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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
519,071 | ord_dataset-a495451286334c5c9bbcbd48a00c1350 | null | 2001-01-01T00:09:00 | true | Br[CH2:2][C:3]([NH:5][C@@H:6]1[C:13](=[O:14])[N:12]2[C@@H:7]1[S:8][CH2:9][C:10](/[CH:18]=[C:19]1/[C:20](=[O:43])[N:21]([CH2:24][C:25]3[CH:30]=[CH:29][N+:28]([CH2:31][C:32](=[O:42])[NH:33][C:34]4[CH:39]=[CH:38][C:37]([OH:40])=[C:36]([F:41])[CH:35]=4)=[CH:27][CH:26]=3)[CH2:22][CH2:23]/1)=[C:11]2[C:15]([O-:17])=[O:16])=[O... | O=C(C[n+]1ccc(CN2CC/C(=C\C3=C(C(=O)[O-])N4C(=O)[C@@H](NC(=O)CBr)[C@H]4SC3)C2=O)cc1)Nc1ccc(O)c(F)c1 | Cn1cnnc1S | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 12 | To a solution of 230.0 mg (0.34 mmol) (E)-(6R,7R)-7-(2-Bromo-acetylamino)-3-(1-[1-[(3-fluoro-4-hydroxy-phenylcarbamoyl)-methyl]-pyridin-1-ium-4-ylmethyl]-2-oxo-pyrrolidin-3-ylidenemethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylate in 5 ml N,N-dimethylformamide was added 40.0 mg (0.37 mmol) 4-methyl-4H-[1,... | Cn1cnnc1SCC(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(/C=C3\CCN(Cc4cc[n+](CC(=O)Nc5ccc(O)c(F)c5)cc4)C3=O)CS[C@H]12 | null | null | null |
1,733,199 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | [CH2:1]([N:4]1[C:12]2[C:11](=[O:13])[NH:10][C:9](=[O:14])[NH:8][C:7]=2[N:6]=[CH:5]1)[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].I[CH2:22][CH3:23]>CN(C=O)C>[CH2:1]([N:4]1[C:12]2[C:11](=[O:13])[NH:10][C:9](=[O:14])[N:8]([CH2:22][CH3:23])[C:7]=2[N:6]=[CH:5]1)[CH:2]=[CH2:3] | C=CCn1cnc2[nH]c(=O)[nH]c(=O)c21 | CCI | 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 | 25 | 8 | To a solution of 7-allyl-1H-purine-2,6(3H,7H)-dione (15 g, 78.13 mmol) in DMF (200 mL) was added potassium carbonate (23.7 g, 171.74 mmol), followed by dropwise addition of iodoethane (3.6 mL, 44.54 mmol). The reaction was stirred at room temperature overnight. The reaction was concentrated and partitioned between ethy... | C=CCn1cnc2c1c(=O)[nH]c(=O)n2CC | null | 71.4 | null |
919,564 | ord_dataset-8e59bd24817446f7b1c68e805b8e5f1d | null | 2009-01-01T00:11:00 | true | [NH2:1][C:2]1[C:7]([C:8]([C:10]2[CH:15]=[C:14]([F:16])[C:13]([CH3:17])=[CH:12][C:11]=2[O:18][CH3:19])=[O:9])=[CH:6][N:5]=[C:4]([NH:20][CH:21]2[CH2:26][CH2:25][CH:24]([NH2:27])[CH2:23][CH2:22]2)[N:3]=1.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>>[NH2:1][C:2]1[C:7]([C:8](=[O:9])[C:10]2[CH:15]=[C:14]([F:16])[C:13]([CH3:17])=[CH:1... | COc1cc(C)c(F)cc1C(=O)c1cnc(NC2CCC(N)CC2)nc1N | CS(=O)(=O)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 | The similar procedure as described in Example 60 was used, starting from [4-amino-2-(4-amino-cyclohexylamino)-pyrimidin-5-yl]-(5-fluoro-2-methoxy-4-methyl-phenyl)-methanone (Example 345) and methanesulfonyl chloride (Aldrich) to give N-[4-[4-amino-5-(5-fluoro-2-methoxy-4-methyl-benzoyl)-pyrimidin-2-ylamino]-cyclohexyl]... | COc1cc(C)c(F)cc1C(=O)c1cnc(NC2CCC(NS(C)(=O)=O)CC2)nc1N | null | null | null |
1,675,299 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [F:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][CH2:7][C:8]2[S:9][C:10]3[N:11]=[CH:12][N:13]=[C:14]([N:17]4[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]4)[C:15]=3[N:16]=2)=[CH:4][CH:3]=1.[Cl:25][C:26]1[CH:36]=[CH:35][C:29]([O:30][CH2:31][C:32](O)=[O:33])=[CH:28][CH:27]=1>>[F:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][CH2:7][C:8]2[S:9][C:1... | O=C(O)COc1ccc(Cl)cc1 | Fc1ccc(CCc2nc3c(N4CCNCC4)ncnc3s2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | This compound was prepared from 2-(4-fluorophenethyl)-7-(piperazin-1-yl)thiazolo[5,4-d]pyrimidine using 4-chlorophenoxyacetic acid in a yield of 48%, according to the procedure for the synthesis of example 50. | O=C(COc1ccc(Cl)cc1)N1CCN(c2ncnc3sc(CCc4ccc(F)cc4)nc23)CC1 | null | 48 | null |
1,679,599 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | CN(C)C(N1[CH2:10][CH:9]=[C:8]([C:11]2[NH:28][C:14]3[N:15]=[CH:16][N:17]=[C:18]([C:19]4[CH:24]=[C:23]([F:25])[CH:22]=[C:21]([NH2:26])[C:20]=4[CH3:27])[C:13]=3[CH:12]=2)[CH2:7][CH2:6]1)=O.ClC1C2C=C(C3CC[C:43]4([O:47][CH2:46][CH2:45][O:44]4)CC=3)NC=2N=CN=1>>[O:44]1[C:43]2([CH2:6][CH2:7][C:8]([C:11]3[NH:28][C:14]4[N:15]=[C... | Clc1ncnc2[nH]c(C3=CCC4(CC3)OCCO4)cc12 | Cc1c(N)cc(F)cc1-c1ncnc2[nH]c(C3=CCN(C(=O)N(C)C)CC3)cc12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Intermediate 18 was prepared analogue to Intermediate 6 by replacing Intermediate 3 with Intermediate 17. | Cc1c(N)cc(F)cc1-c1ncnc2[nH]c(C3=CCC4(CC3)OCCO4)cc12 | null | null | null |
1,057,979 | ord_dataset-373415d3e0e54004837cf4831e67666f | null | 2011-01-01T00:05:00 | true | [Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4](Cl)=[O:5].[CH2:12]([NH:14][CH2:15][C:16]([CH2:22][NH:23][C:24]1[CH:32]=[C:31]([CH3:33])[CH:30]=[C:29]2[C:25]=1[CH:26]=[N:27][N:28]2[C:34]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=1)([OH:21])[C:17]([F:20])([F:19])[F:18])[CH3:13]>>[Cl:1][C:2]1[CH:10]=[CH:9][C... | O=C(Cl)c1c(F)cccc1Cl | CCNCC(O)(CNc1cc(C)cc2c1cnn2-c1ccc(F)cc1)C(F)(F)F | null | null | null | null | null | null | null | 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 similarly to Example 48 from 2-chloro-6-fluorobenzoylchloride and 3-(ethylamino)-1,1,1-trifluoro-2-({[1-(4-fluorophenyl)-6-methyl-1H-indazol-4-yl]amino}methyl)-2-propanol. | CCN(CC(O)(CNc1cc(C)cc2c1cnn2-c1ccc(F)cc1)C(F)(F)F)C(=O)c1c(F)cccc1Cl | null | null | null |
815,336 | ord_dataset-50f99930fc41474db226bc80774b38df | null | 2008-01-01T00:04:00 | true | [CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([OH:24])CC2C=CC=CC=2OC)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:31][C:32]([F:43])([F:42])[O:33][C:34]1[CH:41]=[CH:40][CH:39]=[CH:38][C:35]=1[CH2:36]Br>>[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]([C:25]... | COc1ccccc1CC(O)(c1ccccc1)C1CN(Cc2ccccc2)CCO1 | FC(F)(F)Oc1ccccc1CBr | null | null | null | null | null | null | null | 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 procedure for the synthesis of example 1a, 1-(4-Benzyl-morpholin-2-yl)-2-(2-methoxy-phenyl)-1-phenyl-ethanol, was followed using 2-(trifluoromethoxy)benzyl bromide (available from Fluorochem) as starting material and making non-critical variations, to yield the title compound. FIA [M+H]+=458. | OC(Cc1ccccc1OC(F)(F)F)(c1ccccc1)C1CN(Cc2ccccc2)CCO1 | null | null | null |
438,942 | ord_dataset-3e8f24b5bc8e4d8bb9b6e7e89a956e12 | null | 1999-01-01T00:09:00 | true | [CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH2:16][C:17]([NH:24][C:25]([O:27][CH3:28])=[O:26])([CH3:23])C(OCC)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Li+].Cl.O>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH2:16][C:17]1([CH3:23])[CH2:28][O:27][C:25](=[O:26... | CCOC(=O)C(C)(CCc1ccccc1OCc1ccccc1)NC(=O)OC | null | null | Cl | [BH4-] | [Li+] | 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 | 25 | 0.5 | To a solution of ethyl 4-(2-benzyloxyphenyl)-2-methoxycarbonylamino-2-methylbutanoate (5.2 g) in tetrahydrofuran (135 ml), under a nitrogen atmosphere, lithium borohydride (0.59 g) was added and the mixture was refluxed under heating for an hour. Then, a 2N hydrochloric acid (6.6 ml) was added thereto and the mixture w... | CC1(CCc2ccccc2OCc2ccccc2)COC(=O)N1 | null | 109.5 | null |
1,189,320 | ord_dataset-9cd817a75dfc4fe7ad19d4232772d5ff | null | 2012-01-01T00:07:00 | true | C(N(CC)CC)C.[C:8]([N:15]1[CH:19]=[CH:18][N:17]=[CH:16]1)([N:10]1[CH:14]=[CH:13]N=[CH:11]1)=[O:9].Cl.N1CC[CH:24]([O:27][C:28]2[N:33]=[CH:32][N:31]=[C:30]([N:34]3[C:42]4[C:37](=[CH:38][C:39]([S:43]([CH2:46][CH2:47][CH3:48])(=[O:45])=[O:44])=[CH:40][CH:41]=4)[CH2:36][CH2:35]3)[CH:29]=2)[CH2:23]C1>C1COCC1>[N:15]1([C:8]([N:... | O=C(n1ccnc1)n1ccnc1 | CCCS(=O)(=O)c1ccc2c(c1)CCN2c1cc(OC2CCNCC2)ncn1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 25 | 3 | Triethylamine (286 μL, 2.05 mmol) and 1,1′-carbonyldiimidazole (249 mg, 1.54 mmol) were added to a THF (9.00 mL) solution of the 1-[6-(piperidin-4-yloxy)pyrimidin-4-yl]-5-(propylsulfonyl)indoline hydrochloride (450 mg, 1.03 mmol) produced in Reference Example 32, and the mixture was stirred at room temperature for 3 ho... | CCCS(=O)(=O)c1ccc2c(c1)CCN2c1cc(OC2CCN(C(=O)n3ccnc3)CC2)ncn1 | null | 56.9 | null |
1,239,355 | ord_dataset-e96f5a2842f14e5380461c234100f05a | null | 2012-01-01T00:12:00 | true | [CH2:1]([O:3][C:4](=[O:27])[CH2:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:15]=2[CH2:23][NH:24][CH2:25][CH3:26])[C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)[CH3:2].Cl[C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30]>>[CH2:1]([O:3][C:4](=[O:27])[CH2:5][C:6]1... | CCNCc1cc([N+](=O)[O-])ccc1-c1cc(CC(=O)OCC)ccc1OC | O=C(Cl)OCc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared according to the procedure described in Example 1, Step 6, using the following starting materials: (2′-ethylaminomethyl-6-methoxy-4′-nitro-biphenyl-3-yl)-acetic acid ethyl ester and benzyl chloroformate. | CCOC(=O)Cc1ccc(OC)c(-c2ccc([N+](=O)[O-])cc2CN(CC)C(=O)OCc2ccccc2)c1 | null | null | null |
283,785 | ord_dataset-769fac6048e548eca2d49e48f972884b | null | 1994-01-01T00:01:00 | true | [O:1]1CCO[CH:2]1[C:6]1[CH:7]=[C:8]([CH:23]=[CH:24][CH:25]=1)[CH2:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[O:19][CH2:20][C:21]#[N:22])[CH:12]=[CH:11]1>O1CCCC1.Cl.O>[CH:2]([C:6]1[CH:7]=[C:8]([CH:23]=[CH:24][CH:25]=1)[CH2:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[O:19][CH2:20][C:21]#[N:22])[CH:1... | N#CCOc1cccc2ccn(Cc3cccc(C4OCCO4)c3)c12 | null | null | Cl | null | 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 | A solution of 1-[3-(1,3-dioxolan-2-yl)benzyl]-7-cyanomethoxyindole (50 mg., 0.15 mmol) in tetrahydrofuran (1 ml) and 2M hydrochloric acid (0.5 ml) was stirred at room temperature for 1 hour, diluted with water and extracted with ethyl acetate. The extract was dried and evaporated to a dark oil. | N#CCOc1cccc2ccn(Cc3cccc(C=O)c3)c12 | null | null | null |
461,979 | ord_dataset-5ca9db262dd24c5a9315cdc8ef055b7e | null | 2000-01-01T00:04:00 | true | [C:1](OC(=O)C)(=[O:3])C.[CH3:8][C:9]1[NH:23][CH2:22][CH2:21][C:11]2=[C:12]3[C:17](=[N:18][C:10]=12)[CH:16]=[CH:15][C:14]([O:19][CH3:20])=[CH:13]3>C(O)=O>[CH2:8]=[C:9]1[C:10]2[NH:18][C:17]3[C:12](=[CH:13][C:14]([O:19][CH3:20])=[CH:15][CH:16]=3)[C:11]=2[CH2:21][CH2:22][N:23]1[CH:1]=[O:3] | CC(=O)OC(C)=O | COc1ccc2c(c1)=C1CCNC(C)=C1N=2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=CO | null | null | null | null | null | null | null | null | null | null | 50 | 2 | To acetic anhydride (1 ml) cooled to 0° C. is added dropwise formic acid (0.5 ml). The mixture is heated for 15 min. at 50° C. After cooling rapidly to 0° C., 10-methoxyharmalan (200 mg) is added slowly and portionwise and the medium is left stirring for 2 h. The crude product is then taken to dryness and, after separa... | C=C1c2[nH]c3ccc(OC)cc3c2CCN1C=O | null | null | null |
1,674,486 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[H-].[Na+].Br[CH2:13][CH:14]1[CH2:16][O:15]1>CN(C=O)C>[O:15]1[CH2:16][CH:14]1[CH2:13][O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6] | BrCC1CO1 | O=Cc1cccc(O)c1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | 0.5 | To a solution of 3-hydroxybenzaldehyde (2.0 g, 16.38 mmol) in DMF (30 mL) at 0° C. was added NaH (983 mg, 24.57 mmol) in portions. After 0.5 h, a solution of 2-(bromomethyl)oxirane (2.69 mg, 19.65 mmol) in DMF (5 mL) was added and the reaction mixture was warmed to room temperature for 5 h. The mixture was concentrated... | O=Cc1cccc(OCC2CO2)c1 | null | 72 | null |
577,331 | ord_dataset-a9ba4801408c4b01922886164c10a391 | null | 2003-01-01T00:01:00 | true | [NH2:1][C:2]1[CH:3]=[C:4](/[C:8](/[C:12]2[N:13]=[CH:14][N:15]([S:17]([N:20]([CH3:22])[CH3:21])(=[O:19])=[O:18])[CH:16]=2)=[CH:9]/[O:10][CH3:11])[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[CH2:29]([S:31](Cl)(=[O:33])=[O:32])[CH3:30].Cl>ClCCl>[CH2:29]([S:31]([NH:1][C:2]1[CH:3]=[C:4](/[C:8](/[C:12]2[N:13]=[CH:14][N:15]([S:17]([N:2... | CCS(=O)(=O)Cl | CO/C=C(/c1cccc(N)c1)c1cn(S(=O)(=O)N(C)C)cn1 | null | 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 | 5 | A solution of Example 46B (0.32 g, 0.99 mmol) in dichloromethane (5 mL) was treated with pyridine (0.24 mL, 3.0 mmol), treated with ethanesulfonyl chloride (0.10 mL, 1.1 mmol), stirred for 5 hours, treated with 1M HCl and extracted with dichloromethane (3×). The combined dichloromethane extractions were dried (Na2SO4) ... | CCS(=O)(=O)Nc1cccc(/C(=C/OC)c2cn(S(=O)(=O)N(C)C)cn2)c1 | null | null | null |
1,717,391 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[C:12]([C:14]([OH:16])=O)[CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:17][C:18]([CH3:25])([C:20]1[S:21][CH:22]=[CH:23][N:24]=1)[NH2:19]>>[CH3:17][C:18]([NH:19][C:14]([C:12]1[CH:11]=[CH:10][CH:9]=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[N:13]=1)=[O:16])([C:20]1[S... | O=C(O)c1cccc(-c2cccc(Cl)c2)n1 | CC(C)(N)c1nccs1 | null | null | null | null | null | null | null | 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 synthesized in analogy to Example 1, using 6-(3-chlorophenyl)-2-pyridinecarboxylic acid (CAN 863704-38-5) and α,α-dimethyl-2-thiazolemethanamine (CAN 1082393-38-1) as starting materials, MS (LC/MS): 358.0 [M+H]+. | CC(C)(NC(=O)c1cccc(-c2cccc(Cl)c2)n1)c1nccs1 | null | null | null |
517,566 | ord_dataset-a495451286334c5c9bbcbd48a00c1350 | null | 2001-01-01T00:09:00 | true | [H-].[Na+].[CH3:3][N:4]1[C:8]([CH2:9][OH:10])=[N:7][CH:6]=[N:5]1.Cl[C:12]1[C:13]([N:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)=[CH:14][C:15]2[N:16]([C:18]([C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)=[N:19][N:20]=2)[N:17]=1>CN(C=O)C>[CH3:3][N:4]1[C:8]([CH2:9][O:10][C:12]2[C:13]([N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)=[... | Clc1nn2c(-c3cccnc3)nnc2cc1N1CCCC1 | Cn1ncnc1CO | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | 18 | Sodium hydride (60% dispersion in oil, 16 mg, 0.41 mmol) was added to a solution of (2-methyl-2H-1,2,4-triazol-3-yl)methanol (EP-A-421210; 40 mg, 0.35 mmol) in dry DMF (2 ml) at room temperature. After 1 h at room temperature a solution of 6-chloro-3-(pyridin-3-yl)-7-(pyrrolidin-1-yl)-1,2,4-triazolo[4,3-b]pyridazine (1... | Cn1ncnc1COc1nn2c(-c3cccnc3)nnc2cc1N1CCCC1 | null | 60.2 | null |
571,488 | ord_dataset-5e1b2445a3d94ea592ddf2c284118a1e | null | 2002-01-01T00:11:00 | true | [CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:13][O:12][C:11](=[O:14])[CH:10]=2)=[CH:5][CH:4]=1.[I:15]I>N1C=CC=CC=1.CCOCC>[I:15][C:10]1[C:11](=[O:14])[O:12][CH2:13][C:9]=1[C:6]1[CH:7]=[CH:8][C:3]([S:2][CH3:1])=[CH:4][CH:5]=1 | CSc1ccc(C2=CC(=O)OC2)cc1 | II | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | 24 | To a solution of 3 g of the product of Step 2 in 30 ml of pyridine is added 8.7 g of I2. The mixture is stirred for 24 h and then diluted with 200 ml of ether, washed with 100 ml of 5N HCl and 50 ml of 5N Na2S2O3. The ether layer is dried over Na2SO4 and concentrated to give the title compound. | CSc1ccc(C2=C(I)C(=O)OC2)cc1 | null | null | null |
91,439 | ord_dataset-90c12c4a89ae46d88aea27f4e37ba124 | null | 1982-01-01T00:02:00 | true | [O-]S([O-])(=O)=O.[Zn+2:6].[N:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]([OH:15])=[O:14].[Zn]>O>[N:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]([O-:15])=[O:14].[Zn+2:6].[N:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]([O-:15])=[O:14] | O=C(O)c1ccccn1 | null | null | O=S(=O)([O-])[O-] | [Zn+2] | [Zn] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | null | 0.07 | Thirty grams of ZnSO4 ·7H2O was dissolved in 200 ml. deionized water at room temperature. Thereafter, 20 g. picolinic acid (Sigma Chemical, St. Louis, MO) was added to the solution and the solution was stirred continuously. Within 3-5 minutes a precipitate began to form. After 30 minutes the stirring was discontinued a... | O=C([O-])c1ccccn1 | null | null | null |
157,248 | ord_dataset-58ec6779628e43e2b3f0972725f262e6 | null | 1987-01-01T00:05:00 | true | C([O:4][C:5]1[C:6]2[C:19]([O:20]C(=O)C)=[CH:18][CH:17]=[CH:16][C:7]=2[S:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=O)C.C[O-].[Na+]>CO.C(O)(=O)C>[OH:4][C:5]1[C:6]2[C:19]([OH:20])=[CH:18][CH:17]=[CH:16][C:7]=2[S:8][C:9]=1[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1 | CC(=O)Oc1cccc2sc(-c3ccccc3)c(OC(C)=O)c12 | null | null | C[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | CO | null | null | null | null | null | null | null | null | null | null | null | A solution of 3,4-diacetoxy-2-phenylbenzo[b]thiophene (28 mg) in methanol (5 ml) was treated with a catalytic amount of sodium methoxide for 18 hours at room temperature. One drop of acetic acid was added, and the solution was evaporated. The residue was dissolved in dichloromeethane, filtered and the filtrate evaporat... | Oc1cccc2sc(-c3ccccc3)c(O)c12 | null | null | null |
1,707,006 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:16]=[CH:17][C:18]3[C:19]4[CH2:28][NH:27][CH2:26][CH2:25][C:20]=4[N:21]([CH3:24])[C:22]=3[CH:23]=2)[C:11](=[O:29])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[CH2:31][CH2:32][OH:33].C(N(CC)CC)C.[ClH:41]>CC#N>[ClH:41].[ClH:41].[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][... | OCCI | Cn1c2c(c3ccc(-n4ccc(OCc5ccccc5)cc4=O)cc31)CNCC2 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CC#N | null | null | null | null | null | null | null | null | null | null | null | 4-(Benzyloxy)-1-(5-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-7-yl)pyridin-2(1H)-one (75 mg, 0.16 mmol), 2-iodoethanol (17 μL, 36 mg, 0.21 mmol) and triethylamine (105 μL, 0.82 mmol) were dissolved in MeCN (2 mL) and heated to reflux for 3 h. The mixture was then concentrated and purified by flash column chromatog... | Cn1c2c(c3ccc(-n4ccc(OCc5ccccc5)cc4=O)cc31)CN(CCO)CC2 | null | 27 | null |
795,140 | ord_dataset-744b04e8228742eb9aa4bde36f5dedf1 | null | 2007-01-01T00:10:00 | true | [Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[CH3:9][N:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[CH:15]=[O:16]>ClCCl>[C:5]([C:13]1[CH:12]=[C:11]([CH:15]=[O:16])[N:10]([CH3:9])[CH:14]=1)(=[O:7])[CH3:6] | Cn1cccc1C=O | CC(=O)Cl | null | [Al+3] | [Cl-] | 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 | To a suspension of aluminium chloride (22.9 g, 172 mmol) in anhydrous dichloromethane (100 ml) and acetylchloride (4.5 g, 57.3 mmol)was added a solution of 1-methyl pyrrole-2-carboxaldehyde (5 g, 46 mmol) in anhydrous. dichloromethane (20 ml). The mixture was refluxed for 90 min, poured into ice and stirred until melte... | CC(=O)c1cc(C=O)n(C)c1 | null | 97.8 | null |
1,285,144 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH:7]1[C:16](=O)[C:15]2[C:14]([C:18]([O:20]CC)=O)=[CH:13][CH:12]=[CH:11][C:10]=2[NH:9][CH:8]1[C:23]1[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=1.O.[NH2:34][NH2:35]>CO>[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH:7]1[C:16]2=[N:34][NH:35][C:18](=[O:20])[C:14]3[C... | NN | CCOC(=O)c1cccc2c1C(=O)C(c1nccn1C)C(c1ccc(C(F)(F)F)cc1)N2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CO | null | null | null | null | null | null | null | null | null | 25 | 2 | A mixture of ethyl 3-(1-methyl-1H-imidazol-2-yl)-4-oxo-2-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroquinoline-5-carboxylate (150 mg, 0.34 mmol) in 85% hydrazine monohydrate (4 ml) and methanol (6 mL) was stirred at room temperature for 2 h. The mixture was filtered and washed with water to give the title compound (2... | Cn1ccnc1C1c2n[nH]c(=O)c3cccc(c23)NC1c1ccc(C(F)(F)F)cc1 | null | 18 | null |
1,261,586 | ord_dataset-266f60b4555945d6afb2d2bdf5fa04e0 | null | 2013-01-01T00:02:00 | true | Br[C:2]1[C:3]([F:15])=[C:4]([N:9]2[CH2:13][CH2:12][CH2:11][C:10]2=[O:14])[CH:5]=[CH:6][C:7]=1[F:8].CCN(C(C)C)C(C)C.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[C:67]1([CH2:73][SH:74])[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=C... | O=C1CCCN1c1ccc(F)c(Br)c1F | SCc1ccccc1 | null | [Pd] | CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21 | O=C(/C=C/c1ccccc1)/C=C/c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | C1COCCO1 | null | null | null | null | null | null | null | null | null | 100 | 3 | Intermediate 93 (1 g, 3.62 mmol) in dioxane (30 ml) was stirred under argon. DIPEA (1.26 ml, 7.24 mmol), xantphos (0.126 g, 0.22 mmol) and Pd2(dba)3 (0.099 g, 0.11 mmol) were added and the reaction was heated to 100° C. Phenyl-methanethiol (0.41 ml, 3.44 mmol) was slowly added and the reaction stirred for 3 h. The reac... | O=C1CCCN1c1ccc(F)c(SCc2ccccc2)c1F | null | null | null |
368,477 | ord_dataset-b18df02d6e9345faa0f2dae281a0870a | null | 1997-01-01T00:06:00 | true | C[O:2][C:3]([CH:5]1[CH2:9][CH2:8][CH:7]([C:10]2[NH:18][C:17]3[C:16](=[O:19])[N:15]([CH2:20][CH2:21][CH3:22])[C:14](=[O:23])[N:13]([CH2:24][CH2:25][CH3:26])[C:12]=3[N:11]=2)[CH2:6]1)=[O:4].[OH-].[K+]>C(O)C.O>[C:3]([CH:5]1[CH2:9][CH2:8][CH:7]([C:10]2[NH:18][C:17]3[C:16](=[O:19])[N:15]([CH2:20][CH2:21][CH3:22])[C:14](=[O:... | CCCn1c(=O)c2[nH]c(C3CCC(C(=O)OC)C3)nc2n(CCC)c1=O | 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 | 10 | null | 1.41 g (3.9 mmol) of 8-(3-methyloxycarbonylcyclopentyl)-1,3-dipropyl-7H-purine-2,6-dione are suspended in 10 ml of ethanol and 1 ml of water, 0.77 g of potassium hydroxide are added and the mixture is refluxed for 30 minutes. After cooling to 10° C. the mixture is acidified, the crystals precipitated are suction filter... | CCCn1c(=O)c2[nH]c(C3CCC(C(=O)O)C3)nc2n(CCC)c1=O | null | null | null |
167,976 | ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | null | 1988-01-01T00:02:00 | true | [C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=[O:7])#[N:2].[F:11][C:12]([F:27])([F:26])[C:13]1[CH:14]=[C:15]([NH:20][CH2:21][CH:22](O)[CH2:23][CH3:24])[CH:16]=[CH:17][C:18]=1[Cl:19].O>C1(C)C=CC=CC=1.CS(O)(=O)=O>[C:1]([C:3]1[CH:4]=[C:5]([CH:6]2[N:20]([C:15]3[CH:16]=[CH:17][C:18]([Cl:19])=[C:13]([C:12]([F:27])([... | CCC(O)CNc1ccc(Cl)c(C(F)(F)F)c1 | N#Cc1cccc(C=O)c1 | null | CS(=O)(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | O | null | null | null | null | null | null | null | null | null | null | null | Meta-cyanobenzaldehyde (2.1 g, 0.016 mole) was added to 4.3 g of 1-(3-trifluoromethyl-4-chlorophenylamino)-2-butanol in 50 ml of toluene and 2-3 drops of methane sulfonic acid was added. The mixture was refluxed under a modified Dean-Stark apparatus until no more water came off and the mixture was stripped on a rotary ... | CCC1CN(c2ccc(Cl)c(C(F)(F)F)c2)C(c2cccc(C#N)c2)O1 | null | null | null |
352,216 | ord_dataset-127eb5fdd5b4402e92b51d0b55a5dcb5 | null | 1997-01-01T00:01:00 | true | [CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[OH:12].[Cl-].[Al+3].[Cl-].[Cl-].[C:17](Cl)(=[O:19])[CH3:18]>ClCCl>[CH3:1][C:2]1[CH:11]=[C:10]([C:17](=[O:19])[CH3:18])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[OH:12] | CC(=O)Cl | Cc1ccc2ccccc2c1O | null | [Al+3] | [Cl-] | 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 | 3 | To an ice-cooled solution of 2-methyl-l-naphthol (7.9 g, 0.05 mmol) in dichloromethane, anhydrous aluminum chloride (7.2 g) was slowly added with stirring, followed by slow addition of acetyl chloride (4.7 g) to start reaction. The reaction mixture was stirred at 10° C. or below for 1 h, then at room temperature for 3 ... | CC(=O)c1cc(C)c(O)c2ccccc12 | null | null | null |
1,313,425 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | [I-].[CH2:2]([N+:6]1[C:10]([CH3:11])=[C:9]([CH3:12])[S:8][C:7]=1[CH3:13])[CH2:3][CH2:4][CH3:5].[F:14][C:15]([F:26])([F:25])[C:16]1[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=1[C:18](Cl)=[O:19]>CN(C1C=CN=CC=1)C>[CH2:2]([N:6]1[C:10]([CH3:11])=[C:9]([CH3:12])[S:8]/[C:7]/1=[CH:13]\[C:18]([C:17]1[CH:21]=[CH:22][CH:23]=[CH:24][C:16... | CCCC[n+]1c(C)sc(C)c1C | O=C(Cl)c1ccccc1C(F)(F)F | null | CN(C)c1ccncc1 | [I-] | null | null | 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 | 8 | In a 20 mL vial 3-butyl-2,4,5-trimethylthiazol-3-ium iodide (48 mg in 0.5 mL DMA, 0.16 mmol, 1 equiv.) was added, followed by TEA (38 mg in 0.5 mL DMA, 0.37 mmol, 2.4 equiv.) and the solution went black. DMAP (2 mg in 0.5 mL DMA, 0.016 mmol, 0.1 equiv) was added next, followed by 2-(trifluoromethyl)benzoyl chloride (0.... | CCCCN1C(C)=C(C)S/C1=C\C(=O)c1ccccc1C(F)(F)F | null | null | null |
1,379,289 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | [OH:1][C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[N:5]=[CH:4][N:3]=1.C1C(=O)N([I:17])C(=O)C1>C(O)(=O)C>[CH2:8]([C:6]1[N:5]=[CH:4][NH:3][C:2](=[O:1])[C:7]=1[I:17])[CH3:9] | CCc1cc(O)ncn1 | O=C1CCC(=O)N1I | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | 30 | To a stiffed solution of 70 g (0.56 mol) 4-hydroxy-6-ethyl pyrimidine in acetic acid is added 127 g (0.56 mol) NIS portion wise at RT within 15 min The reaction is stiffed for 30 h at RT until all starting material is consumed. The reaction mixture is diluted with water and the solid product is filtered off and washed ... | CCc1nc[nH]c(=O)c1I | null | null | null |
867,996 | ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | null | 2009-01-01T00:03:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:11]2[CH2:20][C:19]3[C:14](=[N:15][C:16](S(C)=O)=[N:17][CH:18]=3)[NH:13][C:12]2=[O:24])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[CH2:25]([N:27]([CH2:30][CH2:31][CH2:32][NH2:33])[CH2:28][CH3:29])[CH3:26]>>[CH2:25]([N:27]([CH2:28][CH3:29])[CH2:30][CH2:31][CH2:32][NH:33][C:16]1[N:15]=[C:14]2[NH... | CCN(CC)CCCN | COc1cc(OC)cc(N2Cc3cnc(S(C)=O)nc3NC2=O)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Using the general procedure above, 3-(3,5-dimethoxy-phenyl)-7-methanesulfinyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one and 0.1121 g (0.861 mmol) of diethylaminopropylamine were reacted. The residue was chromatographed eluting with acetonitrile/ethanol/triethylamine (8:1:0.5 v/v/v) to give 0.0476 g (40%) of the ti... | CCN(CC)CCCNc1ncc2c(n1)NC(=O)N(c1cc(OC)cc(OC)c1)C2 | null | 40 | null |
398,420 | ord_dataset-a4a191e812a64d0598ea918f047e8da7 | null | 1998-01-01T00:04:00 | true | [NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH2:10][C:11](OCC)=[O:12].CC(C[AlH]CC(C)C)C>C(Cl)Cl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH2:10][CH2:11][OH:12] | CCOC(=O)Cc1cc2ccccc2[nH]1 | null | null | CC(C)C[AlH]CC(C)C | 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 | 0.25 | Ester 4-1 (0.54 g, 2.6 mmol) was dissolved in 13 mL CH2Cl2 at -78°, and DIBAL (1M in CH2Cl2, 5.8 ml, 5.8 mmol) was added dropwise. The mixture was stirred at -78° for 15 min then warmed to RT for 30 min and quenched in sat. aqueous Na/K tartrate. This solution was extracted with EtOAc. The organic layer was washed with... | OCCc1cc2ccccc2[nH]1 | null | null | null |
1,428,353 | ord_dataset-5e6956e6e8c24a168866a253f4a66c6c | null | 2014-01-01T00:05:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([F:8])[CH:7]=1.F[C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N+:17]([C:14]1[CH:15]=[CH:16][C:11]([O:9][C:4]2[CH:5]=[C:6]([F:8])[CH:7]=[C:2]([Cl:1])[CH:3]=2)=[CH:12][CH:13]=1)([O-:19])=[O:18] | O=[N+]([O-])c1ccc(F)cc1 | Oc1cc(F)cc(Cl)c1 | 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 | null | null | To a solution of 3-chloro-5-fluorophenol (1.46 g, 10 mmol) and 1-fluoro-4-nitrobenzene (1.41 g, 10 mmol) in acetonitrile (40 mL) was added potassium carbonate (2.76 g, 20 mmol) and the reaction mixture was heated to reflux for 4 hours. After filtration, the solvent was removed. The residue obtained was washed with n-he... | O=[N+]([O-])c1ccc(Oc2cc(F)cc(Cl)c2)cc1 | null | 88.9 | null |
1,591,682 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [Br:1][C:2]1[C:3]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][C@@H:10]2[C:15]([OH:17])=O)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[Cl:40][C:41]1[CH:46]=[CH:45][C:44]([C@@H:47]([NH2:49])[CH3:48])=[CH:43][CH:42]=1>C1COCC1>[Br:1][C:2]1[C:3]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH:10]2[C:15]([NH:4... | C[C@H](N)c1ccc(Cl)cc1 | O=C(O)[C@H]1COCCN1c1nc(Cl)ncc1Br | null | CCN=C=NCCCN(C)C | Cl | On1nnc2ccccc21 | 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 50 mL round-bottom flask were added (R)-4-(5-bromo-2-chloropyrimidin-4-yl)morpholine-3-carboxylic acid (460 mg, 1.426 mmol), 1-hydroxybenzotriazole (193 mg, 1.426 mmol), and 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (328 mg, 1.711 mmol) in THF (10 mL) to give a beige solution. After 5 minutes (S)-1... | C[C@H](NC(=O)C1COCCN1c1nc(Cl)ncc1Br)c1ccc(Cl)cc1 | null | 72.2 | null |
741,575 | ord_dataset-437aa6654d5044ddaef3346dc4c6e08a | null | 2006-01-01T00:11:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]=[C:11]=[S:12])=[O:9])=[CH:4][CH:3]=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][C:24]=1[O:25][CH3:26])[N:21]=[CH:20][CH:19]=[C:18]2[O:27][C:28]1[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][C:29]=1[CH3:35].C1(C)C=CC=CC=1>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:10][C... | COc1cc2nccc(Oc3ccc(N)cc3C)c2cc1OC | O=C(N=C=S)c1ccc(Cl)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | CCO | null | null | null | null | null | null | null | null | null | 25 | 2 | Commercially available 4-chloro-1-benzenecarbonyl isothiocyanate (50 μl) was dissolved in ethanol (1 ml) to prepare a solution. 4-[(6,7-Dimethoxy-4-quinolyl)oxy]-3-methylaniline (50 mg), toluene (5 ml), and ethanol (1 ml) were added to the solution, and the mixture was stirred at room temperature for 2 hr. The reaction... | COc1cc2nccc(Oc3ccc(NC(=S)NC(=O)c4ccc(Cl)cc4)cc3C)c2cc1OC | null | 64 | null |
1,405,041 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | [Cl:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)/[C:4](=N/S(C2SC=CC=2)(=O)=O)/[CH:3]=1.[CH:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][C:23]=1[S:32]([NH2:35])(=[O:34])=[O:33]>C1COCC1.Cl[Ti](Cl)(Cl)Cl>[Cl:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=... | O=C1C(Cl)=C/C(=N\S(=O)(=O)c2cccs2)c2ccccc21 | NS(=O)(=O)c1ccc2ccccc2c1 | null | Cl[Ti](Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | 5.2.35 N-(3-chloro-4-oxonaphthalen-1(4H)-ylidene)naphthalene-2-sulfonamide (12f) was prepared according to the procedure for (12a) except using naphthalene-2-sulfonamide, TiCl4.2THF and THF as solvent which afforded the title compound 594.8 mg (77.9%) as a yellow solid, m.p.: 200-202° C. | O=C1C(Cl)=CC(=NS(=O)(=O)c2ccc3ccccc3c2)c2ccccc21 | null | null | null |
785,877 | ord_dataset-4ad5db8537994579bef51f16dd8bf0bd | null | 2007-01-01T00:08:00 | true | [C:1]([C:5]1[CH:39]=[CH:38][C:8]([C:9]([N:11]2[C@@H:15]([C:16]3[S:17][CH:18]=[CH:19][CH:20]=3)[C@@H:14]([C:21]3[CH:26]=[N:25][CH:24]=[CH:23][N:22]=3)[CH2:13][C@@:12]2([CH2:34][CH:35]([CH3:37])[CH3:36])[C:27]([O:29]C(C)(C)C)=[O:28])=[O:10])=[CH:7][C:6]=1[O:40][CH3:41])([CH3:4])([CH3:3])[CH3:2].C(O)(C(F)(F)F)=O>>[C:1]([C... | COc1cc(C(=O)N2[C@@H](c3cccs3)[C@@H](c3cnccn3)C[C@@]2(CC(C)C)C(=O)OC(C)(C)C)ccc1C(C)(C)C | 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 | null | null | The tert-butyl ester from stage A was deprotected with TFA in a similar manner to that described in Example 1, to afford the title compound as a solid. | COc1cc(C(=O)N2[C@@H](c3cccs3)[C@@H](c3cnccn3)C[C@@]2(CC(C)C)C(=O)O)ccc1C(C)(C)C | null | null | null |
1,428,634 | ord_dataset-5e6956e6e8c24a168866a253f4a66c6c | null | 2014-01-01T00:05:00 | true | [Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([CH3:11])[CH:3]=1.[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:8])=[C:4]([CH3:11])[CH:3]=1 | Cc1cc(Br)ccc1C(=O)O | C1CCNCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The sub-title compound was prepared by the method of example 18 step a) using 4-bromo-2-methyl benzoic acid and piperidine. | Cc1cc(Br)ccc1C(=O)N1CCCCC1 | null | null | null |
762,572 | ord_dataset-2e58cb8db2bf482bbea23283b7e04488 | null | 2007-01-01T00:03:00 | true | [CH:1]([O:4][C:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:10]2)=[O:6])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:24][C:25]1[CH:29]=[C:28]([C:30]2[S:31][C:32]([Cl:35])=[CH:33][CH:34]=2)[O:27][N:26]=1>CN(C=O)C>[CH:1]([O:4][C:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]... | Clc1ccc(-c2cc(CBr)no2)s1 | CCOC(=O)c1cc2cc(C(=O)OC(C)C)ccc2[nH]1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | 2 | To a solution of 5.24 g 1H-Indole-2,5-dicarboxylic acid 2-ethyl ester 5-isopropyl ester in 80 ml DMF, 456 mg sodium hydride (60% in mineral oil) were added at RT. After stirring for 30 min 5.3 g 3-Bromomethyl-5-(5-chloro-thiophen-2-yl)-isoxazole [prepared by adopting a procedure described by Ewing, William R.; Becker, ... | CCOC(=O)c1cc2cc(C(=O)OC(C)C)ccc2n1Cc1cc(-c2ccc(Cl)s2)on1 | null | null | null |
753,252 | ord_dataset-844a22e1fcab44a5b59c5e2922b2855a | null | 2007-01-01T00:01:00 | true | C[O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17]C)[CH:12]=2)[CH:6]=[C:7]([O:9]C)[CH:8]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=2)[CH:6]=[C:7]([OH:9])[CH:8]=1 | COc1cccc(-c2cc(OC)cc(OC)c2)c1 | null | null | BrB(Br)Br | 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 | 1.5 | To 395 mg (1.62 mmol) of 3,5,3′-trimethoxybiphenyl was added 9 mL of 1.0 M BBr3 in CH2Cl2. The mixture was stirred at ambient temperature for 1.5 h, then poured over 60 mL of ice, and extracted with ethyl acetate (2×25 mL). The combined organic layers were back extracted with water (1×25 mL), then brine (1×25 mL), drie... | Oc1cccc(-c2cc(O)cc(O)c2)c1 | null | 94 | null |
685,345 | ord_dataset-359b8fc87f4244be89d6f02bc5036eac | null | 2005-01-01T00:09:00 | true | [C:1]([O:5][C:6](=[O:22])[NH:7][C:8]1[CH:13]=[C:12]([N:14]([CH3:16])[CH3:15])[C:11]([C:17]([F:20])([F:19])[F:18])=[CH:10][C:9]=1[NH2:21])([CH3:4])([CH3:3])[CH3:2].C([O:27][C:28](=O)[CH2:29][C:30]([C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([C:38]2[C:39]([CH3:44])=[N:40][CH:41]=[CH:42][CH:43]=2)[CH:33]=1)=[O:31])(C)(C)C>>[C:1]... | CN(C)c1cc(NC(=O)OC(C)(C)C)c(N)cc1C(F)(F)F | Cc1ncccc1-c1cccc(C(=O)CC(=O)OC(C)(C)C)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from (2-amino-5-dimethylamino-4-trifluoromethyl-phenyl)-carbamic acid tert-butyl ester (Example J1) (239 mg, 0.75 mmol) and 3-[3-(2-methyl-pyridin-3-yl)-phenyl]-3-oxo-propionic acid tert-butyl ester (Example K5) (234 mg, 0.75 mmol) according to the general procedure M. Obtained as a pink... | Cc1ncccc1-c1cccc(C(=O)CC(=O)Nc2cc(C(F)(F)F)c(N(C)C)cc2NC(=O)OC(C)(C)C)c1 | null | null | null |
1,251,822 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [CH2:1](OC(OCC)CBr)[CH3:2].Br.C([O-])(O)=O.[Na+].[NH2:16][C:17]1[C:18]([OH:24])=[N:19][CH:20]=[C:21]([CH3:23])[N:22]=1>CC(O)C.CCOCC>[CH3:23][C:21]1[N:22]2[CH:1]=[CH:2][N:16]=[C:17]2[C:18]([OH:24])=[N:19][CH:20]=1 | CCOC(CBr)OCC | Cc1cnc(O)c(N)n1 | null | Br | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)O | CCOCC | null | null | null | null | null | null | null | null | null | null | 8 | Bromoacetaldehyde diethyl acetal (12.2 mL, 81.4 mmol) and a solution of 48% HBr (0.94 mL) are heated at reflux for 1.5 hours, then poured into a suspension of NaHCO3 (1.92 g) in propan-2-ol (31.3 mL). The resulting solid is filtered off and 3-amino-5-methyl-pyrazin-2-ol (3.13 g, 25.0 mmol) is added. The solution is ref... | Cc1cnc(O)c2nccn12 | null | 35.4 | null |
412,676 | ord_dataset-fbdd058349aa456f812e3546c84baab5 | null | 1998-01-01T00:09:00 | true | C([Li])(C)(C)C.[CH2:6]([N:12]1[C:25]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[S:19][C:18]2[C:13]1=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].CN(CCN(C)C)C.[CH:34](N1CCCCC1)=[O:35].Cl>C(OCC)(=O)C.C(OCC)C>[CH2:6]([N:12]1[C:25]2[CH:24]=[CH:23][CH:22]=[C:21]([CH:34]=[O:35])[C:20]=2[S:19][C:18]2[C:13... | O=CN1CCCCC1 | CCCCCCN1c2ccccc2Sc2ccccc21 | null | CN(C)CCN(C)C | Cl | [Li]C(C)(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CCOCC | null | null | null | null | null | null | null | null | null | null | 16 | 38.6 ml of tert-butyllithium solution (1.4M in hexane) were slowly added dropwise at -78° under argon and while stirring to a solution of 11.80 g (41.6 mmol) of 10-hexyl-phenothiazine in 125 ml of abs. diethyl ether and 12.5 ml of N,N,N,N-tetramethylethylenediamine. The reaction mixture was stirred at -75° for 16 hours... | CCCCCCN1c2ccccc2Sc2c(C=O)cccc21 | null | 48.8 | null |
822,565 | ord_dataset-ec58fad8331a42c5a67ad75aac6713b4 | null | 2008-01-01T00:05:00 | true | [Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[CH2:11]([N:18]1[C:23](=[O:24])[C:22]2[CH:25]=[C:26]([Br:28])[S:27][C:21]=2[N:20]=[C:19]1[CH:29]([NH:32][CH2:33][CH2:34][N:35]([CH3:37])[CH3:36])[CH2:30][CH3:31])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)C(C)C)(C)C>ClCCl>[CH2:11]([N:18]1[C:23](... | CCC(NCCN(C)C)c1nc2sc(Br)cc2c(=O)n1Cc1ccccc1 | O=C(Cl)c1ccc(Br)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | null | 1 | A solution of 4-bromobenzoyl chloride (19 mg, 0.085 mmol, 1 equiv) in dichloromethane (1 mL) was added to a solution of 3-benzyl-6-bromo-2-(1-{[2-(dimethylamino)ethyl]amino}propyl)thieno[2,3-d]pyrimidin-4(3H)-one (2-8, 38 mg, 0.085 mmol, 1 equiv) and N,N-diisopropylethylamine (11 mg, 0.085 mmol, 1 equiv) in dichloromet... | CCC(c1nc2sc(Br)cc2c(=O)n1Cc1ccccc1)N(CCN(C)C)C(=O)c1ccc(Br)cc1 | null | null | null |
876,443 | ord_dataset-e1c3af9b105b4af09a5171403bbfc06f | null | 2009-01-01T00:04:00 | true | [Br:1]Br.C([O-])(=O)C.[Na+].[CH2:8]([O:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[CH:18][N:19]2[CH2:22][C:23]2[CH:24]=[N:25][C:26]([Cl:29])=[CH:27][CH:28]=2)=[C:15]([NH2:30])[N:14]=1)[CH2:9][CH2:10][CH3:11]>C(O)(=O)C>[Br:1][C:18]1[N:19]([CH2:22][C:23]2[CH:24]=[N:25][C:26]([Cl:29])=[CH:27][CH:28]=2)[C:20]2[C:16]([N:17]=1)=[... | BrBr | CCCCOc1nc(N)c2ncn(Cc3ccc(Cl)nc3)c2n1 | null | CC(=O)[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | Potassium carbonate (2.85 g, 20.6 mmol) and 2-chloro-5-chloromethylpyridine (3.33 g, 20.6 mmol) were added to the DMF solution (125 ml) of 2-butoxyadenine (2.60 g, 12.5 mmol) obtained in Reference Example 1. The resultant was stirred while heating at 80° C. for 2.5 hours. The reaction solution was concentrated under re... | CCCCOc1nc(N)c2nc(Br)n(Cc3ccc(Cl)nc3)c2n1 | null | 62.1 | null |
1,503,840 | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | null | 2014-01-01T00:11:00 | true | [CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][N:16]=1.[C:24]([NH:27][CH2:28][CH2:29][NH2:30])(=[O:26])[CH3:25]>>[C:24]([NH:27][CH2:28][CH2:29][NH:30][C:19](=[O:21])[C:18]1[CH:22]=[CH:23][C:15]([O:14][CH2:13][C:3]2[C... | Cc1onc(-c2ccccc2)c1COc1ccc(C(=O)O)cn1 | CC(=O)NCCN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | As described for example 191, 6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid (200 mg, 0.65 mmol) was converted, using N-acetylethylendiamine instead of 2-aminoethyl isopropylether, to the title compound (170 mg, 67%) which was obtained as a white solid. MS: m/e=395.1 [M+H]+. | CC(=O)NCCNC(=O)c1ccc(OCc2c(-c3ccccc3)noc2C)nc1 | null | 67 | null |
1,251,020 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [O:1]1[C:9]2[CH2:8][CH2:7][NH:6][CH2:5][C:4]=2[C:3]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:2]1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]=[C:23]=[O:24])=[CH:18][C:17]=1[Cl:25]>C1(C)C=CC=CC=1>[Cl:25][C:17]1[CH:18]=[C:19]([NH:22][C:23]([N:6]2[CH2:7][CH2:8][C:9]3[O:1][N:2]=[C:3]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C... | O=C=Nc1ccc(Cl)c(Cl)c1 | CCOC(=O)c1noc2c1CNCC2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | Ethyl 4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridine-3-carboxylate (A-06) (for synthesis see above) (0.5 g, 2.55 mmol) was dissolved in toluene (25 ml), and 1,2-dichloro-4-isocyanatobenzene (0.48 g, 2.55 mmol) was added. The reaction mixture was refluxed for 2 h. Toluene was removed in vacuo, the residue was taken up in et... | CCOC(=O)c1noc2c1CN(C(=O)Nc1ccc(Cl)c(Cl)c1)CC2 | null | null | null |
1,502,445 | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | null | 2014-01-01T00:11:00 | true | [Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[C:4]([F:11])[CH:3]=1.[C:12]([BH3-])#N.[Na+].C=O>C(O)(=O)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[CH3:12])=[C:4]([F:11])[CH:3]=1 | [BH3-]C#N | Fc1cc(Br)cc2[nH]ccc12 | null | C=O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | 25 | 4 | To a stirred solution of 6-bromo-4-fluoro-1H-indole (412 mg, 1.925 mmol) in acetic acid (10.600 mL) at RT was added sodium cyanoborohydride (605 mg, 9.62 mmol). Reaction mixture was stirred for 15 mins Paraformaldehyde (578 mg, 19.25 mmol) was then added and the reaction mixture was stirred at RT for 4 hours. Reaction ... | CN1CCc2c(F)cc(Br)cc21 | null | 40.6 | null |
1,620,159 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[C:4]([CH:19]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C:20]([OH:22])=[O:21])[C:3]=1[CH3:28].[CH:29]([B-](F)(F)F)=[CH2:30].[K+]>>[C:24]([O:23][CH:19]([C:4]1[C:3]([CH3:28])=[C:2]([CH:29]=[CH2:30])[C:11]2[C:6... | C=C[B-](F)(F)F | Cc1c(C(OC(C)(C)C)C(=O)O)c(-c2ccc(Cl)cc2)c2ccccc2c1Br | null | [K+] | null | null | null | null | null | 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-tert-butoxy-2-(1-(4-chlorophenyl)-3-methyl-4-vinylnaphthalen-2-yl)acetic acid (128) was prepared in a similar manner as 2-(4-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetic acid of Example 125, except using potassium vinyltrifluoroborate in the Suzuki coupling reaction, giving the title compound... | C=Cc1c(C)c(C(OC(C)(C)C)C(=O)O)c(-c2ccc(Cl)cc2)c2ccccc12 | null | null | null |
82,283 | ord_dataset-b1023e5ccd7142de9d250aa2e3e124db | null | 1981-01-01T00:06:00 | true | [CH2:1]([NH:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[C:27]([OH:32])(=[O:31])[CH:28]([CH3:30])O.C1(C)C(S(O)(=O)=O)=CC=CC=1>C1(C)C=CC=CC=1>[CH2:1]([NH:17][C:18]1[CH:19]=[CH:20]... | CC(O)C(=O)O | CCCCCCCCCCCCCCCCNc1ccc(C(=O)O)cc1 | null | Cc1ccccc1S(=O)(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | A flask containing 10.0 g (27.7 m moles) 4-(hexadecylamino)benzoic acid, 3.3 g. (36 m moles) lactic acid, 500 mg. toluenesulfonic acid and 500 ml. toluene is equipped with a Soxhlet extractor charged with activated 4 A Linde molecular sieves. The solution is refluxed for 24 hours, during which time the Soxhlet extracto... | CCCCCCCCCCCCCCCCNc1ccc(C(=O)OC(C)C(=O)O)cc1 | null | null | null |
1,070,107 | ord_dataset-5df93261afc143c3ae919a57ff4fc1d4 | null | 2011-01-01T00:07:00 | true | [N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:16]1(=O)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>C(Cl)Cl>[CH:16]1([N:13]2[CH2:14][CH2:15][N:10]([C:7]3[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=3)[CH2:11][CH2:12]2)[CH2:21][CH2:20][CH2:19][CH2:... | O=[N+]([O-])c1ccc(N2CCNCC2)cc1 | O=C1CCCCC1 | 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 | Following the general procedure described above for the synthesis of 11-(4-nitrophenyl)-4-(pentan-3-yl)piperazine, treatment of 1-(4-nitrophenyl)piperazine (5.00 g, 24.1 mmol, 1.0 equiv.) with cyclohexanone (7.10 g, 72.4 mmol, 2.0 eq) in DCM (100 mL) at rt for 72 h provided the title compound as a yellow solid (4.80 g,... | O=[N+]([O-])c1ccc(N2CCN(C3CCCCC3)CC2)cc1 | null | 68.8 | null |
768,987 | ord_dataset-8214eb8444a44dc2900ccb42dbeff15e | null | 2007-01-01T00:05:00 | true | [OH:1][C@H:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C@H:3]1[NH:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([C:29]4[N:33]=[CH:32][N:31](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[N:30]=4)[CH:27]=3)[N:22](C3CCCCO3)[N:21]=2)[CH:15]=1)=[O:13].Cl.C(=O)(O)[O-].[Na+]>O1C... | O=C(N[C@@H]1c2ccccc2C[C@@H]1O)c1cccc(-c2nn(C3CCCCO3)c3ccc(-c4ncn(C(c5ccccc5)(c5ccccc5)c5ccccc5)n4)cc23)c1 | null | null | Cl | O=C([O-])O | [Na+] | 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 | To a stirred solution of N-((1R,2S)-2-hydroxyindanyl)(3-{1-perhydro-2H-pyran-2-yl-5-[1-(triphenyl methyl)(1,2,4-triazol-3-yl)](1H-indazol-3-yl)}phenyl)carboxamide (0.339 g, 0.444 mmol) was added 4.0 M hydrochloric acid in dioxane (10.0 mL) and the mixture stirred at ambient temperature for 20 h. The mixture was cooled ... | O=C(N[C@@H]1c2ccccc2C[C@@H]1O)c1cccc(-c2n[nH]c3ccc(-c4ncn[nH]4)cc23)c1 | null | 22.7 | null |
1,001,286 | ord_dataset-70899a0178cc441482746c093624afa0 | null | 2010-01-01T00:10:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C@H:11]([CH2:20][N:21]([CH2:34][CH3:35])S(C2C=CC=CC=2[N+]([O-])=O)(=O)=O)[CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].C1(S)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C@H:11]([CH2:20][NH:21][CH2:34][C... | CCN(C[C@H](CC(=O)OC(C)(C)C)Nc1ccc(C#N)c(Cl)c1)S(=O)(=O)c1ccccc1[N+](=O)[O-] | null | null | O=C([O-])[O-] | Sc1ccccc1 | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | The crude 1,1-dimethylethyl (3S)-3-[(3-chloro-4-cyanophenyl)amino]-4-{ethyl[(2-nitrophenyl)sulfonyl]amino}butanoate from the previous step (16.2 mmol), phenyl hydrosulfide (1.0 equiv., 1.78 g, 16.2 mmol), and K2CO3 (325 mesh, 3 equiv., 6.71 g, 48.6 mmol) in DMF (60 mL) were stirred at room temperature for 90 min. The r... | CCNC[C@H](CC(=O)OC(C)(C)C)Nc1ccc(C#N)c(Cl)c1 | null | null | null |
763,242 | ord_dataset-2e58cb8db2bf482bbea23283b7e04488 | null | 2007-01-01T00:03:00 | true | [H-].[Na+].C([N:6]1[CH2:10][CH2:9][CH2:8][C:7]1=[O:11])(=O)C.[CH:12](=O)[C:13]1[C:14]([O:19][CH3:20])=[CH:15][CH:16]=[CH:17][CH:18]=1.Cl>O1CCCC1.O>[CH3:20][O:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH:12]=[C:8]1[CH2:9][CH2:10][NH:6][C:7]1=[O:11] | COc1ccccc1C=O | CC(=O)N1CCCC1=O | null | Cl | [H-] | [Na+] | 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 | Sodium hydride (16 g) was suspended in tetrahydrofuran (100 ml) and a solution of N-acetylpyrrolidone (25 g) and o-anisaldehyde (26.8 g) in tetrahydrofuran (100 ml) was added dropwise under ice-cooling. After completion of the reaction, the reaction mixture was poured into water. The mixture was acidified with hydrochl... | COc1ccccc1C=C1CCNC1=O | null | 11.8 | null |
495,416 | ord_dataset-9df8b3ec9c8742b3802e0efaac6f6ef3 | null | 2001-01-01T00:03:00 | true | Cl[C:2]1[N:11]=[C:10]([CH3:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1>C(O)(=O)C>[CH3:12][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([NH:13][C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=2)[N:11]=1 | Cc1nc(Cl)nc2ccccc12 | N#Cc1ccc(N)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | Prepared analogously to Example 30a from 2-chloro-4-methyl-quinazoline and 4-aminobenzonitrile in glacial acetic acid. | Cc1nc(Nc2ccc(C#N)cc2)nc2ccccc12 | null | null | null |
1,724,178 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | [NH2:1][C:2]1[S:3][C:4]([O:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[C:11](OCC)=[O:12])=[CH:5][N:6]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH2:1][C:2]1[S:3][C:4]([O:7][C:8]2[CH:9]=[C:10]([CH2:11][OH:12])[CH:16]=[CH:17][CH:18]=2)=[CH:5][N:6]=1 | CCOC(=O)c1cccc(Oc2cnc(N)s2)c1 | null | null | [Al+3] | [H-] | [Li+] | 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 | Ethyl 3-(2-aminothiazol-5-yl)oxybenzoate (Preparation 20; 2.0 g, 7,575 mmol) in 20 mL of dry THF was added slowly to stirring suspension of lithium aluminium hydride (0.287 g, 7.575 mmol) in 20 mL of dry THF in inert atmosphere and at 0° C. After complete addition the reaction was allowed to stir at room temperature fo... | Nc1ncc(Oc2cccc(CO)c2)s1 | null | null | null |
1,233,823 | ord_dataset-e96f5a2842f14e5380461c234100f05a | null | 2012-01-01T00:12:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:11]=[CH:12]/[C:13]2[CH:25]=[CH:24][C:16]([C:17]([O:19]C(C)(C)C)=[O:18])=[C:15]([NH:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[CH:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(OCC)(=O)C>[C].[Pd].CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]2[CH:25]=[CH:24][C:16](... | COc1ccc(/C=C/c2ccc(C(=O)OC(C)(C)C)c(Nc3ccc(F)cc3)c2)cc1OC | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CO | null | null | null | null | null | null | null | null | null | 25 | 0.5 | To the obtained tert-butyl 4-((E)-2-(3,4-dimethoxyphenyl)vinyl)-2-(4-fluoroanilino)benzoate were added ethyl acetate 1.5 mL, methanol 1.5 mL and 10% palladium-carbon 28 mg sequentially, and it was stirred under hydrogen atmosphere at room temperature for 3 hours and 30 minutes. The solvent was removed under reduced pre... | COc1ccc(CCc2ccc(C(=O)O)c(Nc3ccc(F)cc3)c2)cc1OC | null | null | null |
892,583 | ord_dataset-11068b1e475b4c5b82e56726ab0dddb7 | null | 2009-01-01T00:07:00 | true | [OH:1][C:2]1[C:11]([C:12]([O:14][CH2:15][CH2:16][CH3:17])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.Cl[C:19]1[C:28]2[C:23](=[CH:24][C:25]([O:31][CH3:32])=[C:26]([O:29][CH3:30])[CH:27]=2)[N:22]=[CH:21][CH:20]=1.O>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[CH3:30][O:29][C:26]1[CH:27]=[C:28]2[C:23](=[CH:24][... | CCCOC(=O)c1cc2ccccc2cc1O | COc1cc2nccc(Cl)c2cc1OC | null | CN(C)c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Clc1ccccc1Cl | O | null | null | null | null | null | null | null | null | null | 140 | 12.5 | Propyl 2-hydroxy-3-naphthoate (400 mg), 4-chloro-6,7-dimethoxyquinoline (130 mg), and 4-dimethylaminopyridine (213 mg) were suspended in o-dichlorobenzene (4 ml), and the suspension was stirred at 140° C. for 12.5 hr. The reaction solution was cooled to room temperature, water was then added thereto, and the mixture wa... | CCCOC(=O)c1cc2ccccc2cc1Oc1ccnc2cc(OC)c(OC)cc12 | null | 44.5 | null |
966,709 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | [CH2:1]([N:4]([CH2:21][CH2:22][CH3:23])[C:5]([C:7]1[CH:8]=[C:9]([CH:13]=[C:14]([C:16]2[O:17][CH:18]=[CH:19][N:20]=2)[CH:15]=1)[C:10](O)=[O:11])=[O:6])[CH2:2][CH3:3].C([N:27](CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[O:17]1[CH:18]=[CH:19][N:20]=[C:16]1[C:14]1[CH:15]=[C:7]([C:5]([N:4](... | CCCN(CCC)C(=O)c1cc(C(=O)O)cc(-c2ncco2)c1 | CCN(C(C)C)C(C)C | null | CN(C)C(On1nnc2ccccc21)=[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 | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 0.5 | A solution of 3-[(dipropylamino)carbonyl]-5-(1,3-oxazol-2-yl)benzoic acid 38 (120 mg, 0.38 mmol) in methylene chloride (3.8 mL) containing N,N-diisopropylethylamine (132 μL, 0.76 mmol) and HBTU (151 mg, 0.40 mmol) was stirred at room temperature for 0.5 h. To the above solution was added a solution of the orange oil fr... | CCCN(CCC)C(=O)c1cc(C(N)=O)cc(-c2ncco2)c1 | null | 148.5 | null |
1,276,995 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [C:1]([CH2:3]P(=O)(OCC)OCC)#[N:2].CC(C)([O-])C.[K+].[CH:18]1([CH:23]=O)[CH2:22][CH2:21][CH2:20][CH2:19]1>C1COCC1>[CH:18]1([CH:23]=[CH:3][C:1]#[N:2])[CH2:22][CH2:21][CH2:20][CH2:19]1 | CCOP(=O)(CC#N)OCC | O=CC1CCCC1 | null | CC(C)(C)[O-] | [K+] | 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 | 1 | A solution of diethyl cyanomethylphosphonate (7, 742.5 g, 4.2 mol, 1.1 equiv) in dry THF (5.75 L) was stirred under nitrogen on an ice-water-methanol bath and a solution of 1 M potassium tert-butoxide in THF (4 L, 4.0 mol, 1.05 equiv) was added at such a rate as to keep the temperature below 0° C. After addition of 1 M... | N#CC=CC1CCCC1 | null | 94.8 | null |
1,138,781 | ord_dataset-68715347640045adb1b09e6a04722b0e | null | 2012-01-01T00:03:00 | true | [CH2:1]([O:3][C:4](=[O:24])[C:5]([NH:12][C:13]1[CH:18]=[C:17]([C:19]([O:21][CH3:22])=[O:20])[CH:16]=[CH:15][C:14]=1[F:23])=[CH:6][C:7]([O:9]CC)=O)[CH3:2]>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[CH3:22][O:21][C:19]([C:17]1[C:18]2[C:7](=[O:9])[CH:6]=[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:24])[NH:12][C:13]=2[C:14... | CCOC(=O)C=C(Nc1cc(C(=O)OC)ccc1F)C(=O)OCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccc(-c2ccccc2)cc1 | c1ccc(Oc2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | 300 | 1 | A suspension of 33 (25.0 g, 73.7 mmol) in Dowtherm A (200 mL) was heated to 300° C. over the course of 30 minutes and then stirred at 300° C. for 1 h. The reaction solution was cooled to room temperature and purified by flash chromatography (Hexanes to EtOAc) to afford a white solid (34, 12.1 g, 56.1%). 1H NMR (CDCl3, ... | CCOC(=O)c1cc(=O)c2c(C(=O)OC)ccc(F)c2[nH]1 | null | null | null |
208,602 | ord_dataset-ac1c7aa04d6c4e588e723e3e05721681 | null | 1990-01-01T00:05:00 | true | [C:1]([CH2:4][N:5]1[CH2:10][CH:9]([CH3:11])[C:8](Cl)=[C:7]([C:13]#[N:14])[CH2:6]1)([OH:3])=[O:2].N(C(C)(C)C#N)=NC(C)(C)C#N.C([SnH](CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[C:1]([CH2:4][N:5]1[CH2:10][CH:9]([CH3:11])[CH:8]=[C:7]([C:13]#[N:14])[CH2:6]1)([OH:3])=[O:2] | CC1CN(CC(=O)O)CC(C#N)=C1Cl | null | null | CC(C)(C#N)N=NC(C)(C)C#N | CCCC[SnH](CCCC)CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | To a solution of 43 (24 g, 0.0105 mol) in toluene (400 ml) was added azobisisobutyronitrile (6 g) and tri-n-butyltin hydride (90 g). The mixture was refluxed overnight and then evaporated in vacuo. Elution from a column of silica gel with ethyl acetate - heptane (1:2) gave the title compound as an oil. Yield: 10.4 g (0... | CC1C=C(C#N)CN(CC(=O)O)C1 | null | null | null |
684,716 | ord_dataset-359b8fc87f4244be89d6f02bc5036eac | null | 2005-01-01T00:09:00 | true | [F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl:19][C:20]1[CH:21]=[C:22]([C:27]2[CH:35]=[C:34]3[C:30]([C:31]([NH:44][C:45](=[O:49])[CH2:46][CH2:47][CH3:48])=[N:32][N:33]3COCC[Si](C)(C)C)=[CH:29][CH:28]=2)[CH:23]=[C:24]([Cl:26])[CH:25]=1.C(OCC)(=O)C>O1CCCC1>[Cl:19][C:20]1[CH:21]=[C:22]([C:27]2[CH:35]=[C:34]3[C:30]([C:31]([NH:44][C:... | CCCC(=O)Nc1nn(COCC[Si](C)(C)C)c2cc(-c3cc(Cl)cc(Cl)c3)ccc12 | null | null | CCCC[N+](CCCC)(CCCC)CCCC | [F-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 65 | null | 11.2 cm3 of tetrabutylammonium fluoride as a 1M solution in tetrahydrofuran are added to 1 g of N-[6-(3,5-dichlorophenyl)-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indazol-3-yl]butanamide, described previously, in 20 cm3 of tetrahydrofuran, the reaction medium is then heated at about 65° C. for 18 hours and the heating i... | CCCC(=O)Nc1n[nH]c2cc(-c3cc(Cl)cc(Cl)c3)ccc12 | null | null | null |
635,043 | ord_dataset-de283386b8034acd99fba96d3c7d3227 | null | 2004-01-01T00:04:00 | true | C([NH:4][C:5]1[CH:6]=[C:7]([NH:11][C:12]([NH2:14])=[S:13])[CH:8]=[CH:9][CH:10]=1)(=O)C.Br[CH2:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=O>C(O)C>[C:19]1([C:17]2[N:14]=[C:12]([NH:11][C:7]3[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=3)[NH2:4])[S:13][CH:16]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1 | O=C(CBr)c1ccccc1 | CC(=O)Nc1cccc(NC(N)=S)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of N-(3-acetylaminophenyl)thiourea (0.84 g) and 2-bromoacetophenone (0.84 g) in ethanol (10 ml) was refluxed for 15 minutes. After evaporation of the solvent, 3N hydrochloric acid was added thereto and the mixture was refluxed for 30 minutes. The mixture was made basic with sodium bicarbonate and extracted wi... | Nc1cccc(Nc2nc(-c3ccccc3)cs2)c1 | null | 82 | null |
1,630,894 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | Br[C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[N:11]([C:15]1[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][C:24]([N:27]4[C:39]5[CH:38]=[C:37]6[C:40]([CH3:48])([CH3:47])[C:41]7[C:46]([C:36]6=[CH:35][C:34]=5[C:33]5[C:28]4=[CH:29][CH:30]=[CH:31][CH:32]=5)=[CH:45][CH:44]=[CH:43][CH:42]=7)=[CH:23][CH:22]=3)=[CH:17][CH:16]=1)[... | CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C | CC1(C)c2ccccc2-c2cc3c4ccccc4n(-c4ccc(-c5ccc(-n6c7ccc(Br)cc7c7cc8c(cc76)C(C)(C)c6ccccc6-8)cc5)cc4)c3cc21 | null | CC(=O)[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | ClCCl | null | null | null | null | null | null | null | null | null | null | null | 7.1 g (9.0 mmol) of 4-(7-bromo-12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluoren-10-yl)-4′-(12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluoren-10-yl)biphenyl, 2.5 g (9.85 mmol) of bis(pinacolato)diborane and 2.6 g (26 mmol) of potassium acetate are suspended in 500 ml of dioxane. 0.22 g (0.27 mmol) of 1,1-bi... | CC1(C)c2ccccc2-c2cc3c4ccccc4n(-c4ccc(-c5ccc(-n6c7ccc(B8OC(C)(C)C(C)(C)O8)cc7c7cc8c(cc76)C(C)(C)c6ccccc6-8)cc5)cc4)c3cc21 | null | null | null |
917,231 | ord_dataset-8e59bd24817446f7b1c68e805b8e5f1d | null | 2009-01-01T00:11:00 | true | [C:1]([O:4][C:5]([CH3:8])([CH3:7])[CH3:6])(=[O:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[K+].[Cl:19][C:20]1[S:24][C:23]([C:25](OCC)=[O:26])=[CH:22][CH:21]=1.Cl>C1COCC1.C1(C)C=CC=CC=1>[C:5]([O:4][C:1](=[O:3])[CH2:2][C:25]([C:23]1[S:24][C:20]([Cl:19])=[CH:21][CH:22]=1)=[O:26])([CH3:8])([CH3:7])[CH3:6] | CCOC(=O)c1ccc(Cl)s1 | CC(=O)OC(C)(C)C | null | C[Si](C)(C)[N-][Si](C)(C)C | Cl | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | C1CCOC1 | null | null | null | null | null | null | null | null | null | 0 | null | A 0.25M THF solution of tert-butyl acetate (2.90 g, 25 mmol) is added dropwise to a cold (−78° C.) solution of potassium bis(trimethylsilyl)amide (100 ml of a 0.5M toluene solution) and ethyl 5-chlorothiophene-2-carboxylate (Lancaster)(4.77 g, 25 mmol) in 50 ml of THF. The reaction is allowed to warm to 0° C. over one ... | CC(C)(C)OC(=O)CC(=O)c1ccc(Cl)s1 | null | 68 | null |
869,627 | ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | null | 2009-01-01T00:03:00 | true | C(NC(C)C)(C)C.[Cl:8][C:9]1[CH:17]=[C:16](I)[C:12]2[O:13][CH2:14][O:15][C:11]=2[C:10]=1[NH2:19].[CH3:20][N:21]([CH3:29])[C:22](=[O:28])[CH2:23][O:24][CH2:25][C:26]#[CH:27]>C(OCC)(=O)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>[NH2:19][C:10]1[C:11]2[O:15][CH2:14][O:13][C... | Nc1c(Cl)cc(I)c2c1OCO2 | C#CCOCC(=O)N(C)C | null | Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)NC(C)C | CCOC(C)=O | null | null | null | null | null | null | null | null | null | -20 | null | Bis(triphenylphosphine)palladium(II) chloride (0.236 g), cuprous iodide (0.96 g) and diisopropylamine (0.47 ml) were added to a stirred solution of 5-chloro-7-iodo-1,3-benzodioxol-4-amine (0.500 g) and N,N-dimethyl-2-(prop-2-yn-1-yloxy)acetamide (0.474 g) in ethyl acetate (8 ml) cooled to −20° C. under a nitrogen atmos... | CN(C)C(=O)COCC#Cc1cc(Cl)c(N)c2c1OCO2 | null | 81.9 | null |
1,324,335 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | [OH:1][CH2:2][C:3]1[S:36][C:6]2[N:7]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]4[C:29]([C:34]#[N:35])=[CH:30][CH:31]=[CH:32][CH:33]=4)=[CH:24][CH:23]=3)[C:8](=[O:20])[N:9]([CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:10](=[O:11])[C:5]=2[CH:4]=1.CI.[CH3:39]N(C)C=O.[H-].[Na+]>C(OCC)(=O)C>[CH3:39][O:... | CN(C)C=O | N#Cc1ccccc1-c1ccc(Cn2c(=O)n(CCc3ccccc3)c(=O)c3cc(CO)sc32)cc1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CI | null | null | null | null | null | null | null | null | null | 25 | 2 | To a mixture of 4′-{[6-(hydroxymethyl)-2,4-dioxo-3-(2-phenylethyl)-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}biphenyl-2-carbonitrile (0.45 g), methyl iodide (0.11 mL) and N,N-dimethylformamide (5 mL) was added 60% sodium hydride (0.05 g), and the mixture was stirred at room temperature for 2 hr. The reaction mi... | COCc1cc2c(=O)n(CCc3ccccc3)c(=O)n(Cc3ccc(-c4ccccc4C#N)cc3)c2s1 | null | 77 | null |
1,006,116 | ord_dataset-7448b89163bf426c9d9777809ce24cec | null | 2010-01-01T00:11:00 | true | [C:1]([CH:3]([NH:9][CH:10]=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:21])=CC=1>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].C(Cl)Cl>[NH2:2][C:1]1[S:21][CH:10]=[N:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5] | COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1 | CCOC(=O)C(C#N)NC=O | null | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | ClCCl | null | null | null | null | null | null | null | null | null | null | null | A solution of ethyl 2-cyano-2-formamidoacetate (480 mg, 3.07 mmol) and Lawesson's reagent (746 mg, 1.84 mmol) in toluene (5 mL) was heated up to 80° C. for overnight. The reaction was then diluted with sodium carbonate aqueous solution (20 mL) and methylene chloride (50 mL). Organic phase was washed with brine (20 mL),... | CCOC(=O)c1ncsc1N | null | 37.9 | null |
865,164 | ord_dataset-b8b98725045d45bdbd73512048f4b47e | null | 2009-01-01T00:02:00 | true | C([O:3][C:4](=[O:36])[CH2:5][CH2:6][C:7]1[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=2[C:10]([O:17][CH2:18][C:19]2[C:20]([CH3:35])=[N:21][C:22]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)=[CH:23][CH:24]=2)=[CH:9][CH:8]=1)C.[OH-].[Li+].Cl>C(O)C>[CH3:35][C:20]1[C:19]([CH2:18][O:17][C:10... | CCOC(=O)CCc1ccc(OCc2ccc(-c3ccc(C(F)(F)F)cc3)nc2C)c2c1CCCC2 | null | null | Cl | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 25 | null | 160 mg (0.32 mmol) of the above prepared 3-{4-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-ylmethoxy]-5,6,7,8-tetrahydro-naphthalen-1-yl}-propionic acid ethyl ester was dissolved in 5 ml of ethanol; 1.0 ml of 2N aqueous lithium hydroxide solution was added and the solution was heated to reflux for 1 hour. Then, the... | Cc1nc(-c2ccc(C(F)(F)F)cc2)ccc1COc1ccc(CCC(=O)O)c2c1CCCC2 | null | null | null |
60,882 | ord_dataset-912d62c1690b4ebfbe998c0c9baf88a8 | null | 1979-01-01T00:12:00 | true | [CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:11])[CH3:10])=[CH:5][CH:4]=1)[CH3:2].CO[CH:14](OC)[N:15]([CH3:17])[CH3:16]>>[CH3:14][N:15]([CH3:17])[CH:16]=[CH:10][C:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=1)=[O:11] | CCc1ccc(C(C)=O)cc1 | COC(OC)N(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 | A mixture of 50 g. of 4'-ethylacetophenone and 50 ml. of dimethylformamide dimethylacetal is refluxed for 16 hours. Evaporation gave a thick oil which crystallized on the addition of hexane, m.p. 80°-81° C. | CCc1ccc(C(=O)C=CN(C)C)cc1 | null | null | null |
292,942 | ord_dataset-b90b48a6c23149a1aa2d91b92b1a31e4 | null | 1994-01-01T00:07:00 | true | [C:1](Cl)(=[O:4])[CH2:2][CH3:3].[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[N:14]=[C:15]2[C:20]3[CH2:21][NH:22][CH2:23][CH2:24][C:19]=3[NH:18][C:17](=[O:25])[N:16]2[CH:26]=1.C(N(CC)CC)C>CN(C=O)C>[C:1]([N:22]1[CH2:23][CH2:24][C:19]2[NH:18][C:17](=[O:25])[N:16]3[CH:26]=[C:13]([C:8]4[CH:9]=[CH:10][CH:11]=[CH:12... | O=c1[nH]c2c(c3nc(-c4ccccc4F)cn13)CNCC2 | CCC(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 0 | 0.83 | Propionyl chloride (39 uL, 0.4 mmol) was added to a solution of 2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]pyrido[3,4-e] pyrimidin-5(6H)-one (124 mg, 0.4 mmol) and triethylamine (74 uL, 0.5 mmol) in DMF (2 mL) at room temperature. The reaction mixture was stirred for 50 minutes, and then poured into ice water... | CCC(=O)N1CCc2[nH]c(=O)n3cc(-c4ccccc4F)nc3c2C1 | null | null | null |
788,771 | ord_dataset-530502f8e61e455784f93c5faa45c94b | null | 2007-01-01T00:09:00 | true | [NH2:1][C:2]1[C:3]([C:25]#[N:26])=[N:4][C:5]([C:15]2[CH:20]=[CH:19][C:18](=[O:21])[N:17]([CH:22]([CH3:24])[CH3:23])[N:16]=2)=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[Br:14])[N:7]=1.[O:27]1CCOCC1>Br.CC(O)=O>[NH2:1][C:2]1[C:3]([C:25]([NH2:26])=[O:27])=[N:4][C:5]([C:15]2[CH:20]=[CH:19][C:18](=[O:21])[N:17]([CH:22... | CC(C)n1nc(-c2nc(C#N)c(N)nc2-c2ccccc2Br)ccc1=O | C1COCCO1 | null | Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | 22.5 | 5 | A mixture of 3-amino-5-(2-bromophenyl)-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-pyrazinecarbonitrile (59 mg) in 25% hydrogen bromide in AcOH (0.36 ml) was stirred at 20-25° C. for 5 hours. Dioxane (3 ml) was added to the mixture to give a precipitate. The precipitate was collected by filtration and suspended i... | CC(C)n1nc(-c2nc(C(N)=O)c(N)nc2-c2ccccc2Br)ccc1=O | null | null | null |
111,602 | ord_dataset-ac04cf1ba5724e9b93d39b77e9740b21 | null | 1983-01-01T00:11:00 | true | [CH3:1][N:2]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-])=O)(=[O:5])=[O:4].O.C>C(O)(=O)C.[Fe]>[CH3:1][N:2]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH2:12])(=[O:4])=[O:5] | CN(OCc1ccccc1)S(=O)(=O)c1ccccc1[N+](=O)[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 | 0.33 | To a solution of 88.9 g of the product of Example 33 in 565 ml of 90% aqueous acetic acid was added 83 g of iron powder at 80°-90° in several portions. Water (60 ml) was then added and heating continued for 20 minutes. Charcoal (10 g) was added and the solution filtered through Celite® and concentrated in-vacuo. The re... | CN(OCc1ccccc1)S(=O)(=O)c1ccccc1N | null | 36.3 | null |
403,035 | ord_dataset-55e306db9b6b4befbc22504c12b7113d | null | 1998-01-01T00:06:00 | true | C1(N=C=NC2CCCCC2)CCCCC1.[CH2:16]([C:24]1[CH:25]=[N:26][C:27]([C:30]2[CH:38]=[CH:37][C:33]([C:34]([OH:36])=[O:35])=[CH:32][CH:31]=2)=[N:28][CH:29]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].[CH:39]1([CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49]O)[CH2:43][CH2:42][CH2:41][CH2:40]1>ClCCl.CN(C)C1C=CN=CC=1... | CCCCCCCCc1cnc(-c2ccc(C(=O)O)cc2)nc1 | OCCCCCCC1CCCC1 | null | C(=NC1CCCCC1)=NC1CCCCC1 | CN(C)c1ccncc1 | 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 | 1 | A solution of 0.3 g of N,N'-dicyclohexyl-carbodiimide in 6 ml of dichloromethane is added dropwise at 0° C. within 15 minutes to a solution of 0.201 g of 4-(5-octyl-pyrimidin-2-yl)-benzoic acid, 0.116 g of cyclopentane-hexanol and 0.02 g of 4-dimethylaminopyridine in 10 ml of dichloromethane. The suspension is stirred ... | CCCCCCCCc1cnc(-c2ccc(C(=O)OCCCCCCC3CCCC3)cc2)nc1 | null | null | null |
82,094 | ord_dataset-b1023e5ccd7142de9d250aa2e3e124db | null | 1981-01-01T00:06:00 | true | C(O)(=O)C1C=CC=CC=1.C1C=CC=CC=1.[H-].[C:17]([OH:29])(=[O:28])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]=[CH2:27]>C1COCC1>[C:17]([OH:29])(=[O:28])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27] | C=CCCCCCCCCC(=O)O | null | null | O=C(O)c1ccccc1 | [H-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccccc1 | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 2.5 | Extended reflux of carboxylic acids with excess thexylborane-THF is known to give aldehydes. By contrast TBDA at 0° C. reduces aliphatic carboxylic acids to give predominantly the corresponding alcohols. Benzoic acid in THF is only reduced to the extent of 15% in 48 hours whereas in benzene 1.98 equivalents of hydride ... | CCCCCCCCCCC(=O)O | null | null | null |
1,328,673 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | C([O:3][C:4]([C:6]1[C:7]([S:18][CH2:19][CH3:20])=[N:8][C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:17])=[O:5])C.[OH-].[Na+].Cl>C1COCC1.CO>[Cl:17][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[N:8]=[C:7]([S:18][CH2:19][CH3:20])[C:6]([C:4]([OH:5])=[O:3])=[C:15]2[OH:16] | CCOC(=O)c1c(SCC)nc2c(Cl)cccc2c1O | null | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CO | null | null | null | null | null | null | null | null | null | null | null | To a solution of 8-chloro-2-ethylsulfanyl-4-hydroxy-quinoline-3-carboxylic acid ethyl ester (19.81 g, 63.5 mmol) in THF:MeOH (1:1, 150 mL) at room temperature was added 1N NaOH. The reaction was allowed to stir at reflux for 24 hours, monitoring by HPLC. Upon the completion of the reaction, the mixture was acidified wi... | CCSc1nc2c(Cl)cccc2c(O)c1C(=O)O | null | 95.3 | null |
839,194 | ord_dataset-074f86301ec5441ab3b52d902ac06949 | null | 2008-01-01T00:09:00 | true | C([O:3][C:4](=[O:18])[CH2:5][C:6]1[NH:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[S:8](=[O:17])(=[O:16])[N:7]=1)C.C(Cl)(Cl)Cl>C1COCC1.Cl>[O:17]=[S:8]1(=[O:16])[C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[NH:11][C:6]([CH2:5][C:4]([OH:18])=[O:3])=[N:7]1 | CCOC(=O)CC1=NS(=O)(=O)c2ccccc2N1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 0.25 | A solution of 4c (1.98 g, 7.36 mmol) in THF (10 mL) and 6 N HCl (20 mL) was stirred for 2 days at room temperature. Chloroform (20 mL) was added to the solution to induce precipitation upon vigorous stirring 15 min. The precipitate was collected by vacuum filtration to give 10b (1.50 g, 85%) as a yellow solid. 1H NMR (... | O=C(O)CC1=NS(=O)(=O)c2ccccc2N1 | null | 84.8 | null |
1,578,129 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | C(OC([N:8]1[C:16]2[CH:15]=[C:14]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:13]=[CH:12][C:11]=2[C:10]([CH3:25])([CH3:24])[CH2:9]1)=O)(C)(C)C.[ClH:26]>>[ClH:26].[CH3:24][C:10]1([CH3:25])[C:11]2[CH:12]=[N:13][C:14]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:15][C:16]=2[NH:8][CH2:9]1 | CC(C)(C)OC(=O)N1CC(C)(C)c2cnc(Nc3ccccc3)cc21 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 4 | 3,3-Dimethyl-6-phenylamino-2,3-dihydro-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (60 mg, 0.18 mmol) was treated with HCl (saturated solution in EtOAc) and stirred for 4 h. The mixture was then evaporated to dryness in vacuo to give a colourless gum which was used without further purification. MS: [M+H]+... | CC1(C)CNc2cc(Nc3ccccc3)ncc21 | null | null | null |
1,528,298 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | C[O:2][C:3]([C:5]1[C:6]([OH:35])=[C:7]2[C:12](=[C:13]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)[N:14]=1)[N:11]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:10](=[O:28])[C:9]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[CH:8]2)=[O:4].[OH-].[Na+].CO>C1COCC1>[CH2:21]([N:11]1[C:12]2[C:7](=[C:6]([OH:35... | COC(=O)c1nc(-c2cccnc2)c2c(cc(-c3ccccc3)c(=O)n2Cc2ccccc2)c1O | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CO | null | null | null | null | null | null | null | null | null | 25 | 8 | A mixture of 1-benzyl-5-hydroxy-2-oxo-3-phenyl-8-pyridin-3-yl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester (105 mg, 0.23 mmol), 2 M NaOH (3 mL), MeOH (3 mL) and THF (3 mL) was stirred at r.t. overnight, then concentrated to approximately one-third of its original volume. 1 M HCl was added to acidify th... | O=C(O)c1nc(-c2cccnc2)c2c(cc(-c3ccccc3)c(=O)n2Cc2ccccc2)c1O | null | 101.6 | null |
1,469,537 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | C(OC([N:8]1[CH2:11][C:10]2([CH2:14][N:13]([C:15](=[O:26])[NH:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=3[Cl:25])[CH2:12]2)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:25][C:19]1[CH:20]=[C:21]([Cl:24])[CH:22]=[CH:23][C:18]=1[CH2:17][NH:16][C:15]([N:13]1[CH2:14][C:10]2([CH2:11][NH:8][CH2:9]2)[CH2:12]... | CC(C)(C)OC(=O)N1CC2(CN(C(=O)NCc3ccc(Cl)cc3Cl)C2)C1 | 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 | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 0.5 | 6-(2,4-Dichloro-benzylcarbamoyl)-2,6-diaza-spiro[3.3]heptane-2-carboxylic acid tert-butyl ester (20 mg, 50 μmol) and trifluoroacetic acid (740 mg, 6.49 mmol) were dissolved in dichloromethane (2 mL) and the reaction mixture was stirred for 30 min at ambient temperature. Concentration of the reaction mixture in vacuo af... | O=C(NCc1ccc(Cl)cc1Cl)N1CC2(CNC2)C1 | null | null | null |
1,207,043 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | [F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][CH:7]2[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9][N:8]2[CH2:17][CH2:18][CH2:19][NH2:20])=[CH:4][CH:3]=1.[CH2:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[N:31]=[C:32]=[O:33])[CH3:24]>>[CH2:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[NH:31][C:32]([NH:... | CCc1ccccc1N=C=O | NCCCN1Cc2ccccc2CC1Cc1ccc(F)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The reaction and treatment were carried out in the same manner as in Example 208 using 3-[3-(4-fluorobenzyl)-3,4-dihydroisoquinolin-2(1H)-yl]propanamine obtained in Example 214-b) as a starting material, and using 2-ethylphenyl isocyanate instead of phenyl isocyanate to obtain a title compound as a pale yellow amorphou... | CCc1ccccc1NC(=O)NCCCN1Cc2ccccc2CC1Cc1ccc(F)cc1 | null | null | null |
257,718 | ord_dataset-2369b9b9f44641b1930518c59ae89a95 | null | 1992-01-01T00:11:00 | true | [C:1]1([O:7][C:8]2[C:12]([F:14])([F:13])[C:11]([F:16])([F:15])[C:10]([F:18])([F:17])[C:9]=2Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[H][H]>[Pd]>[CH:1]1([O:7][CH:8]2[CH2:9][C:10]([F:17])([F:18])[C:11]([F:15])([F:16])[C:12]2([F:13])[F:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1 | [H][H] | FC1(F)C(Cl)=C(Oc2ccccc2)C(F)(F)C1(F)F | null | [Pd] | 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 | In a 1.3 l autoclave, 605 g (2 mol) of 2-chloro-3,3,4,4,5,5-hexafluorocyclopentenyl phenyl ether (from Step 1) are suspended in 500 ml of pH 9 buffer (bora/HCl), and the mixture is hydrogenated at 70°-80° C. with 80 bar hydrogen, using 50 g of palladium/charcoal. The catalyst is filtered off, and the filtrate is extrac... | FC1(F)CC(OC2CCCCC2)C(F)(F)C1(F)F | null | null | null |
1,388,612 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | Br[C:2]1[C:3]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.C([Mg]Cl)(C)C.[O:27]1[CH2:32][CH2:31][C:30](=[O:33])[CH2:29][CH2:28]1>C1COCC1>[N:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[NH:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:3]2[C:2]... | O=C1CCOCC1 | Brc1cccnc1Oc1ccc(Nc2ccccn2)cc1 | null | CC(C)[Mg]Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 1 | To a suspension of N-(4-(3-bromopyridin-2-yloxy)phenyl)pyridin-2-amine (1 g, 2.92 mmol) in THF (10 mL) at room temperature was added isopropylmagnesium chloride (5.11 mL, 10.23 mmol). After 1 h stirring at room temperature, another equal amount of isopropylmagnesium chloride was added and the resulting mixture was stir... | OC1(c2cccnc2Oc2ccc(Nc3ccccn3)cc2)CCOCC1 | null | null | null |
174,831 | ord_dataset-4937da99a6a247eb90fa70f0d2eac3db | null | 1988-01-01T00:07:00 | true | [N:1]1([CH2:6][CH:7]([CH2:17][O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH:5]=[CH:4][N:3]=[CH:2]1.[CH2:28](N(CC)CC)[CH3:29].ClC(OCC)=O.C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[N:1]1([CH2:6][CH:7]([CH2:17][O:18][CH2:19][... | COc1ccc(COCC(Cn2ccnc2)OCCCCCC(=O)O)cc1 | CCN(CC)CC | null | CCOC(=O)Cl | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | ClCCl | null | null | null | null | null | null | null | null | null | 0 | 15 | A stirred solution of 6-[2-(1H-imidazol-1-yl)-1-[[(4-methoxyphenyl)methoxy]methyl]ethoxy]hexanoic acid (Example 1c) (10 g, 0.026 mol) and triethylamine (3.0 g, 0.03 mol.) in dichloromethane (100 ml, dried over 4 A molecular sieves) at -50° C. was treated dropwise with ethyl chloroformate (3.2 g, 0.029 mol.). The soluti... | CCOC(=O)CCCCCOC(COCc1ccc(OC)cc1)Cn1ccnc1 | null | null | null |
375,772 | ord_dataset-846d411edee44814931e062174d7ef12 | null | 1997-01-01T00:09:00 | true | [N:1]([C:4]1[CH:12]=[C:11]([CH3:13])[C:7]2[O:8][CH2:9][O:10][C:6]=2[C:5]=1[CH3:14])=[C:2]=[S:3].[CH2:15]([NH2:18])[CH2:16][NH2:17]>C1(C)C=CC=CC=1>[NH2:17][CH2:16][CH2:15][NH:18][C:2](=[S:3])[NH:1][C:4]1[CH:12]=[C:11]([CH3:13])[C:7]2[O:8][CH2:9][O:10][C:6]=2[C:5]=1[CH3:14] | NCCN | Cc1cc(N=C=S)c(C)c2c1OCO2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 1.6 g of 5-isothiocyanato-4,7-dimethyl-1,3-benzodioxole in 35 mL of toluene at 25° C. is added to a solution of 1.89 g of ethylenediamine in 65 mL of toluene. The reaction gradually turns cloudy as a solid precipitates from solution. This solid is collected and dried under vacuum to give 2.0 g of 5-[N'-(2... | Cc1cc(NC(=S)NCCN)c(C)c2c1OCO2 | null | 96.9 | null |
861,165 | ord_dataset-93908aaae836460ebd48d733eccad483 | null | 2009-01-01T00:01:00 | true | [CH3:1][S:2]([O:5][CH2:6][CH3:7])(=[O:4])=[O:3].[C:8]([C:11]1[S:12][C:13]([Cl:16])=[CH:14][CH:15]=1)(=[O:10])[CH3:9]>C1COCC1>[Cl:16][C:13]1[S:12][C:11]([C:8]([OH:10])([CH3:9])[CH2:1][S:2]([O:5][CH2:6][CH3:7])(=[O:4])=[O:3])=[CH:15][CH:14]=1 | CCOS(C)(=O)=O | CC(=O)c1ccc(Cl)s1 | 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 | -78 | 0.5 | A solution of ethyl methanesulphonate (4.97 g) in THF (20 ml) was added dropwise to a solution of lithium hexamethyldisilylamide (42.0 ml of 1M solution in THF plus 20 ml of THF) at −78° C. under nitrogen, and the solution was stirred for 30 min. A solution of 2-acetyl-5-chlorothiophene (6.75 g) in THF (70 ml) was adde... | CCOS(=O)(=O)CC(C)(O)c1ccc(Cl)s1 | null | 95.6 | null |
163,884 | ord_dataset-1385ebf1988241e49636101695ad79e4 | null | 1987-01-01T00:10:00 | true | [CH3:1][NH:2][C:3]1[C:12]2[C:7](=[C:8]([CH2:23][CH2:24][CH3:25])[C:9]3[O:16][C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:14][C:13](=[O:22])[C:10]=3[CH:11]=2)[N:6]=[C:5]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:4]=1.O.[C:32](O)(=[O:34])[CH3:33]>C(OC(=O)C)(=O)C>[CH3:1][N:2]([C:3]1[C:12]2[C:7](=[C:8]([CH2:23][CH2:24... | CC(=O)O | CCCc1c2nc(C(=O)OCC)cc(NC)c2cc2c(=O)cc(C(=O)OCC)oc12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(=O)OC(C)=O | null | null | null | null | null | null | null | null | null | null | null | A solution of diethyl 6-(N-methylamino)-4-oxo-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylate (1.25 g) in acetic acid (25 ml) and acetic anhydride (25 ml) was refluxed for 12 hours, then the solution was poured into water, extracted with ethyl acetate and the extract washed with sodium bicarbonate solution, dried... | CCCc1c2nc(C(=O)OCC)cc(N(C)C(C)=O)c2cc2c(=O)cc(C(=O)OCC)oc12 | null | null | null |
1,650,104 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | N=C=N.[CH:4]([C:7]1[N:8]=[N:9][S:10][C:11]=1[C:12]1[CH:13]=[C:14]([CH:18]=[C:19]([C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][N:22]=2)[CH:20]=1)[C:15](O)=[O:16])([CH3:6])[CH3:5].[CH3:28][C:29]1[N:30]=[CH:31][C:32]([CH2:35][NH2:36])=[N:33][CH:34]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl.CCN(CC)CC>[CH:4]([C:7]1[N... | Cc1cnc(CN)cn1 | Cc1ccc(-c2cc(C(=O)O)cc(-c3snnc3C(C)C)c2)nc1 | null | CCN=C=NCCCN(C)C | N=C=N | On1nnc2ccccc21 | 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 | 3-(4-Isopropyl-[1,2,3]thiadiazol-5-yl)-N-(5-methyl-pyrazin-2-ylmethyl)-5-(5-methyl-pyridin-2-yl)-benzamide was prepared using the carbodiimide-based amide synthesis procedure of example 7 in published patent application US2008004442. Briefly, 3-(4-isopropyl-[1,2,3]thiadiazol-5-yl)-5-(5-methyl-pyridin-2-yl)-benzoic acid... | Cc1ccc(-c2cc(C(=O)NCc3cnc(C)cn3)cc(-c3snnc3C(C)C)c2)nc1 | null | null | null |
471,124 | ord_dataset-cd531114850e4f239b2a3661044ae672 | null | 2000-01-01T00:08:00 | true | [C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[C:20]([CH3:21])[C:15]=2[O:14][N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[CH3:27][S:28]SC>O1CCCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[C:16]2[C:17]([S:28][CH3:27])=[CH:18][CH:19]=[C:20]([CH3:21])[C:15]=2[O:14][N:13... | CSSC | Cc1cccc2c(OCCNC(=O)OC(C)(C)C)noc12 | null | [Li]CCCC | 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 | -70 | null | To a solution of 3-(2-(N-t-butoxycarbonylamino)ethoxy)-7-methyl-1,2-benzisoxazole (0.15 g) in tetrahydrofuran (20 ml) was added butyl lithium (0.75 ml, 1.6M hexane solution) dropwise with stirring at -70° C. under nitrogen atmosphere, and the mixture was stirred at the same temperature for 15 minutes, then followed by ... | CSc1ccc(C)c2onc(OCCNC(=O)OC(C)(C)C)c12 | null | 86.4 | null |
710,313 | ord_dataset-c8069773c1a148aca8ab417108daacc5 | null | 2006-01-01T00:05:00 | true | [CH3:1][C:2]1[CH2:8][C:7]2[CH:9]=[C:10]3[O:15][CH2:14][O:13][C:11]3=[CH:12][C:6]=2[C:5]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[C:18]([CH3:25])[CH:17]=2)=[N:4][N:3]=1.[C:26](Cl)(=[O:28])[CH3:27]>>[C:26]([N:3]1[C:2]([CH3:1])=[CH:8][C:7]2[CH:9]=[C:10]3[O:15][CH2:14][O:13][C:11]3=[CH:12][C:6]=2[C:5]([C:16]2... | CC(=O)Cl | CC1=NN=C(c2ccc([N+](=O)[O-])c(C)c2)c2cc3c(cc2C1)OCO3 | null | null | null | null | null | null | null | 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 3.37 g (10.0 millimoles) of 8-methyl-5-(3-methyl-4-nitro-phenyl)-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepine and 25 ml acetyl chloride is stirred under boiling for 3 hours, whereupon the acid chloride is distilled off in vacuo. The residue is taken up in 100 ml of dichloro methane, washed with 50 ml of a satu... | CC(=O)N1N=C(c2ccc([N+](=O)[O-])c(C)c2)c2cc3c(cc2C=C1C)OCO3 | null | 69 | null |
1,100,382 | ord_dataset-af85e6f81c2d49f08086afd6d9e6959c | null | 2011-01-01T00:10:00 | true | C(OP([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:11]=1)(=O)OCC)C.[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][C:34](=O)[CH2:33][CH2:32]1)=[O:30])([CH3:27])([CH3:26])[CH3:25]>>[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][C:34](=[CH:9][C:10]2[CH:15]=[CH:14][C... | CCOP(=O)(Cc1cccc(OCc2ccccc2)c1)OCC | CC(C)(C)OC(=O)N1CCC(=O)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Following the procedure in Example 1, Step 4, (3-benzyloxy-benzyl)-phosphonic acid diethyl ester (1.0 g, 3.0 mmol, from Step 1) and 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (500 mg, 2.5 mmol) were used to give the title compound (534 mg). | CC(C)(C)OC(=O)N1CCC(=Cc2cccc(OCc3ccccc3)c2)CC1 | null | 56.3 | null |
595,416 | ord_dataset-278fb6af8a994ac69e4d95e6e6eff756 | null | 2003-01-01T00:05:00 | true | [H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:23]=[CH:24][C:25]=1[Cl:26])[CH2:7][N:8]1[C:16]2[C:11](=[C:12]([SH:17])[CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:18]([O:20][CH2:21][CH3:22])=[O:19].[OH:27][CH2:28][CH2:29][CH2:30]Br>CN(C=O)C>[Cl:3][C:4]1[CH:5]=[C:6]([CH:23]=[CH:24][C:25]=1[Cl:26])[CH2:7][N:8]1[C:16]2[C:11](=[C:12]... | OCCCBr | CCOC(=O)c1cc2c(S)cccc2n1Cc1ccc(Cl)c(Cl)c1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | 1 | Sodium hydride (20 mg) was added to a stirred solution of ethyl N-(3,4-dichlorobenzyl)-4-mercaptoindole-2-carboxylate (170 mg) in DMF (7.5 ml). After 1 hour, 3-hydroxyprop-1-yl bromide (89 mg) was added and stirring continued for 16 hours. The reaction mixture was partitioned between water and ethyl acetate and combine... | CCOC(=O)c1cc2c(SCCCO)cccc2n1Cc1ccc(Cl)c(Cl)c1 | null | 15.3 | null |
1,226,127 | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | null | 2012-01-01T00:11:00 | true | [CH3:1][O:2][C:3]1[C:4]([NH:15][C:16](=[O:20])OCC)=[N:5][C:6]2[C:11]([N:12]=1)=[CH:10][C:9]([O:13][CH3:14])=[CH:8][CH:7]=2.[CH3:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1>>[CH3:1][O:2][C:3]1[C:4]([NH:15][C:16]([N:31]2[CH2:32][CH2:33][N:28]([C:23]3[CH:24]=[CH:25][CH:2... | CCOC(=O)Nc1nc2ccc(OC)cc2nc1OC | Cc1ccccc1N1CCNCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Ethyl N-(3,6-dimethoxyquinoxalin-2-yl)carbamate and 1-(2-methylphenyl)piperazine were reacted by the same way with the example 148 to obtain the titled compound (yield, 93%). 1H NMR (300 MHz, CDCl3): δ 2.35 (s, 3H), 2.99-3.02 (m, 4H), 3.73-3.76 (m, 4H), 3.91 (s, 3H), 4.15 (s, 3H), 7.00-7.22 (m, 7H), 7.76-7.79 (m, 1H). | COc1ccc2nc(NC(=O)N3CCN(c4ccccc4C)CC3)c(OC)nc2c1 | null | 93 | null |
552,631 | ord_dataset-ec9decb576c4424c9685993f6262bd9c | null | 2002-01-01T00:07:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:17]=[C:16]([CH:18]=[C:19]([C:26]3[S:27][CH:28]=[CH:29][N:30]=3)[CH2:20][N:21]3[CH:25]=[CH:24][N:23]=[CH:22]3)[CH:15]=[CH:14][C:9]=2[C:10]([O:12]C)=[O:11])=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:17]=[C:16]([CH:18]=[C:19]([C:26]3[S:27][CH:28]=[CH:29][... | COC(=O)c1ccc(C=C(Cn2ccnc2)c2nccs2)cc1-c1ccc(F)cc1 | 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 | null | null | A solution of methyl 2-(4-fluorophenyl)-4-[2-(thiazol-2-yl)-3-(imidazol-1-yl)prop-1-en-1-yl]benzoate (E and Z isomers) (1.99 g; 5 mmol) in methanol (20 ml) was refluxed with 2N aqueous sodium hydroxide solution (5 ml; 10 mmol) for 2 hours. Methanol was then evaporated and the solution acidified to pH 5.5 with 6N HCl. T... | O=C(O)c1ccc(C=C(Cn2ccnc2)c2nccs2)cc1-c1ccc(F)cc1 | null | 80 | null |
1,080,296 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | C(O)(=O)C.CO[CH:7]1[CH2:11][CH2:10][CH:9](OC)O1.[NH2:14][C:15]1[CH:16]=[C:17]([CH:36]=[CH:37][CH:38]=1)[C:18]([NH:20][C:21]1[CH:29]=[C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:27]=[CH:26][C:22]=1[C:23]([OH:25])=[O:24])=[O:19].C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[C:30]1([C:28]2[CH:27]=[CH:26][C:22]([C:23]([OH:2... | COC1CCC(OC)O1 | Nc1cccc(C(=O)Nc2cc(-c3ccccc3)ccc2C(=O)O)c1 | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 90 | 0.08 | 0.25 mL of acetic acid and 4.3 μL of 2,5-dimethoxytetrahydrofuran were added sequentially to 10 mg of 2-(3-aminobenzamido)-4-phenylbenzoic acid at room temperature and stirred at 90° C. for 5 minutes. Ethyl acetate and a saturated sodium hydrogen carbonate aqueous solution were added to the reaction mixture. The organi... | O=C(Nc1cc(-c2ccccc2)ccc1C(=O)O)c1cccc(-n2cccc2)c1 | null | null | null |
632,282 | ord_dataset-de283386b8034acd99fba96d3c7d3227 | null | 2004-01-01T00:04:00 | true | Cl.[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH3:16])=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[CH:5][CH:4]=1.[NH2:17][C:18]1[CH:19]=[C:20]([NH:25][C:26](=[O:37])[C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH3:36])[CH:28]=2)[CH:21]=[CH:22][C:23]=1[CH3:24]>C(O)(C)C>[ClH:2].[CH3:24][C:23]1[CH:22]=[CH:21][C... | COc1ccc(C(=O)Nc2ccc(C)c(N)c2)cc1OC | COc1cc2nccc(Cl)c2cc1OC | null | Cl | null | 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 | 85 | null | Hydrochloric acid (0.15 ml) was added to a mixture of 4-chloro-6,7-dimethoxy quinoline (335 mg) and N-(3-amino-4-methylphenyl)-3,4-dimethoxybenzamide (472 mg) in isopropanol (8 ml) and heated to 85° C. for 18 hours. After cooling to room temperature the precipitated solid was isolated and washed with isohexane to yield... | COc1ccc(C(=O)Nc2ccc(C)c(Nc3ccnc4cc(OC)c(OC)cc34)c2)cc1OC | null | 23.6 | null |
1,090,842 | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | null | 2011-01-01T00:09:00 | true | [Cl:1][C:2]1[CH:6]=[CH:5][S:4][CH:3]=1.[Li]CCCC.[Cl:12][C:13]1[N:18]=[C:17]([Cl:19])[CH:16]=[CH:15][N:14]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1COCC1.CCOCC>[Cl:12][C:13]1[N:18]=[C:17]([Cl:19])[CH:16]=[C:15]([C:3]2[S:4][CH:5]=[CH:6][C:2]=2[Cl:1])[N:14]=1 | Clc1ccnc(Cl)n1 | Clc1ccsc1 | null | N#CC1=C(C#N)C(=O)C(Cl)=C(Cl)C1=O | [Li]CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | C1CCOC1 | null | null | null | null | null | null | null | null | null | 0 | 0.75 | To a solution of 3-chlorothiophene (384 mg, 3.0 mmol) in THF (6 mL) at −78° C. was added n-BuLi (1.6 M, 2 mL) and the resulting mixture stirred for 45 minutes. The resulting product was added to a solution of 2,4-dichloropyrimidine (430 mg, 2.9 mmol) in ether (10 mL) at −30° C. and the resulting mixture stirred for 30 ... | Clc1cc(-c2sccc2Cl)nc(Cl)n1 | null | null | null |
168,295 | ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | null | 1988-01-01T00:02:00 | true | C([C:3]1[C:4]([N:12]2[C:16](=[O:17])[C:15]3=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]3[C:13]2=[O:22])=[N:5][CH:6]=[C:7]([CH:9]([Cl:11])[Cl:10])[N:8]=1)=O.Cl.[NH2:24][OH:25].O>CS(C)=O>[N:24](=[C:3]1[N:8]=[C:7]([CH:9]([Cl:11])[Cl:10])[CH:6]=[N:5][CH:4]1[N:12]1[C:16](=[O:17])[C:15]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]2[C:13]1... | NO | O=Cc1nc(C(Cl)Cl)cnc1N1C(=O)c2ccccc2C1=O | null | Cl | 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 | 70 | 0.25 | A solution of 10 g of 3-formyl-5-dichloromethyl-2-phthalimidopyrazine in 50 ml of dimethyl sulfoxide was heated at 50° C., 7 g of hydroxylamine hydrochloride were added, and the mixture was stirred for 15 minutes at 70° C. Thereafter, 700 ml of water were added to the reaction solution, the mixture was filtered and the... | O=C1c2ccccc2C(=O)N1C1N=CC(C(Cl)Cl)=NC1=NO | null | 67.4 | null |
132,441 | ord_dataset-232d09663ed349c2a1fb1f05d411eae0 | null | 1985-01-01T00:07:00 | true | [CH2:1]([N+:5]([CH2:14][CH2:15][CH2:16][CH3:17])([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].Cl[N:19]([CH:29]1[CH2:32][N:31]([S:33]([OH:36])(=[O:35])=[O:34])[C:30]1=[O:37])[C:20](=[O:28])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[K].C([N+](CCCC)(CCCC)CCCC)CCC.O=C1C(N... | O=C(Cc1ccccc1)N(Cl)C1CN(S(=O)(=O)O)C1=O | O=C(OCc1ccccc1)N(Cl)C1CN(S(=O)(=O)[O-])C1=O | null | CCCC[N+](CCCC)(CCCC)CCCC | [K] | null | null | null | null | 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 80, but substituting N-chloro-N-(2-oxo-1-sulfo-3-azetidinyl)-2-phenylacetamide, tetrabutylammonium salt (see Example 47A for preparation of the corresponding potassium salt) for 2-oxo-3-[N-chloro-N-[(phenylmethoxy)carbonyl]amino]-1-azetidinesulfonic acid, tetrabutylammonium salt, yiel... | CCCCOC1(NC(=O)Cc2ccccc2)CN(S(=O)(=O)O)C1=O | null | null | null |
947,647 | ord_dataset-3feb2a95f66e4706a4a50c977ccd9bf8 | null | 2010-01-01T00:04:00 | true | [C:1]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[CH:9]([C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1)=O.N1CCCCC1>C(O)C>[C:1](/[C:3](=[CH:9]/[C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1)/[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2] | N#Cc1ccc(C=O)cc1 | CCOC(=O)CC#N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCNCC1 | CCO | null | null | null | null | null | null | null | null | null | 25 | 2 | Ethyl cyanoacetate (2.59 g, 22.88 mmol) and 4-formylbenzonitrile (3.0 g, 22.88 mmol) are dissolved in ethanol (100 ml). Piperidine (100 mg, 1.14 mmol) is added, and the reaction mixture is stirred at room temperature for 2 hours. The solvent is removed in vacuo, and the residue is purified by column chromatography on s... | CCOC(=O)/C(C#N)=C\c1ccc(C#N)cc1 | null | null | null |
1,075,295 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | [N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:13]3[CH2:22][CH2:21][C:16]4(OCC[O:17]4)[CH2:15][CH:14]=3)=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl>CC(C)=O>[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:13]3[CH2:22][CH2:21][C:16](=[O:17])[CH2:15][CH:14]=3)=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2] | O=[N+]([O-])c1ccc2c(C3=CCC4(CC3)OCCO4)c[nH]c2c1 | null | null | Cl | null | 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 | null | 14 | A solution of compound 118 (3.9 g, 12.986 mmol) in acetone (50 mL) was treated with 10% aq. HCl (50 mL) at room temperature and stirred for over night (14 h). Solvent was evaporated and crude was basified using 10% aq. NH4OH solution (100 mL). The solid was filtered off, washed with 10% NH4OH solution (20 mL), water (2... | O=C1CC=C(c2c[nH]c3cc([N+](=O)[O-])ccc23)CC1 | null | 84.4 | null |
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