dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-64944cf17aa64cdebc9af802cb619959 | Nc1ccc(C(F)(F)F)c(OCCN2CCCC2)c1.O=C(Cl)c1cccnc1Cl>>O=C(Nc1ccc(C(F)(F)F)c(OCCN2CCCC2)c1)c1cccnc1Cl | N1(CCCC1)CCOC=1C=C(C=CC1C(F)(F)F)N.ClC1=NC=CC=C1C(=O)Cl.C(=O)(OC(C)(C)C)N1CCC(CC1)OC1=CC(=CC(=C1)C(F)(F)F)NC(=O)C=1C(=NC=CC1)Cl>>ClC1=C(C(=O)NC2=CC(=C(C=C2)C(F)(F)F)OCCN2CCCC2)C=CC=N1 | [NH2:3][c:4]1[cH:5][cH:6][c:7]([C:8]([F:9])([F:10])[F:11])[c:12]([O:13][CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][CH2:19][CH2:20]2)[cH:21]1.Cl[C:2](=[O:1])[c:22]1[cH:23][cH:24][cH:25][n:26][c:27]1[Cl:28]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([C:8]([F:9])([F:10])[F:11])[c:12]([O:13][CH2:14][CH2:15][N:16]2[CH2:17][CH2:... | Nc1ccc(C(F)(F)F)c(OCCN2CCCC2)c1.O=C(Cl)c1cccnc1Cl | O=C(Nc1ccc(C(F)(F)F)c(OCCN2CCCC2)c1)c1cccnc1Cl | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1cccc(OCCN2CCCC2)c1)c1cccnc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[Cl;D1;H0:6]):[#7;a:7]:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[Cl;D1;H0:6]-[c:5](:[#7;a:7]:[c:8]):[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:4] | null | [] | null | null | null | null | 2-Chloro-N-[3-(2-pyrrolidin-1-yl-ethoxy)-4-trifluoromethyl-phenyl]-nicotinamide was prepared from 3-(2-pyrrolidin-1-yl-ethoxy)-4-trifluoromethyl-phenylamine and 2-chloropyridine-3-carbonyl chloride by a procedure similar to that described in the preparation of 1-Boc-4-{3-[(2-chloro-pyridine-3-carbonyl)-amino]-5-trifluo... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC[NH]C1.c1ccncc1 | HCl | null | null | null | Nc1ccc(C(F)(F)F)c(OCCN2CCCC2)c1.O=C(Cl)c1cccnc1Cl>>O=C(Nc1ccc(C(F)(F)F)c(OCCN2CCCC2)c1)c1cccnc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1bf442d882d84263a5729386042fb047 | CC(=O)Cl.O=[N+]([O-])c1ccc(C(F)(F)C(F)(F)F)c(OCC(O)CN2CCCC2)c1>>CC(=O)OC(COc1cc([N+](=O)[O-])ccc1C(F)(F)C(F)(F)F)CN1CCCC1 | C(C)(=O)Cl.[N+](=O)([O-])C=1C=CC(=C(OCC(CN2CCCC2)O)C1)C(C(F)(F)F)(F)F.C(C)(=O)Cl>>[N+](=O)([O-])C=1C=CC(=C(OCC(CN2CCCC2)OC(C)=O)C1)C(C(F)(F)F)(F)F | Cl[C:2]([CH3:1])=[O:3].[OH:4][CH:5]([CH2:6][O:7][c:8]1[cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14][cH:15][c:16]1[C:17]([F:18])([F:19])[C:20]([F:21])([F:22])[F:23])[CH2:24][N:25]1[CH2:26][CH2:27][CH2:28][CH2:29]1>>[CH3:1][C:2](=[O:3])[O:4][CH:5]([CH2:6][O:7][c:8]1[cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14][cH:15][c:16]... | CC(=O)Cl.O=[N+]([O-])c1ccc(C(F)(F)C(F)(F)F)c(OCC(O)CN2CCCC2)c1 | CC(=O)OC(COc1cc([N+](=O)[O-])ccc1C(F)(F)C(F)(F)F)CN1CCCC1 | null | null | C(Cl)Cl | Acylation | Schotten-Baumann to ester | 27b76e29491fa7db5375755e15223de884a194f57a493147db0b5495ea981908 | d47ab90ace9b5dcd818151c10aae400dcf599f5a3476072b8dfedc474e97c335 | c1ccc(OCCCN2CCCC2)cc1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5](-[C:6])-[OH;D1;+0:7]>>[C:4]-[C:5](-[C:6])-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | null | [] | 0 | CELSIUS | 1.5 | HOUR | Dissolved 1-(5-nitro-2-pentafluoroethyl-phenoxy)-3-pyrrolidin-1-yl-propan-2-ol (3.5 g) in CH2Cl2 (15 ml) added TEA (2.55 ml) and cooled to 0° C. Acetyl chloride (781.3 μl) was added dropwise, forming a suspension. The mixture was warmed to RT and stirred for 1.5 h. Additional acetyl chloride (200 μl) was added and the ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary alcohol | Ester | null | null | c1ccccc1.C1CC[NH]C1 | HCl | C(Cl)Cl | 0 | 1.5 | CC(=O)Cl.O=[N+]([O-])c1ccc(C(F)(F)C(F)(F)F)c(OCC(O)CN2CCCC2)c1>C(Cl)Cl>CC(=O)OC(COc1cc([N+](=O)[O-])ccc1C(F)(F)C(F)(F)F)CN1CCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2739ac4cb6a240538bf9d1857db4f0be | CC(=O)OC(COc1cc(NC(=O)c2cccnc2Cl)ccc1C(F)(F)C(F)(F)F)N1CCCC1>>O=C(Nc1ccc(C(F)(F)C(F)(F)F)c(OC[C@@H](O)N2CCCC2)c1)c1cccnc1Cl | ClC1=NC=CC=C1C(=O)NC=1C=CC(=C(OCC(N2CCCC2)OC(C)=O)C1)C(C(F)(F)F)(F)F.[NH4+].[OH-]>>ClC1=C(C(=O)NC2=CC(=C(C=C2)C(C(F)(F)F)(F)F)OC[C@H](N2CCCC2)O)C=CC=N1 | CC(=O)[O:19][CH:18]([CH2:17][O:16][c:15]1[c:7]([C:8]([F:9])([F:10])[C:11]([F:12])([F:13])[F:14])[cH:6][cH:5][c:4]([NH:3][C:2](=[O:1])[c:26]2[cH:27][cH:28][cH:29][n:30][c:31]2[Cl:32])[cH:25]1)[N:20]1[CH2:21][CH2:22][CH2:23][CH2:24]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([C:8]([F:9])([F:10])[C:11]([F:12])([F:13])[F:... | CC(=O)OC(COc1cc(NC(=O)c2cccnc2Cl)ccc1C(F)(F)C(F)(F)F)N1CCCC1 | O=C(Nc1ccc(C(F)(F)C(F)(F)F)c(OC[C@@H](O)N2CCCC2)c1)c1cccnc1Cl | null | null | CO | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | d7acfb2397f2b5b2a83b3bebf3698d6d984dd716982297f62a944222c79ce234 | 19dd58e0f83625e74b4b1375d88cb4c813ee60f593d812516d14eafc4ab68dc7 | O=C(Nc1cccc(OCCN2CCCC2)c1)c1cccnc1 | C-C(=O)-[O;H0;D2;+0:1]-[CH;D3;+0:2](-[C:3]-[#8:4])-[#7:5](-[C:6])-[C:7]>>[#8:4]-[C:3]-[C@@H;D3;+0:2](-[OH;D1;+0:1])-[#7:5](-[C:6])-[C:7] | null | [] | null | null | 6 | HOUR | Acetic acid 2-{5-[(2-chloro-pyridine-3-carbonyl)-amino]-2-pentafluoroethyl-phenoxy}-1-pyrrolidin-1-yl-ethyl ester (408 mg) was dissolved in MeOH (15 ml) and NH4OH (6 ml) was added and the mixture was stirred at RT for 6 h. The reaction was concentrated in vacuo and dried under high vacuum. The residue was purified over... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Secondary alcohol | null | null | c1ccccc1.C1CC[NH]C1.c1ccncc1 | HO- | CO | null | 6 | CC(=O)OC(COc1cc(NC(=O)c2cccnc2Cl)ccc1C(F)(F)C(F)(F)F)N1CCCC1>CO>O=C(Nc1ccc(C(F)(F)C(F)(F)F)c(OC[C@@H](O)N2CCCC2)c1)c1cccnc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-374992bf30fc4fb79769954558be9984 | C=C(C)CN(Cc1ccc(OC)cc1)C(=O)c1cc([N+](=O)[O-])ccc1Br>>COc1ccc(CN2CC(C)(C)c3ccc([N+](=O)[O-])cc3C2=O)cc1 | C(=O)O[Na].CC(=O)[O-].[Na+].BrC1=C(C(=O)N(CC(=C)C)CC2=CC=C(C=C2)OC)C=C(C=C1)[N+](=O)[O-]>>COC1=CC=C(CN2C(C3=CC(=CC=C3C(C2)(C)C)[N+](=O)[O-])=O)C=C1 | Br[c:13]1[cH:14][cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20][c:21]1[C:22]([N:8]([CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:25][cH:24]1)[CH2:9][C:10]([CH3:11])=[CH2:12])=[O:23]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]2[CH2:9][C:10]([CH3:11])([CH3:12])[c:13]3[cH:14][cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH... | C=C(C)CN(Cc1ccc(OC)cc1)C(=O)c1cc([N+](=O)[O-])ccc1Br | COc1ccc(CN2CC(C)(C)c3ccc([N+](=O)[O-])cc3C2=O)cc1 | null | [N+](CC)(CC)(CC)CC.[Cl-] | CN(C)C=O | C-C Coupling | OtherReaction | 81902e9a4ea76d68ecbe1f16c6f94976c13d9a1410fef169047da81d1a80b11a | 4b186811a4930853b446d93d9faa39b267bddb9ce0b8021bda5c5a3b2bc69f0b | O=C1c2ccccc2CCN1Cc1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](=[O;D1;H0:6])-[#7:7](-[C:8])-[C:9]-[C;H0;D3;+0:10](-[C;D1;H3:11])=[CH2;D1;+0:12]):[c:13]>>[C:8]-[#7:7]1-[C:9]-[C;H0;D4;+0:10](-[C;D1;H3:11])(-[CH3;D1;+0:12])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:13])-[C:5]-1=[O;D1;H0:6] | null | [] | 70 | CELSIUS | 8 | HOUR | 2-Bromo-N-(4-methoxy-benzyl)-N-(2-methyl-allyl)-5-nitro-benzamide (23.4 mmol) was dissolved in DMF (150 ml) and Et4NCl (4.25 g), HCO2Na (1.75 g) and NaOAc (4.99 g) were added. N2 was bubbled through the solution for 10 min, then Pd(OAc)2 (490 mg) was added and the mixture was stirred overnight at 70° C. The mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Vinyl | null | c1ccccc1 | c1ccc2c(c1)CC[NH]C2 | c1ccccc1.c1ccc2c(c1)CC[NH]C2 | Br- | [N+](CC)(CC)(CC)CC.[Cl-].CN(C)C=O | 70 | 8 | C=C(C)CN(Cc1ccc(OC)cc1)C(=O)c1cc([N+](=O)[O-])ccc1Br>[N+](CC)(CC)(CC)CC.[Cl-].CN(C)C=O>COc1ccc(CN2CC(C)(C)c3ccc([N+](=O)[O-])cc3C2=O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-846a051d23364666b0b6512fdca9e3d8 | COc1ccc(CN2CC(C)(C)c3ccc([N+](=O)[O-])cc3C2=O)cc1>>CC1(C)CNC(=O)c2cc([N+](=O)[O-])ccc21 | COC1=CC=C(CN2C(C3=CC(=CC=C3C(C2)(C)C)[N+](=O)[O-])=O)C=C1.O.O=[N+]([O-])[O-].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[Ce+4].[NH4+].[NH4+]>>CC1(CNC(C2=CC(=CC=C12)[N+](=O)[O-])=O)C | COc1ccc(C[N:5]2[CH2:4][C:2]([CH3:1])([CH3:3])[c:16]3[c:8]([cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14][cH:15]3)[C:6]2=[O:7])cc1>>[CH3:1][C:2]1([CH3:3])[CH2:4][NH:5][C:6](=[O:7])[c:8]2[cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14][cH:15][c:16]21 | COc1ccc(CN2CC(C)(C)c3ccc([N+](=O)[O-])cc3C2=O)cc1 | CC1(C)CNC(=O)c2cc([N+](=O)[O-])ccc21 | null | null | CC#N | Reduction | Hydrogenolysis of tertiary amines | c9b908d33c0d2fc13d381d665dd476521c8100dd88680994048ba0ceebb8572f | 3da95258cd6a6ca6a5fed40d269eda3c543e9e67e5f33234974139a39c57d43d | O=C1NCCc2ccccc21 | C-O-c1:c:c:c(-C-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4](=[O;D1;H0:5])-[c:6]):c:c:1>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4](=[O;D1;H0:5])-[c:6] | null | [] | 0 | CELSIUS | 30 | MINUTE | 2-(4-Methoxy-benzyl)-4,4-dimethyl-7-nitro-3,4-dihydro-2H-isoquinolin-1-one (2.0 g) was dissolved in CH3CN (100 ml) and H2O (50 ml) and cooled to 0° C. CAN (9.64 g) was added and the reaction was stirred at 0° C. for 30 min, then warmed to RT and stirred for 6 h. The mixture was extracted with CH2Cl2 (2×300 ml) washed w... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Tertiary amide | Secondary amide | c1ccccc1.c1ccc2c(c1)CC[NH]C2 | c1ccc2c(c1)CCNC2 | c1ccc2c(c1)CCNC2 | HO- | CC#N | 0 | 0.5 | COc1ccc(CN2CC(C)(C)c3ccc([N+](=O)[O-])cc3C2=O)cc1>CC#N>CC1(C)CNC(=O)c2cc([N+](=O)[O-])ccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fe2d0af6e39d4802b4a666c67b527c5d | CC(C)(C)OC(=O)N1CCNCC1.O=C(O)c1cc([N+](=O)[O-])cc(C(F)(F)F)c1>>CC(C)(C)OC(=O)N1CCN(C(=O)c2cc([N+](=O)[O-])cc(C(F)(F)F)c2)CC1 | [N+](=O)([O-])C=1C=C(C(=O)O)C=C(C1)C(F)(F)F.C(=O)(OC(C)(C)C)N1CCNCC1.C=1C=CC2=C(C1)N=NN2O.CCN(C(C)C)C(C)C>>C(=O)(OC(C)(C)C)N1CCN(CC1)C(=O)C1=CC(=CC(=C1)C(F)(F)F)[N+](=O)[O-] | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:27][CH2:28]1.O[C:12](=[O:13])[c:14]1[cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20][c:21]([C:22]([F:23])([F:24])[F:25])[cH:26]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[c:14]2[cH:15][c:16](... | CC(C)(C)OC(=O)N1CCNCC1.O=C(O)c1cc([N+](=O)[O-])cc(C(F)(F)F)c1 | CC(C)(C)OC(=O)N1CCN(C(=O)c2cc([N+](=O)[O-])cc(C(F)(F)F)c2)CC1 | null | null | C(CCl)Cl.C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | be4b86020a065d99e289e528d425e25dd0737bea0f2fd81bb05a4d03f92a7d75 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1ccccc1)N1CCNCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:10]-[C:11]-[#7:6]-[C:7]-[C:8]-1)-[c:3](:[c:4]):[c:5] | null | [] | null | null | 3 | HOUR | A mixture of 3-nitro-5-trifluoromethyl-benzoic acid (4.13 g), 4-Boc-piperazine (2.97 g), EDC (3.88 g), HOBt (2.74 g) and DIEA (3.33 ml) in CH2Cl2 (120 ml) was stirred at RT for 3 h. The mixture was diluted with CH2Cl2 (100 ml), washed with sat'd NH4Cl, dried over MgSO4, filtered and concentrated. The residue was purifi... | 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.c1ccccc1 | HO- | C(CCl)Cl.C(Cl)Cl | null | 3 | CC(C)(C)OC(=O)N1CCNCC1.O=C(O)c1cc([N+](=O)[O-])cc(C(F)(F)F)c1>C(CCl)Cl.C(Cl)Cl>CC(C)(C)OC(=O)N1CCN(C(=O)c2cc([N+](=O)[O-])cc(C(F)(F)F)c2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-05fa8244d11f4dd68b38fca2543daba2 | CO.N#Cc1ccnc(Cl)c1>>COc1cc(C#N)ccn1 | N#N.CO.ClC1=NC=CC(=C1)C#N>>C(#N)C1=CC(=NC=C1)OC | [CH3:1][OH:2].Cl[c:3]1[cH:4][c:5]([C:6]#[N:7])[cH:8][cH:9][n:10]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]#[N:7])[cH:8][cH:9][n:10]1 | CO.N#Cc1ccnc(Cl)c1 | COc1cc(C#N)ccn1 | null | null | O1CCOCC1.CO | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 6338204ceff75e04ab34e19d98f9f9f4889f0e9f23e350d28a3d8091384c4bfe | 23dafde907f7a74dc1d4cc65967b00a9b318897fe61a3d3c4a9fddf320485f17 | c1ccncc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[OH;D1;+0:7]>>[C;D1;H3:6]-[O;H0;D2;+0:7]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | null | [] | 10 | CELSIUS | null | null | Under a stream of N2 and with cooling, Na metal (2.7 g) was added to MeOH (36 ml) with a considerable exotherm. After the Na is dissolved, a solution of 2-chloro-4-cyanopyridine (15 g) in dioxane:MeOH (1:1, 110 ml) was added via dropping funnel over a 10 min period. The reaction was heated to reflux for 3.5 h then cool... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Methanol | Ether | c1ccncc1 | c1ccncc1 | c1ccncc1 | HCl | O1CCOCC1.CO | 10 | null | CO.N#Cc1ccnc(Cl)c1>O1CCOCC1.CO>COc1cc(C#N)ccn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-333c0020076d414b9337ae242c4eba75 | COc1cc(C#N)ccn1>>COc1cc(CN)ccn1 | C(#N)C1=CC(=NC=C1)OC.Cl.CCOCC>>COC1=NC=CC(=C1)CN | [CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]#[N:7])[cH:8][cH:9][n:10]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][NH2:7])[cH:8][cH:9][n:10]1 | COc1cc(C#N)ccn1 | COc1cc(CN)ccn1 | null | [Pd] | CO | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | c1ccncc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1>>[NH2;D1;+0:1]-[CH2;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1 | null | [] | null | null | 8 | HOUR | 4-Cyano-2-methoxypyridine (1.7 g) was dissolved in MeOH (50 ml) and conc. HCl (4.96 ml) was added. Pd/C (10%) was added and H2 was added and let stand overnight. The solids were filtered through Celite® and the cake was washed with MeOH (˜250 ml). Concentration in vacuo produced an oil which was dissolved in MeOH (˜20 ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccncc1 | null | [Pd].CO | null | 8 | COc1cc(C#N)ccn1>[Pd].CO>COc1cc(CN)ccn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a4cbbdc887974a06bd7b11a541cdc418 | CC1(C)NS(=O)(=O)c2ccccc21.O=[N+]([O-])[O-]>>CC1(C)NS(=O)(=O)c2cc([N+](=O)[O-])ccc21 | CC1(NS(C2=C1C=CC=C2)(=O)=O)C.[N+](=O)([O-])[O-].[K+]>>CC1(NS(C2=C1C=CC(=C2)[N+](=O)[O-])(=O)=O)C | [CH3:1][C:2]1([CH3:3])[NH:4][S:5](=[O:6])(=[O:7])[c:8]2[cH:9][cH:10][cH:14][cH:15][c:16]21.[O-][N+:11](=[O:12])[O-:13]>>[CH3:1][C:2]1([CH3:3])[NH:4][S:5](=[O:6])(=[O:7])[c:8]2[cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14][cH:15][c:16]21 | CC1(C)NS(=O)(=O)c2ccccc21.O=[N+]([O-])[O-] | CC1(C)NS(=O)(=O)c2cc([N+](=O)[O-])ccc21 | null | null | OS(=O)(=O)O | Functional Group Addition | Aromatic nitration with NO3 salt | 97a583513da459c317b406e15b7dc86b451aa5dacc9085eddac74b29cefabc08 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | O=S1(=O)NCc2ccccc21 | [#16:1]-[c:2]:[c:3]:[cH;D2;+0:4]:[c:5]:[c:6].[O-]-[N+;H0;D3:7](-[O;-;D1;H0:8])=[O;D1;H0:9]>>[#16:1]-[c:2]:[c:3]:[c;H0;D3;+0:4](-[N+;H0;D3:7](-[O;-;D1;H0:8])=[O;D1;H0:9]):[c:5]:[c:6] | null | [] | 0 | CELSIUS | 15 | MINUTE | 3,3-Dimethyl-2,3-dihydro-benzo[d]isothiazole 1,1-dioxide was added to KNO3 in H2SO4 cooled to 0° C. and stirred for 15 min. The reaction was warmed to RT and stirred overnight. The mix was poured into ice and extracted with EtOAc (3×), washed with H2O and brine, dried and evaporated to give the compound which was used ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccc2c(c1)CNS2 | c1ccc2c(c1)CNS2 | c1ccc2c(c1)CNS2 | HO- | OS(=O)(=O)O | 0 | 0.25 | CC1(C)NS(=O)(=O)c2ccccc21.O=[N+]([O-])[O-]>OS(=O)(=O)O>CC1(C)NS(=O)(=O)c2cc([N+](=O)[O-])ccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-987f7011161a48928cef5d362896bdcc | C1CCNC1.CC(C)(C)c1ccc([N+](=O)[O-])cc1C=CCC=O>>CC(C)(C)c1ccc([N+](=O)[O-])cc1C=CCCN1CCCC1 | C(=O)(O)[O-].[Na+].C(C)(C)(C)C1=C(C=C(C=C1)[N+](=O)[O-])C=CCC=O.N1CCCC1.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+].[OH-].[Na+]>>C(C)(C)(C)C1=C(C=C(C=C1)[N+](=O)[O-])C=CCCN1CCCC1 | [NH:18]1[CH2:19][CH2:20][CH2:21][CH2:22]1.O=[CH:17][CH2:16][CH:15]=[CH:14][c:13]1[c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][c:13]1[CH:14]=[CH:15][CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][CH2:2... | C1CCNC1.CC(C)(C)c1ccc([N+](=O)[O-])cc1C=CCC=O | CC(C)(C)c1ccc([N+](=O)[O-])cc1C=CCCN1CCCC1 | null | null | CC(=O)O.CCOCC.C1CCOC1 | Functional Group Addition | reductive amination | 4b0464b8bdaac7dde88d1184d3be1de4a35ab751835dcaaf01477df10f8d9149 | 84ebf31470f3651eb1fb0a5d6346e9d00fe2543713c1f1628962e49da25ec1b1 | C(=Cc1ccccc1)CCN1CCCC1 | O=[CH;D2;+0:1]-[C:2]-[C:3]=[C:4]-[c:5].[C:6]1-[C:7]-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[c:5]-[C:4]=[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:10]1-[C:6]-[C:7]-[C:8]-[C:9]-1 | null | [] | null | null | 8 | HOUR | 4-(2-tert-Butyl-5-nitro-phenyl)-but-3-enal (895 mg) was dissolved in 40 ml THF, and to the solution was added pyrrolidine (0.317 ml). To the deep orange solution was added NaBH(OAc)3 (1.151 g) and glacial AcOH (0.207 ml). The reaction was stirred at RT overnight, then treated with saturated aqueous NaHCO3 and diluted w... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1 | Other | CC(=O)O.CCOCC.C1CCOC1 | null | 8 | C1CCNC1.CC(C)(C)c1ccc([N+](=O)[O-])cc1C=CCC=O>CC(=O)O.CCOCC.C1CCOC1>CC(C)(C)c1ccc([N+](=O)[O-])cc1C=CCCN1CCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b63a933efb3c4807aa4292153839ce87 | CC(C)(C)OC(=O)N1CC(CO)C1.CS(=O)(=O)Cl>>CC(C)(C)OC(=O)N1CC(COS(C)(=O)=O)C1 | C(=O)(OC(C)(C)C)N1CC(C1)CO.CS(=O)(=O)Cl>>C(=O)(OC(C)(C)C)N1CC(C1)COS(=O)(=O)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([CH2:11][OH:12])[CH2:17]1.Cl[S:13]([CH3:14])(=[O:15])=[O:16]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([CH2:11][O:12][S:13]([CH3:14])(=[O:15])=[O:16])[CH2:17]1 | CC(C)(C)OC(=O)N1CC(CO)C1.CS(=O)(=O)Cl | CC(C)(C)OC(=O)N1CC(COS(C)(=O)=O)C1 | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | C1CNC1 | 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 | [] | null | null | 2 | HOUR | To a solution of (1-Boc-azetidin-3-yl)-methanol (1.06 g, 5.7 mmol), TEA (1.18 mL, 8.52 mmol) in CH2Cl2 at 0° C. was added MeSO2Cl (0.53 mL, 6.82 mmol) via a syringe. The reaction was warmed to RT over 2 h and stirring was continued at RT for 2 h. The white solid formed was removed by filtration and the filtrate was was... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | C1C[NH]C1 | HCl | C(Cl)Cl | null | 2 | CC(C)(C)OC(=O)N1CC(CO)C1.CS(=O)(=O)Cl>C(Cl)Cl>CC(C)(C)OC(=O)N1CC(COS(C)(=O)=O)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c8df9a89d8fd48619c9046359a2faaee | CC(=O)Cl.Nc1cc([N+](=O)[O-])ccc1Br>>CC(=O)Nc1cc([N+](=O)[O-])ccc1Br | BrC1=C(N)C=C(C=C1)[N+](=O)[O-].CCN(C(C)C)C(C)C.C(C)(=O)Cl>>BrC1=C(C=C(C=C1)[N+](=O)[O-])NC(C)=O | Cl[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12][c:13]1[Br:14]>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12][c:13]1[Br:14] | CC(=O)Cl.Nc1cc([N+](=O)[O-])ccc1Br | CC(=O)Nc1cc([N+](=O)[O-])ccc1Br | null | CN(C)C=1C=CN=CC1 | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccccc1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | 0 | CELSIUS | 3 | HOUR | 2-Bromo-5-nitroaniline (10 g) was dissolved in 500 mL of CH2Cl2, DIEA (6.6 g) was added to the mixture, followed by DMAP (100 mg). The mixture was cooled to 0° C. in ice bath. Acetyl chloride (4 g in 50 mL CH2Cl2) was added dropwise to the reaction mixture. After the mixture was stirred at RT over 3 h, extracted once w... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1 | HCl | CN(C)C=1C=CN=CC1.C(Cl)Cl | 0 | 3 | CC(=O)Cl.Nc1cc([N+](=O)[O-])ccc1Br>CN(C)C=1C=CN=CC1.C(Cl)Cl>CC(=O)Nc1cc([N+](=O)[O-])ccc1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cd637d6bf2b4458493c8bead9ac43302 | CC(C)(C)c1ccc([N+](=O)[O-])cc1Br.CN1CCNCC1>>CN1CCN(c2cc(C(C)(C)C)c(Br)cc2[N+](=O)[O-])CC1 | C(C)(C)(C)C1=C(C=C(C=C1)[N+](=O)[O-])Br.CN1CCNCC1>>BrC1=CC(=C(C=C1C(C)(C)C)N1CCN(CC1)C)[N+](=O)[O-] | [cH:6]1[cH:7][c:8]([C:9]([CH3:10])([CH3:11])[CH3:12])[c:13]([Br:14])[cH:15][c:16]1[N+:17](=[O:18])[O-:19].[CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:20][CH2:21]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][c:8]([C:9]([CH3:10])([CH3:11])[CH3:12])[c:13]([Br:14])[cH:15][c:16]2[N+:17](=[O:18])[O-:19])[CH2:20][CH2:21]1 | CC(C)(C)c1ccc([N+](=O)[O-])cc1Br.CN1CCNCC1 | CN1CCN(c2cc(C(C)(C)C)c(Br)cc2[N+](=O)[O-])CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 65c7628a30ef9f3fded28f59cb5f1d9ebea2950b8ee6c056ed6e3d894a15700b | 7cc25fba33369069673bac5bd8fc404dc064da8d6c8cf4a77f21f4df0a617fe3 | c1ccc(N2CCNCC2)cc1 | [#7;+:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[#7;+:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1):[c:5]:[c:6] | null | [] | 130 | CELSIUS | null | null | A mixture of 1-(tert-butyl)-2-bromo-4-nitrobenzene (3 g) and N-methylpiperazine (8 g) was heated neat at 130° C. for 4 h. The residue was purified by column chromatography to give 1-[4-bromo-5-(tert-butyl)-2-nitrophenyl]-4-methylpiperazine, which was hydrogenated to furnish 4-(tert-butyl)-2-(4-methylpiperazinyl)-phenyl... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Tertiary amine | c1ccccc1.C1C[NH]CCN1 | C1C[NH]CC[NH]1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1 | null | null | 130 | null | CC(C)(C)c1ccc([N+](=O)[O-])cc1Br.CN1CCNCC1>>CN1CCN(c2cc(C(C)(C)C)c(Br)cc2[N+](=O)[O-])CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6094ea26b46440a49237506973f29032 | CC(C)(C)c1ccc(O)c([N+](=O)[O-])c1.CN(C)CCO>>CN(C)CCOc1ccc(C(C)(C)C)cc1[N+](=O)[O-] | CCOC(=O)/N=N/C(=O)OCC.[N+](=O)([O-])C1=C(C=CC(=C1)C(C)(C)C)O.CN(CCO)C.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3>>C(C)(C)(C)C1=CC(=C(OCCN(C)C)C=C1)[N+](=O)[O-] | [OH:6][c:7]1[cH:8][cH:9][c:10]([C:11]([CH3:12])([CH3:13])[CH3:14])[cH:15][c:16]1[N+:17](=[O:18])[O-:19].O[CH2:5][CH2:4][N:2]([CH3:1])[CH3:3]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([C:11]([CH3:12])([CH3:13])[CH3:14])[cH:15][c:16]1[N+:17](=[O:18])[O-:19] | CC(C)(C)c1ccc(O)c([N+](=O)[O-])c1.CN(C)CCO | CN(C)CCOc1ccc(C(C)(C)C)cc1[N+](=O)[O-] | null | null | CCOC(=O)C.C1CCOC1 | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccccc1 | O-[CH2;D2;+0:1]-[C:2]-[#7:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | 1 | HOUR | DEAD (2.6 ml) was added to a mixture of 2-nitro-4-tert-butylphenol (2 g) and N,N-dimethylethanolamine (1.3 g) and Ph3P (4 g) in THF (50 ml). The reaction was stirred at RT for 1 h, diluted with EtOAc (50 ml) and washed with 1 N HCl twice. The aqueous layer was basified with NaHCO3, extracted with EtOAc twice and washed... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccccc1 | HO- | CCOC(=O)C.C1CCOC1 | null | 1 | CC(C)(C)c1ccc(O)c([N+](=O)[O-])c1.CN(C)CCO>CCOC(=O)C.C1CCOC1>CN(C)CCOc1ccc(C(C)(C)C)cc1[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5dbe9bdbb2cd4473a7e80518da7d60af | CC(=O)Cl.Nc1cc([N+](=O)[O-])ccc1Br>>CC(=O)Nc1cc([N+](=O)[O-])ccc1Br | BrC1=C(N)C=C(C=C1)[N+](=O)[O-].CCN(C(C)C)C(C)C.C(C)(=O)Cl>>BrC1=C(C=C(C=C1)[N+](=O)[O-])NC(C)=O | Cl[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12][c:13]1[Br:14]>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12][c:13]1[Br:14] | CC(=O)Cl.Nc1cc([N+](=O)[O-])ccc1Br | CC(=O)Nc1cc([N+](=O)[O-])ccc1Br | null | CN(C)C=1C=CN=CC1 | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccccc1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | 0 | CELSIUS | 3 | HOUR | 2-Bromo-5-nitroaniline (10 g) was dissolved in CH2Cl2 (500 mL), DIEA (6.6 g) was added to the mixture, followed by 100 mg of DMAP. The mixture was cooled to 0° C. in ice bath. Acetyl chloride (4 g in 50 mL CH2Cl2) was added dropwise to the reaction mixture, which was then stirred at RT over 3 h, and extracted once with... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1 | HCl | CN(C)C=1C=CN=CC1.C(Cl)Cl | 0 | 3 | CC(=O)Cl.Nc1cc([N+](=O)[O-])ccc1Br>CN(C)C=1C=CN=CC1.C(Cl)Cl>CC(=O)Nc1cc([N+](=O)[O-])ccc1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-95332bff482142bf9d8c628ea4eaf984 | CN1CCC(c2ccccc2)CC1.O=[N+]([O-])O>>CN1CCC(c2ccc([N+](=O)[O-])cc2)CC1 | [OH-].[Na+].CN1CCC(CC1)C1=CC=CC=C1.OS(=O)(=O)O.OS(=O)(=O)O.[N+](=O)(O)[O-]>>CN1CCC(CC1)C1=CC=C(C=C1)[N+](=O)[O-] | [CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([c:6]2[cH:7][cH:8][cH:9][cH:13][cH:14]2)[CH2:15][CH2:16]1.O[N+:10](=[O:11])[O-:12]>>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([c:6]2[cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][cH:14]2)[CH2:15][CH2:16]1 | CN1CCC(c2ccccc2)CC1.O=[N+]([O-])O | CN1CCC(c2ccc([N+](=O)[O-])cc2)CC1 | null | null | null | Functional Group Addition | Aromatic nitration with HNO3 | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccc(C2CCNCC2)cc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]>>[O;-;D1;H0:2]-[N+;H0;D3:1](=[O;D1;H0:3])-[c;H0;D3;+0:6](:[c:5]:[c:4]):[c:7]:[c:8] | null | [] | 0 | CELSIUS | 3 | HOUR | To 1-methyl-4-phenylpiperidine (2.663 g, 15.19 mmol) was added carefully H2SO4 (15.2 ml). The reaction was cooled in an ice bath and a solution of H2SO4 (1.66 ml) and fuming HNO3 (0.67 ml, 15.95 mmol) was added dropwise over 45 min. The mix was stirred at 0° C. for 3 h then at RT for 1.5 h before being poured over abou... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | C1CC[NH]CC1.c1ccccc1 | HO- | null | 0 | 3 | CN1CCC(c2ccccc2)CC1.O=[N+]([O-])O>>CN1CCC(c2ccc([N+](=O)[O-])cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e687a9f79e8a489cbcb5bdf12ac42fc7 | Clc1ccccc1.Nc1ccccn1>>c1cnc2ncccc2c1 | C(Cl)Cl.NC1=NC=CC=C1.[Al+3].[Cl-].[Cl-].[Cl-].ClC1=CC=CC=C1>>N1=CC=CC2=CC=CN=C12 | Clc1c[cH:2][cH:1][cH:10]c1.[NH2:3][c:4]1[n:5][cH:6][cH:7][cH:8][cH:9]1>>[cH:1]1[cH:2][n:3][c:4]2[n:5][cH:6][cH:7][cH:8][c:9]2[cH:10]1 | Clc1ccccc1.Nc1ccccn1 | c1cnc2ncccc2c1 | null | null | CO | Miscellaneous | OtherReaction | 652be29f30782eb6e60a43469e027df9d242ff3ac9e4f15647698937f13a3f03 | 8c96956ee1b46427f2dc5deedc6348f5ebf66c2633f8506c6d1e777b1e56830f | c1cnc2ncccc2c1 | Cl-c1:c:[cH;D2;+0:1]:[c:2]:[cH;D2;+0:3]:c:1.[NH2;D1;+0:4]-[c:5]1:[#7;a:6]:[c:7]:[c:8]:[c:9]:[cH;D2;+0:10]:1>>[#7;a:6]1:[c:7]:[c:8]:[c:9]:[c;H0;D3;+0:10]2:[cH;D2;+0:1]:[c:2]:[cH;D2;+0:3]:[n;H0;D2;+0:4]:[c:5]:1:2 | null | [] | 120 | CELSIUS | null | null | To a mixture of aminopyridine (1.12 g, 5.833 mmol) and AlCl3 (3.11 g, 0.023 mol) was added chlorobenzene (10.0 mL) in a sealed vessel under Ar. The reaction was sealed and heated to 120° C. for 12 h. The reaction mixture was cooled to RT and the mixture was poured over ice/HCl mixture and extracted with EtOAc (3×50.0 m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | null | c1ccccc1.c1ccncc1 | c1cnc2ncccc2c1 | c1cnc2ncccc2c1 | HCl | CO | 120 | null | Clc1ccccc1.Nc1ccccn1>CO>c1cnc2ncccc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cd960231aa4141f598b70976ce7a06ae | CC(C)(C)OC(=O)N1CCCC1CO.Nc1cccc(C(O)(C(F)(F)F)C(F)(F)F)c1>>CC(C)(C)OC(=O)N1CCCC1COC(c1cccc(N)c1)(C(F)(F)F)C(F)(F)F | NC=1C=C(C=CC1)C(C(F)(F)F)(C(F)(F)F)O.C(C)(C)(C)OC(=O)N1C(CCC1)CO.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3>>C(C)(C)(C)OC(=O)N1C(CCC1)COC(C(F)(F)F)(C(F)(F)F)C1=CC(=CC=C1)N | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][CH:12]1[CH2:13][OH:14].O[C:15]([c:16]1[cH:17][cH:18][cH:19][c:20]([NH2:21])[cH:22]1)([C:23]([F:24])([F:25])[F:26])[C:27]([F:28])([F:29])[F:30]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][CH:12]1[CH2:13][O:14... | CC(C)(C)OC(=O)N1CCCC1CO.Nc1cccc(C(O)(C(F)(F)F)C(F)(F)F)c1 | CC(C)(C)OC(=O)N1CCCC1COC(c1cccc(N)c1)(C(F)(F)F)C(F)(F)F | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Alcohol to ether | 684823df159a4c07d0a2a3c5a4e8843a8449fd560dd00a2ccbb32e95f87ee6bc | 71d6b370ca48f1d75269bb2a372b1608a88e28617e379e11884cc0e510f32096 | c1ccc(COCC2CCCN2)cc1 | O-[C;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8])-[C:9](-[F;D1;H0:10])(-[F;D1;H0:11])-[F;D1;H0:12].[#7:13]-[C:14]-[C:15]-[OH;D1;+0:16]>>[#7:13]-[C:14]-[C:15]-[O;H0;D2;+0:16]-[C;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8])-[C:9](-[F;D1;H0:10])(-[F... | null | [] | null | null | 4 | HOUR | To a mixture of 2-(3-amino-phenyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol (1.30 g), 2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (1.04 g), PPh3 (2.64 g) and molecular sieves 4 Å in THF (100 mL) was added diethyl diazocarboxylate (1.55 mL) slowly. The reaction was stirred at RT for 4 h and at reflux for ov... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Tertiary alcohol | Ether | null | null | C1CC[NH]C1.c1ccccc1 | HO- | C1CCOC1 | null | 4 | CC(C)(C)OC(=O)N1CCCC1CO.Nc1cccc(C(O)(C(F)(F)F)C(F)(F)F)c1>C1CCOC1>CC(C)(C)OC(=O)N1CCCC1COC(c1cccc(N)c1)(C(F)(F)F)C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2347aaa226ce4ef08d8a0adf853757d2 | COC(=O)C(C(F)(F)F)C(F)(F)F.O=[N+]([O-])c1ccc(F)c([N+](=O)[O-])c1>>COC(=O)C(c1ccc([N+](=O)[O-])cc1[N+](=O)[O-])(C(F)(F)F)C(F)(F)F | FC(C(C(=O)OC)C(F)(F)F)(F)F.FC(C(C(=O)OC)C(F)(F)F)(F)F.[N+](=O)([O-])C1=C(C=CC(=C1)[N+](=O)[O-])F.[F-].[K+].C1COCCOCCOCCOCCOCCO1.[F-].[K+].C1COCCOCCOCCOCCOCCO1.Cl>>COC(C(C(F)(F)F)(C(F)(F)F)C1=C(C=C(C=C1)[N+](=O)[O-])[N+](=O)[O-])=O | [CH3:1][O:2][C:3](=[O:4])[CH:5]([C:18]([F:19])([F:20])[F:21])[C:22]([F:23])([F:24])[F:25].F[c:6]1[cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][c:14]1[N+:15](=[O:16])[O-:17]>>[CH3:1][O:2][C:3](=[O:4])[C:5]([c:6]1[cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][c:14]1[N+:15](=[O:16])[O-:17])([C:18]([F:19])([F:20])[F... | COC(=O)C(C(F)(F)F)C(F)(F)F.O=[N+]([O-])c1ccc(F)c([N+](=O)[O-])c1 | COC(=O)C(c1ccc([N+](=O)[O-])cc1[N+](=O)[O-])(C(F)(F)F)C(F)(F)F | null | null | S1(=O)(=O)CCCC1.CCOCC | C-C Coupling | OtherReaction | d3d9afa5ce2f74bb34a156b067e77d0f1f2f42c891df202bc7004198f71814d0 | d10596a8c19a2f73e75b45831843b0167b833766de35d70e5c827a0edd11483e | c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[C;D1;H3:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[CH;D3;+0:11](-[C:12](-[F;D1;H0:13])(-[F;D1;H0:14])-[F;D1;H0:15])-[C:16](-[F;D1;H0:17])(-[F;D1;H0:18])-[F;D1;H0:19]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[C;H0;D4;+0:11](-[C:9](=[O;D1;H0:10])-[#8:8]-[C;D1;H3:7])(-[C:12](-[F;... | null | [] | null | null | null | null | A mixture of 7.08 g (38.07 mmol) 2,4-dinitrofluorobenzene, 2.43 g (41.88 mmol) KF, and 0.58 g (2.21 mmol) 18-crown-6-ether in 37 ml sulfolane was added 4.00 g (19.04 mmol) methyl 2-(trifluoromethyl)-3,3,3-trifluoropropionate dropwise over about 7 h via syringe pump. After the addition was complete, another 2.43 g KF, 0... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester | Ester | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | S1(=O)(=O)CCCC1.CCOCC | null | null | COC(=O)C(C(F)(F)F)C(F)(F)F.O=[N+]([O-])c1ccc(F)c([N+](=O)[O-])c1>S1(=O)(=O)CCCC1.CCOCC>COC(=O)C(c1ccc([N+](=O)[O-])cc1[N+](=O)[O-])(C(F)(F)F)C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-148057caa889414786165da4678cf2dc | CC(C)(C)OC(=O)c1ccc(C(=O)Nc2ccc(C(F)(F)C(F)(F)F)c(OCCN)c2)c(Cl)n1>>NCCOc1cc(NC(=O)c2cccnc2Cl)ccc1C(F)(F)C(F)(F)F | C(=O)(OC(C)(C)C)C1=NC(=C(C(=O)NC2=CC(=C(C=C2)C(C(F)(F)F)(F)F)OCCN)C=C1)Cl.C(=O)(C(F)(F)F)O>>NCCOC=1C=C(C=CC1C(C(F)(F)F)(F)F)NC(C1=C(N=CC=C1)Cl)=O | CC(C)(C)OC(=O)[c:14]1[cH:13][cH:12][c:11]([C:9]([NH:8][c:7]2[cH:6][c:5]([O:4][CH2:3][CH2:2][NH2:1])[c:20]([C:21]([F:22])([F:23])[C:24]([F:25])([F:26])[F:27])[cH:19][cH:18]2)=[O:10])[c:16]([Cl:17])[n:15]1>>[NH2:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][c:7]([NH:8][C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][n:15][c:16]2[Cl:17])[c... | CC(C)(C)OC(=O)c1ccc(C(=O)Nc2ccc(C(F)(F)C(F)(F)F)c(OCCN)c2)c(Cl)n1 | NCCOc1cc(NC(=O)c2cccnc2Cl)ccc1C(F)(F)C(F)(F)F | null | null | C(Cl)Cl | Reduction | Decarboxylation | d83151eaff377847401d8270d4a1ed02722bb4f23d6b015dd6b8ba5e506e80f3 | 819f23c772480c303ab85988e0c5df4366b1418d125c036e6f579b95e75e3482 | O=C(Nc1ccccc1)c1cccnc1 | C-C(-C)(-C)-O-C(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]>>[c:5]:[c:4]:[cH;D2;+0:1]:[#7;a:2]:[c:3] | null | [] | null | null | 2 | HOUR | To a solution of 500 mg (0.98 mmol) Boc-N-[3-(2-Amino-ethoxy)-4-pentafluoroethyl-phenyl]-2-chloro-nicotinamide in 10 ml CH2Cl2 was added 10 ml TFA and stirred for 2 h. The reaction was concentrated down, treated with 6N aqueous NaOH, and extracted 3 times with CH2Cl2. The combined organic extracts were dried over Na2SO... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | null | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1 | HO- | C(Cl)Cl | null | 2 | CC(C)(C)OC(=O)c1ccc(C(=O)Nc2ccc(C(F)(F)C(F)(F)F)c(OCCN)c2)c(Cl)n1>C(Cl)Cl>NCCOc1cc(NC(=O)c2cccnc2Cl)ccc1C(F)(F)C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7e8e9faa7b8948818b4f8cc9ebbef060 | CS(=O)(=O)Cl.NCCOc1cc(NC(=O)c2cccnc2Cl)ccc1C(F)(F)C(F)(F)F>>CS(=O)(=O)NCCOc1cc(NC(=O)c2cccnc2Cl)ccc1C(F)(F)C(F)(F)F | NCCOC=1C=C(C=CC1C(C(F)(F)F)(F)F)NC(C1=C(N=CC=C1)Cl)=O.CCN(CC)CC.CS(=O)(=O)Cl>>ClC1=C(C(=O)NC2=CC(=C(C=C2)C(C(F)(F)F)(F)F)OCCNS(=O)(=O)C)C=CC=N1 | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[NH2:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][c:11]([NH:12][C:13](=[O:14])[c:15]2[cH:16][cH:17][cH:18][n:19][c:20]2[Cl:21])[cH:22][cH:23][c:24]1[C:25]([F:26])([F:27])[C:28]([F:29])([F:30])[F:31]>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][c:11]([NH:12][C:13](=[O:14])[c:1... | CS(=O)(=O)Cl.NCCOc1cc(NC(=O)c2cccnc2Cl)ccc1C(F)(F)C(F)(F)F | CS(=O)(=O)NCCOc1cc(NC(=O)c2cccnc2Cl)ccc1C(F)(F)C(F)(F)F | null | null | C(Cl)Cl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C(Nc1ccccc1)c1cccnc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | null | [] | null | null | 5 | MINUTE | To a solution of 381 mg (0.93 mmol) N-[3-(2-amino-ethoxy)-4-pentafluoroethyl-phenyl]-2-chloro-nicotinamide in 10 ml CH2Cl2 at 0° C. was added 0.389 ml Et3N and 0.072 ml (0.93 mmol) methanesulfonylchloride. After 5 min, the reaction was stirred at RT for 30 min. The reaction was diluted with CH2Cl2, washed with brine, d... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccncc1 | HCl | C(Cl)Cl | null | 0.083333 | CS(=O)(=O)Cl.NCCOc1cc(NC(=O)c2cccnc2Cl)ccc1C(F)(F)C(F)(F)F>C(Cl)Cl>CS(=O)(=O)NCCOc1cc(NC(=O)c2cccnc2Cl)ccc1C(F)(F)C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8130173125e74ebd93232c434ce35ee7 | CC(C)(C)c1ccccc1N.O=[N+]([O-])[O-]>>CC(C)(C)c1ccc([N+](=O)[O-])cc1N | [N+](=O)([O-])[O-].[K+].[N+](=O)([O-])[O-].[K+].OS(=O)(=O)O.C(=O)=O.C(C)(C)(C)C1=C(N)C=CC=C1>>C(C)(C)(C)C1=C(C=C(C=C1)[N+](=O)[O-])N | [CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][cH:8][cH:12][c:13]1[NH2:14].[O-][N+:9](=[O:10])[O-:11]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][c:13]1[NH2:14] | CC(C)(C)c1ccccc1N.O=[N+]([O-])[O-] | CC(C)(C)c1ccc([N+](=O)[O-])cc1N | null | null | null | Functional Group Addition | Aromatic nitration with NO3 salt | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccccc1 | [O-]-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]>>[O;-;D1;H0:2]-[N+;H0;D3:1](=[O;D1;H0:3])-[c;H0;D3;+0:6](:[c:5]:[c:4]):[c:7]:[c:8] | null | [] | null | null | 4 | HOUR | Concentrated H2SO4 (1 L) was cooled to −10° C. with a dry ice IpOH bath in a 2 L 3-neck round bottom flask fitted with a mechanical stirrer and temperature probe. 2-t-Butylaniline (109 g, 730 mmol) was added, giving a clumpy solid. Once the temperature of the mixture was stabilized at −10° C., KNO3 (101 g, 1001 mmol) w... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | null | null | 4 | CC(C)(C)c1ccccc1N.O=[N+]([O-])[O-]>>CC(C)(C)c1ccc([N+](=O)[O-])cc1N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3275349521a845aebb3bba127c2bdeb6 | CC(C)(C)c1ccc([N+](=O)[O-])cc1N.O=C(Br)CBr>>CC(C)(C)c1ccc([N+](=O)[O-])cc1NC(=O)CBr.[NH4+].[OH-] | BrCC(=O)Br.C(C)(C)(C)C1=C(C=C(C=C1)[N+](=O)[O-])N>>[NH4+].[OH-].BrCC(=O)NC1=C(C=CC(=C1)[N+](=O)[O-])C(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][c:13]1[NH2:14].Br[C:15](=[O:16])[CH2:17][Br:18]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][c:13]1[NH:14][C:15](=[O:16])[CH2:17][Br:18].[NH4+:19].[OH-:20] | CC(C)(C)c1ccc([N+](=O)[O-])cc1N.O=C(Br)CBr | CC(C)(C)c1ccc([N+](=O)[O-])cc1NC(=O)CBr.[NH4+].[OH-] | null | CN(C)C=1C=CN=CC1 | C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccccc1 | Br-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Br;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[Br;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | 0 | CELSIUS | 8 | HOUR | 2-tert-Butyl-5-nitro-phenylamine (70 g, 359 mmol) and a catalytic amount of DMAP were dissolved in THF (1.5 L) under N2. TEA (109 g, 1077 mmol) was added and the solution was cooled to 0° C. Bromoacetyl bromide (207 g, 1023 mmol) was added and the reaction was gradually warmed to RT with stirring overnight. The reactio... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1 | Br- | CN(C)C=1C=CN=CC1.C1CCOC1 | 0 | 8 | CC(C)(C)c1ccc([N+](=O)[O-])cc1N.O=C(Br)CBr>CN(C)C=1C=CN=CC1.C1CCOC1>CC(C)(C)c1ccc([N+](=O)[O-])cc1NC(=O)CBr.[NH4+].[OH-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d7bfdbd51b8d4379a0c84f0f406b2d87 | CC(=O)N(C)C.CC(C)(C)c1ccc([N+](=O)[O-])cc1NC(=O)CBr>>CN(C)CC(=O)Nc1cc([N+](=O)[O-])ccc1C(C)(C)C | CC(=O)N(C)C.BrCC(=O)NC1=C(C=CC(=C1)[N+](=O)[O-])C(C)(C)C.C(=O)([O-])[O-].[K+].[K+]>>C(C)(C)(C)C1=C(C=C(C=C1)[N+](=O)[O-])NC(CN(C)C)=O | CC(=O)[N:2]([CH3:1])[CH3:3].Br[CH2:4][C:5](=[O:6])[NH:7][c:8]1[cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14][cH:15][c:16]1[C:17]([CH3:18])([CH3:19])[CH3:20]>>[CH3:1][N:2]([CH3:3])[CH2:4][C:5](=[O:6])[NH:7][c:8]1[cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14][cH:15][c:16]1[C:17]([CH3:18])([CH3:19])[CH3:20] | CC(=O)N(C)C.CC(C)(C)c1ccc([N+](=O)[O-])cc1NC(=O)CBr | CN(C)CC(=O)Nc1cc([N+](=O)[O-])ccc1C(C)(C)C | null | null | C1CCOC1 | Functional Group Addition | OtherReaction | c00a4a61834dab3e2d90234c4324bc0488fb3f018c4e256fb1e9464d37fa09d4 | 1028b2cce2532952dd67ffdeaa1265b5b1b75b29539e52da6580e010225db363 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5].C-C(=O)-[N;H0;D3;+0:6](-[C;D1;H3:7])-[C;D1;H3:8]>>[C;D1;H3:7]-[N;H0;D3;+0:6](-[C;D1;H3:8])-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5] | null | [] | 0 | CELSIUS | 8 | HOUR | 2-Bromo-N-(2-tert-butyl-5-nitro-phenyl)-acetamide (80 g, 253 mmol) and K2CO3 (70 g, 506 mmol) were combined in a 3-L 3-neck round bottom flask fitted with a mechanical stirrer, N2 inlet, and pressure equalizing addition funnel. THF (1.75 L) was added and the mixture was cooled to 0° C. under N2. DMA (400 mL of a 2 M so... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amide | Tertiary amine | null | null | c1ccccc1 | HBr | C1CCOC1 | 0 | 8 | CC(=O)N(C)C.CC(C)(C)c1ccc([N+](=O)[O-])cc1NC(=O)CBr>C1CCOC1>CN(C)CC(=O)Nc1cc([N+](=O)[O-])ccc1C(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-190fc46c66424648aa992b16b02def9a | CN(C)CC(=O)Nc1cc([N+](=O)[O-])ccc1C(C)(C)C>>CN(C)CC(=O)Nc1cc(N)ccc1C(C)(C)C.[NH4+].[OH-] | C(C)(C)(C)C1=C(C=C(C=C1)[N+](=O)[O-])NC(CN(C)C)=O>>[NH4+].[OH-].NC=1C=CC(=C(C1)NC(CN(C)C)=O)C(C)(C)C | O=[N+:11]([c:10]1[cH:9][c:8]([NH:7][C:5]([CH2:4][N:2]([CH3:1])[CH3:3])=[O:6])[c:14]([C:15]([CH3:16])([CH3:17])[CH3:18])[cH:13][cH:12]1)[O-:20]>>[CH3:1][N:2]([CH3:3])[CH2:4][C:5](=[O:6])[NH:7][c:8]1[cH:9][c:10]([NH2:11])[cH:12][cH:13][c:14]1[C:15]([CH3:16])([CH3:17])[CH3:18].[NH4+:19].[OH-:20] | CN(C)CC(=O)Nc1cc([N+](=O)[O-])ccc1C(C)(C)C | CN(C)CC(=O)Nc1cc(N)ccc1C(C)(C)C.[NH4+].[OH-] | null | null | O1CCOCC1.CCO | Functional Group Interconversion | Reduction of nitro groups to amines | 5c1ea979989295c14f1f65f49e58974d5c524451abca65fc2e6cec44e3d0784f | 10b8579fd1662beac4350d758bc16e1f45ee6ea295ff9572db62110c9e2a77db | c1ccccc1 | O=[N+;H0;D3:1](-[O-;H0;D1:2])-[c:3](:[c:4]):[c:5]>>[NH2;D1;+0:1]-[c:3](:[c:4]):[c:5].[OH-;D0:2] | null | [] | null | null | null | null | N-(2-tert-Butyl-5-nitro-phenyl)-2-dimethylamino-acetamide (25.8 g, 92 mmol) was dissolved in EtOH (1.4 L) and 1,4-dioxane (200 mL). The solution was degassed under vacuum with stirring. 10% Pd/C (2.5 g) was added (as a slurry in EtOH). The mixture was degassed again, then the reaction vessel was charged with H2 gas (ba... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | null | O1CCOCC1.CCO | null | null | CN(C)CC(=O)Nc1cc([N+](=O)[O-])ccc1C(C)(C)C>O1CCOCC1.CCO>CN(C)CC(=O)Nc1cc(N)ccc1C(C)(C)C.[NH4+].[OH-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ed4ff2269d8d4e07b9820f7a2427ead5 | CC(C)(C)c1ccc(N)cc1.Cn1ncc(C(=O)Cl)c1Cl>>Cn1ncc(C(=O)Nc2ccc(C(C)(C)C)cc2)c1Cl | ClC1=C(C=NN1C)C(=O)Cl.C(C)(C)(C)C1=CC=C(N)C=C1>>C(C)(C)(C)C1=CC=C(C=C1)NC(=O)C=1C=NN(C1Cl)C | [NH2:8][c:9]1[cH:10][cH:11][c:12]([C:13]([CH3:14])([CH3:15])[CH3:16])[cH:17][cH:18]1.Cl[C:6]([c:5]1[cH:4][n:3][n:2]([CH3:1])[c:19]1[Cl:20])=[O:7]>>[CH3:1][n:2]1[n:3][cH:4][c:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][c:12]([C:13]([CH3:14])([CH3:15])[CH3:16])[cH:17][cH:18]2)[c:19]1[Cl:20] | CC(C)(C)c1ccc(N)cc1.Cn1ncc(C(=O)Cl)c1Cl | Cn1ncc(C(=O)Nc2ccc(C(C)(C)C)cc2)c1Cl | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccccc1)c1cn[nH]c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5]:[#7;a:6](-[C;D1;H3:7]):[c:8]:1-[Cl;D1;H0:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C;D1;H3:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[c:8]:1-[Cl;D1;H0:9] | null | [] | 0 | CELSIUS | null | null | 5-Chloro-1-methyl-1H-pyrazole-4-carbonyl chloride (1.0 g, 5.6 mmol) was dissolved in CH2Cl2 (100 mL) under N2 and cooled to 0° C. 4-t-Butylaniline was added and the reaction was stirred with gradual warming to RT overnight. The reaction was quenched with saturated NaHCO3(aq) and extracted 3× with fresh CH2Cl2. The CH2C... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1c[nH]nc1.c1ccccc1 | HCl | C(Cl)Cl | 0 | null | CC(C)(C)c1ccc(N)cc1.Cn1ncc(C(=O)Cl)c1Cl>C(Cl)Cl>Cn1ncc(C(=O)Nc2ccc(C(C)(C)C)cc2)c1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fa0bf815759d4bbb9e78033bfb630276 | CC(C)(C)OC(=O)N1CCCC1CO.Nc1cccc(C(O)(C(F)(F)F)C(F)(F)F)c1>>CC(C)(C)OC(=O)N1CCCC1COC(c1cccc(N)c1)(C(F)(F)F)C(F)(F)F | CCOC(=O)/N=N/C(=O)OCC.NC=1C=C(C=CC1)C(C(F)(F)F)(C(F)(F)F)O.C(C)(C)(C)OC(=O)N1C(CCC1)CO.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3>>C(C)(C)(C)OC(=O)N1C(CCC1)COC(C(F)(F)F)(C(F)(F)F)C1=CC(=CC=C1)N | O[CH2:13][CH:12]1[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10][CH2:11]1.[OH:14][C:15]([c:16]1[cH:17][cH:18][cH:19][c:20]([NH2:21])[cH:22]1)([C:23]([F:24])([F:25])[F:26])[C:27]([F:28])([F:29])[F:30]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][CH:12]1[CH2:13][O:... | CC(C)(C)OC(=O)N1CCCC1CO.Nc1cccc(C(O)(C(F)(F)F)C(F)(F)F)c1 | CC(C)(C)OC(=O)N1CCCC1COC(c1cccc(N)c1)(C(F)(F)F)C(F)(F)F | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Alcohol to ether | 684823df159a4c07d0a2a3c5a4e8843a8449fd560dd00a2ccbb32e95f87ee6bc | 71d6b370ca48f1d75269bb2a372b1608a88e28617e379e11884cc0e510f32096 | c1ccc(COCC2CCCN2)cc1 | 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])-[C:12].[F;D1;H0:13]-[C:14](-[F;D1;H0:15])(-[F;D1;H0:16])-[C:17](-[OH;D1;+0:18])(-[c:19])-[C:20](-[F;D1;H0:21])(-[F;D1;H0:22])-[F;D1;H0:23]>>[C:3]-[C:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:18]-[C:17](-[c:19])(-[C:14]... | null | [] | null | null | 4 | HOUR | To a mixture of 2-(3-amino-phenyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol (1.30 g), 2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (1.04 g), PPh3 (2.64 g) and molecular sieves 4 Å in THF (100 mL) was added DEAD (1.55 mL) slowly. The reaction was stirred at RT for 4 h and at reflux overnight. After filtratio... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Tertiary alcohol | Ether | null | null | C1CC[NH]C1.c1ccccc1 | HO- | C1CCOC1 | null | 4 | CC(C)(C)OC(=O)N1CCCC1CO.Nc1cccc(C(O)(C(F)(F)F)C(F)(F)F)c1>C1CCOC1>CC(C)(C)OC(=O)N1CCCC1COC(c1cccc(N)c1)(C(F)(F)F)C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3e45c3e21dd94b99bba2fb1392809a3f | COC(=O)c1cccc([N+](=O)[O-])c1CBr.N>>O=C1NCc2c1cccc2[N+](=O)[O-] | N.COC(C1=C(C(=CC=C1)[N+](=O)[O-])CBr)=O>>[N+](=O)([O-])C1=C2CNC(C2=CC=C1)=O | CO[C:2](=[O:1])[c:6]1[c:5]([CH2:4]Br)[c:10]([N+:11](=[O:12])[O-:13])[cH:9][cH:8][cH:7]1.[NH3:3]>>[O:1]=[C:2]1[NH:3][CH2:4][c:5]2[c:6]1[cH:7][cH:8][cH:9][c:10]2[N+:11](=[O:12])[O-:13] | COC(=O)c1cccc([N+](=O)[O-])c1CBr.N | O=C1NCc2c1cccc2[N+](=O)[O-] | null | null | CO | Acylation | OtherReaction | bfe20f0aa9f011cd97f8730d82b7c7716781d101d55a13d6080c38f132dfa20e | 64fe73e2e83384d508c35f2187876b5b9badfa6118b2f44eff0dc89bfcf766e3 | O=C1NCc2ccccc21 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4](-[C;H0;D3;+0:5](=[O;D1;H0:6])-O-C):[c:7].[NH3;D0;+0:8]>>[O;D1;H0:6]=[C;H0;D3;+0:5]1-[NH;D2;+0:8]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]-1:[c:7] | null | [] | null | null | 8 | HOUR | NH3 (2.0 M in MeOH, 50 ml) was slowly added to the solution of 2-bromomethyl-3-nitro-benzoic acid methyl ester (4.46 g, contaminated with a small amount of assumed starting material, 16.3 mmol) in 30 ml of MeOH at RT. The resulting mixture was stirred at RT overnight, to provide the title compound as a white solid. MS ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Secondary amide | null | c1ccc2c(c1)CNC2 | c1ccc2c(c1)CNC2 | HBr | CO | null | 8 | COC(=O)c1cccc([N+](=O)[O-])c1CBr.N>CO>O=C1NCc2c1cccc2[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-147c8d6e742e4e01980a33cd76e0408f | Brc1ccc(Br)nc1>>N#Cc1ccc(Br)cn1 | C(Cl)Cl.CN(C)C=O.BrC1=NC=C(C=C1)Br>>BrC=1C=CC(=NC1)C#N | Br[c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][n:9]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][n:9]1 | Brc1ccc(Br)nc1 | N#Cc1ccc(Br)cn1 | null | [C-]#N.[Zn+2].[C-]#N.[Zn].C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2] | O | Miscellaneous | OtherReaction | 8bb970223fb9058022a1c0cc1f9e538de973681a8f3a5dcbab2e4e1d78c06c44 | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | c1ccncc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]>>[N;D1;H0:6]#[C:7]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | The mixture of 2,5-dibromopyridine (4.74 g, 20.0 mmol), zinc cyanide (1.40 g, 12.0 mmol), zinc dust (0.059 g, 0.90 mmol), and Pd(dppf)Cl2.CH2Cl2 (0.36 g, 0.44 mmol) in 25 ml of DMF was heated at reflux for 5 h, cooled to RT, diluted with H2O, extracted with EtOAc, the organic portion was washed with brine, the solvents... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccncc1 | c1ccncc1 | c1ccncc1 | Br- | [C-]#N.[Zn+2].[C-]#N.[Zn].C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].O | null | null | Brc1ccc(Br)nc1>[C-]#N.[Zn+2].[C-]#N.[Zn].C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].O>N#Cc1ccc(Br)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e22aeb1fbf8b4986bf1389be67c30408 | c1cnc2[nH]ccc2c1>>[O-][n+]1cccc2cc[nH]c21 | N1C=CC=2C1=NC=CC2.C(=O)(O)[O-].[Na+].OOS(=O)[O-].[K+]>>N1C=CC=2C1=[N+](C=CC2)[O-] | [n:2]1[cH:3][cH:4][cH:5][c:6]2[cH:7][cH:8][nH:9][c:10]12>>[O-:1][n+:2]1[cH:3][cH:4][cH:5][c:6]2[cH:7][cH:8][nH:9][c:10]12 | c1cnc2[nH]ccc2c1 | [O-][n+]1cccc2cc[nH]c21 | null | null | CO.O | Functional Group Interconversion | OtherReaction | b0d2d9a7d87baed5028e1aac2158ae6d43567cd5606b1e640ffac5681ed9e1ce | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1c[nH+]c2[nH]ccc2c1 | [c:1]:[c:2]:[n;H0;D2;+0:3]:[c:4](:[c:5]):[#7;a:6]:[c:7]>>[O;-;D1;H0:8]-[n+;H0;D3:3](:[c:2]:[c:1]):[c:4](:[c:5]):[#7;a:6]:[c:7] | null | [] | null | null | 5 | HOUR | To a suspension of 1H-pyrrolo[2,3-b]pyridine (10.0 g) and NaHCO3 (45.2 g) in 1:1 MeOH/H2O (1000 mL) was added Oxone® (106 g) in potions during 40 min period. The mixture was stirred at RT for 5 h. The sold was removed by filtration and the filtrate was concentrated to 200 mL in volume. This aqueous phase was extracted ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1cnc2[nH]ccc2c1 | C1=Cc2cc[nH]c2[NH+]=C1 | C1=Cc2cc[nH]c2[NH+]=C1 | null | CO.O | null | 5 | c1cnc2[nH]ccc2c1>CO.O>[O-][n+]1cccc2cc[nH]c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9b332e46ea844687a2a9c5484418ea2a | O=P(Cl)(Cl)Cl.[O-][n+]1cccc2cc[nH]c21>>Clc1ccnc2[nH]ccc12 | O=P(Cl)(Cl)Cl.N1C=CC=2C1=[N+](C=CC2)[O-].C(=O)([O-])[O-].[Na+].[Na+]>>ClC1=C2C(=NC=C1)NC=C2 | O=P(Cl)(Cl)[Cl:1].[O-][n+:5]1[cH:4][cH:3][cH:2][c:10]2[c:6]1[nH:7][cH:8][cH:9]2>>[Cl:1][c:2]1[cH:3][cH:4][n:5][c:6]2[nH:7][cH:8][cH:9][c:10]12 | O=P(Cl)(Cl)Cl.[O-][n+]1cccc2cc[nH]c21 | Clc1ccnc2[nH]ccc12 | null | null | O | Miscellaneous | OtherReaction | d849b10e304f0b95118791f0d9403cad7d7997a55f7251e1b889b670a8a00128 | a48150e9dff88baab32dd83daf5ab089c597626e3c583c33a5868d8e1353c1ea | c1cnc2[nH]ccc2c1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].[O-]-[n+;H0;D3:2]1:[c:3]:[c:4]:[cH;D2;+0:5]:[c:6]2:[c:7]:[c:8]:[#7;a:9]:[c:10]:2:1>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:5]1:[c:4]:[c:3]:[n;H0;D2;+0:2]:[c:10]2:[#7;a:9]:[c:8]:[c:7]:[c:6]:2:1 | null | [] | null | null | null | null | To a cooled POCl3 (50 mL) in a dried round bottom flask, 1H-pyrrolo[2,3-b]pyridine 7-oxide (5.73 g, step A) was added in potions. The mixture was heated to reflux for 5 h. After cooled down to RT, POCl3 was evaporated under high vacuum under gentle heating (40-50° C.) to obtain black residue. 50 mL of H2O was added slo... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | C1=Cc2cc[nH]c2[NH+]=C1 | c1cnc2[nH]ccc2c1 | c1cnc2[nH]ccc2c1 | HCl | O | null | null | O=P(Cl)(Cl)Cl.[O-][n+]1cccc2cc[nH]c21>O>Clc1ccnc2[nH]ccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8c2f457f32cd4c37b6a9944360389f3c | CC(=O)Cl.Clc1ccnc2[nH]ccc12.[I-]>>CC(=O)n1ccc2c(I)ccnc21 | ClC1=C2C(=NC=C1)NC=C2.[Na+].[I-].C(=O)([O-])[O-].[Na+].[Na+].OS(=O)[O-].[Na+].C(C)(=O)Cl>>IC1=C2C(=NC=C1)N(C=C2)C(C)=O | Cl[C:2]([CH3:1])=[O:3].Cl[c:8]1[c:7]2[cH:6][cH:5][nH:4][c:13]2[n:12][cH:11][cH:10]1.[I-:9]>>[CH3:1][C:2](=[O:3])[n:4]1[cH:5][cH:6][c:7]2[c:8]([I:9])[cH:10][cH:11][n:12][c:13]12 | CC(=O)Cl.Clc1ccnc2[nH]ccc12.[I-] | CC(=O)n1ccc2c(I)ccnc21 | null | null | CC#N | Acylation | OtherReaction | 215c33b7d08deae707733dfc55fd145a90040e852915038481692139008c137f | c5ea6d62a79b27fe6c5149b3805be569262bb0d5c2eb414ebac21dfc99ca45f2 | c1cnc2[nH]ccc2c1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].Cl-[c;H0;D3;+0:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]2:[nH;D2;+0:9]:[c:10]:[c:11]:[c:12]:2:1.[I-;H0;D0:13]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[n;H0;D3;+0:9]1:[c:10]:[c:11]:[c:12]2:[c:8]:1:[#7;a:7]:[c:6]:[c:5]:[c;H0;D3;+0:4]:2-[I;H0;D1;+0:13] | null | [] | null | null | 15 | MINUTE | To a suspension of 4-chloro-1H-pyrrolo[2,3-b]pyridine (3.80 g, step B) and NaI (19.15 g) in CH3CN (40 mL) was added acetyl chloride (5.0 mL) slowly. The mixture was heated to reflux for overnight. After cooled to RT, 40 mL of 10% Na2CO3 and 40 mL of 10% NaHSO3 were added. After stirring for 15 min, the mixture was extr... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aromatic halide | Aromatic halide | c1cnc2[nH]ccc2c1 | c1ccnc2[nH]ccc12 | c1ccnc2[nH]ccc12 | HCl | CC#N | null | 0.25 | CC(=O)Cl.Clc1ccnc2[nH]ccc12.[I-]>CC#N>CC(=O)n1ccc2c(I)ccnc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-de07b6551367481688576978c2da05ac | CC(=O)n1ccc2c(I)ccnc21>>CC(=O)n1ccc2c(C#N)ccnc21 | IC1=C2C(=NC=C1)N(C=C2)C(C)=O.C(#N)[Cu]>>C(C)(=O)N1C=CC2=C1N=CC=C2C#N | I[c:8]1[c:7]2[cH:6][cH:5][n:4]([C:2]([CH3:1])=[O:3])[c:14]2[n:13][cH:12][cH:11]1>>[CH3:1][C:2](=[O:3])[n:4]1[cH:5][cH:6][c:7]2[c:8]([C:9]#[N:10])[cH:11][cH:12][n:13][c:14]12 | CC(=O)n1ccc2c(I)ccnc21 | CC(=O)n1ccc2c(C#N)ccnc21 | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.[Fe+2] | O1CCOCC1 | Miscellaneous | OtherReaction | 424d48da560b9f0308d0f734aeb1c121dce4a5cddb270b590d98af3d4544981a | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | c1cnc2[nH]ccc2c1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]2:[#7;a:6](-[C:7](-[C;D1;H3:8])=[O;D1;H0:9]):[c:10]:[c:11]:[c:12]:2:1>>[C;D1;H3:8]-[C:7](=[O;D1;H0:9])-[#7;a:6]1:[c:10]:[c:11]:[c:12]2:[c:5]:1:[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:2-[C:13]#[N;D1;H0:14] | null | [] | null | null | null | null | A mixture of 1-(4-iodo-pyrrolo[2,3-b]pyridin-1-yl)-ethanone (4.30 g, step C), CuCN (6.841 g), Pd2dba3 (0.729 g), and dppf (1.636 g) in 85 mL of dioxane was heated to reflux for 2 h. Solid was removed by filtration through a pad of Celite®. The filtrate was concentrated to give a yellow solid as crude compound, which wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccnc2[nH]ccc12 | c1ccnc2[nH]ccc12 | c1ccnc2[nH]ccc12 | I- | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.[Fe+2].O1CCOCC1 | null | null | CC(=O)n1ccc2c(I)ccnc21>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.[Fe+2].O1CCOCC1>CC(=O)n1ccc2c(C#N)ccnc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4851dbfdce87452b94aa877db6d8cee8 | CC(=O)n1ccc2c(C#N)ccnc21>>CC(=O)n1ccc2c(CN)ccnc21 | C(C)(=O)N1C=CC2=C1N=CC=C2C#N.CCN(CC)CC>>NCC1=C2C(=NC=C1)N(C=C2)C(C)=O | [CH3:1][C:2](=[O:3])[n:4]1[cH:5][cH:6][c:7]2[c:8]([C:9]#[N:10])[cH:11][cH:12][n:13][c:14]12>>[CH3:1][C:2](=[O:3])[n:4]1[cH:5][cH:6][c:7]2[c:8]([CH2:9][NH2:10])[cH:11][cH:12][n:13][c:14]12 | CC(=O)n1ccc2c(C#N)ccnc21 | CC(=O)n1ccc2c(CN)ccnc21 | null | [Pd] | CCO | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | c1cnc2[nH]ccc2c1 | [#7;a:1]:[c:2]1:[#7;a:3]:[c:4]:[c:5]:[c:6](-[C;H0;D2;+0:7]#[N;H0;D1;+0:8]):[c:9]:1>>[#7;a:1]:[c:2]1:[#7;a:3]:[c:4]:[c:5]:[c:6](-[CH2;D2;+0:7]-[NH2;D1;+0:8]):[c:9]:1 | null | [] | null | null | 8 | HOUR | A mixture of 1-acetyl-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile (0.872 g, step D), 10% Pd/C (0.882 g), 20 mL of Et3N, and 80 mL of EtOH was stirred at RT under balloon pressure of H2 for overnight. Solid was removed by filtration through a pad of Celite® and the filtrate was concentrated to yield a cream color residue, ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccnc2[nH]ccc12 | null | [Pd].CCO | null | 8 | CC(=O)n1ccc2c(C#N)ccnc21>[Pd].CCO>CC(=O)n1ccc2c(CN)ccnc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6c0aa67b1eb24d91ac44569514908fde | CC(=O)OC(C)=O.CC(=O)n1ccc2c(C#N)ccnc21>>CC(=O)NCc1ccnc2c1CCN2C(C)=O | C(C)(=O)N1C=CC2=C1N=CC=C2C#N.CCN(CC)CC.C(C)(=O)OC(C)=O>>C(C)(=O)N1CCC=2C1=NC=CC2CNC(C)=O | CC(=O)O[C:2]([CH3:1])=[O:3].[N:4]#[C:5][c:6]1[cH:7][cH:8][n:9][c:10]2[c:11]1[cH:12][cH:13][n:14]2[C:15]([CH3:16])=[O:17]>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][c:6]1[cH:7][cH:8][n:9][c:10]2[c:11]1[CH2:12][CH2:13][N:14]2[C:15]([CH3:16])=[O:17] | CC(=O)OC(C)=O.CC(=O)n1ccc2c(C#N)ccnc21 | CC(=O)NCc1ccnc2c1CCN2C(C)=O | null | [Pd] | CCOC(=O)C | Acylation | OtherReaction | ea2fe5f116efc7bea37722e2fd6430df4f4f9069adc1a7fb28adb8bb906ea432 | 5d4116696b6fa03c86f12421c641904a9476e7c77a6a0b264867135910513029 | c1cnc2c(c1)CCN2 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C;D1;H3:4]-[C:5](=[O;D1;H0:6])-[n;H0;D3;+0:7]1:[cH;D2;+0:8]:[cH;D2;+0:9]:[c:10]2:[c:11]:1:[#7;a:12]:[c:13]:[c:14]:[c:15]:2-[C;H0;D2;+0:16]#[N;H0;D1;+0:17]>>[C;D1;H3:4]-[C:5](=[O;D1;H0:6])-[N;H0;D3;+0:7]1-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[c:10]2:[c:11]-1:[#7;a:12]:[c:13]:[c... | null | [] | null | null | 8 | HOUR | To a mixture of 1-acetyl-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile (0.691 g, example 15, step D), 10% Pd/C (0.702 g), 5 mL of Et3N, and 20 mL of EtOAc was added acetic anhydride (1.0 mL). The mixture was stirred at RT under balloon pressure of H2 for overnight. Solid was removed by filtration through a pad of Celite® an... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Nitrile | Secondary amide.Tertiary amide | c1ccnc2[nH]ccc12 | c1cnc2c(c1)CC[NH]2 | c1cnc2c(c1)CC[NH]2 | Other | [Pd].CCOC(=O)C | null | 8 | CC(=O)OC(C)=O.CC(=O)n1ccc2c(C#N)ccnc21>[Pd].CCOC(=O)C>CC(=O)NCc1ccnc2c1CCN2C(C)=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9be657d2bf0d423696981935bcd3e52c | CC(=O)NCc1ccnc2c1CCN2C(C)=O>>NCc1ccnc2c1CCN2 | C(C)(=O)N1CCC=2C1=NC=CC2CNC(C)=O.Cl.Cl>>Cl.N1CCC=2C1=NC=CC2CN | CC(=O)[NH:2][CH2:3][c:4]1[cH:5][cH:6][n:7][c:8]2[c:9]1[CH2:10][CH2:11][N:12]2C(C)=O>>[NH2:2][CH2:3][c:4]1[cH:5][cH:6][n:7][c:8]2[c:9]1[CH2:10][CH2:11][NH:12]2 | CC(=O)NCc1ccnc2c1CCN2C(C)=O | NCc1ccnc2c1CCN2 | null | null | CCO | Reduction | OtherReaction | c3b13bb715b81429e5f944b0ab1a1a0bc4c5dc1451d3a69e22e840bfe892dddc | 70acd5420ba987f8248f15f619926d99a019597fe8db963470c7da38da6badec | c1cnc2c(c1)CCN2 | C-C(=O)-[NH;D2;+0:1]-[C:2]-[c:3]:[c:4]1:[c:5](:[#7;a:6]:[c:7])-[N;H0;D3;+0:8](-C(-C)=O)-[C:9]-[C:10]-1>>[NH2;D1;+0:1]-[C:2]-[c:3]:[c:4]1:[c:5](:[#7;a:6]:[c:7])-[NH;D2;+0:8]-[C:9]-[C:10]-1 | null | [] | 70 | CELSIUS | null | null | A mixture of N-(1-acetyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)-acetamide (0.50 g, step A), HCl (conc., 3 mL) and EtOH (12 mL) was heated to 70° C. for overnight. Additional 3 mL of conc. HCl was added to the reaction and the heating was continued for 3 more days. Solvent was evaporated to give a white residu... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Tertiary amide | Primary amine.Secondary amine | c1cnc2c(c1)CC[NH]2 | c1cnc2c(c1)CCN2 | c1cnc2c(c1)CCN2 | HO- | CCO | 70 | null | CC(=O)NCc1ccnc2c1CCN2C(C)=O>CCO>NCc1ccnc2c1CCN2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cf7b1f854a70487c9d09d1b2da244b25 | CC(C)(C)c1ccc(N)cc1.CN(C)C(On1nnc2ccccc21)=[N+](C)C.O=C(O)c1cc(Cl)nnc1Cl>>CC(C)(C)c1ccc(NC(=O)c2cc(Cl)nnc2On2nnc3ccccc32)cc1 | ClC=1N=NC(=CC1C(=O)O)Cl.C(C)(C)(C)C1=CC=C(N)C=C1.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=C2)N=N1.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>>C(C)(C)(C)C1=CC=C(C=C1)NC(=O)C1=C(N=NC(=C1)Cl)ON1N=NC2=C1C=CC=C2 | [CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:29][cH:30]1.CN(C)C(=[N+](C)C)[O:19][n:20]1[n:21][n:22][c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]12.O[C:10](=[O:11])[c:12]1[cH:13][c:14]([Cl:15])[n:16][n:17][c:18]1Cl>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][C:10](=[O:11])[c:12]2[cH:13... | CC(C)(C)c1ccc(N)cc1.CN(C)C(On1nnc2ccccc21)=[N+](C)C.O=C(O)c1cc(Cl)nnc1Cl | CC(C)(C)c1ccc(NC(=O)c2cc(Cl)nnc2On2nnc3ccccc32)cc1 | null | null | O.CN(C)C=O | Acylation | OtherReaction | 1e5dca61dc94ea5b4ed7a5d733145329c4f338dc815624480f1556e40e8085c8 | c1dd332d9cc02e7777765602b6c5f9df675988ea71fbab481115deacfc9522af | O=C(Nc1ccccc1)c1ccnnc1On1nnc2ccccc21 | C-N(-C)-C(-[O;H0;D2;+0:1]-[#7;a:2]1:[#7;a:3]:[#7;a:4]:[c:5]:[c:6]:1)=[N+](-C)-C.Cl-[c;H0;D3;+0:7]1:[#7;a:8]:[#7;a:9]:[c:10]:[c:11]:[c:12]:1-[C;H0;D3;+0:13](-O)=[O;D1;H0:14].[NH2;D1;+0:15]-[c:16](:[c:17]):[c:18]>>[O;D1;H0:14]=[C;H0;D3;+0:13](-[NH;D2;+0:15]-[c:16](:[c:17]):[c:18])-[c:12]1:[c:11]:[c:10]:[#7;a:9]:[#7;a:8]:... | null | [] | null | null | 8 | HOUR | A mixture of 3,6-dichloropyridazine-4-carboxylic acid (1.00 g, 5.18 mmol), 4-tert-butylaniline (0.92 ml, 5.60 mmol), TBTU (1.75 g, 5.44 mmol), and DIEA (1.80 ml, 10.4 mmol) in 7.5 ml of anhydrous DMF was stirred at RT under N2 overnight. The mixtrue was diluted with H2O, extracted with EtOAc, and the combined organic p... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Amidinium.Carboxylic acid.Primary amine | Secondary amide | c1ccnnc1 | c1ccnnc1 | c1ccccc1.c1ccnnc1.c1ccc2[nH]nnc2c1 | HCl | O.CN(C)C=O | null | 8 | CC(C)(C)c1ccc(N)cc1.CN(C)C(On1nnc2ccccc21)=[N+](C)C.O=C(O)c1cc(Cl)nnc1Cl>O.CN(C)C=O>CC(C)(C)c1ccc(NC(=O)c2cc(Cl)nnc2On2nnc3ccccc32)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b98a01a0e44040b18d921b4e7a5a6190 | NCCc1ccc([N+](=O)[O-])cc1.O=C(OC(=O)C(F)(F)F)C(F)(F)F>>O=C(NCCc1ccc([N+](=O)[O-])cc1)C(F)(F)F | Cl.[N+](=O)([O-])C1=CC=C(CCN)C=C1.CCN(C(C)C)C(C)C.O(C(=O)C(F)(F)F)C(=O)C(F)(F)F>>FC(C(=O)NCCC1=CC=C(C=C1)[N+](=O)[O-])(F)F | [NH2:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][cH:14]1.O=C(O[C:2](=[O:1])[C:15]([F:16])([F:17])[F:18])C(F)(F)F>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][cH:14]1)[C:15]([F:16])([F:17])[F:18] | NCCc1ccc([N+](=O)[O-])cc1.O=C(OC(=O)C(F)(F)F)C(F)(F)F | O=C(NCCc1ccc([N+](=O)[O-])cc1)C(F)(F)F | null | null | C(Cl)Cl | Acylation | Aminolysis of esters | 2496adcbe03518c7603aaf61e5fe7829c406f3166e3cae69e10655d03d283206 | 379184f1d7c82f259f4768a95bfa42449d23cbbab90c9ea080b24f11fa1841e2 | c1ccccc1 | F-C(-F)(-F)-C(=O)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[F;D1;H0:4])(-[F;D1;H0:5])-[F;D1;H0:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[F;D1;H0:4])(-[F;D1;H0:5])-[F;D1;H0:6] | null | [] | null | null | 1 | HOUR | To a solution of 4-nitrophenethylamine hydrochloride (50 g, 0.247 mole), DIEA (128 mL, 0.74 mole, 3 eq.) and CH2Cl2 (500 mL) in a 1 L round bottom flask equipped with a magnetic stirrer was added (CF3CO)2O (52.5 mL, 0.37 mole, 1.5 eq) dropwise at 5-10° C. (with ice/water bath). After stirring for another 1 h after the ... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Anhydride.Primary amine | Secondary amide | null | null | c1ccccc1 | HF | C(Cl)Cl | null | 1 | NCCc1ccc([N+](=O)[O-])cc1.O=C(OC(=O)C(F)(F)F)C(F)(F)F>C(Cl)Cl>O=C(NCCc1ccc([N+](=O)[O-])cc1)C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bef25b9396c9487081cd1518b9b04435 | C=O.O=C(NCCc1ccc([N+](=O)[O-])cc1)C(F)(F)F>>O=C(N1CCc2ccc([N+](=O)[O-])cc2C1)C(F)(F)F | FC(C(=O)NCCC1=CC=C(C=C1)[N+](=O)[O-])(F)F.C=O.OS(=O)(=O)O>>FC(C(=O)N1CC2=CC(=CC=C2CC1)[N+](=O)[O-])(F)F | O=[CH2:15].[O:1]=[C:2]([NH:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][cH:14]1)[C:16]([F:17])([F:18])[F:19]>>[O:1]=[C:2]([N:3]1[CH2:4][CH2:5][c:6]2[cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][c:14]2[CH2:15]1)[C:16]([F:17])([F:18])[F:19] | C=O.O=C(NCCc1ccc([N+](=O)[O-])cc1)C(F)(F)F | O=C(N1CCc2ccc([N+](=O)[O-])cc2C1)C(F)(F)F | null | null | CC(=O)O | Functional Group Addition | OtherReaction | 94f040fcb4acc0a38bfc8b3d5c42016ed2f3232d0d2ca256bd08fe82f2fd7e7e | 223f487ee379c411477f5951d0a5481815ffe203b1020549e24ddf97870bf172 | c1ccc2c(c1)CCNC2 | O=[CH2;D1;+0:1].[F;D1;H0:2]-[C:3](-[F;D1;H0:4])(-[F;D1;H0:5])-[C:6](=[O;D1;H0:7])-[NH;D2;+0:8]-[C:9]-[C:10]-[c:11](:[c:12]):[cH;D2;+0:13]:[c:14]:[c:15]>>[F;D1;H0:2]-[C:3](-[F;D1;H0:4])(-[F;D1;H0:5])-[C:6](=[O;D1;H0:7])-[N;H0;D3;+0:8]1-[C:9]-[C:10]-[c:11](:[c:12]):[c;H0;D3;+0:13](:[c:14]:[c:15])-[CH2;D2;+0:1]-1 | null | [] | 40 | CELSIUS | 2 | HOUR | To the mixture of 2,2,2-trifluoro-N-[2-(4-nitro-phenyl)-ethyl]-acetamide (65 g, 0.25 mole), paraformaldehyde (42.4 g, 0.375 mole, 1.5 eq.) and HOAc (200 mL) in a 1 L round bottom flask equipped with a magnetic stirrer and a ice/water bath was added H2SO4 (300 mL) slowly while maintaining reaction temperature under 40° ... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amide | Tertiary amide | c1ccccc1 | c1ccc2c(c1)CC[NH]C2 | c1ccc2c(c1)CC[NH]C2 | HO- | CC(=O)O | 40 | 2 | C=O.O=C(NCCc1ccc([N+](=O)[O-])cc1)C(F)(F)F>CC(=O)O>O=C(N1CCc2ccc([N+](=O)[O-])cc2C1)C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0d70fa6020004eb6abce4547e2535631 | O=[N+]([O-])c1ccc2c(c1)CNCC2>>Nc1ccc2ccncc2c1 | [N+](=O)([O-])C1=CC=C2CCNCC2=C1>>NC1=CC=C2C=CN=CC2=C1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]2[c:10]([cH:11]1)[CH2:9][NH:8][CH2:7][CH2:6]2>>[NH2:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][n:8][cH:9][c:10]2[cH:11]1 | O=[N+]([O-])c1ccc2c(c1)CNCC2 | Nc1ccc2ccncc2c1 | null | [Pd] | C(COCCO)O.CO | Functional Group Interconversion | OtherReaction | 2b9b3f977fc216aab6c9d2f0cfbc0cc2a9312ed594563f9c2e1cf6986b24e5d5 | a2f9656e053ae1256a1524718102703aa12e179ae67d56ab263b0c5c1c1aa2be | c1ccc2cnccc2c1 | O=[N+;H0;D3:1](-[O-])-[c:2]1:[c:3]:[c:4]2:[c:5](:[c:6]:[c:7]:1)-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[NH;D2;+0:10]-[CH2;D2;+0:11]-2>>[NH2;D1;+0:1]-[c:2]1:[c:3]:[c:4]2:[cH;D2;+0:11]:[n;H0;D2;+0:10]:[cH;D2;+0:9]:[cH;D2;+0:8]:[c:5]:2:[c:6]:[c:7]:1 | null | [] | null | null | null | null | A mixture of 7-nitro-1,2,3,4-tetrahydro-isoquinoline (1.5 g, 8.38 mmole) and 10% Pd/C (300 mg) in diethylene glycol (5 mL) was reacted in a Smith Synthesizer under microwave radiation at 220° C. for 25 min. The resulting mixture was diluted with MeOH and filtered. The filtrate was concentrated and diluted with CH2Cl2, ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Secondary amine | Primary amine | c1ccc2c(c1)CCNC2 | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | HO- | [Pd].C(COCCO)O.CO | null | null | O=[N+]([O-])c1ccc2c(c1)CNCC2>[Pd].C(COCCO)O.CO>Nc1ccc2ccncc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ad3a263b1c0441b98e86238d79a6873a | CNc1ncnc2ccc([N+](=O)[O-])cc12>>CNc1ncnc2ccc(N)cc12 | CNC1=NC=NC2=CC=C(C=C12)[N+](=O)[O-].[N+](=O)([O-])C1=NC2=CC=CC=C2C=N1.[N+](=O)([O-])C1=NC2=CC=CC=C2C=N1>>CNC1=NC=NC2=CC=C(C=C12)N | O=[N+:11]([O-])[c:10]1[cH:9][cH:8][c:7]2[n:6][cH:5][n:4][c:3]([NH:2][CH3:1])[c:13]2[cH:12]1>>[CH3:1][NH:2][c:3]1[n:4][cH:5][n:6][c:7]2[cH:8][cH:9][c:10]([NH2:11])[cH:12][c:13]12 | CNc1ncnc2ccc([N+](=O)[O-])cc12 | CNc1ncnc2ccc(N)cc12 | null | [Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2ncncc2c1 | 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 | 3 | HOUR | A mixture of methyl-(6-nitro-quinazolin-4-yl)-amine (0.16 g; see Synthesis of Certain Nitroquinazoline Derivatives Structurally Related to some Chemotherapeutic Agents, Botros, S., et. al., Egyptian Journal of Pharmaceutical Sciences, 13(1), 11-21, (1972) for a description of preparing the nitro-quinazoline) and Pd/C (... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2ncncc2c1 | Other | [Pd].CO | null | 3 | CNc1ncnc2ccc([N+](=O)[O-])cc12>[Pd].CO>CNc1ncnc2ccc(N)cc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e2298c82bd95408db8c2b05c00f9dffd | CC(C)(C)OC(=O)N1CCC(=O)CC1.Cn1cc([N+](=O)[O-])cc([N+](=O)[O-])c1=O>>CC(C)(C)OC(=O)N1CCc2ncc([N+](=O)[O-])cc2C1 | N.CO.CN1C(C(=CC(=C1)[N+](=O)[O-])[N+](=O)[O-])=O.C(C)(C)(C)OC(=O)N1CCC(CC1)=O>>C(C)(C)(C)OC(=O)N1CC=2C=C(C=NC2CC1)[N+](=O)[O-] | O=C1C[CH2:20][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10]1.C[n:12]1[c:11](=O)[c:19]([N+](=O)[O-])[cH:18][c:14]([N+:15](=[O:16])[O-:17])[cH:13]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][c:11]2[n:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][c:19]2[CH2:20]1 | CC(C)(C)OC(=O)N1CCC(=O)CC1.Cn1cc([N+](=O)[O-])cc([N+](=O)[O-])c1=O | CC(C)(C)OC(=O)N1CCc2ncc([N+](=O)[O-])cc2C1 | null | null | null | C-C Coupling | OtherReaction | 4b2ff49aecb8245cdaf7fa14e8e8ea329800fe6d3b03c18a8c62f67ab0f8cba5 | 54c883540e3e624495d3641c2536bb51a80c522d3dd12da5b0bd2ae87c2599b9 | c1cnc2c(c1)CNCC2 | C-[n;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c;H0;D3;+0:5](-[N+](=O)-[O-]):[c;H0;D3;+0:6]:1=O.O=C1-C-[CH2;D2;+0:7]-[#7:8](-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12](-[C;D1;H3:13])(-[C;D1;H3:14])-[C;D1;H3:15])-[C:16]-[CH2;D2;+0:17]-1>>[C;D1;H3:13]-[C:12](-[C;D1;H3:14])(-[C;D1;H3:15])-[#8:11]-[C:9](=[O;D1;H0:10])-[#7:8]1-[C:16]-[CH2;D... | null | [] | 70 | CELSIUS | 24 | HOUR | 2M solution of NH3 in MeOH (225 mL, 452.25 mmol) was added to a reaction vessel containing 1-methyl-3,5-dinitro-1H-pyridin-2-one (6 g, 30.15 mmol) and 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (6.6 g, 33.15 mmol). The vessel was then sealed and the reaction was stirred for 24 h at 70° C. After the resulting m... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Nitro group | null | C1CC[NH]CC1.c1ccncc1 | c1cnc2c(c1)C[NH]CC2 | c1cnc2c(c1)C[NH]CC2 | HO- | null | 70 | 24 | CC(C)(C)OC(=O)N1CCC(=O)CC1.Cn1cc([N+](=O)[O-])cc([N+](=O)[O-])c1=O>>CC(C)(C)OC(=O)N1CCc2ncc([N+](=O)[O-])cc2C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d140c817e35a433bb21d20b8a21b70a3 | CC(C)(C)OC(=O)N1CCc2ncc([N+](=O)[O-])cc2C1>>O=[N+]([O-])c1cnc2c(c1)CNCC2 | C(C)(C)(C)OC(=O)N1CC=2C=C(C=NC2CC1)[N+](=O)[O-].C(=O)(C(F)(F)F)O>>[N+](=O)([O-])C=1C=NC=2CCNCC2C1 | CC(C)(C)OC(=O)[N:11]1[CH2:10][c:8]2[c:7]([n:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:9]2)[CH2:13][CH2:12]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][n:6][c:7]2[c:8]([cH:9]1)[CH2:10][NH:11][CH2:12][CH2:13]2 | CC(C)(C)OC(=O)N1CCc2ncc([N+](=O)[O-])cc2C1 | O=[N+]([O-])c1cnc2c(c1)CNCC2 | null | null | C(Cl)Cl | Reduction | Boc amine deprotection | 4b38b79c06173cb4f14518182fe53e74ca9658ff8410d2d6ca7625716a5fa615 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1cnc2c(c1)CNCC2 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[c:3]:[c:4](:[#7;a:5])-[C:6]-[C:7]-1>>[#7;a:5]:[c:4]1:[c:3]-[C:2]-[NH;D2;+0:1]-[C:7]-[C:6]-1 | null | [] | null | null | 18 | HOUR | To the solution of 3-nitro-7,8-dihydro-5H-[1,6]naphthyridine-6-carboxylic acid tert-butyl ester (6.14 g, 22 mmol) in CH2Cl2 (60 mL) was added TFA (7 mL). The reaction was stirred for 18 h at RT. After evaporation of the solvent, the residue was taken into water and neutralized with saturated NaHCO3 aqueous solution. Th... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | c1cnc2c(c1)C[NH]CC2 | c1cnc2c(c1)CNCC2 | c1cnc2c(c1)CNCC2 | HO- | C(Cl)Cl | null | 18 | CC(C)(C)OC(=O)N1CCc2ncc([N+](=O)[O-])cc2C1>C(Cl)Cl>O=[N+]([O-])c1cnc2c(c1)CNCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-37f98a9bae984be39600138d7baac58e | O=[N+]([O-])c1cnc2c(c1)CNCC2>>Nc1cnc2ccncc2c1 | [N+](=O)([O-])C=1C=NC=2CCNCC2C1.C(CCCC)O>>N1=CC(=CC2=CN=CC=C12)N | O=[N+:1]([O-])[c:2]1[cH:3][n:4][c:5]2[c:10]([cH:11]1)[CH2:9][NH:8][CH2:7][CH2:6]2>>[NH2:1][c:2]1[cH:3][n:4][c:5]2[cH:6][cH:7][n:8][cH:9][c:10]2[cH:11]1 | O=[N+]([O-])c1cnc2c(c1)CNCC2 | Nc1cnc2ccncc2c1 | null | [Pd] | CO | Functional Group Interconversion | OtherReaction | 01c5e5d221ddbc28783b32a15911861c244d6952b477c15cb426990eeb18eb94 | a2f9656e053ae1256a1524718102703aa12e179ae67d56ab263b0c5c1c1aa2be | c1cnc2ccncc2c1 | O=[N+;H0;D3:1](-[O-])-[c:2]1:[c:3]:[c:4]2:[c:5](:[#7;a:6]:[c:7]:1)-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[NH;D2;+0:10]-[CH2;D2;+0:11]-2>>[NH2;D1;+0:1]-[c:2]1:[c:3]:[c:4]2:[cH;D2;+0:11]:[n;H0;D2;+0:10]:[cH;D2;+0:9]:[cH;D2;+0:8]:[c:5]:2:[#7;a:6]:[c:7]:1 | null | [] | 180 | CELSIUS | 1 | HOUR | 3-Nitro-5,6,7,8-tetrahydro-[1,6]naphthyridine (1 g, 5.6 mmol), pentanol (2 mL) and Pd/C (300 mg) were placed in a microwave reaction vessel and stirred under microwave irradiation at 180° C. for 1 h. After cooling, the mixture was diluted with MeOH and filtered through a pad of Celite. The solvent was removed and the c... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Secondary amine | Primary amine | c1cnc2c(c1)CNCC2 | c1cnc2ccncc2c1 | c1cnc2ccncc2c1 | HO- | [Pd].CO | 180 | 1 | O=[N+]([O-])c1cnc2c(c1)CNCC2>[Pd].CO>Nc1cnc2ccncc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-43714f609d3a495f8a23cb17bbbade8d | CO.Nc1ccc(C(O)(C(F)(F)F)C(F)(F)F)cc1>>COC(c1ccc(N)cc1)(C(F)(F)F)C(F)(F)F | NC1=CC=C(C=C1)C(C(F)(F)F)(C(F)(F)F)O.CC(C)OC(=O)/N=N/C(=O)OC(C)C.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.CO>>FC(C(C(F)(F)F)(OC)C1=CC=C(C=C1)N)(F)F | O[CH3:1].[OH:2][C:3]([c:4]1[cH:5][cH:6][c:7]([NH2:8])[cH:9][cH:10]1)([C:11]([F:12])([F:13])[F:14])[C:15]([F:16])([F:17])[F:18]>>[CH3:1][O:2][C:3]([c:4]1[cH:5][cH:6][c:7]([NH2:8])[cH:9][cH:10]1)([C:11]([F:12])([F:13])[F:14])[C:15]([F:16])([F:17])[F:18] | CO.Nc1ccc(C(O)(C(F)(F)F)C(F)(F)F)cc1 | COC(c1ccc(N)cc1)(C(F)(F)F)C(F)(F)F | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Alcohol to ether | 2b3b0a592e17fb86c0c9a5558af8e97944b1fdf4fc42848049c3b68d250fb461 | bfa20b3e9bdc2cabcf6866f18be24887f07fae119c8dc82c4bf47d46e44ff51b | c1ccccc1 | O-[CH3;D1;+0:1].[F;D1;H0:2]-[C:3](-[F;D1;H0:4])(-[F;D1;H0:5])-[C:6](-[OH;D1;+0:7])(-[c:8])-[C:9](-[F;D1;H0:10])(-[F;D1;H0:11])-[F;D1;H0:12]>>[CH3;D1;+0:1]-[O;H0;D2;+0:7]-[C:6](-[c:8])(-[C:3](-[F;D1;H0:2])(-[F;D1;H0:4])-[F;D1;H0:5])-[C:9](-[F;D1;H0:10])(-[F;D1;H0:11])-[F;D1;H0:12] | null | [] | null | null | null | null | A mixture of 2-(4-amino-phenyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol (1 eq.), DIAD (1.96 eq.), PPh3 (polymer-bound, 2.36 eq) and MeOH (1.1 eq) in THF (100 mL) was stirred at reflux for 16 h. After filtration and concentration, the crude was purified by flash chromatography (20% EtOAc/CH2Cl2) to give the title compound as... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol.Methanol | Ether | null | null | c1ccccc1 | HO- | C1CCOC1 | null | null | CO.Nc1ccc(C(O)(C(F)(F)F)C(F)(F)F)cc1>C1CCOC1>COC(c1ccc(N)cc1)(C(F)(F)F)C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2330da20944543859242ac777de8c912 | Nc1ccc2ccncc2c1.O=C(Nc1ccc(C(F)(F)C(F)(F)F)cc1)c1cccnc1F>>O=C(Nc1ccc(C(F)(F)C(F)(F)F)cc1)c1cccnc1Nc1ccc2ccncc2c1 | FC1=C(C(=O)NC2=CC=C(C=C2)C(C(F)(F)F)(F)F)C=CC=N1.NC1=CC=C2C=CN=CC2=C1.C(=O)(C(F)(F)F)O>>C1=NC=CC2=CC=C(C=C12)NC1=C(C(=O)NC2=CC=C(C=C2)C(C(F)(F)F)(F)F)C=CC=N1 | [NH2:23][c:24]1[cH:25][cH:26][c:27]2[cH:28][cH:29][n:30][cH:31][c:32]2[cH:33]1.F[c:22]1[c:17]([C:2](=[O:1])[NH:3][c:4]2[cH:5][cH:6][c:7]([C:8]([F:9])([F:10])[C:11]([F:12])([F:13])[F:14])[cH:15][cH:16]2)[cH:18][cH:19][cH:20][n:21]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([C:8]([F:9])([F:10])[C:11]([F:12])([F:13])[F:1... | Nc1ccc2ccncc2c1.O=C(Nc1ccc(C(F)(F)C(F)(F)F)cc1)c1cccnc1F | O=C(Nc1ccc(C(F)(F)C(F)(F)F)cc1)c1cccnc1Nc1ccc2ccncc2c1 | null | null | CC(C)(C)O | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C(Nc1ccccc1)c1cccnc1Nc1ccc2ccncc2c1 | F-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[C:5](=[O;D1;H0:6])-[#7:7]-[c:8]):[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[O;D1;H0:6]=[C:5](-[#7:7]-[c:8])-[c:4](:[c:9]):[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[#7;a:2]:[c:3] | null | [] | 90 | CELSIUS | 24 | HOUR | To a mixture of 2-fluoro-N-(4-pentafluoroethyl-phenyl)-nicotinamide (112 mg) and 7-aminoisoquinoline (40 mg) in t-BuOH (0.5 mL) was added TFA (94 μL). The resulting mixture was stirred for 24 h at 90° C., cooled to RT and purified by flash chromatography (4:1:0.1; MeOH/CH2Cl2/MeOH) to give the title compound as a yello... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1ccc2cnccc2c1 | HF | CC(C)(C)O | 90 | 24 | Nc1ccc2ccncc2c1.O=C(Nc1ccc(C(F)(F)C(F)(F)F)cc1)c1cccnc1F>CC(C)(C)O>O=C(Nc1ccc(C(F)(F)C(F)(F)F)cc1)c1cccnc1Nc1ccc2ccncc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a4374f3946a54cfc9e1bff7fdf7f9ebf | CCOC(=O)c1ccccc1Br.Nc1ccc2ccncc2c1>>CCOC(=O)c1ccccc1Nc1ccc2ccncc2c1 | C(C)OC(C1=C(C=CC=C1)Br)=O.NC1=CC=C2C=CN=CC2=C1.C=1C=CC(=CC1)P(C=2C=CC=CC2)C3=CC=C4C=CC=CC4=C3C5=C6C=CC=CC6=CC=C5P(C=7C=CC=CC7)C=8C=CC=CC8.C(=O)([O-])[O-].[K+].[K+]>>C(C)OC(C1=C(C=CC=C1)NC1=CC=C2C=CN=CC2=C1)=O | Br[c:11]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:7][cH:8][cH:9][cH:10]1.[NH2:12][c:13]1[cH:14][cH:15][c:16]2[cH:17][cH:18][n:19][cH:20][c:21]2[cH:22]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[NH:12][c:13]1[cH:14][cH:15][c:16]2[cH:17][cH:18][n:19][cH:20][c:21]2[cH:22]1 | CCOC(=O)c1ccccc1Br.Nc1ccc2ccncc2c1 | CCOC(=O)c1ccccc1Nc1ccc2ccncc2c1 | null | CC(=O)[O-].CC(=O)[O-].[Pd+2] | C1(=CC=CC=C1)C.C(Cl)Cl | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccc3ccncc3c2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8]):[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:8]-[#8:7]-[C:5](=[O;D1;H0:6])-[c:4](:[c:9]):[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[c:2]:[c:3] | null | [] | 105 | CELSIUS | 16 | HOUR | A mixture of 2-bromo-benzoic acid ethyl ester (458 mg, 2.0 mmol), 7-aminoisoquinoline (144 mg, 1.0 mmol), Pd(OAc)2 (11 mg), BINAP (30 mg) and K2CO3 (414 mg) in 1 mL of toluene in a sealed tube was stirred for 16 h at 105° C. The reaction mixture was then allowed to cool to RT, diluted with 20 ml of CH2Cl2, filtered thr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2cnccc2c1 | HBr | CC(=O)[O-].CC(=O)[O-].[Pd+2].C1(=CC=CC=C1)C.C(Cl)Cl | 105 | 16 | CCOC(=O)c1ccccc1Br.Nc1ccc2ccncc2c1>CC(=O)[O-].CC(=O)[O-].[Pd+2].C1(=CC=CC=C1)C.C(Cl)Cl>CCOC(=O)c1ccccc1Nc1ccc2ccncc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-96e7b7a1a8d544318a5a7bb254af830f | CC(C)(C)OC(=O)N1Cc2cc(N)ccc2C(C)(C)C1.O=C(Cl)c1cccnc1Cl>>CC(C)(C)OC(=O)N1Cc2cc(NC(=O)c3cccnc3Cl)ccc2C(C)(C)C1 | ClC1=C(C(=O)Cl)C=CC=N1.C(C)(C)(C)OC(=O)N1CC2=CC(=CC=C2C(C1)(C)C)N.C(=O)(O)[O-].[Na+]>>C(C)(C)(C)OC(=O)N1CC2=CC(=CC=C2C(C1)(C)C)NC(=O)C=1C(=NC=CC1)Cl | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][c:10]2[cH:11][c:12]([NH2:13])[cH:23][cH:24][c:25]2[C:26]([CH3:27])([CH3:28])[CH2:29]1.Cl[C:14](=[O:15])[c:16]1[cH:17][cH:18][cH:19][n:20][c:21]1[Cl:22]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][c:10]2[cH:11][c:12]([NH:13][C:14](=[O:15])[... | CC(C)(C)OC(=O)N1Cc2cc(N)ccc2C(C)(C)C1.O=C(Cl)c1cccnc1Cl | CC(C)(C)OC(=O)N1Cc2cc(NC(=O)c3cccnc3Cl)ccc2C(C)(C)C1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccc2c(c1)CNCC2)c1cccnc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[Cl;D1;H0:6]):[#7;a:7]:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[Cl;D1;H0:6]-[c:5](:[#7;a:7]:[c:8]):[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:4] | null | [] | null | null | 1 | HOUR | To a solution of 2-chloronicotinoyl chloride (3.52 g, 20 mmol, 1.0 eq.) and 7-amino-4,4-dimethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (5.52 g, 20 mmol, 1.0 eq.) in CH2Cl2 (100 mL) was added NaHCO3 (6.4 g, 80 mmol, 4.0 eq.). The mixture was stirred for 1 h at RT, then filtered and concentrated,... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2c(c1)CC[NH]C2.c1ccncc1 | HCl | C(Cl)Cl | null | 1 | CC(C)(C)OC(=O)N1Cc2cc(N)ccc2C(C)(C)C1.O=C(Cl)c1cccnc1Cl>C(Cl)Cl>CC(C)(C)OC(=O)N1Cc2cc(NC(=O)c3cccnc3Cl)ccc2C(C)(C)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e61b8703ace74c6aad75e64ffd94009d | CC(C)(C)OC(=O)N1Cc2cc(NC(=O)c3cccnc3Cl)ccc2C(C)(C)C1.Nc1ccc2ccncc2c1>>CC(C)(C)OC(=O)N1Cc2cc(NC(=O)c3cccnc3Nc3ccc4ccncc4c3)ccc2C(C)(C)C1 | C(C)(C)(C)OC(=O)N1CC2=CC(=CC=C2C(C1)(C)C)NC(=O)C=1C(=NC=CC1)Cl.NC1=CC=C2C=CN=CC2=C1.C1(CCCCC1)P(C1=C(C=CC=C1)C1=C(C=CC=C1)N(C)C)C1CCCCC1>>C(C)(C)(C)OC(=O)N1CC2=CC(=CC=C2C(C1)(C)C)NC(=O)C=1C(=NC=CC1)NC1=CC=C2C=CN=CC2=C1 | Cl[c:21]1[c:16]([C:14]([NH:13][c:12]2[cH:11][c:10]3[c:35]([cH:34][cH:33]2)[C:36]([CH3:37])([CH3:38])[CH2:39][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9]3)=[O:15])[cH:17][cH:18][cH:19][n:20]1.[NH2:22][c:23]1[cH:24][cH:25][c:26]2[cH:27][cH:28][n:29][cH:30][c:31]2[cH:32]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[... | CC(C)(C)OC(=O)N1Cc2cc(NC(=O)c3cccnc3Cl)ccc2C(C)(C)C1.Nc1ccc2ccncc2c1 | CC(C)(C)OC(=O)N1Cc2cc(NC(=O)c3cccnc3Nc3ccc4ccncc4c3)ccc2C(C)(C)C1 | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C(Nc1ccc2c(c1)CNCC2)c1cccnc1Nc1ccc2ccncc2c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[C:5](=[O;D1;H0:6])-[#7:7]-[c:8]):[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[O;D1;H0:6]=[C:5](-[#7:7]-[c:8])-[c:4](:[c:9]):[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[#7;a:2]:[c:3] | null | [] | 70 | CELSIUS | 17 | HOUR | To a mixture of 7-[(2-chloro-pyridine-3-carbonyl)-amino]-4,4-dimethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (20.8 g, 50 mmol, 1.0 eq.), 7-aminoisoquinoline (7.2 g, 50 mmol, 1.0 eq.), Pd2(dba)3 (915 mg, 1 mmol, 0.02 eq), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (CAS# 213697-53-1, S... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccc2c(c1)CC[NH]C2.c1ccncc1.c1ccc2cnccc2c1 | HCl | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].O | 70 | 17 | CC(C)(C)OC(=O)N1Cc2cc(NC(=O)c3cccnc3Cl)ccc2C(C)(C)C1.Nc1ccc2ccncc2c1>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].O>CC(C)(C)OC(=O)N1Cc2cc(NC(=O)c3cccnc3Nc3ccc4ccncc4c3)ccc2C(C)(C)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e2170a1e61204cadae2ea9f293198580 | CC(C)(C)c1ccc(NC(=O)c2ccccc2N)cc1.Clc1ccc2ccncc2n1>>CC(C)(C)c1ccc(NC(=O)c2ccccc2Nc2ccc3ccncc3n2)cc1 | ClC1=NC2=CN=CC=C2C=C1.NC1=C(C(=O)NC2=CC=C(C=C2)C(C)(C)C)C=CC=C1.C1(CCCCC1)P(C1=C(C=CC=C1)C1=C(C=CC=C1)N(C)C)C1CCCCC1.[Li]N([Si](C)(C)C)[Si](C)(C)C>>C(C)(C)(C)C1=CC=C(C=C1)NC(C1=C(C=CC=C1)NC1=NC2=CN=CC=C2C=C1)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[NH2:18])[cH:29][cH:30]1.Cl[c:19]1[cH:20][cH:21][c:22]2[cH:23][cH:24][n:25][cH:26][c:27]2[n:28]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][c... | CC(C)(C)c1ccc(NC(=O)c2ccccc2N)cc1.Clc1ccc2ccncc2n1 | CC(C)(C)c1ccc(NC(=O)c2ccccc2Nc2ccc3ccncc3n2)cc1 | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1CCOC1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 9aaceba939b33cad498c676d532db91be3635aea14c5a94e898ffbf17b5632f1 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C(Nc1ccccc1)c1ccccc1Nc1ccc2ccncc2n1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]):[c:6]:[c:7].[#7:8]-[C:9](=[O;D1;H0:10])-[c:11]:[c:12](-[NH2;D1;+0:13]):[c:14]>>[#7:8]-[C:9](=[O;D1;H0:10])-[c:11]:[c:12](-[NH;D2;+0:13]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]):[c:6]:[c:7]):[c:14] | null | [] | 70 | CELSIUS | 24 | HOUR | 2-Chloro-[1,7]naphthyridine (100 mg, 0.61 mmol), 2-amino-N-(4-tert-butyl-phenyl)-benzamide (164 mg, 0.61 mmol), Pd2(dba)3 (6 mg, 0.006 mmol), (2′-Dicyclohexylphosphanyl-biphenyl-2-yl)-dimethyl-amine (6 mg, 0.015 mmol), and 1M solution of LiN(TMS)2 in THF (1.83 mL), 1.83 mmol) were added to a reaction vessel. The vessel... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cnc2cnccc2c1 | c1cnc2cnccc2c1 | c1ccccc1.c1ccccc1.c1cnc2cnccc2c1 | HCl | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1CCOC1 | 70 | 24 | CC(C)(C)c1ccc(NC(=O)c2ccccc2N)cc1.Clc1ccc2ccncc2n1>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1CCOC1>CC(C)(C)c1ccc(NC(=O)c2ccccc2Nc2ccc3ccncc3n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-98477e2db71c432cafa206b1cb5ed9e6 | COc1ccc([N+](=O)[O-])cc1Br>>O=[N+]([O-])c1ccc(O)c(Br)c1 | BrC1=C(C=CC(=C1)[N+](=O)[O-])OC>>BrC1=C(C=CC(=C1)[N+](=O)[O-])O | C[O:8][c:7]1[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:11][c:9]1[Br:10]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([OH:8])[c:9]([Br:10])[cH:11]1 | COc1ccc([N+](=O)[O-])cc1Br | O=[N+]([O-])c1ccc(O)c(Br)c1 | null | null | Cl.CN(C)C=O.CCOC(=O)C | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 52.3 | [{"value": 52.0, "product": "BrC1=C(C=CC(=C1)[N+](=O)[O-])O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.3, "product": "BrC1=C(C=CC(=C1)[N+](=O)[O-])O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 115 | CELSIUS | null | null | 2-Bromo-4-nitroanisole (20 g, 0.086 mol) was dissolved in DMF (414 mL) at rt under N2. Sodium ethylthiolate (17.4 g, 0.207 mol) was added and the reaction mixture was warmed to 115° C. for 2 h. The reaction was cooled to rt and diluted with EtOAc (200 mL) and 1 M HCl (aq., 200 mL). The phases were separated, and the de... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1 | Other | Cl.CN(C)C=O.CCOC(=O)C | 115 | null | COc1ccc([N+](=O)[O-])cc1Br>Cl.CN(C)C=O.CCOC(=O)C>O=[N+]([O-])c1ccc(O)c(Br)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8df9475ad07946fbab307a20a3f3a446 | O=[N+]([O-])c1ccc(O)c(Br)c1.OCc1cccc(F)c1>>O=[N+]([O-])c1ccc(OCc2cccc(F)c2)c(Br)c1 | BrC1=C(C=CC(=C1)[N+](=O)[O-])O.FC=1C=C(CO)C=CC1.CC(C)OC(=O)/N=N/C(=O)OC(C)C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>BrC1=C(C=CC(=C1)[N+](=O)[O-])OCC1=CC(=CC=C1)F | [O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([OH:8])[c:17]([Br:18])[cH:19]1.O[CH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]([F:15])[cH:16]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][c:14]([F:15])[cH:16]2)[c:17]([Br:18])[cH:19]1 | O=[N+]([O-])c1ccc(O)c(Br)c1.OCc1cccc(F)c1 | O=[N+]([O-])c1ccc(OCc2cccc(F)c2)c(Br)c1 | null | null | O.CCOC(=O)C.C1CCOC1 | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc(COc2ccccc2)cc1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4] | 68 | [{"value": 68.0, "product": "BrC1=C(C=CC(=C1)[N+](=O)[O-])OCC1=CC(=CC=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.3, "product": "BrC1=C(C=CC(=C1)[N+](=O)[O-])OCC1=CC(=CC=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 3 | HOUR | 2-Bromo-4-nitrophenol (4.86 g, 0.0223 mol), triphenylphosphine (7.6 g, 0.0290 mol), 3-fluorobenzylalcohol (3.65 g, 0.0290 mol) were combined and dissolved in THF (89 mL). The reaction temperature was cooled to 0° C. and DIAD (4.50 g, 0.0290 mol) was added. The reaction was allowed to warm slowly to rt and stirred for 3... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HO- | O.CCOC(=O)C.C1CCOC1 | 0 | 3 | O=[N+]([O-])c1ccc(O)c(Br)c1.OCc1cccc(F)c1>O.CCOC(=O)C.C1CCOC1>O=[N+]([O-])c1ccc(OCc2cccc(F)c2)c(Br)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-84cfa9ac36fc4c0e9c5fcc98d5449fce | CC(C)S(=O)(=O)CC#N>>CC(C)S(=O)(=O)CCN | C(C)(C)S(=O)(=O)CC#N.CSC.B.Cl>>C(C)(C)S(=O)(=O)CCN | [CH3:1][CH:2]([CH3:3])[S:4](=[O:5])(=[O:6])[CH2:7][C:8]#[N:9]>>[CH3:1][CH:2]([CH3:3])[S:4](=[O:5])(=[O:6])[CH2:7][CH2:8][NH2:9] | CC(C)S(=O)(=O)CC#N | CC(C)S(=O)(=O)CCN | null | null | C1CCOC1 | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | null | [#16:1]-[C:2]-[C;H0;D2;+0:3]#[N;H0;D1;+0:4]>>[#16:1]-[C:2]-[CH2;D2;+0:3]-[NH2;D1;+0:4] | null | [] | null | null | 40 | MINUTE | Prepared according to Procedure K. 2-iso-Propylsulfonylacetonitrile (0.50 g, 3.39 mmol) was dissolved in THF and warmed to reflux under N2. Borane dimethylsulfide (2M, 1.7 mL, 3.39 mmol) was added dropwise and the reaction was stirred for an additional 40 minutes at reflux. After cooling the reaction to rt, HCl (2 M in... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | null | null | C1CCOC1 | null | 0.666667 | CC(C)S(=O)(=O)CC#N>C1CCOC1>CC(C)S(=O)(=O)CCN |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c0915fda359f46419f39670b064a7ee8 | Fc1cc2ncnc(Cl)c2cc1I.Nc1ccc(OCc2ccccc2)cc1>>Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1I | Cl.ClC1=NC=NC2=CC(=C(C=C12)I)F.O1CCOCC1.Cl.C(C1=CC=CC=C1)OC1=CC=C(N)C=C1>>Cl.C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC(=C(C=C12)I)F | Cl[c:9]1[n:8][cH:7][n:6][c:5]2[cH:4][c:3]([F:2])[c:27]([I:28])[cH:26][c:25]21.[NH2:10][c:11]1[cH:12][cH:13][c:14]([O:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[cH:23][cH:24]1>>[F:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8][c:9]([NH:10][c:11]3[cH:12][cH:13][c:14]([O:15][CH2:16][c:17]4[cH:18][cH:19][cH:20][cH:21][c... | Fc1cc2ncnc(Cl)c2cc1I.Nc1ccc(OCc2ccccc2)cc1 | Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1I | null | null | ClCCl | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2ccc(Nc3ncnc4ccccc34)cc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 79.1 | [{"value": 79.0, "product": "Cl.C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC(=C(C=C12)I)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.1, "product": "Cl.C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC(=C(C=C12)I)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | null | null | Prepared according to Procedure A from 4-chloro-6-iodo-7-fluoro-quinazoline hydrochloride (4.02 grams, 11.65 mmoles), anhydrous dioxane (70 ml), dichloromethane (20 ml), and 4-benzyloxyaniline hydrochloride (2.83 grams, 12 mmoles). The mixture was stirred and heated to 110° C. (oil bath temperature) for 16 hours, coole... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccccc1.c1ccccc1 | HCl | ClCCl | 110 | null | Fc1cc2ncnc(Cl)c2cc1I.Nc1ccc(OCc2ccccc2)cc1>ClCCl>Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1I |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3a3d79a0ad7b45509b0ca67ec1d79118 | Nc1ccc2c(=O)[nH]cnc2c1.[I-]>>O=c1[nH]cnc2cc(I)ccc12 | NC1=CC=C2C(NC=NC2=C1)=O.[I-].[K+].N(=O)[O-].[Na+]>>IC1=CC=C2C(NC=NC2=C1)=O | N[c:8]1[cH:7][c:6]2[n:5][cH:4][nH:3][c:2](=[O:1])[c:12]2[cH:11][cH:10]1.[I-:9]>>[O:1]=[c:2]1[nH:3][cH:4][n:5][c:6]2[cH:7][c:8]([I:9])[cH:10][cH:11][c:12]12 | Nc1ccc2c(=O)[nH]cnc2c1.[I-] | O=c1[nH]cnc2cc(I)ccc12 | null | null | Cl.O | Functional Group Interconversion | OtherReaction | 1fc01df8cde644f7b4f5f8066e7d4772323840e5c20b07166b24323c5f5d8071 | 9c224743a26d9e1c3135e4817dd611aec414d8ea156f02200a3aef865be78b01 | O=c1[nH]cnc2ccccc12 | N-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[c:5]:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10]:1.[I-;H0;D0:11]>>[I;H0;D1;+0:11]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[c:5]:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10]:1 | 17.8 | [{"value": 17.8, "product": "IC1=CC=C2C(NC=NC2=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 10 | MINUTE | 7-Amino-quinazolin-4-one (R. Dempsy and E. Skito, Biochemistry, 30, 1991, 8480) (1.61 g) was suspended in 6N HCl (20 ml) and cooled in an ice bath. A solution of sodium nitrite (0.75 g) in water (10 ml) was added dropwise over 15 minutes. After a further 10 minutes, a solution of potassium iodide (1.66 g) in water (5 m... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic halide | c1ccc2cncnc2c1 | c1ccc2cncnc2c1 | c1ccc2cncnc2c1 | Other | Cl.O | 20 | 0.166667 | Nc1ccc2c(=O)[nH]cnc2c1.[I-]>Cl.O>O=c1[nH]cnc2cc(I)ccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e84ef08f26484b01b5d0af935816ee99 | O=P(Cl)(Cl)Cl.O=c1[nH]cnc2cc(I)ccc12>>Clc1ncnc2cc(I)ccc12 | IC1=CC=C2C(NC=NC2=C1)=O.P(=O)(Cl)(Cl)Cl>>ClC1=NC=NC2=CC(=CC=C12)I | O=P(Cl)(Cl)[Cl:1].O=[c:2]1[nH:3][cH:4][n:5][c:6]2[cH:7][c:8]([I:9])[cH:10][cH:11][c:12]12>>[Cl:1][c:2]1[n:3][cH:4][n:5][c:6]2[cH:7][c:8]([I:9])[cH:10][cH:11][c:12]12 | O=P(Cl)(Cl)Cl.O=c1[nH]cnc2cc(I)ccc12 | Clc1ncnc2cc(I)ccc12 | null | null | null | Functional Group Interconversion | OtherReaction | 5d38f97f3712b237e9f3fba95a694ccb97b6e400bb6127459a74d91e2bc1ab18 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc2ncncc2c1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9] | null | [] | null | null | null | null | 7-Iodoquinazolin-4-one (0.46 g) was treated with phosphorous oxychloride (5 ml) at reflux under nitrogen for 2 hours. The mixture was cooled, evaporated and partitioned between saturated aqueous sodium carbonate and ethyl acetate. The organic phase was dried and concentrated in vacuo to give the title compound (0.43 g)... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2cncnc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | HCl | null | null | null | O=P(Cl)(Cl)Cl.O=c1[nH]cnc2cc(I)ccc12>>Clc1ncnc2cc(I)ccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e71958687b94441b8c59cbe768660ed2 | Nc1cc(F)ccc1C(=O)O>>Nc1cc(F)c(I)cc1C(=O)O | I(=O)(=O)Cl.I(=O)(=O)Cl.C(C1=CC=CC=C1)[N+](C)(C)C.ClCCl.NC1=C(C(=O)O)C=CC(=C1)F.C(O)([O-])=O.[Na+]>>NC1=C(C(=O)O)C=C(C(=C1)F)I | [NH2:1][c:2]1[cH:3][c:4]([F:5])[cH:6][cH:8][c:9]1[C:10](=[O:11])[OH:12]>>[NH2:1][c:2]1[cH:3][c:4]([F:5])[c:6]([I:7])[cH:8][c:9]1[C:10](=[O:11])[OH:12] | Nc1cc(F)ccc1C(=O)O | Nc1cc(F)c(I)cc1C(=O)O | null | null | CO | Functional Group Addition | Aromatic iodination | 2e63a9b91d60f82a8e59b7c72ed55b9aec048f26be2f5eb9ca65b1b73867743c | 0a2f22058f27970cef4a98a778644dbe9c44e91f66c74cd24db321993177608a | c1ccccc1 | [F;D1;H0:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6]-[C:7](=[O;D1;H0:8])-[O;D1;H1:9]>>[F;D1;H0:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[I;D1;H0:10]):[c:5]:[c:6]-[C:7](=[O;D1;H0:8])-[O;D1;H1:9] | 77 | [{"value": 77.0, "product": "NC1=C(C(=O)O)C=C(C(=C1)F)I", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.0, "product": "NC1=C(C(=O)O)C=C(C(=C1)F)I", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | To a vigorously stirred solution of dichloromethane (700 ml), methanol (320 ml), and 2-amino-4-fluoro-benzoic acid (33.35 grams, 215 mmoles) was added solid sodium hydrogencarbonate (110 grams, 1.31 moles) followed by portion addition of benzyltrimethyl ammonium dichloroiodate (82.5 grams, 237 mmoles). The mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | CO | null | 48 | Nc1cc(F)ccc1C(=O)O>CO>Nc1cc(F)c(I)cc1C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-64991fdfcf894867ba48f50e19e8fc30 | Nc1cc(F)c(I)cc1C(=O)O.O=C(Cl)OC(Cl)(Cl)Cl>>O=c1[nH]c2cc(F)c(I)cc2c(=O)o1 | NC1=C(C(=O)O)C=C(C(=C1)F)I.ClC(Cl)(Cl)OC(=O)Cl>>FC=1C=C2C(C(=O)OC(N2)=O)=CC1I | [NH2:3][c:4]1[cH:5][c:6]([F:7])[c:8]([I:9])[cH:10][c:11]1[C:12](=[O:13])[OH:14].ClC(Cl)(Cl)O[C:2](Cl)=[O:1]>>[O:1]=[c:2]1[nH:3][c:4]2[cH:5][c:6]([F:7])[c:8]([I:9])[cH:10][c:11]2[c:12](=[O:13])[o:14]1 | Nc1cc(F)c(I)cc1C(=O)O.O=C(Cl)OC(Cl)(Cl)Cl | O=c1[nH]c2cc(F)c(I)cc2c(=O)o1 | null | null | O1CCOCC1 | Aromatic Heterocycle Formation | OtherReaction | fc15380ff4d79ccb35bf3855432af73f82f5e67c05b3e399eb4e4e9fc738479c | 1d99fb7140022ceb276e15a64139fff14e6daa2ce5fade57cf77a9575a5ee61e | O=c1[nH]c2ccccc2c(=O)o1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-C(-Cl)(-Cl)-Cl.[NH2;D1;+0:3]-[c:4](:[c:5]):[c:6](-[C;H0;D3;+0:7](=[O;D1;H0:8])-[OH;D1;+0:9]):[c:10]>>[O;D1;H0:8]=[c;H0;D3;+0:7]1:[o;H0;D2;+0:9]:[c;H0;D3;+0:1](=[O;D1;H0:2]):[nH;D2;+0:3]:[c:4](:[c:5]):[c:6]:1:[c:10] | 90.4 | [{"value": 90.0, "product": "FC=1C=C2C(C(=O)OC(N2)=O)=CC1I", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.4, "product": "FC=1C=C2C(C(=O)OC(N2)=O)=CC1I", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Anhydrous dioxane (0.5 liters), 2-amino-4-fluoro-5-iodo-benzoic acid (46 grams, 164 mmoles), and trichloromethylchloroformate (97.4 grams, 492 mmoles) were added to a one liter one neck flask equipped with a magnetic stir bar and reflux condenser. The solution was placed under anhydrous nitrogen, stirred and heated to ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Trichloro group.Carboxylic acid.Ether.Primary amine | null | c1ccccc1 | c1ccc2ncocc2c1 | c1ccc2ncocc2c1 | HCl | O1CCOCC1 | null | null | Nc1cc(F)c(I)cc1C(=O)O.O=C(Cl)OC(Cl)(Cl)Cl>O1CCOCC1>O=c1[nH]c2cc(F)c(I)cc2c(=O)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5d0ea04261c04a4fa54c304df4f44504 | N=CN.O=c1[nH]c2cc(F)c(I)cc2c(=O)o1>>Oc1ncnc2cc(F)c(I)cc12 | FC=1C=C2C(C(=O)OC(N2)=O)=CC1I.C(C)(=O)O.C(=N)N>>OC1=NC=NC2=CC(=C(C=C12)I)F | NC=[NH:3].O=[c:4]1o[c:2](=[O:1])[c:13]2[c:6]([nH:5]1)[cH:7][c:8]([F:9])[c:10]([I:11])[cH:12]2>>[OH:1][c:2]1[n:3][cH:4][n:5][c:6]2[cH:7][c:8]([F:9])[c:10]([I:11])[cH:12][c:13]12 | N=CN.O=c1[nH]c2cc(F)c(I)cc2c(=O)o1 | Oc1ncnc2cc(F)c(I)cc12 | null | null | CN(C=O)C | Miscellaneous | OtherReaction | 1838aa909a592eab94589c7b043b2a6a39303e9443aeb018fb34fd1bc651fb9a | cd196a3cba60b08ae897e4a23847dffdb90adc6b09740a5f115e8d6d87cf6580 | c1ccc2ncncc2c1 | N-C=[NH;D1;+0:1].O=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4](:[c:5]):[c:6](:[c:7]):[c;H0;D3;+0:8](=[O;H0;D1;+0:9]):o:1>>[OH;D1;+0:9]-[c;H0;D3;+0:8]1:[n;H0;D2;+0:1]:[cH;D2;+0:2]:[n;H0;D2;+0:3]:[c:4](:[c:5]):[c:6]:1:[c:7] | 91.2 | [{"value": 91.0, "product": "OC1=NC=NC2=CC(=C(C=C12)I)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.2, "product": "OC1=NC=NC2=CC(=C(C=C12)I)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | null | null | Dimethylformamide (0.5 liters), 4-fluoro-5-iodo-isatoic anhydride (45 grams, 147 mmoles), and formamidine acetate (45.92 grams, 441 mmoles), were combined in a one liter one-neck flask fitted with a magnetic stir bar. The mixture was placed under anhydrous nitrogen and heated at 110° C. for 6 hours. The mixture was all... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic alcohol | c1ccc2ncocc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | HO- | CN(C=O)C | 110 | null | N=CN.O=c1[nH]c2cc(F)c(I)cc2c(=O)o1>CN(C=O)C>Oc1ncnc2cc(F)c(I)cc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aa272606426141039067d7d6ac194e4b | O=S(Cl)Cl.Oc1ncnc2cc(F)c(I)cc12>>Cl.Fc1cc2ncnc(Cl)c2cc1I | S(=O)(Cl)Cl.OC1=NC=NC2=CC(=C(C=C12)I)F>>Cl.ClC1=NC=NC2=CC(=C(C=C12)I)F | O=S([Cl:1])[Cl:10].O[c:9]1[n:8][cH:7][n:6][c:5]2[cH:4][c:3]([F:2])[c:13]([I:14])[cH:12][c:11]21>>[ClH:1].[F:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8][c:9]([Cl:10])[c:11]2[cH:12][c:13]1[I:14] | O=S(Cl)Cl.Oc1ncnc2cc(F)c(I)cc12 | Cl.Fc1cc2ncnc(Cl)c2cc1I | null | null | CN(C=O)C | Functional Group Interconversion | Alcohol to chloride_SOCl2 | b0b0f8b7642d018e3b261231985ddd65d16d4d42cce7aa11791e49c826337b90 | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1ccc2ncncc2c1 | O-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].O=S(-[Cl;H0;D1;+0:9])-[Cl;H0;D1;+0:10]>>[Cl;H0;D1;+0:9]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[ClH;D0;+0:10] | 67 | [{"value": 67.0, "product": "Cl.ClC1=NC=NC2=CC(=C(C=C12)I)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Thionyl chloride (0.6 liters), 4-hydroxy-6-iodo-7-fluoro-quinazoline (36 grams, 124 mmoles), and dimethylformamide (6 ml) were combined in a one liter one-neck flask fitted with a magnetic stir bar. The mixture was placed under anhydrous nitrogen and heated to a gentle reflux for 24 hours. The mixture was allowed to co... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | Other | CN(C=O)C | null | 1 | O=S(Cl)Cl.Oc1ncnc2cc(F)c(I)cc12>CN(C=O)C>Cl.Fc1cc2ncnc(Cl)c2cc1I |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cd84898e135448f9be186b594cda98c8 | O=Cc1csc(Br)n1.OCCO>>Brc1nc(C2OCCO2)cs1 | BrC=1SC=C(N1)C=O.C(CO)O>>BrC=1SC=C(N1)C1OCCO1 | O=[CH:5][c:4]1[n:3][c:2]([Br:1])[s:11][cH:10]1.[OH:6][CH2:7][CH2:8][OH:9]>>[Br:1][c:2]1[n:3][c:4]([CH:5]2[O:6][CH2:7][CH2:8][O:9]2)[cH:10][s:11]1 | O=Cc1csc(Br)n1.OCCO | Brc1nc(C2OCCO2)cs1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | fe0fbb45a87f24c1e456c6b4e41101562cd8f0af3ec376bb6115e7c1555d997b | 7ac65b5a5f576337ce8e86e0130eb9b4757ca21b2419a0e82bbdfd5def30ee73 | c1nc(C2OCCO2)cs1 | O=[CH;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#16;a:5]:[c:6]:1.[OH;D1;+0:7]-[C:8]-[C:9]-[OH;D1;+0:10]>>[#16;a:5]1:[c:6]:[c:2](-[CH;D3;+0:1]2-[O;H0;D2;+0:7]-[C:8]-[C:9]-[O;H0;D2;+0:10]-2):[#7;a:3]:[c:4]:1 | 74.7 | [{"value": 74.7, "product": "BrC=1SC=C(N1)C1OCCO1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Bromothiazole-4-carbaldehyde (6.56 g, 34.17 mmol) [A. T. Ung, S. G. Pyne/Tetrahedron: Asymmetry 9 (1998) 1395-1407] and ethylene glycol (5.72 ml, 102.5 mmol) were heated under reflux in toluene (50 ml), with a Dean and Stark trap fitted, for 18 hr. The product was concentrated and purified by column chromatography (1... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary alcohol.Primary alcohol | Ether.Ether | null | C1COCO1 | c1cscn1.C1COCO1 | HO- | C1(=CC=CC=C1)C | null | null | O=Cc1csc(Br)n1.OCCO>C1(=CC=CC=C1)C>Brc1nc(C2OCCO2)cs1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-56437866bae3485394d7dc67c7dea6c9 | Brc1nc(C2OCCO2)cs1.CCC[CH2][Sn]([Cl])([CH2]CCC)[CH2]CCC>>CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1scnc1C1OCCO1 | C(CCC)[Sn](CCCC)(CCCC)Cl.C(CCC)[Li].CCCCCC.BrC=1SC=C(N1)C1OCCO1>>O1C(OCC1)C=1N=CSC1[Sn](CCCC)(CCCC)CCCC | Br[c:16]1[s:15][cH:14][c:18]([CH:19]2[O:20][CH2:21][CH2:22][O:23]2)[n:17]1.[Cl][Sn:5]([CH2:4][CH2:3][CH2:2][CH3:1])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:10][CH2:11][CH2:12][CH3:13]>>[CH3:1][CH2:2][CH2:3][CH2:4][Sn:5]([CH2:6][CH2:7][CH2:8][CH3:9])([CH2:10][CH2:11][CH2:12][CH3:13])[c:14]1[s:15][cH:16][n:17][c:18]1[CH:19]1[O... | Brc1nc(C2OCCO2)cs1.CCC[CH2][Sn]([Cl])([CH2]CCC)[CH2]CCC | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1scnc1C1OCCO1 | null | null | O.C1CCOC1 | Miscellaneous | OtherReaction | 8ae5fc7f9b4acc2fe8513c129e6d51d0ca2d3187413857a77607588f36f1db43 | 31a273782785992494eb6bb26e7d587fea5a029768e25f39f813b72e5d926c19 | c1nc(C2OCCO2)cs1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[cH;D2;+0:3]:[c:4](-[C:5](-[#8:6])-[#8:7]):[#7;a:8]:1.[C:9]-[C:10]-[Sn;H0;D4;+0:11](-[Cl])(-[C:12]-[C:13])-[C:14]-[C:15]>>[#8:6]-[C:5](-[c:4]1:[#7;a:8]:[cH;D2;+0:1]:[#16;a:2]:[c;H0;D3;+0:3]:1-[Sn;H0;D4;+0:11](-[C:10]-[C:9])(-[C:12]-[C:13])-[C:14]-[C:15])-[#8:7] | 98.1 | [{"value": 98.1, "product": "O1C(OCC1)C=1N=CSC1[Sn](CCCC)(CCCC)CCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Bromo-4-(1,3-dioxolan-2-yl) thiazole (6.4 g, 27.14 mmol) was stirred at −78° C. in dry THF (38 ml). 1.6M n butyl lithium in hexane (18.6 ml, 29.78 mmol) was added dropwise under nitrogen. After 30 min at this temperature, tributyl tin chloride (7.35 ml, 27.14 mmol) was added dropwise. The reaction was allowed to warm... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | Tin | c1cscn1 | c1cscn1 | c1cscn1.C1COCO1 | Br- | O.C1CCOC1 | null | null | Brc1nc(C2OCCO2)cs1.CCC[CH2][Sn]([Cl])([CH2]CCC)[CH2]CCC>O.C1CCOC1>CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1scnc1C1OCCO1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-63b4d822b467409296d0c8becb5d1c70 | Clc1ncnc2ccc(Br)cc12.Nc1ccc(OCc2ccccc2)cc1>>Brc1ccc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2c1.Cl | ClC1=NC=NC2=CC=C(C=C12)Br.C(C1=CC=CC=C1)OC1=CC=C(N)C=C1>>Cl.C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC=C(C=C12)Br | [Br:1][c:2]1[cH:3][cH:4][c:5]2[n:6][cH:7][n:8][c:9]([Cl:27])[c:25]2[cH:26]1.[NH2:10][c:11]1[cH:12][cH:13][c:14]([O:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[cH:23][cH:24]1>>[Br:1][c:2]1[cH:3][cH:4][c:5]2[n:6][cH:7][n:8][c:9]([NH:10][c:11]3[cH:12][cH:13][c:14]([O:15][CH2:16][c:17]4[cH:18][cH:19][cH:20][cH:... | Clc1ncnc2ccc(Br)cc12.Nc1ccc(OCc2ccccc2)cc1 | Brc1ccc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2c1.Cl | null | null | CC(C)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2ccc(Nc3ncnc4ccccc34)cc2)cc1 | [Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[ClH;D0;+0:1].[c:12]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9]):[c:13] | 88.1 | [{"value": 88.0, "product": "Cl.C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC=C(C=C12)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.1, "product": "Cl.C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC=C(C=C12)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Chloro-6-bromoquinazoline (0.25 g, 1.0 mmol) and 4-benzyloxyaniline (0.25 g, 1.3 mmol) were mixed in 2-propanol (6 ml) and heated at reflux for 10 mins (Procedure A). The solution was allowed to cool at room temperature and the 2-propanol removed in vacuo. The resulting solid was triturated with acetone to give the p... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccccc1.c1ccccc1 | null | CC(C)O | null | null | Clc1ncnc2ccc(Br)cc12.Nc1ccc(OCc2ccccc2)cc1>CC(C)O>Brc1ccc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2c1.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5721c1e4a76f4fc6929d7cbd2aa8ea1d | Clc1ncnc2ccc(I)cc12.Nc1ccc(OCc2ccccc2)cc1>>Cl.Ic1ccc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2c1 | ClC1=NC=NC2=CC=C(C=C12)I.C(C1=CC=CC=C1)OC1=CC=C(N)C=C1>>Cl.C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC=C(C=C12)I | [Cl:1][c:10]1[n:9][cH:8][n:7][c:6]2[cH:5][cH:4][c:3]([I:2])[cH:27][c:26]21.[NH2:11][c:12]1[cH:13][cH:14][c:15]([O:16][CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[cH:24][cH:25]1>>[ClH:1].[I:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][n:9][c:10]([NH:11][c:12]3[cH:13][cH:14][c:15]([O:16][CH2:17][c:18]4[cH:19][cH:20][cH:... | Clc1ncnc2ccc(I)cc12.Nc1ccc(OCc2ccccc2)cc1 | Cl.Ic1ccc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2ccc(Nc3ncnc4ccccc34)cc2)cc1 | [Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[ClH;D0;+0:1].[c:12]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9]):[c:13] | 97.4 | [{"value": 97.4, "product": "Cl.C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC=C(C=C12)I", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Chloro-6-iodoquinazoline (8 g) was treated with 4-benzyloxyaniline (5.5 g) in acetonitrile (500 ml) at reflux under N2 for 18 hours. Subsequent cooling and filtration gave the title compound (13.13 g); δH [2H6]-DMSO 11.45 (1H, b, NH), 9.22 (1H, s, 5-H), 8.89 (1H, s, 2-H), 8.36 (1H, d, 7-H), 7.69 (1H, d, 8-H), 7.63 (2... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccccc1.c1ccccc1 | null | C(C)#N | null | null | Clc1ncnc2ccc(I)cc12.Nc1ccc(OCc2ccccc2)cc1>C(C)#N>Cl.Ic1ccc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5b75a1d5ec7f4445a89a32fc91071f80 | Fc1cc2ncnc(Cl)c2cc1I.Nc1ccc(OCc2ccccc2)cc1>>Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1I | Cl.ClC1=NC=NC2=CC(=C(C=C12)I)F.O1CCOCC1.Cl.C(C1=CC=CC=C1)OC1=CC=C(N)C=C1>>Cl.C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC(=C(C=C12)I)F | Cl[c:9]1[n:8][cH:7][n:6][c:5]2[cH:4][c:3]([F:2])[c:27]([I:28])[cH:26][c:25]21.[NH2:10][c:11]1[cH:12][cH:13][c:14]([O:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[cH:23][cH:24]1>>[F:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8][c:9]([NH:10][c:11]3[cH:12][cH:13][c:14]([O:15][CH2:16][c:17]4[cH:18][cH:19][cH:20][cH:21][c... | Fc1cc2ncnc(Cl)c2cc1I.Nc1ccc(OCc2ccccc2)cc1 | Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1I | null | null | ClCCl | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2ccc(Nc3ncnc4ccccc34)cc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 79.1 | [{"value": 79.0, "product": "Cl.C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC(=C(C=C12)I)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.1, "product": "Cl.C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC(=C(C=C12)I)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | null | null | Prepared according to Procedure A from 4-chloro-6-iodo-7-fluoro-quinazoline hydrochloride (4.02 grams, 11.65 mmoles), anhydrous dioxane (70 ml), dichloromethane (20 ml) and 4-benzyloxyaniline hydrochloride (2.83 grams, 12 mmoles). The mixture was stirred and heated to 110° C. (oil bath temperature) for 16 hours. The mi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccccc1.c1ccccc1 | HCl | ClCCl | 110 | null | Fc1cc2ncnc(Cl)c2cc1I.Nc1ccc(OCc2ccccc2)cc1>ClCCl>Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1I |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4eb8ffc78df042a0b02e8d97af8040b1 | Clc1cc2c(Cl)ncnc2cn1.Nc1ccc(OCc2ccccc2)cc1>>Clc1cc2c(Nc3ccc(OCc4ccccc4)cc3)ncnc2cn1 | C(C1=CC=CC=C1)OC1=CC=C(N)C=C1.ClC=1C2=C(N=CN1)C=NC(=C2)Cl>>C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC=1C2=C(N=CN1)C=NC(=C2)Cl | Cl[c:5]1[c:4]2[cH:3][c:2]([Cl:1])[n:26][cH:25][c:24]2[n:23][cH:22][n:21]1.[NH2:6][c:7]1[cH:8][cH:9][c:10]([O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][cH:20]1>>[Cl:1][c:2]1[cH:3][c:4]2[c:5]([NH:6][c:7]3[cH:8][cH:9][c:10]([O:11][CH2:12][c:13]4[cH:14][cH:15][cH:16][cH:17][cH:18]4)[cH:19][cH:20]3)[n:2... | Clc1cc2c(Cl)ncnc2cn1.Nc1ccc(OCc2ccccc2)cc1 | Clc1cc2c(Nc3ccc(OCc4ccccc4)cc3)ncnc2cn1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | d7e80981ec4355d1692da3210ded123ee4151f1f202c481ca7dd6b10037b54ac | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2ccc(Nc3ncnc4cnccc34)cc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[#7;a:7]:[c:8]:[c:9]:[c:10]:2:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[c:13]:[c:12](-[NH;D2;+0:11]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[#7;a:7]:[c:8]:[c:9]:[c:10]:2:1):[c:14] | null | [] | null | null | null | null | Prepared according to Procedure A from 4-benzyloxyaniline (1 eq) and 4,6-dichloro-pyrido[3,4-d]pyrimidine (1 eq); δH (CDCl3) 9.11 (1H, s), 8.78 (1H, s), 7.75 (1H, d), 7.56 (2H, dd), 7.40 (5H, m), 7.15 (2H, d), 5.10 (2H, s); m/z (M+1)+ 409.
Conditions: See reaction.notes.procedure_details.
Workup: Prepared | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cc2cncnc2cn1 | c1cc2cncnc2cn1 | c1ccccc1.c1ccccc1.c1cc2cncnc2cn1 | HCl | null | null | null | Clc1cc2c(Cl)ncnc2cn1.Nc1ccc(OCc2ccccc2)cc1>>Clc1cc2c(Nc3ccc(OCc4ccccc4)cc3)ncnc2cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9d6c83f1286a4209b201e4b7de8c1990 | Clc1cc2c(Cl)ncnc2cn1.Nc1ccc(OCc2cccc(F)c2)cc1>>Fc1cccc(COc2ccc(Nc3ncnc4cnc(Cl)cc34)cc2)c1 | ClC=1C2=C(N=CN1)C=NC(=C2)Cl.FC=1C=C(COC2=CC=C(N)C=C2)C=CC1>>ClC1=CC2=C(N=CN=C2NC2=CC=C(C=C2)OCC2=CC(=CC=C2)F)C=N1 | Cl[c:14]1[n:15][cH:16][n:17][c:18]2[cH:19][n:20][c:21]([Cl:22])[cH:23][c:24]12.[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]([NH2:13])[cH:25][cH:26]2)[cH:27]1>>[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]([NH:13][c:14]3[n:15][cH:16][n:17][c:18]4[cH:19][n:20][c:21... | Clc1cc2c(Cl)ncnc2cn1.Nc1ccc(OCc2cccc(F)c2)cc1 | Fc1cccc(COc2ccc(Nc3ncnc4cnc(Cl)cc34)cc2)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | d7e80981ec4355d1692da3210ded123ee4151f1f202c481ca7dd6b10037b54ac | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2ccc(Nc3ncnc4cnccc34)cc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[#7;a:7]:[c:8]:[c:9]:[c:10]:2:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[c:13]:[c:12](-[NH;D2;+0:11]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[#7;a:7]:[c:8]:[c:9]:[c:10]:2:1):[c:14] | null | [] | null | null | null | null | 4,6-Dichloro-pyrido[3,4-d]pyrimidine (1 g) and 4-(3-fluorobenzyloxy)aniline (1.08 g) in acetonitrile (70 ml) were reacted together as in Procedure A. The product was collected by filtration as a yellow solid (1.86 g); m/z 381 (M+1)+.
Conditions: See reaction.notes.procedure_details.
Workup: The product was collected by... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cc2cncnc2cn1 | c1cc2cncnc2cn1 | c1ccccc1.c1ccccc1.c1cc2cncnc2cn1 | HCl | C(C)#N | null | null | Clc1cc2c(Cl)ncnc2cn1.Nc1ccc(OCc2cccc(F)c2)cc1>C(C)#N>Fc1cccc(COc2ccc(Nc3ncnc4cnc(Cl)cc34)cc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ea80a43be70d4a02b2f0bd9da4ad0f18 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccc(C2OCCO2)o1.Clc1cc2c(Nc3ccc(OCc4ccccc4)cc3)ncnc2cn1>>O=Cc1ccc(-c2cc3c(Nc4ccc(OCc5ccccc5)cc4)ncnc3cn2)o1 | C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC=1C2=C(N=CN1)C=NC(=C2)Cl.O1C(OCC1)C1=CC=C(O1)[Sn](CCCC)(CCCC)CCCC>>C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC=1C2=C(N=CN1)C=NC(=C2)C2=CC=C(O2)C=O | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c:6]1[cH:5][cH:4][c:3]([CH:2]2OCC[O:1]2)[o:32]1.Cl[c:7]1[cH:8][c:9]2[c:10]([NH:11][c:12]3[cH:13][cH:14][c:15]([O:16][CH2:17][c:18]4[cH:19][cH:20][cH:21][cH:22][cH:23]4)[cH:24][cH:25]3)[n:26][cH:27][n:28][c:29]2[cH:30][n:31]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[c:10]... | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccc(C2OCCO2)o1.Clc1cc2c(Nc3ccc(OCc4ccccc4)cc3)ncnc2cn1 | O=Cc1ccc(-c2cc3c(Nc4ccc(OCc5ccccc5)cc4)ncnc3cn2)o1 | null | null | Cl | Acylation | OtherReaction | cdcdbab2b874eab9bcd20f9243c192f8716be48b5b517ff2a103a9676e9c5a97 | f78ef97212accf10523047d1c7ef9c894dcd3eff344da65f910d057d1373fa81 | c1ccc(COc2ccc(Nc3ncnc4cnc(-c5ccco5)cc34)cc2)cc1 | C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[c;H0;D3;+0:1]1:[#8;a:2]:[c:3](-[CH;D3;+0:4]2-O-C-C-[O;H0;D2;+0:5]-2):[c:6]:[c:7]:1.Cl-[c;H0;D3;+0:8]1:[#7;a:9]:[c:10]:[c:11](:[#7;a:12]):[c:13](:[c:14]:[#7;a:15]):[c:16]:1>>[#7;a:15]:[c:14]:[c:13]1:[c:16]:[c;H0;D3;+0:8](-[c;H0;D3;+0:1]2:[#8;a:2]:[c:3](-[CH;D2;+0:4]=[O;H0;D1... | 52 | [{"value": 52.0, "product": "C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC=1C2=C(N=CN1)C=NC(=C2)C2=CC=C(O2)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.9, "product": "C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC=1C2=C(N=CN1)C=NC(=C2)C2=CC=C(O2)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | (4-Benzyloxyphenyl)-(6-chloro-pyrido[3,4-d]pyrimidin-4-yl)-amine (4.0 g, 11.0 mmol), 5-(1,3-dioxolan-2-yl)-2-(tributylstannyl)furan (J. Chem. Soc., Chem. Commun., (1988), 560) (6.0 g, 14.0 mmol) were reacted together in a procedure analogous to Procedure B above for 20 hrs. The reaction mixture was allowed to cool, 1N ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Ether.Tin | Aldehyde | c1ccoc1.C1COCO1.c1cc2cncnc2cn1 | c1ccoc1.c1cc2cncnc2cn1 | c1ccoc1.c1ccccc1.c1ccccc1.c1cc2cncnc2cn1 | HCl.Sn | Cl | null | 0.25 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccc(C2OCCO2)o1.Clc1cc2c(Nc3ccc(OCc4ccccc4)cc3)ncnc2cn1>Cl>O=Cc1ccc(-c2cc3c(Nc4ccc(OCc5ccccc5)cc4)ncnc3cn2)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ea06867e429e4c2a914049177abe4861 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccc(C2OCCO2)o1.Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1I>>Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1-c1ccc(C2OCCO2)o1 | Cl.C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC(=C(C=C12)I)F.O1C(OCC1)C1=CC=C(O1)[Sn](CCCC)(CCCC)CCCC.C(C)(C)N(CC)C(C)C>>C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC(=C(C=C12)C=1OC(=CC1)C1OCCO1)F | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c:27]1[cH:28][cH:29][c:30]([CH:31]2[O:32][CH2:33][CH2:34][O:35]2)[o:36]1.I[c:26]1[c:2]([F:1])[cH:3][c:4]2[n:5][cH:6][n:7][c:8]([NH:9][c:10]3[cH:11][cH:12][c:13]([O:14][CH2:15][c:16]4[cH:17][cH:18][cH:19][cH:20][cH:21]4)[cH:22][cH:23]3)[c:24]2[cH:25]1>>[F:1][c:2]1[cH:3][c:4]2[n:5][cH:6][... | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccc(C2OCCO2)o1.Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1I | Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1-c1ccc(C2OCCO2)o1 | null | null | CN(C)C=O | C-C Coupling | Stille reaction_aryl | e0837286282948e252601463def8f2065b37315796eaf567e28dfdae8becb931 | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | c1ccc(COc2ccc(Nc3ncnc4ccc(-c5ccc(C6OCCO6)o5)cc34)cc2)cc1 | C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[c;H0;D3;+0:1]1:[#8;a:2]:[c:3]:[c:4]:[c:5]:1.I-[c;H0;D3;+0:6]1:[c:7]:[c:8](:[c:9]:[#7;a:10]):[c:11](:[#7;a:12]):[c:13]:[c:14]:1-[F;D1;H0:15]>>[#7;a:12]:[c:11]1:[c:13]:[c:14](-[F;D1;H0:15]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1]2:[#8;a:2]:[c:3]:[c:4]:[c:5]:2):[c:7]:[c:8]:1:[c:9]:[#7;... | 59.4 | [{"value": 59.0, "product": "C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC(=C(C=C12)C=1OC(=CC1)C1OCCO1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.4, "product": "C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC(=C(C=C12)C=1OC(=CC1)C1OCCO1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 4 | HOUR | Synthesized according to Procedure B from a solution of (4-benzyloxyphenyl)-(6-iodo-7-fluoro-quinazolin-4-yl)-amine hydrochloride (508 mg, 1 mmole), 5-(1,3-dioxolan-2-yl)-2-(tributylstannyl)furan (645 mg, 1.5 mmole), diisopropylethyl amine (650 mg, 5 mmole), and dichlorobis(triphenylphosphine) palladium (140 mg, 0.2 mm... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1ccoc1.c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccoc1 | c1ccc2ncncc2c1.c1ccccc1.c1ccccc1.c1ccoc1.C1COCO1 | HI.Sn | CN(C)C=O | 100 | 4 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccc(C2OCCO2)o1.Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1I>CN(C)C=O>Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1-c1ccc(C2OCCO2)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-261499ef120d4f99880e16c991815951 | Brc1ccc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2c1.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccc(C2OCCO2)o1>>c1ccc(COc2ccc(Nc3ncnc4ccc(-c5ccc(C6OCCO6)o5)cc34)cc2)cc1 | C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC=C(C=C12)Br.O1C(OCC1)C1=CC=C(O1)[Sn](CCCC)(CCCC)CCCC>>C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC=C(C=C12)C=1OC(=CC1)C1OCCO1 | Br[c:19]1[cH:18][cH:17][c:16]2[n:15][cH:14][n:13][c:12]([NH:11][c:10]3[cH:9][cH:8][c:7]([O:6][CH2:5][c:4]4[cH:3][cH:2][cH:1][cH:35][cH:34]4)[cH:33][cH:32]3)[c:31]2[cH:30]1.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c:20]1[cH:21][cH:22][c:23]([CH:24]2[O:25][CH2:26][CH2:27][O:28]2)[o:29]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][O:6][c:7... | Brc1ccc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2c1.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccc(C2OCCO2)o1 | c1ccc(COc2ccc(Nc3ncnc4ccc(-c5ccc(C6OCCO6)o5)cc34)cc2)cc1 | null | null | O1CCOCC1 | C-C Coupling | Stille reaction_aryl | e0837286282948e252601463def8f2065b37315796eaf567e28dfdae8becb931 | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | c1ccc(COc2ccc(Nc3ncnc4ccc(-c5ccc(C6OCCO6)o5)cc34)cc2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6](:[c:7]:[#7;a:8]):[c:9]:1.C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[c;H0;D3;+0:10]1:[#8;a:11]:[c:12]:[c:13]:[c:14]:1>>[#7;a:8]:[c:7]:[c:6]1:[c:9]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10]2:[#8;a:11]:[c:12]:[c:13]:[c:14]:2):[c:2]:[c:3]:[c:4]:1:[#7;a:5] | 62.1 | [{"value": 62.0, "product": "C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC=C(C=C12)C=1OC(=CC1)C1OCCO1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.1, "product": "C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC=C(C=C12)C=1OC(=CC1)C1OCCO1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Prepared according to Procedure B from (4-benzyloxy-phenyl)-(6-bromoquinazolin-4-yl)-amine (1.5 g, 3.7 mmol) and 5-(1,3-dioxolan-2-yl)-2-(tributylstannyl)-furan (1.9 g, 4.42 mmol) dissolved in dioxan (30 ml) and heated at reflux under nitrogen for 6 hr. The solvent was removed from the cooled reaction under vacuum, and... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1ccc2ncncc2c1.c1ccoc1 | c1ccc2ncncc2c1.c1ccoc1 | c1ccccc1.c1ccccc1.c1ccc2ncncc2c1.c1ccoc1.C1COCO1 | HBr.Sn | O1CCOCC1 | null | null | Brc1ccc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2c1.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccc(C2OCCO2)o1>O1CCOCC1>c1ccc(COc2ccc(Nc3ncnc4ccc(-c5ccc(C6OCCO6)o5)cc34)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-37de25e5c46d421ba1adb5e7407917c3 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccc(C2OCCO2)o1.Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1I>>Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1-c1ccc(C2OCCO2)o1 | Cl.C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC(=C(C=C12)I)F.O1C(OCC1)C1=CC=C(O1)[Sn](CCCC)(CCCC)CCCC.C(C)(C)N(CC)C(C)C>>C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC(=C(C=C12)C=1OC(=CC1)C1OCCO1)F | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c:27]1[cH:28][cH:29][c:30]([CH:31]2[O:32][CH2:33][CH2:34][O:35]2)[o:36]1.I[c:26]1[c:2]([F:1])[cH:3][c:4]2[n:5][cH:6][n:7][c:8]([NH:9][c:10]3[cH:11][cH:12][c:13]([O:14][CH2:15][c:16]4[cH:17][cH:18][cH:19][cH:20][cH:21]4)[cH:22][cH:23]3)[c:24]2[cH:25]1>>[F:1][c:2]1[cH:3][c:4]2[n:5][cH:6][... | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccc(C2OCCO2)o1.Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1I | Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1-c1ccc(C2OCCO2)o1 | null | null | CN(C)C=O | C-C Coupling | Stille reaction_aryl | e0837286282948e252601463def8f2065b37315796eaf567e28dfdae8becb931 | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | c1ccc(COc2ccc(Nc3ncnc4ccc(-c5ccc(C6OCCO6)o5)cc34)cc2)cc1 | C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[c;H0;D3;+0:1]1:[#8;a:2]:[c:3]:[c:4]:[c:5]:1.I-[c;H0;D3;+0:6]1:[c:7]:[c:8](:[c:9]:[#7;a:10]):[c:11](:[#7;a:12]):[c:13]:[c:14]:1-[F;D1;H0:15]>>[#7;a:12]:[c:11]1:[c:13]:[c:14](-[F;D1;H0:15]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1]2:[#8;a:2]:[c:3]:[c:4]:[c:5]:2):[c:7]:[c:8]:1:[c:9]:[#7;... | 59.4 | [{"value": 59.0, "product": "C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC(=C(C=C12)C=1OC(=CC1)C1OCCO1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.4, "product": "C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC(=C(C=C12)C=1OC(=CC1)C1OCCO1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 4 | HOUR | Prepared according to Procedure B from a solution of (4-benzyloxyphenyl)-(6-iodo-7-fluoro-quinazolin-4-yl)-amine hydrochloride (508 mg, 1 mmole), 5-(1,3-dioxolan-2-yl)-2-(tributylstannyl)furan (645 mg, 1.5 mmole), diisopropylethyl amine (650 mg, 5 mmole), and dichlorobis(triphenylphosphine) palladium (140 mg, 0.2 mmole... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1ccoc1.c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccoc1 | c1ccc2ncncc2c1.c1ccccc1.c1ccccc1.c1ccoc1.C1COCO1 | HI.Sn | CN(C)C=O | 100 | 4 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccc(C2OCCO2)o1.Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1I>CN(C)C=O>Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1-c1ccc(C2OCCO2)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5db03f0cb45d47f0a963ea66a832be3a | CS(=O)(=O)CC(=O)O.NCCc1nc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)cs1>>CS(=O)(=O)CC(=O)NCCc1nc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)cs1 | FC=1C=C(COC2=C(C=C(C=C2)NC2=NC=NC3=CC=C(C=C23)C=2N=C(SC2)CCN)Cl)C=CC1.CS(=O)(=O)CC(=O)O.Cl.CN(CCCN=C=NCC)C>>FC=1C=C(COC2=C(C=C(C=C2)NC2=NC=NC3=CC=C(C=C23)C=2N=C(SC2)CCNC(CS(=O)(=O)C)=O)Cl)C=CC1 | O[C:6]([CH2:5][S:2]([CH3:1])(=[O:3])=[O:4])=[O:7].[NH2:8][CH2:9][CH2:10][c:11]1[n:12][c:13](-[c:14]2[cH:15][cH:16][c:17]3[n:18][cH:19][n:20][c:21]([NH:22][c:23]4[cH:24][cH:25][c:26]([O:27][CH2:28][c:29]5[cH:30][cH:31][cH:32][c:33]([F:34])[cH:35]5)[c:36]([Cl:37])[cH:38]4)[c:39]3[cH:40]2)[cH:41][s:42]1>>[CH3:1][S:2](=[O:... | CS(=O)(=O)CC(=O)O.NCCc1nc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)cs1 | CS(=O)(=O)CC(=O)NCCc1nc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)cs1 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(COc2ccc(Nc3ncnc4ccc(-c5cscn5)cc34)cc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#16:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[#16:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6]-[C:5] | null | [] | null | null | null | null | (4-(3-Fluorobenzyloxy)-3-chlorophenyl)-(6-(2-(2-aminoethyl)-thiazol-4-yl)-quinazolin-4-yl)-amine (0.229 mmol) was reacted with methanesulfonyl acetic acid (0.252 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.252 mmol) in DMF as outlined in procedure (I) to provide the title compound after pur... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1cscn1.c1ccc2ncncc2c1.c1ccccc1.c1ccccc1 | HO- | CN(C)C=O | null | null | CS(=O)(=O)CC(=O)O.NCCc1nc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)cs1>CN(C)C=O>CS(=O)(=O)CC(=O)NCCc1nc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)cs1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-820c155a3521434c8887668407972660 | CS(=O)(=O)CC(=O)O.NCCc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1>>CS(=O)(=O)CC(=O)NCCc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1 | C(C)(C)N(C(C)C)CC.FC=1C=C(COC2=C(C=C(C=C2)NC2=NC=NC3=CC=C(C=C23)C=2OC(=CC2)CCN)Cl)C=CC1.CS(=O)(=O)CC(=O)O.Cl.CN(CCCN=C=NCC)C>>FC=1C=C(COC2=C(C=C(C=C2)NC2=NC=NC3=CC=C(C=C23)C=2OC(=CC2)CCNC(CS(=O)(=O)C)=O)Cl)C=CC1 | O[C:6]([CH2:5][S:2]([CH3:1])(=[O:3])=[O:4])=[O:7].[NH2:8][CH2:9][CH2:10][c:11]1[cH:12][cH:13][c:14](-[c:15]2[cH:16][cH:17][c:18]3[n:19][cH:20][n:21][c:22]([NH:23][c:24]4[cH:25][cH:26][c:27]([O:28][CH2:29][c:30]5[cH:31][cH:32][cH:33][c:34]([F:35])[cH:36]5)[c:37]([Cl:38])[cH:39]4)[c:40]3[cH:41]2)[o:42]1>>[CH3:1][S:2](=[O... | CS(=O)(=O)CC(=O)O.NCCc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1 | CS(=O)(=O)CC(=O)NCCc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(COc2ccc(Nc3ncnc4ccc(-c5ccco5)cc34)cc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#16:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[#16:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6]-[C:5] | null | [] | null | null | null | null | Preparation according to Procedure (I) utilizing (4-(3-fluorobenzyloxy)-3-chlorophenyl)-(6-(5-(2-aminoethyl)-furan-2-yl)-quinazolin-4-yl)-amine (26 mg, 0.0537 mmol), methanesulfonylacetic acid (22.2 mg, 0.161 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (30.0 mg, 0.161 mmol) and N,N-diisopropyleth... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccoc1.c1ccc2ncncc2c1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CS(=O)(=O)CC(=O)O.NCCc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1>>CS(=O)(=O)CC(=O)NCCc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d82e072b327549069d8f27e463500197 | Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1-c1ccc(C2OCCO2)o1>>O=Cc1ccc(-c2cc3c(Nc4ccc(OCc5ccccc5)cc4)ncnc3cc2F)o1 | C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC(=C(C=C12)C=1OC(=CC1)C1OCCO1)F.Cl>>Cl.C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC(=C(C=C12)C1=CC=C(O1)C=O)F | C1C[O:2][CH:3]([c:4]2[cH:5][cH:6][c:7](-[c:8]3[cH:9][c:10]4[c:11]([NH:12][c:13]5[cH:14][cH:15][c:16]([O:17][CH2:18][c:19]6[cH:20][cH:21][cH:22][cH:23][cH:24]6)[cH:25][cH:26]5)[n:27][cH:28][n:29][c:30]4[cH:31][c:32]3[F:33])[o:34]2)O1>>[O:2]=[CH:3][c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][c:10]3[c:11]([NH:12][c:13]4[cH:14][c... | Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1-c1ccc(C2OCCO2)o1 | O=Cc1ccc(-c2cc3c(Nc4ccc(OCc5ccccc5)cc4)ncnc3cc2F)o1 | null | null | C1CCOC1 | Miscellaneous | Acetal hydrolysis to aldehyde | f12636b09f9df336ccc8fe82b927db0e267bccc7cae0970f1f91c7ceed085225 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | c1ccc(COc2ccc(Nc3ncnc4ccc(-c5ccco5)cc34)cc2)cc1 | [c:1]:[c:2](-[CH;D3;+0:3]1-O-C-C-[O;H0;D2;+0:4]-1):[#8;a:5]:[c:6]>>[O;H0;D1;+0:4]=[CH;D2;+0:3]-[c:2](:[c:1]):[#8;a:5]:[c:6] | 61 | [{"value": 61.0, "product": "Cl.C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC(=C(C=C12)C1=CC=C(O1)C=O)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 90 | MINUTE | Prepared according to Procedure C from a stirred solution of (4-benzyloxyphenyl)-(6-(5-(1,3-dioxolan-2-yl)-furan-2-yl)-7-fluoro-quinazolin-4-yl)-amine (0.51 grams, 1.1 mmol) in 20 ml of THF was added 5 ml of 1 N HCl. After stirring for 90 minutes, the resultant suspension was filtered and washed with diethyl ether (200... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | C1COCO1 | null | c1ccoc1.c1ccccc1.c1ccccc1.c1ccc2ncncc2c1 | HO- | C1CCOC1 | null | 1.5 | Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1-c1ccc(C2OCCO2)o1>C1CCOC1>O=Cc1ccc(-c2cc3c(Nc4ccc(OCc5ccccc5)cc4)ncnc3cc2F)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f05a725eab7c438c8529b98fce520eda | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccc(C2OCCO2)o1.Fc1cccc(COc2ccc(Nc3ncnc4cnc(Cl)cc34)cc2)c1>>Fc1cccc(COc2ccc(Nc3ncnc4cnc(-c5ccc(C6OCCO6)o5)cc34)cc2)c1 | ClC1=CC2=C(N=CN=C2NC2=CC=C(C=C2)OCC2=CC(=CC=C2)F)C=N1.O1C(OCC1)C1=CC=C(O1)[Sn](CCCC)(CCCC)CCCC>>O1C(OCC1)C1=CC=C(O1)C1=CC2=C(N=CN=C2NC2=CC=C(C=C2)OCC2=CC(=CC=C2)F)C=N1 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c:22]1[cH:23][cH:24][c:25]([CH:26]2[O:27][CH2:28][CH2:29][O:30]2)[o:31]1.Cl[c:21]1[n:20][cH:19][c:18]2[n:17][cH:16][n:15][c:14]([NH:13][c:12]3[cH:11][cH:10][c:9]([O:8][CH2:7][c:6]4[cH:5][cH:4][cH:3][c:2]([F:1])[cH:36]4)[cH:35][cH:34]3)[c:33]2[cH:32]1>>[F:1][c:2]1[cH:3][cH:4][cH:5][c:6](... | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccc(C2OCCO2)o1.Fc1cccc(COc2ccc(Nc3ncnc4cnc(Cl)cc34)cc2)c1 | Fc1cccc(COc2ccc(Nc3ncnc4cnc(-c5ccc(C6OCCO6)o5)cc34)cc2)c1 | null | null | O1CCOCC1 | C-C Coupling | Stille reaction_aryl | ae92753133f40dafb22d85bdbe2fa24b7eeb98432119f995c0a0fbd50f7dd9fc | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | c1ccc(COc2ccc(Nc3ncnc4cnc(-c5ccc(C6OCCO6)o5)cc34)cc2)cc1 | C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[c;H0;D3;+0:1]1:[#8;a:2]:[c:3]:[c:4]:[c:5]:1.Cl-[c;H0;D3;+0:6]1:[#7;a:7]:[c:8]:[c:9](:[#7;a:10]):[c:11](:[c:12]:[#7;a:13]):[c:14]:1>>[#7;a:13]:[c:12]:[c:11]1:[c:14]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1]2:[#8;a:2]:[c:3]:[c:4]:[c:5]:2):[#7;a:7]:[c:8]:[c:9]:1:[#7;a:10] | null | [] | null | null | null | null | (6-Chloropyrido[3,4-d]pyrimidin-4-yl)-(4-(3-fluorobenzyloxy)-phenyl)-amine (1.85 g) and 5-(1,3-dioxolan-2-yl)-2-(tributylstannyl)-furan (3.82 g) in dioxan (40 ml) were reacted together as in Procedure B. The mixture was evaporated and the residue suspended in dichloromethane. This was then filtered through Celite® and ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1ccoc1.c1cc2cncnc2cn1 | c1cc2cncnc2cn1.c1ccoc1 | c1ccccc1.c1ccccc1.c1cc2cncnc2cn1.c1ccoc1.C1COCO1 | HCl.Sn | O1CCOCC1 | null | null | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccc(C2OCCO2)o1.Fc1cccc(COc2ccc(Nc3ncnc4cnc(Cl)cc34)cc2)c1>O1CCOCC1>Fc1cccc(COc2ccc(Nc3ncnc4cnc(-c5ccc(C6OCCO6)o5)cc34)cc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-05a12bc8eff44c8ebfd4f6e508de1e06 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cc(C=O)co1.Fc1cccc(COc2ccc(Nc3ncnc4cnc(Cl)cc34)cc2)c1>>O=Cc1coc(-c2cc3c(Nc4ccc(OCc5cccc(F)c5)cc4)ncnc3cn2)c1 | ClC1=CC2=C(N=CN=C2NC2=CC=C(C=C2)OCC2=CC(=CC=C2)F)C=N1.C(CCC)[Sn](C1=CC(=CO1)C=O)(CCCC)CCCC>>FC=1C=C(COC2=CC=C(C=C2)NC=2C3=C(N=CN2)C=NC(=C3)C3=CC(=CO3)C=O)C=CC1 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c:6]1[o:5][cH:4][c:3]([CH:2]=[O:1])[cH:33]1.Cl[c:7]1[cH:8][c:9]2[c:10]([NH:11][c:12]3[cH:13][cH:14][c:15]([O:16][CH2:17][c:18]4[cH:19][cH:20][cH:21][c:22]([F:23])[cH:24]4)[cH:25][cH:26]3)[n:27][cH:28][n:29][c:30]2[cH:31][n:32]1>>[O:1]=[CH:2][c:3]1[cH:4][o:5][c:6](-[c:7]2[cH:8][c:9]3[c:1... | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cc(C=O)co1.Fc1cccc(COc2ccc(Nc3ncnc4cnc(Cl)cc34)cc2)c1 | O=Cc1coc(-c2cc3c(Nc4ccc(OCc5cccc(F)c5)cc4)ncnc3cn2)c1 | null | null | O1CCOCC1 | C-C Coupling | Stille reaction_aryl | ae92753133f40dafb22d85bdbe2fa24b7eeb98432119f995c0a0fbd50f7dd9fc | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | c1ccc(COc2ccc(Nc3ncnc4cnc(-c5ccco5)cc34)cc2)cc1 | C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[c;H0;D3;+0:1]1:[#8;a:2]:[c:3]:[c:4](-[C:5]=[O;D1;H0:6]):[c:7]:1.Cl-[c;H0;D3;+0:8]1:[#7;a:9]:[c:10]:[c:11](:[#7;a:12]):[c:13](:[c:14]:[#7;a:15]):[c:16]:1>>[#7;a:15]:[c:14]:[c:13]1:[c:16]:[c;H0;D3;+0:8](-[c;H0;D3;+0:1]2:[#8;a:2]:[c:3]:[c:4](-[C:5]=[O;D1;H0:6]):[c:7]:2):[#7;a:... | null | [] | null | null | null | null | (6-Chloropyrido[3,4-d]pyrimidin-4-yl)-(4-(3-fluorobenzyloxy)-phenyl)-amine (1 g) and 5-(tributylstannyl)-furan-3-carbaldehyde (J. Org. Chem. (1992), 57(11), 3126-31) (1.84 g) in dioxan (35 ml) were reacted together as in Procedure B. The solvent was evaporated and the residue suspended in dichloromethane. The mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1ccoc1.c1cc2cncnc2cn1 | c1ccoc1.c1cc2cncnc2cn1 | c1ccoc1.c1ccccc1.c1ccccc1.c1cc2cncnc2cn1 | HCl.Sn | O1CCOCC1 | null | null | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cc(C=O)co1.Fc1cccc(COc2ccc(Nc3ncnc4cnc(Cl)cc34)cc2)c1>O1CCOCC1>O=Cc1coc(-c2cc3c(Nc4ccc(OCc5cccc(F)c5)cc4)ncnc3cn2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8c071e9768b54febb39ea7d4c1e183fa | CCOC(=O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5ccccc5)c(Cl)c4)c3c2)o1>>O=C(O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5ccccc5)c(Cl)c4)c3c2)o1 | C(C1=CC=CC=C1)OC1=C(C=C(NC2=NC=NC3=CC=C(C=C23)C2=CC=C(O2)C=CC(=O)OCC)C=C1)Cl.[OH-].[Na+]>>C(C1=CC=CC=C1)OC1=C(C=C(NC2=NC=NC3=CC=C(C=C23)C2=CC=C(O2)C=CC(=O)O)C=C1)Cl | CC[O:3][C:2](=[O:1])[CH:4]=[CH:5][c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][c:13]3[n:14][cH:15][n:16][c:17]([NH:18][c:19]4[cH:20][cH:21][c:22]([O:23][CH2:24][c:25]5[cH:26][cH:27][cH:28][cH:29][cH:30]5)[c:31]([Cl:32])[cH:33]4)[c:34]3[cH:35]2)[o:36]1>>[O:1]=[C:2]([OH:3])[CH:4]=[CH:5][c:6]1[cH:7][cH:8][c:9](-[c:10]2[c... | CCOC(=O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5ccccc5)c(Cl)c4)c3c2)o1 | O=C(O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5ccccc5)c(Cl)c4)c3c2)o1 | null | null | C1CCOC1.C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(COc2ccc(Nc3ncnc4ccc(-c5ccco5)cc34)cc2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]=[C:5]-[c:6]:[#8;a:7]>>[#8;a:7]:[c:6]-[C:5]=[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 102.4 | [{"value": 102.4, "product": "C(C1=CC=CC=C1)OC1=C(C=C(NC2=NC=NC3=CC=C(C=C23)C2=CC=C(O2)C=CC(=O)O)C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Prepared according to Procedure H utilizing ethyl 3-(5-{4-[4-(benzyloxy)-3-chloroanilino]-6-quinazolinyl}-2-furyl)-2-propenoate (0.65 g) and aqueous sodium hydroxide (2M, 4 mL) in THF (8 mL) and ethanol (4 mL) to afford the title compound (0.63 g). Electrospray MS m/z 498 (MH+).
Conditions: See reaction.notes.procedure... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccoc1.c1ccc2ncncc2c1.c1ccccc1.c1ccccc1 | Other | C1CCOC1.C(C)O | null | null | CCOC(=O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5ccccc5)c(Cl)c4)c3c2)o1>C1CCOC1.C(C)O>O=C(O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5ccccc5)c(Cl)c4)c3c2)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8363691ec54747d28cff1a88a94a9e84 | CCOC(=O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1>>O=C(O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1 | FC=1C=C(COC2=C(C=C(NC3=NC=NC4=CC=C(C=C34)C3=CC=C(O3)C=CC(=O)OCC)C=C2)Cl)C=CC1.[OH-].[Na+]>>FC=1C=C(COC2=C(C=C(NC3=NC=NC4=CC=C(C=C34)C3=CC=C(O3)C=CC(=O)O)C=C2)Cl)C=CC1 | CC[O:3][C:2](=[O:1])[CH:4]=[CH:5][c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][c:13]3[n:14][cH:15][n:16][c:17]([NH:18][c:19]4[cH:20][cH:21][c:22]([O:23][CH2:24][c:25]5[cH:26][cH:27][cH:28][c:29]([F:30])[cH:31]5)[c:32]([Cl:33])[cH:34]4)[c:35]3[cH:36]2)[o:37]1>>[O:1]=[C:2]([OH:3])[CH:4]=[CH:5][c:6]1[cH:7][cH:8][c:9](-[c... | CCOC(=O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1 | O=C(O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1 | null | null | C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(COc2ccc(Nc3ncnc4ccc(-c5ccco5)cc34)cc2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]=[C:5]-[c:6]:[#8;a:7]>>[#8;a:7]:[c:6]-[C:5]=[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 97 | [{"value": 97.0, "product": "FC=1C=C(COC2=C(C=C(NC3=NC=NC4=CC=C(C=C34)C3=CC=C(O3)C=CC(=O)O)C=C2)Cl)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Prepared according to Procedure H utilizing ethyl 3-(5-{4-[4-(3-fluorobenzyloxy)-3-chloroanilino]-6-quinazolinyl}-2-furyl)-2-propenoate (0.50 g) and aqueous sodium hydroxide (2M, 2 mL) in THF (6 mL) to afford the title compound (0.46 g). Electrospray MS m/z 516 (MH+).
Conditions: See reaction.notes.procedure_details.
W... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccoc1.c1ccc2ncncc2c1.c1ccccc1.c1ccccc1 | Other | C1CCOC1 | null | null | CCOC(=O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1>C1CCOC1>O=C(O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-be78ae5309b043708e89fcb9b33706e2 | NCCS(=O)(=O)c1ccccc1.O=C(O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1>>O=C(C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1)NCCS(=O)(=O)c1ccccc1 | C(C)(C)N(CC)C(C)C.FC=1C=C(COC2=C(C=C(NC3=NC=NC4=CC=C(C=C34)C3=CC=C(O3)C=CC(=O)O)C=C2)Cl)C=CC1.Cl.C1(=CC=CC=C1)S(=O)(=O)CCN.Cl.CN(CCCN=C=NCC)C>>FC=1C=C(COC2=C(C=C(NC3=NC=NC4=CC=C(C=C34)C3=CC=C(O3)C=CC(=O)NCCS(=O)(=O)C3=CC=CC=C3)C=C2)Cl)C=CC1 | [NH2:37][CH2:38][CH2:39][S:40](=[O:41])(=[O:42])[c:43]1[cH:44][cH:45][cH:46][cH:47][cH:48]1.O[C:2](=[O:1])[CH:3]=[CH:4][c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]3[n:13][cH:14][n:15][c:16]([NH:17][c:18]4[cH:19][cH:20][c:21]([O:22][CH2:23][c:24]5[cH:25][cH:26][cH:27][c:28]([F:29])[cH:30]5)[c:31]([Cl:32])[cH:33]4... | NCCS(=O)(=O)c1ccccc1.O=C(O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1 | O=C(C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1)NCCS(=O)(=O)c1ccccc1 | null | null | C(C)#N | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5ccccc5)cc4)c3c2)o1)NCCS(=O)(=O)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C:4]-[c:5]:[#8;a:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#8;a:6]:[c:5]-[C:4]=[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:9]-[C:8]-[C:7] | null | [] | null | null | null | null | Prepared according to Procedure (I) utilizing 3-(5-{4-[4-(3-fluorobenzyloxy)-3-chloroanilino]-6-quinazolinyl}-2-furyl)-2-propenoic acid (0.25 g, 0.45 mmol), 2-(phenylsulfonyl)-ethylamine hydrochloride (0.30 g, 1.36 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.26 g, 1.36 mmol) and diisopropyleth... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccoc1.c1ccc2ncncc2c1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C(C)#N | null | null | NCCS(=O)(=O)c1ccccc1.O=C(O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1>C(C)#N>O=C(C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1)NCCS(=O)(=O)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a519910c0c174131bbeedb903b67247e | CC(C)S(=O)(=O)CCN.O=C(O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1>>CC(C)S(=O)(=O)CCNC(=O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1 | FC=1C=C(COC2=C(C=C(NC3=NC=NC4=CC=C(C=C34)C3=CC=C(O3)C=CC(=O)O)C=C2)Cl)C=CC1.C(=O)(N1C=NC=C1)N1C=NC=C1.C(C)(C)S(=O)(=O)CCN>>FC=1C=C(COC2=C(C=C(NC3=NC=NC4=CC=C(C=C34)C3=CC=C(O3)C=CC(=O)NCCS(=O)(=O)C(C)C)C=C2)Cl)C=CC1 | [CH3:1][CH:2]([CH3:3])[S:4](=[O:5])(=[O:6])[CH2:7][CH2:8][NH2:9].O[C:10](=[O:11])[CH:12]=[CH:13][c:14]1[cH:15][cH:16][c:17](-[c:18]2[cH:19][cH:20][c:21]3[n:22][cH:23][n:24][c:25]([NH:26][c:27]4[cH:28][cH:29][c:30]([O:31][CH2:32][c:33]5[cH:34][cH:35][cH:36][c:37]([F:38])[cH:39]5)[c:40]([Cl:41])[cH:42]4)[c:43]3[cH:44]2)[... | CC(C)S(=O)(=O)CCN.O=C(O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1 | CC(C)S(=O)(=O)CCNC(=O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(COc2ccc(Nc3ncnc4ccc(-c5ccco5)cc34)cc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C:4]-[c:5]:[#8;a:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#8;a:6]:[c:5]-[C:4]=[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:9]-[C:8]-[C:7] | 33.9 | [{"value": 33.9, "product": "FC=1C=C(COC2=C(C=C(NC3=NC=NC4=CC=C(C=C34)C3=CC=C(O3)C=CC(=O)NCCS(=O)(=O)C(C)C)C=C2)Cl)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Prepared according to Procedure I utilizing 3-(5-{4-[4-(3-fluorobenzyloxy)-3-chloroanilino]-6-quinazolinyl}-2-furyl)-2-propenoic acid (0.22 g, 0.4 mmol), carbonyldiimidazole (0.58 g, 3.6 mmol), and iso-propanesulfonylethylamine (0.24 g, 1.6 mmol) in DMF to afford the title compound (0.088 g). Electrospray MS 649 m/z (M... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccoc1.c1ccc2ncncc2c1.c1ccccc1.c1ccccc1 | HO- | CN(C)C=O | null | null | CC(C)S(=O)(=O)CCN.O=C(O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1>CN(C)C=O>CC(C)S(=O)(=O)CCNC(=O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7a22b9c4cfd046fcb7207e23602d9aad | CCCS(=O)(=O)CCN.O=C(O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1>>CCCS(=O)(=O)CCNC(=O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1 | FC=1C=C(COC2=C(C=C(NC3=NC=NC4=CC=C(C=C34)C3=CC=C(O3)C=CC(=O)O)C=C2)Cl)C=CC1.C(=O)(N1C=NC=C1)N1C=NC=C1.C(CC)S(=O)(=O)CCN>>FC=1C=C(COC2=C(C=C(NC3=NC=NC4=CC=C(C=C34)C3=CC=C(O3)C=CC(=O)NCCS(=O)(=O)CCC)C=C2)Cl)C=CC1 | [CH3:1][CH2:2][CH2:3][S:4](=[O:5])(=[O:6])[CH2:7][CH2:8][NH2:9].O[C:10](=[O:11])[CH:12]=[CH:13][c:14]1[cH:15][cH:16][c:17](-[c:18]2[cH:19][cH:20][c:21]3[n:22][cH:23][n:24][c:25]([NH:26][c:27]4[cH:28][cH:29][c:30]([O:31][CH2:32][c:33]5[cH:34][cH:35][cH:36][c:37]([F:38])[cH:39]5)[c:40]([Cl:41])[cH:42]4)[c:43]3[cH:44]2)[o... | CCCS(=O)(=O)CCN.O=C(O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1 | CCCS(=O)(=O)CCNC(=O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(COc2ccc(Nc3ncnc4ccc(-c5ccco5)cc34)cc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C:4]-[c:5]:[#8;a:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#8;a:6]:[c:5]-[C:4]=[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:9]-[C:8]-[C:7] | 18.3 | [{"value": 18.3, "product": "FC=1C=C(COC2=C(C=C(NC3=NC=NC4=CC=C(C=C34)C3=CC=C(O3)C=CC(=O)NCCS(=O)(=O)CCC)C=C2)Cl)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Prepared according to Procedure I utilizing 3-(5-{4-[4-(3-fluorobenzyloxy)-3-chloroanilino]-6-quinazolinyl}-2-furyl)-2-propenoic acid (0.23 g, 0.42 mmol), carbonyldiimidazole (0.21 g, 1.27 mmol), and n-propanesulfonylethylamine (0.16 g, 0.85 mmol) in DMF to afford the title compound (0.05 g) after purification by chrom... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccoc1.c1ccc2ncncc2c1.c1ccccc1.c1ccccc1 | HO- | CN(C)C=O | null | null | CCCS(=O)(=O)CCN.O=C(O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1>CN(C)C=O>CCCS(=O)(=O)CCNC(=O)C=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f86ddba99d7d4cc8b6dea128f5932bdb | NCCS(=O)(=O)c1ccccc1.O=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1>>O=S(=O)(CCNCC1(c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)CC=CO1)c1ccccc1 | CCN(CC)CC.FC=1C=C(COC2=C(C=C(NC3=NC=NC4=CC=C(C=C34)C3=CC=C(O3)C=O)C=C2)Cl)C=CC1.[BH4-].[Na+].Cl.C1(=CC=CC=C1)S(=O)(=O)CCN>>FC=1C=C(COC2=C(C=C(C=C2)NC2=NC=NC3=CC=C(C=C23)C2(OC=CC2)CNCCS(=O)(=O)C2=CC=CC=C2)Cl)C=CC1 | [O:1]=[S:2](=[O:3])([CH2:4][CH2:5][NH2:6])[c:40]1[cH:41][cH:42][cH:43][cH:44][cH:45]1.O=[CH:7][c:38]1[cH:37][cH:36][c:8](-[c:9]2[cH:10][cH:11][c:12]3[n:13][cH:14][n:15][c:16]([NH:17][c:18]4[cH:19][cH:20][c:21]([O:22][CH2:23][c:24]5[cH:25][cH:26][cH:27][c:28]([F:29])[cH:30]5)[c:31]([Cl:32])[cH:33]4)[c:34]3[cH:35]2)[o:39... | NCCS(=O)(=O)c1ccccc1.O=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1 | O=S(=O)(CCNCC1(c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)CC=CO1)c1ccccc1 | null | null | C1CCOC1.CO | Heteroatom Alkylation and Arylation | OtherReaction | 60daaae2aa2691c6f6c8fce40bf2867cd406f615b992e21187e00dafdb28693d | 6e720f106632e7beb8e1e6ef4feb2887aa2ceca2bc069d68a26e7d0957c071b3 | O=S(=O)(CCNCC1(c2ccc3ncnc(Nc4ccc(OCc5ccccc5)cc4)c3c2)CC=CO1)c1ccccc1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[c;H0;D3;+0:6]2:[c:7]:[c:8]:[c:9](:[#7;a:10]):[c:11](:[c:12]:[#7;a:13]):[c:14]:2):[o;H0;D2;+0:15]:1.[C:16]-[C:17]-[NH2;D1;+0:18]>>[#7;a:10]:[c:9]1:[c:8]:[c:7]:[c;H0;D3;+0:6](-[C;H0;D4;+0:5]2(-[CH2;D2;+0:1]-[NH;D2;+0:18]-[C:17]-[C:16])-[CH2;D2;+0:4... | null | [] | null | null | null | null | The title compound and its hydrochloride salt are prepared according to Procedure D utilizing 5-{4-[4-(3-fluoro-benzyloxy)-3-chloroanilino]-6-quinazolinyl}-2-furaldehyde (0.317 mmol, 0.15 g), Phenylsulfonylethyl amine hydrochloride salt (0.475 mmol, 0.105 g) in the presence of Et3N (0.51 mmol, 0.067 mL) and NaBH4 (0.79... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Ether.Secondary amine | c1ccoc1 | C1=COCC1 | c1ccc2ncncc2c1.c1ccccc1.c1ccccc1.C1=COCC1.c1ccccc1 | Other | C1CCOC1.CO | null | null | NCCS(=O)(=O)c1ccccc1.O=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1>C1CCOC1.CO>O=S(=O)(CCNCC1(c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)CC=CO1)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d2de4a22ac4a4e4bae213dad040d5f2d | CCCS(=O)(=O)CCN.O=Cc1ccc(-c2cc3c(Nc4ccc(OCc5cccc(F)c5)cc4)ncnc3cn2)o1>>CCCS(=O)(=O)CCNCC1(c2cc3c(Nc4ccc(OCc5cccc(F)c5)cc4)ncnc3cn2)CC=CO1 | FC=1C=C(COC2=CC=C(C=C2)NC=2C3=C(N=CN2)C=NC(=C3)C3=CC=C(O3)C=O)C=CC1.C(CC)S(=O)(=O)CCN.C(OC)COC>>FC=1C=C(COC2=CC=C(C=C2)NC=2C3=C(N=CN2)C=NC(=C3)C3(OC=CC3)CNCCS(=O)(=O)CCC)C=CC1 | [CH3:1][CH2:2][CH2:3][S:4](=[O:5])(=[O:6])[CH2:7][CH2:8][NH2:9].O=[CH:10][c:40]1[cH:39][cH:38][c:11](-[c:12]2[cH:13][c:14]3[c:15]([NH:16][c:17]4[cH:18][cH:19][c:20]([O:21][CH2:22][c:23]5[cH:24][cH:25][cH:26][c:27]([F:28])[cH:29]5)[cH:30][cH:31]4)[n:32][cH:33][n:34][c:35]3[cH:36][n:37]2)[o:41]1>>[CH3:1][CH2:2][CH2:3][S:... | CCCS(=O)(=O)CCN.O=Cc1ccc(-c2cc3c(Nc4ccc(OCc5cccc(F)c5)cc4)ncnc3cn2)o1 | CCCS(=O)(=O)CCNCC1(c2cc3c(Nc4ccc(OCc5cccc(F)c5)cc4)ncnc3cn2)CC=CO1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 60daaae2aa2691c6f6c8fce40bf2867cd406f615b992e21187e00dafdb28693d | 6e720f106632e7beb8e1e6ef4feb2887aa2ceca2bc069d68a26e7d0957c071b3 | C1=COC(c2cc3c(Nc4ccc(OCc5ccccc5)cc4)ncnc3cn2)C1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[c;H0;D3;+0:6]2:[#7;a:7]:[c:8]:[c:9](:[#7;a:10]):[c:11](:[c:12]:2):[c:13]:[#7;a:14]):[o;H0;D2;+0:15]:1.[C:16]-[C:17]-[NH2;D1;+0:18]>>[#7;a:14]:[c:13]:[c:11]1:[c:12]:[c;H0;D3;+0:6](-[C;H0;D4;+0:5]2(-[CH2;D2;+0:1]-[NH;D2;+0:18]-[C:17]-[C:16])-[CH2;D... | null | [] | null | null | null | null | 5-(4-(4-(3-Fluorobenzyloxy)-phenylamino)-pyrido[3,4-d]pyrimidin-6-yl)-furan-2-carbaldehyde (0.31 mmol) and 2-n-propanesulphonyl-ethyl amine (0.94 mmol) were reacted together in dimethoxyethane as in Procedure D. 1H NMR (DMSO) 11.25 (bs, 1H); 9.88 (bs, 1H); 9.49 (s, 1H); 9.20 (s, 1H); 8.80 (s, 1H); 7.85 (d, 2H); 7.44 (m... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Ether.Secondary amine | c1ccoc1 | C1=COCC1 | c1ccccc1.c1ccccc1.c1cc2cncnc2cn1.C1=COCC1 | Other | null | null | null | CCCS(=O)(=O)CCN.O=Cc1ccc(-c2cc3c(Nc4ccc(OCc5cccc(F)c5)cc4)ncnc3cn2)o1>>CCCS(=O)(=O)CCNCC1(c2cc3c(Nc4ccc(OCc5cccc(F)c5)cc4)ncnc3cn2)CC=CO1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c4c3595226964ea0be608396e1dcb098 | CCCS(=O)(=O)CCN.O=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1>>CCCS(=O)(=O)CCNCC1(c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)CC=CO1 | ClC=1C=C(NC2=NC=NC3=CC=C(C=C23)C2=CC=C(O2)C=O)C=CC1OCC1=CC(=CC=C1)F.C(CC)S(=O)(=O)CCN.C(OC)COC>>FC=1C=C(COC2=C(C=C(C=C2)NC2=NC=NC3=CC=C(C=C23)C2(OC=CC2)CNCCS(=O)(=O)CCC)Cl)C=CC1 | [CH3:1][CH2:2][CH2:3][S:4](=[O:5])(=[O:6])[CH2:7][CH2:8][NH2:9].O=[CH:10][c:41]1[cH:40][cH:39][c:11](-[c:12]2[cH:13][cH:14][c:15]3[n:16][cH:17][n:18][c:19]([NH:20][c:21]4[cH:22][cH:23][c:24]([O:25][CH2:26][c:27]5[cH:28][cH:29][cH:30][c:31]([F:32])[cH:33]5)[c:34]([Cl:35])[cH:36]4)[c:37]3[cH:38]2)[o:42]1>>[CH3:1][CH2:2][... | CCCS(=O)(=O)CCN.O=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1 | CCCS(=O)(=O)CCNCC1(c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)CC=CO1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 60daaae2aa2691c6f6c8fce40bf2867cd406f615b992e21187e00dafdb28693d | 6e720f106632e7beb8e1e6ef4feb2887aa2ceca2bc069d68a26e7d0957c071b3 | C1=COC(c2ccc3ncnc(Nc4ccc(OCc5ccccc5)cc4)c3c2)C1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[c;H0;D3;+0:6]2:[c:7]:[c:8]:[c:9](:[#7;a:10]):[c:11](:[c:12]:[#7;a:13]):[c:14]:2):[o;H0;D2;+0:15]:1.[C:16]-[C:17]-[NH2;D1;+0:18]>>[#7;a:10]:[c:9]1:[c:8]:[c:7]:[c;H0;D3;+0:6](-[C;H0;D4;+0:5]2(-[CH2;D2;+0:1]-[NH;D2;+0:18]-[C:17]-[C:16])-[CH2;D2;+0:4... | null | [] | null | null | null | null | 5-(4-{3-Chloro-4-[(3-fluorobenzyl)oxy]anilino}-6-quinazolinyl)-2-furaldehyde (0.32 mmol) and 2-n-propanesulphonyl-ethyl amine (0.95 mmol) were reacted together in dimethoxyethane as in Procedure D. 1H NMR (DMSO) 11.85 (bs, 1H); 9.94 (bs, 2H); 9.67 (s, 1H); 8.95 (s, 1H); 8.45 (d, 1H); 8.08 (s, 1H); 8.00 (d, 1H); 7.84 (d... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Ether.Secondary amine | c1ccoc1 | C1=COCC1 | c1ccc2ncncc2c1.c1ccccc1.c1ccccc1.C1=COCC1 | Other | null | null | null | CCCS(=O)(=O)CCN.O=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1>>CCCS(=O)(=O)CCNCC1(c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)CC=CO1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c44c7acdd0cd4effb21be3d87b655684 | CC(C)S(=O)(=O)CCN.O=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1>>CC(C)C(CNCC1(c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)CC=CO1)=S(=O)=O | CCN(CC)CC.C1CCOC1.CO.FC=1C=C(COC2=C(C=C(NC3=NC=NC4=CC=C(C=C34)C3=CC=C(O3)C=O)C=C2)Cl)C=CC1.[BH4-].[Na+].Cl.C(C)(C)S(=O)(=O)CCN>>FC=1C=C(COC2=C(C=C(C=C2)NC2=NC=NC3=CC=C(C=C23)C2(OC=CC2)CNCC(C(C)C)=S(=O)=O)Cl)C=CC1 | [CH3:1][CH:2]([CH3:3])[S:40]([CH2:4][CH2:5][NH2:6])(=[O:41])=[O:42].O=[CH:7][c:38]1[cH:37][cH:36][c:8](-[c:9]2[cH:10][cH:11][c:12]3[n:13][cH:14][n:15][c:16]([NH:17][c:18]4[cH:19][cH:20][c:21]([O:22][CH2:23][c:24]5[cH:25][cH:26][cH:27][c:28]([F:29])[cH:30]5)[c:31]([Cl:32])[cH:33]4)[c:34]3[cH:35]2)[o:39]1>>[CH3:1][CH:2](... | CC(C)S(=O)(=O)CCN.O=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1 | CC(C)C(CNCC1(c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)CC=CO1)=S(=O)=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1b0080e890ae8315d1f84c0b390aa75b246afaa192e612173d63a6c36d407d62 | 3a41577e0815d59ec9dddd142d8f2f1930fdd79f0bb05d3ed5a99ff7d1cf5106 | C1=COC(c2ccc3ncnc(Nc4ccc(OCc5ccccc5)cc4)c3c2)C1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[c;H0;D3;+0:6]2:[c:7]:[c:8]:[c:9](:[#7;a:10]):[c:11](:[c:12]:[#7;a:13]):[c:14]:2):[o;H0;D2;+0:15]:1.[C;D1;H3:16]-[CH;D3;+0:17](-[C;D1;H3:18])-[S;H0;D4;+0:19](=[O;D1;H0:20])(=[O;D1;H0:21])-[CH2;D2;+0:22]-[C:23]-[NH2;D1;+0:24]>>[#7;a:10]:[c:9]1:[c:8... | null | [] | null | null | null | null | The title compound and its hydrochloride salt are prepared according to Procedure D utilizing 5-{4-[4-(3-fluoro-benzyloxy)-3-chloroanilino]-6-quinazolinyl}-2-furaldehyde (0.317 mmol, 0.15 g), Isopropylsulfonylethyl amine hydrochloride salt (0.475 mmol, 0.105 g) in the presence of Et3N (0.95 mmol, 0.13 mL) and NaBH4 (1.... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine.Sulfone | Ether.Secondary amine | c1ccoc1 | C1=COCC1 | c1ccc2ncncc2c1.c1ccccc1.c1ccccc1.C1=COCC1 | Other | null | null | null | CC(C)S(=O)(=O)CCN.O=Cc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1>>CC(C)C(CNCC1(c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)CC=CO1)=S(=O)=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a81d5d1349864fc88ae6b2d17e603ab1 | C[C@@H](CO)NC(=O)OC(C)(C)C>>C[C@@H](C=O)NC(=O)OC(C)(C)C | C(C)(C)(C)OC(=O)N[C@H](CO)C.CC(=O)OI1(C=2C=CC=CC2C(=O)O1)(OC(=O)C)OC(=O)C.S([O-])(O)=O.[Na+]>>C(C)(C)(C)OC(=O)N[C@H](C=O)C | [CH3:1][C@@H:2]([CH2:3][OH:4])[NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12]>>[CH3:1][C@@H:2]([CH:3]=[O:4])[NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12] | C[C@@H](CO)NC(=O)OC(C)(C)C | C[C@@H](C=O)NC(=O)OC(C)(C)C | null | null | C(Cl)Cl.C(C)(=O)OCC | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | null | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:7])-[#7:8]-[C:9](-[C;D1;H3:10])-[CH2;D2;+0:11]-[OH;D1;+0:12]>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:7])-[#7:8]-[C:9](-[C;D1;H3:10])-[CH;D2;+0:11]=[O;H0;D1;+0:12] | 92 | [{"value": 92.0, "product": "C(C)(C)(C)OC(=O)N[C@H](C=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.0, "product": "C(C)(C)(C)OC(=O)N[C@H](C=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | (S)-(−)-2-(tert-Butoxycarbonylamino)-1-propanol (523 mg, 2.98 mmol, 1.0 equiv.) was dissolved in 45 mL methylene chloride in a 100 mL r.b. flask with a magnetic stir bar. To this clear homogeneous solution, Dess-Martin periodinane (1.523 g, 3.591 mmol, 1.2 equiv.) was added in one part and the cloudy white reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | null | null | C(Cl)Cl.C(C)(=O)OCC | null | 2 | C[C@@H](CO)NC(=O)OC(C)(C)C>C(Cl)Cl.C(C)(=O)OCC>C[C@@H](C=O)NC(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3527198d2b9c4ec69c83faf342732e9a | C[C@@H](CO)NC(=O)Cc1ccccc1>>C[C@@H](C=O)NC(=O)Cc1ccccc1 | C(C1=CC=CC=C1)C(=O)N[C@H](CO)C.CC(=O)OI1(C=2C=CC=CC2C(=O)O1)(OC(=O)C)OC(=O)C>>C(C1=CC=CC=C1)C(=O)N[C@H](C=O)C | [CH3:1][C@@H:2]([CH2:3][OH:4])[NH:5][C:6](=[O:7])[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[CH3:1][C@@H:2]([CH:3]=[O:4])[NH:5][C:6](=[O:7])[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1 | C[C@@H](CO)NC(=O)Cc1ccccc1 | C[C@@H](C=O)NC(=O)Cc1ccccc1 | null | null | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccccc1 | [C;D1;H3:1]-[C:2](-[#7:3]-[C:4]=[O;D1;H0:5])-[CH2;D2;+0:6]-[OH;D1;+0:7]>>[C;D1;H3:1]-[C:2](-[#7:3]-[C:4]=[O;D1;H0:5])-[CH;D2;+0:6]=[O;H0;D1;+0:7] | null | [] | null | null | 2 | HOUR | (S)-2-(benzylcarbonylamino)-propanol (5.00 g, 23.9 mmol) was dissolved in CH2Cl2 (200 mL) and treated with Dess-Martin periodinane (12.26 g, 1.1 eq). The mixture was stirred for 2 hours, then quenched with sodium thiosulphate, and the solvent removed in vacuo. The residue was then separated between sodium hydroxide (1M... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1 | null | C(Cl)Cl | null | 2 | C[C@@H](CO)NC(=O)Cc1ccccc1>C(Cl)Cl>C[C@@H](C=O)NC(=O)Cc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-625de8f5f3b74db1a46bdb35a7ac383c | C[C@@H](CNc1ccc(OC(F)(F)F)cc1)NC(=O)OCc1ccccc1>>C[C@H](N)CNc1ccc(OC(F)(F)F)cc1 | C(C1=CC=CC=C1)OC(N[C@H](CNC1=CC=C(C=C1)OC(F)(F)F)C)=O>>FC(OC1=CC=C(C=C1)NC[C@H](C)N)(F)F | O=C(OCc1ccccc1)[NH:3][C@@H:2]([CH3:1])[CH2:4][NH:5][c:6]1[cH:7][cH:8][c:9]([O:10][C:11]([F:12])([F:13])[F:14])[cH:15][cH:16]1>>[CH3:1][C@H:2]([NH2:3])[CH2:4][NH:5][c:6]1[cH:7][cH:8][c:9]([O:10][C:11]([F:12])([F:13])[F:14])[cH:15][cH:16]1 | C[C@@H](CNc1ccc(OC(F)(F)F)cc1)NC(=O)OCc1ccccc1 | C[C@H](N)CNc1ccc(OC(F)(F)F)cc1 | null | [Pd] | C(C)O | Reduction | Hydrogenolysis of amides/imides/carbamates | 087b6600ba91d3df931fe6979f2445c192cbfd59e04fd2d8a10f7c7573ac669f | 4e549866ec1acadec4c84aaf8495992a28ec78d8ea5ef1b9f44dd843b0dcb7d4 | c1ccccc1 | O=C(-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:1]-[C:2](-[C:3])-[C;D1;H3:4]>>[C:3]-[C:2](-[C;D1;H3:4])-[NH2;D1;+0:1] | 72 | [{"value": 72.0, "product": "FC(OC1=CC=C(C=C1)NC[C@H](C)N)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | [1-(S)-Methyl-2-(4-trifluoromethoxy-phenylamino)-ethyl]-carbamic acid benzyl ester (23.9 mmol) was dissolved in ethanol (200 mL) then placed under nitrogen. 10% Palladium on carbon was added (0.5 g) and the mixture was stirred under hydrogen (atmospheric pressure) overnight. When reaction was complete, the mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | c1ccccc1 | null | c1ccccc1 | HO- | [Pd].C(C)O | null | 8 | C[C@@H](CNc1ccc(OC(F)(F)F)cc1)NC(=O)OCc1ccccc1>[Pd].C(C)O>C[C@H](N)CNc1ccc(OC(F)(F)F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6db6066224dd4b30a298946d60301615 | C=C(C)CBr.CC(C)(C)OC(=O)Nc1ccc(F)cc1>>C=C(C)Cc1cc(F)ccc1NC(=O)OC(C)(C)C | [Li]C(C)(C)C.CCCCC.C(=O)(OC(C)(C)C)NC1=CC=C(C=C1)F.C(C(C)=C)Br>>C(C)(C)(C)OC(NC1=C(C=C(C=C1)F)CC(=C)C)=O | Br[CH2:4][C:2](=[CH2:1])[CH3:3].[cH:5]1[cH:6][c:7]([F:8])[cH:9][cH:10][c:11]1[NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19]>>[CH2:1]=[C:2]([CH3:3])[CH2:4][c:5]1[cH:6][c:7]([F:8])[cH:9][cH:10][c:11]1[NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19] | C=C(C)CBr.CC(C)(C)OC(=O)Nc1ccc(F)cc1 | C=C(C)Cc1cc(F)ccc1NC(=O)OC(C)(C)C | null | null | C1CCOC1 | C-C Coupling | Friedel-Crafts alkylation with halide | abd82b32c15853d5913cc8f5d51923ff8cee2c9e5cfc2628ece51b84576c3f2d | f5e5e22797736d188bba28deb76a4cee8e4fee4dca04fe24f733d2ee68a23361 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[C;D1;H2:3])-[C;D1;H3:4].[C;D1;H3:5]-[C:6](-[C;D1;H3:7])(-[C;D1;H3:8])-[#8:9]-[C:10](=[O;D1;H0:11])-[#7:12]-[c:13](:[c:14]):[cH;D2;+0:15]:[c:16]:[c:17]>>[C;D1;H2:3]=[C:2](-[C;D1;H3:4])-[CH2;D2;+0:1]-[c;H0;D3;+0:15](:[c:16]:[c:17]):[c:13](-[#7:12]-[C:10](=[O;D1;H0:11])-[#8:9]-[C:6](-[C;D1;H3:5])(... | 80 | [{"value": 80.0, "product": "C(C)(C)(C)OC(NC1=C(C=C(C=C1)F)CC(=C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | -20 | CELSIUS | 2.5 | HOUR | A solution of N-Boc-4-fluoroaniline (9.02 g, 42.7 mmol) in THF (112 mL) was cooled to −60° C. using a cryocool instrument. The solution was treated with 1.7 M t-BuLi in pentane (63 mL, 106.7 mmol) dropwise. After the first equivalent of base was consumed, a yellow solution formed. The reaction was allowed to warm to −2... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | C1CCOC1 | -20 | 2.5 | C=C(C)CBr.CC(C)(C)OC(=O)Nc1ccc(F)cc1>C1CCOC1>C=C(C)Cc1cc(F)ccc1NC(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5d12771205ad4d3681c0bd0e92b66097 | C=C(C)Cc1cc(F)ccc1NC(=O)OC(C)(C)C>>CC1(C)Cc2cc(F)ccc2N1 | CS(=O)(=O)O.C(C)(C)(C)OC(NC1=C(C=C(C=C1)F)CC(=C)C)=O.C1(=CC=CC=C1)OC.FC(C(=O)O)(F)F>>CC1(NC2=CC=C(C=C2C1)F)C | CC(C)(C)OC(=O)[NH:12][c:11]1[c:5]([CH2:4][C:2](=[CH2:1])[CH3:3])[cH:6][c:7]([F:8])[cH:9][cH:10]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][c:5]2[cH:6][c:7]([F:8])[cH:9][cH:10][c:11]2[NH:12]1 | C=C(C)Cc1cc(F)ccc1NC(=O)OC(C)(C)C | CC1(C)Cc2cc(F)ccc2N1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | OtherReaction | b9db8b959ce76a9ce9ae402df8bd3b8657a4d8353a0f20fd79710a2c4e90449b | f4be2a1dc40806f7d87a3d054308bec820304200bc50fd9c846232e4d6353bb4 | c1ccc2c(c1)CCN2 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5]-[C;H0;D3;+0:6](-[C;D1;H3:7])=[CH2;D1;+0:8]>>[C;D1;H3:7]-[C;H0;D4;+0:6]1(-[CH3;D1;+0:8])-[C:5]-[c:4]:[c:2](:[c:3])-[NH;D2;+0:1]-1 | 66 | [{"value": 66.0, "product": "CC1(NC2=CC=C(C=C2C1)F)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.8, "product": "CC1(NC2=CC=C(C=C2C1)F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 170 | CELSIUS | 4 | HOUR | A sample of [4-Fluoro-2-(2-methyl-allyl)-phenyl]-carbamic acid tert-butyl ester (1.10 g, 4.14 mmol) was treated with anisole (5 mL), dichloromethane (5 mL) and trifluoroacetic acid (5 mL) and stirred for 4 hours. The solvent was removed and the reaction was transferred to a microwave reaction vial using methanesulfonic... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Vinyl.Boc | Secondary amine | null | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | HO- | ClCCl | 170 | 4 | C=C(C)Cc1cc(F)ccc1NC(=O)OC(C)(C)C>ClCCl>CC1(C)Cc2cc(F)ccc2N1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b414bba41a3e46d7aa89af8ac87e3429 | C=C(C)CN(C(C)=O)c1ccc(F)cc1>>CC(=O)N1CC(C)(C)c2cc(F)ccc21 | FC1=CC=C(C=C1)N(C(C)=O)CC(=C)C.[Cl-].[Cl-].[Cl-].[Al+3].O>>FC=1C=C2C(CN(C2=CC1)C(C)=O)(C)C | [CH3:1][C:2](=[O:3])[N:4]([CH2:5][C:6]([CH3:7])=[CH2:8])[c:15]1[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]1>>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][C:6]([CH3:7])([CH3:8])[c:9]2[cH:10][c:11]([F:12])[cH:13][cH:14][c:15]21 | C=C(C)CN(C(C)=O)c1ccc(F)cc1 | CC(=O)N1CC(C)(C)c2cc(F)ccc21 | null | null | C(C)(=O)OCC | C-C Coupling | OtherReaction | 4d710ad3c860e47fcf3f7015a55b39b05e571ad23da36e5437a9a2523003c972 | 48297e5b607b4624d5b08506879ba8f9dd47fb272c10888542fa01ef83829ef2 | c1ccc2c(c1)CCN2 | [C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C:5]-[C;H0;D3;+0:6](-[C;D1;H3:7])=[CH2;D1;+0:8])-[c:9](:[c:10]):[cH;D2;+0:11]:[c:12]:[c:13]>>[C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C;H0;D4;+0:6](-[C;D1;H3:7])(-[CH3;D1;+0:8])-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:9]-1:[c:10] | null | [] | 150 | CELSIUS | null | null | According to the procedure described in S. Coulton et al. WO9925709 with the following modifications. N-(4-Fluoro-phenyl)-N-(2-methyl-allyl)-acetamide (5 grams, 24.12 mmol) was added to a microwave tube with aluminum trichloride (7 grams, 52.4 mmol). The tube was capped and heated to 150° C. for 20 minutes under microw... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | null | c1ccccc1 | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | null | C(C)(=O)OCC | 150 | null | C=C(C)CN(C(C)=O)c1ccc(F)cc1>C(C)(=O)OCC>CC(=O)N1CC(C)(C)c2cc(F)ccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-52df45dfb25f45e49ea2788e57bdea4b | CC(=O)N1CC(C)(C)c2cc(F)ccc21>>CC1(C)CNc2ccc(F)cc21 | FC=1C=C2C(CN(C2=CC1)C(C)=O)(C)C>>CC1(CNC2=CC=C(C=C12)F)C | CC(=O)[N:5]1[CH2:4][C:2]([CH3:1])([CH3:3])[c:12]2[c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11]2>>[CH3:1][C:2]1([CH3:3])[CH2:4][NH:5][c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][c:12]21 | CC(=O)N1CC(C)(C)c2cc(F)ccc21 | CC1(C)CNc2ccc(F)cc21 | null | null | Cl | Reduction | Hydrogenolysis of tertiary amines | 3325d321b6e740eb07332b61ecb10184cad4db5efbb86509e39d17e13b7f3d02 | 62cf08a8ae6315067a063b5b3495125ccbdaff6b2340ce1d3e1c7b6cde962ae4 | c1ccc2c(c1)CCN2 | C-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[c:4]:[c:5]-1:[c:6]>>[c:6]:[c:5]1:[c:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1 | null | [] | 200 | CELSIUS | null | null | According to the procedure described in S. Coulton et al. WO9925709 with the following modifications. N-(4-Fluoro-phenyl)-N-(2-methyl-allyl)-acetamide (5 grams, 24.12 mmol) was added to a microwave tube with aluminum trichloride (7 grams, 52.4 mmol). The tube was capped and heated to 150° C. for 20 minutes under microw... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Secondary amine | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | HO- | Cl | 200 | null | CC(=O)N1CC(C)(C)c2cc(F)ccc21>Cl>CC1(C)CNc2ccc(F)cc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f24672f96fd449ec889e1ebcdbfb4b43 | O=C(N[C@H](C(=O)O)C1CC1)OCc1ccccc1>>O=C(N[C@H](CO)C1CC1)OCc1ccccc1 | C(C1=CC=CC=C1)OC(=O)N[C@H](C(=O)O)C1CC1.Cl>>C(C1=CC=CC=C1)OC(N[C@H](CO)C1CC1)=O | O=[C:5]([C@@H:4]([NH:3][C:2](=[O:1])[O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[CH:7]1[CH2:8][CH2:9]1)[OH:6]>>[O:1]=[C:2]([NH:3][C@H:4]([CH2:5][OH:6])[CH:7]1[CH2:8][CH2:9]1)[O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | O=C(N[C@H](C(=O)O)C1CC1)OCc1ccccc1 | O=C(N[C@H](CO)C1CC1)OCc1ccccc1 | null | null | C1CCOC1 | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | O=C(NCC1CC1)OCc1ccccc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7]>>[C:4]-[C:3](-[#7:5]-[C:6]=[O;D1;H0:7])-[CH2;D2;+0:1]-[O;D1;H1:2] | 50 | [{"value": 50.0, "product": "C(C1=CC=CC=C1)OC(N[C@H](CO)C1CC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.8, "product": "C(C1=CC=CC=C1)OC(N[C@H](CO)C1CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A solution of (S)-benzyloxycarbonylamino-cyclopropyl-acetic acid (3.2 g, 12.8 mmol) in THF (20 mL) was cooled in an ice/water bath and treated with a 1 M solution of BH3 in THF (16.7 mL, 16.7 mmol). The reaction was stirred for 4 hours and then treated with 1 M HCl until the bubbling ceased. The reaction was stirred ov... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | C1CC1.c1ccccc1 | Other | C1CCOC1 | null | 4 | O=C(N[C@H](C(=O)O)C1CC1)OCc1ccccc1>C1CCOC1>O=C(N[C@H](CO)C1CC1)OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ada4f3de1a684981bf4c3f420fe45e91 | COc1ccc(CCl)cc1.O=C1Nc2ccc(F)cc2C1=O>>COc1ccc(CN2C(=O)C(=O)c3cc(F)ccc32)cc1 | FC=1C=C2C(C(NC2=CC1)=O)=O.[H-].[Na+].COC1=CC=C(CCl)C=C1>>FC=1C=C2C(C(N(C2=CC1)CC1=CC=C(C=C1)OC)=O)=O | Cl[CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:21][cH:20]1.[NH:8]1[C:9](=[O:10])[C:11](=[O:12])[c:13]2[cH:14][c:15]([F:16])[cH:17][cH:18][c:19]21>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]2[C:9](=[O:10])[C:11](=[O:12])[c:13]3[cH:14][c:15]([F:16])[cH:17][cH:18][c:19]32)[cH:20][cH:21]1 | COc1ccc(CCl)cc1.O=C1Nc2ccc(F)cc2C1=O | COc1ccc(CN2C(=O)C(=O)c3cc(F)ccc32)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | c168ddb7803c893ec5334f16b8c2262b487eff0908e05ac9b9feab6bfceb9bd3 | 4a6c1e88c9e8bed487b746792f88d478ff36cc235f9a217d4632e6babdebdc9a | O=C1C(=O)N(Cc2ccccc2)c2ccccc21 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]-[C:11]-1=[O;D1;H0:12]>>[O;D1;H0:5]=[C:6]1-[C:11](=[O;D1;H0:12])-[c:10]:[c:8](:[c:9])-[N;H0;D3;+0:7]-1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 82.4 | [{"value": 82.0, "product": "FC=1C=C2C(C(N(C2=CC1)CC1=CC=C(C=C1)OC)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.4, "product": "FC=1C=C2C(C(N(C2=CC1)CC1=CC=C(C=C1)OC)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A solution of 5-fluoroisatin (5 g, 30.2 mmol) in DMF (60 mL) was cooled in an ice/water bath and treated with sodium hydride (1.44 g, 60.6 mmol) portionwise. The reaction was stirred for 15 minutes after the addition of the last portion and then treated with p-methoxybenzyl chloride (5.32 g, 45.3 mmol) and allowed to s... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amide | Tertiary amide | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CC[NH]2 | c1ccccc1.c1ccc2c(c1)CC[NH]2 | HCl | CN(C)C=O | null | 0.25 | COc1ccc(CCl)cc1.O=C1Nc2ccc(F)cc2C1=O>CN(C)C=O>COc1ccc(CN2C(=O)C(=O)c3cc(F)ccc32)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-16b226f5d2f74826891bc220841267bf | COc1ccc(CN2C(=O)C(=O)c3cc(F)ccc32)cc1>>COc1ccc(CN2C(=O)Cc3cc(F)ccc32)cc1 | FC=1C=C2C(C(N(C2=CC1)CC1=CC=C(C=C1)OC)=O)=O>>FC=1C=C2CC(N(C2=CC1)CC1=CC=C(C=C1)OC)=O | O=[C:11]1[C:9](=[O:10])[N:8]([CH2:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:20][cH:19]2)[c:18]2[c:12]1[cH:13][c:14]([F:15])[cH:16][cH:17]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]2[C:9](=[O:10])[CH2:11][c:12]3[cH:13][c:14]([F:15])[cH:16][cH:17][c:18]32)[cH:19][cH:20]1 | COc1ccc(CN2C(=O)C(=O)c3cc(F)ccc32)cc1 | COc1ccc(CN2C(=O)Cc3cc(F)ccc32)cc1 | null | null | O.O.NN.C(C)O | Reduction | OtherReaction | 38c2e25950c28dc6604fd64d3fb787fe72ad80b64a904fe4f0e941595091c2ef | f9ba67182f94acd5fbe41487f8f71e26bccf898b8fc8091ef46f4363de5628d4 | O=C1Cc2ccccc2N1Cc1ccccc1 | O=[C;H0;D3;+0:1]1-[C:2](=[O;D1;H0:3])-[#7:4](-[C:5])-[c:6]:[c:7]-1:[c:8]>>[C:5]-[#7:4]1-[c:6]:[c:7](:[c:8])-[CH2;D2;+0:1]-[C:2]-1=[O;D1;H0:3] | 90.3 | [{"value": 90.0, "product": "FC=1C=C2CC(N(C2=CC1)CC1=CC=C(C=C1)OC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.3, "product": "FC=1C=C2CC(N(C2=CC1)CC1=CC=C(C=C1)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 5-fluoro-1-(4-methoxy-benzyl)-1H-indole-2,3-dione (7.1 g, 24.9 mmol) in hydrazine hydrate (35 mL) and ethanol (15 mL) was refluxed overnight, diluted with water and extracted twice with ethyl acetate. The combined organics were dried over Na2SO4, filtered and concentrated. The residue was purified by sili... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | c1ccccc1.c1ccc2c(c1)CC[NH]2 | Other | O.O.NN.C(C)O | null | null | COc1ccc(CN2C(=O)C(=O)c3cc(F)ccc32)cc1>O.O.NN.C(C)O>COc1ccc(CN2C(=O)Cc3cc(F)ccc32)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1a9ad5e0afb94ae0b0ae03bd50bb41ff | COc1ccc(CCl)cc1.O=C1Nc2ccc(F)cc2C1=O>>COc1ccc(CN2C(=O)C(=O)c3cc(F)ccc32)cc1 | O.FC=1C=C2C(C(NC2=CC1)=O)=O.[H-].[Na+].COC1=CC=C(CCl)C=C1>>FC=1C=C2C(C(N(C2=CC1)CC1=CC=C(C=C1)OC)=O)=O | Cl[CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:21][cH:20]1.[NH:8]1[C:9](=[O:10])[C:11](=[O:12])[c:13]2[cH:14][c:15]([F:16])[cH:17][cH:18][c:19]21>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]2[C:9](=[O:10])[C:11](=[O:12])[c:13]3[cH:14][c:15]([F:16])[cH:17][cH:18][c:19]32)[cH:20][cH:21]1 | COc1ccc(CCl)cc1.O=C1Nc2ccc(F)cc2C1=O | COc1ccc(CN2C(=O)C(=O)c3cc(F)ccc32)cc1 | null | null | C(C)(=O)OCC.CCCCCC.CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | c168ddb7803c893ec5334f16b8c2262b487eff0908e05ac9b9feab6bfceb9bd3 | 4a6c1e88c9e8bed487b746792f88d478ff36cc235f9a217d4632e6babdebdc9a | O=C1C(=O)N(Cc2ccccc2)c2ccccc21 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]-[C:11]-1=[O;D1;H0:12]>>[O;D1;H0:5]=[C:6]1-[C:11](=[O;D1;H0:12])-[c:10]:[c:8](:[c:9])-[N;H0;D3;+0:7]-1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 80 | [{"value": 80.0, "product": "FC=1C=C2C(C(N(C2=CC1)CC1=CC=C(C=C1)OC)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | 5-Fluoro-1H-indole-2,3-dione (956 mg, 5.79 mmol, 1 eq) was added as a solution in dry DMF to a stirred slurry of sodium hydride (278 mg, 11.6 mmol, 2 eq) in dry DMF drop wise over 15 minutes under an inert atmosphere with adequate pressure release to accommodate H2 evolution. The resulting mixture was stirred for 1 hou... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amide | Tertiary amide | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CC[NH]2 | c1ccccc1.c1ccc2c(c1)CC[NH]2 | HCl | C(C)(=O)OCC.CCCCCC.CN(C)C=O | null | 0.25 | COc1ccc(CCl)cc1.O=C1Nc2ccc(F)cc2C1=O>C(C)(=O)OCC.CCCCCC.CN(C)C=O>COc1ccc(CN2C(=O)C(=O)c3cc(F)ccc32)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7aac8cfa82d54f13af14847300096782 | CC(C)(C)CC(O)Cn1cnc2cc(Cl)c(Cl)cc21.O=C(Cl)Oc1ccc([N+](=O)[O-])cc1>>CC(C)(C)CC(Cn1cnc2cc(Cl)c(Cl)cc21)OC(=O)Oc1ccc([N+](=O)[O-])cc1 | ClC1=CC2=C(N(C=N2)CC(CC(C)(C)C)O)C=C1Cl.C(Cl)Cl.ClC(=O)OC1=CC=C(C=C1)[N+](=O)[O-]>>C(OC(CC(C)(C)C)CN1C=NC2=C1C=C(C(=C2)Cl)Cl)(OC2=CC=C(C=C2)[N+](=O)[O-])=O | [CH3:1][C:2]([CH3:3])([CH3:4])[CH2:5][CH:6]([CH2:7][n:8]1[cH:9][n:10][c:11]2[cH:12][c:13]([Cl:14])[c:15]([Cl:16])[cH:17][c:18]12)[OH:19].Cl[C:20](=[O:21])[O:22][c:23]1[cH:24][cH:25][c:26]([N+:27](=[O:28])[O-:29])[cH:30][cH:31]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[CH2:5][CH:6]([CH2:7][n:8]1[cH:9][n:10][c:11]2[cH:12][c:13]([... | CC(C)(C)CC(O)Cn1cnc2cc(Cl)c(Cl)cc21.O=C(Cl)Oc1ccc([N+](=O)[O-])cc1 | CC(C)(C)CC(Cn1cnc2cc(Cl)c(Cl)cc21)OC(=O)Oc1ccc([N+](=O)[O-])cc1 | null | null | N1=CC=CC=C1.C(C)(=O)OCC | Acylation | Schotten-Baumann to ester | 9d3813d6d0fea128d006be246c91a81540a6fda22070dabe99cbd137dd931f94 | bf61d3d2f28b6503a73eb3548c26cb203a24f8622ebddd1c0211172cf3f6ae1d | O=C(OCCn1cnc2ccccc21)Oc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[c:4].[C:5]-[C:6](-[C:7])-[OH;D1;+0:8]>>[C:5]-[C:6](-[C:7])-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[c:4] | 77 | [{"value": 77.0, "product": "C(OC(CC(C)(C)C)CN1C=NC2=C1C=C(C(=C2)Cl)Cl)(OC2=CC=C(C=C2)[N+](=O)[O-])=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.9, "product": "C(OC(CC(C)(C)C)CN1C=NC2=C1C=C(C(=C2)Cl)Cl)(OC2=CC=C(C=C2)[N+](=O)[O-])=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | The product from step B (445 mg, 1.48 mmol) was dissolved in pyridine (4 mL) and CH2Cl2 (2 mL) and treated with 4-nitrophenyl chloroformate (328 mg, 1.62 mmol). The reaction vessel was sealed and heated to 80° C. overnight. After cooling to room temperature, the reaction was diluted with ethyl acetate and extracted wit... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Secondary alcohol | Ether.Ether | null | null | c1ccc2[nH]cnc2c1.c1ccccc1 | HCl | N1=CC=CC=C1.C(C)(=O)OCC | 80 | null | CC(C)(C)CC(O)Cn1cnc2cc(Cl)c(Cl)cc21.O=C(Cl)Oc1ccc([N+](=O)[O-])cc1>N1=CC=CC=C1.C(C)(=O)OCC>CC(C)(C)CC(Cn1cnc2cc(Cl)c(Cl)cc21)OC(=O)Oc1ccc([N+](=O)[O-])cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ebeacb0cf65a45659224bc4cab342c5c | CC(C)(C)C1CO1.Clc1cc2nc[nH]c2cc1Cl>>CC(C)(C)C(O)Cn1cnc2cc(Cl)c(Cl)cc21 | CN(C)C=O.ClC1=CC2=C(N=CN2)C=C1Cl.O1CC1C(C)(C)C.C([O-])([O-])=O.[K+].[K+]>>ClC1=CC2=C(N(C=N2)CC(C(C)(C)C)O)C=C1Cl | [CH3:1][C:2]([CH3:3])([CH3:4])[CH:5]1[O:6][CH2:7]1.[nH:8]1[cH:9][n:10][c:11]2[cH:12][c:13]([Cl:14])[c:15]([Cl:16])[cH:17][c:18]12>>[CH3:1][C:2]([CH3:3])([CH3:4])[CH:5]([OH:6])[CH2:7][n:8]1[cH:9][n:10][c:11]2[cH:12][c:13]([Cl:14])[c:15]([Cl:16])[cH:17][c:18]12 | CC(C)(C)C1CO1.Clc1cc2nc[nH]c2cc1Cl | CC(C)(C)C(O)Cn1cnc2cc(Cl)c(Cl)cc21 | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 21b711326352052a709eaf96d10effe5ac81d8e9213db97ad1bad2d8b61d52d9 | 48e6c0d0d0e8dae811945f6111d99833e797cf39e9d4bb64983a9fb362d30b9f | c1ccc2[nH]cnc2c1 | [C:1]-[C:2]1-[CH2;D2;+0:3]-[O;H0;D2;+0:4]-1.[c:5]:[c:6]1:[#7;a:7]:[c:8]:[nH;D2;+0:9]:[c:10]:1:[c:11]>>[C:1]-[C:2](-[OH;D1;+0:4])-[CH2;D2;+0:3]-[n;H0;D3;+0:9]1:[c:8]:[#7;a:7]:[c:6](:[c:5]):[c:10]:1:[c:11] | 73.3 | [{"value": 73.0, "product": "ClC1=CC2=C(N(C=N2)CC(C(C)(C)C)O)C=C1Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.3, "product": "ClC1=CC2=C(N(C=N2)CC(C(C)(C)C)O)C=C1Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 160 | CELSIUS | null | null | A large (2-5 mL) microwave reactor flask was charged with 5,6-dichlorobenzimidazole (571 mg, 3.1 mmol), 1,2-epoxy-3,3-dimethylbutane (307 mg, 3.1 mmol), powdered anhydrous potassium carbonate (424 mg, 3.1 mmol) and DMF (1.5 mL). The reaction was then heated in a microwave reactor for 6 minutes at 160° C. The reaction w... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Secondary alcohol | C1CO1.c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | null | C(C)(=O)OCC | 160 | null | CC(C)(C)C1CO1.Clc1cc2nc[nH]c2cc1Cl>C(C)(=O)OCC>CC(C)(C)C(O)Cn1cnc2cc(Cl)c(Cl)cc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fb86566308fe4d67b8cb99760354a6ee | C1COCCN1.Cc1ccc(S(=O)(=O)OC[C@@H](O)CC(C)(C)C)cc1>>CC(C)(C)C[C@H](O)CN1CCOCC1 | O[C@H](COS(=O)(=O)C1=CC=C(C=C1)C)CC(C)(C)C.N1CCOCC1>>CC(C[C@@H](CN1CCOCC1)O)(C)C | [NH:9]1[CH2:10][CH2:11][O:12][CH2:13][CH2:14]1.Cc1ccc(S(=O)(=O)O[CH2:8][C@H:6]([CH2:5][C:2]([CH3:1])([CH3:3])[CH3:4])[OH:7])cc1>>[CH3:1][C:2]([CH3:3])([CH3:4])[CH2:5][C@H:6]([OH:7])[CH2:8][N:9]1[CH2:10][CH2:11][O:12][CH2:13][CH2:14]1 | C1COCCN1.Cc1ccc(S(=O)(=O)OC[C@@H](O)CC(C)(C)C)cc1 | CC(C)(C)C[C@H](O)CN1CCOCC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4f71723cb4cd5480082ee5f88098fa59a5ff4edb81be4e74f8f8beb04e55c40f | 71b4ac4449ece5e0df64e56caf0f1cbac76e83f802a92104cfb6c6c861b6a71c | C1COCCN1 | C-c1:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2](-[C:3])-[O;D1;H1:4]):c:c:1.[#8:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[C:3]-[C:2](-[O;D1;H1:4])-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#8:5]-[C:10]-[C:9]-1 | 67 | [{"value": 67.0, "product": "CC(C[C@@H](CN1CCOCC1)O)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | 160 | CELSIUS | null | null | (S)-toluene-4-sulfonic acid 2-hydroxy-4,4-dimethyl-pentyl ester obtained from Example 4, step A (700 mg, 2.4 mmol) was charged to a large microwave reactor vial and treated with morpholine (3 mL). The vial was crimped shut and heated to 160° C. for 6 minutes. The solvent was then removed. The resulting oil was dissolve... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Secondary amine | Tertiary amine | C1COCCN1.c1ccccc1 | C1COCC[NH]1 | C1COCC[NH]1 | TsOH.HO- | null | 160 | null | C1COCCN1.Cc1ccc(S(=O)(=O)OC[C@@H](O)CC(C)(C)C)cc1>>CC(C)(C)C[C@H](O)CN1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-04f148b6dc834707877bee4335ee65b4 | CC(C)c1cc(C(C)C)c(S(=O)(=O)OC[C@@H](O)CC2CCCC2)c(C(C)C)c1.Clc1cc2nc[nH]c2cc1Cl>>O[C@@H](CC1CCCC1)Cn1cnc2cc(Cl)c(Cl)cc21 | C1(CCCC1)C[C@@H](COS(=O)(=O)C1=C(C=C(C=C1C(C)C)C(C)C)C(C)C)O.ClC1=CC2=C(N=CN2)C=C1Cl.C(=O)([O-])[O-].[K+].[K+]>>C1(CCCC1)C[C@@H](CN1C=NC2=C1C=C(C(=C2)Cl)Cl)O | CC(C)c1cc(C(C)C)c(S(=O)(=O)O[CH2:9][C@@H:2]([OH:1])[CH2:3][CH:4]2[CH2:5][CH2:6][CH2:7][CH2:8]2)c(C(C)C)c1.[nH:10]1[cH:11][n:12][c:13]2[cH:14][c:15]([Cl:16])[c:17]([Cl:18])[cH:19][c:20]12>>[OH:1][C@@H:2]([CH2:3][CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8]1)[CH2:9][n:10]1[cH:11][n:12][c:13]2[cH:14][c:15]([Cl:16])[c:17]([Cl:18])[c... | CC(C)c1cc(C(C)C)c(S(=O)(=O)OC[C@@H](O)CC2CCCC2)c(C(C)C)c1.Clc1cc2nc[nH]c2cc1Cl | O[C@@H](CC1CCCC1)Cn1cnc2cc(Cl)c(Cl)cc21 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 87d52f6de9c2fc6f21db22c5fc4d61265c101cb13821277fb4137c9cdfd96cb6 | 5d113adad2f4b994f74d03745c6fa87e33b0699dc5e5ea2c6f5563e07945c23c | c1ccc2c(c1)ncn2CCCC1CCCC1 | C-C(-C)-c1:c:c(-C(-C)-C):c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2](-[C:3])-[O;D1;H1:4]):c(-C(-C)-C):c:1.[c:5]:[c:6]1:[#7;a:7]:[c:8]:[nH;D2;+0:9]:[c:10]:1:[c:11]>>[C:3]-[C:2](-[O;D1;H1:4])-[CH2;D2;+0:1]-[n;H0;D3;+0:9]1:[c:8]:[#7;a:7]:[c:6](:[c:5]):[c:10]:1:[c:11] | 40 | [{"value": 40.0, "product": "C1(CCCC1)C[C@@H](CN1C=NC2=C1C=C(C(=C2)Cl)Cl)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.3, "product": "C1(CCCC1)C[C@@H](CN1C=NC2=C1C=C(C(=C2)Cl)Cl)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 160 | CELSIUS | null | null | Two large (2-5 mL) microwave reactor tubes were charged with (S)-2,4,6-Triisopropyl-benzenesulfonic acid 3-cyclopentyl-2-hydroxy-propyl ester (Example 6, Step A, 1.88 g, 4.6 mmol), 5,6-dichlorobenzimidazole (859 mg, 4.6 mmol), K2CO3 (1.27 g, 9.2 mmol) and DMF (4 mL). The tubes were then heated to 160° C. for 6 minutes.... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonate | null | c1ccccc1.c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | C1CCCC1.c1ccc2[nH]cnc2c1 | HO- | CN(C)C=O | 160 | null | CC(C)c1cc(C(C)C)c(S(=O)(=O)OC[C@@H](O)CC2CCCC2)c(C(C)C)c1.Clc1cc2nc[nH]c2cc1Cl>CN(C)C=O>O[C@@H](CC1CCCC1)Cn1cnc2cc(Cl)c(Cl)cc21 |
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