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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
601,543 | ord_dataset-82e842e611ef4a05b6e7f9ea0a46d52d | null | 2003-01-01T00:07:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10](Cl)=[O:11])[CH:6]=[CH:7][CH:8]=1.[NH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[N:18][CH:19]=1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]([NH:13][C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[N:18][CH:19]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1 | COc1cccc(CC(=O)Cl)c1 | COc1ccc(N)cn1 | 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 as described in Example 1.A, using 3-methoxyphenylacetyl chloride (4.8 g, 26.0 mmol) and 5-amino-2-methoxypyridine (3.23 g, 26.0 mmol) to afford the title compound (7.0 g, 99% yield): ES-MS (m/z) 272. | COc1cccc(CC(=O)Nc2ccc(OC)nc2)c1 | null | 98.9 | null |
642,535 | ord_dataset-ce71a906ea9c4399a2014cbaaff88c8f | null | 2004-01-01T00:07:00 | true | [N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[C:13]#[N:14])([O-])=O.[CH2:15]([N:17]1[CH2:22][CH2:21]N[CH2:19][CH2:18]1)[CH3:16].O>CN(C=O)C>[CH2:15]([N:17]1[CH2:22][CH2:21][N:1]([C:4]2[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=2[C:13]#[N:14])[CH2:19][CH2:18]1)[CH3:16] | N#Cc1c([N+](=O)[O-])cccc1[N+](=O)[O-] | CCN1CCNCC1 | null | null | null | 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 | 90 | null | 2,6-Dinitrobenzenecarbonitrile (1.0 eq) and ethylpiperazine (3.6 eq) were dissolved in DMF. The resulting solution heated at 90° C. for 2 hours. The solution was cooled to room temperature and poured into H2O. A precipitate formed which was filtered to yield the desired product as a brown solid. LC/MS m/z 260.1 (MH+), ... | CCN1CCN(c2cccc([N+](=O)[O-])c2C#N)CC1 | null | null | null |
1,102,971 | ord_dataset-375a420ee9b042918ddca20f02df37d3 | null | 2011-01-01T00:11:00 | true | [O:1]=[C:2]1[N:7]2[C@H:8]([C:16]3[CH:21]=[C:20]([F:22])[C:19]([F:23])=[C:18]([F:24])[CH:17]=3)[CH2:9][N:10]([C:12]([O:14][CH3:15])=[O:13])[CH2:11][C@@H:6]2[CH:5]=[CH:4][CH2:3]1.[H][H]>CO.[Pt]=O>[O:1]=[C:2]1[N:7]2[C@H:8]([C:16]3[CH:17]=[C:18]([F:24])[C:19]([F:23])=[C:20]([F:22])[CH:21]=3)[CH2:9][N:10]([C:12]([O:14][CH3:... | COC(=O)N1C[C@@H]2C=CCC(=O)N2[C@H](c2cc(F)c(F)c(F)c2)C1 | [H][H] | null | O=[Pt] | 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 | Platinum oxide (10 mg) was added to a solution of methyl (4R*,9aS*)-6-oxo-4-(3,4,5-trifluorophenyl)-1,3,4,6,7,9a-hexahydropyrido[1,2-a]pyrazine-2-carboxylate obtained by performing the above method again (292 mg) in methanol (5 mL), and the reaction solution was stirred in a hydrogen atmosphere at room temperature for ... | COC(=O)N1C[C@@H]2CCCC(=O)N2[C@H](c2cc(F)c(F)c(F)c2)C1 | null | null | null |
408,741 | ord_dataset-324fb6fdc2414cb79e436bf5d04d4bd2 | null | 1998-01-01T00:08:00 | true | [Cl:1][C:2]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2C)[CH2:6][CH2:5]1)=[O:3].[F:17]C1C=CC=CC=1N1CCNCC1.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.N1C=CC=CC=1>ClCCl>[Cl:1][C:2]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:17])[CH2:6][CH2:5]1)=[O:3] | Cc1ccccc1N1CCN(C(=O)Cl)CC1 | Fc1ccccc1N1CCNCC1 | null | O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl | 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 | null | null | Compound 41A is prepared according to the procedure described for compound 15A, using the following reactants: 1-(2-fluorophenyl)piperazine (1.54 g, 8.06 mmol); triphosgene (850 mg, 2.85 mmol); pyridine (0.69 ml, 8.6 mmol); dichloromethane (60 ml). | O=C(Cl)N1CCN(c2ccccc2F)CC1 | null | 88 | null |
1,299,924 | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | null | 2013-01-01T00:05:00 | true | [Br:1][C:2]1[C:3]([C:8]2[NH:12][CH:11]=[N:10][N:9]=2)=[C:4]([NH2:7])[S:5][CH:6]=1.Cl.[F:14][C:15]1[CH:16]=[N:17][C:18]2[C:23]([CH:24]=1)=[CH:22][CH:21]=[CH:20][C:19]=2[CH2:25][C:26](O)=[O:27].[I-].ClC1C=CC=C[N+]=1C.C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[C:3]([C:8]2[N:12]=[CH:11][NH:10][N:9]=2)=[C:4]([NH:7][C:26](=[O:27])[CH2... | O=C(O)Cc1cccc2cc(F)cnc12 | Nc1scc(Br)c1-c1nnc[nH]1 | null | C[n+]1ccccc1Cl | Cl | [I-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | ClCCl | null | null | null | null | null | null | null | null | null | null | 1 | 4-Bromo-3-(4H-1,2,4-triazol-3-yl)thiophen-2-amine (17 mg, 69.4 umol), 2-(3-fluoroquinolin-8-yl)acetic acid hydrogen chloride (22 mg, 91.0 umol), 2-chloro-1-methylpyridinium iodide (101 mg, 395 umol) and triethylamine (0.2 ml) in methylene chloride (1 ml) was heated to reflux. After stirring for 1 h, the solution was co... | O=C(Cc1cccc2cc(F)cnc12)Nc1scc(Br)c1-c1nc[nH]n1 | null | null | null |
1,543,773 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[C:16]([CH2:17][CH2:18][CH2:19][OH:20])=[N:15][O:14][N:13]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[F:8].[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl>[CH3:21][S:22]([O:20][CH2:19][CH2:18][CH2:17][C:16]1[C:12]([C:10]([NH:9][C:4]2[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Cl:1])[CH:3]=2)=[O:11])=[N... | CS(=O)(=O)Cl | O=C(Nc1ccc(F)c(Cl)c1)c1nonc1CCCO | 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 | 0 | null | N-(3-Chloro-4-fluorophenyl)-4-(3-hydroxypropyl)-1,2,5-oxadiazole-3-carboxamide (60 mg, 0.20 mmol) was dissolved in anhydrous DCM (2 mL), followed by addition of TEA (57 μL, 0.41 mmol). The reaction was stirred and cooled to 0° C., and methanesulfonyl chloride (29 μL, 0.37 mmol) was added drop-wise. The reaction was que... | CS(=O)(=O)OCCCc1nonc1C(=O)Nc1ccc(F)c(Cl)c1 | null | 79.4 | null |
1,137,009 | ord_dataset-aaeaab5f3720492494c1cbbdd0ed2820 | null | 2012-01-01T00:02:00 | true | [F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:30]([CH2:37][CH2:38][CH2:39][CH2:40][NH:41][C:42](=[O:51])[O:43][CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[CH:29][CH:28]=1)(C(C)(C)C)(C)C>C1COCC1>[OH:26][C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2... | CC(C)(C)[Si](C)(C)Oc1ccc(CCCCNC(=O)OCc2ccccc2)c2ccccc12 | null | null | CCCC[N+](CCCC)(CCCC)CCCC | [F-] | 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 | 2 | Tetrabutylammonium fluoride (1 M in THF, 1.0 mL) was added to a solution of benzyl 4-[4-(tert-butyldimethylsilyloxy)naphthalen-1-yl]butylcarbamate (19, 380 mg, 0.80 mmol) in anhydrous THF (15 ml) at room temperature. The reaction mixture was stirred for 2 h and concentrated to dryness. The residue was purified by colum... | O=C(NCCCCc1ccc(O)c2ccccc12)OCc1ccccc1 | null | 102.7 | null |
124,308 | ord_dataset-6d96290c60d941d098c4ddc9d0cb01a0 | null | 1984-01-01T00:12:00 | true | [Br:1]Br.[CH3:3][S:4]([N:7]1[CH2:12][CH2:11][CH2:10][S:9][C:8]1=[CH:13][N+:14]([O-:16])=[O:15])(=[O:6])=[O:5].CCOCC>C(Cl)Cl>[CH3:3][S:4]([N:7]1[CH2:12][CH2:11][CH2:10][S:9][C:8]1=[C:13]([Br:1])[N+:14]([O-:16])=[O:15])(=[O:5])=[O:6] | BrBr | CS(=O)(=O)N1CCCSC1=C[N+](=O)[O-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCOCC | null | null | null | null | null | null | null | null | null | null | 0.17 | A solution of 1.6 g of bromine in 10 ml of methylene chloride was added drop-by-drop over a period of 10 minutes to a solution of 2.38 g of (1A) in 50 ml of methylene chloride at 0° C. and under a nitrogen blanket. The resulting mixture was stirred for a further 10 minutes, charcoaled, and stripped of solvent. The resi... | CS(=O)(=O)N1CCCSC1=C(Br)[N+](=O)[O-] | null | null | null |
928,208 | ord_dataset-cc0899cd744f4f7f8e7f2463560faad1 | null | 2009-01-01T00:12:00 | true | [CH3:1][C:2]1([CH3:26])[O:7][C:6](=[O:8])[CH:5]([CH:9]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:10]2[C:18]3[C:13](=[N:14][CH:15]=[CH:16][CH:17]=3)[NH:12][CH:11]=2)[C:4](=[O:25])[O:3]1.C([Si](C)(C)N1C2=NC=CC([Cl:41])=C2C=C1)(C)(C)C>>[Cl:41][C:17]1[CH:16]=[CH:15][N:14]=[C:13]2[NH:12][CH:11]=[C:10]([CH:9]([C:19]3... | CC1(C)OC(=O)C(C(c2ccccc2)c2c[nH]c3ncccc23)C(=O)O1 | CC(C)(C)[Si](C)(C)n1ccc2c(Cl)ccnc21 | 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-[(4-Chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxane-4,6-dione was prepared following the procedure described for preparation of 2,2-dimethyl-5-[phenyl-(1H-pyrrolo[2,3-b]pyridin-3-yl)-methyl]-[1,3]dioxane-4,6-dione in example 1, using 1-(tert-butyl-dimethyl-silanyl)-4-chloro-1H-pyrrolo[2... | CC1(C)OC(=O)C(C(c2ccccc2)c2c[nH]c3nccc(Cl)c23)C(=O)O1 | null | null | null |
1,219,848 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | Cl.[CH3:2][O:3][C:4](=[O:11])[C@@H:5]1[CH2:9][C@@H:8]([OH:10])[CH2:7][NH:6]1.[C:12](ON1C(=O)CCC1=O)([O:14][CH2:15][CH:16]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]2[C:17]1=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:13]>C(=O)([O-])[O-].[Na+].[Na+].C1COCC1>[N:6]1([C:12]([O:14][CH2:15][CH:16]2[C:17]3[C:22](=[CH:21][C... | COC(=O)[C@@H]1C[C@@H](O)CN1 | O=C(OCC1c2ccccc2-c2ccccc21)ON1C(=O)CCC1=O | null | Cl | O=C([O-])[O-] | [Na+] | 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 | L-hydroxyproline methylester hydrochloride is reacted with Fmoc-OSu in aqueous 1.0 N sodium carbonate/THF at room temperature. After completion of the reaction, Fmoc-Pro(4-OH)—OMe is isolated by precipitation. Fmoc-Pro(4-OH)—OMe is then added dropwise into a solution of trisphosgene (0.6 eq.) in THF to give a chlorocar... | COC(=O)[C@@H]1CC(O)CN1C(=O)OCC1c2ccccc2-c2ccccc21 | null | null | null |
1,673,222 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | Cl.Cl.[Cl:3][C:4]1[C:5]([CH3:40])=[C:6]([NH:10][C:11]([C:13]2[C:21]3[N:20]=[C:19]([C@@H:22]4[CH2:26][CH2:25][CH2:24][NH:23]4)[NH:18][C:17]=3[CH:16]=[C:15]([NH:27][C:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[C:36]([F:39])([F:38])[F:37])=[O:29])[CH:14]=2)=[O:12])[CH:7]=[CH:8][CH:9]=1.C=O.B.N1C=CC=C[C:45]=1C>CO>[C... | Cc1c(Cl)cccc1NC(=O)c1cc(NC(=O)c2ccccc2C(F)(F)F)cc2[nH]c([C@@H]3CCCN3)nc12 | Cc1ccccn1 | null | B | C=O | Cl | 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 | 25 | 8 | To a solution of N-(3-chloro-2-methylphenyl)-2-[(2S)-pyrrolidin-2-yl]-6-({[2-(trifluoromethyl)phenyl]carbonyl}amino)-1H-benzimidazole-4-carboxamide (Example 71) (25 mg) in MeOH (0.4 mL), was added 38% aqueous formaldehyde solution (7.2 μL), and the mixture was stirred at room temperature overnight. To the mixture was a... | Cc1c(Cl)cccc1NC(=O)c1cc(NC(=O)c2ccccc2C(F)(F)F)cc2[nH]c([C@@H]3CCCN3C)nc12 | null | 48.7 | null |
1,373,156 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | [Br:1][C:2]1[C:10]2[C:5]([NH:6][CH:7]=[N:8][C:9]=2[Cl:11])=[N:4][CH:3]=1.[CH3:12][N:13]([CH3:17])[CH2:14][CH2:15]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[Br:1][C:2]1[C:10]2[C:9]([Cl:11])=[N:8][CH:7]=[N:6][C:5]=2[N:4]([CH2:15][CH2:14][N:13]([CH3:17])[CH3:12])[CH:3]=1 | Clc1nc[nH]c2ncc(Br)c1-2 | CN(C)CCO | null | CCOC(=O)/N=N/C(=O)OCC | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | 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 | null | To a solution of 5-bromo-4-chloro-1H-pyrrolo[2,3-d]pyrimidine (200 mg, 0.860 mmol), 2-(dimethylamino)ethanol (230 mg, 2.58 mmol) and triphenylphosphine (451 mg, 1.721 mmol) in Tetrahydrofuran (THF) (10 mL) was added dropwise DEAD (0.272 mL, 1.721 mmol). The solution was allowed to stir at room temperature. After 2 hr t... | CN(C)CCn1cc(Br)c2c(Cl)ncnc21 | null | 67 | null |
357,865 | ord_dataset-58ec5adfcd8648dc9e26ee757d289517 | null | 1997-01-01T00:03:00 | true | [C:1]1([CH2:7][C:8]2[CH:25]=[CH:24][CH:23]=[CH:22][C:9]=2[C:10]([NH:12][C:13]2[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=2)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:28])=O>>[C:1]1([CH2:7][C:8]2[CH:25]=[CH:24][CH:23]=[CH:22][C:9]=2[C:10]([NH:12][C:13]2[CH:21]=[CH:20][C:16]([C:17]([Cl:28])=[O:18])=... | O=C(O)c1ccc(NC(=O)c2ccccc2Cc2ccccc2)cc1 | O=S(Cl)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 | null | null | A mixture of 2.0 g of 4-[[2-(phenylmethyl)benzoyl]amino]benzoic acid in 2.0 ml of thionyl chloride is heated on a steam bath for 1 hour. The volatiles are evaporated in vacuo to give 1.53 g of the desired product as an oil. M+ =346 as methyl ester. | O=C(Cl)c1ccc(NC(=O)c2ccccc2Cc2ccccc2)cc1 | null | null | null |
544,447 | ord_dataset-d31180f42ced44719fd9e72685c798bf | null | 2002-01-01T00:05:00 | true | [C:1]1([N:7]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:8](=[O:25])[O:9][CH2:10][C:11]2([OH:24])[CH2:17][CH2:16][CH2:15][C:14]3[C:18]([OH:22])=[CH:19][CH:20]=[CH:21][C:13]=3[CH:12]2[OH:23])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41]>CN(C=O)C.CCOC(C... | CCOC(=O)CBr | O=C(OCC1(O)CCCc2c(O)cccc2C1O)N(c1ccccc1)c1ccccc1 | 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 | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 25 | 18 | To a mixture of [(5SR,6SR)-1,5,6-trihydroxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl]methyl N,N-diphenylcarbamate (461 mg) and potassium carbonate (304 mg) in DMF (8 ml) was added ethyl bromoacetate (0.244 ml) and stirred at room temperature for 18 hours. The reaction mixture was diluted with EtOAc, washed with wate... | CCOC(=O)COc1cccc2c1CCCC(O)(COC(=O)N(c1ccccc1)c1ccccc1)C2O | null | null | null |
899,799 | ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded | null | 2009-01-01T00:08:00 | true | [N:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)=[N+:2]=[N-:3].[CH2:13]([OH:16])[C:14]#[CH:15]>C(O)(C)(C)C.O.O>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([CH2:4][N:1]2[CH:15]=[C:14]([CH2:13][OH:16])[N:3]=[N:2]2)=[CH:6][CH:7]=1 | COc1ccc(CN=[N+]=[N-])cc1 | C#CCO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(C)(C)O | null | null | null | null | null | null | null | null | null | null | 48 | 93 mmol 1-(azidomethyl)-4-methoxybenzene, 110 mmol propargyl alcohol were mixed in 230 ml tert-butyl alcohol/H2O (1:1) solution. 1 mmol CuSO4.5H2O and 10 mmol Ascorbic acid sodium salts dissolved in 2 ml water were added into the solution. The mixture was stirred for 2 days. After evaporation, the mixture was purified ... | COc1ccc(Cn2cc(CO)nn2)cc1 | null | 59.1 | null |
302,048 | ord_dataset-9ad0840101374618a7d5c4e4521c82d1 | null | 1994-01-01T00:12:00 | true | Br[CH2:2][C:3]1[CH:19]=[CH:18][C:6]2[S:7][CH:8]=[C:9]([C:10](=[CH:15][O:16][CH3:17])[C:11]([O:13][CH3:14])=[O:12])[C:5]=2[CH:4]=1.[C:20]1([OH:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:26]([CH2:2][C:3]1[CH:19]=[CH:18][C:6]2[S:7][CH:8]=[C:9]([C:10](=[CH:15][O:16][CH3:17])[C:11]([O:... | COC=C(C(=O)OC)c1csc2ccc(CBr)cc12 | Oc1ccccc1 | 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 | 50 | null | A mixture of 1 g of methyl α-(5-bromomethyl-3-benzo[b]-thienyl)-β-methoxyacrylate (see Example 11 ), 0.28 g of phenol and 2 g of potassium carbonate in 20 ml of dimethylformamide is heated for 2 hours at 50° C. The mixture is cooled to room temperature and filtered, and the filtrate is then concentrated under reduced p... | COC=C(C(=O)OC)c1csc2ccc(COc3ccccc3)cc12 | null | null | null |
300,426 | ord_dataset-fb70ed83140e4f53a907d87192ad748c | null | 1994-01-01T00:11:00 | true | [OH-].[K+].C([O:5][C:6](=[O:29])[CH:7]([C:14]([NH:16][C:17]1[C:22]([O:23][CH3:24])=[CH:21][C:20]([O:25][CH3:26])=[CH:19][C:18]=1[O:27][CH3:28])=[O:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)C>C(O)C.O>[CH3:28][O:27][C:18]1[CH:19]=[C:20]([O:25][CH3:26])[CH:21]=[C:22]([O:23][CH3:24])[C:17]=1[NH:16][C:14]([CH:7]([C:8... | CCOC(=O)C(C(=O)Nc1c(OC)cc(OC)cc1OC)c1ccccc1 | null | null | [K+] | [OH-] | 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 | null | 41 | To a stirred solution of KOH (10.70 g, 0.191 mol) in absolute ethanol (1.1 L) was added α-[[(2,4,6-trimethoxyphenyl)amino]carbonyl] benzene acetic acid ethyl ester (55.28 g, 0.1480 mol), and the mixture was stirred for 41 hours. The resulting suspension was diluted with H2O (~900 mL) and rotoevaporated to remove ethano... | COc1cc(OC)c(NC(=O)C(C(=O)O)c2ccccc2)c(OC)c1 | null | null | null |
118,467 | ord_dataset-7a32ed4947a84db9890d8863ca9e55fb | null | 1984-01-01T00:06:00 | true | [C:1]([NH:4][NH2:5])(=[O:3])[CH3:2].N1C=CC=CC=1.[Br:12][C:13]([Br:18])([Br:17])[C:14](Cl)=[O:15]>C(#N)C>[C:1]([N:4]([C:14](=[O:15])[C:13]([Br:18])([Br:17])[Br:12])[NH2:5])(=[O:3])[CH3:2] | CC(=O)NN | O=C(Cl)C(Br)(Br)Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | CC#N | null | null | null | null | null | null | null | null | null | null | 0.5 | 4.68 g (0.063 mol) of acetohydrazide (2-a) and 5 g (0.063 mol) of pyridine were dissolved in 50 ml of acetonitrile, and stirred with cooling in an ice-bath. Thereto, a solution of 20 g (0.064 mol) of tribromoacetic acid chloride (which was prepared from tribromoacetic acid and thionyl chloride, and had b.p. of 800°-81°... | CC(=O)N(N)C(=O)C(Br)(Br)Br | null | 47.6 | null |
616,522 | ord_dataset-31fc6d0085ca4d8dbbcd3a5fa9dcedfb | null | 2003-01-01T00:11:00 | true | [ClH:1].Cl.O[CH:4]([CH2:16][N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[CH2:5][O:6][NH:7][C:8]([C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)=[NH:9]>S(Cl)(Cl)=O>[ClH:1].[ClH:1].[Cl:1][CH:4]([CH2:16][N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[CH2:5][O:6][NH:7][C:8]([C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=... | N=C(NOCC(O)CN1CCCCC1)c1cccnc1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=S(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | 1 | 17.5 g (0.05 mole) of N-[2-hydroxy-3-(1-piperidinyl)propoxy]-3-pyridinecarboximidamide dihydrochloride was dissolved in 50 ml of thionyl chloride, boiled for one hour, then the mixture was evaporated to dryness. The residue was dissolved in 300 ml of methanol, treated with charcoal and after filtration the solvent was ... | N=C(NOCC(Cl)CN1CCCCC1)c1cccnc1 | null | null | null |
1,678,034 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | [OH:1][CH2:2][C:3]1[CH:4]=[C:5]([C:13]([O:15][CH3:16])=[O:14])[CH:6]=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9]>C(Cl)Cl.O=[Mn]=O>[CH:2]([C:3]1[CH:12]=[C:7]([C:8]([O:10][CH3:11])=[O:9])[CH:6]=[C:5]([CH:4]=1)[C:13]([O:15][CH3:16])=[O:14])=[O:1] | COC(=O)c1cc(CO)cc(C(=O)OC)c1 | null | null | O=[Mn]=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 | 6 | To a solution of 3.15 g (14.1 mmol) of dimethyl 5-(hydroxymethyl)isophthalate (prepared as described in Dimick et al., J. Am. Chem. Soc. (1999) 121, No. 44, 10286-10296) in 60 mL of DCM was added 7.34 g (84.4 mmol) of MnO2. The mixture was stirred at reflux for about 16 h and an additional 3.5 g of MnO2 was added. Refl... | COC(=O)c1cc(C=O)cc(C(=O)OC)c1 | null | null | null |
1,430,321 | ord_dataset-5e6956e6e8c24a168866a253f4a66c6c | null | 2014-01-01T00:05:00 | true | [NH2:1][C:2]1[S:3][C:4]2[CH2:26][CH2:25][CH2:24][CH2:23][C:5]=2[C:6]=1[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)=[O:8].[N:27]1([S:33]([C:36]2[CH:37]=[C:38]([CH:42]=[CH:43][CH:44]=2)[C:39](O)=[O:40])(=[O:35])=[O:34])[CH2:32][CH2:31][O:30][CH2:29][CH2... | Nc1sc2c(c1C(=O)Nc1ccc(Cc3ccncc3)cc1)CCCC2 | O=C(O)c1cccc(S(=O)(=O)N2CCOCC2)c1 | null | CN(C)C(On1nnc2cccnc21)=[N+](C)C | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 60 | 8 | To a mixture of 9.1 mg of 2-amino-N-[4-(pyridin-4-ylmethyl)phenyl]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide, 8.1 mg of 3-(morpholine-4-sulfonyl)benzoic acid, 0.016 mL of N,N-diisopropylethylamine, and 0.5 mL of DMF was added a mixture of 11.4 mg of HATU and 0.1 mL of DMF, followed by stirring at 60° C. overnig... | O=C(Nc1sc2c(c1C(=O)Nc1ccc(Cc3ccncc3)cc1)CCCC2)c1cccc(S(=O)(=O)N2CCOCC2)c1 | null | 57.6 | null |
699,214 | ord_dataset-4e9c2fa02a7544fd839206719263345f | null | 2006-01-01T00:02:00 | true | [CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH3:10])=[N+:7]([O-])[CH:8]=1)[CH3:2].C(N(CC)CC)C.C(Cl)[Cl:19]>CCOC(C)=O>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:10][Cl:19])=[N:7][CH:8]=1)[CH3:2] | ClCCl | CCc1ccc(C)[n+]([O-])c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 20 | null | To a solution of 5-ethyl-2-methyl-pyridine-1-oxide (427 mg, 3.11 mmol, example 45c) in CH2Cl2 (2 mL) is added a solution (0.2 mL) of phosphorous (v) trichloride oxide (327 μL) in CH2Cl2 (2 mL). Added simultaneously the remaining phosphorous (v) trichloride oxide solution and a solution of triethylamine (488 μL) in CH2C... | CCc1ccc(CCl)nc1 | null | null | null |
754,929 | ord_dataset-1b0cd79134f0450eaac8396a4f956c30 | null | 2007-01-01T00:02:00 | true | [F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([NH:12][C:13](=[O:22])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[S:11])[CH:5]=[CH:6][C:7]=1[OH:8].Cl[C:24]1[C:25]2[S:32][CH:31]=[C:30]([CH3:33])[C:26]=2[N:27]=[CH:28][N:29]=1.N12CCN(CC1)CC2>CC#N>[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([NH:12][C:13](=[O:22])[CH2:14]... | Cc1csc2c(Cl)ncnc12 | O=C(Cc1ccc(F)cc1)NC(=S)Nc1ccc(O)c(F)c1 | null | C1CN2CCN1CC2 | 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 | 25 | 4 | To a mixture of 1-(3-fluoro-4-hydroxyphenyl)-3-(2-(4-fluorophenyl)acetyl)thiourea (24 mg, 0.075 mmol, Compound A of Example 3), 4-chloro-7-methylthieno[3,2-d]pyrimidine (13.8 mg, 0.075 mmol, commercially available) and 1,4-diazabicyclo[2.2.2]octane (DABCO, 8.4 mg, 0.075 mmol) was added MeCN (2 mL). The reaction was sti... | CC1=CSC2C(Oc3ccc(NC(=S)NC(=O)Cc4ccc(F)cc4)cc3F)=NC=NC12 | null | 31 | null |
617,518 | ord_dataset-2952e63264f5422a84e12cca1e0541ee | null | 2003-01-01T00:12:00 | true | [CH2:1]([C:7]1([CH3:12])[O:11][CH2:10][CH2:9][O:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].P(=O)(O)(O)O>[Pd]>[CH3:12][CH:7]([O:8][CH2:9][CH2:10][OH:11])[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6] | CCCCCCC1(C)OCCO1 | null | null | [Pd] | O=P(O)(O)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 | 2-Hexyl-2-methyl-1,3-dioxolane (30 g, 0.17 mol), the palladium catalyst (2) (2.2 g) and phosphoric acid (110 mg) were charged in a 70-mL autoclave, followed by a reaction under a hydrogen pressure of 10 MPa at 150° C. for 5 hours. After completion of the reaction, the catalyst was removed by filtration to obtain a crud... | CCCCCCC(C)OCCO | null | 100.2 | null |
672,941 | ord_dataset-e90cd41afe844e49875435eb99903799 | null | 2005-01-01T00:05:00 | true | Br[C:2]1[CH:9]=[N:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[F:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:12]=1B1OC(C)(C)C(C)(C)O1>>[F:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:12]=1[C:2]1[CH:9]=[N:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5] | CC1(C)OB(c2cc([N+](=O)[O-])ccc2F)OC1(C)C | N#Cc1ccncc1Br | 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-Bromoisonicotinonitrile (2.0 g, 10.9 mmol) was coupled to 2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (3.8 g, 14.2 mmol) using the method in Example 51. Purification by chromatography on silica gel eluting with dichloromethane containing 10% isohexane gave 3-(2-fluoro-5-nitrophenyl)isonicotino... | N#Cc1ccncc1-c1cc([N+](=O)[O-])ccc1F | null | null | null |
138,285 | ord_dataset-3fa0a6b7d51b4fc6a5380aa0d03ac884 | null | 1985-01-01T00:12:00 | true | [F:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:3]=1[C:4](=[NH:8])[O:5][CH2:6][CH3:7].[Cl:14][C:15]1[C:16]([O:25][C:26]2[CH:31]=[CH:30][C:29]([N:32]=[C:33]=[O:34])=[CH:28][CH:27]=2)=[N:17][CH:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:20]=1>C(OCC)C>[Cl:14][C:15]1[C:16]([O:25][C:26]2[CH:31]=[CH:30][C:29]([NH:32][C:33... | CCOC(=N)c1c(F)cccc1F | O=C=Nc1ccc(Oc2ncc(C(F)(F)F)cc2Cl)cc1 | null | null | 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 | 20 | 18 | A mixture of ethyl 2,6-difluorobenzimidate (0.14 g), 3-chloro-5-trifluoromethyl-2-(4-isocyanatophenoxy)pyridine (0.24 g), and diethyl ether (10 ml) was stirred at 20° C. for 18 hours, after which the solvent was removed by evaporation and the residual solid recrystallised from petroleum ether (boiling range 60°-80° C.)... | CCOC(=NC(=O)Nc1ccc(Oc2ncc(C(F)(F)F)cc2Cl)cc1)c1c(F)cccc1F | null | 76.7 | null |
610,940 | ord_dataset-73916d628db147c89020b3baac642d48 | null | 2003-01-01T00:09:00 | true | [CH2:1]([O:3][C:4](=[O:14])[CH2:5][CH:6]([CH2:12]Br)[CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)[CH3:2].[N-:15]=[N+:16]=[N-:17].[Na+]>CS(C)=O.O>[CH2:1]([O:3][C:4](=[O:14])[CH2:5][CH:6]([CH2:12][N:15]=[N+:16]=[N-:17])[CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)[CH3:2] | [N-]=[N+]=[N-] | CCOC(=O)CC(CBr)C1CCCC1 | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | O | null | null | null | null | null | null | null | null | null | 60 | null | Preparation of 3-Azidomethyl-3-cyclopentyl-propionic acid ethyl ester—A solution of 3-bromomethyl-3-cyclopentyl-propionic acid ethyl ester (4.4 g, 28.5 mmol) and NaN3 (2.0 g, 31.4 mmol) in 25 mL of DMSO is warmed to 60° C. for 12 hours. The mixture is cooled to room temperature and diluted with 100 mL of H2O. Extractio... | CCOC(=O)CC(CN=[N+]=[N-])C1CCCC1 | null | 74.8 | null |
1,722,104 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | [S:1](Cl)([C:4]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:9]([N:10]([CH3:12])[CH3:11])[C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])=[O:2].[CH3:18][N:19]([CH3:36])[CH2:20][CH2:21][S:22][S:23][C:24]1[CH:29]=[CH:28][C:27]([CH:30]([OH:35])[C:31](F)(F)F)=[CH:26][CH:25]=1.C1N2CCN(CC2)C1.O>C(Cl)Cl>[CH3:18][N:19]([CH3:36])[CH2:20][CH2:21][S:22... | CN(C)CCSSc1ccc(C(O)C(F)(F)F)cc1 | CN(C)c1cccc2c(S(=O)(=O)Cl)cccc12 | null | C1CN2CCN1CC2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | ClCCl | null | null | null | null | null | null | null | null | null | null | 4 | Dansyl chloride (37.5 mg, 0.13 mmol) dissolved in dry CH2Cl2 (0.5 mL) was added to the crude 1-[4-(2-dimethylamino-ethyldisulfanyl)-phenyl]-2,2,2-trifluoro-ethanol obtained above. To this solution was added dropwise a solution of DABCO (157 mg, 1.4 mmol) dissolved in dry CH2Cl2 (0.25 mL). After 4 hours at room temperat... | CC(OS(=O)(=O)c1cccc2c(N(C)C)cccc12)c1ccc(SSCCN(C)C)cc1 | null | null | null |
1,243,618 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([CH:18]3[C:27]([CH3:29])([CH3:28])[CH2:26][C:25]4[C:20](=[CH:21][CH:22]=[C:23]([C:30](O)=[O:31])[CH:24]=4)[NH:19]3)[CH:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:33][S:34]([NH2:37])(=[O:36])=[O:35]>CN(C)C1C=CN=CC=1.ClCCl>[C:1]([C:5]1[... | CS(N)(=O)=O | CC(C)(C)c1ccc(-c2cc(F)cc(C3Nc4ccc(C(=O)O)cc4CC3(C)C)c2)cc1 | null | CN(C)c1ccncc1 | 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 mixture of 2-(4′-tert-butyl-5-fluoro-biphenyl-3-yl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (30 mg, 0.07 mmol), 1-3-dimethylaminopropyl-3-ethylcarbodiimide hydrochloride (20 mg, 0.10 mmol), 4-dimethylaminopyridine (12.2 mg, 0.10 mmol), methane sulfonamide (20 mg, 0.21 mmol) in dichloromethane (10 ... | CC(C)(C)c1ccc(-c2cc(F)cc(C3Nc4ccc(C(=O)NS(C)(=O)=O)cc4CC3(C)C)c2)cc1 | null | 30.9 | null |
829,463 | ord_dataset-47bd90bf5ec74fcd99ce250a56e18c8f | null | 2008-01-01T00:07:00 | true | [CH3:1][N:2]([CH2:24][C:25]([O:27]C(C)(C)C)=[O:26])[C:3](=[O:23])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[S:13][C:14]3[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=3[C:16](=[O:18])[N:17]=2)[N:7]=1.C(OC(C)C)(C)C>FC(F)(F)C(O)=O>[CH3:1][N:2]([CH2:24][C:25]([OH:27])=[O:26])[C:3](=[O:23])[CH2:4][CH2:5][C:6]1[CH:11]=[C... | CN(CC(=O)OC(C)(C)C)C(=O)CCc1cccc(-c2nc(=O)c3ccccc3s2)n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | CC(C)OC(C)C | null | null | null | null | null | null | null | null | null | 25 | 2.5 | tert-Butyl (methyl{3-[6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]propanoyl}amino)acetate (0.32 g, 0.73 mmol) was dissolved in trifluoroacetic acid (1.0 ml), and the mixture was stirred at room temperature for 2.5 hrs. Isopropyl ether was added to the reaction mixture to precipitate crystals, which were collected by f... | CN(CC(=O)O)C(=O)CCc1cccc(-c2nc(=O)c3ccccc3s2)n1 | null | 89.3 | null |
1,616,044 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [Br:1][C:2]1[CH:3]=[C:4]2[C:10]([CH2:11][C:12]3[CH:13]=[CH:14][C:15]([NH2:19])=[N:16][C:17]=3[F:18])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[F:20][C:21]1[CH:22]=[C:23]([CH:29]=O)[C:24]([O:27][CH3:28])=[N:25][CH:26]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([CH2:11][C:12]3[CH:13]=[CH:14][C:15]([NH:19][... | Nc1ccc(Cc2c[nH]c3ncc(Br)cc23)c(F)n1 | COc1ncc(F)cc1C=O | null | CC[SiH](CC)CC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | 80 | null | To 5-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-6-fluoro-pyridin-2-ylamine (173, 1 equivalent) and 5-fluoro-2-methoxy-pyridine-3-carbaldehyde (37, 1 equivalent), triethylsilane (4 equivalents) and trifluoroacetic acid (4 equivalents) are added. The reaction is stirred at 80° C. for several hours, then concentrated u... | COc1ncc(F)cc1CNc1ccc(Cc2c[nH]c3ncc(Br)cc23)c(F)n1 | null | null | null |
1,463,108 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | C(OC([N:8]1[CH2:12][CH2:11][C@@H:10]([N:13]2[CH2:17][CH2:16][CH2:15][C@@H:14]2[CH3:18])[CH2:9]1)=O)(C)(C)C.[ClH:19]>O1CCOCC1>[ClH:19].[ClH:19].[CH3:18][C@H:14]1[CH2:15][CH2:16][CH2:17][N:13]1[C@@H:10]1[CH2:11][CH2:12][NH:8][CH2:9]1 | C[C@H]1CCCN1[C@@H]1CCN(C(=O)OC(C)(C)C)C1 | 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 | 25 | 20 | A solution of (2S,3′R)-2-methyl-[1,3′]bipyrrolidinyl-1′-carboxylic acid tert-butyl ester (Intermediate (xiii)) (2.51 g, 9.87 mmol) in 1,4-dioxane (9 mL) was chilled to 0° C. and then added 4N HCl in dioxane (6 mL) and allowed to stir for 20 h at ambient temperature. Then the reaction mixture was concentrated to obtain ... | C[C@H]1CCCN1[C@@H]1CCNC1 | null | null | null |
140,262 | ord_dataset-a2a0fbbcd49a46ffaa432d7ceae8a506 | null | 1986-01-01T00:02:00 | true | [CH3:1][O:2][P:3]([O:13]C)([N:5]=[C:6]([S:10][CH2:11][CH3:12])[N:7]([CH3:9])[CH3:8])=[S:4].[CH3:15]I>CO>[CH3:1][O:2][P:3]([S:13][CH3:15])([N:5]=[C:6]([S:10][CH2:11][CH3:12])[N:7]([CH3:9])[CH3:8])=[O:4] | CI | CCSC(=NP(=S)(OC)OC)N(C)C | 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 | null | 6 | A mixture of 36.8 g of N'-(dimethoxyphosphinothioyl)-N,N-dimethylcarbamimidothioic acid, ethyl ester, 120 ml of methanol and 5.0 g of methyl iodide was heated under reflux for 18 hours, then another 5.0 g of methyl iodide was added and heating under reflux was continued for 6 hours. The mixture was concentrated under v... | CCSC(=NP(=O)(OC)SC)N(C)C | null | 263.6 | null |
1,277,064 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[O:3]1.[CH:17]([O:20][CH2:21][CH2:22]O)([CH3:19])[CH3:18]>>[CH:17]([O:20][CH2:21][CH2:22][O:15][C:12]1[CH:13]=[CH:14][C:9]([B:4]2[O:3][C:2]([CH3:16])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]2)=[CH:10][CH:11]=1)([C... | CC(C)OCCO | CC1(C)OB(c2ccc(O)cc2)OC1(C)C | 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 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (609 mg, 2.76 mmol) and ethylene glycol monoisopropyl ether (432 mg, 4.15 mmol), the desired title compound (100 mg, yield 31%) was obtained by the same method as in Example 2 (2a). | CC(C)OCCOc1ccc(B2OC(C)(C)C(C)(C)O2)cc1 | null | 11.8 | null |
924,743 | ord_dataset-cc0899cd744f4f7f8e7f2463560faad1 | null | 2009-01-01T00:12:00 | true | [CH3:1][NH:2][C@H:3]([C:13]([NH:15][C@H:16]([C:21]([N:23]([C@@H:25]([CH:34]([CH3:36])[CH3:35])/[CH:26]=[CH:27]/[S:28]([O:31]CC)(=[O:30])=[O:29])[CH3:24])=[O:22])[C:17]([CH3:20])([CH3:19])[CH3:18])=[O:14])[C:4]([CH3:12])([CH3:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CC(C)=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][N... | CCOS(=O)(=O)/C=C/[C@H](C(C)C)N(C)C(=O)[C@@H](NC(=O)[C@@H](NC)C(C)(C)c1ccccc1)C(C)(C)C | null | null | CCCC[N+](CCCC)(CCCC)CCCC | [I-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | null | null | null | null | null | null | null | null | null | null | 25 | 8 | A solution of N,β,β-trimethyl-L-phenylalanyl-N1-[(1S,2E)-3-(ethoxysulfonyl)-1-isopropylprop-2-enyl]-N1,3-dimethyl-L-valinamide (30 mg, 0.057 mmol) from Example 63 in acetone (1 mL) is treated with tetrabutylammonium iodide (21 mg, 0.057 mmol). The reaction mixture is refluxed for 9 h, and then stirred at room temperatu... | CN[C@H](C(=O)N[C@H](C(=O)N(C)[C@H](/C=C/S(=O)(=O)O)C(C)C)C(C)(C)C)C(C)(C)c1ccccc1 | null | 35.4 | null |
1,084,607 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | [CH2:1]([O:3][C:4]([C:6]1[C:14](=[N+]=[N-])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1)=[O:5])[CH3:2].[CH2:17]([OH:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[O:24][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2... | OCc1ccccc1 | CCOC(=O)C1=Nc2ccccc2C1=[N+]=[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 | React 3-diazo-3H-indole-2-carboxylic acid ethyl ester, 5, (305 mg, 1.4 mmol) with benzyl alcohol (5.0 equiv., 0.73 mL, 7.05 mmol) as described in General Synthetic Procedure VIII to afford 3-benzyloxy-1H-indole-2-carboxylic acid ethyl ester 6 (R1=benzyl) as a white solid [MS obs=296 (M+1)]. Hydrolyze the ester to the c... | CCOC(=O)c1[nH]c2ccccc2c1OCc1ccccc1 | null | null | null |
670,822 | ord_dataset-e90cd41afe844e49875435eb99903799 | null | 2005-01-01T00:05:00 | true | [CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH:26]([NH2:28])[CH3:27])=[C:16]([F:29])[CH:15]=1.C(N(CC)CC)C>>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH:26]([NH:28]... | CC(N)c1ccccc1-c1ccc(Cl)cc1F | COc1ccc(S(=O)(=O)Cl)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from 4-methoxybenzenesulfonyl chloride (331 mg, 1.6 mmol), 1-(4′chloro-2′-fluoro-1,1′-biphenyl-2-yl)ethylamine (400 mg, 1.6 mmol), and triethylamine (246 μL, 1.7 mmol) according to the procedure and in the same manner as described in Example 105, step c resulting in the isolation of 644 ... | COc1ccc(S(=O)(=O)NC(C)c2ccccc2-c2ccc(Cl)cc2F)cc1 | null | null | null |
1,094,127 | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | null | 2011-01-01T00:09:00 | true | [CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:33]([F:36])([F:35])[F:34])=[CH:8][C:9]=2[CH2:11][O:12][CH2:13][C:14]2([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]2)[CH:4]=[N:3]1>FC(F)(F)C(O)=O>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:33]([F:36])([F:35])[F:34])=[CH:8][... | Cn1ncc2cc(C(F)(F)F)cc(COCC3(c4ccccc4)CCN(C(=O)OC(C)(C)C)CC3)c21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | 25 | 0.25 | tert-Butyl 4-(((1-methyl-5-(trifluoromethyl)-1H-indazol-7-yl)methoxy)methyl)-4-phenylpiperidine-1-carboxylate (187 mg, 0.371 mmol) was dissolved in trifluoroacetic acid (25% in dichloromethane, 2 mL) and stirred at room temperature for 15 min. The reaction was concentrated and loaded onto a strong cation exchange cartr... | Cn1ncc2cc(C(F)(F)F)cc(COCC3(c4ccccc4)CCNCC3)c21 | null | null | null |
1,053,303 | ord_dataset-373415d3e0e54004837cf4831e67666f | null | 2011-01-01T00:05:00 | true | C([Li])CCC.CCCCCC.[CH2:12]([C:14]([C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[C:28]([CH3:33])[CH:27]=1)([C:17]1[CH:22]=[CH:21][C:20]([C:23]#[CH:24])=[C:19]([CH3:25])[CH:18]=1)[CH2:15][CH3:16])[CH3:13].[CH3:34][C:35]([CH3:39])([CH3:38])[CH:36]=[O:37].[Cl-].[NH4+]>O1CCCC1>[CH2:12]([C:14]([C:26]1[CH:31]=[CH:30][C:29]([OH:32])=... | CC(C)(C)C=O | C#Cc1ccc(C(CC)(CC)c2ccc(O)c(C)c2)cc1C | 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 | null | 0.5 | A 2.44 M solution of n-butyllithium in hexane (42.8 mL, 104.5 mmol) was added to a solution of 4-[1-ethyl-1-(4-ethynyl-3-methyl-phenyl)-propyl]-2-methyl-phenol (Example 1-(3); 12.22 g, 41.8 mmol) in tetrahydrofuran (300 mL) at 0° C., and the mixture was stirred at the same temperature for 30 minutes. Trimethylacetaldeh... | CCC(CC)(c1ccc(O)c(C)c1)c1ccc(C#CC(O)C(C)(C)C)c(C)c1 | null | 82.7 | null |
1,227,545 | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | null | 2012-01-01T00:11:00 | true | [C:1]([C:5]1[CH:14]=[C:13]2[C:8]([C:9](=[O:15])[CH2:10][CH2:11][O:12]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CS(O)(=O)=O.[N-:21]=[N+]=[N-].[Na+].[OH-].[Na+]>ClCCl>[C:1]([C:5]1[CH:6]=[CH:7][C:8]2[C:9](=[O:15])[NH:21][CH2:10][CH2:11][O:12][C:13]=2[CH:14]=1)([CH3:4])([CH3:3])[CH3:2] | [N-]=[N+]=[N-] | CC(C)(C)c1ccc2c(c1)OCCC2=O | null | CS(=O)(=O)O | [Na+] | [OH-] | 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 | 0 | null | 7-tert-Butyl-chroman-4-one (1.3 g, 6.36 mmol) was taken up in dichloromethane (11.25 mL) and methane sulfonic acid (7.5 mL) and cooled to 0° C. With stirring at 0° C. was added sodium azide (827 mg, 2 eq) portion-wise. The resulting mixture was stirred at 0° C. for 3 hours and by TLC analysis there was no more starting... | CC(C)(C)c1ccc2c(c1)OCCNC2=O | null | null | null |
917,192 | ord_dataset-8e59bd24817446f7b1c68e805b8e5f1d | null | 2009-01-01T00:11:00 | true | [C:1]([O:5][C:6]([N:8]1[C:16]2[CH:15]=[CH:14][N:13]=[CH:12][C:11]=2[CH:10]=[C:9]1[CH2:17][N:18]1[CH2:23][CH2:22][NH:21][CH2:20][C:19]1=[O:24])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:31](Br)[C:32]#[CH:33]>CC#N>[C:1]([O:5][C:6]([N:8]1[C:16]2[CH:15]=[CH:14][N:13]=[CH:12][C:11]=2[CH:10]=[C:9]1[CH2:1... | C#CCBr | CC(C)(C)OC(=O)n1c(CN2CCNCC2=O)cc2cnccc21 | null | O=C([O-])[O-] | [K+] | 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 | 25 | null | A solution containing 2-(2-oxo-piperazin-1-ylmethyl)-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (4.3 g, 13.0 mmol), EXAMPLE 69, in CH3CN (250 mL) is cooled to 0° C. Potassium carbonate (1.98 g, 14.3 mmol) is added to the reaction mixture followed by propargyl bromide (1.55 g, 13.0 mmol). The mixture is s... | C#CCN1CCN(Cc2cc3cnccc3n2C(=O)OC(C)(C)C)C(=O)C1 | null | 70.6 | null |
1,557,597 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [O:1]1[CH:5]=[C:4]([C:6]([OH:8])=O)[N:3]=[CH:2]1.[NH2:9][C@H:10]([CH3:26])[CH2:11][N:12]1[CH:16]=[CH:15][C:14]([C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[C:19]([Cl:25])[CH:18]=2)=[N:13]1>>[Cl:25][C:19]1[CH:18]=[C:17]([C:14]2[CH:15]=[CH:16][N:12]([CH2:11][C@H:10]([NH:9][C:6]([C:4]3[N:3]=[CH:2][O:1][CH:5]=3)=[O:8])[CH3... | C[C@@H](N)Cn1ccc(-c2ccc(C#N)c(Cl)c2)n1 | O=C(O)c1cocn1 | 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 | (R)—N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)oxazole-4-carboxamide was prepared using the method of Example 34(d) starting from 4-oxazolecarboxylic acid (0.202 g, 1.749 mmol) and (R)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (0.4 g, 1.457 mmol). The product was triturated using diet... | C[C@H](Cn1ccc(-c2ccc(C#N)c(Cl)c2)n1)NC(=O)c1cocn1 | null | 45.5 | null |
127,963 | ord_dataset-e61c1950b2fc468dbf0701c65768f73f | null | 1985-01-01T00:03:00 | true | [NH2:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][CH2:9][N:10]1[CH:14]=[CH:13][N:12]=[C:11]1[CH3:15])=[O:5].[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>N1C=CC=CC=1>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([S:27]([NH:1][C:2]2[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=2... | O=S(=O)(Cl)c1ccc(Cl)cc1 | Cc1nccn1CCCNC(=O)c1ccccc1N | 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 | 25 | 4 | 2-Amino-N-[3-(2-methylimidazol-1-yl)propyl]benzamide (10.5 g) was dissolved in pyridine (50 ml) and 4-chlorobenzenesulphonyl chloride (12.35 g) was added in portions during five minutes. The temperature of the reaction mixture rose to 45° C. The solution was stirred at room temperature for 4 hours and the pyridine was ... | Cc1nccn1CCCNC(=O)c1ccccc1NS(=O)(=O)c1ccc(Cl)cc1 | null | null | null |
1,656,990 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [CH3:1][NH:2][S:3]([CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([NH:13][C:14]2[C:19]([N+:20]([O-])=O)=[CH:18][N:17]=[C:16]3[CH:23]=[CH:24][S:25][C:15]=23)[CH2:9][CH2:8]1)(=[O:5])=[O:4]>[Pd].CO>[NH2:20][C:19]1[C:14]([NH:13][C@H:10]2[CH2:9][CH2:8][C@H:7]([CH2:6][S:3]([NH:2][CH3:1])(=[O:5])=[O:4])[CH2:12][CH2:11]2)=[C:15]2[S:2... | CNS(=O)(=O)C[C@H]1CC[C@H](Nc2c([N+](=O)[O-])cnc3ccsc23)CC1 | null | null | [Pd] | 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 | 10 | A mixture of N-methyl-1-{trans-4-[(6-nitrothieno[3,2-b]pyridin-7-yl)amino]cyclohexyl}methanesulfonamide (35 mg, 0.091 mmol) and 10% palladium on carbon (10 mg) in methanol (1.0 mL) was stirred under an atmosphere of H2 for 10 h. The mixture was filtered through Celite. The filtrate was concentrated under reduced pressu... | CNS(=O)(=O)C[C@H]1CC[C@H](Nc2c(N)cnc3ccsc23)CC1 | null | null | null |
359 | ord_dataset-a0eff6fe4b4143f284f0fc5ac503acad | null | 1976-01-01T00:01:00 | true | [CH2:1]([NH:7][NH2:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH3:9][S:10]([C:12]1[S:16][C:15]([N:17]=[C:18]=[O:19])=[N:14][N:13]=1)=[O:11].NN>C(Cl)Cl>[CH2:1]([N:7]([C:18]([NH:17][C:15]1[S:16][C:12]([S:10]([CH3:9])=[O:11])=[N:13][N:14]=1)=[O:19])[NH2:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6] | CCCCCCNN | CS(=O)c1nnc(N=C=O)s1 | null | NN | 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 | 25 | null | A solution of n-hexylhydrazine (0.3 mole) in methylene chloride (150 ml) is charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. 5-Methylsulfinyl-1,3,4-thiadiazol-2-yl isocyanate dimer (0.1 mole) is then added, with stirring, at room temperature. After the addition ... | CCCCCCN(N)C(=O)Nc1nnc(S(C)=O)s1 | null | null | null |
1,550,046 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [O:1]1[C:6]2=[C:7]3[C:12](=[CH:13][CH:14]=[C:5]2[O:4][CH2:3][CH2:2]1)[C:11](O)=[N:10][CH:9]=[CH:8]3.O=P(Cl)(Cl)[Cl:18]>>[Cl:18][C:11]1[C:12]2[C:7](=[C:6]3[O:1][CH2:2][CH2:3][O:4][C:5]3=[CH:14][CH:13]=2)[CH:8]=[CH:9][N:10]=1 | O=P(Cl)(Cl)Cl | Oc1nccc2c3c(ccc12)OCCO3 | 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 solution of 2,3-dihydro-[1,4]dioxino[2,3-f]isoquinolin-7-ol (5 g, 24.61 mmol) in POCl3 (50 mL) was refluxed for 14 h. After Concentration, the residue was taken into the mixture of DCM and 4N NaOH solution. The organic phase was collected and dried over sodium sulfate, filtered, then concentrated under vacuum. The cr... | Clc1nccc2c3c(ccc12)OCCO3 | null | null | null |
1,076,442 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | [F:1][C:2]([F:11])([F:10])[CH:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.[C:12]1([OH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>Cl.CCOC(C)=O.C([O-])(O)=O.[Na+]>[F:1][C:2]([F:11])([F:10])[CH:3]1[CH2:8][CH2:7][C:6]([C:15]2[CH:16]=[CH:17][C:12]([OH:18])=[CH:13][CH:14]=2)([C:15]2[CH:16]=[CH:17][C:12]([OH:18])=[CH:13][CH:14... | O=C1CCC(C(F)(F)F)CC1 | Oc1ccccc1 | null | Cl | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 4-(trifluoromethyl)cyclohexanone (1.13 g, 6.8 mmol) and phenol (2.01 g, 21.4 mmol) in 3 mL of concentrated HCl (aq) was stirred at 40° C. for 18 h. The reaction mixture was diluted with EtOAc and saturated aqueous NaHCO3 was slowly added. The organic layer was collected and the aqueous layer was extracted... | Oc1ccc(C2(c3ccc(O)cc3)CCC(C(F)(F)F)CC2)cc1 | null | null | null |
879,839 | ord_dataset-3592bd645cd143ee8274cd0d834ae581 | null | 2009-01-01T00:05:00 | true | [NH4+:1].[OH-].[Cl:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10](Cl)=[O:11])[CH:5]=1.CC(OC)(C)C>CCOC(C)=O>[Cl:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]([NH2:1])=[O:11])[CH:5]=1 | [NH4+] | O=C(Cl)c1cc(Cl)ccn1 | null | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COC(C)(C)C | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 25 | 2 | Aqueous NH4OH (40%, 250 mL) was added dropwise at 0° C. to a suspension of 4-chloro-pyridine-2-carbonyl chloride (75 g, 533 mmol) in EtOAc. Upon addition, the temperature rose to 30° C. The mixture was stirred for 2 h at RT then kept at RT for 12 h without stirring. MTBE (250 mL) was added to the mixture and the result... | NC(=O)c1cc(Cl)ccn1 | null | null | null |
1,010,636 | ord_dataset-7448b89163bf426c9d9777809ce24cec | null | 2010-01-01T00:11:00 | true | Cl[S:2]([C:5]1[O:9][C:8]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[C:14]([NH2:18])([CH3:17])([CH3:16])[CH3:15]>C(Cl)Cl>[C:14]([NH:18][S:2]([C:5]1[O:9][C:8]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:6]=1)(=[O:4])=[O:3])([CH3:17])([CH3:16])[CH3:15] | COC(=O)c1ccc(S(=O)(=O)Cl)o1 | CC(C)(C)N | 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 | 25 | 48 | To a solution of methyl 5-(chlorosulfonyl)-2-furoate (3.0 g) in DCM (100 mL) was added tert-butylamine (3.6 mL). After stirring at room temperature for 2 days the mixture was filtered through a pad of celite, washing with DCM (2×10 mL). The filtrate was evaporated to dryness in vacuo. The resulting crude residue was pu... | COC(=O)c1ccc(S(=O)(=O)NC(C)(C)C)o1 | null | null | null |
1,528,332 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | CO[C:3]([C:5]1[N:6]=[C:7]([C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[C:8]2[C:9](=[O:23])[N:10]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:11]=[CH:12][C:13]=2[C:14]=1[OH:15])=[O:4].[NH2:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34].C[O-].[Na+]>>[CH2:16]([N:10]1[C:9](=[O:23])[C:8]2[C:7]([C:24]3[CH:25]=[N:... | COC(=O)c1nc(-c2cccnc2)c2c(=O)n(Cc3ccccc3)ccc2c1O | NCCC(=O)O | null | C[O-] | [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 | 25 | null | A mixture of 7-benzyl-4-hydroxy-8-oxo-1-pyridin-3-yl-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl ester (24 mg, 0.062 mmol), β-alanine (552 mg, 6.2 mmol) and NaOMe solution (10 mL, 5.0 mmol, 0.5 M in MeOH) was refluxed for 16 h. After the mixture was cooled to r.t., solvent was evaporated in vacuo. The resid... | O=C(O)CCNC(=O)c1nc(-c2cccnc2)c2c(=O)n(Cc3ccccc3)ccc2c1O | null | 43.5 | null |
1,660,611 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH:6]([CH2:9][NH:10][C:11]2[N:19]=[CH:18][N:17]=[C:16]3[C:12]=2[N:13]=[C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[Cl:33])[N:15]3[C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[CH2:5][CH2:4]1.[S:34](N)([NH2:37])(=[O:36])=[O:35]>O1CCOCC1>[Cl:33][C:28]1[CH:29]=[CH:30][C... | NCC1CCC(CNc2ncnc3c2nc(-c2ccccc2Cl)n3-c2ccc(Cl)cc2)CC1 | NS(N)(=O)=O | null | null | 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 | 80 | 16 | To a solution of N-{[4-(aminomethyl)cyclohexyl]methyl}-8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-amine (6.6 mg, 0.014 mmol, 1 eq.) in 5 mL of dioxane was added 10 mg of sulfamide. The reaction was heated to 80° C. and stirred 16 h. The reaction was concentrated in vacuo. The crude material was purified by silica... | O=[SH](=O)NNCC1CCC(CNc2ncnc3c2nc(-c2ccccc2Cl)n3-c2ccc(Cl)cc2)CC1 | null | 24.2 | null |
1,595,173 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[NH:15][C:16]1[N:21]=[C:20](Cl)[C:19]2[C:23](=[O:33])[N:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:25][C:18]=2[C:17]=1[F:34])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Sn](CCCC)(CCCC)[C:40]1[S:44][N:43]=[CH:42][CH:41]=1)CCC.O>C1(C)C=... | CCCC[Sn](CCCC)(CCCC)c1ccns1 | CC(C)(C)OC(=O)N[C@H]1CCCC[C@H]1Nc1nc(Cl)c2c(c1F)CN(C(=O)OC(C)(C)C)C2=O | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | A solution of tert-butyl 6-((1R,2S)-2-(tert-butoxycarbonylamino)cyclohexylamino)-4-chloro-7-fluoro-3-oxo-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate (60 mg, 0.120 mmol), 5-(tributylstannyl)isothiazole (67.5 mg, 0.180 mmol) and tetrakis(triphenylphosphine)palladium(0) (69.5 mg, 0.060 mmol) in toluene (2.0 mL) was heated... | CC(C)(C)OC(=O)N[C@H]1CCCC[C@H]1Nc1nc(-c2ccns2)c2c(c1F)CN(C(=O)OC(C)(C)C)C2=O | null | null | null |
832,275 | ord_dataset-47bd90bf5ec74fcd99ce250a56e18c8f | null | 2008-01-01T00:07:00 | true | [CH2:1]([NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[C:2]#[CH:3].I[C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=1>>[C:7]([O:6][C:5](=[O:11])[NH:4][CH2:1][C:2]#[C:3][C:13]1[CH:14]=[CH:15][C:16]([O:19][C:20]([F:21])([F:22])[F:23])=[CH:17][CH:18]=1)([CH3:8])([CH3:10])[CH3:9] | FC(F)(F)Oc1ccc(I)cc1 | C#CCNC(=O)OC(C)(C)C | 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 example 8 a], tert-butyl 2-propynylcarbamate was reacted with 1-iodo-4-trifluoromethoxy-benzene in the presence of PdCl2(Ph3P)2 and cuprous iodide to give the title compound as yellow crystals. | CC(C)(C)OC(=O)NCC#Cc1ccc(OC(F)(F)F)cc1 | null | null | null |
330,340 | ord_dataset-2c460e2ef9934444aaf26fec1f75741f | null | 1996-01-01T00:05:00 | true | [Cl:1][C:2]1[C:7]2[C:8](=[O:13])[C:9]([CH3:12])([CH3:11])[O:10][C:6]=2[C:5]([N+:14]([O-])=O)=[CH:4][CH:3]=1>C(O)(=O)C.O.[Fe]>[NH2:14][C:5]1[C:6]2[O:10][C:9]([CH3:11])([CH3:12])[C:8](=[O:13])[C:7]=2[C:2]([Cl:1])=[CH:3][CH:4]=1 | CC1(C)Oc2c([N+](=O)[O-])ccc(Cl)c2C1=O | null | null | [Fe] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | O | null | null | null | null | null | null | null | null | null | null | null | By the method of Example 1, Step E, 4.82 g (0.020 mole) of 4-chloro-2,3-dihydro-2,2-dimethyl-7-nitrobenzofuran-3-one and 5.0 g of powdered iron were reacted in 80 mL of glacial acetic acid and 10 mL of water, yielding 3.25 g of 7-amino-4-chloro-2,3-dihydro-2,2-dimethylbenzofuran-3-one as an oil which subsequently solid... | CC1(C)Oc2c(N)ccc(Cl)c2C1=O | null | 76.8 | null |
949,373 | ord_dataset-3feb2a95f66e4706a4a50c977ccd9bf8 | null | 2010-01-01T00:04:00 | true | O[CH:2]=[C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:23])[CH3:22])=[CH:16][CH:15]=3)=[O:13])=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:24].[NH2:25][C:26]1[CH:27]=[C:28]([OH:32])[CH:29]=[CH:30][CH:31]=1>C1COCC1>[OH:32][C:28]1[CH:27]=[C:26]([NH:25][CH:2]=[C:3]2[C:11]3[C:6](=[CH:7][C:8]([C:1... | CC(=O)Nc1ccc(C(=O)c2ccc3c(c2)NC(=O)C3=CO)cc1 | Nc1cccc(O)c1 | 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 | 65 | 24 | A small screw cap test tube was charged with N-[4-(3-Hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-acetamide (as prepared in Example 29, 70 mg, 0.217 mmol) and THF (2 mL). To the resulting solution was added 3-aminophenol (28 mg, 0.257 mmol), and the mixture was stirred for 24 h at 65° C. Subsequentl... | CC(=O)Nc1ccc(C(=O)c2ccc3c(c2)NC(=O)C3=CNc2cccc(O)c2)cc1 | null | 76 | null |
1,373,583 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | [O:1]=[S:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][N:5]([C:13]2[N:18]=[C:17]([NH:19][C@H:20]3[C@H:24]([F:25])[CH2:23][N:22](C(OCC4C=CC=CC=4)=O)[CH2:21]3)[C:16]3[S:36][C:37]([CH3:39])=[CH:38][C:15]=3[N:14]=2)[CH2:4][CH2:3]1.[OH-].[K+]>CO>[F:25][C@@H:24]1[CH2:23][NH:22][CH2:21][C@H:20]1[NH:19][C:17]1[C:16]2[S:... | Cc1cc2nc(N3CCS(=O)c4ccccc4C3)nc(N[C@@H]3CN(C(=O)OCc4ccccc4)C[C@H]3F)c2s1 | null | null | [K+] | [OH-] | 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 | To a suspension of benzyl trans-(±)-3-{[2-(1-oxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylthienopyrimidin-4-yl]amino}-4-fluoropyrrolidine-1-carboxylate (320 mg, 0.57 mmol) in methanol (5 mL) was added an aqueous solution of potassium hydroxide (40%, 5 mL). The suspension was heated under reflux for 30 minutes... | Cc1cc2nc(N3CCS(=O)c4ccccc4C3)nc(N[C@@H]3CNC[C@H]3F)c2s1 | null | null | null |
296,370 | ord_dataset-ec7cb3d5a8704f64b01d401ea555974f | null | 1994-01-01T00:09:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][C:3]=1[OH:15].Cl[CH2:17][CH2:18][NH:19][C:20](=[O:24])[O:21][CH2:22][CH3:23].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][C:3]=1[O:15][CH2:17][CH2:18]... | Oc1cc(Oc2ccccc2)ccc1Cl | CCOC(=O)NCCCl | 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 | 0 | null | To a solution of 0.91 g of 2-chloro-5-phenoxyphenol in 20 ml of N,N-dimethylformamide, there were added 0.69 g of ethyl 2-chloroethylcarbamate and 1.14 g of potassium carbonate with stirring, and the resultant mixture was stirred at 50° C. for 7 hours. The reaction mixture was poured into 100 g of ice-water and extract... | CCOC(=O)NCCOc1cc(Oc2ccccc2)ccc1Cl | null | 10.1 | null |
1,543,502 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [CH3:1][C:2]1[O:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][C:3]=1[C:11]1[N:15]([CH3:16])[N:14]=[CH:13][CH:12]=1.[Br:17]N1C(=O)CCC1=O>O1CCCC1>[Br:17][C:12]1[CH:13]=[N:14][N:15]([CH3:16])[C:11]=1[C:3]1[CH:4]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[O:6][C:2]=1[CH3:1] | O=C1CCC(=O)N1Br | COC(=O)c1cc(-c2ccnn2C)c(C)o1 | 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 | null | null | A solution of methyl 5-methyl-4-(1-methyl-1H-pyrazol-5-yl)-2-furancarboxylate (600 mg, 2.72 mmol) [prepared in Example 116] and N-bromosuccinimide (485 mg, 2.72 mmol) in tetrahydrofuran (13 ml) was stirred in a sealed tube for 1 h at 70° C. The reaction mixture was divided and half of the solution was partitioned betwe... | COC(=O)c1cc(-c2c(Br)cnn2C)c(C)o1 | null | 15.1 | null |
612,487 | ord_dataset-5c4ee54447b84205a10f9c0473172972 | null | 2003-01-01T00:10:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH:10]=1)[C:5]([OH:7])=O.C(N(CC)CC)C.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.[CH2:41]([NH:44][CH:45]1[CH2:49][CH2:48][CH2:47][CH2:46]1)[CH:42]=[CH2:43]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]([N:44]([CH:45]2[CH2:49][CH2:48][... | C=CCNC1CCCC1 | CC(C)(C)[Si](C)(C)Oc1cc(Cl)cc(C(=O)O)c1 | null | O=C1OCCN1P(=O)(Cl)N1CCOC1=O | 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 | null | 0.08 | To a solution of 3-chloro-5-(tert-butyldimethylsilyloxy)benzoic acid (17.5 g, 60 mmol), as prepared in the preceding step, and CH2Cl2 (250 mL) were added triethylamine (33.8 mL, 0.24 mol) and bis(2-oxo-3-oxazolidinyl)phosphinic chloride (17.0 g, 66 mmol). The resulting mixture was stirred for 5 min, then N-allylcyclope... | C=CCN(C(=O)c1cc(Cl)cc(O[Si](C)(C)C(C)(C)C)c1)C1CCCC1 | null | 99.4 | null |
539,432 | ord_dataset-49124ff635234889bd8dcfe87f4f9013 | null | 2002-01-01T00:04:00 | true | Cl[C:2]1[CH:3]=[C:4](C#C)[C:5]2[O:9][C:8]([CH2:10][C:11]3C=C(C(C)(C)C)C(O)=C(C(C)(C)C)C=3)=[N:7][C:6]=2[CH:26]=1.Br[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=1>C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[N:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[C:... | C#Cc1cc(Cl)cc2nc(Cc3cc(C(C)(C)C)c(O)c(C(C)(C)C)c3)oc12 | Brc1ccccn1 | null | Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1 | [Cu]I | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | null | A suspension of 5-chloro-2-(3,5-di-t-butyl-4-hydroxy-benzyl)-7-ethynyl-benzoxazole (2.38 g, 6.0 mmol), 2-bromo-pyridine (0.66 ml, 98%, 6.6 mmol), bis(triphenylphosphine)palladium(II) dichloride (21.1 mg, 30 μmol) and copper (I) iodide (1.2 mg, 6 μmol) in triethylamine (12 ml) was heated at 90EC, under argon, for 1.5 ho... | C#Cc1nc2c(-c3ccccn3)cccc2o1 | null | 224 | null |
1,569,730 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | [CH2:1]([O:3][C:4](=[O:25])[C:5]1[CH:10]=[C:9]([S:11][C:12]2[C:20]3[C:15](=[C:16]([F:22])[C:17]([Cl:21])=[CH:18][CH:19]=3)[NH:14][C:13]=2[CH3:23])[CH:8]=[CH:7][C:6]=1[CH3:24])[CH3:2].Br[C:27]1[CH:28]=[N:29][N:30]([CH2:32][CH3:33])[CH:31]=1>>[CH2:1]([O:3][C:4](=[O:25])[C:5]1[CH:10]=[C:9]([S:11][C:12]2[C:20]3[C:15](=[C:1... | CCOC(=O)c1cc(Sc2c(C)[nH]c3c(F)c(Cl)ccc23)ccc1C | CCn1cc(Br)cn1 | 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 55, Step 2 using the following starting materials: 5-(6-Chloro-7-fluoro-2-methyl-1H-indol-3-ylsulfanyl)-2-methyl-benzoic acid ethyl ester and 4-bromo-1-ethyl-1H-pyrazole. | CCOC(=O)c1cc(Sc2c(C)n(-c3cnn(CC)c3)c3c(F)c(Cl)ccc23)ccc1C | null | null | null |
1,581,536 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | [OH:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.Br[C:12]1[C:13]2[N:14]([CH:18]=[C:19]([CH3:21])[N:20]=2)[CH:15]=[CH:16][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+].COCCOC>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=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=... | OB(O)c1ccc(O)cc1 | Cc1cn2cccc(Br)c2n1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | COCCOC | null | null | null | null | null | null | null | null | null | null | null | A mixture of 4-hydroxyphenylboronic acid (1.1 g), 8-bromo-2-methylimidazo[1,2-a]pyridine (1.7 g), tetrakis(triphenylphosphine)palladium(0) (0.28 g), sodium carbonate (3.0 g), DME (35 ml) and water (7 ml) was heated under reflux overnight under an argon atmosphere. The reaction mixture was poured into water, and the mix... | Cc1cn2cccc(-c3ccc(O)cc3)c2n1 | null | 25.7 | null |
845,539 | ord_dataset-e2b35e721c2741999b0005d12691f9fe | null | 2008-01-01T00:10:00 | true | [CH2:1]([O:8][C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>O1CCCC1>[S:25]([O:12][CH2:11][C:10]1[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)(=[O:27])(=[O:26])[CH3:24] | CS(=O)(=O)Cl | OCc1ccccc1OCc1ccccc1 | null | null | 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 | 25 | 0.5 | To a solution of 2-benzyloxybenzyl alcohol (2.1 g, 9.42 mmol) in tetrahydrofuran (10 mL), triethylamine (1.38 mL, 9.89 mmol) and methanesulfonyl chloride (0.766 mL, 9.89 mmol) were added under ice cooling and stirred at room temperature for 30 minutes. After filtration to remove the insoluble materials, the filtrate wa... | CS(=O)(=O)OCc1ccccc1OCc1ccccc1 | null | 117.6 | null |
728,446 | ord_dataset-eb4226b4f7644a01a737e7547b70014a | null | 2006-01-01T00:09:00 | true | [C:1]1([C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8](O)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:23][CH2:24][CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][CH:30]([C:33]2[CH:34]=[C:35]([NH:39][C:40](=[O:44])[CH:41]([CH3:43])[CH3:42])[CH:36]=[CH:37][CH:38]=2)[CH2... | CC(C)C(=O)Nc1cccc(C2CCN(CCCN)CC2)c1 | O=C(O)C(c1ccccc1)(c1ccccc1)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | Example 59 was prepared from triphenylacetic acid and N-{3-[1-(3-aminopropyl)-4-piperidinyl]phenyl}-2-methylpropanamide according to the procedures described in Scheme 9: 1H NMR (400 MHz, CDCl3) δ 7.40 (d, 2H, J=10.8 Hz), 7.32–7.17 (m, 17H), 6.87 (d, 1H, J=7.7 Hz), 6.32–6.26 (m, 1H), 3.41 (q, 2H, J=6.0 Hz), 2.83 (d, 2H... | CC(C)C(=O)Nc1cccc(C2CCN(CCCNC(=O)C(c3ccccc3)(c3ccccc3)c3ccccc3)CC2)c1 | null | null | null |
26,098 | ord_dataset-2ada3fda46fc44719ba0c8001f53c1b3 | null | 1977-01-01T00:06:00 | true | [CH2:1]([N:3]1[C:7](=[O:8])[CH2:6][S:5][C:4]1=[S:9])[CH3:2].Cl([O-])(=O)(=O)=O.[Cl:15][C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18](=[CH:25]N(C)C)[N+:17]=1[CH2:29][CH3:30]>C(N(CC)CC)C>[Cl:15][C:16]1[N:17]([CH2:29][CH3:30])[C:18]([CH:25]=[C:6]2[S:5][C:4](=[S:9])[N:3]([CH2:1][CH3:2])[C:7]2=[O:8])=[C:19]2[C... | CCN1C(=O)CSC1=S | CC[N+]1=C(Cl)c2ccccc2C1=CN(C)C | null | [O-][Cl+3]([O-])([O-])[O-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | null | This dye was prepared by the interaction of 3-ethyl-rhodanine and 3-chloro-1-dimethylaminomethylene-2-ethyl-1H-isoindolium perchlorate in the presence of triethylamine. The dye after purification by recrystallization from methanol melted at 119° C. MeOH λ max 505 nm. | CCN1C(=O)C(=Cc2c3ccccc3c(Cl)n2CC)SC1=S | null | null | null |
1,519,585 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | [C:1]([C:5]1[CH:6]=[C:7]([NH:17][C:18]([NH:20][C@@H:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C@H:24]([O:31][C:32]3[CH:33]=[CH:34][C:35]4[N:36]([C:38]([N:41]5[CH2:45][CH2:44][CH:43]([O:46][Si](C(C)C)(C(C)C)C(C)C)[C@@H:42]5[CH3:57])=[N:39][N:40]=4)[CH:37]=3)[CH2:23][CH2:22]2)=[O:19])[N:8]([C:10]2[CH:15]=[CH:14... | Cc1ccc(-n2nc(C(C)(C)C)cc2NC(=O)N[C@H]2CC[C@@H](Oc3ccc4nnc(N5CCC(O[Si](C(C)C)(C(C)C)C(C)C)[C@@H]5C)n4c3)c3ccccc32)cc1 | null | null | CCCC[N+](CCCC)(CCCC)CCCC | [F-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | O | null | null | null | null | null | null | null | null | null | null | null | To a solution of Intermediate 92d (240 mg, 0.300 mmol) and TBAF (1M in THF, 0.400 mL, 0.400 mmol) in THF (3 mL) was stirred at RT for 1 h. Water was added and the mixture extracted with DCM (4×20 mL). The combined organics were dried and concentrated in vacuo. The residue was purified by FCC, using 0-14% MeOH in DCM, t... | Cc1ccc(-n2nc(C(C)(C)C)cc2NC(=O)N[C@H]2CC[C@@H](Oc3ccc4nnc(N5CC[C@H](CO)C5)n4c3)c3ccccc32)cc1 | null | null | null |
1,410,408 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | [C:1]1([SH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Cl[C:13]1[S:17][C:16]([C:18](=[O:20])[CH3:19])=[CH:15][C:14]=1[N+:21]([O-:23])=[O:22]>>[C:1]1([S:11][C:13]2[S:17][C:16]([C:18](=[O:20])[CH3:19])=[CH:15][C:14]=2[N+:21]([O-:23])=[O:22])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C... | Sc1cccc2ccccc12 | CC(=O)c1cc([N+](=O)[O-])c(Cl)s1 | 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 as in Step B for example 1 from 1-naphthalenethiol (320 mg, 2 mmol) and 1-(5-Chloro-4-nitro-2-thienyl)ethanone (412 mg, 2 mmol) to afforded the title compound as a yellow solid (192 mg, 29% yield). 1H NMR (300 MHz, CDCl3) δ: 8.33 (1H, m), 8.11 (1H, m), 8.08 (1H, s), 7.98 (2... | CC(=O)c1cc([N+](=O)[O-])c(Sc2cccc3ccccc23)s1 | null | 29.1 | null |
1,589,120 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [NH2:1][C@@H:2]([CH2:6][CH2:7][CH2:8][NH:9][C:10]([NH:12][S:13]([C:16]1[C:17]([CH3:29])=[C:18]([CH3:28])[C:19]2[O:23][C:22]([CH3:25])([CH3:24])[CH2:21][C:20]=2[C:26]=1[CH3:27])(=[O:15])=[O:14])=[NH:11])[C:3]([OH:5])=[O:4].[C:30](OC(=O)C)(=[O:32])[CH3:31]>N1C=CC=CC=1>[C:30]([NH:1][C@@H:2]([CH2:6][CH2:7][CH2:8][NH:9][C:1... | CC(=O)OC(C)=O | Cc1c(C)c(S(=O)(=O)NC(=N)NCCC[C@H](N)C(=O)O)c(C)c2c1OC(C)(C)C2 | 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 | (S)-2-Amino-5-(3-(2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-ylsulfonyl) guanidino)pentanoic acid (H-L-Arg(Pbf)-OH) (1.0 eq.) is dissolved in pyridine (0.25 M) and acetic anhydride (1.2 eq.) is added to acylate the primary amine, after 1 h the reaction is quenched with aqueous acid, extracted with ethyl acetate, and... | CC(=O)N[C@@H](CCCNC(=N)NS(=O)(=O)c1c(C)c(C)c2c(c1C)CC(C)(C)O2)C(=O)O | null | null | null |
1,680,538 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | [N:1]1([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]2[C:18]([O:19][CH3:20])=[N:17][C:16]3[C:11]2=[N:12][C:13]([O:22][CH2:23][CH2:24][CH2:25][CH3:26])=[N:14][C:15]=3[NH2:21])[CH2:4][CH2:3][CH2:2]1.[CH2:27](OC1N=C2C(N=C(OC)N2CCCCCCl)=C(N)N=1)CCC.N1CCCC1>>[CH2:23]([O:22][C:13]1[N:12]=[C:11]2[C:16]([N:17]=[C:18]([O:19][CH3:20]... | CCCCOc1nc(N)c2nc(OC)n(CCCCCN3CCC3)c2n1 | CCCCOc1nc(N)c2nc(OC)n(CCCCCCl)c2n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCNC1 | null | null | null | null | null | null | null | null | null | null | null | null | Prepared similarly to Intermediate 27 from 2-(butyloxy)-9-(5-chloropentyl)-8-(methyloxy)-9H-purin-6-amine and pyrrolidine. | CCCCOc1nc(N)c2nc(OC)n(CCCCCN3CCCC3)c2n1 | null | null | null |
693,756 | ord_dataset-35824232b132464aa99e71aba765981d | null | 2005-01-01T00:12:00 | true | [CH3:1][S:2]([N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7](C=O)=[CH:6]1)(=[O:4])=[O:3].ClC1C=CC=C(C(OO)=[O:24])C=1>ClCCl>[CH3:1][S:2]([N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7](=[O:24])[CH2:6]1)(=[O:4])=[O:3] | O=C(OO)c1cccc(Cl)c1 | CS(=O)(=O)n1cc(C=O)c2cccnc21 | 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 | 0 | 8 | 1-Methanesulfonyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (2.84 g, 12.7 mmol) from step 2 was dissolved in dichloromethane (150 ml) and cooled to 0° C. Meta-chloroperbenzoic acid (3.4 g, 15 mmol) was added in several portions. The reaction mixture was stirred under a nitrogen atmosphere overnight, while slowly warming... | CS(=O)(=O)N1CC(=O)c2cccnc21 | null | 26 | null |
648,369 | ord_dataset-5d77a731aa10488794c824ad12021f57 | null | 2004-01-01T00:09:00 | true | [CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]=[C:10]=[O:11].[CH3:12][C:13]1[S:14][C:15]([C:18]([NH:20][NH2:21])=[O:19])=[CH:16][N:17]=1>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:11])[NH:21][NH:20][C:18]([C:15]1[S:14][C:13]([CH3:12])=[N:17][CH:16]=1)=[O:19] | Cc1ncc(C(=O)NN)s1 | Cc1ccc(N=C=O)c(C)c1 | 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 | 25 | 2 | The title compound was prepared from a mixture 2,4-dimethylphenylisocyanate (50 mg, 0.34 mmol) and 2-methylthiazole-5-carboxylic acid hydrazide (59 mg, 0.37 mmol) in methylenedichloride (10 mL). The mixture was stirred at room temperature for 2 h, and the resultant precipitate was collected by filtration and isolated a... | Cc1ccc(NC(=O)NNC(=O)c2cnc(C)s2)c(C)c1 | null | null | null |
1,320,017 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | C([O:8][C:9]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][N:37]([CH2:40][CH3:41])[CH2:38][CH3:39])=[CH:30][C:10]=1[C:11]([NH:13][C:14]1[CH:23]=[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:21]=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17])=[O:12])C1C=CC=CC=1>CO.C(OCC)(=O)C.[C].[Pd]>[CH2:40]([N:37]([CH2:38][C... | CCN(CC)CCOc1ccc(OCc2ccccc2)c(C(=O)Nc2cc(-c3ccccc3)ccc2C(=O)OC)c1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 25 | 3 | To a solution mixture of the obtained methyl 2-(2-(benzyloxy)-5-(2-(diethylamino)ethoxy)benzamido)-4-phenylbenzoate (0.15 g) in methanol (3.0 mL) and ethyl acetate (3.0 mL), 10% palladium-carbon (0.030 g) was added, followed by stirring under a hydrogen atmosphere at room temperature for 3 hours. The insoluble substanc... | CCN(CC)CCOc1ccc(O)c(C(=O)Nc2cc(-c3ccccc3)ccc2C(=O)OC)c1 | null | 69.3 | null |
605,751 | ord_dataset-273fda773e864aaf9b71a30a2d9f2162 | null | 2003-01-01T00:08:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([OH:23])=O)[CH:6]=[CH:7][C:8]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19])=[O:11].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[NH:57]1[C:65]2[C:60](=[CH:61][C:62]([CH:66]([CH3:73])[CH2:67][C:68]([O:70][CH2:71][CH... | CCOC(=O)CC(C)c1ccc2c(c1)CCN2 | COc1cc(CC(=O)O)ccc1NC(=O)Nc1ccccc1C | null | CN(C)C(On1nnc2cccnc21)=[N+](C)C | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | null | 1 | A solution of [3-methoxy-4-(3-o-tolyl-ureido)-phenyl]-acetic acid (2.9 g) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (3.7 g) in dimethylformamide (about 40 ml) was treated with diisopropylethylamine (10 ml), followed after about 30 seconds by a solution of (R/S) ethyl 3-(2,3-dihydro... | CCOC(=O)CC(C)c1ccc2c(c1)CCN2C(=O)Cc1ccc(NC(=O)Nc2ccccc2C)c(OC)c1 | null | 57.3 | null |
520,918 | ord_dataset-262b40ea420c471da9b9244fe9b8f645 | null | 2001-01-01T00:10:00 | true | [CH3:1][C:2]([NH:7][S:8]([C:11]1[S:12][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[CH:14][CH:15]=1)(=[O:10])=[O:9])([CH3:6])[C:3]([OH:5])=O.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.Cl.[CH3:57][Si:58]([CH3:64])([CH3:63])[CH2:59][CH2:60][O:61][NH2:62]>C(Cl)Cl>[CH3:6][C:2]([NH:7... | CC(C)(NS(=O)(=O)c1ccc(-c2ccccn2)s1)C(=O)O | C[Si](C)(C)CCON | null | CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C | Cl | F[P-](F)(F)(F)(F)F | 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 | 16 | To a solution of 2-methyl-2-(5-pyridin-2-ylthiophene-2-sulfonylamino)-propionic acid (1.60 grams, 4.91 mmole) in methylene chloride (160 mL) was added triethylamine (2.3 mL, 16.5 mmole), (benzotriazol-1-yloxy)tris(dimethylamino)-phosphonium hexafluorophosphate (2.4 grams, 5.41 mmole) and O-(2-trimethylsilylethyl)hydrox... | CC(C)(NS(=O)(=O)c1ccc(-c2ccccn2)s1)C(=O)NOCC[Si](C)(C)C | null | 10.1 | null |
586,983 | ord_dataset-cb5dd7a8b94e4f19a9148a1904b0dcb6 | null | 2003-01-01T00:03:00 | true | [CH2:1]([O:3][C:4]([CH2:6][O:7][C:8]1[C:13]([N+:14]([O-])=O)=[CH:12][CH:11]=[CH:10][N:9]=1)=[O:5])[CH3:2]>[Pd].C(OCC)(=O)C>[NH2:14][C:13]1[C:8]([O:7][CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])=[N:9][CH:10]=[CH:11][CH:12]=1 | CCOC(=O)COc1ncccc1[N+](=O)[O-] | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | 25 | 3 | A mixture of 48.3 g of 2-(ethoxycarbonyl)methoxy-3-nitropyridine, 7.8 g of 10% palladium/carbon and 540 ml of ethyl acetate was stirred for 3 hours at room temperature under hydrogen atmosphere. The reaction system was purged with nitrogen, then, the reaction solution was filtrated through Celite, and the filtrate was ... | CCOC(=O)COc1ncccc1N | null | 88.5 | null |
984,148 | ord_dataset-35b56288528641309a040cc2b6710b61 | null | 2010-01-01T00:08:00 | true | [F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([O:19][CH3:20])=[O:18])[CH:15]=3)[NH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Cl[C:24]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)([O-])O.[... | ClC(c1ccccc1)(c1ccccc1)c1ccccc1 | COC(=O)c1ccc2[nH]nc(-c3cccc(F)c3)c2c1 | null | O=C([O-])O | [H-] | [Na+] | 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 | To a solution of 2.43 g of methyl 3-(3-fluorophenyl)-1H-5-indazolecarboxylate produced in Production Example I-4-e in 25 ml tetrahydrofuran was added 720 mg of 60% sodium hydride (oily), and the mixture was stirred under ice-cooling for 10 minutes. Then, 3.26 g of chlorotriphenylmethane was added and the mixture was st... | COC(=O)c1ccc2c(c1)c(-c1cccc(F)c1)nn2C(c1ccccc1)(c1ccccc1)c1ccccc1 | null | 75.5 | null |
224,190 | ord_dataset-1d5bba1436bd42b7a27c43833c25d871 | null | 1991-01-01T00:03:00 | true | [C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[CH2:18][C:19]([C:21]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:22]=1[N:23]([CH3:26])[CH:24]=[O:25])=[O:20]>ClCCl>[C:1]([O:9][CH2:18][C:19]([C:21]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:22]=1[N:23]([CH3:26])[CH:24]=[O:25])=[O:20])(=[O:8])[C:... | Cc1ccc(C(=O)CCl)c(N(C)C=O)c1 | O=C(O)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | ClCCl | null | null | null | null | null | null | null | null | null | 25 | null | A solution of benzoic acid (30.3 g) and triethylamine (50.1 ml) in dichloromethane (150 ml) was added dropwise at 0° over a period of 15 minutes to the solution of 2'-(2-chloroacetyl)-5'-methyl-N-methylformanilide obtained above. The resultant solution was allowed to warm to ambient temperature and then heated under re... | Cc1ccc(C(=O)COC(=O)c2ccccc2)c(N(C)C=O)c1 | null | null | null |
173,571 | ord_dataset-3844acbccc714c04ab757ec4fca10bd0 | null | 1988-01-01T00:06:00 | true | [O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][O:5][C:4]2[CH:13]=[CH:14][C:15]([CH2:17][CH2:18][OH:19])=[CH:16][C:3]1=2.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>N1C=CC=CC=1>[CH3:20][S:21]([O:19][CH2:18][CH2:17][C:15]1[CH:14]=[CH:13][C:4]2[O:5][CH2:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:2](=[O:1])[C:3]=... | O=C1c2ccccc2COc2ccc(CCO)cc21 | CS(=O)(=O)Cl | 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 | 0.25 | A stirred chilled (-5° C.) solution of 2-(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)ethanol (5.08 g, 0.02 mol) and anhydrous pyridine (28 ml) was treated over 60 seconds with methanesulfonyl chloride (2.74 g, 0.024 mol). A mild exotherm was noted and a precipitate separated with continued cooling and stirring for 15 mi... | CS(=O)(=O)OCCc1ccc2c(c1)C(=O)c1ccccc1CO2 | null | 39.1 | null |
197,230 | ord_dataset-f6fafbb8ce5f4ef099be3a772075ec97 | null | 1989-01-01T00:10:00 | true | [CH:1]1([NH:4][C:5](=S)[NH:6][NH2:7])[CH2:3][CH2:2]1.[Cl:9][CH:10]([C:16]([CH3:18])=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12]>Cl>[ClH:9].[CH:1]1([NH:4][C:5]2[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:16]([CH3:18])[NH:7][N:6]=2)[CH2:3][CH2:2]1 | CCOC(=O)C(Cl)C(C)=O | NNC(=S)NC1CC1 | 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 | 25 | 1 | A stirred slurry of 10.4 g (0.079 mole) of 4-cyclopropyl-3-thiosemicarbazide under nitrogen atmosphere was treated with 13 g (0.079 mole) of ethyl 2-chloroacetoacetate, stirred at ambient temperature for 1 hr, treated with 30 mL of 2N ethanolic hydrogen chloride and heated to reflux. The reaction mixture was allowed to... | CCOC(=O)c1c(NC2CC2)n[nH]c1C | null | 30.9 | null |
131,541 | ord_dataset-7724d657b6fc42848b62ca7c93d84bed | null | 1985-01-01T00:06:00 | true | [CH3:1][C:2]1[NH:3][C:4]([CH:28]([O:32][CH2:33][CH3:34])[O:29][CH2:30][CH3:31])=[C:5]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:6]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:7]=1[C:8]([O:10][CH2:11][CH2:12]Cl)=[O:9].[CH2:35]([NH:37][CH2:38][CH3:39])[CH3:36]>C(O)CC.[I-].[Na+]>[CH3:1][C:2]1... | CCNCC | CCOC(=O)C1=C(C(OCC)OCC)NC(C)=C(C(=O)OCCCl)C1c1cccc([N+](=O)[O-])c1 | null | [I-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCO | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 2-chloroethyl 2-methyl-4-(3-nitrophenyl)-5-ethoxycarbonyl-6-diethoxymethyl-1,4-dihydropyridine-3-carboxylate (20 g), diethylamine (1.75 g) and sodium iodide (60.3 mg) in n-propylalcohol (4 ml) was refluxed for 17 hours. After removal of the solvent from the reaction mixture, water and ethyl acetate were ad... | CCOC(=O)C1=C(C(OCC)OCC)NC(C)=C(C(=O)OCCN(CC)CC)C1c1cccc([N+](=O)[O-])c1 | null | 19.3 | null |
1,087,743 | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | null | 2011-01-01T00:09:00 | true | [F:1][C:2]([F:14])([O:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)[C:3]([OH:5])=O.C(Cl)(=O)C(Cl)=O.Cl.[CH3:22][NH:23][O:24][CH3:25]>C(Cl)Cl.CN(C=O)C>[F:14][C:2]([F:1])([O:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)[C:3]([N:23]([O:24][CH3:25])[CH3:22])=[O:5] | CNOC | O=C(O)C(F)(F)Oc1ccc(F)cc1 | null | Cl | O=C(Cl)C(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 2 | To a solution of 2,2-difluoro-2-(4-fluorophenoxy)acetic acid (2.2 g, 10.6 mmol) in DCM (20 ml), were added oxalyl chloride (1.02 ml, 12 mmol) and a couple of drops of DMF and the reaction mixture was stirred for 2 h. The reaction mixture was evaporated to dryness and the yellowish residue was dissolved in DCM. The solv... | CON(C)C(=O)C(F)(F)Oc1ccc(F)cc1 | null | 77.6 | null |
901,878 | ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded | null | 2009-01-01T00:08:00 | true | [OH:1][C:2]([C:31]([F:34])([F:33])[F:32])([CH2:15][C:16]([CH3:30])([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]2([CH3:29])OCC[O:25]2)[CH:19]=1)[CH3:17])[CH2:3][N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[O:14])[CH:6]=[CH:5]1.C(O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH+]1C=CC=CC=1>O>[C:24]([C:20]1[CH:19]=[C:18]([C... | CC(C)(CC(O)(Cn1ccc(=O)c2ccccc21)C(F)(F)F)c1cccc(C2(C)OCCO2)c1 | null | null | Cc1ccc(S(=O)(=O)O)cc1 | c1cc[nH+]cc1 | 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 mixture of 1-{2-hydroxy-4-methyl-4-[3-(2-methyl-[1,3]dioxolan-2-yl)phenyl]-2-trifluoromethylpentyl}-1H-quinolin-4-one (0.35 g, 0.75 mmol), ethanol (24 mL), water (4.8 mL), and pyridinium p-toluenesulfonic acid (95 mg, 0.37 mmol) was heated to reflux for 3 hours, cooled to room temperature, and concentrated in vacuo t... | CC(=O)c1cccc(C(C)(C)CC(O)(Cn2ccc(=O)c3ccccc32)C(F)(F)F)c1 | null | null | null |
1,331,572 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[C:19]4=[N:20][CH:21]=[N:22][CH:23]=[C:18]4[CH:17]=[N:16]3)=[CH:11][CH:10]=2)O1.[OH-:25].[Na+].OO>C1COCC1>[N:15]1([C:12]2[CH:13]=[CH:14][C:9]([OH:25])=[CH:10][CH:11]=2)[C:19]2=[N:20][CH:21]=[N:22][CH:23]=[C:18]2[CH:17]=[N:16]1 | [OH-] | CC1(C)OB(c2ccc(-n3ncc4cncnc43)cc2)OC1(C)C | null | OO | [Na+] | 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 | 0 | 0.5 | The title compound 4-(1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenol (22) was prepared by the following procedure: To a solution of 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-pyrazolo[3,4-d]pyrimidine (22C) (100 mg, 0.31 mmol) in THF (5 mL) was added NaOH (0.248 mL, 0.621 mmol) and hydrogen peroxide (0.048 m... | Oc1ccc(-n2ncc3cncnc32)cc1 | null | null | null |
534,860 | ord_dataset-b1a34bc8c1204d51a772ed27396c794e | null | 2002-01-01T00:02:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH:9]1[CH2:18][C:17]2[N:16]=[CH:15][CH:14]=[C:13]([CH3:19])[C:12]=2[C:11](=O)[CH2:10]1.[C:21]([NH:24][NH2:25])([NH2:23])=[NH:22].[ClH:26].Cl.O>C(O)C>[ClH:26].[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH:9]1[CH2:18][C:17]2[N:16]=[CH:15][CH:14]=[C:13]([CH3:1... | Cc1ccc(F)c(C2CC(=O)c3c(C)ccnc3C2)c1 | N=C(N)NN | null | Cl | 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 | null | null | To a solution of 7-(2-fluoro-5-methylphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (1.1 g) and aminoguanidine hydrochloride (0.54 g) in ethanol (30 ml) were added concentrated hydrochloric acid (1.0 ml) and water (1.0 ml), and the mixture was refluxed for 7 hours. Under reduced pressure, the solvent was evaporated,... | Cc1ccc(F)c(C2CC(=NNC(=N)N)c3c(C)ccnc3C2)c1 | null | 94.7 | null |
970,309 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | [CH2:1]([O:3][C:4]([C:6]1[CH2:7][C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]1[O:21][CH2:22][O:23][C:10]=1[CH:9]=2)=[O:5])[CH3:2].[Se](=O)=[O:25]>O1CCOCC1>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:25])[C:8]2[C:13]([C:14]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[CH:12][C:11]1[O:21]... | CCOC(=O)C1=C(c2ccccc2)c2cc3c(cc2C1)OCO3 | O=[Se]=O | null | null | 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 | 24 | 5,6-Methylenedioxy-3-phenyl-1H-indene-2-carboxylate ethyl ester (3 g, 9.73 mmol) was dissolved in 1,4-dioxane. Selenium dioxide (10.8 g, 97.3 mmol) was added thereto and the reaction mixture was refluxed while stirring for 1 day, followed by cooling. The solution obtained after filtering residual solid selenium dioxide... | CCOC(=O)C1=C(c2ccccc2)c2cc3c(cc2C1=O)OCO3 | null | 69.5 | null |
1,124,662 | ord_dataset-285df12e34cd46e993e3c8ebc3a8962a | null | 2012-01-01T00:01:00 | true | [F:1][C:2]1[CH:10]=[C:9]([O:11][C:12](=[O:14])[CH3:13])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C(Cl)(=O)C([Cl:18])=O>ClCCl.CN(C=O)C>[F:1][C:2]1[CH:10]=[C:9]([O:11][C:12](=[O:14])[CH3:13])[CH:8]=[CH:7][C:3]=1[C:4]([Cl:18])=[O:5] | CC(=O)Oc1ccc(C(=O)O)c(F)c1 | O=C(Cl)C(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 3 | To a solution of 2-fluoro-4-hydroxybenzoic acid (1.87 g, 12 mmol) in 30 mL pyridine was added acetic anhydride (1.84 g, 18 mmol) and catalytic amount of DMAP and the reaction mixture was stirred at rt for 15 h. The pyridine was removed under reduced pressure; the residue was dissolved in EtOAc (100 mL), washed with 1N ... | CC(=O)Oc1ccc(C(=O)Cl)c(F)c1 | null | 101.8 | null |
1,266,606 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | C[O:2][C:3](=[O:33])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([F:14])=[CH:11][CH:12]=2)[C:7]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)(=[O:24])=[O:23])=[CH:18][CH:17]=2)=[C:6]1[CH3:32].[OH-].[Na+].Cl>O1CCCC1>[F:14][C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[N:5](... | COC(=O)Cn1c(C)c(Cc2ccc(S(=O)(=O)c3ccc(F)cc3)cc2)c2cc(F)ccc21 | null | null | Cl | [Na+] | [OH-] | 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 | 1 | A mixture of {5-fluoro-3-[4-(4-fluorobenzenesulfonyl)benzyl]-2-methylindol-1-yl}acetic acid methyl ester (0.079 g) and tetrahydrofuran (1.0 mL) was treated with 5.0 M aqueous sodium hydroxide solution (1.5 mL), and the resulting mixture was stirred at 40° C. for 1 hour. The mixture was acidified by the addition of 5.0 ... | Cc1c(Cc2ccc(S(=O)(=O)c3ccc(F)cc3)cc2)c2cc(F)ccc2n1CC(=O)O | null | 73.1 | null |
224,767 | ord_dataset-1d5bba1436bd42b7a27c43833c25d871 | null | 1991-01-01T00:03:00 | true | Cl[CH:2]([C:8]([C:10]([F:13])([F:12])[F:11])=O)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:14]([NH:18][C:19]([NH2:21])=[O:20])([CH3:17])([CH3:16])[CH3:15]>C(Cl)Cl>[CH3:15][C:14]([NH:18][C:19]1[O:20][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[C:8]([C:10]([F:13])([F:12])[F:11])[N:21]=1)([CH3:17])[CH3:16] | CC(C)(C)NC(N)=O | CCOC(=O)C(Cl)C(=O)C(F)(F)F | 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 | A reaction vessel was charged with 10.9 g (50 mmol) of ethyl 2-chloro-4,4,4-trifluoroacetoacetate and 7.0 g (60 mmol) of tert-butylurea. The reaction mixture was stirred and heated at 140°-150° C. for 19 hours under a calcium sulfate drying tube. With the mixture at room temperature, the mixture was slurried in methyle... | CCOC(=O)c1oc(NC(C)(C)C)nc1C(F)(F)F | null | 62.8 | null |
1,091,621 | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | null | 2011-01-01T00:09:00 | true | C(OC([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([S:20][C:21](N(C)C)=O)=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.[N:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1CCl>C(OCC)C>[ClH:19].[Cl:19][C:16]1[CH:17]=[CH:18][C:11]2[CH2:10][CH2:9][NH:8][CH2:14][CH2:13][C:12]=2[C:15]=1[S:20][CH2:21][C:28]1[CH:29]=[CH... | CN(C)C(=O)Sc1c(Cl)ccc2c1CCN(C(=O)OC(C)(C)C)CC2 | ClCc1ccccn1 | 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 | 25 | 16 | Using a method similar to the General Procedure 7, react 3-tert-butoxycarbonyl-7-chloro-6-dimethylaminocarbonylthio-2,3,4,5-tetrahydro-1H-benzo[d]azepine (8 g, 20.8 mmol) with 2-picolyl chloride hydrochloride (3.41 g, 20.8 mmol). Dilute the reaction mixture with diethyl ether and filter the precipitate. Concentrate the... | Clc1ccc2c(c1SCc1ccccn1)CCNCC2 | null | null | null |
1,003,142 | ord_dataset-70899a0178cc441482746c093624afa0 | null | 2010-01-01T00:10:00 | true | [S:1]1[CH:5]=[C:4]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([NH:16][C:17]4[C:26]5[C:21](=[CH:22][CH:23]=[CH:24][C:25]=5[O:27][C@@H:28]([CH3:32])[C:29]([OH:31])=O)[N:20]=[CH:19][N:18]=4)=[CH:13][CH:14]=3)[CH:9]=[N:8]2)[N:3]=[CH:2]1.[NH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1>>[CH3:32][C@H:28]([O:27][C:25]1[CH:24]=[... | C[C@H](Oc1cccc2ncnc(Nc3ccc4c(cnn4Cc4cscn4)c3)c12)C(=O)O | C1COCCN1 | 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 the same procedure as in Example 44, (2S)-2-[(4-{[1-(1,3-thiazol-4-ylmethyl)-1H-indazol-5-yl]amino}quinazolin-5-yl)oxy]propanoic acid (250 mg, 0.56 mmol) was reacted with morpholine to give the title compound as a white solid (160 mg, 55%); NMR Spectrum 1.58 (d, 3H), 3.70-3.40 (m, 8H), 5.79 (s, 2H), 5.88 (q, 1H),... | C[C@H](Oc1cccc2ncnc(Nc3ccc4c(cnn4Cc4cscn4)c3)c12)C(=O)N1CCOCC1 | null | 55 | null |
556,316 | ord_dataset-f483e698250b4da0a84f425c7bfa965a | null | 2002-01-01T00:08:00 | true | [NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.Cl[C:7]1[N:8]=[C:9]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]3[O:25][CH2:26][CH2:27][O:28][C:21]=3[CH:20]=2)[C:10]2[CH:15]=[C:14]([CH3:16])[S:13][C:11]=2[N:12]=1>>[N:1]1([C:7]2[N:8]=[C:9]([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]4[O:25][CH2:26][CH2:27][O:28][C:21]=4[CH:20]=3)[C:10]... | Cc1cc2c(NCc3ccc4c(c3)OCCO4)nc(Cl)nc2s1 | c1c[nH]cn1 | 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 the procedure of Example 97, the reaction of imidazole with 2-chloro-6-methyl-4-(3,4-ethylendioxybenzylamino)-thieno-[2,3-d]-pyrimidine gives 2-(imidazol-1-yl)-6-methyl-4-(3,4-ethylendioxybenzylamino)-thieno-[2,3-d]-pyrimidine. | Cc1cc2c(NCc3ccc4c(c3)OCCO4)nc(-n3ccnc3)nc2s1 | null | null | null |
243,032 | ord_dataset-fa3b512e2d924b9b965301ebcba6853d | null | 1992-01-01T00:03:00 | true | [BH4-].[Na+].[O:3]=[C:4]1[C:9]2[CH:10]=[CH:11][C:12]([O:17][CH2:18][CH2:19][CH2:20][O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:13]([CH2:14][CH2:15][CH3:16])[C:8]=2[O:7][C:6]([CH2:33][CH2:34][C:35]([OH:37])=[O:36])([CH2:28][CH2:29][C:30]([OH:32])=[O:31])[CH2:5]1.Cl>O.O1CCCC1>[OH:3][CH:4]1[C:9]2[CH:10]=[CH:1... | CCCc1c(OCCCOc2ccccc2)ccc2c1OC(CCC(=O)O)(CCC(=O)O)CC2=O | null | null | Cl | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 0.5 | To a stirred solution of 78 mg (2.1 mmol) of NaBH4 in 2 ml of water at 0° C. is added over 3 minutes a solution of 250 mg (0.515 mmol) of the title product of Example 17 in 3 ml of tetrahydrofuran (THF). After 30 minutes at 0° C., the mixture was permitted to warm to room temperature, and a further 2 ml each of water a... | CCCc1c(OCCCOc2ccccc2)ccc2c1OC(CCC(=O)O)(CCC(=O)O)CC2O | null | 59.9 | null |
307,044 | ord_dataset-a6643d22de674f30a85ba57198b82644 | null | 1995-01-01T00:03:00 | true | [S:1]([CH2:5][CH2:6][N:7]=[C:8]=[S:9])([OH:4])(=[O:3])=[O:2].[Na:10].CO.[C:13]([N:16]([CH3:18])[NH2:17])(=[O:15])[CH3:14]>O>[C:13]([N:16]([CH3:18])[NH:17][C:8]([NH:7][CH2:6][CH2:5][S:1]([OH:4])(=[O:3])=[O:2])=[S:9])(=[O:15])[CH3:14].[Na:10] | O=S(=O)(O)CCN=C=S | CC(=O)N(C)N | null | [Na] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | O | null | null | null | null | null | null | null | null | null | null | null | 175.3 g of sodium sulfoethylisothiocyanate was added to a solution obtained by adding 600 ml of methyl alcohol and 300 ml of water to 114.2 g of 1-acetyl-1-methylhydrazine. The system was then heated under reflux for 4 hours. After the reaction, the reaction solution was dried under reduced pressure. The resulting soli... | CC(=O)N(C)NC(=S)NCCS(=O)(=O)O | null | 66 | null |
1,123,643 | ord_dataset-285df12e34cd46e993e3c8ebc3a8962a | null | 2012-01-01T00:01:00 | true | [Cl:1][CH2:2][CH2:3][N:4]([CH2:15][CH2:16][Cl:17])[P:5](Cl)([N:7]([CH2:11][CH2:12][Cl:13])[CH2:8][CH2:9][Cl:10])=[O:6].[OH:18][CH2:19][CH2:20][S:21][CH2:22][CH2:23][OH:24].CC(C)([O-])C.[K+]>O1CCCC1.C(OCC)(=O)C>[Cl:17][CH2:16][CH2:15][N:4]([CH2:3][CH2:2][Cl:1])[P:5]([N:7]([CH2:11][CH2:12][Cl:13])[CH2:8][CH2:9][Cl:10])(=... | OCCSCCO | O=P(Cl)(N(CCCl)CCCl)N(CCCl)CCCl | null | CC(C)(C)[O-] | [K+] | 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 | 2.5 | 0.5 | N,N,N′,N′-Tetrakis(2-chloroethyl)phosphorodiamidoyl chloride, 636 mg (1.745 mmol), and bis(2-hydroxyethyl)sulfide, 1 mL (9.67 mmol), were dissolved in 8 mL anhydrous tetrahydrofuran and cooled to 0-5° C. in an ice-water bath. Potassium tert-butoxide, 1.8 mL of 1 M solution in tetrahydrofuran (1.8 mmol), was added over ... | O=P(OCCSCCO)(N(CCCl)CCCl)N(CCCl)CCCl | null | 42.6 | null |
297,112 | ord_dataset-ec7cb3d5a8704f64b01d401ea555974f | null | 1994-01-01T00:09:00 | true | C1(C[O:8][C:9]2[CH:17]=[CH:16][C:15]3[N:14]([CH3:18])[C:13]4[CH2:19][CH:20]([CH2:22][N:23]([CH3:25])[CH3:24])[CH2:21][C:12]=4[C:11]=3[CH:10]=2)C=CC=CC=1.[H][H]>C(O)C.[Pd]>[CH3:18][N:14]1[C:15]2[CH:16]=[CH:17][C:9]([OH:8])=[CH:10][C:11]=2[C:12]2[CH2:21][CH:20]([CH2:22][N:23]([CH3:25])[CH3:24])[CH2:19][C:13]1=2 | [H][H] | CN(C)CC1Cc2c(n(C)c3ccc(OCc4ccccc4)cc23)C1 | 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 | In a 500 ml Parr hydrogenation bottle was suspended 0.5 g of 10% Pd/C in 50 ml of ethyl alcohol. To this was added a solution of 1,2,3,4-tetrahydro-7-phenylmethoxy-N,N,4-trimethylcyclopent[b]indole-2-methanamine (2.3 g, 0.007 mole) in 200 ml of ethyl alcohol. After shaking at 50° C. under 50 psi hydrogen for two hours,... | CN(C)CC1Cc2c(n(C)c3ccc(O)cc23)C1 | null | null | null |
1,145,442 | ord_dataset-68715347640045adb1b09e6a04722b0e | null | 2012-01-01T00:03:00 | true | [OH:1][C@H:2]([CH2:7][O:8][CH:9]([CH3:11])[CH3:10])[C:3]([O:5][CH3:6])=[O:4].Cl[C:13]1[N:18]=[CH:17][N:16]=[C:15]2[N:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:28])[N:20]=[CH:21][C:14]=12.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[N:19]1[C:15]2=[N:16][CH:17]=[N:18][C... | Clc1ccccc1-n1ncc2c(Cl)ncnc21 | COC(=O)[C@H](O)COC(C)C | null | O=C([O-])[O-] | [K+] | 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 | 130 | null | (R)-methyl 2-hydroxy-3-isopropoxypropanoate D1a (500 mg, 3.08 mmol), 4-chloro-1-(2-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidine B1 (817 mg, 3.08 mmol) and potassium carbonate (0.186 mL, 3.08 mmol) were suspended in acetonitrile (15 mL). The reaction was heated to 130° C. for 4 hours in the microwave reactor and cooled to... | COC(=O)[C@@H](COC(C)C)Oc1ncnc2c1cnn2-c1ccccc1Cl | null | null | null |
70,892 | ord_dataset-06d4002fc4d34860a0688cba690e12dc | null | 1980-01-01T00:09:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.Br[CH2:23][CH:24]=[CH2:25]>C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:25][CH:24]=[CH2:23])[CH2:11][CH2:10]2)=[CH:4][CH:3]=1 | C=CCBr | Clc1ccc(NC2CCNCC2)cc1 | 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 | 25 | 20 | To a stirred mixture of 15 parts of N-(4-chlorophenyl)-4-piperidinamine, 12 parts of N,N-diethylethanamine in 130 parts of benzene is added dropwise a solution of 10.3 parts of 3-bromo-1-propene in 70 parts of benzene. Upon completion, the whole is stirred first for 20 h. 30 at room temperature and further for 40 minut... | C=CCN1CCC(Nc2ccc(Cl)cc2)CC1 | null | null | null |
1,122,108 | ord_dataset-285df12e34cd46e993e3c8ebc3a8962a | null | 2012-01-01T00:01:00 | true | [CH3:1][C:2]1([C:7]2[O:11][N:10]=[C:9]([CH2:12][OH:13])[CH:8]=2)OCC[O:3]1.[OH-].[Na+]>CO>[OH:13][CH2:12][C:9]1[CH:8]=[C:7]([C:2](=[O:3])[CH3:1])[O:11][N:10]=1 | CC1(c2cc(CO)no2)OCCO1 | null | null | [Na+] | [OH-] | 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 | 70 | 18 | To a solution of the carbinol 319 (2.39 g, 12.9 mmol) in MeOH (30 mL) 10% HCl (30 mL) was added. The reaction mixture was stirred at 70° C. for 18 hours, cooled and neutralized to pH 6 using 1M NaOH solution. MeOH was evaporated and the resulting aqueous phase was extracted with EtOAc. The organic layer was washed with... | CC(=O)c1cc(CO)no1 | null | 91.7 | null |
684,552 | ord_dataset-359b8fc87f4244be89d6f02bc5036eac | null | 2005-01-01T00:09:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]([C:14]([N:16]2[CH2:21][CH2:20][CH2:19][C@@H:18]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[CH2:17]2)=O)[C@@H:10]([NH:30]C(NC2C=CC=C(C(=O)C)C=2)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>B.O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]([CH2... | CC(=O)c1cccc(NC(=O)N[C@H]2CN(C(=O)OC(C)(C)C)CC[C@H]2C(=O)N2CCC[C@@H](Cc3ccc(F)cc3)C2)c1 | null | null | B | 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 | 19 | In a dry flask (3R,4R)-3-[3-(3-acetyl-phenyl)-ureido]-4-[(S)-3-(4-fluoro-benzyl)-piperidine-1-carbonyl]-piperidine-1-carboxylic acid t-butyl ester (1.19 g, 2.84 mmol) was dissolved in borane (100 mL of a 1M solution in tetrahydrofuran, 100 mmol). The reaction was stirred 19 hours. The reaction mixture was concentrated ... | CC(C)(C)OC(=O)N1CC[C@@H](CN2CCC[C@@H](Cc3ccc(F)cc3)C2)[C@@H](N)C1 | null | 22.5 | null |
526,421 | ord_dataset-293186f5c9b441cab57f03cd3a18ac26 | null | 2001-01-01T00:11:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[Cl:27])[CH2:5][NH:6][CH2:7][CH2:8][CH2:9][NH:10][C:11]1[CH:20]=[C:19]([O:21]C)[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[Cl:23])[N:12]=1.[ClH:28]>O1CCOCC1>[ClH:1].[ClH:28].[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[Cl:27])[CH2:5][NH:6][CH2:7][CH2:8][CH2:9][NH:10... | COc1cc(NCCCNCc2ccc(Cl)c(Cl)c2)nc2cccc(Cl)c12 | 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 | null | 2-[3-(3,4-Dichlorobenzylamino)prop-1-ylamino]-5-chloro-4-methoxyquinoline (78 mg, 0.18 mmol) in dioxane:concentrated aq. HCl 1:2 (7 ml) was heated at 80° C. for 18 h. Volatiles were evaporated in vacuo and the residue was triturated with CHCl3:tBuOMe 2:1 and filtered to give the title compound as a colourless solid, (3... | O=c1cc(NCCCNCc2ccc(Cl)c(Cl)c2)[nH]c2cccc(Cl)c12 | null | 34 | null |
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