original_index int64 2 1.77M | extracted_from_file stringclasses 489
values | date_of_experiment timestamp[ns]date | grant_date timestamp[ns]date 1976-01-01 00:01:00 2016-01-01 00:09:00 | is_mapped bool 1
class | rxn_str stringlengths 87 6.12k | reactant_000 stringlengths 1 902 | reactant_001 stringlengths 1 902 ⌀ | reactant_002 null | agent_000 stringlengths 1 540 ⌀ | agent_001 stringlengths 1 852 ⌀ | agent_002 stringlengths 1 247 ⌀ | agent_003 null | agent_004 null | agent_005 null | agent_006 null | agent_007 null | agent_008 null | agent_009 null | agent_010 null | agent_011 null | agent_012 null | agent_013 null | agent_014 null | agent_015 null | agent_016 null | solvent_000 stringclasses 446
values | solvent_001 stringclasses 405
values | solvent_002 null | solvent_003 null | solvent_004 null | solvent_005 null | solvent_006 null | solvent_007 null | solvent_008 null | solvent_009 null | solvent_010 null | temperature float64 -230 30.1k ⌀ | rxn_time float64 0 2.16k ⌀ | procedure_details stringlengths 8 24.5k | product_000 stringlengths 1 484 | product_001 null | yield_000 float64 0 90,205,156,600B ⌀ | yield_001 float64 0 100M ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
1,701,674 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [F:1][C:2]([F:22])([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)[CH2:3][CH2:4][S:5][C:6]1[N:7]=[C:8]([CH3:14])[S:9][C:10]=1[C:11]([OH:13])=O.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.CN1CCOCC1.[F:52][C:53]1[CH:60]=[CH:59][C:56]([CH2:57][NH2:58])=[CH:55][CH:54]=1>CN(C=O)C>[F:22][C:2]([F:1])([C:15]1[CH:... | NCc1ccc(F)cc1 | Cc1nc(SCCC(F)(F)c2ccc(F)cc2)c(C(=O)O)s1 | null | CN(C)C(On1nnc2ccccc21)=[N+](C)C | F[B-](F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CN1CCOCC1 | null | null | null | null | null | null | null | null | null | 25 | 3 | To a solution of 4-[[3,3-difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-2-methyl-thiazole-5-carboxylic acid (0.25 g, 0.72 mmol) in DMF (4 ml) are added O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (347 mg, 1.08 mmol) and N-methylmorpholine (0.16 ml, 1.44 mmol) at 0° C. followed by the addition of ... | Cc1nc(SCCC(F)(F)c2ccc(F)cc2)c(C(=O)NCc2ccc(F)cc2)s1 | null | 58.3 | null |
891,619 | ord_dataset-11068b1e475b4c5b82e56726ab0dddb7 | null | 2009-01-01T00:07:00 | true | C([N:20]1[CH:24]=[C:23]([C:25]2[C:26]([O:31][C:32]3[CH:37]=[CH:36][C:35]([NH2:38])=[CH:34][CH:33]=3)=[N:27][CH:28]=[CH:29][CH:30]=2)[CH:22]=[N:21]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.FC(F)(F)C(O)=O>CO>[NH:20]1[CH:24]=[C:23]([C:25]2[C:26]([O:31][C:32]3[CH:37]=[CH:36][C:35]([NH2:38])=[CH:34][CH:33]=3)=[N:27][CH:28]=[C... | Nc1ccc(Oc2ncccc2-c2cnn(C(c3ccccc3)(c3ccccc3)c3ccccc3)c2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | 80 | 36 | In a 25 mL sealed tube, was added 4-(3-(1-trityl-1H-pyrazol-4-yl)pyridin-2-yloxy)benzenamine (0.150 g, 0.303 mmol), trifluoroacetic acid (0.23 mL, 3.0 mmol), and methanol (1.0 mL). The mixture was stirred at 80° C. for 36 hours. The mixture was concentrated. The residue was extracted into EtOAc, washed 1×NaHCO3, 1×NaCl... | Nc1ccc(Oc2ncccc2-c2cn[nH]c2)cc1 | null | null | null |
1,633,854 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [CH3:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]3[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=3)[CH:10]=2)=[C:6]([CH3:21])[N:5]=[C:4]([NH:22]C(=O)C)[CH:3]=1.Cl>C1COCC1>[CH3:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]3[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=3)[CH:10]=2)=[C:6]([CH3:21])[N:5]=[C:4... | CC(=O)Nc1cc(C)c(Oc2ccnc(-c3cnn(C)c3)c2)c(C)n1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 40 | null | A solution of N-(4,6-dimethyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)acetamide (692 mg, 2.051 mmol) in THF (25 mL) was treated with HCl (3 M, 3.4 mL, 10.2 mmol) and warmed at 40° C. for 17 h. The mixture was treated with satd. NaHCO3, extracted with EtOAc (2×) and the combined organics were dried... | Cc1cc(N)nc(C)c1Oc1ccnc(-c2cnn(C)c2)c1 | null | 73.6 | null |
1,273,315 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][NH:11][CH2:10][CH:9]2[N:13]([CH3:28])[C:14](=[O:27])[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([C:23]([F:26])([F:25])[F:24])[CH:16]=2)=[CH:4][CH:3]=1.[C:29]([O:33][C:34]([N:36]1[CH2:41][CH2:40][CH:39]([C:42](O)=[O:43])[CH2:38][CH2:37]1)=[O:35])([CH3:32])([CH3:31])... | COc1ccc(C(=O)N(C)C2CNCC2c2ccc(Cl)cc2)cc1C(F)(F)F | CC(C)(C)OC(=O)N1CCC(C(=O)O)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In analogy to the procedure described for the synthesis of example 87 (step c), the title compound 4-{(3SR,4RS)-3-(4-chloro-phenyl)-4-[(4-methoxy-3-trifluoromethyl-benzoyl)-methyl-amino]-pyrrolidine-1-carbonyl}-piperidine-1-carboxylic acid tert-butyl ester was prepared from N-[(3RS,4SR)-4-(4-chloro-phenyl)-pyrrolidin-3... | COc1ccc(C(=O)N(C)C2CN(C(=O)C3CCN(C(=O)OC(C)(C)C)CC3)CC2c2ccc(Cl)cc2)cc1C(F)(F)F | null | null | null |
316,491 | ord_dataset-fd1553bae35046c7a67523ff472cb5c3 | null | 1995-01-01T00:09:00 | true | [H-].[Na+].[N:3]1[C:11]([NH2:12])=[C:10]2[C:6]([N:7]=[CH:8][NH:9]2)=[N:5][CH:4]=1.[CH3:13]CCCCC>CN(C)C=O>[CH3:13][C:4]1[N:5]=[C:6]2[C:10]([NH:9][CH:8]=[N:7]2)=[C:11]([NH2:12])[N:3]=1 | CCCCCC | Nc1ncnc2nc[nH]c12 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | 0.33 | To a suspension of 114 mg (2.85 mmol) of 60% sodium hydride (previously washed with hexane) in 18 ml of anhydrous dimethylformamide 386 mg (2.85 mmol) of adenine was added, and the mixture was stirred for 20 minutes at room temperature. Then, 1.18 g (2.38 mmol) of (Z)-[1,2-bis(benzoyloxymethyl)] cyclopropylmethyl p-tol... | Cc1nc(N)c2[nH]cnc2n1 | null | null | null |
883,693 | ord_dataset-d728a2f811c0424cbcdb5a84d02b93ae | null | 2009-01-01T00:06:00 | true | Cl[CH2:2][N:3]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[N:4]1.[CH2:12]([CH:15]([C:18]#[N:19])[C:16]#[N:17])[CH:13]=[CH2:14].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:12]([C:15]([CH2:2][N:3]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[N:4]1)([C:18]#[N:19])[C:16]#[N:17])[CH:13]=[CH2:14] | C=CCC(C#N)C#N | FC(F)(F)c1ccn(CCl)n1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | 1.33 g of 1-(chloromethyl)-3-(trifluoromethyl)-1H-pyrazole and 0.76 g of allyl malononitrile were dissolved in 21 ml of N,N-dimethylformamide. 1.99 g of potassium carbonate was added to the solution under ice cooling with stirring, followed by stirring at room temperature for overnight. Water was added to the reaction ... | C=CCC(C#N)(C#N)Cn1ccc(C(F)(F)F)n1 | null | 31.3 | null |
1,266,936 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]([OH:17])=O)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC(OCC(C)C)=O.[C:26]1([C@H:32]([NH2:34])[CH3:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1COCC1.C(N(CC)CC)C>[C:26]1([C@H:32]([NH:34][C:15]([C@H:12]2[CH2:11][CH2:10][C@H:9]([NH:8][C:6](=[O:7])[O... | CC(C)(C)OC(=O)N[C@H]1CC[C@H](C(=O)O)CC1 | C[C@@H](N)c1ccccc1 | null | CC(C)COC(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 0 | 0.5 | Trans-4-tert-butoxycarbonylamino-cyclohexanecarboxylic acid (5 g, 20.5 mmol) was dissolved in THF, to which triethylamine (3 mL) was added. The reaction mixture was cooled to 0° C. and a solution of isobutyl chloroformate (2.8 g, 20.7 mmol) in THF was added dropwise. The resulting white suspension was stirred at room t... | C[C@@H](NC(=O)[C@H]1CC[C@H](NC(=O)OC(C)(C)C)CC1)c1ccccc1 | null | null | null |
1,318,769 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | [O:1]1[C:3]2([CH2:8][CH2:7][S:6][CH2:5][CH2:4]2)[CH2:2]1.[OH:9][C:10]1[CH:15]=[C:14]([CH3:16])[C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]=[O:24])[CH:18]=2)=[C:12]([CH3:25])[CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[OH:1][C:3]1([CH2:2][O:9][C:10]2[CH:15]=[C:14]([CH3:16])[C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[C... | C1CC2(CCS1)CO2 | Cc1cc(O)cc(C)c1-c1cccc(C=O)c1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 100 | 12 | To a solution of 1-oxa-6-thiaspiro[2.5]octane (6.33 g, 48.6 mmol) and 4′-hydroxy-2′,6′-dimethylbiphenyl-3-carbaldehyde (10.0 g, 44.2 mmol) in N,N-dimethylformamide (150 mL) was added potassium carbonate (6.11 g, 44.2 mmol) at room temperature, and the mixture was stirred at 100° C. for 12 hr. The reaction mixture was c... | Cc1cc(OCC2(O)CCSCC2)cc(C)c1-c1cccc(C=O)c1 | null | 78.1 | null |
1,640,879 | ord_dataset-bcc0b01d4f58457a8733b10a099f43ba | null | 2015-01-01T00:10:00 | true | Cl.[NH2:2][C@H:3]([C:8]([O:10][CH3:11])=[O:9])[CH2:4][CH:5]([CH3:7])[CH3:6].C(N(CC)CC)C.[F:19][C:20]1[CH:30]=[CH:29][CH:28]=[CH:27][C:21]=1[CH:22]=[CH:23][C:24](O)=[O:25].CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[F:19][C:20]1[CH:30]=[CH:29][CH:28]=[CH:27][C:21]=1[CH:22]=[CH:23][C:24]([NH:2][C@H:3]([C:8]([O:10][CH3:11])=[O:9])[CH2:4]... | O=C(O)C=Cc1ccccc1F | COC(=O)[C@@H](N)CC(C)C | null | CCN=C=NCCCN(C)C | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | The same procedures as in Example 2 were carried out from methyl L-leucinate hydrochloride (3.0 g), triethylamine (2.5 mL), 2-fluorocinnamic acid (3.0 g), WSC.HCl (3.5 g), and methylene chloride (100 mL), to give the captioned compound (4.3 g, 88%) as crystals. | COC(=O)[C@H](CC(C)C)NC(=O)C=Cc1ccccc1F | null | 88.8 | null |
1,624,422 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [F:1][C:2]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:3]=1[O:4][C:5]1[C:6]([C:15]2[CH:16]=[C:17]([CH3:23])[C:18](=[O:22])[N:19]([CH3:21])[CH:20]=2)=[N:7][C:8](S(C)(=O)=O)=[N:9][CH:10]=1.[CH2:29]([S:31]([NH2:34])(=[O:33])=[O:32])[CH3:30]>>[F:1][C:2]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:3]=1[O:4][C:5]1[C:6]([C:15]2[CH:16... | CCS(N)(=O)=O | Cc1cc(-c2nc(S(C)(=O)=O)ncc2Oc2ccc(F)cc2F)cn(C)c1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound of Example 149, step 4 was treated with EtSO2NH2 instead of MeSO2NH2 in a manner similar to Example 152, step 6 to give the title compound. 1H NMR (DMSO-d6, 400 MHz) δ 9.07 (s, 1H), 8.42 (s, 1H), 8.15 (s, 1H), 8.11 (s, 1H), 7.03-6.97 (m, 1H), 6.91-6.87 (m, 1H), 3.66-3.61 (m, 5H), 2.22 (s, 3H), 1.44 (... | CCS(=O)(=O)Nc1ncc(Oc2ccc(F)cc2F)c(-c2cc(C)c(=O)n(C)c2)n1 | null | null | null |
1,243,026 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [C:1]([C:3]1([C:6]2[CH:7]=[C:8]([CH:36]=[CH:37][CH:38]=2)[C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]3[CH:20]=[N:21][C:22]([NH:25][S:26]([C:29]4[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=4)(=[O:28])=[O:27])=[CH:23][CH:24]=3)[CH:13]=2)=[O:10])[CH2:5][CH2:4]1)#[N:2].C(N(C(C)C)C(C)C)C.I[CH2:49][C:50]... | NC(=O)CI | Cc1ccc(S(=O)(=O)Nc2ccc(Oc3cccc(NC(=O)c4cccc(C5(C#N)CC5)c4)c3)cn2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 0.25 | To a solution of 3-(1-cyanocyclopropyl)-N-{3-[(6-{[(4-methylphenyl)sulfonyl]amino}pyridin-3-yl)oxy]phenyl}benzamide (2.5 g, 4.77 mmol) in N,N-dimethylformamide (15 mL) was added N-ethyl-N-isopropylpropan-2-amine (0.90 mL, 5.01 mmol), and the mixture was stirred at room temperature for 15 min. 2-Iodoacetamide (927 mg, 5... | Cc1ccc(S(=O)(=O)N=c2ccc(Oc3cccc(NC(=O)c4cccc(C5(C#N)CC5)c4)c3)cn2CC(N)=O)cc1 | null | 77.1 | null |
1,285,163 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [CH3:1][N:2]([CH3:34])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[C:20](=O)[C:19]3[C:18]([C:22](OCC)=[O:23])=[CH:17][CH:16]=[CH:15][C:14]=3[NH:13][CH:12]2[C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)=[CH:7][CH:6]=1)=[O:4].O.[NH2:36][NH2:37]>CO>[F:33][C:30]1[CH:31]=[CH:32][C:27]([CH:12]2[NH:13][C:14]3[C:19]4[C:20]... | NN | CCOC(=O)c1cccc2c1C(=O)C(c1ccc(C(=O)N(C)C)cc1)C(c1ccc(F)cc1)N2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CO | null | null | null | null | null | null | null | null | null | 35 | 2 | A mixture of ethyl 3-(4-(dimethylcarbamoyl)phenyl)-2-(4-fluorophenyl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate (400 mg, 0.87 mmol) and hydrazine monohydrate (85%, 10 mL) were dissolved in MeOH (20 mL), and stirred at 35° C. for 2 h. The mixture was concentrated under reduced pressure. The resulting mixture was f... | CN(C)C(=O)c1ccc(C2c3n[nH]c(=O)c4cccc(c34)NC2c2ccc(F)cc2)cc1 | null | 54 | null |
1,193,592 | ord_dataset-4e81c470cc3b429faf5e1caa50f70a98 | null | 2012-01-01T00:08:00 | true | [O:1]=[C:2]1[CH2:7][O:6][C:5]2[CH:8]=[CH:9][C:10]([CH:12]=O)=[N:11][C:4]=2[NH:3]1.[CH3:14][O:15][C:16]1[N:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[N:22]=[CH:21][CH:20]=[C:19]2[N:26]1[CH:34]=[C:33]2[C:28]([CH2:29][CH2:30][CH:31]([NH2:35])[CH2:32]2)=[N:27]1.[BH4-].[Na+].[OH-].[Na+]>CN(C=O)C.CO>[CH3:14][O:15][C:16]1[N:17]=[C:... | COc1ccc2nccc(-n3cc4c(n3)CCC(N)C4)c2n1 | O=Cc1ccc2c(n1)NC(=O)CO2 | null | [BH4-] | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 8 | To a solution of 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carbaldehyde (153 mg, 0.858 mmol) in DMF (1.36 mL) was added 2-(6-methoxy-[1,5]naphthyridin-4-yl)-4,5,6,7-tetrahydro-2H-indazol-5-ylamine (84.4 mg, 0.286 mmol). The reaction mixture was stirred overnight at RT. NaBH4 (37.6 mg, 0.572 mmol) was then added ... | COc1ccc2nccc(-n3cc4c(n3)CCC(NCc3ccc5c(n3)NC(=O)CO5)C4)c2n1 | null | 3.5 | null |
533,731 | ord_dataset-b1a34bc8c1204d51a772ed27396c794e | null | 2002-01-01T00:02:00 | true | CO[C:3]([O:8][CH3:9])(OC)OC.C(O)(=O)C.[C:14]1([S:20]([NH:23][C:24](=[O:46])[C:25]2[CH:30]=[CH:29][C:28]([NH2:31])=[C:27]([NH:32][CH2:33][C:34]3[CH:39]=[CH:38][C:37]([C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)=[CH:36][CH:35]=3)[CH:26]=2)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CO>[C:14]1([S:20]([NH:2... | COC(OC)(OC)OC | Nc1ccc(C(=O)NS(=O)(=O)c2ccccc2)cc1NCc1ccc(-c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | CO | null | null | null | null | null | null | null | null | null | 80 | 2 | Tetramethoxymethane (0.250 g) is added to an acetic acid solution (3 ml) of N-benzenesulfonyl-4-amino-3-(biphenyl-4-ylmethylamino)benzamide (0.400 g), and the solution is stirred for two hours at 80° C. Methanol is added to the reaction solution, and precipitated crystals are collected. The crystals are washed in a mix... | COc1nc2ccc(C(=O)NS(=O)(=O)c3ccccc3)cc2n1Cc1ccc(-c2ccccc2)cc1 | null | 64.4 | null |
1,478,673 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:11]2[CH2:14][CH:13]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12]2)=[C:6]([CH:10]=1)[C:7]([OH:9])=O.Cl.[NH2:23][C:24]1([C:27]2[CH:36]=[CH:35][C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:29][CH:28]=2)[CH2:26][CH2:25]1>>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:11]2[CH2:14][CH:13]([O:... | O=C(O)c1cc(Cl)cnc1N1CC(Oc2ccccc2)C1 | COC(=O)c1ccc(C2(N)CC2)cc1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound (D145) (225 mg) was prepared according to the experimental procedure described in Description 142 starting from 5-chloro-2-(3-phenoxyazetidin-1-yl)nicotinic acid (D101) (140 mg, 0.46 mmol) and methyl 4-(1-aminocyclopropyl)benzoate hydrochloride (D7) (104 mg, 0.40 mmol). | COC(=O)c1ccc(C2(NC(=O)c3cc(Cl)cnc3N3CC(Oc4ccccc4)C3)CC2)cc1 | null | 117.7 | null |
973,063 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | Cl[C:2]1[C:11]2[C:6](=[C:7]([O:14][CH:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[O:5][C:4](=[O:20])[CH:3]=1.[NH2:21][CH2:22][C:23]([OH:25])=[O:24].C(N(CC)CC)C>C(O)C>[CH:15]1([O:14][C:7]2[C:8]([O:12][CH3:13])=[CH:9][CH:10]=[C:11]3[C:6]=2[O:5][C:4](=[O:20])[CH:3]=[C:2]3[NH:21][CH2:22][C:... | NCC(=O)O | COc1ccc2c(Cl)cc(=O)oc2c1OC1CCCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 75 | 48 | A mixture of 4-chloro-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one (170 mg, 0.58 mmol), glycine (52 mg, 0.69 mmol), triethylamine (0.2 mL, 1.4 mmol), and ethanol (2 mL) was heated at 75° C. in a sealed vial. After 2 d, more glycine (136 mg, 1.8 mmol) and triethylamine (0.3 mL, 2.2 mmol) were added. The reaction was he... | COc1ccc2c(NCC(=O)O)cc(=O)oc2c1OC1CCCC1 | null | null | null |
1,532,013 | ord_dataset-8d5c200bca27407ab9febe7598e16458 | null | 2015-01-01T00:01:00 | true | [Si]([O:8][CH2:9][C:10]1([CH3:37])[S:16][CH2:15][CH2:14][N:13]2[C:17]([C:20]3([C:23]4[CH:28]=[CH:27][C:26]([C:29]5[CH:30]=[N:31][CH:32]=[C:33]([CH:36]=5)[C:34]#[N:35])=[CH:25][CH:24]=4)[CH2:22][CH2:21]3)=[N:18][N:19]=[C:12]2[CH2:11]1)(C(C)(C)C)(C)C.Cl>CO>[OH:8][CH2:9][C:10]1([CH3:37])[S:16][CH2:15][CH2:14][N:13]2[C:17]... | CC1(CO[Si](C)(C)C(C)(C)C)Cc2nnc(C3(c4ccc(-c5cncc(C#N)c5)cc4)CC3)n2CCS1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | A solution of the compound (238 mg, 0.45 mmol) obtained in Example 62-1) and 4 M hydrochloric acid (1,4-dioxane solution, 1 mL) in methanol (4 mL) was stirred at room temperature for 15 h. The reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogencarbonate was added to the residue, ... | CC1(CO)Cc2nnc(C3(c4ccc(-c5cncc(C#N)c5)cc4)CC3)n2CCS1 | null | 87.3 | null |
822,669 | ord_dataset-ec58fad8331a42c5a67ad75aac6713b4 | null | 2008-01-01T00:05:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[N:12][N:11]3[C:14](=[O:17])[NH:15][N:16]=[C:10]3[C:9]=2[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[O:44]1[CH2:49][CH2:48][N:47]([C:50]2[N:55]=[CH:54][C:53]([CH2:56]O)=[CH:52][CH:51]=2)[CH2:46][CH2:45]1>C1COC... | OCc1ccc(N2CCOCC2)nc1 | O=c1[nH]nc2c(-c3ccc(Cl)cc3)c(-c3ccc(Cl)cc3)cnn12 | null | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared using 7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one, (50 mg, 0.14 mmol), prepared as described in Example 1, Ph3P (110 mg, 0.42 mmol) and (6-morpholinopyridin-3-yl)methanol (29 mg, 0.14 mmol) in THF (1.0 mL) and by following the procedure described in Example 2. The t... | O=c1n(Cc2ccc(N3CCOCC3)nc2)nc2c(-c3ccc(Cl)cc3)c(-c3ccc(Cl)cc3)cnn12 | null | 27.5 | null |
1,671,430 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [OH:1][CH2:2][C@H:3]1[CH2:14][CH2:13][C:12]2[S:11][C:10]3[N:9]=[CH:8][N:7]=[C:6]([O:15][CH:16]4[CH2:21][CH2:20][CH:19]([N:22]([CH3:30])[C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:18][CH2:17]4)[C:5]=3[C:4]1=2.[CH3:31][S:32](Cl)(=[O:34])=[O:33].C(N(CC)CC)C>C(Cl)Cl>[CH3:31][S:32]([O:1][CH2:2][C@H:3]1[CH2:... | CN(C(=O)OC(C)(C)C)C1CCC(Oc2ncnc3sc4c(c23)[C@@H](CO)CC4)CC1 | CS(=O)(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 25 | 2 | A solution of tert-butyl N-(4-[[(3S)-3-(hydroxymethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2 (6),9,11-tetraen-12-yl]oxy]cyclohexyl)-N-methylcarbamate (691 mg, 1.59 mmol, 1.00 equiv) in 4 mL of DCM was added MsCl (366 mg, 3.18 mmol, 2.00 equiv) and triethylamine (643 mg, 6.35 mmol, 4.00 equiv) at 0° C. un... | CN(C(=O)OC(C)(C)C)C1CCC(Oc2ncnc3sc4c(c23)[C@@H](COS(C)(=O)=O)CC4)CC1 | null | 110.6 | null |
920,847 | ord_dataset-8e59bd24817446f7b1c68e805b8e5f1d | null | 2009-01-01T00:11:00 | true | [CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:16]=[C:15]([NH2:17])[CH:14]=[C:6]([C:7]([N:9]([CH3:13])[CH2:10][CH2:11][CH3:12])=[O:8])[CH:5]=1.N1C=CC=CC=1.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>ClCCl>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:16]=[C:15]([NH:17][S:26]([CH3:25])(=[O:28])=[O:27])[CH:14]=[C:6]([C:7]([N:9]([CH3:13])[CH2:10][CH2:... | CS(=O)(=O)Cl | CCCN(C)C(=O)c1cc(N)cc(C(=O)OC)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | c1ccncc1 | null | null | null | null | null | null | null | null | null | 25 | 72 | Dissolve 5-amino-N-methyl-N-propyl-isophthalamic acid methyl ester (1.64 g, 6.55 mmol) in dichloromethane (20 mL) and add pyridine (620 mg, 6.88 mmol) and methanesulfonyl chloride (788 mg, 6.88 mmol). Stir at room temperature for 72 h, dilute with dichloromethane, wash with 0.1 N citric acid and saturated aqueous sodiu... | CCCN(C)C(=O)c1cc(NS(C)(=O)=O)cc(C(=O)OC)c1 | null | null | null |
136,427 | ord_dataset-3007013966624a1096d71142f31cb5a3 | null | 1985-01-01T00:10:00 | true | Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[C:8]3[S:14][CH2:13][CH2:12][N:9]32)=[CH:4][C:3]=1[F:19].[C:20]([O:24][C:25]([NH:27][CH:28]1[CH2:32][CH2:31][NH:30][CH2:29]1)=[O:26])([CH3:23])([CH3:22])[CH3:21]>N1C=CC=CC=1>[F:19][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[N:30]1[CH2:31][CH2:32][CH... | O=C(O)c1c2n(c3cc(Cl)c(F)cc3c1=O)CCS2 | CC(C)(C)OC(=O)NC1CCNC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 9.0 g (30 mmol) of 8-chloro-7-fluoro-5-oxo-1,2-dihydro-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid, 8.37 g (45 mmol) of 3-(t-butoxycarbonylamino)pyrrolidine and 100 ml of pyridine is heated at reflux for 18 hours. The solvent is removed in vacuo and the residue triturated with water. The solid which form... | CC(C)(C)OC(=O)NC1CCN(c2cc3c(cc2F)c(=O)c(C(=O)O)c2n3CCS2)C1 | null | null | null |
936,136 | ord_dataset-90b0aa1f83334a02919b2be3a1c04542 | null | 2010-01-01T00:02:00 | true | [Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[CH3:9].[C:10]1(=O)[O:15][C:13](=[O:14])[CH:12]=[CH:11]1>C(O)(=O)C>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]2[C:13](=[O:14])[CH:12]=[CH:11][C:10]2=[O:15])=[CH:4][C:3]=1[CH3:9] | O=C1C=CC(=O)O1 | Cc1cc(N)ccc1Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | 115 | 0.42 | 4-Bromo-3-methylaniline (1.55 g, 8.33 mmol) and maleic anhydride (0.898 g, 9.16 mmol) were dissolved in acetic acid (10 mL) and heated at 115° C. for 12 h. The reaction was then cooled to 25° C. and the acetic acid was removed in vacuo. The resulting residue was suspended in 5% K2CO3 (100 mL), stirred for 25 minutes fo... | Cc1cc(N2C(=O)C=CC2=O)ccc1Br | null | 74.4 | null |
1,763,293 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:26]#[N:27])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:20][C:21]3([CH3:24])[CH2:23][CH2:22]3)[C:17](O)=[O:18])[C:10](=[O:25])[CH:9]=2)[CH:7]=1.[NH2:28][C:29]1[CH:41]=[CH:40][C:32]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[CH:31][CH:30]=1.CC(C)N=C=NC(C... | CC(C)(C)OC(=O)c1ccc(N)cc1 | COc1cn(C(CC2(C)CC2)C(=O)O)c(=O)cc1-c1cc(Cl)ccc1C#N | null | CC(C)N=C=NC(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | null | 95.0 mg (246 μmol) of 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(1-methylcyclopropyl)propanoic acid (racemate), 47.5 mg (246 μmol) of tert-butyl 4-aminobenzoate, 34.9 mg (246 μmol) of Oxima and 38.3 μl (246 μmol) of DIC in 2.5 ml of dimethylformamide were reacted according to General Method 5B. Y... | COc1cn(C(CC2(C)CC2)C(=O)Nc2ccc(C(=O)OC(C)(C)C)cc2)c(=O)cc1-c1cc(Cl)ccc1C#N | null | null | null |
1,759,442 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [NH:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[C:9]3[N:17]=[C:16]([C:18]4[CH:19]=[C:20]([NH:24][S:25]([C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)(=[O:27])=[O:26])[CH:21]=[N:22][CH:23]=4)[CH:15]=[CH:14][C:10]=3[N:11]=[CH:12][N:13]=2)[CH2:3][CH2:2]1.[C:34](Cl)([CH3:36])=[O:35]>C(Cl)Cl.O>[C:34]([N:1]1[CH2:6][CH2:5][CH:4]([O:... | CC(=O)Cl | O=S(=O)(Nc1cncc(-c2ccc3ncnc(OC4CCNCC4)c3n2)c1)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O | null | null | null | null | null | null | null | null | null | 25 | 2 | To a solution of N-(5-(4-(piperidin-4-yloxy)pyrido[3,2-d]pyrimidin-6-yl)pyridin-3-yl)benzene-sulfonamide (0.082 g, 0.177 mmol) in DCM (0.886 ml) was added TEA (0.062 ml, 0.443 mmol) at room temperature. After stirring for 2 hours at room temperature, AcCl (0.019 ml, 0.266 mmol) was added to the mixture at 0° C. After s... | CC(=O)N1CCC(Oc2ncnc3ccc(-c4cncc(NS(=O)(=O)c5ccccc5)c4)nc23)CC1 | null | 7.8 | null |
303,719 | ord_dataset-bfcf5a01f1a04ec585ba3f28cb93c8c9 | null | 1995-01-01T00:01:00 | true | [S:1]([C:5]1[CH:13]=[C:12]([C:14]([OH:16])=[O:15])[CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])([OH:4])(=[O:3])=[O:2].C([O:20][C:21](=[O:23])[CH3:22])(=O)C>>[C:21]([C:22]1[CH:11]=[CH:10][C:6]([C:7]([O:8][C:7](=[O:9])[C:6]2[CH:10]=[CH:11][C:12]([C:14]([OH:16])=[O:15])=[CH:13][C:5]=2[S:1]([OH:4])(=[O:3])=[O:2])=[O:8])=[C:5]... | O=C(O)c1ccc(C(=O)O)c(S(=O)(=O)O)c1 | CC(=O)OC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 100 | 4 | A dry 500 ml 3-neck flask was equipped with a condenser, stirrer and thermometer under a nitrogen atmosphere. The vessel was charged with 2-sulfoterephthalic acid (100 g, 447 mmol).and acetic anhydride (127 ml). The solution was stirred at 100° C. for 4 hours and then cooled to room temperature (the reaction mixture be... | O=C(O)c1ccc(C(=O)OC(=O)c2ccc(C(=O)O)cc2S(=O)(=O)O)c(S(=O)(=O)O)c1 | null | null | null |
1,647,017 | ord_dataset-bcc0b01d4f58457a8733b10a099f43ba | null | 2015-01-01T00:10:00 | true | C([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][CH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)=[CH:13][CH:12]=[CH:11][C:10]=2[O:22][CH3:23])=O)C.[C:24]([N:28]=[C:29]=[O:30])([CH3:27])([CH3:26])[CH3:25]>>[C:24]([N:28]1[C:4](=[O:3])[C:6]2[CH:7]=[N:8][C:9]3[C:10]([O:22][CH3:23])=[CH:11][CH:12]=[CH:13][C:14]=3[C:15]... | CC(C)(C)N=C=O | CCOC(=O)c1cnc2c(OC)cccc2c1NC1CCCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 3-tert-Butyl-1-cyclopentyl-7-methoxy-1H-pyrimido[5,4-c]quinoline-2,4-dione (18 mg) was prepared from 4-cyclopentylamino-8-methoxy-quinoline-3-carboxylic acid ethyl ester (0.10 mmol) and tert-butyl isocyanate (0.4 mmol) following general procedure C. LCMS: m/z 368 [M+1]+. | COc1cccc2c1ncc1c(=O)n(C(C)(C)C)c(=O)n(C3CCCC3)c12 | null | 49 | null |
1,562,339 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [CH3:1][C:2]([S:5](/[N:7]=[CH:8]/[C:9]1[N:10]=[C:11]([CH3:14])[NH:12][CH:13]=1)=[O:6])([CH3:4])[CH3:3].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([Mg]Br)=[CH:19][CH:18]=1.C1COCC1>C(Cl)Cl>[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH:8]([C:9]2[N:10]=[C:11]([CH3:14])[NH:12][CH:13]=2)[NH:7][S:5]([C:2]([CH3:1])([CH3:3])[C... | Cc1nc(/C=N/S(=O)C(C)(C)C)c[nH]1 | COc1ccc([Mg]Br)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | ClCCl | null | null | null | null | null | null | null | null | null | -78 | 1 | To a 100 ml round bottom flask containing −78° C. solution of 2-methyl-N-((1E)-(2-methyl-1H-imidazol-4-yl)methylene]propane-2-sulfinamide (1.170 g, 5.490 mmol) in 25.0 ml of CH2Cl2 was added dropwise 1.0 N 4-methoxyphenylmagnesium bromide in THF (8.230 ml, 8.230 mmol). The resulting solution was stirred at −78° C. for ... | COc1ccc(C(NS(=O)C(C)(C)C)c2c[nH]c(C)n2)cc1 | null | 42 | null |
1,611,554 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | C([Li])CCC.[CH3:6][C:7]1[O:8][CH:9]=[CH:10][CH:11]=1.[CH3:12][C:13]1([CH:17]=[O:18])[CH2:16][O:15][CH2:14]1.[Cl-].[NH4+]>CCCCCC.O1CCCC1>[CH3:6][C:7]1[O:8][C:9]([CH:17]([C:13]2([CH3:12])[CH2:16][O:15][CH2:14]2)[OH:18])=[CH:10][CH:11]=1 | CC1(C=O)COC1 | Cc1ccco1 | null | [Cl-] | [Li]CCCC | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCCCC | C1CCOC1 | null | null | null | null | null | null | null | null | null | -70 | 3 | 12.0 ml (30 mmol, 1.7 eq) of a 2.5 M solution of n-butyllithium in hexane were added dropwise to a solution of 2.46 g (30 mmol, 1.7 eq) of 2-methylfuran in 50 ml of tetrahydrofuran cooled to −70° C. The reaction medium was stirred and allowed to return to ambient temperature for 3 hours. The reaction medium was cooled ... | Cc1ccc(C(O)C2(C)COC2)o1 | null | 92.1 | null |
140,538 | ord_dataset-a2a0fbbcd49a46ffaa432d7ceae8a506 | null | 1986-01-01T00:02:00 | true | [Cl:1][C:2]1[C:3]([CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]2[NH:14][CH:15]=[CH:16][C:17](=[O:19])[N:18]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[N:20]1[CH:25]=[CH:24][C:23]([CH:26]=[O:27])=[CH:22][CH:21]=1>Cl>[Cl:1][C:2]1[C:3]([CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]2[NH:14][CH:15]=[C:16]([CH:26]([C:23]3[CH:24]=[CH:25][N:20... | O=Cc1ccncc1 | O=c1cc[nH]c(NCCCCc2ncccc2Cl)n1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 2-[[4-(3-Chloro-2-pyridyl)butyl]amino]-4-(1H)-pyrimidinone (1.37 g) and pyridine 4-aldehyde (0.52 g) were refluxed in concentrated hydrochloric acid (5 ml) for 24 hours. The reaction mixture was evaporated under reduced pressure to afford an oil which was partitioned between chloroform (25 ml) and water (25 ml) with th... | O=c1nc(NCCCCc2ncccc2Cl)[nH]cc1C(O)c1ccncc1 | null | 80.1 | null |
1,220,083 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | [N+:1]([O-:4])(O)=[O:2].[F:5][C:6]1[CH:13]=[C:12]([OH:14])[CH:11]=[CH:10][C:7]=1[C:8]#[N:9]>C(O)(=O)C>[F:5][C:6]1[CH:13]=[C:12]([OH:14])[C:11]([N+:1]([O-:4])=[O:2])=[CH:10][C:7]=1[C:8]#[N:9] | O=[N+]([O-])O | N#Cc1ccc(O)cc1F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | 40 | null | Nitric acid (0.326 mL, 7.29 mmol) 70% was added dropwise to a stirred solution of 2-fluoro-4-hydroxybenzonitrile (1 g, 7.29 mmol) in acetic acid (20 mL). The resulting solution was warmed to 40° C. for 24 hr. Solvent removed under reduced pressure to afford a yellow solid. Recrystallisation from EtOH (˜15 mL) afforded ... | N#Cc1cc([N+](=O)[O-])c(O)cc1F | null | 30.2 | null |
572,771 | ord_dataset-f4512fe8cd804ac79da66cbc0c2b9d42 | null | 2002-01-01T00:12:00 | true | [CH:1]([C:4]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]3[N:25]=[C:24]([CH3:26])[O:23][N:22]=3)[CH:16]=2)[C:7]2[C:8](=[O:12])[NH:9][CH:10]=[CH:11][C:6]=2[N:5]=1)([CH3:3])[CH3:2].[C:27]([C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][CH:34]=1)#[N:28]>ClCCl>[CH:1]([C:4]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][CH... | N#Cc1cccc(B(O)O)c1 | Cc1nc(-c2cccc(Cn3c(C(C)C)nc4cc[nH]c(=O)c43)c2)no1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | null | By reaction of 2-isopropyl-3-[3-(5-methyl-[1,2,4]oxadiazol-3-yl)benzyl]-3,5-dihydroimidazo[4,5-c]pyridin-4-one with 3-cyanophenylboronic acid under copper acetate catalysis in dichloromethane, 2-isopropyl-3-[3-(5-methyl-[1,2,4]oxadiazol-3-yl)benzyl]-5-(3-cyanophenyl)-3,5-dihydroimidazo[4,5-c]pyridin-4-one is obtained. ... | Cc1nc(-c2cccc(Cn3c(C(C)C)nc4ccn(-c5cccc(C#N)c5)c(=O)c43)c2)no1 | null | null | null |
1,122,338 | ord_dataset-285df12e34cd46e993e3c8ebc3a8962a | null | 2012-01-01T00:01:00 | true | [Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.[CH:11]([N:14]1[CH2:19][CH2:18][CH:17]([NH:20][S:21]([CH2:24][CH2:25][NH2:26])(=[O:23])=[O:22])[CH2:16][CH2:15]1)([CH3:13])[CH3:12]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:26][CH2:25][CH2:24][S:21](=[O:23])(=[O:22])[NH:20][CH:17]2[CH2:18][CH2:19][N:14]([... | O=C(O)c1ccc(Cl)cc1 | CC(C)N1CCC(NS(=O)(=O)CCN)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 4-Chloro-N-[2-(1-isopropyl-piperidin-4-ylsulfamoyl)-ethyl]-benzamide was prepared by an analogous procedure as described in example 9 starting from 104 mg (1.1 equiv.) 4-chloro-benzoic acid and 150 mg (0.60 mmol) 2-amino-ethanesulfonic acid (1-isopropyl-piperidin-4-yl)-amide. Final purification by preparative RP-HPLC (... | CC(C)N1CCC(NS(=O)(=O)CCNC(=O)c2ccc(Cl)cc2)CC1 | null | null | null |
625,337 | ord_dataset-e44331dc51de453ca14b7032593c1958 | null | 2004-01-01T00:02:00 | true | [NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.F[C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:16])[CH3:15])=[CH:10][CH:9]=1>O>[N:1]1([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:16])[CH3:15])=[CH:10][CH:9]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1 | CC(=O)c1ccc(F)cc1 | C1COCCN1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 120 | null | A mixture of morpholine (3.2 g, 37 mmol) and 1-(4-fluorophenyl) ethanone (1.5 g, 11 mmol) is heated at 120° C. The conversion of the 1-(4-fluorophenyl) ethanone is complete after 10 hours. Water (10 ml) is than added into the reaction mixture. The precipitate is filtered off, washed with water and dried under vacuum (3... | CC(=O)c1ccc(N2CCOCC2)cc1 | null | 93 | null |
1,232,470 | ord_dataset-e96f5a2842f14e5380461c234100f05a | null | 2012-01-01T00:12:00 | true | [NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]3[CH:13]=[C:14]([NH:19][C:20](=[O:32])[C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([C:27]5([C:30]#[N:31])[CH2:29][CH2:28]5)[CH:22]=4)[CH:15]=[CH:16][C:17]=3[CH3:18])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH:33]1([C:36](Cl)=[O:37])[CH2:35][CH2:34]1>CN(C)C1C=CN=CC=1>[C:30]([C:27]1([C:23]2[... | O=C(Cl)C1CC1 | Cc1ccc(NC(=O)c2cccc(C3(C#N)CC3)c2)cc1Oc1ccc2nc(N)sc2c1 | null | CN(C)c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Using N-{3-[(2-amino-1,3-benzothiazol-6-yl)oxy]-4-methylphenyl}-3-(1-cyanocyclopropyl)benzamide (0.11 g, 0.25 mmol), cyclopropanecarbonyl chloride (0.21 g, 2.0 mmol), and N,N-dimethylpyridine-4-amine (0.24 g, 2.0 mmol), and in the same manner as in Example A29(vi), the title compound (42 mg, 33%) was obtained as a pale... | Cc1ccc(NC(=O)c2cccc(C3(C#N)CC3)c2)cc1Oc1ccc2nc(NC(=O)C3CC3)sc2c1 | null | 33 | null |
13,743 | ord_dataset-7f88a5da29d74264aae5239be74b3981 | null | 1976-01-01T00:10:00 | true | [C:1]([NH:4][C@H:5]1[C@@H:12]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C@@H:11]([CH2:21][O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[O:10][C@@H:7]([O:8][CH3:9])[C@@H:6]1[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)(=[O:3])[CH3:2].[H-].[Na+].[CH3:40]I>CN(C=O)C>[CH3:4... | CO[C@@H]1O[C@H](COCc2ccccc2)[C@H](OCc2ccccc2)[C@H](NC(C)=O)[C@H]1OCc1ccccc1 | CI | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | null | Dissolve methyl 3-acetamido-3-deoxy-2,4,6-tri-O-benzyl-β-D-galactopyranoside (5.05 g.) in dry DMF (100 ml.). With stirring in an atomsphere of dry nitrogen add 0.25 g. of sodium hydride and allow the mixture to stir for 1 hour. Add methyl iodide (2.0 g.) and continue stirring at room temperature for 16 hours. Evaporate... | CO[C@@H]1O[C@H](COCc2ccccc2)[C@H](OCc2ccccc2)[C@H](N(C)C(C)=O)[C@H]1OCc1ccccc1 | null | null | null |
1,545,129 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | Cl.[NH2:2][CH2:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1.Br[C:13]1[CH:22]=[N:21][CH:20]=[CH:19][C:14]=1[C:15]([O:17][CH3:18])=[O:16]>>[C:8]([C:7]1[CH:10]=[CH:11][C:4]([CH2:3][NH:2][C:19]2[CH:20]=[N:21][CH:22]=[CH:13][C:14]=2[C:15]([O:17][CH3:18])=[O:16])=[CH:5][CH:6]=1)#[N:9] | COC(=O)c1ccncc1Br | N#Cc1ccc(CN)cc1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared in 4% yield from 4-(aminomethyl)-benzonitrile hydrochloride and methyl 3-bromoisonicotinate according to the procedure for Preparation 4A. 1H NMR (500 MHz, CDCl3): δ 8.07 (s, 1H), 7.97 (d, 2H, J=5.0 Hz), 7.63-7.70 (m, 3H), 7.46 (d, 2H, J=8.3 Hz), 4.61 (d, 2H, J=6.1 Hz), 3.94 (s, 3H). [M+... | COC(=O)c1ccncc1NCc1ccc(C#N)cc1 | null | 4 | null |
184,911 | ord_dataset-8537fa92abf34c849134600c0c2bbcc7 | null | 1989-01-01T00:02:00 | true | [S:1]([OH:11])(=[O:10])([C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1)=[O:2].Cl[C:13]1[C:22]2[C:17](=[CH:18][C:19]([Cl:23])=[CH:20][CH:21]=2)[N:16]=[N:15][CH:14]=1>O.C(O)C>[Cl:23][C:19]1[CH:18]=[C:17]2[C:22]([C:13]([NH:9][C:6]3[CH:5]=[CH:4][C:3]([S:1]([OH:11])(=[O:10])=[O:2])=[CH:8][CH:7]=3)=[CH:14][N:15]=[N:16]2)=[... | Nc1ccc(S(=O)(=O)O)cc1 | Clc1ccc2c(Cl)cnnc2c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCO | null | null | null | null | null | null | null | null | null | 70 | 8 | Sulphanilic acid (1.95 g) in water (75 ml) and ethanol (10 ml) at 70° C. was treated with 4,7-dichlorocinnoline (2.2 g) and ethanol (10 ml) was added. The resultant green suspension was stirred vigorously overnight at 70° C. The mixture was cooled, and the solid was filtered, washed with water and dried at room tempera... | O=S(=O)(O)c1ccc(Nc2cnnc3cc(Cl)ccc23)cc1 | null | 93 | null |
1,322,675 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:7]=[C:6](I)[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.[NH3:13].CO>>[Cl:1][C:2]1[CH:7]=[C:6]([NH2:13])[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1 | FC(F)(F)c1cnc(Cl)cc1I | N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 130 | null | 2-chloro-4-iodo-5-(trifluoromethyl)pyridine was dissolved in 7 M Ammonia/Methanol. It was heated in a Biotage Initiator microwave synthesizer at 130° C. for 1 h. A mixture of the 2- and 4-substituted products was obtained. The solvent was removed and the residue was purified by silica gel chromatography (DCM/MeOH) grad... | Nc1cc(Cl)ncc1C(F)(F)F | null | null | null |
162,617 | ord_dataset-f5dc3e448c204058b116bf1970695bef | null | 1987-01-01T00:09:00 | true | [CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH:14]([CH3:31])[C:15]([C:17]2[CH:22]=[CH:21][C:20]([O:23]CC3C=CC=CC=3)=[CH:19][CH:18]=2)=[O:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.C(O)(=O)C.[Pd]>[CH2:1]([CH:8]1[CH2:9][CH2:10][N:11]([CH:14]([CH3:31])[C:15]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19... | CC(C(=O)c1ccc(OCc2ccccc2)cc1)N1CCC(Cc2ccccc2)CC1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | 25 g of 2-(4-benzylpiperidino)-4'-benzyloxypropiophenone are debenzylated in 200 ml of ethanol and 10 ml of acetic acid, in a Parr apparatus, in the presence of 1 g of 10% palladium-on-charcoal under a pressure of 0.1 MPa for 3 hours. The product obtained is isolated by filtering off the catalyst and evaporating off th... | CC(C(=O)c1ccc(O)cc1)N1CCC(Cc2ccccc2)CC1 | null | null | null |
54,727 | ord_dataset-159c363342e44b539e7a5975c873e30d | null | 1979-01-01T00:05:00 | true | [CH3:1][C:2]1[O:6][C:5]([NH:7][CH2:8][CH2:9][CH3:10])=[N:4][N:3]=1.[CH:11]1([C:15](Cl)=[O:16])[CH2:14][CH2:13][CH2:12]1.C(N(CC)CC)C>C1C=CC=CC=1>[CH3:1][C:2]1[O:6][C:5]([N:7]([CH2:8][CH2:9][CH3:10])[C:15]([CH:11]2[CH2:14][CH2:13][CH2:12]2)=[O:16])=[N:4][N:3]=1 | O=C(Cl)C1CCC1 | CCCNc1nnc(C)o1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccccc1 | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | 5-Methyl-2-n-propylamino 1,3,4-oxadiazole (6 g, 0.04 mol) prepared as in (b) above, was refluxed with cyclobutanecarboxylic acid chloride (5.5 g, 0.05 mol) in benzene (25 ml) in the presence of triethylamine (4.72 g, 0.05 mol) for 2 hours. The mixture was filtered and the filtrate washed with dilute HCl, saturated solu... | CCCN(C(=O)C1CCC1)c1nnc(C)o1 | null | null | null |
1,002,998 | ord_dataset-70899a0178cc441482746c093624afa0 | null | 2010-01-01T00:10:00 | true | Br[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][CH2:14][N:15]3[CH2:19][CH2:18][CH2:17][C:16]3=[O:20])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[CH:21](/B(O)O)=[CH:22]\[CH2:23][CH2:24][CH2:25][CH3:26].[ClH:30]>CCOCC>[ClH:30].[CH:21](/[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][CH2:14][N:15]3[CH2:19][CH2:18][CH2:17][C:16]... | CCCC/C=C/B(O)O | O=C1CCCN1CCCNc1ccc2ncc(Br)n2n1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | null | null | Prepared from the product of step A and (E)-1-hexeneboronic acid according to general procedure 2. The free-base was converted to the HCl salt with 2N HCl in Et2O to provide the title compound (68 mg, 52%) as a brown solid; 1H NMR (500 MHz, CD3OD) δ 7.90 (s, 1H), 7.86 (d, J=9.8 Hz, 1H), 7.16 (d, J=9.8 Hz, 1H), 6.89 (dt... | CCCC/C=C/c1cnc2ccc(NCCCN3CCCC3=O)nn12 | null | 52 | null |
953,410 | ord_dataset-3feb2a95f66e4706a4a50c977ccd9bf8 | null | 2010-01-01T00:04:00 | true | [CH2:1]([N:3]([CH2:7][CH3:8])[C:4](Cl)=[O:5])[CH3:2].[Cl:9][C:10]1[C:11]([O:20][C:21]2[CH:25]=[C:24]([CH3:26])[NH:23][N:22]=2)=[N:12][CH:13]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:15]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C=O)C>[CH2:1]([N:3]([CH2:7][CH3:8])[C:4]([N:23]1[C:24]([CH3:26])=[CH:25][C:21]([O:20][C:11]2[C:10]([C... | Cc1cc(Oc2ncc(C(F)(F)F)cc2Cl)n[nH]1 | CCN(CC)C(=O)Cl | null | Cl | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 70 | 9 | Diethylcarbamoyl chloride (1.52 g, 7.8 mmol) was added to a solution of 3-(3-chloro-5-trifluoromethylpyridin-2-yloxy)-5-methylpyrazole (1.39 g, 5.0 mmol) and potassium carbonate (1.98 g, 14.3 mmol) in DMF (15 ml), the mixture was stirred at 70° C. for 9 hours and further stirred at room temperature for 2 days. After co... | CCN(CC)C(=O)n1nc(Oc2ncc(C(F)(F)F)cc2Cl)cc1C | null | 11.1 | null |
1,753,632 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [CH:1]([C:4]1[CH:16]=[CH:15][C:7]([C:8]([O:10]C(C)(C)C)=[O:9])=[CH:6][C:5]=1[O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH3:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[CH:1]([C:4]1[CH:16]=[CH:15][C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]=1[O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH3:3])[CH3:2] | CC(C)c1ccc(C(=O)OC(C)(C)C)cc1Oc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | To a solution of tert-butyl 4-isopropyl-3-phenoxybenzoate (150 mg, 0.48 mmol) in dichloromethane (10 mL) was added 2,2,2-trifluoroacetic acid (2 mL). The resultant mixture was stirred at room temperature for 30 minutes. Thin layer chromatography showed that starting material was consumed completely. The solution was co... | CC(C)c1ccc(C(=O)O)cc1Oc1ccccc1 | null | 81.3 | null |
1,269,111 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [Cl:1][C:2]1[C:3]([NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[S:36]([CH:39]([CH3:41])[CH3:40])(=[O:38])=[O:37])=[N:4][C:5]([NH:8][C:9]2[CH:17]=[C:16]3[C:12]([CH2:13][N:14]([CH:19]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)[C:15]3=[O:18])=[CH:11][C:10]=2[O:25][CH:26]([CH3:28])[CH3:27])=[N:6][CH:7]=1.C(N(CC)CC)C.... | CN(C)C(=O)Cl | CC(C)Oc1cc2c(cc1Nc1ncc(Cl)c(Nc3ccccc3S(=O)(=O)C(C)C)n1)C(=O)N(C1CCNCC1)C2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 1 | To a mixture of 6-{5-Chloro-4-[2-(propane-2-sulfonyl)-phenylamino]-pyrimidin-2-ylamino}-5-isopropoxy-2-piperidin-4-yl-2,3-dihydro-isoindol-1-one (Example 1, 20 mg, 0.033 mmol) and triethylamine (23 uL, 0.165 mmol) in DMF (1.5 mL) is added dimethylcarbamyl chloride (11 mg, 0.1 mmol). The mixture is stirred at room tempe... | CC(C)Oc1cc2c(cc1Nc1ncc(Cl)c(Nc3ccccc3S(=O)(=O)C(C)C)n1)C(=O)N(C1CCN(C(=O)N(C)C)CC1)C2 | null | null | null |
1,450,848 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | Cl.[NH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][N:5]([CH3:9])[C:4]1=[O:10].C(N(CC)CC)C.S=[C:19]1[CH2:23][S:22][C:21](=[O:24])[NH:20]1>C(O)C>[CH3:9][N:5]1[CH2:6][CH2:7][CH2:8][CH:3]([NH:2][C:19]2[CH2:23][S:22][C:21](=[O:24])[N:20]=2)[C:4]1=[O:10] | O=C1NC(=S)CS1 | CN1CCCC(N)C1=O | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 25 | 8 | To a solution of the crude product containing 3-amino-1-methylpiperidin-2-one hydrochloride obtained in C) and triethylamine (3 mL) in ethanol (15 mL) was added 4-thioxothiazolidin-2-one (666 mg) at room temperature. The reaction mixture was stirred at room temperature overnight, and the solvent was evaporated under re... | CN1CCCC(NC2=NC(=O)SC2)C1=O | null | null | null |
1,201,406 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | [Br:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=O)[C:5]([OH:11])=[CH:4][CH:3]=1.[Cl:12][C:13]1[CH:14]=[C:15]([CH:17]=[C:18]([Cl:21])[C:19]=1[OH:20])[NH2:16]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([NH:16][C:15]1[CH:14]=[C:13]([Cl:12])[C:19]([OH:20])=[C:18]([Cl:21])[CH:17]=1)=[O:9] | Nc1cc(Cl)c(O)c(Cl)c1 | O=C(O)c1cc(Br)ccc1O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Using 5-bromosalicylic acid and 3,5-dichloro-4-hydroxyaniline as the raw materials, the same operation as the example 16 gave the title compound. 22.5%). | O=C(Nc1cc(Cl)c(O)c(Cl)c1)c1cc(Br)ccc1O | null | null | null |
618,636 | ord_dataset-2952e63264f5422a84e12cca1e0541ee | null | 2003-01-01T00:12:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-])=O)[C:3]=1[OH:11].Cl.CCCCCCC>C(O)C.[Fe]>[NH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[OH:11] | O=[N+]([O-])c1cccc(Cl)c1O | null | null | [Fe] | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCCCCC | CCO | null | null | null | null | null | null | null | null | null | 25 | null | A solution of 2-chloro-6-nitrophenol (1.210 g, 6.972 mmol) in ethanol (50 mL) was treated with iron powder (1.947 g, 34.86 mmol) and concentrated HCl (3 mL). The yellow mixture was heated to reflux for 18 h and then cooled to room temperature. The reaction mixture was filtered through a pad of Celite, and the filtrate ... | Nc1cccc(Cl)c1O | null | 57.6 | null |
102,353 | ord_dataset-72d9f7ef86df410fac4765c9632d459b | null | 1983-01-01T00:01:00 | true | [N+:1]([C:4]1[CH:22]=[CH:21][CH:20]=[CH:19][C:5]=1[CH:6]=[C:7]([C:12]([CH:14]([O:17][CH3:18])[O:15][CH3:16])=O)[C:8]([O:10][CH3:11])=[O:9])([O-:3])=[O:2].[NH2:23]/[C:24](/[CH3:30])=[CH:25]\[C:26]([O:28][CH3:29])=[O:27]>>[CH3:30][C:24]1[NH:23][C:12]([CH:14]([O:17][CH3:18])[O:15][CH3:16])=[C:7]([C:8]([O:10][CH3:11])=[O:9... | COC(=O)C(=Cc1ccccc1[N+](=O)[O-])C(=O)C(OC)OC | COC(=O)/C=C(/C)N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of methyl 2-(2-nitrobenzylidene)-4,4-dimethoxyacetoacetate (15.19 g) and methyl 3-aminocrotonate (6.50 g) was heated at 60° to 63° C. for 6 hours and at 100° to 105° C. for 4 hours and 45 minutes. The resulting crystalline mass was triturated with methanol and collected by filtration to give crystals of dimet... | COC(=O)C1=C(C)NC(C(OC)OC)=C(C(=O)OC)C1c1ccccc1[N+](=O)[O-] | null | 60.3 | null |
1,654,427 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [O:1]1[CH2:6][CH2:5][CH:4]([NH2:7])[CH2:3][CH2:2]1.[N-:8]=[C:9]=[O:10].[K+].[Na+].[Cl-]>O>[O:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:9]([NH2:8])=[O:10])[CH2:3][CH2:2]1 | [N-]=C=O | NC1CCOCC1 | null | [Cl-] | [K+] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 25 | null | A mixture of tetrahydro-2H-pyran-4-amine (5.0 g, 49.4 mmol, 1.0 equiv.) and potassium isocyanate (4.0 g, 49.5 mmol, 1.0 equiv.) was refluxed in H2O (50 mL) overnight. The reaction was cooled to room temperature and excess NaCl was added to help saturate the aqueous layer. The precipitate was isolated by filtration to p... | NC(=O)NC1CCOCC1 | null | 18 | null |
1,016,276 | ord_dataset-f024e9664ab64906a71a2ff6004cb3d0 | null | 2010-01-01T00:12:00 | true | [CH:1]1([N:7]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[C:8]([NH:10][C:11]2[S:12][C:13]([CH:16]=O)=[CH:14][N:15]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[CH2:25]([S:27]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)(=[O:29])=[O:28])[CH3:26].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[CH:1]1([N:7]([CH:18]... | O=Cc1cnc(NC(=O)N(C2CCCCC2)C2CCCCC2)s1 | CCS(=O)(=O)N1CCNCC1 | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | Cl | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared as described in general procedure (P) using 1,1-dicyclohexyl-3-(5-formyl-thiazol-2-yl)-urea (100 mg, 0.30 mmol), ethanesulfonyl-piperazine hydrochloride (128 mg, 0.60 mmol) and sodium triacetoxyborohydride (83 mg, 0.39 mmol) to afford 66 mg (44%) of the desired product after purification. | CCS(=O)(=O)N1CCN(Cc2cnc(NC(=O)N(C3CCCCC3)C3CCCCC3)s2)CC1 | null | 44.2 | null |
322,197 | ord_dataset-eed8d32c2f1d46a89ba39d04dfaa83b1 | null | 1995-01-01T00:12:00 | true | [NH2:1][CH:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:7][C:6]=1[O:15][CH2:16][CH3:17])[CH2:3][OH:4].C(N(CC)CC)C.[F:25][C:26]1[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[C:27]=1[C:28](Cl)=[O:29]>O1CCCC1>[F:25][C:26]1[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[C:27]=1[C:28]([NH:1][CH:2]([C:5]1[CH:10]=[CH:9]... | CCOc1cc(C(C)(C)C)ccc1C(N)CO | O=C(Cl)c1c(F)cccc1F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | A mixture of 23.6 g (0.10 mole) of 2-amino-2-(2-ethoxy-4-tert-butylphenyl)ethanol, 12.2 g (0.12 moles) of triethylamine and 200 ml of tetrahydrofuran was cooled and stirred, 17.7 g (0.10 mole) of 2,6-difluorobenzoyl chloride was added dropwise, and the mixture was stirred at room temperature for 5 hours. The reaction s... | CCOc1cc(C(C)(C)C)ccc1C(CO)NC(=O)c1c(F)cccc1F | null | 86.1 | null |
268,186 | ord_dataset-134cf2fa32ab464880d75db06c38f35a | null | 1993-01-01T00:05:00 | true | [F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]([CH2:14][CH2:15][N:16]([CH3:23])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][NH2:22])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[C:26]([NH:28][C:29](=[N:37][CH2:38][CH2:39][S:40][CH2:41][C:42]1[N:43]=[C:44]([NH:47][C:48]([NH2:50])=[NH:49])[S:45][CH:46]=1)OC1C=CC... | N#CNC(=NCCSCc1csc(NC(=N)N)n1)Oc1ccccc1 | CN(CCCCCN)CCN(Cc1ccc(F)cc1)c1ccccn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Preparation is effected analogously to Example 1, using 0.51 g (1.5 mmol) of N-[2-[N-(4-fluorobenzyl)-N-(2-pyridyl)amino]ethyl]-N-methyl-1,5-pentanediamine and the equimolar amount of N-cyano-N'-[2-[[(2-guanidino-4-thiazolyl)methyl]thio]ethyl]-O-phenyl-isourea as starting materials. Working up by chromatography analogo... | CN(CCCCCNC(=NCCSCc1csc(NC(=N)N)n1)NC#N)CCN(Cc1ccc(F)cc1)c1ccccn1 | null | null | null |
1,453,062 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [NH2:1][C:2]1[N:7]([C:8]2[C:13]([F:14])=[CH:12][C:11]([CH2:15][CH:16]=O)=[CH:10][C:9]=2[F:18])[C:6](=[O:19])[CH:5]=[CH:4][C:3]=1[C:20](=[O:29])[C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=1[F:28].Cl.[CH3:31][C:32]([C:35]([O:37][CH:38]1[CH2:42][CH2:41][CH2:40][CH2:39]1)=[O:36])([CH3:34])[NH2:33]>>[NH2:1][C:2]1[N:7... | CC(C)(N)C(=O)OC1CCCC1 | Nc1c(C(=O)c2ccc(F)cc2F)ccc(=O)n1-c1c(F)cc(CC=O)cc1F | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Example 2 was synthesised using Intermediate 4 and Intermediate 7 in a similar manner to Example 1. | CC(C)(NCCc1cc(F)c(-n2c(N)c(C(=O)c3ccc(F)cc3F)ccc2=O)c(F)c1)C(=O)OC1CCCC1 | null | null | null |
383,638 | ord_dataset-f367d8d2baac490b9204609a79420961 | null | 1997-01-01T00:11:00 | true | [H-].[Na+].[F:3][C:4]([F:13])([F:12])[C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1.[C:14]([C:16]1[CH:21]=[C:20](Cl)[N:19]=[C:18](Cl)[CH:17]=1)#[N:15]>CN1CCCC1=O>[C:14]([C:16]1[CH:21]=[C:20]([O:11][C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([C:4]([F:12])([F:13])[F:3])[CH:6]=2)[N:19]=[C:18]([O:11][C:7]2[CH:8]=[CH:9][CH:10]=[C:5... | Oc1cccc(C(F)(F)F)c1 | N#Cc1cc(Cl)nc(Cl)c1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN1CCCC1=O | null | null | null | null | null | null | null | null | null | null | 25 | null | Sodium hydride (0.31 g (ca. 60% in mineral oil), 0.0035×2.2 mol) was suspended in 20 ml of N-methyl-2-pyrrolidinone, then meta-trifluoromethyl phenol (1.24 g, 0.0035×2.2 mol) was added thereto, and the resultant solution was heated to about 60° C. and stirred for several minutes. After allowed to cool to room temperatu... | N#Cc1cc(Oc2cccc(C(F)(F)F)c2)nc(Oc2cccc(C(F)(F)F)c2)c1 | null | null | null |
145,595 | ord_dataset-4731a430f0af464b83e8b5b145cd2c77 | null | 1986-01-01T00:07:00 | true | [C:1]1([S:7]([CH2:10][CH2:11][NH:12][CH:13]([CH3:15])[CH3:14])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:16]([N:18]([CH2:21][CH2:22][CH2:23][N:24]=[C:25]=[S:26])[CH2:19][CH3:20])[CH3:17]>C(#N)C>[CH2:19]([N:18]([CH2:16][CH3:17])[CH2:21][CH2:22][CH2:23][NH:24][C:25](=[S:26])[N:12]([CH:13]([CH3:15])[CH3:14])[C... | CCN(CC)CCCN=C=S | CC(C)NCCS(=O)(=O)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 5.0 g (0.022 mole) of N-[2-(phenylsulfonyl)ethyl]-2-propanamine and 4.30 g (0.025 mole) of 3-(N,N-diethylamino)propylisothiocyanate in 400 ml of acetonitrile was refluxed for 16 hr. The solvent was removed in vacuo and the residue was dissolved in ether. The solution was extracted with three portions of w... | CCN(CC)CCCNC(=S)N(CCS(=O)(=O)c1ccccc1)C(C)C | null | 76.9 | null |
1,053,058 | ord_dataset-373415d3e0e54004837cf4831e67666f | null | 2011-01-01T00:05:00 | true | [H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1[NH:13][C:14](=[O:16])[CH3:15].Cl[CH2:18][C:19]([CH3:21])=[CH2:20]>CN(C)C=O.O>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1[N:13]([CH2:20][C:19]([CH3:21])=[CH2:18])[C:14](=[O:16])[CH3:15] | C=C(C)CCl | CC(=O)Nc1cc([N+](=O)[O-])ccc1Br | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O | null | null | null | null | null | null | null | null | null | 60 | null | To a suspension of 1.34 g of sodium hydride in 10 mL of dimethylformamide under argon is added dropwise, at 0° C., a solution of 5.8 g of N-(2-bromo-5-nitrophenyl)acetamide obtained in stage c) below in 90 mL of dimethylformamide and the reaction medium is stirred at this temperature for 1 hour. 3.3 mL of 3-chloro-2-me... | C=C(C)CN(C(C)=O)c1cc([N+](=O)[O-])ccc1Br | null | null | null |
1,059,058 | ord_dataset-373415d3e0e54004837cf4831e67666f | null | 2011-01-01T00:05:00 | true | [NH2:1][C@H:2]1[C:15](=[O:16])[N:14]([CH2:17][CH2:18][N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[CH2:13][C:5]2[C:6]3[CH:7]=[N:8][NH:9][C:10]=3[CH:11]=[CH:12][C:4]=2[CH2:3]1.[O:24]=[C:25]1[NH:33][C:28]2=[N:29][CH:30]=[CH:31][CH:32]=[C:27]2[C:26]21[CH2:41][C:40]1[C:35](=[CH:36][CH:37]=[C:38]([C:42](O)=[O:43])[CH:39]=1)[CH2... | O=C(O)c1ccc2c(c1)CC1(C2)C(=O)Nc2ncccc21 | N[C@@H]1Cc2ccc3[nH]ncc3c2CN(CCN2CCCC2)C1=O | null | On1nnc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | ClCCCl | null | null | null | null | null | null | null | null | null | 25 | 18 | A mixture of 7-(R)-amino-9-(2-pyrrolidin-1-yl-ethyl)-6,7,9,10-tetrahydro-3H-2,3,9-triazacyclohepta[e]inden-8-one (72 mg, 0.23 mmol) [Chaturvedula et al. WO 2006/052378], (±)-2′-oxo-1,1′,2′,3-tetrahydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridine]-5-carboxylic acid (78 mg, 0.28 mmol) [Bell et al. WO 2006/031606], HOBT (43 m... | O=C(N[C@@H]1Cc2ccc3[nH]ncc3c2CN(CCN2CCCC2)C1=O)c1ccc2c(c1)CC1(C2)C(=O)Nc2ncccc21 | null | null | null |
1,745,212 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | Br[C:2]1[N:3]=[C:4]([N:7]2[CH:12]3[CH2:13][CH2:14][CH:8]2[CH2:9][O:10][CH2:11]3)[S:5][CH:6]=1.C(O)C.[Cl:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C... | Brc1csc(N2C3CCC2COC3)n1 | OB(O)c1ccc(Cl)cc1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | 92.5 | null | To a solution of 8-(4-bromothiazol-2-yl)-3-oxa-8-azabicyclo[3.2.1]octane (Step-1 of o compound 56, 0.29 g, 1.05 mmol) in a mixture of toluene:ethanol (1.5 ml:4.5 ml) were added (4-chlorophenyl) boronic acid (0.18 g, 1.16 mmol) and potassium carbonate (0.29 g, 2.11 mmol) at 25° C. in a tube, the nitrogen gas was bubbled... | Clc1ccc(-c2csc(N3C4CCC3COC4)n2)cc1 | null | 86.9 | null |
981,783 | ord_dataset-35b56288528641309a040cc2b6710b61 | null | 2010-01-01T00:08:00 | true | [F:1][C:2]1[CH:27]=[C:26]([N+:28]([O-])=O)[CH:25]=[CH:24][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=3)[S:13][C:6]=12.[BH4-].[Na+]>C1COCC1.CO.Cl[Ni]Cl>[F:1][C:2]1[CH:27]=[C:26]([NH2:28])[CH:25]=[CH:24][C:3]=1[O:4][C:5]1[CH:10]=... | CS(=O)(=O)c1ccc(-c2cc3nccc(Oc4ccc([N+](=O)[O-])cc4F)c3s2)cc1 | null | null | Cl[Ni]Cl | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CO | null | null | null | null | null | null | null | null | null | 0 | 0.33 | Nitro compound 48 (97 mg, 2 mmol) was dissolved in a mixture of THF (7 mL) and MeOH (15 mL); NiCl2.×6H2O (130 mg, 0.5 mmol) was added and the solution was cooled to 0° C. To the cooled mixture NaBH4 (42 mg, 1.1 mmol) was added portion wise. The reaction was stirred for 20 min and quenched with 2 M HCl. The solvents wer... | CS(=O)(=O)c1ccc(-c2cc3nccc(Oc4ccc(N)cc4F)c3s2)cc1 | null | 5.6 | null |
1,308,131 | ord_dataset-78c3f723155a4347a902b53bcee1524d | null | 2013-01-01T00:06:00 | true | [CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][C:12]=2[Cl:14])[NH:7][C:6]=1[CH3:15].[H-].[Na+].[CH3:19][S:20]([C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Br)=[CH:25][CH:24]=1)(=[O:22])=[O:21]>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][C:12]=2[Cl:14])[N:7]([C... | COC(=O)Cc1c(C)[nH]c2nccc(Cl)c12 | CS(=O)(=O)c1ccc(CBr)cc1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O | null | null | null | null | null | null | null | null | null | 0 | 5 | To a cooled (0° C.) stirred solution of (4-chloro-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-acetic acid methyl ester (0.1 g, 0.42 mmol) in dry DMF (2.5 ml) is added sodium hydride (0.019 g of a 60% dispersion in mineral oil, 0.47 mmol). After stirring at room temperature for 5 hours, the reaction mixture is re-cooled to ... | COC(=O)Cc1c(C)n(Cc2ccc(S(C)(=O)=O)cc2)c2nccc(Cl)c12 | null | null | null |
1,338,909 | ord_dataset-08852243bba44cb28769a5833f1515fe | null | 2013-01-01T00:09:00 | true | [CH3:1][C:2]1([C:7]2[O:11][C:10]([CH2:12][N:13]3[N:17]=[C:16]([NH2:18])[CH:15]=[N:14]3)=[CH:9][CH:8]=2)[O:6]CCO1.[C:19]1([CH3:34])[CH:24]=[CH:23][CH:22]=[C:21]([C:25]2[O:29][C:28]([CH3:30])=[N:27][C:26]=2[C:31](O)=[O:32])[CH:20]=1>>[C:2]([C:7]1[O:11][C:10]([CH2:12][N:13]2[N:17]=[C:16]([NH:18][C:31]([C:26]3[N:27]=[C:28]... | CC1(c2ccc(Cn3ncc(N)n3)o2)OCCO1 | Cc1cccc(-c2oc(C)nc2C(=O)O)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Following general procedure A followed by L, starting from 2-[5-(2-methyl-[1,3]dioxolan-2-yl)-furan-2-ylmethyl]-2H-[1,2,3]triazol-4-ylamine and 5-(m-tolyl)-2-methyl-oxazole-4-carboxylic acid. | CC(=O)c1ccc(Cn2ncc(NC(=O)c3nc(C)oc3-c3cccc(C)c3)n2)o1 | null | null | null |
788,251 | ord_dataset-4ad5db8537994579bef51f16dd8bf0bd | null | 2007-01-01T00:08:00 | true | [N+:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10][CH2:11][C:12]2[N:13]([CH2:17][CH2:18][CH3:19])[CH:14]=[CH:15][N:16]=2)=[N:8][CH:9]=1)([O-])=O.[Cl-].[Ca+2].[Cl-]>C(O)C>[CH2:17]([N:13]1[CH:14]=[CH:15][N:16]=[C:12]1[CH2:11][S:10][C:7]1[N:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=1)[CH2:18][CH3:19] | CCCn1ccnc1CSc1ccc([N+](=O)[O-])cn1 | null | null | [Ca+2] | [Cl-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 25 | null | 5-nitro-2-[[(1-propylimidazol-2-yl)methyl]sulfanyl]pyridine (4.8 g) was dissolved in 85% ethanol solution (114 ml), calcium chloride (0.95 g) and reduced iron (4.8 g) were added to the mixture, and the mixture was heated to reflux for 4 hours. After cooling to room temperature, the mixture was filtered with Celite, and... | CCCn1ccnc1CSc1ccc(N)cn1 | null | 65.4 | null |
583,434 | ord_dataset-60f3171f0342452f8814e7f294e2be8b | null | 2003-01-01T00:02:00 | true | [Mg].Br[C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].[Br-].[C:18]1(=[O:25])[O:24][C:22](=[O:23])[CH2:21][CH2:20][CH2:19]1>C1COCC1.CCOC(C)=O>[C:10]([Si:7]([CH3:9])([CH3:8])[O:6][C:5]1[CH:4]=[C:3]([C:18](=[O:25])[CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])[... | CC(C)(C)[Si](C)(C)Oc1cccc(Br)c1 | O=C1CCCC(=O)O1 | null | [Br-] | [Mg] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | 2 | Magnesium (0.226 g, 8.58 mmol) was flame dried in a 50 mL RB flask equipped with addition funnel and magnetic stirrer under N2. When the flask had cooled, anhydrous THF (25 mL), a pinch of iodine, and a THF solution of Rieke magnesium (1 mL) were added, followed by a small portion of 3-bromophenoxy-tert-butyl(dimethyl)... | CC(C)(C)[Si](C)(C)Oc1cccc(C(=O)CCCC(=O)O)c1 | null | null | null |
811,935 | ord_dataset-892acf7477db4d3a8a8559f004a7c0a2 | null | 2008-01-01T00:03:00 | true | Cl.CN(C)CCCN=C=NCC.[CH3:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=1.[Br:24][CH2:25][CH2:26][CH2:27]O>CN(C)C1C=CN=CC=1.ClCCl>[CH3:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([O:21][CH2:27][CH2:26][CH2:25][Br:24])=[O:20])=[CH:17][CH:16]=1 | COc1ccc(C(=O)O)cc1 | OCCCBr | null | CCN=C=NCCCN(C)C | CN(C)c1ccncc1 | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 16 | 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDAC) (3.4 g, 17.7 mmol) was slowly added to a solution of 4-methoxybenzoic acid (2.0 g, 13.1 mmol), 3-bromopropan-1-ol (1.1 mL, 12.6 mmol), and 4-(dimethylamino)pyridine (100 mg) in 80 mL of anhydrous dichloromethane. The mixture was stirred at room temperat... | COc1ccc(C(=O)OCCCBr)cc1 | null | 61 | null |
545,641 | ord_dataset-d31180f42ced44719fd9e72685c798bf | null | 2002-01-01T00:05:00 | true | [OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.C(OCC)(=O)C.[C:18]1([CH3:24])[CH:23]=CC=C[CH:19]=1>CCCCCC>[C:18]([O:10][C:9](=[O:11])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1)([CH3:24])([CH3:23])[CH3:19] | O=C(O)Cc1ccc(O)cc1 | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCCCC | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 80 | 0.5 | A stirred suspension of 4-hydroxy-phenyl acetic acid (0.152 g, 1 mmol) in anhydrous toluene (5 mL) was heated at 80° C. and N,N-dimethyl formamide-di-ti-butyl acetal (1 mL, 4.17mmol) was added when the solution became homogenous. After 0.5 h, the reaction mixture was cooled to ambient temperature and the volatiles were... | CC(C)(C)OC(=O)Cc1ccc(O)cc1 | null | 56 | null |
1,055,088 | ord_dataset-373415d3e0e54004837cf4831e67666f | null | 2011-01-01T00:05:00 | true | [CH2:1]([CH2:5][C:6](=O)[CH3:7])[C:2]([CH3:4])=O.[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][C:17]#[N:18].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:4][C:2]1[N:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:16][C:17]#[N:18])[C:6]([CH3:7])=[CH:5][CH:1]=1 | CC(=O)CCC(C)=O | N#CCc1ccccc1N | null | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | 155 | 8 | p-Toluenesulfonic acid (2 mg, 0.16 mmol) and acetonylacetone (2.14 g, 18.7 mmol) were added sequentially to a solution of 2-aminophenylacetonitrile (2.06 g, 15.6 mmol) in toluene (30 mL). The reaction mixture was heated in an oil bath at 155° C. for 1 hour and then allowed to stand at ambient temperature overnight. Ace... | Cc1ccc(C)n1-c1ccccc1CC#N | null | 102.1 | null |
922,211 | ord_dataset-8e59bd24817446f7b1c68e805b8e5f1d | null | 2009-01-01T00:11:00 | true | [F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:17](=[O:18])[C:16]2[C@H:15]3[C:19]([CH3:21])([CH3:20])[C@:12]([CH3:22])([CH2:13][CH2:14]3)[C:11]=2[NH:10]1.[I-].[Na+].[F:25][C:26]1[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:27]=1[CH2:28]Br.C(OCC)(=O)C>CN(C)C=O>[F:25][C:26]1[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:... | CC1(C)[C@H]2CC[C@]1(C)c1[nH]n(-c3ccc(F)cc3F)c(=O)c12 | Fc1ccc(CBr)c(F)c1 | null | [I-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | A solution of (4R,7S)-2-(2,4-difluoro-phenyl)-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 42; 101 mg, 0.33 mmol), sodium iodide (53 mg, 0.35 mmol) and 2,4-difluorobenzyl bromide (0.22 mL, 1.68 mmol) in dimethylformamide (0.8 mL) was heated under microwave irradiation at 150° C. for 1 h... | CC1(C)[C@H]2CC[C@]1(C)c1c2c(=O)n(-c2ccc(F)cc2F)n1Cc1ccc(F)cc1F | null | 57.7 | null |
983,169 | ord_dataset-35b56288528641309a040cc2b6710b61 | null | 2010-01-01T00:08:00 | true | [C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9](OC)[CH:10]=2)[N:5]([CH2:14][CH3:15])[C:4]=1[C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22]C)=[O:21])=[CH:18][CH:17]=1)#[N:2].[OH-].[Na+].C1C[O:31][CH2:30]C1>O>[C:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([O:31][CH3:30])=[CH:9][CH:10]=2)[N:5]([CH2:14][CH3:15])[C:4]=1[C:16]1[CH:17]=[CH:18... | CCn1c(-c2ccc(C(=O)OC)cc2)c(C#N)c2cc(OC)ccc21 | C1CCOC1 | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 80 | null | Methyl 4-(3-cyano-1-ethyl-5-methoxy-1H-indol-2-yl)-benzoate (350 mg, 1.05 mmol), prepared as described in Example 1Ga step B, is combined with NaOH (40 mg, 1 mmol), H2O (0.8 mL), and THF (3.4 mL) and is heated at 80° C. for 1 hour. The reaction mixture is diluted in H2O and is then ether-washed. The aqueous layer is ac... | CCn1c(-c2ccc(C(=O)O)cc2)c(C#N)c2ccc(OC)cc21 | null | 92 | null |
28,814 | ord_dataset-2cb52357eb5f43c2be56ad5c0662f18f | null | 1977-01-01T00:08:00 | true | [Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[N:11][N:10]=[C:9]2[CH2:13]Cl)=[C:4]([C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=[O:16])[CH:3]=1.[CH3:23][NH:24][CH3:25]>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[N:11][N:10]=[C:9]2[CH2:13][N:24]([CH3:25])[CH3:23])=[C:4]([C:15]([C:17]2[CH:22]=[CH:21][CH:2... | CNC | O=C(c1ccccn1)c1cc(Br)ccc1-n1cnnc1CCl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 0.25 g of 4-[4-bromo-2-(2-pyridinecarbonyl)phenyl]-3-chloromethyl-4H-1,2,4-triazole, 10 ml. of ethanol and 0.5 ml. of dimethylamine is refluxed for 1.5 hours. After evaporation of the solvent, the residue is diluted with water and then extracted with chloroform. The chloroform layer is washed with water, d... | CN(C)Cc1nncn1-c1ccc(Br)cc1C(=O)c1ccccn1 | null | null | null |
1,062,407 | ord_dataset-ffbef48837674f39816de887b5dc8bae | null | 2011-01-01T00:06:00 | true | [Cl:1]N1C(=O)CCC1=O.[CH3:9][CH:10]1[C:16]2=[C:17]3[C:21](=[CH:22][CH:23]=[C:15]2[O:14][CH2:13][CH2:12][N:11]1[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[NH:20][CH:19]=[CH:18]3>C1COCC1>[Cl:1][C:18]1[C:17]2[C:21](=[CH:22][CH:23]=[C:15]3[O:14][CH2:13][CH2:12][N:11]([C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:... | CC1c2c(ccc3[nH]ccc23)OCCN1C(=O)OC(C)(C)C | O=C1CCC(=O)N1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 8 | N-chlorosuccinimide (13 mg, 0.10 mmol) was added to a solution of tert-butyl 1-methyl-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole-2-carboxylate (Intermediate 42, 0.030 g, 0.099 mmol) in THF (2 mL) and the reaction mixture was stirred at room temperature overnight. The solvent was evaporated and the crude material... | CC1c2c(ccc3[nH]cc(Cl)c23)OCCN1C(=O)OC(C)(C)C | null | 52.5 | null |
324,780 | ord_dataset-fc4cd2699fc04ecbb7c7c831849e6b22 | null | 1996-01-01T00:02:00 | true | [CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[NH:13][S:14]([CH2:17][C:18]([NH:20][C:21]1N=NN(CCCCCCCCCCCC)N=1)=[O:19])(=[O:16])=[O:15])([CH3:3])[CH3:2].[CH2:38](N)[CH2:39][CH2:40][CH2:41][CH2:42]C>>[CH:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH:1]([CH3:2])[CH3:3])[C:5]=1[NH:13][S:14]([CH2:17][C:... | CCCCCCN | CCCCCCCCCCCCn1nnc(NC(=O)CS(=O)(=O)Nc2c(C(C)C)cccc2C(C)C)n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | This compound was prepared in the same manner as for the title compound of Example 2, except that 2-DAT was replaced with N-hexylamine, mp 125°-127° C. | CCCCCCNC(=O)CS(=O)(=O)Nc1c(C(C)C)cccc1C(C)C | null | null | null |
1,769,633 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | C1(N[C:7]2[C:12]([CH3:13])=[C:11]([CH3:14])[N:10]=[C:9]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[N:8]=2)CCCC1.[NH2:23][C:24]1[C:25]([CH3:30])=[CH:26][CH:27]=[CH:28][CH:29]=1>>[CH3:13][C:12]1[C:7]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])=[N:8][C:9]([NH:15][CH2:16][C:17]2[CH:22]=... | Cc1nc(NCc2ccccn2)nc(NC2CCCC2)c1C | Cc1ccccc1N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The titled compound was synthesized according to the procedure described for preparation of N4-cyclopentyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine (Example 29) using o-toluidine instead of cyclopentanamine. The crude material was purified by column chromatography eluting with mixture of chloroform/et... | Cc1ccccc1Nc1nc(NCc2ccccn2)nc(C)c1C | null | null | null |
613,258 | ord_dataset-5c4ee54447b84205a10f9c0473172972 | null | 2003-01-01T00:10:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]([N:12]1[CH2:17][CH2:16][C:15]2[S:18][CH:19]=[CH:20][C:14]=2[CH2:13]1)[C:9](N)=[O:10].OS(O)(=O)=O.[C:26](=O)([O-])[O-:27].[Na+].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]([N:12]1[CH2:17][CH2:16][C:15]2[S:18][CH:19]=[CH:20][C:14]=2[CH2:13]1)[C:9]([O:... | NC(=O)[C@H](c1ccccc1Cl)N1CCc2sccc2C1 | O=C([O-])[O-] | null | O=S(=O)(O)O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | -15 | 0.5 | 5 g of (S)-(+)-(2-chlorophenyl)-(6,7-dihydro-4H-thieno[3,2-c]pyrid-5-yl)acetamide was dissolved in 50 ml methanol and the solution was cooled till −15° C. 15 mL (0.28 mol) of conc. H2SO4 (98%) was added dropwise in 1 hr maintaining the temperature till −15° C. After the completion of addition the reaction mixture was g... | COC(=O)[C@H](c1ccccc1Cl)N1CCc2sccc2C1 | null | null | null |
193,834 | ord_dataset-b83b16f2fb1a4f8782f3d82c1766cc6b | null | 1989-01-01T00:08:00 | true | [CH3:1][C:2]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-])=O)([CH3:5])[CH2:3][OH:4].[CH2:16](O)[CH3:17]>[Pd]>[CH3:16][C:17]1[N:6]([C:2]([CH3:5])([CH3:1])[CH2:3][OH:4])[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:13]=1 | CCO | CC(C)(CO)Nc1ccccc1[N+](=O)[O-] | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 2-(1,1-dimethyl-2-hydroxyethyl)aminonitrobenzene (10 g) in ethanol (200 ml) was hydrogenated at 50 p.s.i. (345 kPa) over 5% Pd/C (0.5 g) for 2 hours. The catalyst was filtered off and the solvent removed under reduced pressure yielding the title compound as a yellow foam 8.4 g (98%). | Cc1nc2ccccc2n1C(C)(C)CO | null | 98 | null |
606,091 | ord_dataset-273fda773e864aaf9b71a30a2d9f2162 | null | 2003-01-01T00:08:00 | true | [CH3:1][C:2]1[C:6]([S:7](Cl)(=[O:9])=[O:8])=[C:5]([CH3:11])[O:4][N:3]=1.[CH2:12]([O:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[CH:26]([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH2:38][N:39]3[CH2:43][CH2:42][CH2:41][CH2:40]3)=[CH:32][CH:31]=1)[NH:25][CH2:24][CH2:23]2)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14... | c1ccc(COc2ccc3c(c2)CCNC3c2ccc(OCCN3CCCC3)cc2)cc1 | Cc1noc(C)c1S(=O)(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 21 | 3,5-Dimethylisoxazole-4-sulfonyl chloride (0.034 g, 0.18 mmol) was added to a solution of 6-benzyloxy-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-1,2,3,4-tetrahydroisoquinoline (0.075 g, 0.18 mmol) and Et3N (0.037 ml, 0.26 mmol) in anhydrous THF (10 ml) at rt under N2. The resulting suspension was stirred at rt for 21 hr, t... | Cc1noc(C)c1S(=O)(=O)N1CCc2cc(OCc3ccccc3)ccc2C1c1ccc(OCCN2CCCC2)cc1 | null | 104 | null |
966,843 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | C(=O)([O-])[O-].[K+].[K+].Cl[C:8]1[C:17]([Cl:18])=[N:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1.[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[S:26]([NH2:29])(=[O:28])=[O:27].Cl>O.CN(C)C=O>[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[S:26]([NH:29][C:8]1[C:17]([Cl:18])=[N:16][C:15]2[C:10](=[... | Clc1nc2ccccc2nc1Cl | NS(=O)(=O)c1ccccc1Cl | null | Cl | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O | null | null | null | null | null | null | null | null | null | null | null | In the presence of potassium carbonate (625 mg), 2,3-dichloroquinoxaline (275 mg) and 2-chlorobenzenesulfonamide (264 mg) were allowed to react in the solution of dimethylformamide (4 mL) for 3 hours at 90° C. To the reaction mixture, water and hydrochloric acid were added and extracted with ethyl acetate. The residue ... | O=S(=O)(Nc1nc2ccccc2nc1Cl)c1ccccc1Cl | null | 101 | null |
1,253,187 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [CH2:1]([N:3]([CH2:9][C:10]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:11]=1B1OC(C)(C)C(C)(C)O1)[C:4]([CH:6]1[CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH3:29][O:30][C:31](=[O:51])[CH2:32][C:33]1[CH:38]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:36]=[C:35](OS(C(F)(F)F)(=O)=O)[CH:34]=1>>[CH3:29][O:30][C:31](=[O:51]... | COC(=O)Cc1cc(OS(=O)(=O)C(F)(F)F)cc(C(F)(F)F)c1 | CCN(Cc1cc(C(F)(F)F)ccc1B1OC(C)(C)C(C)(C)O1)C(=O)C1CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared according to the procedure described in Example 1, Step 4, using the following starting materials: cyclopropanecarboxylic acid ethyl-[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-5-trifluoromethyl-benzyl]-amide and (3-trifluoromethanesulfonyloxy-5-trifluoromethyl-phenyl)-acetic acid methyl ester. | CCN(Cc1cc(C(F)(F)F)ccc1-c1cc(CC(=O)OC)cc(C(F)(F)F)c1)C(=O)C1CC1 | null | null | null |
808,234 | ord_dataset-da49b0378abf41bf92ab8ecdd3feb28b | null | 2008-01-01T00:02:00 | true | [NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][S:8]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([NH:21][C:22](=[O:29])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH2:3][CH2:2]1.CCN(CC)CC.[N:37]([CH:40]([CH3:42])[CH3:41])=[C:38]=[O:39]>C(Cl)Cl>[CH:40]([NH:37][C:38]([N:1]1[CH2:6... | O=C(Nc1ccc(S(=O)(=O)NC2CCNCC2)c2ccccc12)c1ccccc1 | CC(C)N=C=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 25 | 8 | To a 25° C. solution of N-[4-(piperidin-4-yl sulfamoyl)-naphthalen-1-yl]-benzamide (C-1) in CH2Cl2 was added Et3N followed by 2-isocyanato-propane. The reaction mixture was stirred at 25° C. overnight. Aqueous work-up followed by purification using reverse phase HPLC provided the title compound. 1H NMR (300 MHz, MeOD) ... | CC(C)NC(=O)N1CCC(NS(=O)(=O)c2ccc(NC(=O)c3ccccc3)c3ccccc23)CC1 | null | null | null |
1,630,413 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][C:26]([OH:28])=[O:27])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:29][C:30](=[CH2:32])[CH3:31].OS(O)(=O)=O>ClCCl>[C:30]([O:27][C:26](=[O:28])[CH2:25][O:24][CH2:23][CH2:22][O:21... | C=C(C)C | O=C(O)COCCOCCNC(=O)OCC1c2ccccc2-c2ccccc21 | null | O=S(=O)(O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 150 mg (0.389 mmol) of 8-(9-Fluorenylmethoxycarbonylamino)-3,6-dioxaoctanoic acid, 546 mg (9.73 mmol) isobutylene, and 4.3 μL of 95-98% H2SO4 was stirred at r.t. for 3 days. For workup the reaction solution was diluted with dichloromethane and washed with sat. bicarbonate solution. After drying over sodiu... | CC(C)(C)OC(=O)COCCOCCNC(=O)OCC1c2ccccc2-c2ccccc21 | null | 84.4 | null |
1,598,220 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.[N:18]([O-])=[O:19].[Na+]>Cl.C(O)C.O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]([C:11]2[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=2)[N:18]=[O:19])=[CH:4][CH:3]=1 | Cc1ccc(NCCc2ccc(Cl)nc2)cc1 | O=N[O-] | null | Cl | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCO | null | null | null | null | null | null | null | null | null | 25 | null | A 250 mL reaction flask was charged with N-(2-(6-chloropyridin-3-yl)ethyl)-4-methylaniline (5 g, 20.3 mmol; Example 117B) in 1 N HCl (22 mL) and ethanol (20 mL). The mixture was stirred at room temperature until complete dissolution was obtained (˜2 hours). The reaction then was cooled in an ice bath and a solution of ... | Cc1ccc(N(CCc2ccc(Cl)nc2)N=O)cc1 | null | null | null |
1,003,015 | ord_dataset-70899a0178cc441482746c093624afa0 | null | 2010-01-01T00:10:00 | true | [Br:1][C:2]1[N:6]2[N:7]=[C:8](Cl)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][NH2:19])[CH:13]=1.C(Cl)Cl.CO.[NH4+].[OH-]>>[Br:1][C:2]1[N:6]2[N:7]=[C:8]([NH:19][CH2:18][C:14]3[CH:13]=[N:12][CH:17]=[CH:16][CH:15]=3)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1 | Clc1ccc2ncc(Br)n2n1 | NCc1cccnc1 | null | [NH4+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | ClCCl | null | null | null | null | null | null | null | null | null | null | null | Prepared from 3-bromo-6-chloroimidazo[1,2-b]pyridazine and pyridin-3-ylmethanamine according to general procedure 1 providing the intermediate (88 mg, 45%) as a white solid: Rf=0.66 (CH2Cl2/MeOH/NH4OH, 160:18:2); 1H NMR (500 MHz, CD3OD) δ 8.70 (d, J=1.9 Hz, 1H), 7.99-7.97 (m, 1H), 7.85-7.82 (m, 1H), 7.59 (d, J=9.7 Hz, ... | Brc1cnc2ccc(NCc3cccnc3)nn12 | null | null | null |
1,075,361 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | [OH:1][C:2]1[C:19]([N+:20]([O-])=O)=[CH:18][C:5]2[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH2:10][C:4]=2[CH:3]=1>CCO.[Pd]>[NH2:20][C:19]1[C:2]([OH:1])=[CH:3][C:4]2[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:16])([CH3:17])[CH3:15])=[O:12])[CH2:7][CH2:6][C:5]=2[CH:18]=1 | CC(C)(C)OC(=O)N1CCc2cc(O)c([N+](=O)[O-])cc2CC1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | 1,1-Dimethylethyl 7-hydroxy-8-nitro-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (8.2 g) was hydrogenated for 4 h under atmospheric pressure and 25° C. in the presence of 10% Pd/C (1.4 g) in EtOH (200 ml). The catalyst was removed by filtration and volatiles evaporated to provide the title compound as a grey solid... | CC(C)(C)OC(=O)N1CCc2cc(N)c(O)cc2CC1 | null | 100 | null |
1,385,643 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | [Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]3([C@@H:15]([C:16]4[CH:21]=[CH:20][N:19]=[C:18]([Cl:22])[C:17]=4[F:23])[C@H:14]([C:24](O)=[O:25])[NH:13][C:12]43[CH2:31][CH2:30][C:29]([CH3:33])([CH3:32])[CH2:28][CH2:27]4)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.Cl.[NH2:35][C@H:36]1[CH2:41][CH2:40][C@H:39]([C:42]([N:44]([CH3:46])[CH3:... | CC1(C)CCC2(CC1)N[C@@H](C(=O)O)[C@H](c1ccnc(Cl)c1F)C21C(=O)Nc2cc(Cl)ccc21 | CN(C)C(=O)[C@H]1CC[C@H](N)CC1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The compound (29 mg, 0.06 mmol) obtained in Step 1 of Example 17 and trans-4-amino-N,N-dimethylcyclohexanecarboxamide hydrochloride (WO2008/068171) (17 mg, 0.08 mmol) were used as starting materials and treated in the same way as in Step 2 of Example 12 to give 36 mg (100%) of the title compound as a colorless solid. | CN(C)C(=O)[C@H]1CC[C@H](NC(=O)[C@@H]2NC3(CCC(C)(C)CC3)[C@@]3(C(=O)Nc4cc(Cl)ccc43)[C@H]2c2ccnc(Cl)c2F)CC1 | null | null | null |
681,105 | ord_dataset-3947f3e1be17462c8f7c7e6ea6e57d0a | null | 2005-01-01T00:08:00 | true | [Br:1][C:2]1[C:3]2[CH2:4][C@@H:5]3[CH2:14][NH:13][CH2:12][CH2:11][N:6]3[C:7]=2[CH:8]=[CH:9][CH:10]=1.Br[CH2:16][C:17]([NH2:19])=[O:18]>>[Br:1][C:2]1[C:3]2[CH2:4][C@@H:5]3[CH2:14][N:13]([CH2:16][C:17]([NH2:19])=[O:18])[CH2:12][CH2:11][N:6]3[C:7]=2[CH:8]=[CH:9][CH:10]=1 | Brc1cccc2c1C[C@@H]1CNCCN21 | NC(=O)CBr | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound, MS: m/e=310.1 (M+H+) was prepared in accordance with the general method of example 6 from (10aR)-9-bromo-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole and 2-bromoacetamide. | NC(=O)CN1CCN2c3cccc(Br)c3C[C@@H]2C1 | null | null | null |
629,233 | ord_dataset-0a66204fc43e49c2922e6f9107e6b62f | null | 2004-01-01T00:03:00 | true | [CH3:1][NH:2][S:3]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[CH2:9]2)(=[O:5])=[O:4].[NH:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]([CH:25]=O)=[CH:17]1>>[CH3:1][NH:2][S:3]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[C:9]2=[CH:25][C:18]1[C:19]2[C:24](=[CH:23]... | CNS(=O)(=O)c1ccc2c(c1)CC(=O)N2 | O=Cc1c[nH]c2ccccc12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 5-Methylaminosulfonyl-2-oxindole was condensed with indole-3-carboxaldehyde to give the title compound. | CNS(=O)(=O)c1ccc2c(c1)C(=Cc1c[nH]c3ccccc13)C(=O)N2 | null | null | null |
1,346,966 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | [Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([C@H:14]3[CH2:16][C@H:15]3[CH2:17][CH2:18][NH2:19])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].Cl[C:27]1[CH:28]=[C:29]([CH:32]=[C:33]([CH3:35])[N:34]=1)[C:30]#[N:31]>CS(C)=O.O>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([C@H:14]3[... | NCC[C@@H]1C[C@@H]1C1CCN(c2ncc(Cl)cn2)CC1 | Cc1cc(C#N)cc(Cl)n1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CS(C)=O | null | null | null | null | null | null | null | null | null | 150 | 8 | 2-{(1S,2S)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethanamine from step 3 of Example 5 (59 mg, 0.21 mmol) was dissolved in DMSO (1.0 ml). K2CO3 (86 mg, 0.62 mmol) and 2-chloro-6-methylisonicotinonitrile (31 mg, 0.21 mmol) from step 2 of this example were added and the mixture stirred at 150° C. overnigh... | Cc1cc(C#N)cc(NCC[C@@H]2C[C@@H]2C2CCN(c3ncc(Cl)cn3)CC2)n1 | null | null | null |
952,176 | ord_dataset-3feb2a95f66e4706a4a50c977ccd9bf8 | null | 2010-01-01T00:04:00 | true | C([NH:8][NH:9][C:10](=[O:34])[C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([C:18]2[CH:23]=[CH:22][N:21]3[C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[Cl:33])=[N:25][N:26]=[C:20]3[CH:19]=2)[CH:12]=1)(OC(C)(C)C)=O.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[C:24]1[N:21]2[CH:22]=[C... | Cc1ccc(C(=O)NNC(=O)OC(C)(C)C)cc1-c1ccn2c(-c3ccccc3Cl)nnc2c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | 1.5 | A solution of N′-boc-3-(3-(2-chlorophenyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl)-4-methylbenzohydrazide (300 mg, 0.63 mmol) in 3.0 mL of DCM at RT was treated with 2.0 mL of TFA. After 1.5 h of stirring, the volatiles were evaporated. The residue was dissolved in DCM, washed with 1 N NaOH followed by brine. The DCM layer... | Cc1ccc(C(=O)NN)cc1-c1ccn2c(-c3ccccc3Cl)nnc2c1 | null | null | null |
298,428 | ord_dataset-b6309a86b70f4ca08fd301828cacf950 | null | 1994-01-01T00:10:00 | true | [C:1]([NH:4][C:5]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=1[N+:24]([O-])=O)([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6](OCC)=[O:7])(=[O:3])[CH3:2]>C(O)(=O)C.[Pd]>[C:1]([NH:4][C:5]1([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:16][C:17]2[C:18](=[C:19]([CH3:23])[CH:20]=[CH:21][CH:22]=2)[NH:24][C:6]1=[O... | CCOC(=O)C(Cc1cccc(C)c1[N+](=O)[O-])(NC(C)=O)C(=O)OCC | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | 10 Grams of diethyl 2-acetylamino-2-(2-nitro-3-methylbenzyl)malonate and 1 g of 10% Pd-C were suspended in 50 ml of acetic acid, and the suspension was catalytically reduced under 3 to 3.5 atmospheric pressure at 60° to 70° C. by hydrogenation. After the hydrogenation was finished, the catalyst was removed by filtratio... | CCOC(=O)C1(NC(C)=O)Cc2cccc(C)c2NC1=O | null | null | null |
894,883 | ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded | null | 2009-01-01T00:08:00 | true | [NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19](O)=[O:20])[C:3]=1[S:22][C:23]([F:26])([F:25])[F:24].[CH:27]1([NH2:30])[CH2:29][CH2:28]1>O1CCOCC1.O>[CH:27]1([NH:30][C:19]([C:4]2[C:3]([S:22][C:23]([F:24])([F:26])[F:25])=[C:2]([NH2:1])[N:6]([C:7]... | NC1CC1 | Nc1c(SC(F)(F)F)c(C(=O)O)nn1-c1c(Cl)cc(C(F)(F)F)cc1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 2 | A mixture of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylthio-1H-pyrazole-3-carboxylic acid (0.85 g, 1.83 mmol) and 1,1-dicarbonylimidazole (0.36 g, 2.20 mmol) in dioxane was heated to. 55° C. for 2 hours. Cyclopropylamine (0.20 ml, 2.83 mmol) was then added and stirring continued at 55° C. for 6 ... | Nc1c(SC(F)(F)F)c(C(=O)NC2CC2)nn1-c1c(Cl)cc(C(F)(F)F)cc1Cl | null | 86.9 | null |
1,629,858 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH:11][C:12](=[O:22])[CH2:13][CH:14]2[CH:19]3[CH2:20][CH2:21][N:16]([CH2:17][CH2:18]3)[CH2:15]2)([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[C:2]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:7]=[CH:6][C:5]([C:8]([NH:11][C:12](=[O:22])... | CC(C)(NC(=O)CC1CN2CCC1CC2)c1ccc(Br)cc1 | OB(O)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Using general procedure E, N-(2-(4-bromophenyl)propan-2-yl)-2-(quinuclidin-3-yl)acetamide (200 mg, 0.550 mmol), phenylboronic acid (134 mg, 1.00 mmol) and [PdCl2(pddf)]CH2Cl2 gave the title compound as a viscous brown oil (58 mg, 32%). 1H NMR (500 MHz, CDCl3) δ 7.58-7.50 (m, 4H), 7.44-7.37 (m, 4H), 7.31 (t, J=7.0 Hz, 1... | CC(C)(NC(=O)CC1CN2CCC1CC2)c1ccc(-c2ccccc2)cc1 | null | 29.1 | null |
283,429 | ord_dataset-769fac6048e548eca2d49e48f972884b | null | 1994-01-01T00:01:00 | true | [OH:1][CH2:2][CH:3]([NH:13][C:14](=[O:38])[C:15]1[CH:20]=[CH:19][C:18]([N:21]([CH2:25][C:26]2[CH:27]=[C:28]3[C:33](=[CH:34][CH:35]=2)[N:32]=[C:31]([CH3:36])[NH:30][C:29]3=[O:37])[CH2:22][C:23]#[CH:24])=[CH:17][CH:16]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[CH:5]=1.[C:39](OC(=O)C)(=[O:41])[CH3:40]>>[C... | CC(=O)OC(C)=O | C#CCN(Cc1ccc2nc(C)[nH]c(=O)c2c1)c1ccc(C(=O)NC(CO)c2cccc([N+](=O)[O-])c2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Using an analogous procedure to that described in Example 4, N-[2-hydroxy-1-(3-nitrophenyl)ethyl]-p-[N-(2-methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl)-N-(prop-2-ynyl)amino]benzamide was reacted with acetic anhydride to give N-[2-acetoxy-1-(3-nitrophenyl)ethyl]-p-[N-(2-methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl)-N-... | C#CCN(Cc1ccc2nc(C)[nH]c(=O)c2c1)c1ccc(C(=O)NC(COC(C)=O)c2cccc([N+](=O)[O-])c2)cc1 | null | 56 | null |
1,543,665 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | I[C:2]1[CH:3]=[N:4][N:5]([CH3:16])[C:6]=1[C:7]1[CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[S:10][CH:11]=1.[F-].[K+].C([Si](CC)(CC)[C:22]([F:25])([F:24])[F:23])C>CN(C=O)C.CN(P(N(C)C)(N(C)C)=O)C.[Cu]I>[CH3:16][N:5]1[C:6]([C:7]2[CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[S:10][CH:11]=2)=[C:2]([C:22]([F:25])([F:24])[F:23])... | COC(=O)c1cc(-c2c(I)cnn2C)cs1 | CC[Si](CC)(CC)C(F)(F)F | null | [Cu]I | [F-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CN(C)P(=O)(N(C)C)N(C)C | null | null | null | null | null | null | null | null | null | 70 | 10 | To a solution of methyl 4-(4-iodo-1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate (470 mg, 1.35 mmol), copper (I) iodide (256 mg, 1.35 mmol) and potassium fluoride (78 mg, 1.35 mmol) in anhydrous DMF/HMPA (2 ml/2 mL) was added triethyl(trifluoromethyl)silane (745 mg, 4.04 mmol). The mixture was heated to 70° C. under ... | COC(=O)c1cc(-c2c(C(F)(F)F)cnn2C)cs1 | null | 74 | null |
104,782 | ord_dataset-b2a00a09c8494aaf9348c3a3af29d26e | null | 1983-01-01T00:04:00 | true | [N+:1]([C:4]1[CH:5]=[C:6]([CH:22]=[CH:23][CH:24]=1)[O:7][CH2:8][CH2:9][CH2:10][N:11]1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21])([O-])=O>[Pd].COCCO>[NH2:1][C:4]1[CH:5]=[C:6]([CH:22]=[CH:23][CH:24]=1)[O:7][CH2:8][CH2:9][CH2:10][N:11]1[C:12](=[O:21])[C:13]2=[CH:20][CH:19]=[CH:18][CH:17]=[C... | O=C1c2ccccc2C(=O)N1CCCOc1cccc([N+](=O)[O-])c1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COCCO | null | null | null | null | null | null | null | null | null | null | null | 0.75 | A suspension of N-[3-(3-nitrophenoxy)propyl]phthalimide (1.0 g; 3.1 mmoles) [prepared in Step A] and 10% palladium on carbon (0.2 g) in 100 ml of 2-methoxyethanol was hydrogenated in a Parr Apparatus at ambient temperature for 45 minutes. The reaction mixture was filtered and the filtrate was evaporated to dryness to g... | Nc1cccc(OCCCN2C(=O)c3ccccc3C2=O)c1 | null | 99.1 | null |
654,226 | ord_dataset-fe016e2f90e741a590ad77fd5933161f | null | 2004-01-01T00:11:00 | true | [CH2:1]([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[C:9](Cl)=[O:10])=[O:5])[CH3:2].[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([SH:19])=[CH:15][CH:14]=1.CCN(CC)CC>CCCCCC>[CH2:1]([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[C:9]([S:19][C:16]1[CH:17]=[CH:18][C:13]([CH3:12])=[CH:14][CH:15]=1)=[O:10])=[O:5])[CH3:2] | Cc1ccc(S)cc1 | CCOC(=O)C1CC1C(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CCCCCC | null | null | null | null | null | null | null | null | null | 25 | 3 | To a solution of 2-chlorocarbonyl-cyclopropanecarboxylic acid ethyl ester (5.30 g, 30 mmol) and 4-methylbenzene thiol (3.73 g, 30 mmol) in 150 mL hexane at 0° C. was added a solution of Et3N in 25 mL hexane dropwise. The reaction was warmed to room temperature and stirred for 3 h. The solid precipitate was removed by f... | CCOC(=O)C1CC1C(=O)Sc1ccc(C)cc1 | null | 99.4 | null |
1,679,211 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | [CH3:1][C:2]1[C:6]([C:7]2[C:16]3[O:15][CH2:14][C@H:13]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=4)[N:12]4[C:23](=[O:25])[NH:24][C:10]([C:11]=34)=[CH:9][CH:8]=2)=[C:5]([CH3:26])[O:4][N:3]=1.[Br:27]N1C(=O)CCC1=O>O1CCCC1.C(OCC)(=O)C>[Br:27][C:9]1[CH:8]=[C:7]([C:6]2[C:2]([CH3:1])=[N:3][O:4][C:5]=2[CH3:26])[C:16]2[O:15][... | Cc1noc(C)c1-c1ccc2[nH]c(=O)n3c2c1OC[C@@H]3c1ccccn1 | O=C1CCC(=O)N1Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 25 | 1 | A solution of (4S)-7-(3,5-dimethylisoxazol-4-yl)-4-pyridin-2-yl-4,5-dihydroimidazo[1,5,4-de][1,4]benzoxazin-2(1H)-one (2.50 g, 7.18 mmol) in tetrahydrofuran (47 mL) was treated with N-bromosuccinimide (1.40 g, 7.89 mmol) and stirred at room temperature for 1 h, at which time the reaction mixture was treated with additi... | Cc1noc(C)c1-c1cc(Br)c2[nH]c(=O)n3c2c1OC[C@@H]3c1ccccn1 | null | 97.8 | null |
1,229,503 | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | null | 2012-01-01T00:11:00 | true | [C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:12][CH:13]=[C:14]([C:17]([CH3:19])=O)[C:15]=2[OH:16])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH:20]([C:22]([NH:24][C:25]1[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[C:27]([N+:35]([O-:37])=[O:36])[CH:26]=1)=[S:23])[NH2:21]>Cl.CN(C)C=O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]... | COC(=O)c1ccc(NC(=S)NN)cc1[N+](=O)[O-] | CC(=O)c1csc(-c2ccc(C(C)(C)C)cc2)c1O | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | 48 | Dimethylformamide (1.3 mL) and conc. hydrochloric acid (1 drop) were added to 2-(4-t-butylphenyl)-3-hydroxy-4-methylcarbonylthiophene (71 mg, 0.26 mmol) synthesized in Reference Synthetic Example 33 and methyl 4-hydrazinocarbonothioylamino-2-nitrobenzoate (70 mg, 0.26 mmol) synthesized in Reference Synthetic Example 56... | COC(=O)c1ccc(NC(=S)NN=C(C)c2csc(-c3ccc(C(C)(C)C)cc3)c2O)cc1[N+](=O)[O-] | null | 80.3 | null |
1,267,227 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [CH2:1]([O:3][C:4](=[O:35])[CH2:5][C@H:6]([NH:23][C:24](=[O:34])[CH2:25][CH2:26][C:27]([O:29]C(C)(C)C)=[O:28])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2[O:21][CH3:22])=[CH:10][CH:9]=1)[CH3:2].O1CCOCC1>Cl>[CH2:1]([O:3][C:4](=[O:35])[CH2:5][C@H:6]([NH:23][C:24](=[O:34])[CH2:25... | CCOC(=O)C[C@@H](Cc1ccc(-c2cc(F)ccc2OC)cc1)NC(=O)CCC(=O)OC(C)(C)C | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | 1 | A solution of (R)-tert-butyl 4-(4-ethoxy-1-(5′-fluoro-2′-methoxybiphenyl-4-yl)-4-oxobutan-2-ylamino)-4-oxobutanoate, (65 mg, 0.13 mmol) in 4M HCl in 1,4-dioxane (671 μL, 2.68 mmol) is stirred at room temperature. After stirring for 1 hour, the reaction mixture is concentrated under reduced pressure. The obtained residu... | CCOC(=O)C[C@@H](Cc1ccc(-c2cc(F)ccc2OC)cc1)NC(=O)CCC(=O)O | null | 41 | null |
1,641,033 | ord_dataset-bcc0b01d4f58457a8733b10a099f43ba | null | 2015-01-01T00:10:00 | true | [Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][C:12]=2[CH3:21])=[O:9])[CH:3]=1.[CH3:22][O:23][CH2:24][CH2:25][NH2:26].C(NC(C)C)(C)C>C1COCC1>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([S:17](=[O:19])(=[O:18])[NH:26][CH2... | Cc1cc(S(=O)(=O)Cl)ccc1NC(=O)c1cc(Cl)ncn1 | COCCN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CC(C)NC(C)C | null | null | null | null | null | null | null | null | null | 25 | 18 | A solution of 4-(6-chloropyrimidine-4-carboxamido)-3-methylbenzene-1-sulfonyl chloride (Intermediate 30, 400 mg; 1.15 mmol) in THF (20 ml) was treated with 2-methoxyethanamine (125 mL; 1.4 mmol) and diisopropylamine (0.4 ml; 2.9 mmol). After stirring at RT for 18 hours the solvent was removed in vacuo and the residue r... | COCCNS(=O)(=O)c1ccc(NC(=O)c2cc(Cl)ncn2)c(C)c1 | null | null | null |
822,965 | ord_dataset-ec58fad8331a42c5a67ad75aac6713b4 | null | 2008-01-01T00:05:00 | true | [F:1][CH:2]([F:25])[C:3]1[N:8]2[N:9]=[CH:10][C:11]([C:12](O)=[O:13])=[C:7]2[N:6]=[C:5]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)[CH:4]=1.[NH2:26][C:27]1[CH:28]=[C:29]([S:33]([NH:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=2)(=[O:35])=[O:34])[CH:30]=[CH:31][CH:32]=1>>[N:39]1... | Nc1cccc(S(=O)(=O)NCc2ccccn2)c1 | O=C(O)c1cnn2c(C(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from 7-difluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.1) and 3-amino-N-pyridin-2-ylmethyl-benzenesulfonamide (example B.6) according to general procedure II. Yellow solid. MS (ISP) 601.1 [(M−H−]; mp 208° C. | O=C(Nc1cccc(S(=O)(=O)NCc2ccccn2)c1)c1cnn2c(C(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12 | null | null | null |
1,564,427 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [C:1]([O:5][C@@H:6]([C:10]1[C:28]([CH3:29])=[CH:27][C:13]2[N:14]=[C:15]([N:17]3[CH2:26][CH2:25]C4N=CC=CC=4C3)[S:16][C:12]=2[C:11]=1[C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2].Cl.[F:38][C:39]([F:50])([F:49])[C:40]1[N:44]2CCN[CH2:48][C:43]2=[N:42][N:41]=1>>[C:1]([O... | FC(F)(F)c1nnc2n1CCNC2 | Cc1cc2nc(N3CCc4ncccc4C3)sc2c(-c2ccc(Cl)cc2)c1[C@H](OC(C)(C)C)C(=O)O | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared in a similar manner as (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(7,8-dihydro-1,6-naphthyridin-6(5H)-yl)-5-methylbenzo[d]thiazol-6-yl)acetic acid except using 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride instead of 5,6,7,8-tetrahydro-1,6-naphthyridine, dihydrochloride, hy... | Cc1cc2nc(N3CCn4c(nnc4C(F)(F)F)C3)sc2c(-c2ccc(Cl)cc2)c1[C@H](OC(C)(C)C)C(=O)O | null | null | null |
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