original_index int64 2 1.77M | extracted_from_file stringclasses 489
values | date_of_experiment timestamp[ns]date | grant_date timestamp[ns]date 1976-01-01 00:01:00 2016-01-01 00:09:00 | is_mapped bool 1
class | rxn_str stringlengths 87 6.12k | reactant_000 stringlengths 1 902 | reactant_001 stringlengths 1 902 ⌀ | reactant_002 null | agent_000 stringlengths 1 540 ⌀ | agent_001 stringlengths 1 852 ⌀ | agent_002 stringlengths 1 247 ⌀ | agent_003 null | agent_004 null | agent_005 null | agent_006 null | agent_007 null | agent_008 null | agent_009 null | agent_010 null | agent_011 null | agent_012 null | agent_013 null | agent_014 null | agent_015 null | agent_016 null | solvent_000 stringclasses 446
values | solvent_001 stringclasses 405
values | solvent_002 null | solvent_003 null | solvent_004 null | solvent_005 null | solvent_006 null | solvent_007 null | solvent_008 null | solvent_009 null | solvent_010 null | temperature float64 -230 30.1k ⌀ | rxn_time float64 0 2.16k ⌀ | procedure_details stringlengths 8 24.5k | product_000 stringlengths 1 484 | product_001 null | yield_000 float64 0 90,205,156,600B ⌀ | yield_001 float64 0 100M ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
1,233,601 | ord_dataset-e96f5a2842f14e5380461c234100f05a | null | 2012-01-01T00:12:00 | true | [CH2:1]([N:8]1[C:13](=O)[CH2:12][C:11]([CH3:16])([CH3:15])/[C:10](=[N:17]/O)/[C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH3:15])([CH3:16])[CH:10]([NH2:17])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1 | CC1(C)CC(=O)N(Cc2ccccc2)C(=O)/C1=N\O | 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 | 25 | 2 | To a solution of (Z)-1-benzyl-4,4-dimethylpiperidine-2,3,6-trione 3-oxime (490 mg, 1.88 mmol) in THF (5 mL) at 0° C. was slowly added LiAlH4 (1.0M in THF, 9.4 mL, 9.4 mmol). After the addition, the reaction mixture was warmed to room temperature and stirred for 2 h then heated at 60° C. overnight. The reaction mixture ... | CC1(C)CCN(Cc2ccccc2)CC1N | null | 51.2 | null |
1,721,748 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | Br[C:2]1[S:3][C:4]([NH:33]C(=O)OC(C)(C)C)=[C:5]([C:7](=[O:32])[NH:8][C:9]2[CH:10]=[N:11][N:12]([CH3:31])[C:13]=2[C@@H:14]2[CH2:20][CH2:19][C@@H:18]([NH:21]C(OC(C)(C)C)=O)[C@@H:17]([O:29][CH3:30])[CH2:16][O:15]2)[N:6]=1.[F:41][C:42]1[C:47]([F:48])=[CH:46][CH:45]=[CH:44][C:43]=1B(O)O>>[NH2:33][C:4]1[S:3][C:2]([C:46]2[CH:... | CO[C@H]1CO[C@H](c2c(NC(=O)c3nc(Br)sc3NC(=O)OC(C)(C)C)cnn2C)CC[C@H]1NC(=O)OC(C)(C)C | OB(O)c1cccc(F)c1F | null | null | null | null | null | null | null | 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 for Example 101 starting from tert-butyl N-[2-bromo-4-[[5-[(2S,5R,6R)-5-(tert-butoxycarbonylamino)-6-methoxy-oxepan-2-yl]-1-methyl-pyrazol-4-yl]carbamoyl]thiazol-5-yl]carbamate (Intermediate 98), and replacing 3,6-dihydro-2H-pyran-4-boronic acid pinacol ester with (2,3-difluorophenyl)boronic aci... | CO[C@H]1CO[C@H](c2c(NC(=O)c3nc(-c4cccc(F)c4F)sc3N)cnn2C)CC[C@H]1N | null | null | null |
502,805 | ord_dataset-d673d02cdac14dba9ff59f12845a4f37 | null | 2001-01-01T00:05:00 | true | CC([O-])(C)C.[K+].[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:10][CH:9]=1.[CH:22]1(Br)[CH2:26][CH2:25][CH2:24][CH2:23]1>CN(C=O)C>[CH:22]1([CH:14]([C:11]2[CH:10]=[CH:9][C:8]([CH3:7])=[CH:13][CH:12]=2)[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:... | BrC1CCCC1 | Cc1ccc(CC(=O)OC(C)(C)C)cc1 | null | CC(C)(C)[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 0 | 0.5 | 33.5 g (0.3 mol) of potassium tert-butylate are initially introduced into 100 ml of anhydrous DMF at 0° C., and 51.6 g (0.25 mol) of tert-butyl 4-methylphenyl-acetate in 250 ml of anhydrous DMF are added dropwise. The mixture is stirred at 0° C. for 30 minutes, 32.2 ml (0.3 mol) of cyclopentyl bromide in 150 ml of anhy... | Cc1ccc(C(C(=O)OC(C)(C)C)C2CCCC2)cc1 | null | null | null |
789,743 | ord_dataset-530502f8e61e455784f93c5faa45c94b | null | 2007-01-01T00:09:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][C:10]([NH:12][C@@H:13]1[CH2:18][CH2:17][C@H:16]([N:19]2[CH:23]=[C:22]([C:24](O)=[O:25])[N:21]=[N:20]2)[CH2:15][CH2:14]1)=[O:11].[NH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:1][... | O=C(Cc1c(F)cccc1Cl)N[C@H]1CC[C@@H](n2cc(C(=O)O)nn2)CC1 | C1CCNCC1 | null | CN(C)C(On1nnc2ccccc21)=[N+](C)C | F[B-](F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 25 | 1 | To a solution under Ar of 1-{cis-4-[2-(2-chloro-6-fluoro-phenyl)-acetylamino]-cyclohexyl}-1H-[1,2,3]triazole-4-carboxylic acid (100 mg) in DMF (4 ml) were added piperidine (22 mg), TBTU (93 mg) and DIPEA (0.13 ml). The solution was stirred 1 h at RT before partitioning it between EtOAc (50 ml) and H2O (50 ml). The orga... | O=C(Cc1c(F)cccc1Cl)N[C@H]1CC[C@@H](n2cc(C(=O)N3CCCCC3)nn2)CC1 | null | 96.8 | null |
706,880 | ord_dataset-c8069773c1a148aca8ab417108daacc5 | null | 2006-01-01T00:05:00 | true | [Cl:1][C:2]1[C:7]([C:8]2[C:12]([C:13]([OH:15])=O)=[C:11]([CH3:16])[O:10][N:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:17]([O:24][C:25](=[O:35])[NH:26][CH2:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH:30]([NH2:34])[CH2:29]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl.CN(C)CCCN=C=NCC.ON1C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)... | NC1CCCC(CNC(=O)OCc2ccccc2)C1 | Cc1onc(-c2cccnc2Cl)c1C(=O)O | null | CCN=C=NCCCN(C)C | Cl | On1nnc2cccnc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 25 | null | Combine 3-(2-chloro-pyridin-3-yl)-5-methyl-isoxazole-4-carboxylic acid (0.50 g, 0.0021 mol) with (3-amino-cyclohexylmethyl)-carbamic acid benzyl ester (0.63 g, 0.0021 mol), 1-[3-(dimethyl-amino)propyl]-3-ethylcarbodiimide hydrochloride (0.40, 0.0021 mol), 1-hydroxy-7-azabenzo-triazole (0.29 g, 0.0021 mol), and N,N-diis... | Cc1onc(-c2cccnc2Cl)c1C(=O)NC1CCCC(CNC(=O)OCc2ccccc2)C1 | null | null | null |
722,085 | ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | null | 2006-01-01T00:08:00 | true | C(OC([NH:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[N:25]=[C:24]([NH:26][C:27]3[NH:28][N:29]=[C:30]([CH3:32])[CH:31]=3)[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=2)=[CH:11][CH:10]=1)=O)(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[N:25]=[C:24]([NH:26][C:27]3[NH:28][N:29... | Cc1cc(Nc2nc(Nc3ccc(NC(=O)OC(C)(C)C)cc3)nc3ccccc23)[nH]n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 2 | A solution of [2-(4-tert-Butoxycarbonylamino-phenylamino)-quinazolin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine (IIc-60, 100 mg, 0.232 mmol) in a mixture of DCM/TFA (5/1, 12 mL) was stirred for 2 hours at room temperature. The solvents were removed in vacuo and the residue triturated in aqueous K2CO3. The resulting solid w... | Cc1cc(Nc2nc(Nc3ccc(N)cc3)nc3ccccc23)[nH]n1 | null | null | null |
823,873 | ord_dataset-0ca5627a13c049a99463095023b09fe5 | null | 2008-01-01T00:06:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH:16]=[CH:17][N:18]3[CH3:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li]C(C)(C)C.[C:29]1([S:35](F)(=[O:37])=[O:36])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2... | Cn1ccc2c(N3CCN(C(=O)OC(C)(C)C)CC3)cccc21 | O=S(=O)(F)c1ccccc1 | null | [Li]C(C)(C)C | 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 | -75 | 0.5 | To a −75° C. solution of 4-(1-methyl-1H-indol-4-yl)-piperazine-1-carboxylic acid tert-butyl ester compound 3-1 (330 mg, 1.05 mmol) in THF (25 mL) was slowly added t-BuLi (1.2 mL, 2.1 mmol). The reaction mixture was stirred for 30 minutes at −75° C. then warmed in an ice bath for 15 min. The reaction was re-cooled to −7... | Cn1c(S(=O)(=O)c2ccccc2)cc2c(N3CCN(C(=O)OC(C)(C)C)CC3)cccc21 | null | 40 | null |
1,147,260 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | [NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.CCN(C(C)C)C(C)C.[Cl:21][C:22]1[CH:23]=[C:24]([CH:29]=[CH:30][C:31]=1[Cl:32])[CH2:25][N:26]=[C:27]=[O:28].[N-]=C=O>CN1C(=O)CCC1.CN(C1C=CN=CC=1)C>[Cl:21][C:22]1[CH:23]=[C:24]([CH:29]=[CH:30][C:31]=1[Cl:32])[CH2:25][NH:26][C:27](=[O:28])[NH:1][C:2]1... | O=C=NCc1ccc(Cl)c(Cl)c1 | CCOC(=O)c1csc(N)n1 | null | CN(C)c1ccncc1 | [N-]=C=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN1CCCC1=O | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 160 | null | The commercial starting material ethyl 2-aminothiazole-4-carboxylate (2 mmol) was dissolved in NMP and DIEA (1 equivalent) was added followed by addition of the 3,4-dichloro-benzyl isocyanate (1 equivalent). Add 5% DMAP. Heat at 160° C. under microwave irradiation for 30 min Added additional isocyanate reagent (1.0 eq)... | CCOC(=O)c1csc(NC(=O)NCc2ccc(Cl)c(Cl)c2)n1 | null | null | null |
558,096 | ord_dataset-f483e698250b4da0a84f425c7bfa965a | null | 2002-01-01T00:08:00 | true | [Si]([O:8][C@@H:9]1[C@@:44]2([CH3:45])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:43]2[CH2:42][CH2:41][C@@:40]2([CH3:46])[C@H:17]3[CH2:18][CH:19]=[C:20]2[C@H:21]([O:23][CH2:24]/[CH:25]=[CH:26]\[C:27]([CH2:38][CH3:39])([O:30][Si](CC)(CC)CC)[CH2:28][CH3:29])[CH3:22])[CH2:12][C@@H:11]([O:47][Si](C(C)(C)C)(C)C)[CH2:10]1)(C(C)(C)C)... | CCC(/C=C\CO[C@H](C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C)(CC)O[Si](CC)(CC)CC | null | null | CCCC[N+](CCCC)(CCCC)CCCC | [F-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | By the same procedure as in Example 9, 1α,3β-bis(tert-butyldimethylsilyloxy)-20(R)-{(Z)-(4-ethyl-4-triethylsilyloxy-2-hexenyloxy)}pregna-5,7,16-triene (82.0 mg, 0.103 mmol), tetrahydrofuran (3 ml) and 1M tetra-n-butylammonium fluoride solution in tetrahydrofuran (2 ml) were reacted (heating under reflux for 5.5 hours) ... | CCC(O)(/C=C\CO[C@H](C)C1=CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C)CC | null | 98 | null |
447,198 | ord_dataset-a4f0b79f6b9847168861270b79f84afa | null | 1999-01-01T00:11:00 | true | FC(F)(F)C(O)=O.C(O[C:13](=O)[N:14]([C@@H:16]([C:28](=[O:45])[N:29]([C@H:31]([CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH2:32][NH:33][S:34]([CH3:37])(=[O:36])=[O:35])[CH3:30])[CH2:17][C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=1)C)(C)(C)C>ClCCl>[CH3:30][N:29]([C@H:31]([CH2:... | CN(C(=O)[C@@H](Cc1ccc2ccccc2c1)N(C)C(=O)OC(C)(C)C)[C@@H](CNS(C)(=O)=O)Cc1ccccc1 | 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 | 0 | 0.25 | At 0° C., trifluoroacetic acid (4 ml) was added to a solution of N-((1R)-1-(N-((1R)-1-benzyl-2-((methylsulfonyl)amino)ethyl)-N-methylcarbamoyl)-2-(2-naphthyl)ethyl)-N-methylcarbamic acid tert-butylester (997 mg, 1.8 mmol) in dichloromethane (4 ml). The solution was stirred for 15 min at 0° C. The solvent was removed in... | CN[C@H](Cc1ccc2ccccc2c1)C(=O)N(C)[C@@H](CNS(C)(=O)=O)Cc1ccccc1 | null | 79.1 | null |
1,112,045 | ord_dataset-375a420ee9b042918ddca20f02df37d3 | null | 2011-01-01T00:11:00 | true | Cl[C:2]1[O:3][C:4]([CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][CH3:25])=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[N:6]=1.[CH2:26]([C:29]1[NH:30][CH:31]=[CH:32][N:33]=1)[CH2:27][CH3:28].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]2[N... | COc1ccccc1OCCCc1oc(Cl)nc1-c1ccc(Cl)cc1 | CCCc1ncc[nH]1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 125 | 4 | A mixture of 2-chloro-4-(4-chlorophenyl)-5-[3-(2-methoxyphenoxy)propyl]oxazole (500 mg), 2-propylimidazole (1.10 g), potassium carbonate (1.38 g) and N,N-dimethylformamide (10 ml) was stirred at 120-130° C. for 4 hours. The reaction mixture was poured into water (100 ml), the resulting solid precipitate was filtered, a... | CCCc1nccn1-c1nc(-c2ccc(Cl)cc2)c(CCCOc2ccccc2OC)o1 | null | 39 | null |
1,616,298 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [C:1]([O:7][CH2:8][C@H:9]([C:15]1[C:37]([CH3:38])=[CH:36][C:18]2[N:19]=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH:23]=3)[S:21][C:17]=2[C:16]=1Br)[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[Cl:40][C:41]1[CH:46]=[CH:45]... | Cc1cc2nc(-c3cccc(OCc4ccccc4)c3)sc2c(Br)c1[C@@H](COC(=O)C(C)(C)C)OC(C)(C)C | OB(O)c1ccc(Cl)cc1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 120 | null | The mixture of (S)-2-(2-(3-(benzyloxy)phenyl)-7-bromo-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalate (100 mg, 0.164 mmol), 4-chlorophenylboronic acid (38 mg, 0.246 mmol), 2N K2CO3 (400 μL), Pd(PPh3)4 (18 mg, 0.016 mmol) in dioxane in sealed tube was heated at 120° C. After the reaction is finished, the react... | Cc1cc2nc(-c3cccc(OCc4ccccc4)c3)sc2c(-c2ccc(Cl)cc2)c1[C@@H](COC(=O)C(C)(C)C)OC(C)(C)C | null | 97.8 | null |
775,093 | ord_dataset-bf316bf78f4f45d4b275959c08104b7c | null | 2007-01-01T00:06:00 | true | [OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([Br:16])=[N:7][N:8]([CH:13]([CH3:15])[CH3:14])[C:9]2=[O:12])=[CH:4][CH:3]=1.[C:17]([O-])([O-])=O.[K+].[K+].CI>O1CCCC1>[CH3:17][O:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([Br:16])=[N:7][N:8]([CH:13]([CH3:14])[CH3:15])[C:9]2=[O:12])=[CH:4][CH:3]=1 | O=C([O-])[O-] | CC(C)n1nc(Br)c2ccc(O)cc2c1=O | null | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CI | null | null | null | null | null | null | null | null | null | null | null | To a stirred solution of 7-Hydroxy-2-Isopropyl-4-bromo-2H-phthalazin-1-one (0.4 g, 1.4 mmol) in tetrahydrofuran (THF) (5 ml) were added successively, K2CO3 (0.59 g, 4.3 mmol) and methyl iodide (0.22 g, 1.55 mmol) and the mixture was heated to reflux for 24 hours. After this time, LC-MS indicated complete consumption of... | COc1ccc2c(Br)nn(C(C)C)c(=O)c2c1 | null | 76.9 | null |
1,670,705 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]#[C:8][C:9]12[CH2:18][CH:13]3[CH2:14][CH:15]([CH2:17][C:11]([NH:19]C(=O)OC(C)(C)C)([CH2:12]3)[CH2:10]1)[CH2:16]2.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]#[C:8][C:9]12[CH2:18][CH:13]3[CH2:14][CH:15]([CH2:17][C:11]([NH2:19])([CH2:12]3)[CH2:10]1)[CH2:1... | CC(C)(C)OC(=O)NC12CC3CC(CC(C#Cc4cnccn4)(C3)C1)C2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | 25 | null | To a stirred solution of tert-butyl 3-(pyrazin-2-ylethynyl)-1-adamantylcarbamate (108 mg, 0.31 mol) in DCM (3 mL) was added TFA (0.5 mL). After stirring at room temperature for an hour, the reaction was concentrated under reduced pressure. The resulting residue was diluted with DCM (25 mL), washed with Sat. NaHCO3 and ... | NC12CC3CC(C1)CC(C#Cc1cnccn1)(C3)C2 | null | 0.1 | null |
727,987 | ord_dataset-eb4226b4f7644a01a737e7547b70014a | null | 2006-01-01T00:09:00 | true | CON(C)[C:4]([C@@H:6]1[CH2:10][CH2:9][CH2:8][C@H:7]1[C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]#[N:21])[CH:18]=2)[NH:13][CH:12]=1)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH:4]([C@@H:6]1[CH2:10][CH2:9][CH2:8][C@H:7]1[C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]#[N:21])[CH:18]=2)[NH:13][CH:12]=1)=[O:5... | CON(C)C(=O)[C@@H]1CCC[C@H]1c1c[nH]c2ccc(C#N)cc12 | 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 | -40 | 0.08 | Trans-2-(5-cyano-1H-indol-3-yl)-cyclopentanecarboxylic acid methoxy-methyl-amide (460 mg, 1.5 mMol) was dissolved in THF and cooled to −40° C. Lithium aluminum hydride (117 mg, 3.1 mMol) was added and the temperature was maintained between −40 and −30° C. for 1 h. The reaction was quenched with ethyl acetate (10 mL) an... | N#Cc1ccc2[nH]cc([C@@H]3CCC[C@H]3C=O)c2c1 | null | 70.5 | null |
52,178 | ord_dataset-8881493772e04c4b9495fc2114379967 | null | 1979-01-01T00:02:00 | true | [Br:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7](CC#N)=[CH:6][CH:5]=1.[C:13]([OH:16])(=[O:15])[CH3:14]>Br>[Br:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:14][C:13]([OH:16])=[O:15])=[CH:6][CH:5]=1 | N#CCc1ccc(CCBr)cc1 | CC(=O)O | null | Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | A solution of [4-(2-bromoethyl)phenyl]acetonitrile (56.0 g., 0.25 mole) in 48% hydrobromic acid (200 ml.) and acetic acid (600 ml.) is boiled under reflux for 4 hours. The solution is reduced to one-third volume by distillation at reduced pressure. The residue is diluted with 400 ml. of water to force out the oily prod... | O=C(O)Cc1ccc(CCBr)cc1 | null | null | null |
1,371,371 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | C(O[C:4](=[O:16])[CH2:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=1)=O)C.[CH2:17]1[CH:19]([C:20]([NH2:22])=[NH:21])[CH2:18]1.Cl.CC(C)([O-])C.[K+]>CO>[CH:19]1([C:20]2[N:22]=[C:4]([OH:16])[CH:5]=[C:6]([C:8]3[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=3)[N:21]=2)[CH2:17][CH2:18]1 | N=C(N)C1CC1 | CCOC(=O)CC(=O)c1ccc(Cl)c(Cl)c1 | null | CC(C)(C)[O-] | Cl | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 8 | To a solution consisting of 3-(3,4-dichlorophenyl)-3-oxo-propionic acid ethyl ester (252 mg, 0.967 mmol) and MeOH were added cyclopropylcarbamidine hydrochloride (140 mg, 1.16 mmol) and potassium tert-butoxide (266 mg, 2.37 mmol). The reaction mixture was stirred at rt overnight, then concentrated. Water and CH2Cl2 wer... | Oc1cc(-c2ccc(Cl)c(Cl)c2)nc(C2CC2)n1 | null | 48.9 | null |
1,359,387 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | [CH2:1]([O:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[C:11]([O:19][CH3:20])[N:12]2[CH2:15][CH2:16][CH2:17]Cl)=[C:8]([NH2:21])[N:7]=1)[CH2:2][CH2:3][CH3:4].CCN(C(C)C)C(C)C.[N:31]1([CH2:37][CH2:38][OH:39])[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1>C(#N)C>[NH2:21][C:8]1[N:7]=[C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])[N:14]=[C:13]2[C... | CCCCOc1nc(N)c2nc(OC)n(CCCCl)c2n1 | OCCN1CCNCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 70 | null | 2-(Butyloxy)-9-(3-chloropropyl)-8-(methyloxy)-9H-purin-6-amine (for example, as prepared for Intermediate 39) (80 mg, 0.255 mmol), DIPEA (0.134 mL, 0.765 mmol) and 2-(1-piperazinyl)ethanol (commercially available, for example, from Aldrich) (133 mg, 1.020 mmol) was heated in acetonitrile (2 mL) in a test-tube in a Radl... | CCCCOc1nc(N)c2nc(OC)n(CCCN3CCN(CCO)CC3)c2n1 | null | null | null |
1,124,390 | ord_dataset-285df12e34cd46e993e3c8ebc3a8962a | null | 2012-01-01T00:01:00 | true | [OH:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:15](Br)[CH:16]=[CH2:17].Cl>CN(C=O)C>[CH2:17]([S:8][C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=1)[CH:16]=[CH2:15] | Oc1ccc(S)cc1 | C=CCBr | null | Cl | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 0 | 0.25 | To a stirred solution of 4-hydroxythiophenol (1.6) (4.30 g, 34.1 mmol) in DMF (25 mL) were added K2CO3 (4.71 g, 34.1 mmol) and allyl bromide (3.09 mL, 34.1 mmol) at ice-water temperature, and the mixture was stirred for 15 minutes, prior to stirring overnight at room temperature. After the addition of 1 M aqueous HCl, ... | C=CCSc1ccc(O)cc1 | null | 101.3 | null |
862,092 | ord_dataset-b8b98725045d45bdbd73512048f4b47e | null | 2009-01-01T00:02:00 | true | [C:1]([C:3]1[S:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][C:4]=1[N+:12]([O-])=O)#[N:2].C(O)(=O)C>[Fe]>[NH2:12][C:4]1[CH:5]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[S:7][C:3]=1[C:1]#[N:2] | COC(=O)c1cc([N+](=O)[O-])c(C#N)s1 | null | null | [Fe] | 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 | A suspension of methyl 5-cyano-4-nitro-thiophene-2-carboxylate (0.17 mol, 36 g) and iron powder (0.51 mol, 28.5 g) in glacial acetic acid 68 mL (1.2 mol) was refluxed for 3 hours. The crude was concentrated under vacuum and neutralized with diluted ammonia. The aqueous layer was extracted with ethyl acetate (3×250 mL) ... | COC(=O)c1cc(N)c(C#N)s1 | null | 69.1 | null |
452,313 | ord_dataset-3bcdb559226a40d89406474c02d082d1 | null | 1999-01-01T00:12:00 | true | [OH:1][CH:2]([CH2:6][N:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)[CH2:3][O:4][NH2:5].[N+:13]([C:16]1[CH:17]=[C:18]([N:22]=[C:23]=[O:24])[CH:19]=[CH:20][CH:21]=1)([O-:15])=[O:14]>C(Cl)(Cl)Cl>[N+:13]([C:16]1[CH:17]=[C:18]([NH:22][C:23]([NH:5][O:4][CH2:3][CH:2]([OH:1])[CH2:6][N:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)... | NOCC(O)CN1CCCCC1 | O=C=Nc1cccc([N+](=O)[O-])c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | O-(2-hydroxy-3-piperidino-propyl)-hydroxylamine (1,74 g, 0,01 mol) was dissolved in 25 ml abs. chloroform and 1,64 g (0,01 mol) 3-nitrophenyl isocyanate in 20 ml abs. chloroform was added thereto while stirring. After 1 hour reaction the mixture was evaporated and purified by column chromatography. The oil thus obtaine... | O=C(NOCC(O)CN1CCCCC1)Nc1cccc([N+](=O)[O-])c1 | null | null | null |
745,028 | ord_dataset-4b705442211b4a3988e26d5f65098160 | null | 2006-01-01T00:12:00 | true | C[CH:2]([CH:6]1[C:10]2=[CH:11][C:12]3[C:13]([Br:19])=[CH:14][C:15]([F:18])=[CH:16][C:17]=3[N:9]2[CH2:8][CH2:7]1)[C:3]([O-:5])=[O:4].[Cl:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[C:23]([I:30])[CH:22]=1>>[Br:19][C:13]1[C:12]2[C:11]([C:25](=[O:26])[C:24]3[CH:28]=[CH:29][C:21]([Cl:20])=[CH:22][C:23]=3[I:30])=[C:1... | CC(C(=O)[O-])C1CCn2c1cc1c(Br)cc(F)cc12 | O=C(Cl)c1ccc(Cl)cc1I | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Starting from (+/−)-methyl(8-bromo-6-fluoro-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (example 7, Step 8) and 4-chloro-2-iodobenzoyl chloride, the title compound was synthesized following the procedures described in Step 1 of Example 61 and Step 10 of Example 7. | O=C(O)CC1CCn2c1c(C(=O)c1ccc(Cl)cc1I)c1c(Br)cc(F)cc12 | null | null | null |
1,229,495 | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | null | 2012-01-01T00:11:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]([CH3:14])[N:12]=[C:11]([C:15](=O)[CH3:16])[C:10]=2[OH:18])[CH:5]=[CH:6][C:7]=1[Cl:8].[N+:19]([C:22]1[CH:31]=[C:30]([C:32]([NH:34][NH2:35])=[O:33])[CH:29]=[CH:28][C:23]=1[C:24]([O:26][CH3:27])=[O:25])([O-:21])=[O:20].O.S(C1C=CC(C)=CC=1)(O)(=O)=O>>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13... | COC(=O)c1ccc(C(=O)NN)cc1[N+](=O)[O-] | CC(=O)c1nn(C)c(-c2ccc(Cl)c(Cl)c2)c1O | null | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | null | null | From 1-[5-(3,4-dichlorophenyl)-4-hydroxy-1-methyl-1H-pyrazol-3-yl]ethanone (0.70 mmol, 200 mg) synthesized in Synthetic Example 1, methyl 2-nitro-4-hydrazinocarbonylbenzoate (0.70 mmol, 167.8 mg) of Reference Synthetic Example 40 and tosylic acid monohydrate (36.2 mg, 0.21 mmol), 311.1 mg of the desired product was obt... | COC(=O)c1ccc(C(=O)NN=C(C)c2nn(C)c(-c3ccc(Cl)c(Cl)c3)c2O)cc1[N+](=O)[O-] | null | 87.8 | null |
1,096,517 | ord_dataset-af85e6f81c2d49f08086afd6d9e6959c | null | 2011-01-01T00:10:00 | true | [Cl-].[Li+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.C1CCN2C(=NCCC2)CC1.[F:28][C:29]([F:35])([F:34])[CH2:30][CH2:31][CH:32]=O>CC#N>[F:28][C:29]([F:35])([F:34])[CH2:30][CH2:31]/[CH:32]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13] | O=CCCC(F)(F)F | CCOC(=O)CP(=O)(OCC)OCC | null | [Cl-] | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | C1CCC2=NCCCN2CC1 | null | null | null | null | null | null | null | null | null | 0 | 8 | To a suspension of lithium chloride (0.504 g, 11.9 mmol) in MeCN (20 mL) were added ethyl 2-(diethoxyphosphoryl)acetate (available from Aldrich) (1.91 mL, 9.52 mmol) and DBU (1.42 mL, 9.52 mmol) at room temperature. The mixture was cooled to 0° C., and 4,4,4-trifluorobutanal (available from Matrix Scientific) (1.00 g, ... | CCOC(=O)/C=C/CCC(F)(F)F | null | 72.6 | null |
799,047 | ord_dataset-56a22bc0c3b14f87b9aa3f2fc6488ee7 | null | 2007-01-01T00:12:00 | true | [NH2:1][CH:2]([CH2:6][S:7][CH2:8][CH2:9]O)[C:3]([OH:5])=[O:4].[ClH:11]>>[ClH:11].[NH2:1][CH:2]([CH2:6][S:7][CH2:8][CH2:9][Cl:11])[C:3]([OH:5])=[O:4] | NC(CSCCO)C(=O)O | 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 | 7 | 33.9 g of 2-amino-3-(2-hydroxy-ethylsulfanyl)-propionic acid was dissolved in 800 mL of concentrated hydrogen chloride and the solution was stirred for 7 h to obtain a buff solid. The solid was recrystallized in isopropanol to obtain a white powder (34.2 g). Yield 75.4%, mp 185-186° C. | NC(CSCCCl)C(=O)O | null | 75.4 | null |
608,918 | ord_dataset-73916d628db147c89020b3baac642d48 | null | 2003-01-01T00:09:00 | true | N12CCCN=C1CCCCC2.[Cl:12][C:13]1[CH:14]=[C:15]([NH:20][C:21]2[C:30]3[C:25](=[CH:26][C:27]([O:37][CH2:38][CH2:39]Br)=[C:28]([O:31][CH:32]4[CH2:36][CH2:35][CH2:34][CH2:33]4)[CH:29]=3)[N:24]=[CH:23][N:22]=2)[CH:16]=[CH:17][C:18]=1[F:19].[C:41]([O:45][C:46]([N:48]1[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]1)=[O:47])([CH3:44])(... | CC(C)(C)OC(=O)N1CCNCC1 | Fc1ccc(Nc2ncnc3cc(OCCBr)c(OC4CCCC4)cc23)cc1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | C1CCC2=NCCCN2CC1 | null | null | null | null | null | null | null | null | null | 60 | 2 | 340 mg of 1,8-diazabicyclo[5.4.0]undec-7-ene are added at ambient temperature to 940 mg of 4-[(3-chloro-4-fluorophenyl)amino]-6-cyclopentyloxy-7-(2-bromoethoxy)-quinazoline and 1.00 g of N-(tert.butyloxycarbonyl)-piperazine in 30 ml of acetonitrile. The reaction mixture is heated to 60° C. for five hours. Then a furthe... | CC(C)(C)OC(=O)N1CCN(CCOc2cc3ncnc(Nc4ccc(F)c(Cl)c4)c3cc2OC2CCCC2)CC1 | null | null | null |
586,946 | ord_dataset-cb5dd7a8b94e4f19a9148a1904b0dcb6 | null | 2003-01-01T00:03:00 | true | O.[F:2][C:3]1[C:23]([N:24]2[C:29](=[O:30])[CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[N:26]([CH3:35])[C:25]2=[O:36])=[CH:22][C:6]([O:7][C:8]2[C:9]([O:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[N:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=2)=[C:5]([N+:37]([O-])=O)[CH:4]=1>C(O)(=O)C.[Fe]>[NH2:37][C:5]1[CH:4]=[C:3]([F:2])[... | COC(=O)COc1nc(OC)ccc1Oc1cc(-n2c(=O)cc(C(F)(F)F)n(C)c2=O)c(F)cc1[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 | 35 | 2 | To a mixture of an iron powder, acetic acid and water is added a solution of 3-{4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]-2-nitrophenoxy}-6-methoxy-2-(methoxycarbonyl)methoxypyridine in acetic acid dropwise while maintaining the temperature of the reaction solution at 35° C. o... | COC(=O)COc1nc(OC)ccc1Oc1cc(-n2c(=O)cc(C(F)(F)F)n(C)c2=O)c(F)cc1N | null | null | null |
1,135,214 | ord_dataset-aaeaab5f3720492494c1cbbdd0ed2820 | null | 2012-01-01T00:02:00 | true | [CH3:1][C:2]1[N:3]=[C:4]2[S:19][CH:18]=[CH:17][N:5]2[C:6](=[O:16])[C:7]=1[C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1.[CH2:20]([O:22][CH2:23][CH2:24][O:25][C:26]1[C:33]([O:34][CH3:35])=[CH:32][CH:31]=[CH:30][C:27]=1[CH:28]=O)[CH3:21].[O-]CC.[Na+]>>[CH2:20]([O:22][CH2:23][CH2:24][O:25][C:26]1[C:33]([O:34][... | CCOCCOc1c(C=O)cccc1OC | Cc1nc2sccn2c(=O)c1-c1ccc(C#N)cc1 | null | CC[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared by condensation of Intermediate 4 (335 mg, 1.252 mmol) with 2-(2-ethoxyethoxy)-3-methoxy-benzaldehyde (339 mg, 1.753 mmol) in presence of sodium ethoxide (170 mg, 2.506 mmol) according to the procedure described in Example 9 to yield 231 mg of the desired product as a light yellow solid;... | CCOCCOc1c(/C=C/c2nc3sccn3c(=O)c2-c2ccc(C#N)cc2)cccc1OC | null | 39 | null |
786,565 | ord_dataset-4ad5db8537994579bef51f16dd8bf0bd | null | 2007-01-01T00:08:00 | true | Br[CH2:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:9]([C:13]([F:16])([F:15])[F:14])[O:10]2)=[CH:5][C:4]=1[Cl:22].[CH:23]([NH:26][CH3:27])([CH3:25])[CH3:24].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:22][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:3]=1[CH2:2][N:26]([CH:23]([CH3:25])[CH3:24])[... | CNC(C)C | CCOC(=O)C1=Cc2cc(Cl)c(CBr)cc2OC1C(F)(F)F | 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 | null | 3 | The ethyl 7-(bromomethyl)-6-chloro-2-(trifluoromethyl)-2H-chromene-3-carboxylate from Example 16, Step 3 (01597/1 PR) (1.0 g, 2.5 mmol) was dissolved in DMF (5 mL). The solution was cooled at ice bath under nitrogen and the isopropyl(methyl)-amine (0.26 mL, 2.5 mmole) was added into the solution followed by addition of... | CCOC(=O)C1=Cc2cc(Cl)c(CN(C)C(C)C)cc2OC1C(F)(F)F | null | null | null |
163,052 | ord_dataset-f5dc3e448c204058b116bf1970695bef | null | 1987-01-01T00:09:00 | true | [Cl:1][C:2]1[CH:6]([N:7]2[C:11](=[O:12])[C:10]3=[CH:13][CH:14]=[CH:15][CH:16]=[C:9]3[C:8]2=[O:17])[CH2:5][O:4][N:3]=1.[CH3:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH2:24])=[CH:21][CH:20]=1>O1CCCC1>[Cl:1][C:2]1[CH:6]([NH:7][C:11](=[O:12])[C:10]2[C:9](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]([NH:24][CH2:23][C:22]2[CH:25]=... | Cc1ccc(CN)cc1 | O=C1c2ccccc2C(=O)N1C1CON=C1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 4 | 3-Chloro-4-phthalimido-4,5-dihydroisoxazole (4 g, 16 mmol) was dissolved in 50 ml of dried tetrahydrofuran. 4-Methylbenzylamine (2.18 g, 18 mmol) was added at room temperature and the reaction solution was stirred at room temperature for 4 hours. The reaction mixture was concentrated in vacuo, and the residue recrystal... | Cc1ccc(CNC(=O)c2ccccc2C(=O)NC2CON=C2Cl)cc1 | null | null | null |
278,426 | ord_dataset-ad17798fcea64e26ba91604fca520090 | null | 1993-01-01T00:10:00 | true | [C:1]([NH:4][C:5]1[S:6][C:7](Cl)=[C:8]([CH2:10][OH:11])[N:9]=1)(=[O:3])[CH3:2].[SH:13][C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:1]([NH:4][C:5]1[S:6][C:7]([S:13][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[C:8]([CH2:10][OH:11])[N:9]=1)(=[O:3])[CH3:2] | Sc1ccncc1 | CC(=O)Nc1nc(CO)c(Cl)s1 | 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 | 110 | null | A mixture of 2-acetylamino-5-chloro-4-hydroxymethylthiazole (1 g), 4-mercaptopyridine (0.6 g) and potassium carbonate (1 g) in N,N-dimethylformamide (20 ml) was heated at 110° C. for 8 hours with stirring. The reaction mixture was poured into ice water and filtered by suction. The filtrate was extracted with a mixture ... | CC(=O)Nc1nc(CO)c(Sc2ccncc2)s1 | null | 66.1 | null |
437,232 | ord_dataset-a1e9aa99368e4e5da8b1786b1c05521d | null | 1999-01-01T00:08:00 | true | [C:1](OC)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].C([Li])CCC.[C:16]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:23])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>CCCCCC.O1CCCC1>[CH2:17]([C:16]1([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[O:23][C:1](=[O:6])[CH:2]=[C:3]([OH:4])[CH2:5]1)[CH2:18][CH2:1... | CCCCCCC(=O)c1ccccc1 | COC(=O)CC(C)=O | null | [H-] | [Li]CCCC | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCCCCC | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared as described in General Method 1 using 25 mmol of methyl acetoacetate, 27.5 mmol of NaH 60% dispersion in oil, 26.25 mmol of 1.6 M n-butyl lithium in hexane, 25 mmol of heptanophenone and 70 mL of tetrahydrofuran. Upon concentrating the reaction, a solid precipitated out which was tritur... | CCCCCCC1(c2ccccc2)CC(O)=CC(=O)O1 | null | null | null |
753,535 | ord_dataset-844a22e1fcab44a5b59c5e2922b2855a | null | 2007-01-01T00:01:00 | true | [Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][C:6]1[C:15]2[C:9]([CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:8][CH:7]=1.[Br:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=1)[C:20](Cl)=[O:21].Cl>C(Cl)Cl>[Br:16][C:17]1[CH:18]=[C:19]([C:20]([C:8]2[C:9]3[C:15]([CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:6]([CH3:5])[CH:7]=2)=[O:21])[CH... | O=C(Cl)c1cccc(Br)c1 | Cc1ccc2cccccc1-2 | null | Cl | [Al+3] | [Cl-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | 0.25 | Aluminum chloride (1.87 g) was added to a solution of 1-methylazulene (2 g) in methylene chloride (20 ml) at 0° C. and the mixture was stirred for 15 minutes. Then, a solution of 3-bromobenzoyl chloride (1.86 ml) in methylene chloride (5 ml) was added dropwise to the reaction mixture at 0° C. and the mixture was stirre... | Cc1cc(C(=O)c2cccc(Br)c2)c2cccccc1-2 | null | null | null |
1,763,340 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:26]#[N:27])=[C:6]([C:8]2[C:13]([O:14][CH2:15][C:16]([F:19])([F:18])[F:17])=[CH:12][N:11]([CH:20]([CH3:24])[C:21]([OH:23])=O)[C:10](=[O:25])[CH:9]=2)[CH:7]=1.[NH2:28][C:29]1[CH:41]=[CH:40][C:32]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[CH:31][CH:30]=1>>[Cl:1][C:2]1[CH:3... | CC(C)(C)OC(=O)c1ccc(N)cc1 | CC(C(=O)O)n1cc(OCC(F)(F)F)c(-c2cc(Cl)ccc2C#N)cc1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 214 mg (purity 73%, 0.39 mmol) of 2-[4-(5-chloro-2-cyanophenyl)-2-oxo-5-(2,2,2-trifluoroethoxy)pyridin-1(2H)-yl]propanoic acid (racemate) and 83 mg (0.43 mmol, 1.1 eq.) of tert-butyl 4-aminobenzoate were reacted according to General Method 5A. Yield: 113 mg (purity 70%, 35% of theory) | CC(C(=O)Nc1ccc(C(=O)OC(C)(C)C)cc1)n1cc(OCC(F)(F)F)c(-c2cc(Cl)ccc2C#N)cc1=O | null | null | null |
1,211,591 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | O[CH:2]1[N:6]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[N:5]([CH2:17][C:18]#[CH:19])[C:4]([CH3:21])([CH3:20])[CH2:3]1.C(O)=[O:23]>>[CH3:20][C:4]1([CH3:21])[N:5]2[N:6]([C:7]([O:9][CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:8])[CH:2]([CH2:19][C:18](=[O:23])[CH2:17]2)[CH2:3]1 | O=CO | C#CCN1N(C(=O)OCc2ccccc2)C(O)CC1(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 stirred solution of 105 (2.5 g, 8.6 mmol) in formic acid (10 mL) was heated at 100° C. for 5 h. After complete consumption of 105 (as monitored by TLC), formic acid was evaporated under reduced pressure. The residue was dissolved in EtOAc (100 mL) and washed with saturated with NaHCO3 solution (2×50 mL), water (50 mL... | CC1(C)CC2CC(=O)CN1N2C(=O)OCc1ccccc1 | null | 18 | null |
801,448 | ord_dataset-56a22bc0c3b14f87b9aa3f2fc6488ee7 | null | 2007-01-01T00:12:00 | true | [CH3:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([CH3:11])[N:5]=[CH:4][N:3]=1.N[CH2:13][C:14]1C=C(C=CC=1)CN(CC1NC2C=CC=CC=2N=1)C1C2N=CC=CC=2CCC1.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.CCN=C=NCCCN(C)C>CN(C=O)C>[CH2:13]([O:9][C:8]([C:7]1[C:2]([CH3:1])=[N:3][CH:4]=[N:5][C:6]=1[CH3:11])=[O:10])[CH3:14] | Cc1ncnc(C)c1C(=O)O | NCc1cccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)c1 | null | CCN=C=NCCCN(C)C | On1nnc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CN1CCOCC1 | null | null | null | null | null | null | null | null | null | 25 | 8 | Using General Procedure F: A solution of 4,6-dimethyl-pyrimidine-5-carboxylic acid from above (prepared as described in patent application PCT/US00/11632) (42 mg, 0.28 mmol), (3-aminomethyl-benzyl)-(1H-benzoimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (100 mg, 0.25 mmol), HOBT (38 mg, 0.28 mmol) and 4-... | CCOC(=O)c1c(C)ncnc1C | null | null | null |
1,186,179 | ord_dataset-9cd817a75dfc4fe7ad19d4232772d5ff | null | 2012-01-01T00:07:00 | true | [OH:1][NH:2][C:3](=[NH:22])[C:4]1[C:14]2[CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][CH2:9][C:8]=2[CH:7]=[CH:6][CH:5]=1.[H-].[Na+].[C:25]([C:27]1[CH:28]=[C:29]([CH:34]=[CH:35][C:36]=1[O:37][CH:38]([CH3:40])[CH3:39])[C:30](OC)=O)#[N:26]>C1COCC1>[C:25]([C:27]1[CH:28]=[C:29]([C:3... | COC(=O)c1ccc(OC(C)C)c(C#N)c1 | CC(C)(C)OC(=O)N1CCc2cccc(C(=N)NO)c2CC1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | 1,1-Dimethylethyl 6-[(hydroxyamino)(imino)methyl]-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (Preparation 15) (360 mg, 1.179 mmol) was dissolved in THF (50 ml) and stirred with sodium hydride (60% dispersion in mineral oil, 51.9 mg, 1.297 mmol) under argon at room temperature for 30 minutes. Then methyl 3-cyano-... | CC(C)Oc1ccc(-c2nc(-c3cccc4c3CCN(C(=O)OC(C)(C)C)CC4)no2)cc1C#N | null | 85.8 | null |
1,297,138 | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | null | 2013-01-01T00:05:00 | true | [Br:1][C:2]1[CH:11]=[CH:10]C(C(OC)=O)=[CH:4][C:3]=1[CH3:12].[C:13]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:15])[CH3:14].CC(C)([O-])C.[K+]>C1COCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:14]([C:13]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:4][C:3]=1[CH3:12] | COC(=O)c1ccc(Br)c(C)c1 | CC(=O)OC(C)(C)C | null | CC(C)(C)[O-] | [K+] | 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 | null | 0.17 | To a mixture of methyl 4-bromo-3-methylbenzoate (4.85 g) and tert-butyl acetate (3 mL) was added 1M potassium tert-butoxide in THF (0.3 mL). The mixture was stirred under vacuum for 10 minutes and treated with another equivalent of tert-butyl acetate and 1 mol % of (1,1′-bis(diphenylphosphino)ferrocene)dichloropalladiu... | Cc1cc(C(=O)OC(C)(C)C)ccc1Br | null | null | null |
742,162 | ord_dataset-437aa6654d5044ddaef3346dc4c6e08a | null | 2006-01-01T00:11:00 | true | [NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]3[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:11]=3[N:12]=2)[CH:5]=[CH:6][CH:7]=1.[CH:18]1[C:23]([C:24]([OH:26])=[O:25])=[CH:22][C:21]2[C:27]([O:29][C:30](=O)[C:20]=2[CH:19]=1)=[O:28]>>[CH3:17][C:15]1[CH:14]=[CH:13][C:11]2[N:12]=[C:8]([C:4]3[CH:3]=[C:2]([N:1]4[C:27](=[O:28])[C:21... | Cc1ccc2nc(-c3cccc(N)c3)oc2c1 | O=C(O)c1ccc2c(c1)C(=O)OC2=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared by the method of Example 1b), from 2-(3-aminophenyl)-6-methylbenzoxazole (32 mg, 0.14 mmol) and 1,2,4-benzenetricarboxylic anhydride (30 mg, 0.16 mmol) the title compound was obtained, 42 mg (72%). 1H NMR (DMSO) δ 8.45(dd, 1H), 8.34(bd, 2H), 8.25(dt, 1H), 8.13(d, 1H), 7.75(m, 3H), 7.63(s, 1H), 7.26(d, 1H), 2.5... | Cc1ccc2nc(-c3cccc(N4C(=O)c5ccc(C(=O)O)cc5C4=O)c3)oc2c1 | null | null | null |
527,739 | ord_dataset-f027aa93238e424fbbf9bad1c7699adc | null | 2001-01-01T00:12:00 | true | O[CH:2]1[C:10]2[C:5](=[C:6]([O:17][CH3:18])[C:7]([O:15][CH3:16])=[C:8]([O:13][CH3:14])[C:9]=2[O:11][CH3:12])[CH2:4][CH:3]1[CH2:19][CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:25]=1.Cl>[C].[Pd].CO>[CH3:18][O:17][C:6]1[C:7]([O:15][CH3:16])=[C:8]([O:13][CH3:14])[C:9]... | COC(=O)c1ccc(OCCCCC2Cc3c(OC)c(OC)c(OC)c(OC)c3C2O)cc1 | null | null | [Pd] | Cl | 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 | 25 | 4 | A methanol (30 ml) suspension of methyl 4-[4-(1-hydroxy-4,5,6,7-tetramethoxyindan-2-yl)butoxy]benzoate (1.50 g, 3.26 mmols), concentrated hydrochloric acid (0.0652 ml, 0.652 mmols) and 10% palladium-carbon (300 mg) was stirred under a hydrogen stream at room temperature for 4 hours. The palladium-carbon was removed by ... | COC(=O)c1ccc(OCCCCC2Cc3c(c(OC)c(OC)c(OC)c3OC)C2)cc1 | null | 86.3 | null |
314,807 | ord_dataset-bd998d3fe946475e835418aaf647c00d | null | 1995-01-01T00:08:00 | true | [NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9](I)[CH:8]=2)[C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=2[N:3]=1.[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1B(O)O>>[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:19]3[S:18][CH:22]=[CH:21][CH:20]=3)[CH:8]=2)[C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=2[N:3]=1 | Nc1nc2ccccc2n1-c1cccc(I)c1 | OB(O)c1cccs1 | null | null | null | null | null | null | null | 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-Amino-1-[3-(2-thienyl)phenyl]benzimidazole was prepared from 1-(2-amino-1-benzimidazolyl)-3-iodobenzene and 2-thienylboronic acid by method B. mp 142°-144° C. | Nc1nc2ccccc2n1-c1cccc(-c2cccs2)c1 | null | null | null |
1,417,453 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | [CH:1]1([NH:4][C:5](=[O:31])[CH2:6][N:7]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([CH2:17][C:18]4[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=4)[CH:15]=3)[C:10]([OH:25])=[C:9]([C:26]([NH:28][CH3:29])=[O:27])[C:8]2=[O:30])[CH2:3][CH2:2]1.[OH-].[Na+:33]>>[CH:1]1([NH:4][C:5](=[O:31])[CH2:6][N:7]2[C:16]3[C:11](=[N:12][CH:13]=[C... | CNC(=O)c1c(O)c2ncc(Cc3ccc(F)cc3)cc2n(CC(=O)NC2CC2)c1=O | null | null | [Na+] | [OH-] | null | null | 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 | 4 | This compound was prepared by treating a mixture of the product from Example 473 with 1.5 equivalents of 1N NaOH solution. The mixture was stirred 4 h at rt and filtered to afford the product as a white solid: 1H NMR (d6-DMSO) δ 10.15 (1H, br), 8.25 (1H, s), 7.69 (1H, br), 7.27 (3H, m), 7.08 (2H, t, J=9 Hz), 4.70 (2H, ... | CNC(=O)c1c([O-])c2ncc(Cc3ccc(F)cc3)cc2n(CC(=O)NC2CC2)c1=O | null | null | null |
401,552 | ord_dataset-7fed188163cf4ccca934ec71504c7f8a | null | 1998-01-01T00:05:00 | true | [C:1]([N:5]1[C:10](=[O:11])[C:9]([CH:12]([OH:14])[CH3:13])=[C:8]([N:15]([CH3:17])[CH3:16])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[C:12]([C:9]1[C:10](=[O:11])[N:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[N:6]=[CH:7][C:8]=1[N:15]([CH3:16])[CH3:17])(=[O:14])[CH3:13] | CC(O)c1c(N(C)C)cnn(C(C)(C)C)c1=O | null | null | [Mn+4] | [O-2] | 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 | 80 | 24 | In toluene was dissolved 2-t-butyl-5-dimethylamino-4-(1-hydroxy)ethyl-3(2H)-pyridazinone (3.4 g) followed by addition of active manganese dioxide (17.0 g), and the mixture was stirred at 80° C. for 24 hours. The oxidizing agent was filtered off and the filtrate was concentrated. The residue was washed with n-hexane and... | CC(=O)c1c(N(C)C)cnn(C(C)(C)C)c1=O | null | null | null |
604,722 | ord_dataset-273fda773e864aaf9b71a30a2d9f2162 | null | 2003-01-01T00:08:00 | true | [CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]([C:7]([NH:9][C:10]2[C:11]([NH:16][C:17]([CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)=[O:18])=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:8])=[CH:5][CH:4]=1.[N+:27]([C:30]1[CH:37]=[CH:36][C:33]([CH:34]=O)=[CH:32][CH:31]=1)([O-:29])=[O:28]>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([N... | O=Cc1ccc([N+](=O)[O-])cc1 | COc1ccc(C(=O)Nc2ccccc2NC(=O)C2CCNCC2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Using the general procedure described in Example 3, N1-(4-methoxybenzoyl)-N2-(piperidin-4-ylcarbonyl)-1,2-benzenediamine (0.14 mmol) was reacted with 4-nitrobenzaldehyde to provide 36 mg of the title product as the free base. Treatment with hydrochloric acid and concentration in vacuo yielded the salt of the title comp... | COc1ccc(C(=O)Nc2ccccc2NC(=O)C2CCN(Cc3ccc([N+](=O)[O-])cc3)CC2)cc1 | null | null | null |
993,279 | ord_dataset-b6d8835b0c934476a36e6149e7597487 | null | 2010-01-01T00:09:00 | true | [OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[C:7](=[O:13])[CH2:6][CH2:5]2.Cl[CH2:15][CH2:16][CH2:17][O:18][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][O:20]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH3:12][O:11][C:10]1[CH:9]=[C:8]2[C:4]([CH2:5][CH2:6][C:7]2=[O:13])=[CH:3][C:2]=1[O:1][CH2:15][CH2:16... | COc1cc2c(cc1O)CCC2=O | ClCCCOC1CCCCO1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | A mixture of 5-Hydroxy-6-methoxy-indan-1-one (Intermediate H, 2.98 g, 0.017 mole), 2-(3-chloro-propoxy)-tetrahydro-pyran (Compound 18a) (6.0 g, 0.034 mole), and potassium carbonate (10.0 g, 0.0725 mole) were stirred in 50 mL of DMF at 80° C. overnight under Argon. The reaction mixture was then diluted with 200 mL of et... | COc1cc2c(cc1OCCCOC1CCCCO1)CCC2=O | null | null | null |
675,006 | ord_dataset-632f0d9054ce41aba87d4970966c34a6 | null | 2005-01-01T00:06:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH3:21])[CH:18]=3)[CH2:13][CH2:12][N:11]=2)=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH3:21])[CH:18]=3)[CH2:13][CH2:12][NH:11]2)=[CH:6][CH:... | COc1ccc2c(c1)C(CCc1ccc(F)cc1)=NCC2 | null | null | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 1-(2-p-fluorophenylethyl)-7-methoxy-3,4-dihydroisoquinoline (1.04 g, 3.67 mmol) in methanol (7 ml) was treated with sodium borohydride (0.56 g, 14.7 mmol) and heated at reflux for one hour. The mixture was cooled and evaporated. The residue was mixed with 1N sodium hydroxide and ethyl acetate and extracte... | COc1ccc2c(c1)C(CCc1ccc(F)cc1)NCC2 | null | null | null |
708,658 | ord_dataset-c8069773c1a148aca8ab417108daacc5 | null | 2006-01-01T00:05:00 | true | [Li+].[Cl-].[CH3:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][C:11](OS(C(F)(F)F)(=O)=O)=[CH:12]2)=[CH:7][CH:6]=1.[CH2:23]([Sn](CCCC)(CCCC)C=C)[CH2:24]CC>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>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]2[C:13](=[CH:12][C:11]([CH:23]=[CH... | C=C[Sn](CCCC)(CCCC)CCCC | COc1ccc2ccc(OS(=O)(=O)C(F)(F)F)cc2c1 | null | Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1 | [Cl-] | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 90 | 4 | To a mixture of (Ph3P)2PdCl2 (1.752 g), LiCl (6.36 g), and trifluoromethanesulfonic acid 7-methoxy-naphthalen-2-yl ester (15.3 g) was added dropwise tributyl(vinyl)tin (19.02 g). The resulting mixture was stirred over 4 h at 90° C. The reaction was quenched with water and extracted with CH2Cl2. The organic layer was wa... | C=Cc1ccc2ccc(OC)cc2c1 | null | 97.8 | null |
1,318,719 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | [F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:3]=1[C:4](Cl)=[O:5].C(N(CC)CC)C.[NH2:22][C:23]1[CH:24]=[CH:25][C:26]([CH3:32])=[C:27]([CH:31]=1)[C:28]([OH:30])=[O:29]>C(Cl)Cl>[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:3]=1[C:4]([NH:22][C:23]1[CH:24]=[CH:25][C:26]([CH3:32... | O=C(Cl)c1cc(C(F)(F)F)ccc1F | Cc1ccc(N)cc1C(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 25 | 0.17 | To a 100 mL round-bottomed flask containing 2-fluoro-5-(trifluoromethyl)benzoyl chloride (0.44 ml, 2.9 mmol) in CH2Cl2 (30 mL) was added triethylamine (0.48 ml, 3.4 mmol). After 10 min, 5-amino-2-methylbenzoic acid (0.400 g, 2.6 mmol) was added. The solution was stirred at rt overnight. After cooling, the crude reactio... | Cc1ccc(NC(=O)c2cc(C(F)(F)F)ccc2F)cc1C(=O)O | null | null | null |
763,890 | ord_dataset-7a8649d55889427e85b208ae89475895 | null | 2007-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[C:9]([OH:11])=O)=[CH:4][CH:3]=1.[NH2:19][CH2:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][CH:26]([C:29]2[N:34]=[C:33]([NH:35][C:36](=[O:40])[CH:37]([CH3:39])[CH3:38])[CH:32]=[CH:31][CH:30]=2)[CH2:25][CH2:24]1>>[Cl:18][C:15]1[CH:... | O=C(O)C(c1ccc(Cl)cc1)c1ccc(Cl)cc1 | CC(C)C(=O)Nc1cccc(C2CCN(CCCN)CC2)n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Example 50 was prepared from bis(4-chlorophenyl)acetic acid and N-{6-[1-(3-aminopropyl)-4-piperidinyl]-2-pyridinyl}-2-methylpropanamide according to the procedures described in Scheme 10: 1H NMR (400 MHz, CDCl3) δ 8.06 (d, 1H, J=8.0 Hz), 7.96 (br s, 1H), 7.77 (s, 1H), 7.64 (t, 1H, J=8.4 Hz), 7.31–7.26 (m, 8H), 6.88 (dd... | CC(C)C(=O)Nc1cccc(C2CCN(CCCNC(=O)C(c3ccc(Cl)cc3)c3ccc(Cl)cc3)CC2)n1 | null | null | null |
1,196,940 | ord_dataset-4e81c470cc3b429faf5e1caa50f70a98 | null | 2012-01-01T00:08:00 | true | O=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=2)[CH2:5][CH:4]([C:17](O)=[O:18])[CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C.C1COCC1>[F:15][C:13]([F:14])([F:16])[C:9]1[CH:8]=[C:7]([N:6]2[CH2:2][CH2:3][CH:4]([CH2:17][OH:18])[CH2:5]2)[CH:12]=[CH:11][CH:10]=1 | O=C(O)C1CC(=O)N(c2cccc(C(F)(F)F)c2)C1 | null | null | [Al+3] | [H-] | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCOCC | null | null | null | null | null | null | null | null | null | 25 | 20 | 5-Oxo-1-(3-trifluoromethyl-phenyl)-pyrrolidine-3-carboxylic acid (0.35 g, 1.28 mmol) in diethyl ether (5 ml) was added to a solution of lithium aluminium hydride (0.097 g, 2.56 mmol) in THF (5 ml) at temperature 0° C. over a period of 10 min. The mixture was refluxed for 2 hours and then stirred at room temperature for... | OCC1CCN(c2cccc(C(F)(F)F)c2)C1 | null | null | null |
943,440 | ord_dataset-ed680843f6d14f5c9901869b2a06b4a4 | null | 2010-01-01T00:03:00 | true | [CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[C:18]1[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][C:19]=1[N+:25]([O-:27])=[O:26].C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:18]2[CH:23]=[C:22]([CH3:24])[CH:21]=[... | O=C(OCc1ccccc1)N1CCNCC1 | Cc1ccc([N+](=O)[O-])c(F)c1 | null | O=C([O-])[O-] | [K+] | 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 | 25 | null | Piperazine-1-carboxylic acid benzyl ester (8.00 g; 36.3 mmol), 2-fluoro-4-methyl-1-nitro-benzene (4.70 g; 30.3 mmol) and potassium carbonate (8.5 g; 61.5 mmol) were stirred 3 hours in 50 mL DMSO at 80° C. The reaction mixture was cooled to room temperature and 250 mL Water was added. The mixture was extracted with diet... | Cc1ccc([N+](=O)[O-])c(N2CCN(C(=O)OCc3ccccc3)CC2)c1 | null | 97.4 | null |
1,573,677 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | [CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]1[C:17]([C:48]([NH:50][CH2:51][CH:52]2[CH2:56][O:55]C(C)(C)[O:53]2)=[O:49])=[N:18][C:19]([NH:33][CH2:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][O:40][CH2:41][CH2:42][O:43][CH2:44][CH2:45][O:46][CH3:47])=[C:20]([C:... | COCCOCCOCCOCCCNc1nc(C(=O)NCC2COC(C)(C)O2)c(NCCCOCCOCCOCCOC)nc1C(=O)NCC1COC(C)(C)O1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 5 | To a reddish solution of the above dicetonide 14 (1.00 mmol) in THF (25 mL), was added 1.0 N HCl (5 mL) and stirred for 5 h in an atmosphere of argon. Most of the THF was removed from the reaction mixture, neutralized by 1.0 N NaOH, and concentrated in vacuo. The crude product (2.40 g) was subjected to preparative RP-H... | COCCOCCOCCOCCCNc1nc(C(=O)NCC(O)CO)c(NCCCOCCOCCOCCOC)nc1C(=O)NCC(O)CO | null | 73.6 | null |
1,250,671 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | Cl[C:2]1[C:11]([C:12]#[N:13])=[C:10]2[C:5]([CH2:6][CH:7]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=3)[C:8]3[CH:17]=[CH:16][CH:15]=[CH:14][C:9]=32)=[CH:4][N:3]=1.[CH3:26][N:27]1[CH2:31][CH2:30][CH2:29][CH:28]1[CH2:32][CH2:33][NH2:34]>CN(C)C=O>[Cl:25][C:20]1[CH:19]=[C:18]([CH:7]2[CH2:6][C:5]3[C:10](=[C... | CN1CCCC1CCN | N#Cc1c(Cl)ncc2c1-c1ccccc1C(c1ccc(Cl)c(Cl)c1)C2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 2-chloro-6-(3,4-dichlorophenyl)-5,6-dihydrobenzo[f]isoquinoline-1-carbonitrile (156 mg, 0.405 mmol) in N,N-dimethylformamide (3.5 ml) and 2-(1-methylpyrrolidin-2-yl)ethanamine (250 ul) was heated under microwave conditions at 20° C. for 40 minutes. The mixture was partitioned between ethyl acetate (50 ml)... | CN1CCCC1CCNc1ncc2c(c1C#N)-c1ccccc1C(c1ccc(Cl)c(Cl)c1)C2 | null | 50 | null |
421,061 | ord_dataset-94e21e9990034c729ea727e7d2ab0eb0 | null | 1998-01-01T00:12:00 | true | C(Cl)(Cl)Cl.[C:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)(=[O:7])[CH3:6].C1C=C[NH+]=CC=1.[Br:20][Br-]Br>C1COCC1>[Br:20][CH2:6][C:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)=[O:7] | CC(=O)c1ccccn1 | null | null | c1cc[nH+]cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 24 | To a 500 mL round bottomed flask with a stirring bar and an argon inlet is added CHCl3 (200 mL), THF (100 mL), 2-acetyl pyridine (8.57 mL, 76.46 mmol), and pyridinium bromide perbromide (26.85 g, 84.11 mmol). This solution is stirred at ambient temperature for 24 hours. The reaction mixture is washed with aqueous HCl, ... | O=C(CBr)c1ccccn1 | null | null | null |
1,627,978 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [NH2:1][CH:2]1[CH:7]([O:8]CC2C=CC=CC=2)[CH:6]([O:16]CC2C=CC=CC=2)[CH:5]([CH2:24][O:25]CC2C=CC=CC=2)[CH2:4][CH:3]1[OH:33]>CO.C(O)(=O)C.[Pd]>[NH2:1][CH:2]1[CH:3]([OH:33])[CH2:4][CH:5]([CH2:24][OH:25])[CH:6]([OH:16])[CH:7]1[OH:8] | NC1C(O)CC(COCc2ccccc2)C(OCc2ccccc2)C1OCc1ccccc1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | CC(=O)O | null | null | null | null | null | null | null | null | null | null | 8 | To a solution of Intermediate B (86.5 mg, 0.194 mmol) in MeOH (3 mL) and acetic acid (1 mL) was added Pd/C (10%, 102 mg, 0.097 mmol). The mixture was hydrogenated at 50 psi and at room temperature for 8 h. Catalyst was removed by filtration and solvents were evaporated under reduced pressure to give the product rac-(1R... | NC1C(O)CC(CO)C(O)C1O | null | null | null |
1,064,335 | ord_dataset-ffbef48837674f39816de887b5dc8bae | null | 2011-01-01T00:06:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Cl[S:15]([OH:18])(=[O:17])=[O:16]>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:13]([S:15]([OH:18])(=[O:17])=[O:16])=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1 | O=S(=O)(O)Cl | Fc1ccc(-c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | 4 | 4′-Fluorobiphenyl (5 g) was dissolved in chloroform (100 mL) at room temperature. Chlorosulfonic acid (5 g) was added dropwise and stirring was continued for a further 4 hours, after which the solvent was allowed to slowly evaporate until precipitation was seen. The mixture was left to recrystallised overnight and the ... | O=S(=O)(O)c1ccccc1-c1ccc(F)cc1 | null | null | null |
147,525 | ord_dataset-2069a3db775a4d9f9310aca092ecbad8 | null | 1986-01-01T00:08:00 | true | [CH:1]([C:3]1[CH:12]=[C:11]([CH3:13])[C:10]2[C:9]([CH3:15])([CH3:14])[CH2:8][CH2:7][C:6]([CH3:17])([CH3:16])[C:5]=2[C:4]=1[OH:18])=[O:2].[OH-].[K+].S(OC)(O[CH3:25])(=O)=O.Cl>C1(C)C=CC=CC=1>[CH:1]([C:3]1[CH:12]=[C:11]([CH3:13])[C:10]2[C:9]([CH3:14])([CH3:15])[CH2:8][CH2:7][C:6]([CH3:17])([CH3:16])[C:5]=2[C:4]=1[O:18][CH... | COS(=O)(=O)OC | Cc1cc(C=O)c(O)c2c1C(C)(C)CCC2(C)C | null | Cl | [K+] | [OH-] | 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 | 40 | 1.5 | Methylation. 2-Formyl-1-hydroxy-4,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalene (42 g, 0.17 mol) was stirred with toluene (656 mL), and potassium hydroxide 85% (16.8 g, 0.255 mol) was added in one portion. The mixture was heated to 40° C., dimethyl sulfate (32.13 g, 0.255 mol) added at 40°-45° C. during 0.5 h, and ... | COc1c(C=O)cc(C)c2c1C(C)(C)CCC2(C)C | null | 81.3 | null |
1,700,509 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | Br[C:2]1[C:3]([N:22]2[CH2:26][CH2:25][C@@H:24]([OH:27])[CH2:23]2)=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[F:28][C:29]1[C:30]([NH2:44])=[N:31][CH:32]=[C:33](B2OC(C)(C)C(C)(C)O2)[CH:34]=1>>[NH2:44][C:30]1[N:31]=[CH:32][C:33]([C:2]2[... | CC1(C)OB(c2cnc(N)c(F)c2)OC1(C)C | O=C(Nc1ccc(OC(F)(F)F)cc1)c1cnc(N2CC[C@@H](O)C2)c(Br)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 in an analogous fashion to that described in Example 169 using (R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 35.1) and 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine to afford a white amorphous powder. HPLC (Condition ... | Nc1ncc(-c2cc(C(=O)Nc3ccc(OC(F)(F)F)cc3)cnc2N2CC[C@@H](O)C2)cc1F | null | null | null |
1,028,164 | ord_dataset-83acb82dc5ba4f7aba439b9875aaac43 | null | 2011-01-01T00:02:00 | true | Cl[CH2:2][C:3]1[CH:29]=[CH:28][C:6]([C:7]([NH:9][C:10]2[S:11][C:12]([C:20]([CH:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[O:21])=[C:13]([C:15]3[O:16][CH:17]=[CH:18][CH:19]=3)[N:14]=2)=[O:8])=[CH:5][CH:4]=1.[CH3:30][NH:31][CH3:32].C1COCC1>>[CH3:30][N:31]([CH2:2][C:3]1[CH:29]=[CH:28][C:6]([C:7]([NH:9][C:10]2[S:11][C:1... | O=C(Nc1nc(-c2ccco2)c(C(=O)C2CCOCC2)s1)c1ccc(CCl)cc1 | CNC | 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 | 60 | 8 | Compound 478 (340 mg, 0.789 mmol) was added to a 2 mol/L solution of dimethylamine in THF (20 mL, 39.5 mmol), followed by stirring overnight at 60° C. The solvent was distilled away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (chloroform:methanol=19:1), follow... | CN(C)Cc1ccc(C(=O)Nc2nc(-c3ccco3)c(C(=O)C3CCOCC3)s2)cc1 | null | 44 | null |
6,031 | ord_dataset-a5669edbeffe43bf8514c1bfede8f882 | null | 1976-01-01T00:04:00 | true | [CH3:1][NH:2][CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4]1.CO.Cl.[O-:16][C:17]#[N:18].[K+]>O>[CH3:1][N:2]([CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4]1)[C:17]([NH2:18])=[O:16] | CNC1CCCc2ccccc21 | N#C[O-] | null | Cl | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | O | null | null | null | null | null | null | null | null | null | 25 | 0.75 | To a stirred solution of 8.05 grams (0.05 mole) of 1,2,3,4-tetrahydro-N-methyl-1-naphthylamine in 10 ml. of methanol is added a solution of 4.2 ml. of 12N hydrochloric acid (0.05 mole) in 35 ml. of water. The mixture is cooled in an ice-water bath while a solution of 4.46 grams (0.055 mole) of potassium cyanate in 15 m... | CN(C(N)=O)C1CCCc2ccccc21 | null | null | null |
926,238 | ord_dataset-cc0899cd744f4f7f8e7f2463560faad1 | null | 2009-01-01T00:12:00 | true | [C:1]([C:5]1([CH:11](C)[CH3:12])[CH:9]=[CH:8][CH:7]([CH3:10])[O:6]1)([CH3:4])([CH3:3])[CH3:2]>[Pd]>[C:1]([C:5]1([CH2:11][CH3:12])[CH2:9][CH2:8][CH:7]([CH3:10])[O:6]1)([CH3:4])([CH3:3])[CH3:2] | CC1C=CC(C(C)C)(C(C)(C)C)O1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Analogous to the procedure of example 2, by hydrogenation of 3.12 g (18.4 mmol) of 2-tert-butyl-2-isopropyl-5-methyl-2,5-dihydrofuran in the presence of 1.20 g (1.12 mmol) of 10% palladium on activated charcoal. Kugelrohr distillation of the reaction product provided at 70-80° C./20 mbar 3.42 g (93%) of the title compo... | CCC1(C(C)(C)C)CCC(C)O1 | null | 109.1 | null |
140,551 | ord_dataset-a2a0fbbcd49a46ffaa432d7ceae8a506 | null | 1986-01-01T00:02:00 | true | [N:1]([CH2:4][CH:5]([OH:10])[CH:6]([OH:9])[CH2:7][OH:8])=[N+:2]=[N-:3].CO[C:13](OC)([CH3:15])[CH3:14].S(=O)(=O)(O)O.[OH-].[Na+]>CC(C)=O>[N:1]([CH2:4][CH:5]([CH:6]1[CH2:7][O:8][C:13]([CH3:15])([CH3:14])[O:9]1)[OH:10])=[N+:2]=[N-:3] | [N-]=[N+]=NCC(O)C(O)CO | COC(C)(C)OC | null | O=S(=O)(O)O | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | null | null | null | null | null | null | null | null | null | null | 25 | 8 | A solution of 14.71 g of 4-azido-1,2,3-butanetriol in 30 ml of acetone is combined with 13.95 g of 2,2-dimethoxypropane, as well as 0.1 ml of concentrated sulfuric acid. The mixture is stirred overnight at room temperature, neutralized with 2N sodium hydroxide solution, and concentrated to dryness under vacuum. The res... | CC1(C)OCC(C(O)CN=[N+]=[N-])O1 | null | null | null |
445,242 | ord_dataset-ba7561dae3884c07a8beddd0b9f1222e | null | 1999-01-01T00:10:00 | true | Br[CH:2]([CH3:4])[CH3:3].[NH2:5][C:6](=[O:37])[C:7]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[O:18][CH2:19][C:20]([OH:22])=[O:21])[N:11]([CH2:23][C:24]2[CH:25]=[C:26]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:27]=[CH:28][CH:29]=2)[C:10]=1[CH3:36])=[O:8].[Na].C([O-])(O)=O.[Na+]>CN(C)C=O>[CH:2]([O:22][... | CC(C)Br | Cc1c(C(=O)C(N)=O)c2c(OCC(=O)O)cccc2n1Cc1cccc(-c2ccccc2)c1 | null | O=C([O-])O | [Na+] | [Na] | 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 | In a flask containing 15 ml of dimethylformamide was added with stirring 0.11 ml of 2-bromopropane and 500 mg. of ((3-(2-amino-1,2-dioxoethyl)-1-((1,1'-biphenyl)-3-ylmethyl)-2-methyl-1H-indol-4-yl)oxy)acetic acid, sodium salt. The reaction mixture was stirred at room temperature overnight. The reaction was incomplete. ... | Cc1c(C(=O)C(N)=O)c2c(OCC(=O)OC(C)C)cccc2n1Cc1cccc(-c2ccccc2)c1 | null | null | null |
1,745,038 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | [CH:1]1([C:4]([N:6]2[C:15]3[C:10](=[C:11]([O:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[C:12](B4OC(C)(C)C(C)(C)O4)=[CH:13][CH:14]=3)[CH2:9][CH2:8][C@@H:7]2[CH3:32])=[O:5])[CH2:3][CH2:2]1.[N+:33]([C:36]1[CH:37]=[N:38][NH:39][CH:40]=1)([O-:35])=[O:34].N1C=CC=CC=1>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.CN(C)C=O>[CH:1]1(... | O=[N+]([O-])c1cn[nH]c1 | C[C@H]1CCc2c(ccc(B3OC(C)(C)C(C)(C)O3)c2Oc2ccccc2)N1C(=O)C1CC1 | null | [Cu+2] | CC(=O)[O-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | CN(C)C=O | null | null | null | null | null | null | null | null | null | 90 | 8 | A 100-mL round-bottom flask equipped with a balloon filled with air was charged with (5)-cyclopropyl(2-methyl-5-phenoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroquinolin-1(2H)-yl)methanone (0.240 g, 0.55 mmol), 4-nitro-1H-pyrazole (0.188 g, 1.66 mmol), copper (II) acetate (0.301 g, 1.66 mmol), pyridin... | C[C@H]1CCc2c(ccc(-n3cc([N+](=O)[O-])cn3)c2Oc2ccccc2)N1C(=O)C1CC1 | null | 26.1 | null |
1,314,443 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | [Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([F:9])[C:3]=1[F:10].[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(Cl)Cl>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:4]([F:9])[C:3]=1[F:10] | OB(O)c1ccccc1 | Oc1ccc(Br)c(F)c1F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 48 | 4-bromo-2,3-difluorophenol (1.0 g, 0.0048 mol), phenylboronic acid (1.4 g, 0.012 mol), TEA (4.0 mL, 0.029 mol), cupric acetate (1.4 g, 0.0076 mol) and DCM (60 mL, 1 mol) were added to a 100 mL oven dried flask and the reaction was stirred at rt for 48 h. Reaction mixture was then filtered through celite. The filtrate w... | Fc1c(Br)ccc(Oc2ccccc2)c1F | null | null | null |
804,088 | ord_dataset-ed846b4b229e4bb09ad9dba95ad7ebeb | null | 2008-01-01T00:01:00 | true | [CH2:1]([C:3]1[CH:4]=[N:5][C:6]([NH:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18]C)=[C:14]([C:20]([F:23])([F:22])[F:21])[CH:13]=2)=[N:7][CH:8]=1)[CH3:2].[F:24][C:25]([F:36])([F:35])[O:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[CH2:30]Br>>[CH2:1]([C:3]1[CH:4]=[N:5][C:6]([N:9]([CH2:30][C:29]2[CH:32]=[CH:3... | CCc1cnc(NCCc2ccc(OC)c(C(F)(F)F)c2)nc1 | FC(F)(F)Oc1cccc(CBr)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 | Similarly prepared from 5-ethyl-N-{2-[4-methoxy-3-(trifluoromethyl)phenyl]ethyl}pyrimidin-2-amine and 3-trifluoromethoxy benzyl bromide. | CCc1cnc(N(CCc2ccc(O)c(C(F)(F)F)c2)Cc2cccc(OC(F)(F)F)c2)nc1 | null | null | null |
741,774 | ord_dataset-437aa6654d5044ddaef3346dc4c6e08a | null | 2006-01-01T00:11:00 | true | [Cl:1][CH2:2][C:3]1[C:8]([CH3:9])=[C:7](O)[C:6]([CH3:11])=[CH:5][N:4]=1.P(Br)(Br)([Br:14])=O.[OH-].[K+]>C(Cl)(Cl)Cl>[Br:14][C:7]1[C:6]([CH3:11])=[CH:5][N:4]=[C:3]([CH2:2][Cl:1])[C:8]=1[CH3:9] | O=P(Br)(Br)Br | Cc1cnc(CCl)c(C)c1O | null | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 130 | 3 | A neat mixture of 2-chloromethyl-3,5-dimethyl-pyridin-4-ol (8.2 g, 47.8 mmol) and POBr3 (60 g, 209 mmol) was stirred at 130° C. for 3 h. The resulting viscous oil was cooled to r.t. and poured onto ice water. The pH was adjusted to 10 with solid KOH. Work-up (CHCl3), drying (MgSO4) and evaporation afforded the title co... | Cc1cnc(CCl)c(C)c1Br | null | 77.6 | null |
1,168,164 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | FC1C=CC2N=C([C:9]3[C:10]([NH2:26])=[N:11][CH:12]=[C:13]([C:15]4[CH:16]=[N:17][N:18]([CH:20]5[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]5)[CH:19]=4)[CH:14]=3)SC=2C=1.Cl[C:30]1[S:31][C:32]2[C:38]([C:39]([F:42])([F:41])[F:40])=[CH:37][CH:36]=[CH:35][C:33]=2[N:34]=1>>[NH:23]1[CH2:22][CH2:21][CH:20]([N:18]2[CH:19]=[C:15]([C:13]... | FC(F)(F)c1cccc2nc(Cl)sc12 | Nc1ncc(-c2cnn(C3CCNCC3)c2)cc1-c1nc2ccc(F)cc2s1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Same procedure as 3-(6-fluorobenzothiazol-2-yl)-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine except using 2-chloro-7-trifluoromethyl-1,3-benzothiazole in place of 2-chloro-6-fluoro-1,3-benzothiazole to afford the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ=2.12-2.31 (m, 4H), 3.05-3.18 (m, 2... | Nc1ncc(-c2cnn(C3CCNCC3)c2)cc1-c1nc2cccc(C(F)(F)F)c2s1 | null | null | null |
1,735,030 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | Br[C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[CH:8][N:7]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)[C:6]=2[CH:17]=1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[C:29](B(O)O)=[CH:28][CH:27]=[N:26]2)=[CH:21][CH:20]=1>>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([N:25]2[C:29]([C:2]3[CH:3]=[CH:4][C:5]4[N:9]=[CH:8][N:7]([C:10]5[CH:1... | Fc1ccc(-n2cnc3ccc(Br)cc32)cc1 | OB(O)c1ccnn1-c1ccc(Cl)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 title compound, off-white solid (28 mg, 21%), MS (ISP) m/z=389.4 [(M+H)+], mp 180° C., was prepared in accordance with the general method of example 1 from 6-bromo-1-(4-fluoro-phenyl)-1H-benzo[d]imidazole (intermediate G) (100 mg, 344 μmol) and 1-(4-chloro-phenyl)-1H-pyrazol-5-ylboronic acid (intermediate D) (84.0 ... | Fc1ccc(-n2cnc3ccc(-c4ccnn4-c4ccc(Cl)cc4)cc32)cc1 | null | null | null |
310,238 | ord_dataset-081613ef79bd4110aacc146b4465f086 | null | 1995-01-01T00:05:00 | true | Br[C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9]([CH3:12])([CH3:11])[CH2:8][NH:7][C:6]=2[CH:13]=1.[CH3:14][N:15](C)C=O>C(N)CN.O>[C:14]([C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9]([CH3:12])([CH3:11])[CH2:8][NH:7][C:6]=2[CH:13]=1)#[N:15] | CC1(C)CNc2cc(Br)ccc2O1 | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | NCCN | null | null | null | null | null | null | null | null | null | 150 | 5 | A mixture of 480 mg of 6-bromo-3,4-dihydro-2,2-dimethyl-2H-1,4-benzoxazine, 206 mg of cuprous cyanide and 5 ml of N,N-dimethylformamide was stirred at 130° C. for 4 hours and further at 150° C. for 5 hours. This reaction mixture was diluted with 0.5 ml of ethylenediamine and 10 ml of water and extracted with benzene. T... | CC1(C)CNc2cc(C#N)ccc2O1 | null | null | null |
425,179 | ord_dataset-1ecf96d88f254270bff816ee7eeffef6 | null | 1999-01-01T00:02:00 | true | COC1C=CC(C[S:8][C@@H:9]2[CH2:13][N:12]([C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=3)=[O:15])[C@H:11]([C:27]([OH:29])=O)[CH2:10]2)=CC=1.[CH3:32][C:33]1([CH3:39])[CH2:38][NH:37][CH2:36][CH2:35][NH:34]1>>[CH3:32][C:33]1([CH3:39])[N:34]([C:14]([O:16][CH2:17][C:18]2[CH:19]=[CH:... | CC1(C)CNCCN1 | COc1ccc(CS[C@H]2C[C@@H](C(=O)O)N(C(=O)OCc3ccc([N+](=O)[O-])cc3)C2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Following a procedure similar to that described in Preparation 38, but using 0.35 g of (2S,4S)-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)-2-pyrrolidinecarboxylic acid, 0.15 g of N,N'-carbonyldiimidazole and 0.13 g of 2,2-dimethylpiperazine, 250 mg of the title compound were obtained as an amorphous solid. | CC1(C)CN(C(=O)[C@@H]2C[C@H](S)CN2C(=O)OCc2ccc([N+](=O)[O-])cc2)CCN1C(=O)OCc1ccc([N+](=O)[O-])cc1 | null | 106 | null |
105,161 | ord_dataset-4ac1b977dc504cb5a6a8e85d7d777c45 | null | 1983-01-01T00:05:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:11])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Cl.O=[C:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH:15]1[C:20](OCC)=[O:21]>S(=O)(=O)(O)O>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]2[C:14]3[CH2:19][CH2:18][NH:17][CH2:16][C:15]=3[C:20](=[O:21])[O:11][C:5]=2[CH:4]=1 | CCOC(=O)C1CNCCC1=O | COc1ccc(O)cc1OC | null | Cl | O=S(=O)(O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 0 | null | Prepared by the method described in Example 1 except that the 3,4-dimethoxyphenol (61.5 g, 0.40 moles) is added in one portion to an ice-cooled mixture of ethyl 4-oxo-3-piperidinecarboxylate hydrochloride (75 g, 0.36 moles) and 200 ml of 72% sulfuric acid. Recrystallization from acetonitrile yielded the product (71 g),... | COc1cc2oc(=O)c3c(c2cc1OC)CCNC3 | null | 75.5 | null |
179,657 | ord_dataset-ed5a3d1f8dc744759e7fa1c320a44e59 | null | 1988-01-01T00:11:00 | true | C[O:2][C:3](=[O:26])[CH:4]([C@@:6]1([CH2:24][CH3:25])[C@@H:15]2[N:10]([CH2:11][CH2:12][C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[N:16]([CH3:23])[C:14]=32)[CH2:9][CH2:8][CH2:7]1)[CH3:5].[OH-].[K+]>C(O)C>[CH2:24]([C@:6]1([CH:4]([CH3:5])[C:3]([OH:26])=[O:2])[C@@H:15]2[N:10]([CH2:11][CH2:12][C:13]3[C:22]4[C:17]... | CC[C@@]1(C(C)C(=O)OC)CCCN2CCc3c(n(C)c4ccccc34)[C@@H]21 | null | null | [K+] | [OH-] | 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 | The solution of 10.0 g. (0.028 moles) of (-)-(1S,12bS)-1-ethyl-12-methyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-1-yl-propionic acid methyl ester (prepared as described in Example 48) in 200 ml. of 96% of ethanol containing 2.5 g. (0.044 moles) of potassium hydroxide is refluxed for one hour. After cooling ... | CC[C@@]1(C(C)C(=O)O)CCCN2CCc3c(n(C)c4ccccc34)[C@@H]21 | null | 66 | null |
1,711,559 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])C#N.[C:12](=[O:15])([O-])[O-:13].[Na+].[Na+]>O.S(=O)(=O)(O)O>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[C:12]([OH:13])=[O:15] | COc1ccc(C#N)cc1F | O=C([O-])[O-] | null | O=S(=O)(O)O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | null | null | 3-Fluoro-4-methoxybenzonitrile (2.0 g, 13.2 mmol) in water (5 mL) and concentrated sulphuric acid (5 mL) was heated at 110° C. for 4 hours. The solution was then cooled to room temperature and neutralized with solid sodium carbonate. Acidification with glacial acetic acid leads to a white precipitate, which was collect... | COc1ccc(C(=O)O)cc1F | null | 90 | null |
1,112,520 | ord_dataset-375a420ee9b042918ddca20f02df37d3 | null | 2011-01-01T00:11:00 | true | [CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:19]([CH3:23])[C:20](O)=[O:21])[CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:27])=O>C(Cl)Cl.CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:19]([CH3:23])[C:20]([Cl:27])=[O:21])[CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])... | CC(C(=O)O)c1cc(OCc2ccccc2)cc(C(F)(F)F)c1 | O=C(Cl)C(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 0.25 | To a solution of 2-(3-benzyloxy-5-trifluoromethyl-phenyl)-propionic acid (1.4 g, 4.0 mmol) in CH2Cl2 was added oxalyl chloride (0.76 mL, 8.0 mmol), followed by 3 drops of DMF. After stirring for 15 minutes at room temperature, the mixture was concentrated to give the title compound. | CC(C(=O)Cl)c1cc(OCc2ccccc2)cc(C(F)(F)F)c1 | null | null | null |
902,832 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | [CH3:1][C:2]1([C:5](=O)[CH2:6][C:7]#[N:8])[CH2:4][CH2:3]1.Cl.[C:11]1([CH3:19])[CH:16]=[CH:15][C:14]([NH:17][NH2:18])=[CH:13][CH:12]=1>C(O)C>[CH3:1][C:2]1([C:5]2[CH:6]=[C:7]([NH2:8])[N:17]([C:14]3[CH:15]=[CH:16][C:11]([CH3:19])=[CH:12][CH:13]=3)[N:18]=2)[CH2:4][CH2:3]1 | Cc1ccc(NN)cc1 | CC1(C(=O)CC#N)CC1 | null | Cl | 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 | Heat to reflux a solution of 3-(1-methyl-cyclopropyl)-3-oxo-propionitrile (60 g, 487.2 mmol) and p-tolyl-hydrazine hydrochloride (78 g, 478.2 mmol) in ethanol (975 mL) for 4 hours. Evaporate the solvent and dissolve the remaining solid in water. Increase pH of the solution to pH 8 using a 1.0 N solution of sodium hydro... | Cc1ccc(-n2nc(C3(C)CC3)cc2N)cc1 | null | null | null |
1,184,817 | ord_dataset-9cd817a75dfc4fe7ad19d4232772d5ff | null | 2012-01-01T00:07:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:25]=3[NH:24][CH:23]=[C:22]4[CH2:26][CH2:27][C:28](O)=[O:29])[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[NH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.... | CCOC(=O)CN | CC(C)Oc1ccc(-c2nc(-c3cccc4c(CCC(=O)O)c[nH]c34)no2)cc1Cl | null | CN(C)C(On1nnc2cccnc21)=[N+](C)C | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 40 | 3 | To a solution of 3-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]propanoic acid (E1) (150 mg), ethyl glycinate (73 mg) and HATU (402 mg) in DCM (20 mL) was added DIPEA (0.2 mL). The reaction was stirred at 40° C. for 3 h. The reaction mixture was cooled to room temperature and partit... | CCOC(=O)CNC(=O)CCc1c[nH]c2c(-c3noc(-c4ccc(OC(C)C)c(Cl)c4)n3)cccc12 | null | 55.6 | null |
295,798 | ord_dataset-ec7cb3d5a8704f64b01d401ea555974f | null | 1994-01-01T00:09:00 | true | S(O)(O)(=O)=O.[N:6]1[C:10]2[CH2:11][CH2:12][CH:13](C(O)=O)[CH2:14][C:9]=2[NH:8][CH:7]=1.S(Cl)(Cl)=O>ClCCCl>[N:6]1[C:10]2[CH2:11][CH2:12][CH2:13][CH2:14][C:9]=2[NH:8][CH:7]=1 | O=C(O)C1CCc2nc[nH]c2C1 | null | null | O=S(=O)(O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCCl | O=S(Cl)Cl | null | null | null | null | null | null | null | null | null | 30 | null | 4,5,6,7-Tetrahydrobenzimidazole-5-carboxylic acid sulfate (1.32 g) was refluxed in 10 ml of 1,2-dichloroethane together with 1.78 g of thionyl chloride for 30 minutes, and the excess of thionyl chloride and the solvent were removed by distillation under reduced pressure. To the residue was added 10 ml of 1,2-dichloroet... | c1nc2c([nH]1)CCCC2 | null | null | null |
870,143 | ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | null | 2009-01-01T00:03:00 | true | Cl.[F:2][C:3]([F:23])([F:22])[C:4]1[CH:21]=[CH:20][CH:19]=[CH:18][C:5]=1[CH:6]([O:13][CH:14]1[CH2:17][NH:16][CH2:15]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[N-:24]=[C:25]=[O:26]>>[F:23][C:3]([F:2])([F:22])[C:4]1[CH:21]=[CH:20][CH:19]=[CH:18][C:5]=1[CH:6]([O:13][CH:14]1[CH2:17][N:16]([C:25]([NH:24][CH2:3][C:4]2[CH... | FC(F)(F)c1ccccc1C(OC1CNC1)c1ccccc1 | [N-]=C=O | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | This material was prepared 3-[2-(trifluoromethyl)benzhydryloxy]azetidine hydrochloride (133) and the corresponding isocyanate using the procedure described for compound (10). | O=C(NCc1ccccc1)N1CC(OC(c2ccccc2)c2ccccc2C(F)(F)F)C1 | null | null | null |
844,981 | ord_dataset-e2b35e721c2741999b0005d12691f9fe | null | 2008-01-01T00:10:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH:14]([CH3:16])[CH3:15])[C:5]2[O:9][CH:8]([CH2:10][NH2:11])[CH2:7][C:6]=2[C:12]=1[CH3:13].C(N(C(C)C)CC)(C)C.Cl[C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28]>>[CH2:30]([O:29][C:27](=[O:28])[NH:11][CH2:10][CH:8]1[CH2:7][C:6]2[C:12]([CH3:13])=[C:2]([Cl:1])[CH:3]=[C:4... | O=C(Cl)OCc1ccccc1 | Cc1c(Cl)cc(C(C)C)c2c1CC(CN)O2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | null | null | null | Treatment of (±)-1-(5-chloro-7-isopropyl-4-methyl-2,3-dihydro-1-benzofuran-2-yl)methanamine (3.41 g, 12.3 mmol) with diisopropylethylamine (1.99 g, 14.2 mmol) and benzyl chloroformate (2.42 g, 14.2 mmol) generally according to the procedure described for Intermediate 12 gave 3.74 g (81%) of (±)-benzyl(5-chloro-7-isopro... | Cc1c(Cl)cc(C(C)C)c2c1CC(CNC(=O)OCc1ccccc1)O2 | null | 81.3 | null |
764,186 | ord_dataset-7a8649d55889427e85b208ae89475895 | null | 2007-01-01T00:04:00 | true | C([O:3][C:4](=[O:36])[C:5]1[CH:10]=[C:9]([C@H:11]2[CH2:16][CH2:15][CH2:14][N:13]([C:17]([C:19]3[S:23][C:22]([C:24]4[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=4)=[N:21][C:20]=3[CH3:34])=[O:18])[CH2:12]2)[CH:8]=[CH:7][C:6]=1[CH3:35])C.C(=O)([O-])[O-].[K+].[K+].CO>O>[CH3:35][C:6]1[CH:7]=[CH:8][C:9]... | CCOC(=O)c1cc([C@H]2CCCN(C(=O)c3sc(-c4ccc(C(F)(F)F)cc4)nc3C)C2)ccc1C | null | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | O | null | null | null | null | null | null | null | null | null | 25 | null | A mixture of (R)-2-methyl-5-{1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carbonyl]-piperidin-3-yl}-benzoic acid ethyl ester (3.31 g, 6.41 mmol), potassium carbonate (1.77 g, 12.82 mmol), methanol (25 mL) and water (6 mL) was heated at reflux for 3 h, cooled to room temperature and concentrated under reduced pre... | Cc1ccc([C@H]2CCCN(C(=O)c3sc(-c4ccc(C(F)(F)F)cc4)nc3C)C2)cc1C(=O)O | null | 94.2 | null |
837,622 | ord_dataset-074f86301ec5441ab3b52d902ac06949 | null | 2008-01-01T00:09:00 | true | [C:1]([O:5][C:6]([C:8]1[O:9][C:10]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[C:11]=2[C:12]=1[CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[I:19]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[C:1]([O:5][C:6]([C:8]1[O:9][C:10]2[CH:17]=[CH:16][C:15]([I:19])=[C:14]([OH:18])[C:11]=2[C:12]=1[CH3:13])=[O:7])([CH3:4])([CH3:2])[CH3:3] | Cc1c(C(=O)OC(C)(C)C)oc2cccc(O)c12 | O=C1CCC(=O)N1I | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 0 | 3 | To 4.4 g (17.7 mmol) of 4-hydroxy-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester was added 40 mL of carbon tetrachloride, and the mixture was cooled with a water/ice bath while 1 equivalent of N-iodosuccinimide was added in small portions. After stirring at 0° C. for 3 h, the reaction mixture was loaded onto a ... | Cc1c(C(=O)OC(C)(C)C)oc2ccc(I)c(O)c12 | null | 38 | null |
1,374,796 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | 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.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[CH3:55][N:56]1[CH:60]=[C:59]([NH2:61])[CH:58]=[N:57]1>CN(C=O)C>[CH3:1][C:2]1[O:6][N:5]=[C:4... | Cn1cc(N)cn1 | Cc1onc(-c2ccccc2)c1COc1ccc(C(=O)O)cn1 | null | CN(C)C(On1nnc2ccccc21)=[N+](C)C | F[B-](F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 25 | 8 | To a solution of 6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid (100 mg, 0.32 mmol) in DMF (2 mL) were added 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (114 mg, 0.35 mmol), N,N-diisopropyl ethyl amine (275 μL, 1.6 mmol) and 1-methyl-1H-pyrazol-4-ylamine (1 M solution in MeOH, 0.35... | Cc1onc(-c2ccccc2)c1COc1ccc(C(=O)Nc2cnn(C)c2)cn1 | null | 40.9 | null |
31,232 | ord_dataset-56c07ce5503b46d1805bdf471f8f1c55 | null | 1977-01-01T00:10:00 | true | ClC1C=C(Cl)C(Cl)=CC=1O[C:11](=[O:18])[C@@H:12]1[CH2:16][CH2:15][C:14](=[O:17])[NH:13]1.[NH2:19][CH2:20][CH2:21][CH2:22][C:23]([NH2:25])=[O:24].ON1C2C=CC=CC=2N=N1.C(N1CCOCC1)C>CN(C)C=O>[NH:13]1[C:14](=[O:17])[CH2:15][CH2:16][C@H:12]1[C:11]([CH:22]([CH2:21][CH2:20][NH2:19])[C:23]([NH2:25])=[O:24])=[O:18] | O=C1CC[C@@H](C(=O)Oc2cc(Cl)c(Cl)cc2Cl)N1 | NCCCC(N)=O | null | CCN1CCOCC1 | On1nnc2ccccc21 | 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 | 3.9 g (12.65 mmols) of L-pyroglutamic acid 2,4,5-trichlorophenyl ester were added to a solution of 1.76 g (12.9 mmols) 4-amino butyric acid amide and 1.72 g (12.75 mmols) of 1-hydroxybenzotriazole and 1.65 ml of N-ethylmorpholine in 40 ml of dimethyl formamide. The solution was allowed to stand for 1 hour at room tempe... | NCCC(C(N)=O)C(=O)[C@@H]1CCC(=O)N1 | null | null | null |
858,334 | ord_dataset-faa0236be76c4501841c954527cd1b6c | null | 2008-01-01T00:12:00 | true | [CH3:1][O:2][C:3]1[N:8]=[C:7]2[CH:9]=[CH:10][NH:11][C:6]2=[CH:5][C:4]=1[B:12]([OH:14])[OH:13].[H-].[Na+].Cl[Si:18]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20]>O1CCCC1>[CH3:1][O:2][C:3]1[N:8]=[C:7]2[CH:9]=[CH:10][N:11]([Si:18]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[CH:19... | COc1nc2cc[nH]c2cc1B(O)O | CC(C)[Si](Cl)(C(C)C)C(C)C | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 0.5 | To a white suspension of 5-methoxy-1H-pyrrolo[3,2-b]pyridin-6-ylboronic acid (500 mg, 2.60 mmol) in tetrahydrofuran (25 mL) was added sodium hydride (281 mg, 11.72 mmol) in several portions at 0° C., the resulting light grey suspension was stirred for 30 min, followed by dropwise addition of chlorotriisopropylsilane (2... | COc1nc2ccn([Si](C(C)C)(C(C)C)C(C)C)c2cc1B(O)O | null | 99.4 | null |
887,917 | ord_dataset-d728a2f811c0424cbcdb5a84d02b93ae | null | 2009-01-01T00:06:00 | true | Cl.[CH2:2]([O:4][C:5]([C@@H:7]1[C@@H:11]([C:12](=[O:21])[NH:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[CH2:10][NH:9][CH2:8]1)=[O:6])[CH3:3].C(N(CC)C(C)C)(C)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>C(#N)C>[CH2:2]([O:4][C:5]([C@@H:7]1[C@@H:11]([C:12](=[O:21])[NH:13][C:14]2[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18... | CS(=O)(=O)Cl | CCOC(=O)[C@H]1CNC[C@@H]1C(=O)Nc1ccc(Cl)cc1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | CC#N | null | null | null | null | null | null | null | null | null | 25 | 18 | Compound 39c (1.44 g; 4.32 mmol) is dissolved in acetonitrile (10 ml) under addition of N,N-diisopropyl ethyl amine (2200 μl; 12.96 mmol). Methanesulfonylchloride (990 mg; 8.64 mmol) is added and the mixture is stirred for 18 h at 25° C. The reaction mixture is evaporated to dryness and purified with silica gel chromat... | CCOC(=O)[C@H]1CN(S(C)(=O)=O)C[C@@H]1C(=O)Nc1ccc(Cl)cc1 | null | null | null |
1,360,288 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | [Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]1[NH:16][C:15]([CH:17]3[CH2:21][CH2:20][CH2:19][NH:18]3)=[N:14][CH:13]=1)[CH:6]=[CH:5]2.[CH3:22][O:23][C:24]([NH:26][CH:27]([CH:31]([CH3:33])[CH3:32])[C:28](O)=[O:29])=[O:25].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>CN(C=O)C>[CH... | COC(=O)NC(C(=O)O)C(C)C | Brc1ccc2cc(-c3cnc(C4CCCN4)[nH]3)ccc2c1 | null | CN(C)C(On1nnc2cccnc21)=[N+](C)C | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN1CCOCC1 | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 16 | 5-(6-Bromo-naphthalen-2-yl)-2-pyrrolidin-2-yl-1H-imidazole (3.80 g), 2-methoxycarbonylamino-3-methyl-butyric acid (2.21 g), and HATU (5.06 g) were dissolved in anhydrous DMF (75 mL), and N-methylmorpholine (2.68 mL) was added. The reaction mixture was stirred at ambient temperature for 16 hours and evaporated under vac... | COC(=O)NC(C(=O)N1CCCC1c1ncc(-c2ccc3cc(Br)ccc3c2)[nH]1)C(C)C | null | 14.7 | null |
424,124 | ord_dataset-1a231de00bfe4443b547e1f03885ed41 | null | 1999-01-01T00:01:00 | true | [C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][NH2:17])[CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:25](Cl)(=[O:27])[CH3:26]>C(Cl)Cl>[C:25]([NH:17][CH2:16][CH2:15][N:12]1[CH2:13][CH2:14][CH:10]([CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:11]1)(=[O:27])[... | CC(=O)Cl | CC(C)(C)OC(=O)NCC1CCN(CCN)C1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 1 | 2-(3-tert-Butoxycarbonylaminomethylpyrrolidin-1-yl)ethylamine (1 g) was dissolved in methylene chloride (10 ml) and triethylamine (0.86 ml) was added. Then, a solution of acetyl chloride (0.29 ml) in methylene chlride was dropwise added under ice-cooling. The mixture was stirred at room temperature for 1 hr, and the re... | CC(=O)NCCN1CCC(CNC(=O)OC(C)(C)C)C1 | null | null | null |
1,112,386 | ord_dataset-375a420ee9b042918ddca20f02df37d3 | null | 2011-01-01T00:11:00 | true | [NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)O)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[CH3:18][O:19][C:20]([O:23][Si](C)(C)C)=[CH:21][CH3:22].C(Cl)Cl>CC#N.Cl[Ti](Cl)(Cl)Cl>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:21]([CH3:22])[C:20]([O:1... | OC(c1ccccc1)c1ccc2[nH]ncc2c1 | CC=C(OC)O[Si](C)(C)C | null | Cl[Ti](Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | ClCCl | null | null | null | null | null | null | null | null | null | null | 1 | To a solution of (1H-indazol-5-yl)(phenyl)methanol (180 mg, 0.71 mmol) and (1-methoxyprop-1-enyloxy)trimethylsilane (0.32 mL, 1.78 mmol) in 10 mL of dry MeCN was added TiCl4 (2.5 mL of 1.0 M DCM solution, 2.5 mmol) and then stirred 1 h. The reaction was incomplete so added 10 mL of DCM and additional (1-methoxyprop-1-e... | COC(=O)C(C)C(c1ccccc1)c1ccc2[nH]ncc2c1 | null | null | null |
1,196,967 | ord_dataset-4e81c470cc3b429faf5e1caa50f70a98 | null | 2012-01-01T00:08:00 | true | [O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=2)[CH2:5][CH:4]([CH2:17][N:18]2[CH:22]=[C:21]([C:23](O)=[O:24])[CH:20]=[N:19]2)[CH2:3]1.[NH2:26][C:27]1[C:28](=[O:38])[N:29]([CH2:35][CH2:36][CH3:37])[C:30](=[O:34])[NH:31][C:32]=1[NH2:33].CCN=C=NCCCN(C)C>CO>[NH2:33][C:32]1[NH:31][... | O=C(O)c1cnn(CC2CC(=O)N(c3cccc(C(F)(F)F)c3)C2)c1 | CCCn1c(=O)[nH]c(N)c(N)c1=O | null | CCN=C=NCCCN(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 8 | To a stirred solution of 1-[5-Oxo-1-(3-trifluoromethyl-phenyl)-pyrrolidin-3-ylmethyl]-1H-pyrazole-4-carboxylic acid (1 g, 2.83 mmol) and 5,6-Diamino-3-propyl-1H-pyrimidine-2,4-dione (521 mg, 2.83 mmol) in MeOH (40 mL) was added EDCI (813 mg, 4.24 mmol) under argon atmosphere. After stirring at overnight at room tempera... | CCCn1c(=O)[nH]c(N)c(NC(=O)c2cnn(CC3CC(=O)N(c4cccc(C(F)(F)F)c4)C3)c2)c1=O | null | 88.4 | null |
1,026,514 | ord_dataset-83acb82dc5ba4f7aba439b9875aaac43 | null | 2011-01-01T00:02:00 | true | Br[C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH:5]3[NH:12][C:13]3[C:18]([C:19]([NH2:21])=[O:20])=[CH:17][N:16]=[C:15]4[NH:22][CH:23]=[CH:24][C:14]=34)[CH2:3]1)[CH2:9]2.[CH2:25]([C:28]#[N:29])[CH2:26][OH:27]>C(N(CC)CC)C>[C:28]([CH2:25][CH2:26][O:27][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH:5]3[NH:1... | NC(=O)c1cnc2[nH]ccc2c1NC1C2CC3CC1CC(Br)(C3)C2 | N#CCCO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | 0.33 | To 4-[(5-bromoadamantan-2-yl)amino]-1H-pyrrolo[2,3-b]pyridine-5-carboxamide (52 mg) were added ethylene cyanhydrin (250 μl) and triethylamine (56 μl), and the mixture was stirred for 20 minutes using a microwave reaction system at 150° C. The reaction solution was cooled and purified by silica gel column chromatography... | N#CCCOC12CC3CC(C1)C(Nc1c(C(N)=O)cnc4[nH]ccc14)C(C3)C2 | null | null | null |
1,079,555 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | [CH2:1]([NH:3][C:4]1[N:5]=[CH:6][C:7]2[C:16](=[O:17])[N:15]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=3)[CH2:14][CH:13]3[N:9]([CH2:10][CH2:11][CH2:12]3)[C:8]=2[N:28]=1)[CH3:2].[H][H]>C(O)C.C1COCC1.[Pd]>[NH2:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][N:15]2[CH2:14][CH:13]3[N:9]([CH2:10][CH2:11][... | [H][H] | CCNc1ncc2c(n1)N1CCCC1CN(Cc1ccc([N+](=O)[O-])cc1)C2=O | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | Compound 5 (0.496 g, 1.30 mmol) obtained in Example 5 was dissolved in ethanol/THF=5/1 (12 mL), and the mixture was stirred under a stream of hydrogen gas for 2 hours after adding 10% palladium-on-carbon (Pd—C) (50% water, 276 mg, 0.130 mmol). Insolubles were separated by filtration through sellite, and the filtrate wa... | CCNc1ncc2c(n1)N1CCCC1CN(Cc1ccc(N)cc1)C2=O | null | 89.5 | null |
1,632,203 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[C:7]=2[F:13])[CH2:3][CH2:2]1.CCCCCC.C([Li])CCC.[C:25](=[O:27])=[O:26].C(=O)([O-])O.[Na+]>C1COCC1>[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([C:25]([OH:27])=[O:26])=[C:8]([F:12])[C:7]=2[F:13])[CH2:2][CH2:3]1 | Fc1cccc(OCC2CC2)c1F | O=C=O | null | O=C([O-])O | [Li]CCCC | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCCCC | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 1 | To a solution of 1-(cyclopropylmethoxy)-2,3-difluorobenzene (19.0 g) in THF (200 mL) was added 1.6 M n-butyllithium hexane solution (64.5 mL) at −78° C., and the mixture was stirred at the same temperature for 1 hr. To the reaction mixture was added dry ice, and the mixture was allowed to warm to room temperature, and ... | O=C(O)c1ccc(OCC2CC2)c(F)c1F | null | null | null |
1,076,362 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | [OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]=[C:4]([C:14]2[N:15]=[CH:16][S:17][CH:18]=2)[CH:3]=1.C(C1N=C(C2C=C(O[CH:38]3[CH2:56][CH:55]4[N:40]([C:41](=[O:61])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH:48]=[CH:49][CH:50]5[C:52]([C:58]([OH:60])=[O:59])([NH:53][C:54]4=[O:57])[CH2:51... | COc1ccc2c(OC3CC4C(=O)NC5(C(=O)O)CC5C=CCCCCCCC(=O)N4C3)cc(-c3nc(C(C)C)cs3)nc2c1 | COc1ccc2c(O)cc(-c3cscn3)nc2c1 | null | null | null | null | null | null | null | 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 4-hydroxy-7-methoxy-2-(thiazol-4-yl)quinoline and intermediate 7 following the procedure (Step F-H) reported for 18-[2-[4-(isopropyl)thiazol-2-yl]-7-methoxyquinolin-4-yloxy]-2,15-dioxo-3,16-diazatricyclo-[14.3.0.04,6]nonadec-7-ene-4-carboxylic acid 10: m/z=591 (M+H)+. | COc1ccc2c(OC3CC4C(=O)NC5(C(=O)O)CC5C=CCCCCCCC(=O)N4C3)cc(-c3cscn3)nc2c1 | null | null | null |
814,022 | ord_dataset-892acf7477db4d3a8a8559f004a7c0a2 | null | 2008-01-01T00:03:00 | true | C([N-]C(C)C)(C)C.[Li+].[CH2:9]([O:11][C:12](=[O:17])[CH2:13][O:14][CH2:15][CH3:16])[CH3:10].[CH2:18]([O:25][C:26]1[CH:33]=[CH:32][C:29]([CH:30]=[O:31])=[C:28]([CH3:34])[CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1COCC1.CCCCCCC.O1CCCC1>[CH2:9]([O:11][C:12](=[O:17])[CH:13]([O:14][CH2:15][CH3:16])[CH:30]([C:... | CCOCC(=O)OCC | Cc1cc(OCc2ccccc2)ccc1C=O | null | CC(C)[N-]C(C)C | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCCCCCC | null | null | null | null | null | null | null | null | null | null | 0.5 | To a −78° C. cold 2 M solution of lithium diisopropylamide (305 mmol) in THF/n-heptane (152.4 ml) was added a solution of ethoxy-acetic acid ethyl ester (45.2 ml, 331 mmol) in tetrahydrofuran (240 ml) within 1.5 h under an argon atmosphere. The mixture was stirred for 30 min. A solution of 4-benzyloxy-2-methyl-benzalde... | CCOC(=O)C(OCC)C(O)c1ccc(OCc2ccccc2)cc1C | null | 102.7 | null |
893,648 | ord_dataset-11068b1e475b4c5b82e56726ab0dddb7 | null | 2009-01-01T00:07:00 | true | C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:25]I.[CH2:27]([O:34][C:35](=[O:41])[NH:36][C@H:37]([CH3:40])[CH2:38]O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(Cl)Cl.O>[CH2:27]([O:34][C:35](=[O:41])[NH:36][C@H:37]([CH3:40])[CH2:38][I:25])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1 | II | C[C@H](CO)NC(=O)OCc1ccccc1 | null | c1c[nH]cn1 | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O | null | null | null | null | null | null | null | null | null | 0 | 3 | Triphenylphospine (24 g, 91.8 mmol) was added to a solution of imidazole (12.5 g, 184 mmol) in CH2Cl2 (231 ml), then was cooled to 0 degrees C. Iodine (23.3 g, 91.8 mmol) was added to the suspension. The reaction mixture turned yellow, then faintly brown. After 5 minutes ((R)-2-hydroxy-1-methyl-ethyl)-carbamic acid ben... | C[C@H](CI)NC(=O)OCc1ccccc1 | null | null | null |
879,509 | ord_dataset-3592bd645cd143ee8274cd0d834ae581 | null | 2009-01-01T00:05:00 | true | [N+]([C:4]1[CH:12]=[CH:11][C:7]2[N:8]=[CH:9][S:10][C:6]=2[CH:5]=1)([O-])=O.[OH-].[K+].ClC[C:17](=O)[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].Cl>CCO>[S:10]1[C:6]2[CH:5]=[CH:4][CH:12]=[CH:11][C:7]=2[NH:8]/[C:17](=[CH:18]/[C:19]([O:21][CH2:22][CH3:23])=[O:20])/[CH2:9]1 | CCOC(=O)CC(=O)CCl | O=[N+]([O-])c1ccc2ncsc2c1 | null | Cl | [K+] | [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 | 0 | 1 | steps 1 and 2—To a solution of 6-nitrobenzothiazole (10, 10.2 g, 57 mmol) in EtOH (500 mL) was added KOH (7.0 g, 125 mmol). The reaction was heated at reflux for 15 min then cooled to 0° C. Ethyl chloroacetoacetate (9.3 g, 57 mmol) was added and the mixture stirred at RT for 1 h. The reaction mixture was poured into 1N... | CCOC(=O)/C=C1\CSc2ccccc2N1 | null | 4.5 | null |
1,206,191 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | [CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6]Cl.[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([OH:21])[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9].C(N(C(C)C)CC)(C)C>O1CCCC1>[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([O:21][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:9])[... | CC(C)(C)OC(=O)N1CCC(O)CC1 | COCCOCCl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | C1CCOC1 | null | null | null | null | null | null | null | null | null | 0 | 1 | 10 ml of a tetrahydrofuran (THF) solution of 1.37 g (11 mmol) of 2-methoxyethoxymethyl chloride was added dropwise to 10 ml of a THF solution of 2.01 g (10 mmol) of N-t-butoxycarbonyl-4-hydroxypiperidine (manufactured by Aldrich) and 2.58 g (20 mmol) of diisopropylethylamine at 0° C. in a nitrogen atmosphere. After the... | COCCOCOC1CCN(C(=O)OC(C)(C)C)CC1 | null | 58.7 | null |
357,777 | ord_dataset-58ec5adfcd8648dc9e26ee757d289517 | null | 1997-01-01T00:03:00 | true | C(OC([NH:8][C@@H:9]1[C:15](=[O:16])[N:14]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([CH:24]([CH3:26])[CH3:25])=[CH:20][CH:19]=2)[C:13]2[CH:27]=[CH:28][CH:29]=[CH:30][C:12]=2[O:11][CH2:10]1)=O)(C)(C)C.[ClH:31]>C(OCC)(=O)C>[ClH:31].[NH2:8][C@@H:9]1[C:15](=[O:16])[N:14]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([CH:24]([CH3:26])[CH... | CC(C)c1ccc(CN2C(=O)[C@@H](NC(=O)OC(C)(C)C)COc3ccccc32)cc1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | 2 | 55 g of (S)-3-(tert-butoxycarbonylamino)-5-(p-isopropylbenzyl)-2,3,4,5-tetrahydro-1,5-benzoxazepin-4-one are dissolved in 180 ml of approximately 5 hydrochloric acid in ethyl acetate, foaming occurring. After stirring for two hours, the ochre-coloured suspension is concentrated and recrystallised from ether. The hygros... | CC(C)c1ccc(CN2C(=O)[C@@H](N)COc3ccccc32)cc1 | null | null | null |
1,742,420 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | O[N:2]=[C:3]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[CH3:15])[CH3:4].[ClH:16]>CO.[Pd]>[ClH:16].[NH2:2][CH:3]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[CH3:15])[CH3:4] | COC(=O)c1ccc(C(C)=NO)c(C)c1 | null | null | [Pd] | Cl | 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 | 8 | To a degassed solution of methyl 4-[N-hydroxyethanimidoyl]-3-methylbenzoate (0.348 g, 1.68 mmol) and 12.0 M aqueous hydrochloric acid (0.35 mL, 4.20 mmol) in methanol (15 mL) was added 10% palladium on carbon (0.11 g, 0.101 mmol). The reaction mixture was stirred under a balloon atmosphere of H2 overnight. All insolubl... | COC(=O)c1ccc(C(C)N)c(C)c1 | null | 99.8 | null |
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