H0;D3;+0:11](-[c;H0;D3;+0:12]2:[cH;D2;+0:13]:[c;H0;D3;+0:14]3:c(:c:c:2)-[CH2;D2;+0:15]-[C:16]-[C:17]-3):[c:18]:1.[C;D1;H3:19]-[#8:20]-[NH2;D1;+0:21]>>[C;D1;H3:19]-[#8:20]-[NH;D2;+0:21]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c... | 70 | [{"value": 70.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | Triethylamine (0.5 mL) was added to a mixture of O-methylhydroxylamine hydrochloride (220 mg) and 2-(3-Imidazol-1-yl-propylamino)-8-indan-5-yl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (from Example 28 Step F, 6.0 mg, 0.013 mmol) in 0.5 mL of methanol. The reaction mixture was kept in a se... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | c1ccc2c(c1)CCC2 | C1CCCCC1 | C1CCCCC1.c1cnc2ncncc2c1.c1c[nH]cn1 | HO- | CO.O | null | 48 | CCOC(=O)c1cn(-c2ccc3c(c2)CCC3)c2nc(NCCCn3ccnc3)ncc2c1=O.CON>CO.O>CONC(=O)c1cn(C2CCCCC2)c2nc(NCCCn3ccnc3)ncc2c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-865cc6e9e74747bfadcbd7e76272fd1f | CCOC(=O)c1cn(C2CCCCC2)c2nc(NCCCn3ccnc3)ncc2c1=O.CN>>CNC(=O)c1cn(C2CCCCC2)c2nc(NCCCn3ccnc3)ncc2c1=O | CN.C(C)OC(=O)C=1C(C2=C(N=C(N=C2)NCCCN2C=NC=C2)N(C1)C1CCCCC1)=O>>CNC(=O)C=1C(C2=C(N=C(N=C2)NCCCN2C=NC=C2)N(C1)C1CCCCC1)=O | CCO[C:3](=[O:4])[c:5]1[cH:6][n:7]([CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)[c:14]2[n:15][c:16]([NH:17][CH2:18][CH2:19][CH2:20][n:21]3[cH:22][cH:23][n:24][cH:25]3)[n:26][cH:27][c:28]2[c:29]1=[O:30].[CH3:1][NH2:2]>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][n:7]([CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)[c:14]2[... | CCOC(=O)c1cn(C2CCCCC2)c2nc(NCCCn3ccnc3)ncc2c1=O.CN | CNC(=O)c1cn(C2CCCCC2)c2nc(NCCCn3ccnc3)ncc2c1=O | null | null | null | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | O=c1ccn(C2CCCCC2)c2nc(NCCCn3ccnc3)ncc12 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6](-[C:7]):[c:8]:[#7;a:9].[C;D1;H3:10]-[NH2;D1;+0:11]>>[#7;a:9]:[c:8]:[#7;a:6](-[C:7]):[c:5]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:11]-[C;D1;H3:10]):[c:4] | 80 | [{"value": 80.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | A solution of methylamine (1N, 1 ml in methanol) was added to 2-(3-imidazol-1-yl-propylamino)-8-cyclohexyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (Example 28, Step F, 7.0 mg, 0.015 mmol). The mixture was kept in a sealed tube at 110° C. with stirring for 2 days. The solution, after cool... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | C1CCCCC1.c1cnc2ncncc2c1.c1c[nH]cn1 | HO- | null | null | 48 | CCOC(=O)c1cn(C2CCCCC2)c2nc(NCCCn3ccnc3)ncc2c1=O.CN>>CNC(=O)c1cn(C2CCCCC2)c2nc(NCCCn3ccnc3)ncc2c1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-5149e481278741f7a4613a29de63943b | CC(C)(C)OC(=O)N1CCC(=O)CC1.O=C(O)CCc1ccc(F)cc1>>CC(C)(C)OC(=O)N1CCC(O)(C(Cc2ccc(F)cc2)C(=O)O)CC1 | C(CCC)[Li].FC1=CC=C(C=C1)CCC(=O)O.C(C)(C)NC(C)C.C(=O)(OC(C)(C)C)N1CCC(CC1)=O>>C(C)(C)(C)OC(=O)N1CCC(CC1)(O)C(CC1=CC=C(C=C1)F)C(=O)O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11](=[O:12])[CH2:25][CH2:26]1.[CH2:13]([CH2:14][c:15]1[cH:16][cH:17][c:18]([F:19])[cH:20][cH:21]1)[C:22](=[O:23])[OH:24]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11]([OH:12])([CH:13]([CH2:14][c:15]2[cH:16][cH:17][c:1... | CC(C)(C)OC(=O)N1CCC(=O)CC1.O=C(O)CCc1ccc(F)cc1 | CC(C)(C)OC(=O)N1CCC(O)(C(Cc2ccc(F)cc2)C(=O)O)CC1 | null | null | C1CCOC1.O.C(C)OCC | C-C Coupling | OtherReaction | eeb43c76bf428a561043449a39413034f3f2377495121537b37ca48c390b8557 | 454f67ba8644982dc9f605915a0f36178771eadaffb50d3f1e0f17f2b6fdeb10 | c1ccc(CCC2CCNCC2)cc1 | [O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[CH2;D2;+0:4]-[C:5]-[c:6].[O;H0;D1;+0:7]=[C;H0;D3;+0:8]1-[C:9]-[C:10]-[#7:11]-[C:12]-[C:13]-1>>[O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[CH;D3;+0:4](-[C:5]-[c:6])-[C;H0;D4;+0:8]1(-[OH;D1;+0:7])-[C:9]-[C:10]-[#7:11]-[C:12]-[C:13]-1 | null | [] | 0 | CELSIUS | 30 | MINUTE | n-Butyllithium (1.6 M in hexane, 8.8 mL, 14.0 mmol) was added dropwise under stirring over 5 min to a cooled solution of N,N-diisopropylamine (2.0 mL, 14.0 mmol) in THF (10 mL) at −40° C. The solution was warmed to 0° C. and a solution of 3-(4-fluoro-phenyl)propionic acid (1.18 g, 7.0 mmol) in THF (8 mL) was added. The... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol | C1CC[NH]CC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1 | null | C1CCOC1.O.C(C)OCC | 0 | 0.5 | CC(C)(C)OC(=O)N1CCC(=O)CC1.O=C(O)CCc1ccc(F)cc1>C1CCOC1.O.C(C)OCC>CC(C)(C)OC(=O)N1CCC(O)(C(Cc2ccc(F)cc2)C(=O)O)CC1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-5a2c7e9848a74cea8703403998e12834 | C1COCCN1.CC(C)COc1ccc(CN2C(=O)OC3(CCN(C(=O)OC(C)(C)C)CC3)C2Cc2ccc(F)cc2)cc1.ClCCCI>>CC(C)COc1ccc(CN2C(=O)OC3(CCN(CCCN4CCOCC4)CC3)C2Cc2ccc(F)cc2)cc1.Cl.Cl | [I-].[Na+].C(C)(C)(C)OC(=O)N1CCC2(C(N(C(O2)=O)CC2=CC=C(C=C2)OCC(C)C)CC2=CC=C(C=C2)F)CC1.N1CCOCC1.ClCCCI.C([O-])([O-])=O.[K+].[K+]>>Cl.Cl.FC1=CC=C(CC2N(C(OC23CCN(CC3)CCCN3CCOCC3)=O)CC3=CC=C(C=C3)OCC(C)C)C=C1 | [NH:22]1[CH2:23][CH2:24][O:25][CH2:26][CH2:27]1.CC(C)(C)OC(=O)[N:18]1[CH2:17][CH2:16][C:15]2([O:14][C:12](=[O:13])[N:11]([CH2:10][c:9]3[cH:8][cH:7][c:6]([O:5][CH2:4][CH:2]([CH3:1])[CH3:3])[cH:40][cH:39]3)[CH:30]2[CH2:31][c:32]2[cH:33][cH:34][c:35]([F:36])[cH:37][cH:38]2)[CH2:29][CH2:28]1.I[CH2:21][CH2:20][CH2:19][Cl:41... | C1COCCN1.CC(C)COc1ccc(CN2C(=O)OC3(CCN(C(=O)OC(C)(C)C)CC3)C2Cc2ccc(F)cc2)cc1.ClCCCI | CC(C)COc1ccc(CN2C(=O)OC3(CCN(CCCN4CCOCC4)CC3)C2Cc2ccc(F)cc2)cc1.Cl.Cl | null | null | CN(C)C=O.C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 5ab09c109745018d60675ce08448c38a0a560a2bef727adf144319f2e2eaf407 | 5c230f77d60fa4c5624050ee0b251756f827227fb0b5e1a6b34dee6818ae30d1 | O=C1OC2(CCN(CCCN3CCOCC3)CC2)C(Cc2ccccc2)N1Cc1ccccc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5].I-[CH2;D2;+0:6]-[C:7]-[CH2;D2;+0:8]-[Cl;H0;D1;+0:9].[#8:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[C:3]-[C:2]-[N;H0;D3;+0:1](-[CH2;D2;+0:8]-[C:7]-[CH2;D2;+0:6]-[N;H0;D3;+0:13]1-[C:12]-[C:11]-[#8:10]-[C:15]-[C:14]-1)-[C:4]-[C:5].[ClH;D0;+0:9] | 59.6 | [{"value": 40.0, "product": "Cl.Cl.FC1=CC=C(CC2N(C(OC23CCN(CC3)CCCN3CCOCC3)=O)CC3=CC=C(C=C3)OCC(C)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.6, "product": "Cl.Cl.FC1=CC=C(CC2N(C(OC23CCN(CC3)CCCN3CCOCC3)=O)CC3=CC=C(C=C3)OCC(C)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 8 | HOUR | 69NLS77 (300 mg, 0.57 mmol) was N-BOC deprotected as described in the preparation of 69NLS79-II and dissolved in acetonitrile (3 mL) and DMF (1 mL). To a solution of morpholine (65 μL, 0.74 mmol) in acetonitrile (3 mL) and DMF (1 mL) was added dropwise 1-chloro-3-iodopropane (73 μL, 0.68 mmol) and potassium carbonate (... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Carbamic ester.Ether.Secondary amine.Boc | Tertiary amine.Tertiary amine | C1COCCN1.C1CC2(CC[NH]1)C[NH]CO2 | C1CC2(CC[NH]1)C[NH]CO2.C1COCC[NH]1 | c1ccccc1.C1CC2(CC[NH]1)C[NH]CO2.C1COCC[NH]1.c1ccccc1 | HI | CN(C)C=O.C(C)#N | 50 | 8 | C1COCCN1.CC(C)COc1ccc(CN2C(=O)OC3(CCN(C(=O)OC(C)(C)C)CC3)C2Cc2ccc(F)cc2)cc1.ClCCCI>CN(C)C=O.C(C)#N>CC(C)COc1ccc(CN2C(=O)OC3(CCN(CCCN4CCOCC4)CC3)C2Cc2ccc(F)cc2)cc1.Cl.Cl |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-ced818104f6646a0b4c67d321a5aa17e | Fc1ccc(CCBr)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>Fc1ccc(CC[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1.[Br-] | FC1=CC=C(C=C1)CCBr.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>[Br-].FC1=CC=C(C=C1)CC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | [F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][Br:29])[cH:27][cH:28]1.[P:8]([c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)([c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][P+:8]([c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)([c:15]2[cH:16][cH:17... | Fc1ccc(CCBr)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | Fc1ccc(CC[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1.[Br-] | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | 72a5231b07f184f0ef4a0648badd4176f521b95f1ba3340a0f90d8894af47260 | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | c1ccc(CC[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[c:4].[c:5]:[c:6](-[P;H0;D3;+0:7](-[c:8](:[c:9]):[c:10])-[c:11](:[c:12]):[c:13]):[c:14]>>[Br-;H0;D0:1].[c:5]:[c:6](-[P+;H0;D4:7](-[CH2;D2;+0:2]-[C:3]-[c:4])(-[c:8](:[c:9]):[c:10])-[c:11](:[c:12]):[c:13]):[c:14] | null | [] | 200 | CELSIUS | null | null | 4-Fluorophenylethyl bromide (700 mg, 3.44 mmol) was dissolved in toluene (4 mL), triphenylphosphine (904 mg, 3.44 mmol) added and the solution heated for 10 min in a sealed flask at 200° C. under microwave heating. After cooling to rt, the solvent was decanted and the title compound was obtained quantitatively as the r... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | C1(=CC=CC=C1)C | 200 | null | Fc1ccc(CCBr)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>C1(=CC=CC=C1)C>Fc1ccc(CC[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1.[Br-] |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-82c7cda0ea19489b8bb5ea8f54195000 | Fc1ccc(CC[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1.O=C1CCN(C(=O)OCc2ccccc2)CC1>>O=C(OCc1ccccc1)N1CCC(=CCc2ccc(F)cc2)CC1 | [Br-].FC1=CC=C(C=C1)CC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.O=C1CCN(CC1)C(=O)OCC1=CC=CC=C1.O>>C(C1=CC=CC=C1)OC(=O)N1CCC(CC1)=CCC1=CC=C(C=C1)F | c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:15][CH2:16][c:17]2[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]2)cc1.O=[C:14]1[CH2:13][CH2:12][N:11]([C:2](=[O:1])[O:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[CH2:25][CH2:24]1>>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[N:11]1[CH2:12][CH2:13][C:14](=[CH:15][CH... | Fc1ccc(CC[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1.O=C1CCN(C(=O)OCc2ccccc2)CC1 | O=C(OCc1ccccc1)N1CCC(=CCc2ccc(F)cc2)CC1 | null | null | C1CCOC1 | C-C Coupling | Wittig with Phosphonium | ecb4a782aee0dfa853b9f6526be029681ce552b9937de9629d41519dc5ce02fa | 06a42e352cf517302d592bf38a2fd11b220014e39071074dc7becb6ee0bee4b2 | O=C(OCc1ccccc1)N1CCC(=CCc2ccccc2)CC1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[c:7]-[C:8]-[CH2;D2;+0:9]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[c:7]-[C:8]-[CH;D2;+0:9]=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1 | 17.2 | [{"value": 17.0, "product": "C(C1=CC=CC=C1)OC(=O)N1CCC(CC1)=CCC1=CC=C(C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 17.2, "product": "C(C1=CC=CC=C1)OC(=O)N1CCC(CC1)=CCC1=CC=C(C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a suspension of phosphonium bromide 78NLS66 (4.69 g, 10.1 mmol) in THF (100 mL) n-butyllithium (1.6 M in hexane, 6.3 mL, 10.1 mmol) was added at 0° C., giving a deep red solution. After stirring for 1 h at rt, a solution of benzyl 4-oxo-1-piperidinecarboxylate (2.24 g, 9.6 mmol) in THF (10 mL) was added dropwise ove... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CC[NH]CC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1 | HO- | C1CCOC1 | null | 1 | Fc1ccc(CC[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1.O=C1CCN(C(=O)OCc2ccccc2)CC1>C1CCOC1>O=C(OCc1ccccc1)N1CCC(=CCc2ccc(F)cc2)CC1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-4ff04c5e94c1429fb6e2c8b432ea5d8a | NC(Cc1ccc(F)cc1)C1(O)CCN(C(=O)OCc2ccccc2)CC1>>O=C1COC2(CCN(C(=O)OCc3ccccc3)CC2)C(Cc2ccc(F)cc2)N1 | C(C1=CC=CC=C1)OC(=O)N1CCC(CC1)(O)C(CC1=CC=C(C=C1)F)N.[Na+].[I-].ClCC(=O)Cl.[I-].CC(C)([O-])C>>C(C1=CC=CC=C1)OC(=O)N1CCC2(C(NC(CO2)=O)CC2=CC=C(C=C2)F)CC1 | [OH:4][C:5]1([CH:21]([CH2:22][c:23]2[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]2)[NH2:30])[CH2:6][CH2:7][N:8]([C:9](=[O:10])[O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19][CH2:20]1>>[O:1]=[C:2]1[CH2:3][O:4][C:5]2([CH2:6][CH2:7][N:8]([C:9](=[O:10])[O:11][CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18... | NC(Cc1ccc(F)cc1)C1(O)CCN(C(=O)OCc2ccccc2)CC1 | O=C1COC2(CCN(C(=O)OCc3ccccc3)CC2)C(Cc2ccc(F)cc2)N1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | b5aa0679b9babd19a127cd6fe873310338c3a2cb6e7c9839c5c705d57825433d | 3fb4ee9aceabdfb2df4456a679f7c00603ffa8a241c596c92b98a8c6149dbb23 | O=C1COC2(CCN(C(=O)OCc3ccccc3)CC2)C(Cc2ccccc2)N1 | [C:1]-[C:2](-[OH;D1;+0:3])(-[C:4](-[C:5])-[NH2;D1;+0:6])-[C:7]>>[C:1]-[C:2]1(-[C:7])-[O;H0;D2;+0:3]-[C:8]-[C:9](=[O;D1;H0:10])-[NH;D2;+0:6]-[C:4]-1-[C:5] | 19 | [{"value": 19.0, "product": "C(C1=CC=CC=C1)OC(=O)N1CCC2(C(NC(CO2)=O)CC2=CC=C(C=C2)F)CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared from aminoalcohol 103NLS28 (303 mg, 0.81 mmol) according to literature procedures (Clark et al., J. Med. Chem. 26:855-861 (1983)), by acylation of the amino function with chloroacetylchloride, followed by halogen exchange with NaI and ring closure of the iodide derivative in presence of ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol.Primary amine | Ether.Secondary amide | null | C1CC2(CC[NH]1)CNCCO2 | C1CC2(CC[NH]1)CNCCO2.c1ccccc1.c1ccccc1 | Other | null | null | null | NC(Cc1ccc(F)cc1)C1(O)CCN(C(=O)OCc2ccccc2)CC1>>O=C1COC2(CCN(C(=O)OCc3ccccc3)CC2)C(Cc2ccc(F)cc2)N1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-221ce167bc1c4ef8b10aeb7625dfe25c | CC(C)COc1ccc(CN2C(=O)COC3(CCN(C(=O)OCc4ccccc4)CC3)C2Cc2ccc(F)cc2)cc1>>CC(C)COc1ccc(CN2C(=O)COC3(CCNCC3)C2Cc2ccc(F)cc2)cc1 | C(C1=CC=CC=C1)OC(=O)N1CCC2(C(N(C(CO2)=O)CC2=CC=C(C=C2)OCC(C)C)CC2=CC=C(C=C2)F)CC1>>FC1=CC=C(CC2N(C(COC23CCNCC3)=O)CC3=CC=C(C=C3)OCC(C)C)C=C1 | O=C(OCc1ccccc1)[N:19]1[CH2:18][CH2:17][C:16]2([O:15][CH2:14][C:12](=[O:13])[N:11]([CH2:10][c:9]3[cH:8][cH:7][c:6]([O:5][CH2:4][CH:2]([CH3:1])[CH3:3])[cH:32][cH:31]3)[CH:22]2[CH2:23][c:24]2[cH:25][cH:26][c:27]([F:28])[cH:29][cH:30]2)[CH2:21][CH2:20]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([CH2:10][N:... | CC(C)COc1ccc(CN2C(=O)COC3(CCN(C(=O)OCc4ccccc4)CC3)C2Cc2ccc(F)cc2)cc1 | CC(C)COc1ccc(CN2C(=O)COC3(CCNCC3)C2Cc2ccc(F)cc2)cc1 | null | [Pd] | C(C)O | Reduction | Hydrogenolysis of tertiary amines | af937304b21264b8811b469296e5eb22ab5b770b0214dd2feafbbc70aad61f9b | 20c36f41eeb07c3ba4437b51ba72e8ff3c22d0b27e7197b0e9af3127f331149f | O=C1COC2(CCNCC2)C(Cc2ccccc2)N1Cc1ccccc1 | O=C(-O-C-c1:c:c:c:c:c:1)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | null | [] | null | null | null | null | The spirocycle 103NLS33 (62 mg, 0.107 mmol) in ethanol (5 mL) was N-CBz-deprotected by hydrogenation in presence of Pd/C (10%, 40 mg) under H2-balloon pressure. The catalyst was filtered off and the filtrate evaporated under reduced pressure to give crude 5-(4-fluorobenzyl)-4-(4-isobutoxybenzyl)-1-oxa-4,9-diaza-spiro[5... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Secondary amine | c1ccccc1.C1CC2(CC[NH]1)C[NH]CCO2 | C1CC2(CCN1)C[NH]CCO2 | c1ccccc1.C1CC2(CCN1)C[NH]CCO2.c1ccccc1 | HO- | [Pd].C(C)O | null | null | CC(C)COc1ccc(CN2C(=O)COC3(CCN(C(=O)OCc4ccccc4)CC3)C2Cc2ccc(F)cc2)cc1>[Pd].C(C)O>CC(C)COc1ccc(CN2C(=O)COC3(CCNCC3)C2Cc2ccc(F)cc2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-52db395872194545a29f7d1756c837d4 | CC(C)(C)OC(=O)N1CCC2(CC1)CC(=O)NN2Cc1ccc(F)cc1.CC(C)COc1ccc(CBr)cc1>>CC(C)COc1ccc(CN2C(=O)CC3(CCN(C(=O)OC(C)(C)C)CC3)N2Cc2ccc(F)cc2)cc1 | C(C(C)C)OC1=CC=C(CBr)C=C1.[H-].[Na+].C(C)(C)(C)OC(=O)N1CCC2(CC(NN2CC2=CC=C(C=C2)F)=O)CC1>>C(C)(C)(C)OC(=O)N1CCC2(CC(N(N2CC2=CC=C(C=C2)F)CC2=CC=C(C=C2)OCC(C)C)=O)CC1 | [NH:11]1[C:12](=[O:13])[CH2:14][C:15]2([CH2:16][CH2:17][N:18]([C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:26][CH2:27]2)[N:28]1[CH2:29][c:30]1[cH:31][cH:32][c:33]([F:34])[cH:35][cH:36]1.Br[CH2:10][c:9]1[cH:8][cH:7][c:6]([O:5][CH2:4][CH:2]([CH3:1])[CH3:3])[cH:38][cH:37]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][O:... | CC(C)(C)OC(=O)N1CCC2(CC1)CC(=O)NN2Cc1ccc(F)cc1.CC(C)COc1ccc(CBr)cc1 | CC(C)COc1ccc(CN2C(=O)CC3(CCN(C(=O)OC(C)(C)C)CC3)N2Cc2ccc(F)cc2)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 1d484d72d1392e1118014cca6a59232f66680d8dcaf2d43a944390da5b781fb8 | 75fa53fcea00b2bf91faff8a86bd2b4c6e278499b46cc76f6552f3496df57ac7 | O=C1CC2(CCNCC2)N(Cc2ccccc2)N1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#7:6]1-[C:7]-[C:8]-[C:9](=[O;D1;H0:10])-[NH;D2;+0:11]-1>>[C:5]-[#7:6]1-[C:7]-[C:8]-[C:9](=[O;D1;H0:10])-[N;H0;D3;+0:11]-1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 50.6 | [{"value": 50.0, "product": "C(C)(C)(C)OC(=O)N1CCC2(CC(N(N2CC2=CC=C(C=C2)F)CC2=CC=C(C=C2)OCC(C)C)=O)CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.6, "product": "C(C)(C)(C)OC(=O)N1CCC2(CC(N(N2CC2=CC=C(C=C2)F)CC2=CC=C(C=C2)OCC(C)C)=O)CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | NaH (24 mg, 0.50 mmol) was added slowly to a solution of 84AF84-19 (0.149 g, 0.41 mmol) in dry DMF (5 mL) and the mixture stirred at rt for 30 min. A solution of 4-isobutoxybenzyl bromide 69NLS69 (117 mg, 0.48 mmol) in dry DMF (1 mL) was added dropwise to the mixture. After 1 h stirring at rt the mixture was partitione... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Primary halide | Acylhydrazine | C1CC2(CC[NH]1)CCN[NH]2 | C1CC2(CC[NH]1)CC[NH][NH]2 | c1ccccc1.C1CC2(CC[NH]1)CC[NH][NH]2.c1ccccc1 | HBr | CN(C)C=O | null | 0.5 | CC(C)(C)OC(=O)N1CCC2(CC1)CC(=O)NN2Cc1ccc(F)cc1.CC(C)COc1ccc(CBr)cc1>CN(C)C=O>CC(C)COc1ccc(CN2C(=O)CC3(CCN(C(=O)OC(C)(C)C)CC3)N2Cc2ccc(F)cc2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-b365b3cf20f740868d5dd9e747f42a18 | CC1(C)NCc2ccccc2O1>>CC(C)Nc1ccccc1CO | CC1(OC2=C(CN1)C=CC=C2)C.C1CCOC1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C1CCOC1>>C(C)(C)NC1=C(C=CC=C1)CO | [CH3:1][C:2]1([CH3:3])[NH:4][CH2:11][c:10]2[c:5]([cH:6][cH:7][cH:8][cH:9]2)[O:12]1>>[CH3:1][CH:2]([CH3:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[CH2:11][OH:12] | CC1(C)NCc2ccccc2O1 | CC(C)Nc1ccccc1CO | null | null | null | Miscellaneous | OtherReaction | bf0fd08faea41f249ad245c627ae5eaa44305b733aa8f021166c9982d83d6e4c | 6731e713966699a550554bf52935dfe7a2b2eb2cafc83e524d2ff6fcc59af15d | c1ccccc1 | [C;D1;H3:1]-[C;H0;D4;+0:2]1(-[C;D1;H3:3])-[NH;D2;+0:4]-[CH2;D2;+0:5]-[c:6](:[c:7]):[c;H0;D3;+0:8](:[c:9]:[c:10])-[O;H0;D2;+0:11]-1>>[C;D1;H3:1]-[CH;D3;+0:2](-[C;D1;H3:3])-[NH;D2;+0:4]-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:6](-[CH2;D2;+0:5]-[OH;D1;+0:11]):[c:7] | 95 | [{"value": 95.0, "product": "C(C)(C)NC1=C(C=CC=C1)CO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of 2,2,-dimethyl-1,4-dihydro-2H-benzo[1,3]oxazine (125 g, 0.77 mol) in THF (1 L) was filtered through a scintillation funnel and then added dropwise via an addition funnel, over a period of 2.5 h, to a stirred solution of 1.0 M LiAlH4 in THF (800 mL) at 0° C. The reaction was quenched by slow portionwise add... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Primary alcohol.Secondary amine | c1ccc2c(c1)CNCO2 | c1ccccc1 | c1ccccc1 | null | null | null | 8 | CC1(C)NCc2ccccc2O1>>CC(C)Nc1ccccc1CO |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-0b646f22560f477fb1da598dcb7191c5 | CC(C)Nc1ccccc1CO>>CC(C)Nc1ccccc1C=O | C(C)(C)NC1=C(C=CC=C1)CO>>C(C)(C)NC1=C(C=O)C=CC=C1 | [CH3:1][CH:2]([CH3:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[CH2:11][OH:12]>>[CH3:1][CH:2]([CH3:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[CH:11]=[O:12] | CC(C)Nc1ccccc1CO | CC(C)Nc1ccccc1C=O | null | [O-2].[O-2].[Mn+4] | C1(=CC=CC=C1)C | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccccc1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5] | 90.6 | [{"value": 90.0, "product": "C(C)(C)NC1=C(C=O)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.6, "product": "C(C)(C)NC1=C(C=O)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 117 | CELSIUS | null | null | Manganese dioxide (85% 182.6 g, 1.79 mol) was added to a stirred solution of 2-isopropylaminophenylmethanol (118 g, 0.71 mol) in toluene (800 mL) and the reaction mixture was heated to 117° C. for 4 h. The reaction mixture was allowed to cool to room temperature overnight and then filtered through a pad of Celite which... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1 | null | [O-2].[O-2].[Mn+4].C1(=CC=CC=C1)C | 117 | null | CC(C)Nc1ccccc1CO>[O-2].[O-2].[Mn+4].C1(=CC=CC=C1)C>CC(C)Nc1ccccc1C=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-109dac685285458ca4e56162f94f2f99 | CC(C)Nc1ccccc1C=O.CC1(C)OC(=O)CC(=O)O1>>CC(C)n1c(=O)c(C(=O)O)cc2ccccc21 | CC1(OC(CC(O1)=O)=O)C.CC1(OC(=O)CC(=O)O1)C.C(C)(C)NC1=C(C=O)C=CC=C1.C(C)(=O)O.C(CN)N>>C(C)(C)N1C(C(=CC2=CC=CC=C12)C(=O)O)=O | O=[CH:11][c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[NH:4][CH:2]([CH3:1])[CH3:3].CC1(C)O[C:5](=[O:6])[CH2:7][C:8](=[O:9])[O:10]1>>[CH3:1][CH:2]([CH3:3])[n:4]1[c:5](=[O:6])[c:7]([C:8](=[O:9])[OH:10])[cH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12 | CC(C)Nc1ccccc1C=O.CC1(C)OC(=O)CC(=O)O1 | CC(C)n1c(=O)c(C(=O)O)cc2ccccc21 | null | null | CO | Miscellaneous | OtherReaction | 7da7c8932064b44b257d05fda8b8362a79f28b679166e64d691318db6946232e | ddbf93ce274a07b125aec0b5e9bfc602f13d41e2bbc449e0d8b2eac033b184d0 | O=c1ccc2ccccc2[nH]1 | C-C1(-C)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-1.O=[CH;D2;+0:7]-[c:8](:[c:9]):[c:10](-[NH;D2;+0:11]-[C:12](-[C;D1;H3:13])-[C;D1;H3:14]):[c:15]>>[C;D1;H3:13]-[C:12](-[C;D1;H3:14])-[n;H0;D3;+0:11]1:[c:10](:[c:15]):[c:8](:[c:9]):[cH;D2;+0:7]:[c;H0;D3;+0:3](-[C:4](=[O;D1;H0:5])-[OH... | 98 | [{"value": 98.0, "product": "C(C)(C)N1C(C(=CC2=CC=CC=C12)C(=O)O)=O", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | 2,2-Dimethyl-[1,3]dioxane-4,6-dione, commonly Meldrum's acid, (166.9 g, 1.16 mol) was added to a stirred solution of 2-isopropylaminobenzaldehyde (105 g, 0.64 mol), acetic acid (73.6 mL, 1.29 mol) and ethylenediamine (43.0 mL, 0.64 mol) in methanol (1 L) at 0° C. The reaction mixture was stirred for 1 h at 0° C. and th... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester.Ester.Secondary amine | Carboxylic acid | c1ccccc1.C1COCOC1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HO- | CO | 0 | 1 | CC(C)Nc1ccccc1C=O.CC1(C)OC(=O)CC(=O)O1>CO>CC(C)n1c(=O)c(C(=O)O)cc2ccccc21 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-82aaae6093db42fe87e71f8ee3f2a71f | CN(C[C@H](O)CCl)C(=O)OC(C)(C)C>>CN(C[C@H]1CO1)C(=O)OC(C)(C)C | C(C)(C)(C)OC(N(C)C[C@@H](CCl)O)=O.[OH-].[Na+]>>C(C)(C)(C)OC(N(C[C@@H]1OC1)C)=O | Cl[CH2:5][C@H:4]([CH2:3][N:2]([CH3:1])[C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[OH:6]>>[CH3:1][N:2]([CH2:3][C@H:4]1[CH2:5][O:6]1)[C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13] | CN(C[C@H](O)CCl)C(=O)OC(C)(C)C | CN(C[C@H]1CO1)C(=O)OC(C)(C)C | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis (intra to epoxy) | ebf120e9288f48b61f87dafb00b4bacd480e273fa54208a20ed1d8b8a8581b3e | 9d3e82e8fa4f4bc62c1019e0bd869bdb0cf4748977f3c0b945b8ffdfc70126be | C1CO1 | Cl-[CH2;D2;+0:1]-[C:2](-[C:3])-[OH;D1;+0:4]>>[C:3]-[C:2]1-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-1 | 85.5 | [{"value": 85.5, "product": "C(C)(C)(C)OC(N(C[C@@H]1OC1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | ((S)-3-chloro-2-hydroxypropyl)-methylcarbamic acid tert-butyl ester (2.23 g, 10 mmol) was dissolved in THF (30 mL), and then an aqueous sodium hydroxide solution (0.48 g in 10 mL water) was added. The mixture was stirred for 2 h. The mixture was then concentrated under reduced pressure to remove most of the THF, and th... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary alcohol | Ether | null | C1CO1 | C1CO1 | HCl | C1CCOC1 | null | 2 | CN(C[C@H](O)CCl)C(=O)OC(C)(C)C>C1CCOC1>CN(C[C@H]1CO1)C(=O)OC(C)(C)C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-0fb31da23a524499978fccaaf3c41b28 | O=C1NC(=O)c2ccccc21.OC[C@H]1CO1>>O=C1c2ccccc2C(=O)N1C[C@H]1CO1 | O1[C@H](C1)CO.C1(C=2C(C(N1)=O)=CC=CC2)=O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.N(=NC(=O)OCC)C(=O)OCC>>O1[C@H](C1)CN1C(C2=CC=CC=C2C1=O)=O | [O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[NH:11]1.O[CH2:12][C@H:13]1[CH2:14][O:15]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][C@H:13]1[CH2:14][O:15]1 | O=C1NC(=O)c2ccccc21.OC[C@H]1CO1 | O=C1c2ccccc2C(=O)N1C[C@H]1CO1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Mitsunobu_imide | 16aabf490ad1bd0cd53a985dff922c76188147a3ad5bf7d09c4c1e93a9e46a19 | 8a66434962da2945c8a8685e3bd4f60c7955241df224c95aa14ead6db9d240f9 | O=C1c2ccccc2C(=O)N1C[C@H]1CO1 | O-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1.[O;D1;H0:5]=[C:6]1-[NH;D2;+0:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11]-1>>[O;D1;H0:5]=[C:6]1-[c:11]:[c:10]-[C:8](=[O;D1;H0:9])-[N;H0;D3;+0:7]-1-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1 | 73.9 | [{"value": 73.9, "product": "O1[C@H](C1)CN1C(C2=CC=CC=C2C1=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 48 | HOUR | To a cold solution of (S)-1-oxiranylmethanol (5 g, 67.5 mmol) and phthalimide (9.9 g, 67.3 mmol) in tetrahydrofuran (200 mL) in ice bath was added triphenylphosphine (17.9 g, 68.2 mmol) and diethyl azodicarboxylate (12.3 g, 70.6 mmol). The mixture was stirred at 0° C. for 2 h and at ambient temperature for 48 h. The mi... | 10.6084/m9.figshare.5104873.v1 | null | Unsubstituted dicarboximide.Primary alcohol | Substituted dicarboximide | c1ccc2c(c1)CNC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1CO1 | HO- | O1CCCC1 | 0 | 48 | O=C1NC(=O)c2ccccc21.OC[C@H]1CO1>O1CCCC1>O=C1c2ccccc2C(=O)N1C[C@H]1CO1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-7d46aa2551e64e31b61c95a914fb29be | CS(N)(=O)=O.ClC[C@@H]1CO1>>NS(=O)(=O)CC[C@H]1CO1 | Cl.ClC[C@H]1OC1.CS(=O)(=O)N.[OH-].[Na+]>>O1[C@H](C1)CCS(=O)(=O)N | [NH2:1][S:2](=[O:3])(=[O:4])[CH3:5].Cl[CH2:6][C@@H:7]1[CH2:8][O:9]1>>[NH2:1][S:2](=[O:3])(=[O:4])[CH2:5][CH2:6][C@H:7]1[CH2:8][O:9]1 | CS(N)(=O)=O.ClC[C@@H]1CO1 | NS(=O)(=O)CC[C@H]1CO1 | null | null | O | C-C Coupling | OtherReaction | 15973705e8ad8fc52aace4e951dc2397c95f8af8fb2361e425388262f1895099 | f5e5e22797736d188bba28deb76a4cee8e4fee4dca04fe24f733d2ee68a23361 | C1CO1 | Cl-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1.[CH3;D1;+0:5]-[#16:6](-[N;D1;H2:7])(=[O;D1;H0:8])=[O;D1;H0:9]>>[N;D1;H2:7]-[#16:6](=[O;D1;H0:8])(=[O;D1;H0:9])-[CH2;D2;+0:5]-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1 | 15.7 | [{"value": 15.7, "product": "O1[C@H](C1)CCS(=O)(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a cold solution of methanesulfonamide (10 g, 0.105 mol) in water (100 mL) in an ice bath was added sodium hydroxide as pellets (8.4 g, 0.21 mol) and then (S)-2-chloromethyloxirane (12.4 g, 0.158 mol). The mixture was stirred at the same temperature for 2 h, and at room temperature for 12 h and then concentrated hydr... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | C1CO1 | HCl | O | null | 2 | CS(N)(=O)=O.ClC[C@@H]1CO1>O>NS(=O)(=O)CC[C@H]1CO1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-8176c417bb3d43bcb407f645c6af29c0 | CC(C)=CC(=O)Cl.Nc1ccccc1>>CC1(C)CC(=O)Nc2ccccc21 | NC1=CC=CC=C1.CC(=CC(=O)Cl)C>>CC1(CC(NC2=CC=CC=C12)=O)C | Cl[C:5]([CH:4]=[C:2]([CH3:1])[CH3:3])=[O:6].[NH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]21 | CC(C)=CC(=O)Cl.Nc1ccccc1 | CC1(C)CC(=O)Nc2ccccc21 | null | null | C(Cl)(Cl)Cl | Acylation | OtherReaction | 8ee6db14bea61634c1db7b2cae63ea8b50308689aec0e9e8c9c6174f240ad9f2 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCc2ccccc2N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D2;+0:3]=[C;H0;D3;+0:4](-[C;D1;H3:5])-[C;D1;H3:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11]:[c:12]>>[C;D1;H3:5]-[C;H0;D4;+0:4]1(-[C;D1;H3:6])-[CH2;D2;+0:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[c:8](:[c:9]):[c;H0;D3;+0:10]-1:[c:11]:[c:12] | null | [] | 80 | CELSIUS | null | null | Aniline (7.26 g, 45.2 mmol) and 3-methylbut-2-enoyl chloride (53.2 g, 45.2 mmol) were heated in chloroform at reflux for 2 h. After cooling, the mixture was filtered. The filtrate was concentrated to dryness and dried under vacuum. The crude 3-methyl-but-2-enoic acid phenylamide (ca. 10 g) was dissolved in toluene (50 ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | c1ccccc1 | c1ccc2c(c1)CCCN2 | c1ccc2c(c1)CCCN2 | HCl | C(Cl)(Cl)Cl | 80 | null | CC(C)=CC(=O)Cl.Nc1ccccc1>C(Cl)(Cl)Cl>CC1(C)CC(=O)Nc2ccccc21 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-fb667311067c4e2380c096bb5a2c1403 | CC1(C)CC(=O)Nc2ccccc21>>CC1(C)CCNc2ccccc21 | [H-].[H-].[H-].[H-].[Li+].[Al+3].CC1(CC(NC2=CC=CC=C12)=O)C.[O-]S(=O)(=O)[O-].[Na+].[Na+].[H-].[H-].[H-].[H-].[Li+].[Al+3]>>CC1(CCNC2=CC=CC=C12)C | O=[C:5]1[CH2:4][C:2]([CH3:1])([CH3:3])[c:12]2[c:7]([cH:8][cH:9][cH:10][cH:11]2)[NH:6]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][NH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]21 | CC1(C)CC(=O)Nc2ccccc21 | CC1(C)CCNc2ccccc21 | null | null | C1CCOC1 | Reduction | Reduction of secondary amides to amines | 788a8d0e853f94332dfbb9ba2e19be4ef643430c4f1cc6825c96cd2edba7148d | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1ccc2c(c1)CCCN2 | O=[C;H0;D3;+0:1](-[#7:2]-[c:3])-[C:4]-[C:5]>>[C:5]-[C:4]-[CH2;D2;+0:1]-[#7:2]-[c:3] | 93 | [{"value": 93.0, "product": "CC1(CCNC2=CC=CC=C12)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred solution of LiAlH4 (1.0 M in THF, 35 mL, 35 mmol), was added a solution of 1a. (2.17 g, 12.4 mmol) in THF (10 mL) for 5 min at 0° C. under nitrogen. The resulting mixture was warmed gradually to reflux, and heated at reflux for 5.5 h. To the cooled mixture with stirring, was added sat'd Na2SO4 dropwise til... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1ccc2c(c1)CCCN2 | c1ccc2c(c1)CCCN2 | c1ccc2c(c1)CCCN2 | Other | C1CCOC1 | null | null | CC1(C)CC(=O)Nc2ccccc21>C1CCOC1>CC1(C)CCNc2ccccc21 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-6f4b0b70237f463091d7218d522edefa | CC1(C)CCNc2ccccc21.O=[N+]([O-])c1ccccc1F>>CC1(C)CCN(c2ccccc2[N+](=O)[O-])c2ccccc21 | CC1(CCNC2=CC=CC=C12)C.FC1=C(C=CC=C1)[N+](=O)[O-].N1=C(C=C(C=C1C)C)C>>CC1(CCN(C2=CC=CC=C12)C1=C(C=CC=C1)[N+](=O)[O-])C | [CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][NH:6][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]21.F[c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[N+:13](=[O:14])[O-:15]>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][N:6]([c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[N+:13](=[O:14])[O-:15])[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]21 | CC1(C)CCNc2ccccc21.O=[N+]([O-])c1ccccc1F | CC1(C)CCN(c2ccccc2[N+](=O)[O-])c2ccccc21 | null | null | C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | de606d160ccc80ef355eabdb340e2f4f96955660dd0088ab61ab49bbb46dfbde | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCCc3ccccc32)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[C:7]-[C:8]-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:9](-[C:8]-[C:7])-[c:10](:[c:11]):[c:12]):[c:2]:[c:3] | null | [] | 250 | CELSIUS | 1 | HOUR | 1b (0.762 g, 4.73 mmol), ortho-fluoronitrobenzene (0.88 g, 5.67 mmol, 1.19 eq), and 2,4,6-collidine (0.66 mL, 1.05 eq) were pre-stirred 40s in a conical microwave container. It was then heated with stirring at a Personal Chemistry Microwave reactor with normal absorption at 250° C. for 1 h. The crude mixture was dissol... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2c(c1)CCCN2.c1ccccc1 | c1ccccc1.c1ccc2c(c1)CCC[NH]2 | c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HF | C(Cl)(Cl)Cl | 250 | 1 | CC1(C)CCNc2ccccc21.O=[N+]([O-])c1ccccc1F>C(Cl)(Cl)Cl>CC1(C)CCN(c2ccccc2[N+](=O)[O-])c2ccccc21 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-2a90426445fb4e3f9d543bc95254b264 | CC1(C)CCN(c2ccccc2[N+](=O)[O-])c2ccccc21>>CC1(C)CCN(c2ccccc2N)c2ccccc21 | CC1(CCN(C2=CC=CC=C12)C1=C(C=CC=C1)[N+](=O)[O-])C.[NH4+].[Cl-]>>CC1(CCN(C2=CC=CC=C12)C1=C(C=CC=C1)N)C | O=[N+:13]([O-])[c:12]1[c:7]([N:6]2[CH2:5][CH2:4][C:2]([CH3:1])([CH3:3])[c:19]3[c:14]2[cH:15][cH:16][cH:17][cH:18]3)[cH:8][cH:9][cH:10][cH:11]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][N:6]([c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[NH2:13])[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]21 | CC1(C)CCN(c2ccccc2[N+](=O)[O-])c2ccccc21 | CC1(C)CCN(c2ccccc2N)c2ccccc21 | null | [Zn] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(N2CCCc3ccccc32)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 73 | [{"value": 73.0, "product": "CC1(CCN(C2=CC=CC=C12)C1=C(C=CC=C1)N)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.9, "product": "CC1(CCN(C2=CC=CC=C12)C1=C(C=CC=C1)N)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | The crude 1c (0.66 g) was stirred in MeOH (20 mL) at rt. Solid NH4Cl (0.62 g) was added, followed by addition of Zn dust (3.0 g) portionwise. The resulting mixture was stirred at rt for 2 h. It was filtered through Celite®, rinsed with CH2Cl2, and concentrated to dryness. The residue was purified by flash chromatograph... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | [Zn].CO | null | 2 | CC1(C)CCN(c2ccccc2[N+](=O)[O-])c2ccccc21>[Zn].CO>CC1(C)CCN(c2ccccc2N)c2ccccc21 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-f29cdedad1cb4ee98680c27ced2d0799 | CC1(C)CCN(c2ccccc2N)c2ccccc21.O=C(N=C=S)c1ccccc1>>CC1(C)CCN(c2ccccc2NC(=S)NC(=O)c2ccccc2)c2ccccc21 | CC1(CCN(C2=CC=CC=C12)C1=C(C=CC=C1)N)C.C(C1=CC=CC=C1)(=O)N=C=S>>C(C1=CC=CC=C1)(=O)NC(=S)NC1=C(C=CC=C1)N1CCC(C2=CC=CC=C12)(C)C | [CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][N:6]([c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[NH2:13])[c:25]2[cH:26][cH:27][cH:28][cH:29][c:30]21.[C:14](=[S:15])=[N:16][C:17](=[O:18])[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][N:6]([c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[NH:13][C:14](=[S:15])[... | CC1(C)CCN(c2ccccc2N)c2ccccc21.O=C(N=C=S)c1ccccc1 | CC1(C)CCN(c2ccccc2NC(=S)NC(=O)c2ccccc2)c2ccccc21 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | thiourea | 9037f368cdf8e91fcd9f93f4d9cf27991f85fa921c9d19c7875d3a77561f439b | 0fbf3d6c8cd704ac451c2cf111f32090de5e76a9d41cce326e212c758f4ed46f | O=C(NC(=S)Nc1ccccc1N1CCCc2ccccc21)c1ccccc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6](-[c:7])-[N;H0;D2;+0:8]=[C;H0;D2;+0:9]=[S;D1;H0:10]>>[O;D1;H0:5]=[C:6](-[c:7])-[NH;D2;+0:8]-[C;H0;D3;+0:9](=[S;D1;H0:10])-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 4 | MINUTE | 1d (65.4 mg, mmol) and benzoyl isothiocyanate (60 mg) were heated at refluxing CH2Cl2 for 2 h. After cooling, the solvent was evaporated. The resulting crude 1e was dried over vacuum and used directly in the next step: LC-MS ESI, 416.3 (M+H) (10-90% MeOH in H2O with 0.1% TFA in a 4 min run, tR=4.49 min).
Conditions: Se... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Isothiocyanate | Thiourea | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | null | C(Cl)Cl | null | 0.066667 | CC1(C)CCN(c2ccccc2N)c2ccccc21.O=C(N=C=S)c1ccccc1>C(Cl)Cl>CC1(C)CCN(c2ccccc2NC(=S)NC(=O)c2ccccc2)c2ccccc21 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-a7734ec7f6ab472a91dc21117afbdc06 | CC(=O)OC(C)=O.O=C1Cc2ccccc2N1>>CC(=O)N1C(=O)Cc2ccccc21 | N1C(CC2=CC=CC=C12)=O.C(C)(=O)OC(C)=O>>C(C)(=O)N1C(CC2=CC=CC=C12)=O | CC(=O)O[C:2]([CH3:1])=[O:3].[NH:4]1[C:5](=[O:6])[CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]21>>[CH3:1][C:2](=[O:3])[N:4]1[C:5](=[O:6])[CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]21 | CC(=O)OC(C)=O.O=C1Cc2ccccc2N1 | CC(=O)N1C(=O)Cc2ccccc21 | null | null | null | Acylation | Aminolysis of esters | 4a0f25f96b85e6dba36941728b4336dc91b0f1a4d810a1dfde51aa5c4671f3af | 6ade37977f95c6b33058b518e7f2719ed63964406d89a7d8f0d2f46ad042f783 | O=C1Cc2ccccc2N1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[O;D1;H0:4]=[C:5]1-[C:6]-[c:7]:[c:8](:[c:9])-[NH;D2;+0:10]-1>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[N;H0;D3;+0:10]1-[C:5](=[O;D1;H0:4])-[C:6]-[c:7]:[c:8]-1:[c:9] | 93.7 | [{"value": 93.7, "product": "C(C)(=O)N1C(CC2=CC=CC=C12)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Indoline-2-one (6.65 g, 50 mmol) and acetic anhydride (9 mL) were heated at reflux for 15 h. After cooling, the product was filtered and rinsed with Et2O to give 2a as solids after vacuum drying (8.2 g, yield: 93.7 %).
Conditions: See reaction.notes.procedure_details.
Workup: at reflux for 15 h; After cooling; the prod... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Secondary amide | Substituted dicarboximide | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | HO- | null | null | null | CC(=O)OC(C)=O.O=C1Cc2ccccc2N1>>CC(=O)N1C(=O)Cc2ccccc21 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-9029ee7d927a4fbb8244c6b1fa62d2e0 | CC(=O)N1C(=O)C(C)(C)c2ccccc21>>CC1(C)C(=O)Nc2ccccc21 | C(C)(=O)N1C(C(C2=CC=CC=C12)(C)C)=O>>CC1(C(NC2=CC=CC=C12)=O)C | CC(=O)[N:6]1[C:4](=[O:5])[C:2]([CH3:1])([CH3:3])[c:12]2[c:7]1[cH:8][cH:9][cH:10][cH:11]2>>[CH3:1][C:2]1([CH3:3])[C:4](=[O:5])[NH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]21 | CC(=O)N1C(=O)C(C)(C)c2ccccc21 | CC1(C)C(=O)Nc2ccccc21 | null | null | Cl | Reduction | Hydrogenolysis of tertiary amines | 80c9afefdde9fcdbd74c9f96895cbbe7989127ae61415828fd042ea02129e804 | 15328f7911cf420e5b98cd32bf65857f1b0cf0d0f9e28f1ac7b23b1642c85385 | O=C1Cc2ccccc2N1 | C-C(=O)-[N;H0;D3;+0:1]1-[C:2](=[O;D1;H0:3])-[C:4]-[c:5]:[c:6]-1:[c:7]>>[O;D1;H0:3]=[C:2]1-[C:4]-[c:5]:[c:6](:[c:7])-[NH;D2;+0:1]-1 | 97 | [{"value": 97.0, "product": "CC1(C(NC2=CC=CC=C12)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred solution of 2a (3.2 g, 18.29 mmol) in dry THF (100 mL) was added MeI (2.6 mL, 41.75 mmol, 2.3 eq), followed by the addition of 18-crown-6 (0.51 g, 4.57 mmol, 0.25 eq) at −78° C. under nitrogen. Potassium tert-butoxide (5.12 g, 45.73 mmol, 2.5 eq) was added portionwise. The resulting slurry was stirred at −... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Secondary amide | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | HO- | Cl | null | null | CC(=O)N1C(=O)C(C)(C)c2ccccc21>Cl>CC1(C)C(=O)Nc2ccccc21 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-70d38a8023884add82d24635b21014d4 | CC1(C)C(=O)Nc2ccccc21>>CC1(C)CNc2ccccc21 | [H-].[H-].[H-].[H-].[Li+].[Al+3].CC1(C(NC2=CC=CC=C12)=O)C>>CC1(CNC2=CC=CC=C12)C | O=[C:4]1[C:2]([CH3:1])([CH3:3])[c:11]2[c:6]([cH:7][cH:8][cH:9][cH:10]2)[NH:5]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][NH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]21 | CC1(C)C(=O)Nc2ccccc21 | CC1(C)CNc2ccccc21 | null | null | C1CCOC1 | Reduction | Reduction of secondary amides to amines | 14430205f26667cd66e23b715371e83785a71451171ce975635f0a49b8be93ba | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1ccc2c(c1)CCN2 | O=[C;H0;D3;+0:1]1-[#7:2]-[c:3]:[c:4]-[C:5]-1(-[C;D1;H3:6])-[C;D1;H3:7]>>[C;D1;H3:6]-[C:5]1(-[C;D1;H3:7])-[CH2;D2;+0:1]-[#7:2]-[c:3]:[c:4]-1 | 56 | [{"value": 56.0, "product": "CC1(CNC2=CC=CC=C12)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.0, "product": "CC1(CNC2=CC=CC=C12)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a 1M of LAH (30 mL) in THF was added 2b (630 mg, 3.88 mmol) in portion. The reaction mixture was stirred at rt for 2 h, then refluxed for 1 h. The reaction mixture was quench with 1 part of H2O (10-mL), one part of 15% NaOH (5 mL) and another part of H2O (5 mL). The aqueous layer was extracted with EtOAc. The EtOAc ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | Other | C1CCOC1 | null | 2 | CC1(C)C(=O)Nc2ccccc21>C1CCOC1>CC1(C)CNc2ccccc21 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-c8b49cfec5fa471483c52646642798ca | CC1(C)CNc2ccccc21.O=[N+]([O-])c1ccccc1F>>CC1(C)CN(c2ccccc2[N+](=O)[O-])c2ccccc21 | CC1(CNC2=CC=CC=C12)C.FC1=C(C=CC=C1)[N+](=O)[O-]>>CC1(CN(C2=CC=CC=C12)C1=C(C=CC=C1)[N+](=O)[O-])C | [CH3:1][C:2]1([CH3:3])[CH2:4][NH:5][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]21.F[c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[N+:12](=[O:13])[O-:14]>>[CH3:1][C:2]1([CH3:3])[CH2:4][N:5]([c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[N+:12](=[O:13])[O-:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]21 | CC1(C)CNc2ccccc21.O=[N+]([O-])c1ccccc1F | CC1(C)CN(c2ccccc2[N+](=O)[O-])c2ccccc21 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 9e8e9aaf4acc811e562cf790158519b82ba53be90e2b03c3f89b27d2ed61180c | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCc3ccccc32)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[c:7]:[c:8]1:[c:9]-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:12]1-[C:11]-[C:10]-[c:9]:[c:8]-1:[c:7]):[c:2]:[c:3] | 95 | [{"value": 95.0, "product": "CC1(CN(C2=CC=CC=C12)C1=C(C=CC=C1)[N+](=O)[O-])C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.5, "product": "CC1(CN(C2=CC=CC=C12)C1=C(C=CC=C1)[N+](=O)[O-])C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 175 | CELSIUS | 8 | HOUR | To 2c (317 mg, 2.12 mmol) was added 1-fluoro-2-nitrobenzene (200 mg, 1.42 mmol). The reaction mixture was stirred at 175° C. for 8 h. The reaction mixture was diluted with CH2Cl2 and washed with 1N HCl and dried over Na2SO4. The solvent was evaporated under reduced pressure and purified by column chromatography using 0... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2c(c1)CCN2.c1ccccc1 | c1ccccc1.c1ccc2c(c1)CC[NH]2 | c1ccccc1.c1ccc2c(c1)CC[NH]2 | HF | C(Cl)Cl | 175 | 8 | CC1(C)CNc2ccccc21.O=[N+]([O-])c1ccccc1F>C(Cl)Cl>CC1(C)CN(c2ccccc2[N+](=O)[O-])c2ccccc21 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-2d97adb45bb645f0a3b8015f8ad9b6eb | CC1(C)CN(c2ccccc2[N+](=O)[O-])c2ccccc21>>CC1(C)CN(c2ccccc2N)c2ccccc21 | CC1(CN(C2=CC=CC=C12)C1=C(C=CC=C1)[N+](=O)[O-])C>>CC1(CN(C2=CC=CC=C12)C1=C(C=CC=C1)N)C | O=[N+:12]([O-])[c:11]1[c:6]([N:5]2[CH2:4][C:2]([CH3:1])([CH3:3])[c:18]3[c:13]2[cH:14][cH:15][cH:16][cH:17]3)[cH:7][cH:8][cH:9][cH:10]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][N:5]([c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[NH2:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]21 | CC1(C)CN(c2ccccc2[N+](=O)[O-])c2ccccc21 | CC1(C)CN(c2ccccc2N)c2ccccc21 | null | [Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(N2CCc3ccccc32)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 75 | [{"value": 75.0, "product": "CC1(CN(C2=CC=CC=C12)C1=C(C=CC=C1)N)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.3, "product": "CC1(CN(C2=CC=CC=C12)C1=C(C=CC=C1)N)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 2d (123 mg, 0.458 mmol) in MeOH was added 10% Pd/C (20 mg). The reaction mixture was stirred at rt under H2 for 2 h. The catalyst was filtered through a cake of Celite® and the filtrate was evaporated under reduced pressure to afford 2e (80 mg, 75%) as a yellowish powder. MS (ES) m/z 239 [M+H]+.
Condit... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccc2c(c1)CC[NH]2 | Other | [Pd].CO | null | 2 | CC1(C)CN(c2ccccc2[N+](=O)[O-])c2ccccc21>[Pd].CO>CC1(C)CN(c2ccccc2N)c2ccccc21 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-5b1739874cf74cd0a4adf4f3312b5832 | CC1(C)CN(c2ccccc2N)c2ccccc21.O=C(N=C=S)c1ccccc1>>CC1(C)CN(c2ccccc2NC(=S)NC(=O)c2ccccc2)c2ccccc21 | CC1(CN(C2=CC=CC=C12)C1=C(C=CC=C1)N)C.C(C1=CC=CC=C1)(=O)N=C=S>>C(C1=CC=CC=C1)(=O)NC(=S)NC1=C(C=CC=C1)N1CC(C2=CC=CC=C12)(C)C | [CH3:1][C:2]1([CH3:3])[CH2:4][N:5]([c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[NH2:12])[c:24]2[cH:25][cH:26][cH:27][cH:28][c:29]21.[C:13](=[S:14])=[N:15][C:16](=[O:17])[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][N:5]([c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[NH:12][C:13](=[S:14])[NH:15][C:16](=[O... | CC1(C)CN(c2ccccc2N)c2ccccc21.O=C(N=C=S)c1ccccc1 | CC1(C)CN(c2ccccc2NC(=S)NC(=O)c2ccccc2)c2ccccc21 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | thiourea | 9037f368cdf8e91fcd9f93f4d9cf27991f85fa921c9d19c7875d3a77561f439b | 0fbf3d6c8cd704ac451c2cf111f32090de5e76a9d41cce326e212c758f4ed46f | O=C(NC(=S)Nc1ccccc1N1CCc2ccccc21)c1ccccc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6](-[c:7])-[N;H0;D2;+0:8]=[C;H0;D2;+0:9]=[S;D1;H0:10]>>[O;D1;H0:5]=[C:6](-[c:7])-[NH;D2;+0:8]-[C;H0;D3;+0:9](=[S;D1;H0:10])-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 112.7 | [{"value": 99.0, "product": "C(C1=CC=CC=C1)(=O)NC(=S)NC1=C(C=CC=C1)N1CC(C2=CC=CC=C12)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 112.7, "product": "C(C1=CC=CC=C1)(=O)NC(=S)NC1=C(C=CC=C1)N1CC(C2=CC=CC=C12)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2e (40 mg, 0.168 mmol) in CH2Cl2 was added benzoyl isothiocyanate (30 mg, 0.189 mmol). The reaction mixture was kept at reflux for 2.5 h. The reaction mixture was filtered through a cake of Celite® and washed the cake with CH2Cl2. The solvent was evaporated under reduced pressure. The desired product w... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Isothiocyanate | Thiourea | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | null | C(Cl)Cl | null | null | CC1(C)CN(c2ccccc2N)c2ccccc21.O=C(N=C=S)c1ccccc1>C(Cl)Cl>CC1(C)CN(c2ccccc2NC(=S)NC(=O)c2ccccc2)c2ccccc21 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-b622ac2b97c445c8892456fc306c31a0 | CC1(C)CN(c2ccccc2NC(=S)NC(=O)c2ccccc2)c2ccccc21>>CC1(C)CN(c2ccccc2NC(N)=S)c2ccccc21 | C(C1=CC=CC=C1)(=O)NC(=S)NC1=C(C=CC=C1)N1CC(C2=CC=CC=C12)(C)C.[OH-].[Na+]>>CC1(CN(C2=CC=CC=C12)C1=C(C=CC=C1)NC(=S)N)C | O=C(c1ccccc1)[NH:14][C:13]([NH:12][c:11]1[c:6]([N:5]2[CH2:4][C:2]([CH3:1])([CH3:3])[c:21]3[c:16]2[cH:17][cH:18][cH:19][cH:20]3)[cH:7][cH:8][cH:9][cH:10]1)=[S:15]>>[CH3:1][C:2]1([CH3:3])[CH2:4][N:5]([c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[NH:12][C:13]([NH2:14])=[S:15])[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]21 | CC1(C)CN(c2ccccc2NC(=S)NC(=O)c2ccccc2)c2ccccc21 | CC1(C)CN(c2ccccc2NC(N)=S)c2ccccc21 | null | null | CO | Reduction | Hydrogenolysis of amides/imides/carbamates | 6328dabafc97dccec70704aeab9949d588a2e027ae7e309e707f818d6bad9dae | eb308e50ea59a818e9be36da7e60c01d0f7ab2d0f39e89f35847ab33b6eb422f | c1ccc(N2CCc3ccccc32)cc1 | O=C(-[NH;D2;+0:1]-[C:2](=[S;D1;H0:3])-[#7:4]-[c:5])-c1:c:c:c:c:c:1>>[NH2;D1;+0:1]-[C:2](=[S;D1;H0:3])-[#7:4]-[c:5] | null | [] | 50 | CELSIUS | 2 | HOUR | To a solution of 2f (60 mg, 0.149 mmol) in MeOH was added 1N NaOH (0.2 mL, 0.2 mmol). The reaction mixture was stirred at 50° C. for 2 h. The solvent was evaporated under reduced pressure and co-evaporated with toluene to afford 2 g (35 mg, 80%). MS (ES) m/z 298 [M+H]30 .
Conditions: See reaction.notes.procedure_detail... | 10.6084/m9.figshare.5104873.v1 | null | Thiourea.Secondary amide | Thiourea | c1ccccc1 | null | c1ccccc1.c1ccc2c(c1)CC[NH]2 | HO- | CO | 50 | 2 | CC1(C)CN(c2ccccc2NC(=S)NC(=O)c2ccccc2)c2ccccc21>CO>CC1(C)CN(c2ccccc2NC(N)=S)c2ccccc21 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-108cc9d19cef4127a1413be7e6945b05 | CC1(C)CN(c2ncccc2[N+](=O)[O-])c2ccccc21>>CC1(C)CN(c2ncccc2N)c2ccccc21 | CC1(CN(C2=CC=CC=C12)C1=NC=CC=C1[N+](=O)[O-])C>>CC1(CN(C2=CC=CC=C12)C1=NC=CC=C1N)C | O=[N+:12]([O-])[c:11]1[c:6]([N:5]2[CH2:4][C:2]([CH3:1])([CH3:3])[c:18]3[c:13]2[cH:14][cH:15][cH:16][cH:17]3)[n:7][cH:8][cH:9][cH:10]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][N:5]([c:6]2[n:7][cH:8][cH:9][cH:10][c:11]2[NH2:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]21 | CC1(C)CN(c2ncccc2[N+](=O)[O-])c2ccccc21 | CC1(C)CN(c2ncccc2N)c2ccccc21 | null | [Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(N2CCc3ccccc32)nc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4](-[#7:5]):[#7;a:6]:[c:7]>>[#7:5]-[c:4](:[#7;a:6]:[c:7]):[c:2](-[NH2;D1;+0:1]):[c:3] | 76 | [{"value": 76.0, "product": "CC1(CN(C2=CC=CC=C12)C1=NC=CC=C1N)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.3, "product": "CC1(CN(C2=CC=CC=C12)C1=NC=CC=C1N)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 4a (30 mg, 0.111 mmol) in MeOH was added 10% Pd/C (10 mg). The reaction mixture was stirred at rt under H2 for 2 h. The catalyst was filtered through a cake of Celite® and the filtrate was evaporated under reduced pressure to afford 4b (20 mg, 76%) as a yellowish powder. MS (ES) m/z 240 [M+H]+.
Conditi... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccncc1.c1ccc2c(c1)CC[NH]2 | Other | [Pd].CO | null | 2 | CC1(C)CN(c2ncccc2[N+](=O)[O-])c2ccccc21>[Pd].CO>CC1(C)CN(c2ncccc2N)c2ccccc21 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-c5d29f4e98a24783a55178b491c83521 | CC(C)(C)OC(=O)N1CCC2(CC1)CC(=O)c1ccccc12.O=C(O)C(F)(F)F>>O=C1CC2(CCN(C(=O)C(F)(F)F)CC2)c2ccccc21 | C(=O)(C(F)(F)F)O.O=C1CC2(CCN(CC2)C(=O)OC(C)(C)C)C2=CC=CC=C12.C(C)N(CC)CC.FC(C(=O)OC(C(F)(F)F)=O)(F)F>>FC(C(=O)N1CCC2(CC1)CC(C1=CC=CC=C12)=O)(F)F | CC(C)(C)O[C:8]([N:7]1[CH2:6][CH2:5][C:4]2([CH2:3][C:2](=[O:1])[c:21]3[c:16]2[cH:17][cH:18][cH:19][cH:20]3)[CH2:15][CH2:14]1)=[O:9].O=C(O)[C:10]([F:11])([F:12])[F:13]>>[O:1]=[C:2]1[CH2:3][C:4]2([CH2:5][CH2:6][N:7]([C:8](=[O:9])[C:10]([F:11])([F:12])[F:13])[CH2:14][CH2:15]2)[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]21 | CC(C)(C)OC(=O)N1CCC2(CC1)CC(=O)c1ccccc12.O=C(O)C(F)(F)F | O=C1CC2(CCN(C(=O)C(F)(F)F)CC2)c2ccccc21 | null | CN(C)C=1C=CN=CC1 | ClCCl | C-C Coupling | OtherReaction | 20333bc66f3cb5fefdfe7458a63cb0a72a360b73de7f00140facbeb45dfe0d31 | f42ec85720e190dba9e6d13e5b8a954c7b8feaf94771380f41a4b084e1761e1d | O=C1CC2(CCNCC2)c2ccccc21 | C-C(-C)(-C)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C:4])-[C:5].O-C(=O)-[C;H0;D4;+0:6](-[F;D1;H0:7])(-[F;D1;H0:8])-[F;D1;H0:9]>>[C:4]-[#7:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D4;+0:6](-[F;D1;H0:7])(-[F;D1;H0:8])-[F;D1;H0:9])-[C:5] | 92 | [{"value": 92.0, "product": "FC(C(=O)N1CCC2(CC1)CC(C1=CC=CC=C12)=O)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | TFA (25 mL) was added to a solution of commercially available tert-butyl 3-oxo-2,3-dihydrospiro[indene-1,4′-piperidine]-1′-carboxylate (5.0 g, 16.6 mmol) in dichloromethane (25 mL) at 0° C. The reaction was then allowed to warm to rt for 30 min. The reaction was evaporated and dried under high vacuum for 30 min. The cr... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Carbamic ester.Carboxylic acid.Ether.Boc | Trifluoro group.Tertiary amide | null | null | c1ccc2c(c1)CCC21CC[NH]CC1 | HO- | CN(C)C=1C=CN=CC1.ClCCl | null | 2 | CC(C)(C)OC(=O)N1CCC2(CC1)CC(=O)c1ccccc12.O=C(O)C(F)(F)F>CN(C)C=1C=CN=CC1.ClCCl>O=C1CC2(CCN(C(=O)C(F)(F)F)CC2)c2ccccc21 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-e52b15a90a9149b6bff697b334b6add9 | O=C1CC2(CCN(C(=O)C(F)(F)F)CC2)c2ccccc21>>O=C1CC2(CCN(C(=O)C(F)(F)F)CC2)c2ccccc2N1 | OS(=O)(=O)O.[N-]=[N+]=[N-].[Na+].C(=O)(O)[O-].[Na+].OS(=O)(=O)O.FC(C(=O)N1CCC2(CC1)CC(C1=CC=CC=C12)=O)(F)F>>FC(C(=O)N1CCC2(CC(NC3=CC=CC=C23)=O)CC1)(F)F | [O:1]=[C:2]1[CH2:3][C:4]2([CH2:5][CH2:6][N:7]([C:8](=[O:9])[C:10]([F:11])([F:12])[F:13])[CH2:14][CH2:15]2)[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]21>>[O:1]=[C:2]1[CH2:3][C:4]2([CH2:5][CH2:6][N:7]([C:8](=[O:9])[C:10]([F:11])([F:12])[F:13])[CH2:14][CH2:15]2)[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[NH:22]1 | O=C1CC2(CCN(C(=O)C(F)(F)F)CC2)c2ccccc21 | O=C1CC2(CCN(C(=O)C(F)(F)F)CC2)c2ccccc2N1 | null | null | C(Cl)(Cl)Cl.O | Functional Group Addition | Schmidt ketone amide | ac3e9653f7e5f7553b83da5c331f2145489be508cc1ad7572b8ec01d1705f66e | 2eb609f54422c0279557c5451dffbcf43fa7dc53a915eee10665042f34f6a171 | O=C1CC2(CCNCC2)c2ccccc2N1 | [O;D1;H0:1]=[C;H0;D3;+0:2]1-[C:3]-[C:4]-[c:5](:[c:6]):[c;H0;D3;+0:7]-1:[c:8]:[c:9]>>[O;D1;H0:1]=[C;H0;D3;+0:2]1-[#7:10]-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:5](:[c:6])-[C:4]-[C:3]-1 | 54 | [{"value": 54.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Concentrated H2SO4 (1.1 mL) was added slowly to sodium azide (2.49 g, 38.3 mmol) in water (2.7 mL) and chloroform (15 mL) keeping the temperature between 0-5° C. After 10 min the cold bath was removed and the reaction was stirred for 3 h at rt. Na2SO4 was added to the solution to dry it and the resulting chloroform sol... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary amide | c1ccc2c(c1)CCC21CC[NH]CC1 | c1ccc2c(c1)NCCC21CC[NH]CC1 | c1ccc2c(c1)NCCC21CC[NH]CC1 | Other | C(Cl)(Cl)Cl.O | null | 3 | O=C1CC2(CCN(C(=O)C(F)(F)F)CC2)c2ccccc21>C(Cl)(Cl)Cl.O>O=C1CC2(CCN(C(=O)C(F)(F)F)CC2)c2ccccc2N1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-d600e7c22e20492bb1c7c43362c150ef | CC(C)(C)C(=O)Cl.O=C1CC2(CCN(C(=O)C(F)(F)F)CC2)c2ccccc2N1>>CC(C)(C)C(=O)N1CCC2(CC1)CC(=O)Nc1ccccc12 | [OH-].[K+].FC(C(=O)N1CCC2(CC(NC3=CC=CC=C23)=O)CC1)(F)F.C(C)N(CC)CC.C(C(C)(C)C)(=O)Cl.Cl>>C(C(C)(C)C)(=O)N1CCC2(CC(NC3=CC=CC=C23)=O)CC1 | O=C(Cl)C([CH3:1])([CH3:3])[CH3:4].F[C:2](F)(F)[C:5](=[O:6])[N:7]1[CH2:8][CH2:9][C:10]2([CH2:11][CH2:12]1)[CH2:13][C:14](=[O:15])[NH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][c:22]12>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[N:7]1[CH2:8][CH2:9][C:10]2([CH2:11][CH2:12]1)[CH2:13][C:14](=[O:15])[NH:16][c:17]1[cH:18][cH:19]... | CC(C)(C)C(=O)Cl.O=C1CC2(CCN(C(=O)C(F)(F)F)CC2)c2ccccc2N1 | CC(C)(C)C(=O)N1CCC2(CC1)CC(=O)Nc1ccccc12 | null | null | CO.O | C-C Coupling | OtherReaction | 7544728283e40ff0668c879e468f3a8fb999de5381397811c654130f238b4867 | 193345062f11ce20dc65fa356750e49e1e2fd06b2ded8b26dbeef48f87207f49 | O=C1CC2(CCNCC2)c2ccccc2N1 | Cl-C(=O)-C(-[CH3;D1;+0:1])(-[CH3;D1;+0:2])-[CH3;D1;+0:3].F-[C;H0;D4;+0:4](-F)(-F)-[C:5](=[O;D1;H0:6])-[#7:7](-[C:8])-[C:9]>>[C:8]-[#7:7](-[C:5](=[O;D1;H0:6])-[C;H0;D4;+0:4](-[CH3;D1;+0:1])(-[CH3;D1;+0:2])-[CH3;D1;+0:3])-[C:9] | 79.7 | [{"value": 79.0, "product": "C(C(C)(C)C)(=O)N1CCC2(CC(NC3=CC=CC=C23)=O)CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.7, "product": "C(C(C)(C)C)(=O)N1CCC2(CC(NC3=CC=CC=C23)=O)CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | KOH (0.65 g, 11.5 mmol) in water (3.0 mL) was added to 19b (1.20 g, 3.8 mmol) in methanol (15 mL) and stirred at rt overnight. The reaction was neutralized with conc. HCl (1 mL) and then concentrated. The crude reaction mixture was evaporated from toluene to remove water. The crude amine was taken up in dichloromethane... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Trifluoro group | null | null | null | c1ccc2c(c1)NCCC21CC[NH]CC1 | Other | CO.O | null | 8 | CC(C)(C)C(=O)Cl.O=C1CC2(CCN(C(=O)C(F)(F)F)CC2)c2ccccc2N1>CO.O>CC(C)(C)C(=O)N1CCC2(CC1)CC(=O)Nc1ccccc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-54295f7da89143368c391cc8da153b10 | CC(C)(C)C(=O)Cl.CCOC(=O)C1CCNCC1>>CCOC(=O)C1CCN(C(=O)C(C)(C)C)CC1 | N1CCC(C(=O)OCC)CC1.C(C)N(CC)CC.CC(C(=O)Cl)(C)C>>C(C(C)(C)C)(=O)N1CCC(CC1)C(=O)OCC | Cl[C:10](=[O:11])[C:12]([CH3:13])([CH3:14])[CH3:15].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][NH:9][CH2:16][CH2:17]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][N:9]([C:10](=[O:11])[C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:16][CH2:17]1 | CC(C)(C)C(=O)Cl.CCOC(=O)C1CCNCC1 | CCOC(=O)C1CCN(C(=O)C(C)(C)C)CC1 | null | null | ClCCl | Acylation | N-alkylation of secondary amines with alkyl halides | aaa7c80569e6aa145ac8d7318e06893ee71aff0c965e85eca836522c948938d5 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | C1CCNCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[C;D1;H3:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[C;D1;H3:6])-[C:10]-[C:11] | 94 | [{"value": 94.0, "product": "C(C(C)(C)C)(=O)N1CCC(CC1)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.0, "product": "C(C(C)(C)C)(=O)N1CCC(CC1)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 16 | HOUR | Ethyl isonipecotate (20 mL, 130 mmol) was dissolved in 130 mL of dichloromethane and cooled to 0° C. and triethyl amine (19.9 mL, 143 mmol) was added. Trimethylacetyl chloride (16.8 mL, 136 mmol) was added dropwise and the reaction was allowed to warm to rt and stirred for 16 h. The reaction mixture was washed with hyd... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1 | HCl | ClCCl | 0 | 16 | CC(C)(C)C(=O)Cl.CCOC(=O)C1CCNCC1>ClCCl>CCOC(=O)C1CCN(C(=O)C(C)(C)C)CC1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-cc3d8336b3cb4a12933dd1ca2bc5b351 | CCOC(=O)C1CCN(C(=O)C(C)(C)C)CC1>>CC(C)(C)CN1CCC(CO)CC1 | C(C(C)(C)C)(=O)N1CCC(CC1)C(=O)OCC.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>C(C(C)(C)C)N1CCC(CC1)CO | CCO[C:10]([CH:9]1[CH2:8][CH2:7][N:6]([C:5](=O)[C:2]([CH3:1])([CH3:3])[CH3:4])[CH2:13][CH2:12]1)=[O:11]>>[CH3:1][C:2]([CH3:3])([CH3:4])[CH2:5][N:6]1[CH2:7][CH2:8][CH:9]([CH2:10][OH:11])[CH2:12][CH2:13]1 | CCOC(=O)C1CCN(C(=O)C(C)(C)C)CC1 | CC(C)(C)CN1CCC(CO)CC1 | null | null | O1CCCC1 | Reduction | OtherReaction | c69e55c870fca7a48716cf1a13d3b1c66b1429a862fb2c663e47b4c648179c46 | a65143cb02ef97811e30a8153880ab0c649a356c31e2df2bd3a78b2a9b48cbfc | C1CCNCC1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]1-[C:4]-[C:5]-[#7:6](-[C;H0;D3;+0:7](=O)-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11])-[C:12]-[C:13]-1>>[C;D1;H3:9]-[C:8](-[C;D1;H3:10])(-[C;D1;H3:11])-[CH2;D2;+0:7]-[#7:6]1-[C:5]-[C:4]-[C:3](-[CH2;D2;+0:1]-[OH;D1;+0:2])-[C:13]-[C:12]-1 | 97 | [{"value": 97.0, "product": "C(C(C)(C)C)N1CCC(CC1)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.5, "product": "C(C(C)(C)C)N1CCC(CC1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 24 | HOUR | 20a (29.5 g, 122 mmol) was dissolved in 200 mL of tetrahydrofuran and cooled to 0° C. Lithium aluminum hydride (s) (10.6 g, 279 mmol) was added slowly and the reaction was allowed to warm to rt and stirred for 24 h. The reaction was quenched by slow addition of sodium sulfate hydrated crystals (Na2SO4.10H2O) until ther... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Tertiary amide | Primary alcohol | null | null | C1CC[NH]CC1 | Other | O1CCCC1 | 0 | 24 | CCOC(=O)C1CCN(C(=O)C(C)(C)C)CC1>O1CCCC1>CC(C)(C)CN1CCC(CO)CC1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-68635d8bc43641c59b183e28455d7656 | CC(C)(C)CN1CCC(CO)CC1>>CC(C)(C)CN1CCC(C=O)CC1 | C(C(C)(C)C)N1CCC(CC1)CO.C(C(=O)Cl)(=O)Cl.CS(=O)C>>C(C(C)(C)C)N1CCC(CC1)C=O | [CH3:1][C:2]([CH3:3])([CH3:4])[CH2:5][N:6]1[CH2:7][CH2:8][CH:9]([CH2:10][OH:11])[CH2:12][CH2:13]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[CH2:5][N:6]1[CH2:7][CH2:8][CH:9]([CH:10]=[O:11])[CH2:12][CH2:13]1 | CC(C)(C)CN1CCC(CO)CC1 | CC(C)(C)CN1CCC(C=O)CC1 | null | null | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | C1CCNCC1 | [C:1]-[C:2](-[CH2;D2;+0:3]-[OH;D1;+0:4])-[C:5]>>[C:1]-[C:2](-[CH;D2;+0:3]=[O;H0;D1;+0:4])-[C:5] | 85.7 | [{"value": 85.7, "product": "C(C(C)(C)C)N1CCC(CC1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 30 | MINUTE | To a solution of oxalyl chloride (490 μL, 5.6 mmol) in DCM (10 mL) at −78° C. was added DMSO (796 μL, 11.2 mmol) dropwise followed by the addition of a solution of 20b (943 mg, 5.6 mmol) in DCM (2 mL). The mixture was stirred at −78° C. for 30 min and TEA (3.6 mL, 25.5 mmol) was added. The reaction was stirred at −78° ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | C1CC[NH]CC1 | null | C(Cl)Cl | -78 | 0.5 | CC(C)(C)CN1CCC(CO)CC1>C(Cl)Cl>CC(C)(C)CN1CCC(C=O)CC1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-9c1f04891eae4e6f995f2661eafdbac1 | CC(C)(C)CN1CCC2(CC1)CN(c1ccccc1N)c1ccccc12.O=C(N=C=S)c1ccccc1>>CC(C)(C)CN1CCC2(CC1)CN(c1ccccc1NC(=S)NC(=O)c1ccccc1)c1ccccc12 | C(C(C)(C)C)N1CCC2(CC1)CN(C1=CC=CC=C12)C1=C(N)C=CC=C1.C(C1=CC=CC=C1)(=O)N=C=S>>C(C(C)(C)C)N1CCC2(CC1)CN(C1=CC=CC=C12)C1=C(C=CC=C1)NC(=S)NC(C1=CC=CC=C1)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[CH2:5][N:6]1[CH2:7][CH2:8][C:9]2([CH2:10][CH2:11]1)[CH2:12][N:13]([c:14]1[cH:15][cH:16][cH:17][cH:18][c:19]1[NH2:20])[c:32]1[cH:33][cH:34][cH:35][cH:36][c:37]12.[C:21](=[S:22])=[N:23][C:24](=[O:25])[c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[CH2:5][N:6]1[CH... | CC(C)(C)CN1CCC2(CC1)CN(c1ccccc1N)c1ccccc12.O=C(N=C=S)c1ccccc1 | CC(C)(C)CN1CCC2(CC1)CN(c1ccccc1NC(=S)NC(=O)c1ccccc1)c1ccccc12 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | thiourea | 9037f368cdf8e91fcd9f93f4d9cf27991f85fa921c9d19c7875d3a77561f439b | 0fbf3d6c8cd704ac451c2cf111f32090de5e76a9d41cce326e212c758f4ed46f | O=C(NC(=S)Nc1ccccc1N1CC2(CCNCC2)c2ccccc21)c1ccccc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6](-[c:7])-[N;H0;D2;+0:8]=[C;H0;D2;+0:9]=[S;D1;H0:10]>>[O;D1;H0:5]=[C:6](-[c:7])-[NH;D2;+0:8]-[C;H0;D3;+0:9](=[S;D1;H0:10])-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 3 | HOUR | A mixture of 20f (118 mg, 0.33 mmol) and benzoylisothiocyanate (63 μL, 0.47 mmol) in DCM (3 mL) was stirred at rt for 3 h. The reaction was concentrated and the residue was purified by flash chromatography (silica gel, 0-10% MeOH/DCM) to give 20 g, as yellow solid (156 mg). LC-MS m/z 513.06 [M+H]+.
Conditions: See reac... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Isothiocyanate | Thiourea | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)[NH]CC21CC[NH]CC1 | null | C(Cl)Cl | null | 3 | CC(C)(C)CN1CCC2(CC1)CN(c1ccccc1N)c1ccccc12.O=C(N=C=S)c1ccccc1>C(Cl)Cl>CC(C)(C)CN1CCC2(CC1)CN(c1ccccc1NC(=S)NC(=O)c1ccccc1)c1ccccc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-1f2d8b6dfd7647258a6c9672414d151f | CC(C)(C)OC(=O)NCCBr.Oc1ccc(F)cc1>>CC(C)(C)OC(=O)NCCOc1ccc(F)cc1 | BrCCNC(OC(C)(C)C)=O.FC1=CC=C(C=C1)O.C([O-])([O-])=O.[K+].[K+]>>FC1=CC=C(OCCNC(OC(C)(C)C)=O)C=C1 | Br[CH2:10][CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[OH:11][c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1 | CC(C)(C)OC(=O)NCCBr.Oc1ccc(F)cc1 | CC(C)(C)OC(=O)NCCOc1ccc(F)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[#7:3]-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C;D1;H3:10].[OH;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[C;D1;H3:8]-[C:7](-[C;D1;H3:9])(-[C;D1;H3:10])-[#8:6]-[C:4](=[O;D1;H0:5])-[#7:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:11]-[c:12](:[c:13]):[c:14] | null | [] | 90 | CELSIUS | 8 | HOUR | To the crude product (700 mg) of t-butyl 2-bromoethylcarbamate obtained in Step 1 were added 4-fluorophenol (875 mg), potassium carbonate (1.08 g) and DMF (7 ml), and the mixture was stirred overnight at 90° C. The solvent was evaporated, and the mixture was diluted with ethyl acetate. After washing with water, the org... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | CN(C)C=O | 90 | 8 | CC(C)(C)OC(=O)NCCBr.Oc1ccc(F)cc1>CN(C)C=O>CC(C)(C)OC(=O)NCCOc1ccc(F)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-62c17d1cfb3e4e06b586c994edd4847a | CC(C)(C)OC(=O)N[C@@H](COCc1ccccc1)C(=O)O>>CC(C)(C)OC(=O)N[C@H](CO)COCc1ccccc1 | C(C1=CC=CC=C1)OC[C@H](NC(=O)OC(C)(C)C)C(=O)O.C(C)N(CC)CC.ClC(=O)OCC>>C(C1=CC=CC=C1)OC[C@@H](CO)NC(OC(C)(C)C)=O | O=[C:10]([C@@H:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:12][O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[OH:11]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]([CH2:10][OH:11])[CH2:12][O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | CC(C)(C)OC(=O)N[C@@H](COCc1ccccc1)C(=O)O | CC(C)(C)OC(=O)N[C@H](CO)COCc1ccccc1 | null | null | O1CCCC1 | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | c1ccccc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[C:3](-[C:4])-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12]>>[C:4]-[C:3](-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[CH2;D2;+0:1]-[O;D1;H1:2] | 89.2 | [{"value": 89.2, "product": "C(C1=CC=CC=C1)OC[C@@H](CO)NC(OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | O-benzyl-N-(t-butoxycarbonyl)-L-serine (2 g) was dissolved in tetrahydrofuran (20 ml), triethylamine (1.22 ml) was added, and ethyl chloroformate (713 μl) was further added dropwise at 0° C. After stirring the reaction mixture at room temperature for 30 min, the reaction mixture was filtered, and one piece of ice was a... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccccc1 | Other | O1CCCC1 | null | 0.5 | CC(C)(C)OC(=O)N[C@@H](COCc1ccccc1)C(=O)O>O1CCCC1>CC(C)(C)OC(=O)N[C@H](CO)COCc1ccccc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-a762014a54fb470d8dbdaa3e765d6a38 | CC(C)(C)OC(=O)N[C@H](CO)COCc1ccccc1.Cc1cccc(O)c1>>Cc1cccc(OC[C@H](COCc2ccccc2)NC(=O)OC(C)(C)C)c1 | [Cl-].[Li+].C([O-])([O-])=O.[K+].[K+].C1=C(C=CC=C1O)C.C(C1=CC=CC=C1)OC[C@@H](CO)NC(OC(C)(C)C)=O.CS(=O)(=O)Cl>>C(C1=CC=CC=C1)OC[C@@H](COC1=CC(=CC=C1)C)NC(OC(C)(C)C)=O | [OH:7][CH2:8][C@H:9]([CH2:10][O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[NH:19][C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26].O[c:6]1[cH:5][cH:4][cH:3][c:2]([CH3:1])[cH:27]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([O:7][CH2:8][C@H:9]([CH2:10][O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]... | CC(C)(C)OC(=O)N[C@H](CO)COCc1ccccc1.Cc1cccc(O)c1 | Cc1cccc(OC[C@H](COCc2ccccc2)NC(=O)OC(C)(C)C)c1 | null | null | ClCCl.C(C)(=O)OCC.CN(C=O)C.C(C)N(CC)CC | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 8915084acbaaf997bf0f89ff5187cb2f89c25dc683fffc57b3391298c8430dd9 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc(COCCCOc2ccccc2)cc1 | O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | 0 | CELSIUS | 3 | HOUR | To t-butyl (1R)-2-(benzyloxy)-1-(hydroxymethyl)ethylcarbamate (3.23 g) obtained in Step 1 were added dichloromethane (40 ml), methanesulfonyl chloride (1.07 ml) and triethylamine (3.20 ml), and the mixture was stirred at 0° C. for 3 hrs. The reaction mixture was diluted with dichloromethane and, after washing with wate... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | ClCCl.C(C)(=O)OCC.CN(C=O)C.C(C)N(CC)CC | 0 | 3 | CC(C)(C)OC(=O)N[C@H](CO)COCc1ccccc1.Cc1cccc(O)c1>ClCCl.C(C)(=O)OCC.CN(C=O)C.C(C)N(CC)CC>Cc1cccc(OC[C@H](COCc2ccccc2)NC(=O)OC(C)(C)C)c1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-090ebc008d494b28bcd771d148fefc56 | CC#N.CC(=O)O.NC(=O)CC(NC(=O)OCc1ccccc1)C(=O)O>>CC(C)(C)OC(=O)NCC(NC(=O)OCc1ccccc1)C(=O)O | C(C1=CC=CC=C1)OC(=O)NC(CC(N)=O)C(=O)O.C(C)(=O)OCC.C(C)#N.C(C)(=O)O.C(C)(=O)O.I(=O)C1=CC=CC=C1>>C(C1=CC=CC=C1)OC(=O)NC(C(=O)O)CNC(=O)OC(C)(C)C | N#C[CH3:3].O=[C:2]([CH3:1])[OH:5].[C:6](=[O:7])([NH2:8])[CH2:9][CH:10]([NH:11][C:12](=[O:13])[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[C:22](=[O:23])[OH:24]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH:10]([NH:11][C:12](=[O:13])[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:2... | CC#N.CC(=O)O.NC(=O)CC(NC(=O)OCc1ccccc1)C(=O)O | CC(C)(C)OC(=O)NCC(NC(=O)OCc1ccccc1)C(=O)O | null | null | O | C-C Coupling | OtherReaction | d2fbdfe5c7a8189bed535da320f733af8ea5493155b0efff3e22160d31f0e0a8 | be1dc69526379d85f6ae2bfb152a1f5c5cf3651fcc078deb0d696e723df75c33 | c1ccccc1 | N#C-[CH3;D1;+0:1].O=[C;H0;D3;+0:2](-[C;D1;H3:3])-[OH;D1;+0:4].[NH2;D1;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[CH2;D2;+0:8]-[C:9](-[#7:10]-[C:11]=[O;D1;H0:12])-[C:13](=[O;D1;H0:14])-[O;D1;H1:15]>>[C;D1;H3:3]-[C;H0;D4;+0:2](-[C;D1;H3:16])(-[CH3;D1;+0:1])-[O;H0;D2;+0:4]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[NH;D2;+0:5]-[CH2;D2;+0:8]-... | null | [] | null | null | 8 | HOUR | To N-(benzyloxycarbonyl)-DL-asparagine (7.5 g) were added ethyl acetate (36 ml), acetonitrile (36 ml), water (18 ml) and iodosobenzene diacetate (10 g), and the mixture was stirred overnight at room temperature. The reaction mixture was filtered and, after washing the obtained solid with ethyl acetate, dioxane (180 ml)... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitrile.Primary amide | Carbamic ester.Ether.Boc | null | null | c1ccccc1 | Other | O | null | 8 | CC#N.CC(=O)O.NC(=O)CC(NC(=O)OCc1ccccc1)C(=O)O>O>CC(C)(C)OC(=O)NCC(NC(=O)OCc1ccccc1)C(=O)O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-0ad54d77cb704d8991ae751edab467d2 | Cc1cccc(OCC(CNC(=O)OC(C)(C)C)NC(=O)OCc2ccccc2)c1>>Cc1cccc(OCC(CNC(=O)c2ccccc2)NC(=O)OCc2ccccc2)c1 | C(C)(C)(C)OC(NCC(COC=1C=C(C=CC1)C)NC(=O)OCC1=CC=CC=C1)=O.Cl>>C(C1=CC=CC=C1)OC(NC(COC=1C=C(C=CC1)C)CNC(C1=CC=CC=C1)=O)=O | O([C:12]([NH:11][CH2:10][CH:9]([CH2:8][O:7][c:6]1[cH:5][cH:4][cH:3][c:2]([CH3:1])[cH:31]1)[NH:20][C:21](=[O:22])[O:23][CH2:24][c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1)=[O:13])[C:19]([CH3:14])([CH3:15])[CH3:18]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([O:7][CH2:8][CH:9]([CH2:10][NH:11][C:12](=[O:13])[c:14]2[cH:15][cH:16... | Cc1cccc(OCC(CNC(=O)OC(C)(C)C)NC(=O)OCc2ccccc2)c1 | Cc1cccc(OCC(CNC(=O)c2ccccc2)NC(=O)OCc2ccccc2)c1 | null | null | O1CCOCC1 | C-C Coupling | OtherReaction | 4b5454ff55732467243b04a2a0a17ba187c44b263056056538e85c83ba9d735c | d315c27915b1f87320d7c4a24cfe2edb6800d69ebd2822741143e533c39656ee | O=C(NC(CNC(=O)c1ccccc1)COc1ccccc1)OCc1ccccc1 | [C:1]-[#7:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-O-[C;H0;D4;+0:5](-[CH3;D1;+0:6])(-[CH3;D1;+0:7])-[CH3;D1;+0:8]>>[C:1]-[#7:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[c;H0;D3;+0:6]1:[cH;D2;+0:7]:[c:9]:[c:10]:[cH;D2;+0:8]:[cH;D2;+0:5]:1 | 180.1 | [{"value": 180.1, "product": "C(C1=CC=CC=C1)OC(NC(COC=1C=C(C=CC1)C)CNC(C1=CC=CC=C1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To (2-benzyloxycarbonylamino-3-m-tolyloxypropyl)carbamic acid tert-butyl ester (220 mg) obtained in Step 2 was added 4N solution (2 ml) of hydrogen chloride in dioxane, and the mixture was stirred at room temperature for 1 hr. The solvent was evaporated, dichloromethane (7 ml), benzoyl chloride (96 μl) and triethylamin... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amide | null | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | O1CCOCC1 | null | 1 | Cc1cccc(OCC(CNC(=O)OC(C)(C)C)NC(=O)OCc2ccccc2)c1>O1CCOCC1>Cc1cccc(OCC(CNC(=O)c2ccccc2)NC(=O)OCc2ccccc2)c1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-6f5c4f28190c47c0b1aa9429d8e223c6 | CS(=O)(=O)Cl.C[C@@H](CO)NC(=O)OC(C)(C)C>>C[C@@H](COS(C)(=O)=O)NC(=O)OC(C)(C)C | OC[C@H](C)NC(OC(C)(C)C)=O.CS(=O)(=O)Cl.C(C)N(CC)CC>>CS(=O)(=O)OC[C@H](C)NC(=O)OC(C)(C)C | Cl[S:5]([CH3:6])(=[O:7])=[O:8].[CH3:1][C@@H:2]([CH2:3][OH:4])[NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16]>>[CH3:1][C@@H:2]([CH2:3][O:4][S:5]([CH3:6])(=[O:7])=[O:8])[NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16] | CS(=O)(=O)Cl.C[C@@H](CO)NC(=O)OC(C)(C)C | C[C@@H](COS(C)(=O)=O)NC(=O)OC(C)(C)C | null | null | ClCCl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | null | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | null | [] | 0 | CELSIUS | 2 | HOUR | To the compound (5.9 g) obtained in Step 1 were added methanesulfonyl chloride (3.1 ml), triethylamine (9.0 ml) and dichloromethane (150 ml), and the mixture was stirred at 0° C. for 2 hrs. The mixture was diluted with dichloromethane and, after washing with water, the organic layer was dried over anhydrous magnesium s... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | null | HCl | ClCCl | 0 | 2 | CS(=O)(=O)Cl.C[C@@H](CO)NC(=O)OC(C)(C)C>ClCCl>C[C@@H](COS(C)(=O)=O)NC(=O)OC(C)(C)C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-b140c6747a1a44558eefb386d2991521 | C[C@@H](CCl)NC(=O)OC(C)(C)C.Oc1cccc(F)c1>>C[C@@H](COc1cccc(F)c1)NC(=O)OC(C)(C)C | ClC[C@H](C)NC(OC(C)(C)C)=O.FC=1C=C(C=CC1)O.C([O-])([O-])=O.[K+].[K+].CN(C)C=O>>FC=1C=C(OC[C@H](C)NC(OC(C)(C)C)=O)C=CC1 | Cl[CH2:3][C@H:2]([CH3:1])[NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19].[OH:4][c:5]1[cH:6][cH:7][cH:8][c:9]([F:10])[cH:11]1>>[CH3:1][C@@H:2]([CH2:3][O:4][c:5]1[cH:6][cH:7][cH:8][c:9]([F:10])[cH:11]1)[NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19] | C[C@@H](CCl)NC(=O)OC(C)(C)C.Oc1cccc(F)c1 | C[C@@H](COc1cccc(F)c1)NC(=O)OC(C)(C)C | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])-[#7:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11].[OH;D1;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H3:9]-[C:8](-[C;D1;H3:10])(-[C;D1;H3:11])-[#8:7]-[C:5](=[O;D1;H0:6])-[#7:4]-[C:2](-[C;D1;H3:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:12]-[c:13](:[c:14]):[c:15] | null | [] | 95 | CELSIUS | 8 | HOUR | To the compound (500 mg) obtained in Step 3 were added 3-fluorophenol (84 μl), potassium carbonate (250 mg) and DMF (2 ml), and the mixture was stirred overnight at 95° C. The reaction mixture was diluted with ethyl acetate. After washing with water, the organic layer was dried over anhydrous magnesium sulfate. The sol... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HCl | C(C)(=O)OCC | 95 | 8 | C[C@@H](CCl)NC(=O)OC(C)(C)C.Oc1cccc(F)c1>C(C)(=O)OCC>C[C@@H](COc1cccc(F)c1)NC(=O)OC(C)(C)C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-aba74c00bab547b9bde785f9f9547b37 | Nc1cccc2cnccc12.O=C(Cl)Oc1ccccc1>>O=C(Nc1cccc2cnccc12)Oc1ccccc1 | NC1=C2C=CN=CC2=CC=C1.ClC(=O)OC1=CC=CC=C1.N1=CC=CC=C1.O1CCCC1>>C1=NC=CC2=C(C=CC=C12)NC(OC1=CC=CC=C1)=O | [NH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]2[cH:9][n:10][cH:11][cH:12][c:13]12.Cl[C:2](=[O:1])[O:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][c:8]2[cH:9][n:10][cH:11][cH:12][c:13]12)[O:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | Nc1cccc2cnccc12.O=C(Cl)Oc1ccccc1 | O=C(Nc1cccc2cnccc12)Oc1ccccc1 | null | null | ClCCl | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | O=C(Nc1cccc2cnccc12)Oc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[#8:3]-[c:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | 3 | HOUR | To 5-aminoisoquinoline (2.7 g) were added phenyl chloroformate (2.85 ml), pyridine (2.0 ml) and tetrahydrofuran (50 ml), and the mixture was stirred for 3 hrs. The reaction mixture was diluted with dichloromethane, and washed with water and saturated aqueous sodium hydrogen carbonate. The organic layer was dried over a... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccc2cnccc2c1.c1ccccc1 | HCl | ClCCl | null | 3 | Nc1cccc2cnccc12.O=C(Cl)Oc1ccccc1>ClCCl>O=C(Nc1cccc2cnccc12)Oc1ccccc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-f15264134eac4f0192cdd015c4b915cf | Nc1cccc2ccc(O)cc12.O=C(Cl)Oc1ccccc1>>O=C(Nc1cccc2ccc(O)cc12)Oc1ccccc1 | NC=1C=CC=C2C=CC(=CC12)O.ClC(=O)OC1=CC=CC=C1.C(O)([O-])=O.[Na+].O>>OC1=CC=C2C=CC=C(C2=C1)NC(OC1=CC=CC=C1)=O | [NH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]2[cH:9][cH:10][c:11]([OH:12])[cH:13][c:14]12.Cl[C:2](=[O:1])[O:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][c:8]2[cH:9][cH:10][c:11]([OH:12])[cH:13][c:14]12)[O:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | Nc1cccc2ccc(O)cc12.O=C(Cl)Oc1ccccc1 | O=C(Nc1cccc2ccc(O)cc12)Oc1ccccc1 | null | null | ClCCl | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | O=C(Nc1cccc2ccccc12)Oc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[#8:3]-[c:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | 3 | HOUR | To 8-amino-2-naphthol (100 mg) were added phenyl chloroformate (87 μl), saturated aqueous sodium hydrogen carbonate (0.5 ml), dichloromethane (1 ml) and water (0.5 ml), and the mixture was stirred for 3 hrs. The reaction mixture was diluted with dichloromethane. After washing with 1N hydrochloric acid, the organic laye... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccc2ccccc2c1.c1ccccc1 | HCl | ClCCl | null | 3 | Nc1cccc2ccc(O)cc12.O=C(Cl)Oc1ccccc1>ClCCl>O=C(Nc1cccc2ccc(O)cc12)Oc1ccccc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-b75428cddf274b5f91f1a55d8afead7e | Cc1cccc(OC[C@H](COCc2ccccc2)NC(=O)OC(C)(C)C)c1>>Cc1cccc(OC[C@H](CO)NC(=O)OC(C)(C)C)c1 | C(C1=CC=CC=C1)OC[C@@H](COC1=CC(=CC=C1)C)NC(OC(C)(C)C)=O>>OC[C@@H](COC1=CC(=CC=C1)C)NC(OC(C)(C)C)=O | c1ccc(C[O:11][CH2:10][C@@H:9]([CH2:8][O:7][c:6]2[cH:5][cH:4][cH:3][c:2]([CH3:1])[cH:20]2)[NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])cc1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([O:7][CH2:8][C@H:9]([CH2:10][OH:11])[NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20]1 | Cc1cccc(OC[C@H](COCc2ccccc2)NC(=O)OC(C)(C)C)c1 | Cc1cccc(OC[C@H](CO)NC(=O)OC(C)(C)C)c1 | null | [C].[Pd] | C(C)O | Deprotection | Hydroxyl benzyl deprotection | c8a6fd2e05b2d36256c76b73aaf4118f20eb14abce1c0289b554265e30b218aa | 29a81fd08d26edc3da6d72c4958026f5af2119326dc1b4714ee5be1c41835609 | c1ccccc1 | [C:1]-[C:2]-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1>>[C:1]-[C:2]-[OH;D1;+0:3] | 104.2 | [{"value": 104.2, "product": "OC[C@@H](COC1=CC(=CC=C1)C)NC(OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | To t-butyl (1S)-2-(benzyloxy)-1-[(3-methylphenoxy)methyl]ethylcarbamate (3.8 g) obtained in Step 2 of Example 15 were added 10% palladium-carbon (wet, 1 g) and ethanol (30 ml), and the mixture was stirred for 2 days under hydrogen atmosphere. After celite filtration, the solvent was evaporated. The obtained crude produ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Primary alcohol | c1ccccc1 | null | c1ccccc1 | Other | [C].[Pd].C(C)O | null | 48 | Cc1cccc(OC[C@H](COCc2ccccc2)NC(=O)OC(C)(C)C)c1>[C].[Pd].C(C)O>Cc1cccc(OC[C@H](CO)NC(=O)OC(C)(C)C)c1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-4e5415304ca54750898b53f2b9270f2c | NC(=O)C[C@H](NC(=O)OCc1ccccc1)C(=O)O>>NC[C@H](NC(=O)OCc1ccccc1)C(=O)O | C(C1=CC=CC=C1)OC(=O)N[C@@H](CC(N)=O)C(=O)O.C(C)(=O)OCC.C(C)#N.C(C)(=O)O.C(C)(=O)O.I(=O)C1=CC=CC=C1>>NC[C@@H](C(=O)O)NC(=O)OCC1=CC=CC=C1 | O=C([NH2:1])[CH2:2][C@H:3]([NH:4][C:5](=[O:6])[O:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[C:15](=[O:16])[OH:17]>>[NH2:1][CH2:2][C@H:3]([NH:4][C:5](=[O:6])[O:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[C:15](=[O:16])[OH:17] | NC(=O)C[C@H](NC(=O)OCc1ccccc1)C(=O)O | NC[C@H](NC(=O)OCc1ccccc1)C(=O)O | null | null | O | Miscellaneous | OtherReaction | c5692c554f9343f8f76761083bca8bd4beba23dd611dd62c01371560c29278fc | 070e9d5c50f4bf21fc8869940b9d63896edd4a1db34c9e233190574d88bdcd64 | c1ccccc1 | O=C(-[NH2;D1;+0:1])-[CH2;D2;+0:2]-[C:3](-[#7:4]-[C:5]=[O;D1;H0:6])-[C:7](=[O;D1;H0:8])-[O;D1;H1:9]>>[NH2;D1;+0:1]-[CH2;D2;+0:2]-[C:3](-[#7:4]-[C:5]=[O;D1;H0:6])-[C:7](=[O;D1;H0:8])-[O;D1;H1:9] | null | [] | null | null | 8 | HOUR | To N-(benzyloxycarbonyl)-L-asparagine (7.5 g) were added ethyl acetate (36 ml), acetonitrile (36 ml), water (18 ml) and iodosobenzene diacetate (10 g), and the mixture was stirred overnight at room temperature. The reaction mixture was filtered, and the obtained solid was washed with ethyl acetate to give the title com... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide | Primary amine | null | null | c1ccccc1 | Other | O | null | 8 | NC(=O)C[C@H](NC(=O)OCc1ccccc1)C(=O)O>O>NC[C@H](NC(=O)OCc1ccccc1)C(=O)O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-8a8273912e574903ba20d785b22b3f70 | CO.NC[C@H](NC(=O)OCc1ccccc1)C(=O)O.O=S(Cl)Cl>>COC(=O)[C@H](CN)NC(=O)OCc1ccccc1.Cl | NC[C@@H](C(=O)O)NC(=O)OCC1=CC=CC=C1.S(=O)(Cl)Cl.CO>>Cl.NC[C@@H](C(=O)OC)NC(=O)OCC1=CC=CC=C1 | [CH3:1][OH:2].O[C:3](=[O:4])[C@H:5]([CH2:6][NH2:7])[NH:8][C:9](=[O:10])[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1.O=S(Cl)[Cl:19]>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][NH2:7])[NH:8][C:9](=[O:10])[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1.[ClH:19] | CO.NC[C@H](NC(=O)OCc1ccccc1)C(=O)O.O=S(Cl)Cl | COC(=O)[C@H](CN)NC(=O)OCc1ccccc1.Cl | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccccc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4](-[C:5])-[#7:6]-[C:7]=[O;D1;H0:8].[C;D1;H3:9]-[OH;D1;+0:10]>>[C:5]-[C:4](-[#7:6]-[C:7]=[O;D1;H0:8])-[C;H0;D3;+0:2](=[O;D1;H0:3])-[O;H0;D2;+0:10]-[C;D1;H3:9].[ClH;D0;+0:1] | null | [] | null | null | 8 | HOUR | To the compound obtained in Step 1 were added methanol (100 ml) and thionyl chloride (2.4 ml), and the mixture was stirred overnight at room temperature. The solvent was evaporated to give the title compound as a crude product.
Conditions: See reaction.notes.procedure_details.
Workup: The solvent was evaporated | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1 | HCl | null | null | 8 | CO.NC[C@H](NC(=O)OCc1ccccc1)C(=O)O.O=S(Cl)Cl>>COC(=O)[C@H](CN)NC(=O)OCc1ccccc1.Cl |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-b06412e6adab493bad4027094337a0c0 | CSC[C@@H](CO)NC(=O)OC(C)(C)C.Oc1cccc(F)c1>>CSC[C@@H](COc1cccc(F)c1)NC(=O)OC(C)(C)C | OC[C@H](CSC)NC(OC(C)(C)C)=O.C1=C(C=CC=C1O)C.FC=1C=C(C=CC1)O>>FC=1C=C(OC[C@H](CSC)NC(OC(C)(C)C)=O)C=CC1 | O[CH2:5][C@H:4]([CH2:3][S:2][CH3:1])[NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21].[OH:6][c:7]1[cH:8][cH:9][cH:10][c:11]([F:12])[cH:13]1>>[CH3:1][S:2][CH2:3][C@@H:4]([CH2:5][O:6][c:7]1[cH:8][cH:9][cH:10][c:11]([F:12])[cH:13]1)[NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21] | CSC[C@@H](CO)NC(=O)OC(C)(C)C.Oc1cccc(F)c1 | CSC[C@@H](COc1cccc(F)c1)NC(=O)OC(C)(C)C | null | null | null | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccccc1 | O-[CH2;D2;+0:1]-[C:2](-[C:3])-[#7:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11].[OH;D1;+0:12]-[c:13](:[c:14]):[c:15]>>[C:3]-[C:2](-[#7:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11])-[CH2;D2;+0:1]-[O;H0;D2;+0:12]-[c:13](:[c:14]):[c:15] | null | [] | null | null | null | null | By the operation similar to that in Step 2 of Example 15 except that t-butyl (1R)-2-hydroxy-1-[(methylsulfanyl)methyl]ethylcarbamate (1 g) obtained in Step 1 was used as a starting material and m-cresol was changed to 3-fluorophenol, the title compound (300 mg) was obtained.
Conditions: See reaction.notes.procedure_det... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccccc1 | HO- | null | null | null | CSC[C@@H](CO)NC(=O)OC(C)(C)C.Oc1cccc(F)c1>>CSC[C@@H](COc1cccc(F)c1)NC(=O)OC(C)(C)C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-5e9a210e943d4c09b800007a646d13db | NO.O=[N+]([O-])c1cccc2cnccc12>>Nc1ccc([N+](=O)[O-])c2ccncc12 | [N+](=O)([O-])C1=C2C=CN=CC2=CC=C1.Cl.NO.C(C)O.[OH-].[Na+]>>NC=1C=CC(=C2C=CN=CC12)[N+](=O)[O-] | O[NH2:1].[cH:2]1[cH:3][cH:4][c:5]([N+:6](=[O:7])[O-:8])[c:9]2[cH:10][cH:11][n:12][cH:13][c:14]12>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([N+:6](=[O:7])[O-:8])[c:9]2[cH:10][cH:11][n:12][cH:13][c:14]12 | NO.O=[N+]([O-])c1cccc2cnccc12 | Nc1ccc([N+](=O)[O-])c2ccncc12 | null | null | CO | Functional Group Addition | OtherReaction | d9ae69cf2d212f0240d3dd451674b2808f3b15aa965f875e5828bfdbb7e5662e | 5d27deb117d58af1451678366bb9ef32f3c0470c7072ee34ccab01a4e73c86c7 | c1ccc2cnccc2c1 | O-[NH2;D1;+0:1].[c:2]:[#7;a:3]:[c:4]:[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[NH2;D1;+0:1]-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:5](:[c:6]):[c:4]:[#7;a:3]:[c:2] | 57.5 | [{"value": 57.5, "product": "NC=1C=CC(=C2C=CN=CC12)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To 5-nitroisoquinoline (2.0 g) were added hydroxylamine hydrochloride (5.0 g) and ethanol (120 ml). A solution of sodium hydroxide (10 g) in methanol (65 ml) was slowly added at 50° C. over 90 min. The reaction mixture was poured into ice water (700 g) and the resulting precipitate was collected by filtration. The resi... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Primary amine | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | HO- | CO | null | null | NO.O=[N+]([O-])c1cccc2cnccc12>CO>Nc1ccc([N+](=O)[O-])c2ccncc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-dbe2310c979846949888823e57059fe4 | O=C(Nc1ccc([N+](=O)[O-])c2ccncc12)C(F)(F)F>>Nc1ccc(NC(=O)C(F)(F)F)c2cnccc12 | [N+](=O)([O-])C1=C2C=CN=CC2=C(C=C1)NC(C(F)(F)F)=O.C(C)(=O)OCC>>NC1=C2C=CN=CC2=C(C=C1)NC(C(F)(F)F)=O | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([NH:6][C:7](=[O:8])[C:9]([F:10])([F:11])[F:12])[c:13]2[cH:14][n:15][cH:16][cH:17][c:18]12>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([NH:6][C:7](=[O:8])[C:9]([F:10])([F:11])[F:12])[c:13]2[cH:14][n:15][cH:16][cH:17][c:18]12 | O=C(Nc1ccc([N+](=O)[O-])c2ccncc12)C(F)(F)F | Nc1ccc(NC(=O)C(F)(F)F)c2cnccc12 | null | [C].[Pd].[Pd] | O1CCCC1 | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2cnccc2c1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 1 | HOUR | To N-(5-nitroisoquinolin-8-yl)trifluoroacetamide (200 mg) were added ethyl acetate (15 ml) and 5% palladium-carbon (wet, 20 mg) and the mixture was stirred at room temperature under hydrogen atmosphere for 1 hr. Tetrahydrofuran was added to the reaction mixture to dissolve the resultant crystals, and palladium catalyst... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2cnccc2c1 | Other | [C].[Pd].[Pd].O1CCCC1 | null | 1 | O=C(Nc1ccc([N+](=O)[O-])c2ccncc12)C(F)(F)F>[C].[Pd].[Pd].O1CCCC1>Nc1ccc(NC(=O)C(F)(F)F)c2cnccc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-8e334d07d49a400c969557c248621aab | CC(N)COc1cc(F)cc(F)c1.CS(C)=O.O=C(Nc1ccc(NC(=O)C(F)(F)F)c2cnccc12)Oc1ccccc1>>CC(COc1cc(F)cc(F)c1)NC(=O)Nc1ccc(NC(=O)C(F)(F)F)c2cnccc12.O=C(O)C(F)(F)F.O=C(O)C(F)(F)F | C1(=CC=CC=C1)OC(NC1=C2C=CN=CC2=C(C=C1)NC(C(F)(F)F)=O)=O.Cl.FC=1C=C(OCC(C)N)C=C(C1)F.CS(=O)C.C(C)(C)N(C(C)C)CC>>FC(C(=O)O)(F)F.OC(=O)C(F)(F)F.FC=1C=C(OCC(C)NC(=O)NC2=C3C=CN=CC3=C(C=C2)NC(C(F)(F)F)=O)C=C(C1)F | [CH3:1][CH:2]([CH2:3][O:4][c:5]1[cH:6][c:7]([F:8])[cH:9][c:10]([F:11])[cH:12]1)[NH2:13].CS(=[O:34])[CH3:42].c1cc[cH:37][c:35]([O:36][C:14](=[O:15])[NH:16][c:17]2[cH:18][cH:19][c:20]([NH:21][C:22](=[O:23])[C:24]([F:25])([F:26])[F:27])[c:28]3[cH:29][n:30][cH:31][cH:32][c:33]23)c1>>[CH3:1][CH:2]([CH2:3][O:4][c:5]1[cH:6][c... | CC(N)COc1cc(F)cc(F)c1.CS(C)=O.O=C(Nc1ccc(NC(=O)C(F)(F)F)c2cnccc12)Oc1ccccc1 | CC(COc1cc(F)cc(F)c1)NC(=O)Nc1ccc(NC(=O)C(F)(F)F)c2cnccc12.O=C(O)C(F)(F)F.O=C(O)C(F)(F)F | null | null | C(C)(=O)OCC | Acylation | OtherReaction | f0c5fd69bef1664df04f66db78476e33415011efa6a7fa1a15c84a7c279befda | 5969a4d8500ea1bdd74a4c3791b80a2e4b283dacc7dc28a5e1048743398787de | O=C(NCCOc1ccccc1)Nc1cccc2cnccc12 | C-S(-[CH3;D1;+0:1])=[O;H0;D1;+0:2].[C:3]-[C:4](-[C;D1;H3:5])-[NH2;D1;+0:6].[O;D1;H0:7]=[C;H0;D3;+0:8](-[#7:9]-[c:10])-[O;H0;D2;+0:11]-[c;H0;D3;+0:12]1:[cH;D2;+0:13]:c:c:c:c:1>>[C:3]-[C:4](-[C;D1;H3:5])-[NH;D2;+0:6]-[C;H0;D3;+0:8](=[O;D1;H0:7])-[#7:9]-[c:10].[F;D1;H0:14]-[C;H0;D4;+0:13](-[F;D1;H0:15])(-[F;D1;H0:16])-[C;... | 0.1 | [{"value": 0.1, "product": "FC(C(=O)O)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To 8-(trifluoroacetylamino)isoquinolin-5-ylcarbamic acid phenyl ester (35 mg) were added 2-(3,5-difluorophenoxy)-1-methylethylamine hydrochloride (22 mg) obtained in Example 52 as a synthetic intermediate, dimethyl sulfoxide (1 ml) and N,N-diisopropylethylamine (81 μl), and the mixture was stirred at room temperature f... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Primary amine.Sulfoxide | Trifluoro group.Trifluoro group.Carboxylic acid.Carboxylic acid.Urea | c1ccccc1 | null | c1ccccc1.c1ccc2cnccc2c1 | null | C(C)(=O)OCC | null | 0.5 | CC(N)COc1cc(F)cc(F)c1.CS(C)=O.O=C(Nc1ccc(NC(=O)C(F)(F)F)c2cnccc12)Oc1ccccc1>C(C)(=O)OCC>CC(COc1cc(F)cc(F)c1)NC(=O)Nc1ccc(NC(=O)C(F)(F)F)c2cnccc12.O=C(O)C(F)(F)F.O=C(O)C(F)(F)F |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-f3dc3c9b14454ea5a9913cceb9841054 | Cc1cccc(OC[C@H](CO)NC(=O)OC(C)(C)C)c1.O=[N+]([O-])c1cccc(CBr)c1>>Cc1cccc(OC[C@H](COCc2cccc([N+](=O)[O-])c2)NC(=O)OC(C)(C)C)c1 | OC[C@@H](COC1=CC(=CC=C1)C)NC(OC(C)(C)C)=O.[N+](=O)([O-])C=1C=C(CBr)C=CC1.S(=O)(=O)([O-])[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(CCC)[N+](CCCC)(CCCC)CCCC.[OH-].[Na+]>>CC=1C=C(OC[C@H](COCC2=CC(=CC=C2)[N+](=O)[O-])NC(OC(C)(C)C)=O)C=CC1 | [CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([O:7][CH2:8][C@H:9]([CH2:10][OH:11])[NH:22][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[cH:30]1.Br[CH2:12][c:13]1[cH:14][cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:21]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([O:7][CH2:8][C@H:9]([CH2:10][O:11][CH2:12][c:13]2[cH:14][cH... | Cc1cccc(OC[C@H](CO)NC(=O)OC(C)(C)C)c1.O=[N+]([O-])c1cccc(CBr)c1 | Cc1cccc(OC[C@H](COCc2cccc([N+](=O)[O-])c2)NC(=O)OC(C)(C)C)c1 | null | null | C(C)(=O)OCC.C1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | c1ccc(COCCCOc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 76.6 | [{"value": 76.6, "product": "CC=1C=C(OC[C@H](COCC2=CC(=CC=C2)[N+](=O)[O-])NC(OC(C)(C)C)=O)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | To t-butyl (1S)-2-hydroxy-1-[(3-methylphenoxy)methyl]ethylcarbamate (300 mg) obtained in Step 1 of Example 118 were added 3-nitrobenzyl bromide (254 mg), tetrabutylammonium sulfate (91 mg), benzene (2.3 ml) and 50% aqueous sodium hydroxide solution (2.3 ml), and the mixture was stirred at room temperature for 1.5 hrs. ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HBr | C(C)(=O)OCC.C1=CC=CC=C1 | null | 1.5 | Cc1cccc(OC[C@H](CO)NC(=O)OC(C)(C)C)c1.O=[N+]([O-])c1cccc(CBr)c1>C(C)(=O)OCC.C1=CC=CC=C1>Cc1cccc(OC[C@H](COCc2cccc([N+](=O)[O-])c2)NC(=O)OC(C)(C)C)c1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-3d3cb8533ec6479193672c26c1ce3bd8 | Cc1cccc(OCC(CNc2ccccc2[N+](=O)[O-])NC(=O)OCc2ccccc2)c1>>Cc1cccc(OCC(N)CNc2ccccc2[N+](=O)[O-])c1 | CC=1C=C(OCC(CNC2=C(C=CC=C2)[N+](=O)[O-])NC(OCC2=CC=CC=C2)=O)C=CC1.Br.C(C)(=O)O>>Br.CC=1C=C(OCC(CNC2=C(C=CC=C2)[N+](=O)[O-])N)C=CC1 | O=C(OCc1ccccc1)[NH:11][CH:10]([CH2:9][O:8][c:7]1[cH:6][cH:5][cH:4][c:3]([CH3:2])[cH:23]1)[CH2:12][NH:13][c:14]1[cH:15][cH:16][cH:17][cH:18][c:19]1[N+:20](=[O:21])[O-:22]>>[CH3:2][c:3]1[cH:4][cH:5][cH:6][c:7]([O:8][CH2:9][CH:10]([NH2:11])[CH2:12][NH:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[N+:20](=[O:21])[O-:22])[c... | Cc1cccc(OCC(CNc2ccccc2[N+](=O)[O-])NC(=O)OCc2ccccc2)c1 | Cc1cccc(OCC(N)CNc2ccccc2[N+](=O)[O-])c1 | null | null | ClCCl | Reduction | Hydrogenolysis of amides/imides/carbamates | 087b6600ba91d3df931fe6979f2445c192cbfd59e04fd2d8a10f7c7573ac669f | 4e549866ec1acadec4c84aaf8495992a28ec78d8ea5ef1b9f44dd843b0dcb7d4 | c1ccc(NCCCOc2ccccc2)cc1 | O=C(-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[C:4])-[NH2;D1;+0:1] | null | [] | 0 | CELSIUS | 2 | HOUR | To the compound obtained in Step 2 were added 30% hydrobromide/acetic acid (1 ml) and dichloromethane (2 ml), and the mixture was stirred at 0° C. for 2 hrs. The mixture was diluted with dichloromethane, and washed with saturated aqueous sodium hydrogen carbonate. The organic layer was dried over anhydrous sodium sulfa... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | c1ccccc1 | null | c1ccccc1.c1ccccc1 | HO- | ClCCl | 0 | 2 | Cc1cccc(OCC(CNc2ccccc2[N+](=O)[O-])NC(=O)OCc2ccccc2)c1>ClCCl>Cc1cccc(OCC(N)CNc2ccccc2[N+](=O)[O-])c1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-d2d1e0576b6c46f9ab8141cfe892bc38 | Cc1cccc(OC[C@H](CNc2ccccc2N)NC(=O)OC(C)(C)C)c1>>Cc1cccc(OC[C@H](Cn2cnc3ccccc32)NC(=O)OC(C)(C)C)c1 | NC1=C(NC[C@@H](COC2=CC(=CC=C2)C)NC(OC(C)(C)C)=O)C=CC=C1.C(C)(=O)O>>N1(C=NC2=C1C=CC=C2)C[C@@H](COC2=CC(=CC=C2)C)NC(OC(C)(C)C)=O | [CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([O:7][CH2:8][C@H:9]([CH2:10][NH:11][c:19]2[c:14]([NH2:13])[cH:15][cH:16][cH:17][cH:18]2)[NH:20][C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[cH:28]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([O:7][CH2:8][C@H:9]([CH2:10][n:11]2[cH:12][n:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c... | Cc1cccc(OC[C@H](CNc2ccccc2N)NC(=O)OC(C)(C)C)c1 | Cc1cccc(OC[C@H](Cn2cnc3ccccc32)NC(=O)OC(C)(C)C)c1 | null | null | C(C)(=O)OCC | Aromatic Heterocycle Formation | OtherReaction | 893e19ebbce3b7948c8870f51ab374cb3179603c120c41fdbe3090f30f6804c4 | c12bf4e666f812d0e692aca3756678364265d1c8b3469e9563c84f9ed1df94d2 | c1ccc(OCCCn2cnc3ccccc32)cc1 | [C:1]-[C:2]-[NH;D2;+0:3]-[c:4](:[c:5]):[c:6](-[NH2;D1;+0:7]):[c:8]>>[C:1]-[C:2]-[n;H0;D3;+0:3]1:[c:9]:[n;H0;D2;+0:7]:[c:6](:[c:8]):[c:4]:1:[c:5] | null | [] | 60 | CELSIUS | 1 | HOUR | To the compound (85 mg) obtained in Step 2 were added methyl orthformate (1 ml) and acetic acid (50 μl), and the mixture was stirred at 60° C. for 1 hr. The mixture was diluted with ethyl acetate, and washed with 1N sodium hydroxide. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evap... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine | null | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccccc1.c1ccc2[nH]cnc2c1 | Other | C(C)(=O)OCC | 60 | 1 | Cc1cccc(OC[C@H](CNc2ccccc2N)NC(=O)OC(C)(C)C)c1>C(C)(=O)OCC>Cc1cccc(OC[C@H](Cn2cnc3ccccc32)NC(=O)OC(C)(C)C)c1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-85ad0931441546fdb77303f6acdb74a0 | N[C@@H](CCO)C(=O)O.O=C(Cl)OCc1ccccc1>>O=C(N[C@H]1CCOC1=O)OCc1ccccc1 | ClC(=O)OCC1=CC=CC=C1.N[C@@H](CCO)C(=O)O.C(O)([O-])=O.[Na+].O>>O=C1OCC[C@@H]1NC(OCC1=CC=CC=C1)=O | O[C:8]([C@@H:4]([NH2:3])[CH2:5][CH2:6][OH:7])=[O:9].Cl[C:2](=[O:1])[O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[O:1]=[C:2]([NH:3][C@H:4]1[CH2:5][CH2:6][O:7][C:8]1=[O:9])[O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | N[C@@H](CCO)C(=O)O.O=C(Cl)OCc1ccccc1 | O=C(N[C@H]1CCOC1=O)OCc1ccccc1 | null | null | C(C)(=O)OCC.CCOCC | Protection | OtherReaction | 60f060c9be8c0f9f47d57d8207504da5b27b6f11d820f62a2b11b0b52ddc2a3e | 14d9cddc8d8d059a27f8895402ff3bbba59a333ae19b9270a85cc39dec8a319f | O=C(N[C@H]1CCOC1=O)OCc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].O-[C;H0;D3;+0:5](=[O;D1;H0:6])-[C:7](-[NH2;D1;+0:8])-[C:9]-[C:10]-[OH;D1;+0:11]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C:7]1-[C:9]-[C:10]-[O;H0;D2;+0:11]-[C;H0;D3;+0:5]-1=[O;D1;H0:6] | null | [] | null | null | 1 | HOUR | To L-homoserine (2 g) were added sodium hydrogen carbonate (3.7 g) and water (30 ml), and the mixture was stirred at room temperature for 1 hr. To the reaction mixture were further added benzyl chloroformate (3.9 ml) and ether (10 ml), and the mixture was stirred at room temperature for 18 hrs. The reaction mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Carboxylic acid.Ether.Primary alcohol.Primary amine | Carbamic ester.Ester | null | C1CCOC1 | C1CCOC1.c1ccccc1 | HCl | C(C)(=O)OCC.CCOCC | null | 1 | N[C@@H](CCO)C(=O)O.O=C(Cl)OCc1ccccc1>C(C)(=O)OCC.CCOCC>O=C(N[C@H]1CCOC1=O)OCc1ccccc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-223c89daee13463498f015655b9c9c34 | O=C(N[C@H]1CCOC1=O)OCc1ccccc1>>COC(=O)[C@H](CCO)NC(=O)OCc1ccccc1 | C(O)([O-])=O.[Na+].O=C1OCC[C@@H]1NC(OCC1=CC=CC=C1)=O.S(O)(O)(=O)=O>>C(C1=CC=CC=C1)OC(=O)N[C@H](C(=O)OC)CCO | [C:3]1(=[O:4])[C@@H:5]([NH:9][C:10](=[O:11])[O:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[CH2:6][CH2:7][O:8]1>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][CH2:7][OH:8])[NH:9][C:10](=[O:11])[O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | O=C(N[C@H]1CCOC1=O)OCc1ccccc1 | COC(=O)[C@H](CCO)NC(=O)OCc1ccccc1 | null | null | CO | Functional Group Addition | OtherReaction | e7be82e8b7b5578d9710977cd2af9dd128f2898bb91f3f983ef699f64fe4cbea | 9f276722861a2e173c0b9bb3b42e8a05761e167d704c44d8249e75309c44c1fe | c1ccccc1 | [O;D1;H0:1]=[C:2]-[#7:3]-[C:4]1-[C:5]-[C:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:8]-1=[O;D1;H0:9]>>[C;D1;H3:10]-[#8:11]-[C;H0;D3;+0:8](=[O;D1;H0:9])-[C:4](-[#7:3]-[C:2]=[O;D1;H0:1])-[C:5]-[C:6]-[OH;D1;+0:7] | null | [] | 60 | CELSIUS | 8 | HOUR | To the compound (500 mg) obtained in Step 1 were added methanol (5 ml) and conc. sulfuric acid (30 μl), and the mixture was stirred overnight at 60° C. To the reaction mixture was further added sodium hydrogen carbonate (250 mg), and the mixture was stirred at room temperature for 2 hrs. After celite filtration of the ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester.Primary alcohol | C1CCOC1 | null | c1ccccc1 | Other | CO | 60 | 8 | O=C(N[C@H]1CCOC1=O)OCc1ccccc1>CO>COC(=O)[C@H](CCO)NC(=O)OCc1ccccc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-acab1f45784f4d8e9846f2a7af06e5b9 | COc1ccc(I)cc1.O=c1ccc(C(F)(F)F)c[nH]1>>COc1ccc(-n2cc(C(F)(F)F)ccc2=O)cc1 | FC(C=1C=CC(NC1)=O)(F)F.IC1=CC=C(C=C1)OC.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>>COC1=CC=C(C=C1)N1C(C=CC(=C1)C(F)(F)F)=O | I[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:19][cH:18]1.[nH:7]1[cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15][c:16]1=[O:17]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[n:7]2[cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15][c:16]2=[O:17])[cH:18][cH:19]1 | COc1ccc(I)cc1.O=c1ccc(C(F)(F)F)c[nH]1 | COc1ccc(-n2cc(C(F)(F)F)ccc2=O)cc1 | null | [Cu]I | N | Heteroatom Alkylation and Arylation | OtherReaction | ec941adcff34376041316027981cd825966685269576a98b15d69b1d7b3db897 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | O=c1ccccn1-c1ccccc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[O;D1;H0:6]=[c:7](:[c:8]):[nH;D2;+0:9]:[c:10]:[c:11]>>[O;D1;H0:6]=[c:7](:[c:8]):[n;H0;D3;+0:9](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:10]:[c:11] | 39.2 | [{"value": 39.2, "product": "COC1=CC=C(C=C1)N1C(C=CC(=C1)C(F)(F)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.1, "product": "COC1=CC=C(C=C1)N1C(C=CC(=C1)C(F)(F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 135 | CELSIUS | null | null | A mixture of 5-(trifloromethyl)-2(1H)-pyridone (815.5 mg, 5 mmol), 4-iodoanisole (2.34 g, 10 mmol), CuI (952 mg, 5 mmol), K2CO3 (691 mg, 5 mmol) and DMF (5 ml) was heated at 135° C. overnight. The reaction mixture was diluted with 10% ammonia (15 ml) and extracted with ethyl acetate. The organic extract was washed with... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1.c1cccnc1 | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | HI | [Cu]I.N | 135 | null | COc1ccc(I)cc1.O=c1ccc(C(F)(F)F)c[nH]1>[Cu]I.N>COc1ccc(-n2cc(C(F)(F)F)ccc2=O)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-1582f9b6f74d41ce93a008fc838edd3a | COc1ccc(C(C)=O)cn1>>CC(=O)c1ccc(=O)[nH]c1 | COC1=NC=C(C=C1)C(C)=O.Cl.[OH-].[Na+]>>C(C)(=O)C=1C=CC(NC1)=O | C[O:8][c:7]1[cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:10][n:9]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7](=[O:8])[nH:9][cH:10]1 | COc1ccc(C(C)=O)cn1 | CC(=O)c1ccc(=O)[nH]c1 | null | null | null | Miscellaneous | OtherReaction | ffbb4288e7102e6f227d930be4a9510dc9e13ff3142954fd43347db64909ca58 | 291cad8b6dfbbd2c823b5c9d45efc37a166dc3454a9f151ac48cb357f4bc155f | O=c1cccc[nH]1 | C-[O;H0;D2;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c:5](-[C:6](-[C;D1;H3:7])=[O;D1;H0:8]):[c:9]:[n;H0;D2;+0:10]:1>>[C;D1;H3:7]-[C:6](=[O;D1;H0:8])-[c:5]1:[c:9]:[nH;D2;+0:10]:[c;H0;D3;+0:2](=[O;H0;D1;+0:1]):[c:3]:[c:4]:1 | null | [] | null | null | null | null | 2-methoxy-5-acetyl pyridine (1.51 g, 10 mmol) was treated with 6N HCl at 100° C. for 5 hours. The reaction mixture was neutralized with sodium hydroxide to pH 7 and then extracted several times with DCM. Organic layer was dried over sodium sulfate, evaporated and the residue was crystallized from ethyl acetate to give ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | null | c1ccncc1 | c1cccnc1 | c1cccnc1 | Other | null | null | null | COc1ccc(C(C)=O)cn1>>CC(=O)c1ccc(=O)[nH]c1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-84c3e5202db24794ad5e0005d8f79a15 | Brc1ccncc1.Cc1ccc(=O)[nH]c1>>Cc1ccc(=O)n(-c2ccncc2)c1 | CC=1C=CC(NC1)=O.Cl.BrC1=CC=NC=C1.C(=O)([O-])[O-].[K+].[K+]>>N1=CC=C(C=C1)N1C(C=CC(=C1)C)=O | Br[c:8]1[cH:9][cH:10][n:11][cH:12][cH:13]1.[CH3:1][c:2]1[cH:3][cH:4][c:5](=[O:6])[nH:7][cH:14]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](=[O:6])[n:7](-[c:8]2[cH:9][cH:10][n:11][cH:12][cH:13]2)[cH:14]1 | Brc1ccncc1.Cc1ccc(=O)[nH]c1 | Cc1ccc(=O)n(-c2ccncc2)c1 | null | [Cu]I | CN(C)C=O.N | Heteroatom Alkylation and Arylation | OtherReaction | 60a18b06cb8be8f5544817eed5d9b9e2ce91d4f256539e16476e4b9a3a0eaa2e | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | O=c1ccccn1-c1ccncc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1.[O;D1;H0:7]=[c:8](:[c:9]):[nH;D2;+0:10]:[c:11]:[c:12]>>[O;D1;H0:7]=[c:8](:[c:9]):[n;H0;D3;+0:10](-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1):[c:11]:[c:12] | 35 | [{"value": 35.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Compound 22 was synthesized by condensation of 5-methyl-2(1H)-pyridone (327.4 mg, 3 mmol) with 4-bromopyridine hydrochloride (778 mg, 4 mmol) in the presence of CuI (60 mg, 0.3 mmol) and K2CO3 (1.36 g, 10 mmol) in DMF (3 ml) at 135° C. overnight. The reaction mixture was diluted with 10% ammonia (15 ml) and extracted w... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccncc1.c1cccnc1 | c1ccncc1.c1ccncc1 | c1ccncc1.c1ccncc1 | HBr | [Cu]I.CN(C)C=O.N | null | null | Brc1ccncc1.Cc1ccc(=O)[nH]c1>[Cu]I.CN(C)C=O.N>Cc1ccc(=O)n(-c2ccncc2)c1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-a5e9cfcf879a480fa44c407279407e0b | COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1.Cc1ccc(=O)n(-c2ccccc2)c1>>Cc1ccc(=S)n(-c2ccccc2)c1 | C1(=CC=CC=C1)N1C(C=CC(=C1)C)=O.COC=1C=CC(=CC1)P2(=S)SP(=S)(S2)C=3C=CC(=CC3)OC>>C1(=CC=CC=C1)N1C(C=CC(=C1)C)=S | COc1ccc(P2(=S)SP(c3ccc(OC)cc3)(=[S:6])S2)cc1.O=[c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:14][n:7]1-[c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](=[S:6])[n:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14]1 | COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1.Cc1ccc(=O)n(-c2ccccc2)c1 | Cc1ccc(=S)n(-c2ccccc2)c1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 0b0d5108b038be416bc992e78e7617086f53580ef27799097b43dae1ce699878 | 6988b5bdf4783315bb3059677289ee20aff4c88fbf4684f4ee12b75839fcb0a0 | S=c1ccccn1-c1ccccc1 | C-O-c1:c:c:c(-P2(=S)-S-P(=[S;H0;D1;+0:1])(-c3:c:c:c(-O-C):c:c:3)-S-2):c:c:1.O=[c;H0;D3;+0:2](:[c:3]:[c:4]):[#7;a:5](-[c:6]):[c:7]>>[S;H0;D1;+0:1]=[c;H0;D3;+0:2](:[c:3]:[c:4]):[#7;a:5](-[c:6]):[c:7] | null | [] | null | null | null | null | 1-phenyl-5-methyl-2-pyridinone (555.7 mg, 3 mmol) was reacted with Lawesson's reagent (606.7 mg, 1.5 mmol) in toluene (5 ml) at 90° C. Reaction mixture was evaporated and the target compound was isolated by column chromatography (20-30% ethyl acetate-hexane) followed by crystallization from methyl-tert-butyl ether. Yie... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Monosulfide.Monosulfide | Thiocarbonyl | c1ccccc1.P1SPS1.c1ccccc1.c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | Other | C1(=CC=CC=C1)C | null | null | COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1.Cc1ccc(=O)n(-c2ccccc2)c1>C1(=CC=CC=C1)C>Cc1ccc(=S)n(-c2ccccc2)c1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-36f46d1507004530b03063bb98e56d46 | CCOC(=O)c1cccnc1Cl.c1ccc(-c2c[nH]cn2)cc1>>CCOC(=O)c1cccnc1-n1cnc(-c2ccccc2)c1 | ClC1=C(C(=O)OCC)C=CC=N1.C1(=CC=CC=C1)C=1N=CNC1.C(=O)([O-])[O-].[K+].[K+]>>C1(=CC=CC=C1)C=1N=CN(C1)C1=NC=CC=C1C(=O)OCC | Cl[c:11]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:7][cH:8][cH:9][n:10]1.[nH:12]1[cH:13][n:14][c:15](-[c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[cH:22]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][n:10][c:11]1-[n:12]1[cH:13][n:14][c:15](-[c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[cH:22]1 | CCOC(=O)c1cccnc1Cl.c1ccc(-c2c[nH]cn2)cc1 | CCOC(=O)c1cccnc1-n1cnc(-c2ccccc2)c1 | null | C1COCCOCCOCCOCCOCCO1 | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 17e9706c210dd3072f6fa31b56d9af1ca27df0f6c32f15008aa123bd82f87ddd | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc(-c2cn(-c3ccccn3)cn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8]):[c:9].[c:10]-[c:11]1:[#7;a:12]:[c:13]:[nH;D2;+0:14]:[c:15]:1>>[C:8]-[#8:7]-[C:5](=[O;D1;H0:6])-[c:4](:[c:9]):[c;H0;D3;+0:1](-[n;H0;D3;+0:14]1:[c:13]:[#7;a:12]:[c:11](-[c:10]):[c:15]:1):[#7;a:2]:[c:3] | 28.9 | [{"value": 28.9, "product": "C1(=CC=CC=C1)C=1N=CN(C1)C1=NC=CC=C1C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 160 | CELSIUS | null | null | A mixture of 5.0 g of ethyl 2-chloronicotinate (26.94 mmol), 3.4 g of 4-phenylimidazole (23.58 mmol), 7.6 g of K2CO3 and 80 mg of 18-crown-6 in 18 ml of N,N-dimethylformamide was heated in a microwave at 160° C. for about 1 hour. This was followed by concentrating, taking up the residue in dichloromethane, washing with... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccncc1.c1c[nH]cn1 | c1ccncc1.c1c[nH]cn1 | c1ccncc1.c1c[nH]cn1.c1ccccc1 | HCl | C1COCCOCCOCCOCCOCCO1.CN(C=O)C | 160 | null | CCOC(=O)c1cccnc1Cl.c1ccc(-c2c[nH]cn2)cc1>C1COCCOCCOCCOCCOCCO1.CN(C=O)C>CCOC(=O)c1cccnc1-n1cnc(-c2ccccc2)c1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-99393151c1744845bf4cf1d3a6c2e56e | CCOC(=O)c1cccnc1-n1cnc(-c2ccccc2)c1>>O=C(O)c1cccnc1-n1cnc(-c2ccccc2)c1 | [OH-].[Na+].C1(=CC=CC=C1)C=1N=CN(C1)C1=NC=CC=C1C(=O)OCC>>C1(=CC=CC=C1)C=1N=CN(C1)C1=NC=CC=C1C(=O)O | CC[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][cH:7][n:8][c:9]1-[n:10]1[cH:11][n:12][c:13](-[c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[cH:20]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][n:8][c:9]1-[n:10]1[cH:11][n:12][c:13](-[c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[cH:20]1 | CCOC(=O)c1cccnc1-n1cnc(-c2ccccc2)c1 | O=C(O)c1cccnc1-n1cnc(-c2ccccc2)c1 | null | null | CO | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2cn(-c3ccccn3)cn2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 71.9 | [{"value": 71.9, "product": "C1(=CC=CC=C1)C=1N=CN(C1)C1=NC=CC=C1C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 15 m of a 2N NaOH solution were added to a solution of 2.0 g of ethyl 2-(4-phenyl-1H-imidazol-1-yl)pyridine-3-carboxylate (6.82 mmol) in 30 ml of methanol, and the mixture was then stirred at room temperature for 2 hours. The reaction mixture was subsequently evaporated to dryness, mixed with 10 ml of H2O and neutraliz... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccncc1.c1c[nH]cn1.c1ccccc1 | Other | CO | null | 2 | CCOC(=O)c1cccnc1-n1cnc(-c2ccccc2)c1>CO>O=C(O)c1cccnc1-n1cnc(-c2ccccc2)c1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-6b46d268ecdb4ada8a7b6d15fb708a7b | NC(=O)C(O)C(N)Cc1ccccc1.O=C(O)c1cccnc1-n1cnc(-c2ccccc2)c1>>NC(=O)C(O)C(Cc1ccccc1)NC(=O)c1cccnc1-n1cnc(-c2ccccc2)c1 | Cl.NC(C(C(=O)N)O)CC1=CC=CC=C1.C(C)N=C=NCCCN(C)C.OC1=CC=CC=2NN=NC21.C1(=CC=CC=C1)C=1N=CN(C1)C1=NC=CC=C1C(=O)O.C(=O)(O)[O-].[Na+]>>NC(C(C(CC1=CC=CC=C1)NC(=O)C=1C(=NC=CC1)N1C=NC(=C1)C1=CC=CC=C1)O)=O | [NH2:1][C:2](=[O:3])[CH:4]([OH:5])[CH:6]([CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[NH2:14].O[C:15](=[O:16])[c:17]1[cH:18][cH:19][cH:20][n:21][c:22]1-[n:23]1[cH:24][n:25][c:26](-[c:27]2[cH:28][cH:29][cH:30][cH:31][cH:32]2)[cH:33]1>>[NH2:1][C:2](=[O:3])[CH:4]([OH:5])[CH:6]([CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12]... | NC(=O)C(O)C(N)Cc1ccccc1.O=C(O)c1cccnc1-n1cnc(-c2ccccc2)c1 | NC(=O)C(O)C(Cc1ccccc1)NC(=O)c1cccnc1-n1cnc(-c2ccccc2)c1 | null | null | ClCCl.CCN(CC)CC.C(C)N(CC)CC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCc1ccccc1)c1cccnc1-n1cnc(-c2ccccc2)c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[#7;a:6]):[#7;a:7]:[c:8].[C:9]-[C:10](-[NH2;D1;+0:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15]>>[#7;a:6]-[c:5](:[#7;a:7]:[c:8]):[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:11]-[C:10](-[C:9])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15]):[c:4] | 37.3 | [{"value": 37.3, "product": "NC(C(C(CC1=CC=CC=C1)NC(=O)C=1C(=NC=CC1)N1C=NC(=C1)C1=CC=CC=C1)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 2 | CELSIUS | 1 | HOUR | 0.75 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC), 0.51 g of hydroxylbenzotriazole (HOBt) and 0.55 ml of triethylamine (Et3N) were successively added to a solution of 1.0 g of 2-(4-phenyl-1H-imidazol-1-yl)pyridine-3-carboxylic acid (3.77 mmol) in 50 ml of dichloromethane at 0-4° C., and the mixture was stir... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccncc1.c1c[nH]cn1.c1ccccc1 | HO- | ClCCl.CCN(CC)CC.C(C)N(CC)CC | 2 | 1 | NC(=O)C(O)C(N)Cc1ccccc1.O=C(O)c1cccnc1-n1cnc(-c2ccccc2)c1>ClCCl.CCN(CC)CC.C(C)N(CC)CC>NC(=O)C(O)C(Cc1ccccc1)NC(=O)c1cccnc1-n1cnc(-c2ccccc2)c1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-aeb25d55c5c44a93bfc760d7a5f85022 | CCOC(=O)c1cccnc1Cl.c1ccc(-c2cn[nH]c2)cc1>>CCOC(=O)c1cccnc1-n1cc(-c2ccccc2)cn1 | O.ClC1=C(C(=O)OCC)C=CC=N1.C1(=CC=CC=C1)C=1C=NNC1.C(=O)([O-])[O-].[K+].[K+]>>C1(=CC=CC=C1)C=1C=NN(C1)C1=NC=CC=C1C(=O)OCC | Cl[c:11]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:7][cH:8][cH:9][n:10]1.[nH:12]1[cH:13][c:14](-[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[cH:21][n:22]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][n:10][c:11]1-[n:12]1[cH:13][c:14](-[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[cH:21][n:22]1 | CCOC(=O)c1cccnc1Cl.c1ccc(-c2cn[nH]c2)cc1 | CCOC(=O)c1cccnc1-n1cc(-c2ccccc2)cn1 | null | C1COCCOCCOCCOCCOCCO1 | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 8c8ea70bdc6e12e9a778ea0491595faafe3ec0c0a7fe7f6ae4184d378f504c00 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc(-c2cnn(-c3ccccn3)c2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8]):[c:9].[#7;a:10]1:[c:11]:[c:12]:[c:13]:[nH;D2;+0:14]:1>>[C:8]-[#8:7]-[C:5](=[O;D1;H0:6])-[c:4](:[c:9]):[c;H0;D3;+0:1](-[n;H0;D3;+0:14]1:[#7;a:10]:[c:11]:[c:12]:[c:13]:1):[#7;a:2]:[c:3] | 79.8 | [{"value": 79.8, "product": "C1(=CC=CC=C1)C=1C=NN(C1)C1=NC=CC=C1C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 130 | CELSIUS | 6 | HOUR | A mixture of 3.6 g of ethyl 2-chloronicotinate (19.4 mmol), 1.3 g of 4-phenylpyrazole (8.12 mmol), 4.4 g of K2CO3, 40 mg of 18-crown-6 and 30 mg of KI in 30 ml of N,N-dimethylformamide was stirred at 130° C. for 6 hours. For workup, H2O was added and, after extraction with ethyl acetate, the organic phase was washed wi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccncc1.c1cn[nH]c1 | c1ccncc1.c1cn[nH]c1 | c1ccncc1.c1cn[nH]c1.c1ccccc1 | HCl | C1COCCOCCOCCOCCOCCO1.CN(C=O)C | 130 | 6 | CCOC(=O)c1cccnc1Cl.c1ccc(-c2cn[nH]c2)cc1>C1COCCOCCOCCOCCOCCO1.CN(C=O)C>CCOC(=O)c1cccnc1-n1cc(-c2ccccc2)cn1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-9e84da6c8ed8414fa732e854834986ac | CCCCC(NC(=O)c1cccnc1-n1cc(-c2ccccc2)cn1)C(O)C(N)=O>>CCCCC(NC(=O)c1cccnc1-n1cc(-c2ccccc2)cn1)C(=O)C(N)=O | O.C(CCl)Cl.ClC(C(=O)O)Cl.NC(C(O)C(CCCC)NC(=O)C=1C(=NC=CC1)N1N=CC(=C1)C1=CC=CC=C1)=O>>NC(C(=O)C(CCCC)NC(C1=C(N=CC=C1)N1N=CC(=C1)C1=CC=CC=C1)=O)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([NH:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][cH:12][n:13][c:14]1-[n:15]1[cH:16][c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[cH:24][n:25]1)[CH:26]([OH:27])[C:28]([NH2:29])=[O:30]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([NH:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][cH:12][n:13][c:14]1-[n:15]1[... | CCCCC(NC(=O)c1cccnc1-n1cc(-c2ccccc2)cn1)C(O)C(N)=O | CCCCC(NC(=O)c1cccnc1-n1cc(-c2ccccc2)cn1)C(=O)C(N)=O | null | null | CS(=O)C | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | c1ccc(-c2cnn(-c3ccccn3)c2)cc1 | [C:1]-[C:2](-[#7:3]-[C:4]=[O;D1;H0:5])-[CH;D3;+0:6](-[OH;D1;+0:7])-[C:8](-[N;D1;H2:9])=[O;D1;H0:10]>>[C:1]-[C:2](-[#7:3]-[C:4]=[O;D1;H0:5])-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[C:8](-[N;D1;H2:9])=[O;D1;H0:10] | 76 | [{"value": 76.0, "product": "NC(C(=O)C(CCCC)NC(C1=C(N=CC=C1)N1N=CC(=C1)C1=CC=CC=C1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 0.47 g of EDC and 0.08 ml of dichloroacetic acid were added to 100 mg of N-[1-(2-amino-1-hydroxy-2-oxoethyl)pentyl]-2-(4-phenyl-1H-pyrazol-1-yl)pyridine-3-carboxamide (0.25 mmol) in 4 ml of dimethyl sulfoxide, and the mixture was stirred at room temperature overnight. For workup, the reaction mixture was poured into H2... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | c1ccncc1.c1cn[nH]c1.c1ccccc1 | null | CS(=O)C | null | 8 | CCCCC(NC(=O)c1cccnc1-n1cc(-c2ccccc2)cn1)C(O)C(N)=O>CS(=O)C>CCCCC(NC(=O)c1cccnc1-n1cc(-c2ccccc2)cn1)C(=O)C(N)=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-716eb6f2d6eb4ce88d4e17552e7be911 | CCCCC(N)C(O)C(N)=O.O=C(O)c1cccnc1-n1ccc(-c2ccccc2)n1>>CCCCC(NC(=O)c1cccnc1-n1ccc(-c2ccccc2)n1)C(=O)C(N)=O | C1(=CC=CC=C1)C1=NN(C=C1)C1=NC=CC=C1C(=O)O.Cl.NC(C(C(=O)N)O)CCCC>>NC(C(=O)C(CCCC)NC(C1=C(N=CC=C1)N1N=C(C=C1)C1=CC=CC=C1)=O)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([NH2:6])[CH:26]([OH:27])[C:28]([NH2:29])=[O:30].O[C:7](=[O:8])[c:9]1[cH:10][cH:11][cH:12][n:13][c:14]1-[n:15]1[cH:16][cH:17][c:18](-[c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[n:25]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([NH:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][cH:12][n:13][c:14]1-[n:15... | CCCCC(N)C(O)C(N)=O.O=C(O)c1cccnc1-n1ccc(-c2ccccc2)n1 | CCCCC(NC(=O)c1cccnc1-n1ccc(-c2ccccc2)n1)C(=O)C(N)=O | null | null | null | Acylation | OtherReaction | 8554061fb314d4e4af39a78d0e57cc7be91d5dc48cd775935bb01677688ab393 | 281f2d95d3425ef7aa1c4b6ccfdd7f7cb1a3e6687825f19e34c7f0ed073b150d | c1ccc(-c2ccn(-c3ccccn3)n2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[#7;a:6]):[#7;a:7]:[c:8].[C:9]-[C:10](-[NH2;D1;+0:11])-[CH;D3;+0:12](-[OH;D1;+0:13])-[C:14](-[N;D1;H2:15])=[O;D1;H0:16]>>[#7;a:6]-[c:5](:[#7;a:7]:[c:8]):[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:11]-[C:10](-[C:9])-[C;H0;D3;+0:12](=[O;H0;D1;+0:13])-[C:14](-[N;D1;H2... | null | [] | null | null | null | null | Preparation in analogy to Example 5 by coupling 2-(3-phenyl-1H-pyrazol-1-yl)pyridine-3-carboxylic acid and 3-amino-2-hydroxyheptanamide hydrochloride and subsequent oxidation afforded 40 mg of the title compound as a white solid.
Conditions: See reaction.notes.procedure_details.
Workup: Preparation in analogy to Exampl... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary alcohol.Primary amine | Ketone.Secondary amide | null | null | c1ccncc1.c1cc[nH]n1.c1ccccc1 | HO- | null | null | null | CCCCC(N)C(O)C(N)=O.O=C(O)c1cccnc1-n1ccc(-c2ccccc2)n1>>CCCCC(NC(=O)c1cccnc1-n1ccc(-c2ccccc2)n1)C(=O)C(N)=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-1801477917e1466bbc289010bb42ac64 | C1COCCN1.CC(=O)c1ccc(C=O)cc1>>CC(=O)c1ccc(CN2CCOCC2)cc1 | C(C)(=O)C1=CC=C(C=O)C=C1.N1CCOCC1>>N1(CCOCC1)CC1=CC=C(C=C1)C(C)=O | [NH:9]1[CH2:10][CH2:11][O:12][CH2:13][CH2:14]1.O=[CH:8][c:7]1[cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:16][cH:15]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[cH:15][cH:16]1 | C1COCCN1.CC(=O)c1ccc(C=O)cc1 | CC(=O)c1ccc(CN2CCOCC2)cc1 | null | [O-]S(=O)(=O)C(F)(F)F.[Sc+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F | O1CCCC1 | Heteroatom Alkylation and Arylation | reductive amination | 073d98e7dcd77aafeef71a76da7e61b2751c934600f6fff04db700a08f3e4453 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(CN2CCOCC2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[#8:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#8:5]-[C:10]-[C:9]-1):[c:4] | null | [] | null | null | null | null | 4.7 g of 1,4-dihydro-2,6-dimethyl-3,5-pyridinecarboxylate and 1.3 g of scandium triflate were added to 2.75 g of 4-acetylbenzaldehyde (18.56 mmol), 1.7 ml of morpholine and 3 g of 4 Å molecular sieves in 100 ml of tetrahydrofuran under argon, and the mixture was heated to reflux for 3 hours. The mixture was concentrate... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1COCCN1 | C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1 | Other | [O-]S(=O)(=O)C(F)(F)F.[Sc+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.O1CCCC1 | null | null | C1COCCN1.CC(=O)c1ccc(C=O)cc1>[O-]S(=O)(=O)C(F)(F)F.[Sc+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.O1CCCC1>CC(=O)c1ccc(CN2CCOCC2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-05e877e49f6e4a7498b3988be9eb552d | CC(=O)c1ccc(N2CCOCC2)cc1.NN>>c1cc(-c2ccc(N3CCOCC3)cc2)n[nH]1 | CC(=O)C1=CC=C(C=C1)N2CCOCC2.COC(N(C)C)OC.O.NN>>N1N=C(C=C1)C1=CC=C(C=C1)N1CCOCC1 | O=[C:3]([CH3:2])[c:4]1[cH:5][cH:6][c:7]([N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[cH:14][cH:15]1.[NH2:16][NH2:17]>>[cH:1]1[cH:2][c:3](-[c:4]2[cH:5][cH:6][c:7]([N:8]3[CH2:9][CH2:10][O:11][CH2:12][CH2:13]3)[cH:14][cH:15]2)[n:16][nH:17]1 | CC(=O)c1ccc(N2CCOCC2)cc1.NN | c1cc(-c2ccc(N3CCOCC3)cc2)n[nH]1 | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | ce806ba64bd7c63bfb10c92a750a343bf243ac2073695155e142d7a884e54966 | 1544c5676618f0f36e8bbf58b325093878e04c49fa9119d5ee93cb092dbc631d | c1cc(-c2ccc(N3CCOCC3)cc2)n[nH]1 | O=[C;H0;D3;+0:1](-[CH3;D1;+0:2])-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7].[NH2;D1;+0:8]-[NH2;D1;+0:9]>>[c:5]:[c:4]:[c;H0;D3;+0:3](-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[c:10]:[nH;D2;+0:9]:[n;H0;D2;+0:8]:1):[c:6]:[c:7] | null | [] | null | null | null | null | A mixture of 2.05 g of 4-morpholinoacetophenone (10 mmol) and N,N-dimethylformamide dimethyl acetal was heated under reflux for 7 hours. The mixture was then mixed with 30 ml of methanol and, after addition of 0.57 ml of hydrazine hydrate, again heated under reflux for about 6 hours. The solid formed on cooling the mix... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone | null | null | c1cn[nH]c1 | c1cn[nH]c1.c1ccccc1.C1COCC[NH]1 | null | CO | null | null | CC(=O)c1ccc(N2CCOCC2)cc1.NN>CO>c1cc(-c2ccc(N3CCOCC3)cc2)n[nH]1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-ffbc36b5cc20433197443719ded904be | N[C@@H](Cc1cccs1)C(=O)O.O=C(Cl)OCc1ccccc1>>O=C(NC(CO)Cc1cccs1)OCc1ccccc1 | S1C(=CC=C1)C[C@H](N)C(=O)O.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].ClC(=O)OCC1=CC=CC=C1.[OH-].[Na+]>>OCC(CC=1SC=CC1)NC(OCC1=CC=CC=C1)=O | O=[C:5]([C@@H:4]([NH2:3])[CH2:7][c:8]1[cH:9][cH:10][cH:11][s:12]1)[OH:6].Cl[C:2](=[O:1])[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[O:1]=[C:2]([NH:3][CH:4]([CH2:5][OH:6])[CH2:7][c:8]1[cH:9][cH:10][cH:11][s:12]1)[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | N[C@@H](Cc1cccs1)C(=O)O.O=C(Cl)OCc1ccccc1 | O=C(NC(CO)Cc1cccs1)OCc1ccccc1 | null | null | O.O1CCCC1 | Protection | OtherReaction | e0f88bae40c56e433df81e8c9048e60b6f16d1400c3d6034f58ee5fc72d584d9 | 4e4ec4691a71be0529402652588024437813526f836a9ae5f21e90fb1333066a | O=C(NCCc1cccs1)OCc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].O=[C;H0;D3;+0:5](-[O;D1;H1:6])-[C@@H;D3;+0:7](-[NH2;D1;+0:8])-[C:9]-[c:10]:[#16;a:11]>>[#16;a:11]:[c:10]-[C:9]-[CH;D3;+0:7](-[CH2;D2;+0:5]-[O;D1;H1:6])-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4] | 96.9 | [{"value": 96.9, "product": "OCC(CC=1SC=CC1)NC(OCC1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 24.8 g of 3-(2-thienyl)alanine (144.8 mmol) were added in portions to 11.0 g of LiAlH4 in 550 ml of tetrahydrofuran, heated to reflux. The mixture was then heated under reflux for 8 hours and subsequently stirred at room temperature overnight. 17.6 ml of 10% NaOH solution were added and then 22 ml of H2O were slowly ad... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Carboxylic acid.Ether.Primary amine | Carbamic ester.Ether.Primary alcohol | null | null | c1ccsc1.c1ccccc1 | Other | O.O1CCCC1 | null | 8 | N[C@@H](Cc1cccs1)C(=O)O.O=C(Cl)OCc1ccccc1>O.O1CCCC1>O=C(NC(CO)Cc1cccs1)OCc1ccccc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-a30447cebba846cdbf38a51b326d64d3 | CS(C)=O.O=C(NC(CO)Cc1cccs1)OCc1ccccc1>>NC(=O)C(O)C(Cc1cccs1)NC(=O)OCc1ccccc1 | OCC(CC=1SC=CC1)NC(OCC1=CC=CC=C1)=O.C(C)N(CC)CC.CS(=O)C>>NC(C(C(CC=1SC=CC1)NC(OCC1=CC=CC=C1)=O)O)=O | CS(C)=[O:3].[CH2:4]([OH:5])[CH:6]([CH2:7][c:8]1[cH:9][cH:10][cH:11][s:12]1)[NH:13][C:14](=[O:15])[O:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[NH2:1][C:2](=[O:3])[CH:4]([OH:5])[CH:6]([CH2:7][c:8]1[cH:9][cH:10][cH:11][s:12]1)[NH:13][C:14](=[O:15])[O:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1 | CS(C)=O.O=C(NC(CO)Cc1cccs1)OCc1ccccc1 | NC(=O)C(O)C(Cc1cccs1)NC(=O)OCc1ccccc1 | null | null | O1CCCC1.OS(=O)(=O)O.Cl | Acylation | OtherReaction | 02cbffec8f2b1a1d4412a163c3ca159e9a2a669fcfd2f6140bb087889daba937 | fd4834add846ac4eb10239c604644ca3dd022741c062c1e1d7af626d3903f85a | O=C(NCCc1cccs1)OCc1ccccc1 | C-S(-C)=[O;H0;D1;+0:1].[C:2]-[C:3](-[#7:4]-[C:5]=[O;D1;H0:6])-[CH2;D2;+0:7]-[O;D1;H1:8]>>[C:2]-[C:3](-[#7:4]-[C:5]=[O;D1;H0:6])-[CH;D3;+0:7](-[O;D1;H1:8])-[C:9](-[N;D1;H2:10])=[O;H0;D1;+0:1] | null | [] | null | null | 3 | HOUR | 40.2 g of pyridine-SO3 complex were added in portions to a mixture of 36.8 g of phenylmethyl [2-hydroxy-1-(2-thienylmethyl)ethyl]carbamate (126.3 mmol) and 51.2 g of triethylamine in 220 ml of dimethyl sulfoxide at about 16° C., and the mixture was stirred at room temperature for 3 hours. It was then poured into ice-wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfoxide | Primary amide.Secondary alcohol | null | null | c1ccsc1.c1ccccc1 | Other | O1CCCC1.OS(=O)(=O)O.Cl | null | 3 | CS(C)=O.O=C(NC(CO)Cc1cccs1)OCc1ccccc1>O1CCCC1.OS(=O)(=O)O.Cl>NC(=O)C(O)C(Cc1cccs1)NC(=O)OCc1ccccc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-4c437eb2a50340bdb7d8605ab5fe4e4d | NC(=O)C(O)C(Cc1cccs1)NC(=O)OCc1ccccc1>>NC(=O)C(O)C(N)Cc1cccs1 | Br.NC(C(C(CC=1SC=CC1)NC(OCC1=CC=CC=C1)=O)O)=O>>NC(C(C(=O)N)O)CC=1SC=CC1 | O=C(OCc1ccccc1)[NH:7][CH:6]([CH:4]([C:2]([NH2:1])=[O:3])[OH:5])[CH2:8][c:9]1[cH:10][cH:11][cH:12][s:13]1>>[NH2:1][C:2](=[O:3])[CH:4]([OH:5])[CH:6]([NH2:7])[CH2:8][c:9]1[cH:10][cH:11][cH:12][s:13]1 | NC(=O)C(O)C(Cc1cccs1)NC(=O)OCc1ccccc1 | NC(=O)C(O)C(N)Cc1cccs1 | null | null | C(C)(=O)O | Reduction | Hydrogenolysis of amides/imides/carbamates | 087b6600ba91d3df931fe6979f2445c192cbfd59e04fd2d8a10f7c7573ac669f | 4e549866ec1acadec4c84aaf8495992a28ec78d8ea5ef1b9f44dd843b0dcb7d4 | c1ccsc1 | O=C(-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]-[C:5](-[N;D1;H2:6])=[O;D1;H0:7]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4]-[C:5](-[N;D1;H2:6])=[O;D1;H0:7] | 131.3 | [{"value": 131.3, "product": "NC(C(C(=O)N)O)CC=1SC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 70 ml of 30% HBr in glacial acetic acid were added to 11 g of phenylmethyl [3-amino-2-hydroxy-3-oxo-1-(2-thienylmethyl)propyl]carbamate (29.66 mmol) in 30 ml of glacial acetic acid. After about 2 hours, the mixture was concentrated and the resulting residue was stirred firstly with cyclohexane and then with dichloromet... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | c1ccccc1 | null | c1ccsc1 | HO- | C(C)(=O)O | null | 2 | NC(=O)C(O)C(Cc1cccs1)NC(=O)OCc1ccccc1>C(C)(=O)O>NC(=O)C(O)C(N)Cc1cccs1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-cd3f5ea0bca94cc682df0f592fbe9530 | CCN(CC)Cc1ccc(C#N)cc1>>CCN(CC)Cc1ccc(C(C)=O)cc1 | C(C)N(CC)CC1=CC=C(C#N)C=C1.C[Mg]Br.C(C)OCC>>C(C)N(CC)CC1=CC=C(C=C1)C(C)=O | N#[C:11][c:10]1[cH:9][cH:8][c:7]([CH2:6][N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])[cH:15][cH:14]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][c:7]1[cH:8][cH:9][c:10]([C:11]([CH3:12])=[O:13])[cH:14][cH:15]1 | CCN(CC)Cc1ccc(C#N)cc1 | CCN(CC)Cc1ccc(C(C)=O)cc1 | null | null | C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | 54622de249eb9a5622e28710a02d261b08e09c3ee957106ef84a0e4751ccb30f | 957d5e0aaa82a4f5b73d699040cb2acd7f615417c9e400cbb7a63fa4c133449a | c1ccccc1 | N#[C;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[C;D1;H3:5]-[C;H0;D3;+0:1](=[O;D1;H0:6])-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A solution of 12.1 g of 4-[diethylaminomethyl]benzonitrile in 40 ml of toluene was added to a solution of methylmagnesium bromide (43 ml of a 3 M solution in diethyl ether) in 40 ml of toluene, and the mixture was heated to reflux. Completion of the reaction was followed by pouring into ice-water, extracting with methy... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Ketone | null | null | c1ccccc1 | null | C1(=CC=CC=C1)C | null | null | CCN(CC)Cc1ccc(C#N)cc1>C1(=CC=CC=C1)C>CCN(CC)Cc1ccc(C(C)=O)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-0253a7c0b59e4adb8b82bec7322589c9 | CN(C)C=O.NN.O=C(O)Cc1ccccc1F>>Fc1ccccc1-c1cn[nH]c1 | O=P(Cl)(Cl)Cl.CN(C=O)C.FC1=C(C=CC=C1)CC(=O)O.CN(C=O)C.O.NN>>FC1=C(C=CC=C1)C=1C=NNC1 | CN(C=O)[CH3:12].[NH2:10][NH2:11].O=[C:9](O)[CH2:8][c:7]1[c:2]([F:1])[cH:3][cH:4][cH:5][cH:6]1>>[F:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1-[c:8]1[cH:9][n:10][nH:11][cH:12]1 | CN(C)C=O.NN.O=C(O)Cc1ccccc1F | Fc1ccccc1-c1cn[nH]c1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | cb1e232d6546765de9c7c47fa270f7d608694a4b5e00103ba799a3ce5e177500 | 2580262a71b714b88646a3f0626cfc3ad19ee43553eb6878ef4cc1682843da23 | c1ccc(-c2cn[nH]c2)cc1 | C-N(-[CH3;D1;+0:1])-C=O.O-[C;H0;D3;+0:2](=O)-[CH2;D2;+0:3]-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7](-[F;D1;H0:8]):[c:9].[NH2;D1;+0:10]-[NH2;D1;+0:11]>>[F;D1;H0:8]-[c:7](:[c:9]):[c;H0;D3;+0:4](-[c;H0;D3;+0:3]1:[cH;D2;+0:1]:[nH;D2;+0:11]:[n;H0;D2;+0:10]:[cH;D2;+0:2]:1):[c:5]:[c:6] | null | [] | 70 | CELSIUS | null | null | 11.08 ml of N,N-dimethylformamide was slowly added dropwise to 11.03 ml of POCl3 were at 0-5° C. while stirring and, after about 5 minutes a solution of 2-fluorophenylacetic acid (6 g, 38.9 mmol) in 20 ml of N,N-dimethylformamide was added dropwise. The mixture was then heated at 70° C. for about 17 hours. The mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Carboxylic acid.Tertiary amide | null | null | c1cn[nH]c1 | c1ccccc1.c1cn[nH]c1 | HO- | C(C)O | 70 | null | CN(C)C=O.NN.O=C(O)Cc1ccccc1F>C(C)O>Fc1ccccc1-c1cn[nH]c1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-71fdf134242643dab57ea5ca4a673cc1 | COc1cc(OC)c(Cl)cc1N>>COc1cc(OC)c(N=[N+]=[N-])cc1Cl | [N-]=[N+]=[N-].[Na+].N(=O)[O-].[Na+].OS(=O)(=O)O.ClC=1C(=CC(=C(C1)N)OC)OC>>N(=[N+]=[N-])C1=C(C=C(C(=C1)Cl)OC)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8]([NH2:9])[cH:12][c:13]1[Cl:14]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8]([N:9]=[N+:10]=[N-:11])[cH:12][c:13]1[Cl:14] | COc1cc(OC)c(Cl)cc1N | COc1cc(OC)c(N=[N+]=[N-])cc1Cl | null | null | O | Miscellaneous | Amine to azide | 874c0cf1984ab0c3156493e6524e4a76434860bf4d8c4f6115608f4b54932f2a | 0dcf06f7cec37f2f50b2497bf88be0f43ce4890a2df8b6f4eb18df3f7b6a2a7d | c1ccccc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]>>[N;-;D1;H0:5]=[#7;+:6]=[N;H0;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 0 | CELSIUS | null | null | To a solution of concentrated H2SO4 (5 mL) in water (15 mL), 5-chloro-2,4-dimethoxy-phenylamine (3 g, 16 mmol) was added, resulting a deep purple suspension. More water (15 mL) was then added and the mixture was cooled and stirred vigorously at 0° C. in an ice-salt bath. A solution of sodium nitrite (1.2 g, 17.4 mmol) ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Azide | null | null | c1ccccc1 | Other | O | 0 | null | COc1cc(OC)c(Cl)cc1N>O>COc1cc(OC)c(N=[N+]=[N-])cc1Cl |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-7a8b9422f4634db6947a7b29d86ba228 | COC(=O)CC(=O)c1ccc(F)cc1.COc1cc(OC)c(N=[N+]=[N-])cc1Cl>>COc1cc(OC)c(-n2nnc(C(=O)O)c2-c2ccc(F)cc2)cc1Cl | N(=[N+]=[N-])C1=C(C=C(C(=C1)Cl)OC)OC.COC(CC(=O)C1=CC=C(C=C1)F)=O.[O-]CC.[Na+]>>ClC=1C(=CC(=C(C1)N1N=NC(=C1C1=CC=C(C=C1)F)C(=O)O)OC)OC | C[O:15][C:13]([CH2:12][C:16](=O)[c:17]1[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]1)=[O:14].[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8]([N:9]=[N+:10]=[N-:11])[cH:24][c:25]1[Cl:26]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[n:9]2[n:10][n:11][c:12]([C:13](=[O:14])[OH:15])[c:16]2-[c:17]2[cH:18][cH:19][c:20]([... | COC(=O)CC(=O)c1ccc(F)cc1.COc1cc(OC)c(N=[N+]=[N-])cc1Cl | COc1cc(OC)c(-n2nnc(C(=O)O)c2-c2ccc(F)cc2)cc1Cl | null | null | CCO | Aromatic Heterocycle Formation | OtherReaction | 0b65b0938d8b6dfeb0e7e505a73bccea293d6a6eaaf965853df1f72030a258eb | 866a5dabd8786545c389ddfb3f78135d14145a153228997f1aa439074835e2d5 | c1ccc(-c2cnnn2-c2ccccc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:4]-[C;H0;D3;+0:5](=O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10].[#8:11]-[c:12](:[c:13]):[c;H0;D3;+0:14](-[N;H0;D2;+0:15]=[N+;H0;D2:16]=[N-;H0;D1:17]):[c:18]:[c:19]>>[#8:11]-[c:12](:[c:13]):[c;H0;D3;+0:14](-[n;H0;D3;+0:15]1:[n;H0;D2;+0:16]:[n;H0;D2;+0:17]:[c;H0;D3;+0:4](-[... | null | [] | null | null | null | null | 1-Azido-5-chloro-2,4-dimethoxy-benzene (0.4 g, 1.9 mmol), 3-(4-Fluoro-phenyl)-3-oxo-propionic acid methyl ester (0.42 g, 2.2 mmol) and sodium ethoxide in EtOH (70 mg of sodium in 15 mL EtOH) were refluxed for 3 hours. During the reaction, the solution turned brown from dark green. After that, EtOH was evaporated off an... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Azide | Carboxylic acid | null | c1c[nH]nn1 | c1ccccc1.c1c[nH]nn1.c1ccccc1 | HO- | CCO | null | null | COC(=O)CC(=O)c1ccc(F)cc1.COc1cc(OC)c(N=[N+]=[N-])cc1Cl>CCO>COc1cc(OC)c(-n2nnc(C(=O)O)c2-c2ccc(F)cc2)cc1Cl |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-4325811208714cde96d7855dd97c1686 | COc1cc(OC)c(-n2nnc(C(=O)O)c2-c2ccc(F)cc2)cc1Cl>>O=C(O)c1nnn(-c2ccc(O)cc2O)c1-c1ccc(F)cc1 | O.ClC=1C(=CC(=C(C1)N1N=NC(=C1C1=CC=C(C=C1)F)C(=O)O)OC)OC.C(C)(=O)O.C(C)(=O)OC(C)=O>>OC1=C(C=CC(=C1)O)N1N=NC(=C1C1=CC=C(C=C1)F)C(=O)O | C[O:12][c:11]1[c:10](Cl)[cH:9][c:8](-[n:7]2[n:6][n:5][c:4]([C:2](=[O:1])[OH:3])[c:16]2-[c:17]2[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]2)[c:14]([O:15]C)[cH:13]1>>[O:1]=[C:2]([OH:3])[c:4]1[n:5][n:6][n:7](-[c:8]2[cH:9][cH:10][c:11]([OH:12])[cH:13][c:14]2[OH:15])[c:16]1-[c:17]1[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]1 | COc1cc(OC)c(-n2nnc(C(=O)O)c2-c2ccc(F)cc2)cc1Cl | O=C(O)c1nnn(-c2ccc(O)cc2O)c1-c1ccc(F)cc1 | null | null | I | Deprotection | OtherReaction | d94bbd2940e704b88f9b19180a9a715414a77f129a71336a157a38588cbf3762 | de22cbaee6faa79fd8152989102eaf0c8c1ed6f3e27d914f1d9154602422fea1 | c1ccc(-c2cnnn2-c2ccccc2)cc1 | C-[O;H0;D2;+0:1]-[c:2]1:[c:3]:[c:4](-[O;H0;D2;+0:5]-C):[c:6]:[c:7]:[c;H0;D3;+0:8]:1-Cl>>[OH;D1;+0:1]-[c:2]1:[c:3]:[c:4](-[OH;D1;+0:5]):[c:6]:[c:7]:[cH;D2;+0:8]:1 | null | [] | null | null | null | null | 1-(5-Chloro-2,4-dimethoxy-phenyl)-5-(4-fluoro-phenyl)-1H-[1,2,3]triazole-4-carboxylic acid (0.29 g, 0.77 mmol) was refluxed in a mixture of hydroiodic acid (5 mL), acetic acid (1 mL) and acetic anhydride (0.5 mL) for 16 hours. When cooled, water (20 mL) was added and the aqueous layer was extracted with EtOAc (2×15 mL)... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Ether | Aromatic alcohol.Aromatic alcohol | c1ccccc1 | c1ccccc1 | c1c[nH]nn1.c1ccccc1.c1ccccc1 | HCl | I | null | null | COc1cc(OC)c(-n2nnc(C(=O)O)c2-c2ccc(F)cc2)cc1Cl>I>O=C(O)c1nnn(-c2ccc(O)cc2O)c1-c1ccc(F)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-71fa31f77a6743d998658e65f9b69f56 | CCO.O=C(O)c1nnn(-c2ccc(O)cc2O)c1-c1ccc(F)cc1>>CCOC(=O)c1nnn(-c2ccc(O)cc2O)c1-c1ccc(F)cc1 | OC1=C(C=CC(=C1)O)N1N=NC(=C1C1=CC=C(C=C1)F)C(=O)O.CCO>>C(C)OC(=O)C=1N=NN(C1C1=CC=C(C=C1)F)C1=C(C=C(C=C1)O)O | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])[c:6]1[n:7][n:8][n:9](-[c:10]2[cH:11][cH:12][c:13]([OH:14])[cH:15][c:16]2[OH:17])[c:18]1-[c:19]1[cH:20][cH:21][c:22]([F:23])[cH:24][cH:25]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][n:8][n:9](-[c:10]2[cH:11][cH:12][c:13]([OH:14])[cH:15][c:16]2[OH:17])[c:18]1-[c:19]1[cH:20][cH:21][c... | CCO.O=C(O)c1nnn(-c2ccc(O)cc2O)c1-c1ccc(F)cc1 | CCOC(=O)c1nnn(-c2ccc(O)cc2O)c1-c1ccc(F)cc1 | null | OS(=O)(=O)O | null | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | c1ccc(-c2cnnn2-c2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[#7;a:5]:[#7;a:6](-[c:7]):[c:8]:1-[c:9].[C;D1;H3:10]-[C:11]-[OH;D1;+0:12]>>[C;D1;H3:10]-[C:11]-[O;H0;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[#7;a:5]:[#7;a:6](-[c:7]):[c:8]:1-[c:9] | null | [] | null | null | null | null | 1-(2,4-Dihydroxy-phenyl)-5-(4-fluoro-phenyl)-1H-[1,2,3]triazole-4-carboxylic acid (0.15 g, 0.48 mmol) was refluxed in EtOH (20 mL) in the presence of 5 drops of concentrated H2SO4 for 3 hours. After evaporation of the solvent, EtOAc (20 mL) was added. The organic layer was then washed with sat. NaHCO3 (2×10 mL) and bri... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1c[nH]nn1.c1ccccc1.c1ccccc1 | HO- | OS(=O)(=O)O | null | null | CCO.O=C(O)c1nnn(-c2ccc(O)cc2O)c1-c1ccc(F)cc1>OS(=O)(=O)O>CCOC(=O)c1nnn(-c2ccc(O)cc2O)c1-c1ccc(F)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-ecce3c714f654f259f67249d6ff0a797 | NNC(=S)NN.O=C(Cl)c1cccs1.O=C(O)Cc1ccc2c(c1)OCO2>>c1csc(-c2nn3c(Cc4ccc5c(c4)OCO5)nnc3s2)c1 | O1COC2=C1C=CC(=C2)CC(=O)O.NNC(=S)NN.S1C(=CC=C1)C(=O)Cl.C(=O)(O)[O-].[Na+]>>O1COC2=C1C=CC(=C2)CC2=NN=C1SC(=NN12)C=1SC=CC1 | [NH2:6][NH:7][C:21]([NH:20][NH2:19])=[S:22].O=[C:5](Cl)[c:4]1[s:3][cH:2][cH:1][cH:23]1.O=[C:8](O)[CH2:9][c:10]1[cH:11][cH:12][c:13]2[c:14]([cH:15]1)[O:16][CH2:17][O:18]2>>[cH:1]1[cH:2][s:3][c:4](-[c:5]2[n:6][n:7]3[c:8]([CH2:9][c:10]4[cH:11][cH:12][c:13]5[c:14]([cH:15]4)[O:16][CH2:17][O:18]5)[n:19][n:20][c:21]3[s:22]2)[... | NNC(=S)NN.O=C(Cl)c1cccs1.O=C(O)Cc1ccc2c(c1)OCO2 | c1csc(-c2nn3c(Cc4ccc5c(c4)OCO5)nnc3s2)c1 | null | null | CO.C(Cl)Cl.[Cl-] | Aromatic Heterocycle Formation | OtherReaction | 075249aea7443a3dc9b3adfbf6003548246d18882806db443ce4f40a806522dd | a424a89ee7879b662e8417ff710a9ee9342bb2a8322b386d8bb194dbe45d0b95 | c1csc(-c2nn3c(Cc4ccc5c(c4)OCO5)nnc3s2)c1 | Cl-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[#16;a:3]:[c:4]:[c:5]:[c:6]:1.O-[C;H0;D3;+0:7](=O)-[C:8]-[c:9].[NH2;D1;+0:10]-[NH;D2;+0:11]-[C;H0;D3;+0:12](=[S;H0;D1;+0:13])-[NH;D2;+0:14]-[NH2;D1;+0:15]>>[c:9]-[C:8]-[c;H0;D3;+0:7]1:[n;H0;D2;+0:10]:[n;H0;D2;+0:11]:[c;H0;D3;+0:12]2:[s;H0;D2;+0:13]:[c;H0;D3;+0:1](-[c;H0;D3;+0:2]3:[... | null | [] | 170 | CELSIUS | null | null | As shown in FIG. 2, 2-(benzo[d][1,3]dioxol-5-yl)acetic acid (1 mmol) and thiocarbonohydrazide (1.5 mmol) were heated at 170° C. for 15 min. The mixture was cooled and taken up in 5% MeOH/CH2Cl2 and saturated NaHCO3. The organics were washed with water, saturated NaCl, dried over Na2SO4, and concentrated in vacuo. The r... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Hydrazine.Hydrazine.Carboxylic acid.Thiourea | null | null | c1nn2cnnc2s1 | c1ccsc1.c1ccc2c(c1)OCO2.c1nn2cnnc2s1 | HCl | CO.C(Cl)Cl.[Cl-] | 170 | null | NNC(=S)NN.O=C(Cl)c1cccs1.O=C(O)Cc1ccc2c(c1)OCO2>CO.C(Cl)Cl.[Cl-]>c1csc(-c2nn3c(Cc4ccc5c(c4)OCO5)nnc3s2)c1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-6fb4034ab5794639bdf2ce1d1d5c13ae | Clc1ccc(Cl)nn1.NN>>NNc1ccc(Cl)nn1 | ClC=1N=NC(=CC1)Cl.O.NN>>ClC1=CC=C(N=N1)NN | Cl[c:3]1[cH:4][cH:5][c:6]([Cl:7])[n:8][n:9]1.[NH2:1][NH2:2]>>[NH2:1][NH:2][c:3]1[cH:4][cH:5][c:6]([Cl:7])[n:8][n:9]1 | Clc1ccc(Cl)nn1.NN | NNc1ccc(Cl)nn1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | da6d0a7a0f6287d8630681ac22198877e07ef33a63b1099344ef9fd19f122524 | 61806bbf8bb8981e140ee503663af0ef0e69dc4f34f6582f974a2e4218f7da88 | c1ccnnc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.[N;D1;H2:7]-[NH2;D1;+0:8]>>[N;D1;H2:7]-[NH;D2;+0:8]-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1 | null | [] | null | null | null | null | As shown in FIG. 5, a mixture of 40 g (0.27 mole) of 3,6-dichloropyridazine and 40 mL of 80% hydrazine hydrate in 80 mL of ethanol was refluxed for one hour. The reaction mixture was evaporated to dryness and the residue was recrystallized from benzene to give 39 g of 1-(6-chloropyridazin-3-yl)hydrazine (compound 1003)... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Aromatic halide | Hydrazine | c1ccnnc1 | c1ccnnc1 | c1ccnnc1 | HCl | C(C)O | null | null | Clc1ccc(Cl)nn1.NN>C(C)O>NNc1ccc(Cl)nn1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-f73031f7960e4bc48e15cd4b6620dfa1 | Clc1ccc(-c2ccccc2)nn1.NN>>NNc1ccc(-c2ccccc2)nn1 | CCOCC.ClC=1N=NC(=CC1)C1=CC=CC=C1.ClC=1N=NC(=CC1)C1=CC=CC=C1.O.NN>>C1(=CC=CC=C1)C1=CC=C(N=N1)NN | Cl[c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[n:13][n:14]1.[NH2:1][NH2:2]>>[NH2:1][NH:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[n:13][n:14]1 | Clc1ccc(-c2ccccc2)nn1.NN | NNc1ccc(-c2ccccc2)nn1 | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | OtherReaction | da6d0a7a0f6287d8630681ac22198877e07ef33a63b1099344ef9fd19f122524 | 61806bbf8bb8981e140ee503663af0ef0e69dc4f34f6582f974a2e4218f7da88 | c1ccc(-c2cccnn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.[N;D1;H2:7]-[NH2;D1;+0:8]>>[N;D1;H2:7]-[NH;D2;+0:8]-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1 | null | [] | null | null | null | null | As shown in FIG. 7, a mixture of 3-chloro-6-phenylpyridazine (compound 1006, 1 g, 5.3 mmol) and hydrazine monohydrate (0.51 mL, 10.53 mmol) in isopropanol was microwaved at 180° C. for 30 minutes. The reaction was treated with ether, the resulting precipitate filtered and washed with ether to yield 1-(6-phenylpyridazin... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Aromatic halide | Hydrazine | c1ccnnc1 | c1ccnnc1 | c1ccnnc1.c1ccccc1 | HCl | C(C)(C)O | null | null | Clc1ccc(-c2ccccc2)nn1.NN>C(C)(C)O>NNc1ccc(-c2ccccc2)nn1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-0eb0e0597917431581e6ff8309ee50c2 | O=C(O)c1cnc(Br)s1>>NC(=O)c1cnc(Br)s1 | BrC=1SC(=CN1)C(=O)O.CCN(C(C)C)C(C)C>>BrC=1SC(=CN1)C(=O)N | O[C:2](=[O:3])[c:4]1[cH:5][n:6][c:7]([Br:8])[s:9]1>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][n:6][c:7]([Br:8])[s:9]1 | O=C(O)c1cnc(Br)s1 | NC(=O)c1cnc(Br)s1 | null | null | null | Functional Group Interconversion | OtherReaction | e1b1a1f71ee10336b9e90a021457b106dbfe08a22161aaad6804675a8134a46f | 5d384be3554a01fd49be5eb779c3b10075a4cc9a2373eb20aaa867286d4e28a9 | c1cscn1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#16;a:4]:[c:5]:[#7;a:6]:[c:7]:1>>[N;D1;H2:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#16;a:4]:[c:5]:[#7;a:6]:[c:7]:1 | null | [] | null | null | null | null | Scheme 1 illustrates the synthesis of compounds of Formula 4 and 5. 2-Bromo-thiazol-5-carboxylic acid 1 is reacted with amine 2 in the presence of DMC and DIEA to afford 2-bromo-thiazol-5-carboxamide 3, which without separation is treated with arylboronic acid under Suzuki coupling conditions to give 2-aryl-thiozol-5-c... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | c1cscn1 | null | null | null | null | O=C(O)c1cnc(Br)s1>>NC(=O)c1cnc(Br)s1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-4d92171a582840429dbb0306b8c4e10e | O=C(O)c1c[nH]c(Cl)n1>>NC(=O)c1c[nH]c(Cl)n1 | ClC=1NC=C(N1)C(=O)O.CCN(C(C)C)C(C)C>>ClC=1NC=C(N1)C(=O)N | O[C:2](=[O:3])[c:4]1[cH:5][nH:6][c:7]([Cl:8])[n:9]1>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][nH:6][c:7]([Cl:8])[n:9]1 | O=C(O)c1c[nH]c(Cl)n1 | NC(=O)c1c[nH]c(Cl)n1 | null | null | null | Functional Group Interconversion | OtherReaction | e1b1a1f71ee10336b9e90a021457b106dbfe08a22161aaad6804675a8134a46f | 5d384be3554a01fd49be5eb779c3b10075a4cc9a2373eb20aaa867286d4e28a9 | c1c[nH]cn1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1>>[N;D1;H2:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1 | null | [] | null | null | null | null | Scheme 2 illustrates the synthesis of compounds 9 and 10. Lithiation of compound 6 with n-BuLi followed by the addition of carbon dioxide affords 2-chloro-imidazole-4-carboxylic acid 7. Reaction of acid 7 with amine 2 in the presence of DMC and DIEA furnishes 2-chloro-imidazole-4-carboxamide 8, which undergoes Suzuki c... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | c1c[nH]cn1 | null | null | null | null | O=C(O)c1c[nH]c(Cl)n1>>NC(=O)c1c[nH]c(Cl)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-cf0db1431780443d91e0f14adfb30a9a | Cc1nc(-c2cccc3ccccc23)sc1C(=O)N1CCN(C(C)C)CC1>>Cc1nc(-c2cccc3ccccc23)sc1CN1CCN(C(C)C)CC1 | C(C)(C)N1CCN(CC1)C(=O)C1=C(N=C(S1)C1=CC=CC2=CC=CC=C12)C.C1(=CC=CC=C1)C>>C(C)(C)N1CCN(CC1)CC1=C(N=C(S1)C1=CC=CC2=CC=CC=C12)C | O=[C:17]([c:16]1[c:2]([CH3:1])[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]23)[s:15]1)[N:18]1[CH2:19][CH2:20][N:21]([CH:22]([CH3:23])[CH3:24])[CH2:25][CH2:26]1>>[CH3:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]23)[s:15][c:16]1[CH2:17][N:18]1[CH2:19]... | Cc1nc(-c2cccc3ccccc23)sc1C(=O)N1CCN(C(C)C)CC1 | Cc1nc(-c2cccc3ccccc23)sc1CN1CCN(C(C)C)CC1 | null | null | C1CCOC1 | Reduction | Reduction of tertiary amides to amines | f74c5a050b269ec4da3871c266f01344b7447381f47cda744f8b1e9c225ae62d | c8f3c617792f7a4fae96b8a97dc0ce23461ab85d8a738fe6caacff776ef51ffa | c1ccc2c(-c3ncc(CN4CCNCC4)s3)cccc2c1 | O=[C;H0;D3;+0:1](-[#7:2](-[C:3])-[C:4])-[c:5]1:[#16;a:6]:[c:7]:[#7;a:8]:[c:9]:1-[C;D1;H3:10]>>[C:3]-[#7:2](-[CH2;D2;+0:1]-[c:5]1:[#16;a:6]:[c:7]:[#7;a:8]:[c:9]:1-[C;D1;H3:10])-[C:4] | null | [] | null | null | 8 | HOUR | To a solution of (4-isopropyl-piperazin-1-yl)-(4-methyl-2-naphthalen-1-yl-thiazol-5-yl)-methanone (25 mg, 0.066 mmol) in anhydrous THF (2.5 ml) is added a solution of alane-dimethylethylamine complex in toluene (0.5 M, 0.4 ml, 0.2 mmol, 3.0 eq.) dropwise at 0° C. The resulting mixture is stirred at rt overnight. The re... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | null | null | null | c1cscn1.c1ccc2ccccc2c1.C1C[NH]CC[NH]1 | Other | C1CCOC1 | null | 8 | Cc1nc(-c2cccc3ccccc23)sc1C(=O)N1CCN(C(C)C)CC1>C1CCOC1>Cc1nc(-c2cccc3ccccc23)sc1CN1CCN(C(C)C)CC1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-1c2f61fb48db41e3902576a0f542c4cc | CC(C)N1CCNCC1.Cn1c(C(=O)O)cnc1Cl>>CC(C)N1CCN(C(=O)c2cnc(Cl)n2C)CC1 | ClC1=NC=C(N1C)C(=O)O.C(C)(C)N1CCNCC1.[Cl-].ClC1[NH+](CCN1C)C>>ClC1=NC=C(N1C)C(=O)N1CCN(CC1)C(C)C | [CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][NH:7][CH2:17][CH2:18]1.O[C:8](=[O:9])[c:10]1[cH:11][n:12][c:13]([Cl:14])[n:15]1[CH3:16]>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][N:7]([C:8](=[O:9])[c:10]2[cH:11][n:12][c:13]([Cl:14])[n:15]2[CH3:16])[CH2:17][CH2:18]1 | CC(C)N1CCNCC1.Cn1c(C(=O)O)cnc1Cl | CC(C)N1CCN(C(=O)c2cnc(Cl)n2C)CC1 | null | null | CCOC(=O)C.CCN(C(C)C)C(C)C.C1(=CC=CC=C1)C | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | be4b86020a065d99e289e528d425e25dd0737bea0f2fd81bb05a4d03f92a7d75 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1cnc[nH]1)N1CCNCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:1-[C;D1;H3:8].[#7:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[C;D1;H3:8]-[#7;a:7]1:[c:6]:[#7;a:5]:[c:4]:[c:3]:1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:12]1-[C:11]-[C:10]-[#7:9]-[C:14]-[C:13]-1 | null | [] | null | null | 2 | HOUR | Under nitrogen, 2-chloro-3-methyl-3H-imidazole-4-carboxylic acid (0.161 g, 1.0 mmol) is dissolved in toluene (5 mL, anhydrous) and DIEA (0.26 mL). N-isopropylpiperazine (0.2 M in toluene; 5.5 mL; 1.1 mmol) is added followed by the slow addition of 2-chloro-1,3-dimethylimidazolinium chloride (0.3 M in acetonitrile; 4.0 ... | 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.c1c[nH]cn1 | HO- | CCOC(=O)C.CCN(C(C)C)C(C)C.C1(=CC=CC=C1)C | null | 2 | CC(C)N1CCNCC1.Cn1c(C(=O)O)cnc1Cl>CCOC(=O)C.CCN(C(C)C)C(C)C.C1(=CC=CC=C1)C>CC(C)N1CCN(C(=O)c2cnc(Cl)n2C)CC1 |
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