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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
1,186,370 | ord_dataset-9cd817a75dfc4fe7ad19d4232772d5ff | null | 2012-01-01T00:07:00 | true | [CH3:1][C@@H:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[C:8]1[N:9]=[N:10][C:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=12.C(N(CC)CC)C.[N:31]1([C:37](Cl)=[O:38])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1>>[CH3:1][C@H:2]1[N:3]([C:8]2[C:13]3[CH:14]=[N:15][CH:16]=[CH:17][C:12]=3... | C[C@@H]1CNCCN1c1nnc(-c2ccccc2)c2ccncc12 | O=C(Cl)N1CCCCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | null | Using methods described in Example 18, and starting with (R)-4-(2-methylpiperazin-1-yl)-1-phenylpyrido[4,3-d]pyridazine 16 (125 mg, 409 μmol, triethylamine (80 μl, 614 μmol), and piperidine-1-carbonyl chloride (67 μl, 532 μmol) afforded (R)-(3-methyl-4-(1-phenylpyrido[4,3-d]pyridazin-4-yl)piperazin-1-yl)(piperidin-1-yl... | C[C@@H]1CN(C(=O)N2CCCCC2)CCN1c1nnc(-c2ccccc2)c2ccncc12 | null | null | null |
1,670,510 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [CH:1]1([C:4]([OH:6])=O)[CH2:3][CH2:2]1.CCN=C=NCCCN(C)C.Cl.Cl.[CH3:20][NH:21][NH:22][C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24].O>CN(C1C=CN=CC=1)C.ClCCCl>[CH:1]1([C:4]([N:21]([CH3:20])[NH:22][C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])=[O:6])[CH2:3][CH2:2]... | CNNC(=O)OCc1ccccc1 | O=C(O)C1CC1 | null | CCN=C=NCCCN(C)C | CN(C)c1ccncc1 | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCCl | O | null | null | null | null | null | null | null | null | null | 25 | 12 | Cyclopropanecarboxylic acid (600 mg, 6.97 mmol), DMAP (170 mg, 1.39 mmol) and EDC.HCl (1.19 g, 7.67 mmol) were added in that order to a stirred solution of benzyl 2-methylhydrazinecarboxylate hydrochloride (JOC, 2013, 78, 3541-3552.) (1.80 g, 8.37 mmol) in DCE (10 mL) and the reaction mixture was stirred at 25° C. for ... | CN(NC(=O)OCc1ccccc1)C(=O)C1CC1 | null | 92.5 | null |
506,098 | ord_dataset-631d58dab387485c8eb0db4c20a232b7 | null | 2001-01-01T00:06:00 | true | [NH2:1][C:2]1[N:3]=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.Cl[CH2:10][C:11](=O)[CH2:12][C:13]([O:15][CH3:16])=[O:14]>CO>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]2[N:3]([CH:10]=[C:11]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[N:1]=2)[N:4]=1 | Nc1ccc(Cl)nn1 | COC(=O)CC(=O)CCl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | 10.1 g of 3-amino-6-chloropyridazine was suspended in 120 ml of methanol; 23.5 g of methyl 4-chloroacetoacetate was added, followed by heating and refluxing for 20 hours. After cooling, the mixture was concentrated under reduced pressure; the residue was ajusted to pH 7 by the addition of an aqueous solution of sodium ... | COC(=O)Cc1cn2nc(Cl)ccc2n1 | null | 52 | null |
723,617 | ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | null | 2006-01-01T00:08:00 | true | [Br:1][C:2]1[CH:26]=[CH:25][C:5]([NH:6][C:7]2[S:8][C:9]3[CH2:23][CH2:22][C:12]4[N:13]=[C:14]([NH:16][C:17]([NH:19][CH2:20][CH3:21])=[O:18])[S:15][C:11]=4[C:10]=3[N:24]=2)=[CH:4][CH:3]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:6][C:7]2[S:8][C:9]3[CH:23]=[CH:22][C:12]4[N:13]=[... | CCNC(=O)Nc1nc2c(s1)-c1nc(Nc3ccc(Br)cc3)sc1CC2 | null | null | N#CC1=C(C#N)C(=O)C(Cl)=C(Cl)C1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | 20 | 2 | To a suspension of N-[7-(4-bromoanilino)-4,5-dihydro[1,3]thiazolo[4′,5′: 3,4]benzo[d][1,3]thiazol-2-yl]-N′-ethylurea (27 mg, 0.060 mmol) in toluene (2.0 mL) was added DDQ (28 mg, 0.125 mmol). The reaction mixture was stirred at about 20° C. for about 2 hrs. The reaction mixture was pumped down in vacuo and purified by ... | CCNC(=O)Nc1nc2ccc3sc(Nc4ccc(Br)cc4)nc3c2s1 | null | null | null |
286,644 | ord_dataset-3577d334f6eb4dc4bd73564fee3f0dfc | null | 1994-01-01T00:03:00 | true | [CH3:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=[O:13].[CH3:14][Mg]Br>CCOCC>[OH:13][C:7]1([CH3:14])[C:8]2[C:3](=[C:2]([CH3:1])[CH:11]=[C:10]([CH3:12])[CH:9]=2)[CH2:4][CH2:5][CH2:6]1 | C[Mg]Br | Cc1cc(C)c2c(c1)C(=O)CCC2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | null | null | Following the procedure of Example 1, step 1, 25.20 g (0.145 ml) of 5,7-dimethyltetralone in 200 ml of anhydrous ether was reacted with 60.3 ml of 3.0M methyl magnesium bromide in ether to give 26.64 g (97%) of the title product as an orange oil. NMR δ(CDCl3) 1.56 (3H, s), 1.70 (1H, s), 1.78-2.04 (4H, m), 2.20 (3H, s),... | Cc1cc(C)c2c(c1)C(C)(O)CCC2 | null | 97 | null |
394,165 | ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | null | 1998-01-01T00:03:00 | true | [CH3:1][C:2]1[C:7]([CH2:8][Cl:9])=[C:6]([CH3:10])[CH:5]=[CH:4][N:3]=1.ClC1C=CC=C(C(OO)=[O:19])C=1>C(Cl)(Cl)Cl>[CH3:1][C:2]1[C:7]([CH2:8][Cl:9])=[C:6]([CH3:10])[CH:5]=[CH:4][N+:3]=1[O-:19] | O=C(OO)c1cccc(Cl)c1 | Cc1ccnc(C)c1CCl | 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 | 0 | 4 | The 2,4-dimethyl-3-chloromethylpyridine (21.5 g, 138 mmol) was dissolved in CHCl3 (800 mL) and cooled under nitrogen to 0° C. and m-chloroperbenzoic acid (55%, 35 g) was added in small portions. The reaction was stirred for 4 hours. The solution was extracted twice with saturated aqueous sodium bicarbonate (500 mL). Th... | Cc1cc[n+]([O-])c(C)c1CCl | null | null | null |
570,926 | ord_dataset-5e1b2445a3d94ea592ddf2c284118a1e | null | 2002-01-01T00:11:00 | true | [F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[C:6]([N:8]1[CH2:24][CH2:23][C:11]2([C:15](=[O:16])[NH:14][CH2:13][CH:12]2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:10][CH2:9]1)=[O:7].[CH3:34]I>>[F:31][C:28]([F:29])([F:30])[C:26]1[CH:25]=[C:5]([CH:4]=[C:3]([C:... | CI | O=C(c1cc(C(F)(F)F)cc(C(F)(F)F)c1)N1CCC2(CC1)C(=O)NCC2c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound, MS: m/e=485.3 (M+H+), was prepared in accordance with the general method of example 99 from (rac)-8-(3,5-bis-trifluoromethyl-benzoyl)-4-phenyl-2,8-diaza-spiro[4.5]decan-1-one and methyl iodide. | CN1CC(c2ccccc2)C2(CCN(C(=O)c3cc(C(F)(F)F)cc(C(F)(F)F)c3)CC2)C1=O | null | null | null |
456,638 | ord_dataset-2501595af7f242268dbaab34c9e7ae56 | null | 2000-01-01T00:02:00 | true | [CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]([NH2:21])[CH2:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])O.[Na+].C(OC(N1[C:36](=[O:37])[C:35]2=[CH:38][CH:39]=[CH:40][CH:41]=[C:34]2[C:33]1=[O:42])=O)C>C(#N)C.O>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]([N:21]3... | CCOC(=O)N1C(=O)c2ccccc2C1=O | COc1ccc(C(N)CS(C)(=O)=O)cc1OC1CCCC1 | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | O | null | null | null | null | null | null | null | null | null | null | null | 2-[1-(3-Cyclopentyloxy-4-methoxyphenyl)-2-methylsulfonylethyl]isoindoline-1,3-dione was prepared by the procedure of Example 5 from 1-(3-cyclopentyloxy-4-methoxyphenyl)-2-methylsulfonylethylamine (1.0 g, 3.2 mmol), sodium hydrogen carbonate (281 mg, 3.34 mmol) and N-ethoxycarbonyl phthalimide (732 mg, 3.3 mmol) in acet... | COc1ccc(C(CS(C)(=O)=O)N2C(=O)c3ccccc3C2=O)cc1OC1CCCC1 | null | null | null |
1,559,218 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | C[O:2][C:3](=[O:30])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:26](=[CH:27][CH:28]=1)[O:25][C:11]1([CH2:17][CH2:16][CH2:15][N:14]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:13][CH2:12]1)[CH2:10][C:9]2=[O:29].Cl>CC(O)=O>[CH2:18]([N:14]1[CH2:15][CH2:16][CH2:17][C:11]2([CH2:10][C:9](=[O:29])[C:8]3[C:26](=[CH:27... | COC(=O)/C=C/c1ccc2c(c1)C(=O)CC1(CCCN(Cc3ccccc3)CC1)O2 | null | null | Cl | 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 | (±)-(E)-3-[1′-Benzyl-4-oxo-spiro(chromane-2,4′-azepane)-6-yl]-acrylic acid methyl ester (480 mg, 1.18 mmol) was hydrolyzed with aqueous 20% HCl solution and AcOH following the procedure described in Example 22, Step A, giving (±)-(E)-3-[1′-benzyl-4-oxo-spiro(chromane-2,4′-azepane)-6-yl]-acrylic acid (490 mg) as a white... | O=C(O)/C=C/c1ccc2c(c1)C(=O)CC1(CCCN(Cc3ccccc3)CC1)O2 | null | 106.1 | null |
713,971 | ord_dataset-c8a367b56b4f406b878f51867b157d19 | null | 2006-01-01T00:06:00 | true | [CH3:1][O:2][C:3]1[C:4](=[O:37])[C:5]([CH3:36])=[C:6]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:32]C(=O)C)=[C:17]([CH:31]=2)[C:18]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]([F:30])([F:29])[F:28])=[O:19])[C:7](=[O:11])[C:8]=1[O:9][CH3:10].C(=O)([O-])O.[Na+]>CO.O>[CH3:1][O:2][C:3]1[C:4](=[O:37])[C:5]([CH3:... | COC1=C(OC)C(=O)C(Cc2ccc(OC(C)=O)c(C(=O)Nc3ccccc3C(F)(F)F)c2)=C(C)C1=O | null | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CO | null | null | null | null | null | null | null | null | null | null | null | N-[5-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-2-trifluoromethylaniline (0.100 g, 0.193 mmol) was dissolved in methanol (6 ml) and after adding thereto an aqueous saturated sodium hydrogencarbonate solution (3 ml), the solution was stirred at room temperature for 3 hours. After the completio... | COC1=C(OC)C(=O)C(Cc2ccc(O)c(C(=O)Nc3ccccc3C(F)(F)F)c2)=C(C)C1=O | null | 97.9 | null |
956,722 | ord_dataset-ed65749688da45af8a8432967b017729 | null | 2010-01-01T00:05:00 | true | C([O:3][C:4]([C:6]1[C:7](=[O:18])[NH:8][N:9]=[C:10]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[CH:11]=1)=O)C.O.[NH2:20][NH2:21]>C(O)C>[O:18]=[C:7]1[C:6]([C:4]([NH:20][NH2:21])=[O:3])=[CH:11][C:10]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[N:9][NH:8]1 | CCOC(=O)c1cc(-c2ccncc2)n[nH]c1=O | NN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | 25 | null | 10 g of 3-oxo-6-pyridin-4-yl-2,3-dihydro-pyridazine-4-carboxylic acid ethyl ester are dissolved in 150 ml of ethanol, 4.2 ml of hydrazine hydrate is added and the mixture is refluxed for 5 hours. After cooling to room temperature, the solid is collected by filtration and dried in vacuo at 40° C. | NNC(=O)c1cc(-c2ccncc2)n[nH]c1=O | null | null | null |
765,919 | ord_dataset-7a8649d55889427e85b208ae89475895 | null | 2007-01-01T00:04:00 | true | [CH3:1][O:2][C:3](=[O:11])[CH2:4][O:5][CH2:6]/[CH:7]=[CH:8]\[CH2:9][OH:10].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:11])[CH2:4][O:5][CH2:6]/[CH:7]=[CH:8]/[CH:9]=[O:10] | COC(=O)COC/C=C\CO | null | null | O=[Cr](=O)([O-])Cl | c1cc[nH+]cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccccc1 | null | null | null | null | null | null | null | null | null | null | 25 | 23 | To a solution of 1.57 g of 2-[4-hydroxy-(Z)-2-buten-1-yloxy]acetic acid methyl ester in 157 ml of benzene, 7.90 g of celite and 4.87 g of pyridinium chlorochromate were added, followed by stirring at room temperature for 23 hours. The insoluble matter was removed by filtration and the solvent in the filtrate was evapor... | COC(=O)COC/C=C/C=O | null | 20.1 | null |
1,682,296 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:17][C:18]([OH:20])=[O:19])[CH:6]=[CH:7][C:8]=1OS(C(F)(F)F)(=O)=O.[CH3:21][C:22]1[CH:27]=[C:26]([Sn](CCCC)(CCCC)CCCC)[CH:25]=[CH:24][N:23]=1.CS(C)=O>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:1][O:2][C:3]1[CH:4]=[C:5](... | CCCC[Sn](CCCC)(CCCC)c1ccnc(C)c1 | COc1cc(CC(=O)O)ccc1OS(=O)(=O)C(F)(F)F | null | Cl[Pd]Cl | [Fe+2] | c1ccc(P(c2ccccc2)[c-]2cccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 110 | 20 | To the mixture of 2-(3-methoxy-4-(trifluoromethylsulfonyloxy)phenyl)acetic acid 182-2 (590 mg, 1.9 mmol) and 2-methyl-4-(tributylstannyl)pyridine (730 mg, 1.9 mmol) in DMF (2.0 mL) was added [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (33 mg, 0.04 mmol). The reaction was stirred at 110° C. for 20 hours.... | COc1cc(CC(=O)O)ccc1-c1ccnc(C)c1 | null | null | null |
1,376,734 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | [CH3:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[O:9][C:10]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:11]=2[N:12]=1.C(Cl)(Cl)Cl.ClC1C=CC=C(C(OO)=[O:33])C=1>C(OCC)(=O)C>[CH3:1][C:2]1[CH:3]=[N+:4]([O-:33])[CH:5]=[CH:6][C:7]=1[C:8]1[O:9][C:10]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:18])[F:19])=[CH:... | O=C(OO)c1cccc(Cl)c1 | Cc1cnccc1-c1nc2cc(C(F)(F)F)ccc2o1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | 25 | 3 | To a mixture of 0.20 g of 2-(3-methylpyridin-4-yl)-5-(trifluoromethyl)benzoxazole and 4 ml of chloroform, 0.30 g of 65% m-chloroperbenzoic acid was added while ice-cooling. The reaction mixture was stirred at room temperature for three hours, then diluted with ethyl acetate, and washed with 5% aqueous solution of sodiu... | Cc1c[n+]([O-])ccc1-c1nc2cc(C(F)(F)F)ccc2o1 | null | 80.4 | null |
829,166 | ord_dataset-47bd90bf5ec74fcd99ce250a56e18c8f | null | 2008-01-01T00:07:00 | true | [SH:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)#[N:14]>N1C=CC=CC=1>[CH3:12][O:11][C:9]1[CH:8]=[CH:7][C:3]2[C:4](=[O:6])[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[S:1][C:2]=2[CH:10]=1 | N#Cc1ccccn1 | COc1ccc(C(=O)O)c(S)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 2-mercapto-4-methoxybenzoic acid (1.4 g, 7.9 mmol), 2-cyanopyridine (0.89 g, 8.5 mmol) and pyridine (10 ml) was refluxed for 10 hrs as described in Example 9. After cooling, the precipitated crystals were collected by filtration and recrystallized from hexane-tetrahydrofuran to give the titled compound (1.... | COc1ccc2c(=O)nc(-c3ccccn3)sc2c1 | null | 46.8 | null |
945,592 | ord_dataset-ed680843f6d14f5c9901869b2a06b4a4 | null | 2010-01-01T00:03:00 | true | [CH3:1][NH2:2].[F:3][C:4]([F:34])([F:33])[O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:23][CH2:22][N:21]([C:24]([O:26][CH2:27][C:28]([O:30]CC)=O)=[O:25])[CH2:20][CH2:19]3)=[CH:14][CH:13]=2)=[CH:8][CH:7]=1>O1CCCC1.CO>[F:3][C:4]([F:33])([F:34])[O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:17]=[CH:16... | CN | CCOC(=O)COC(=O)N1CCN(c2ccc(-c3ccc(OC(F)(F)F)cc3)cc2)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CO | null | null | null | null | null | null | null | null | null | null | 12 | 7.10 ml (14.15 mmol) of a solution of methylamine (2M) in tetrahydrofuran are added to a solution of 1.60 g (3.54 mmol) of 2-(ethyloxy)-2-oxoethyl 4-{4′-[(trifluoro-methyl)oxy]-4-biphenylyl}-1-piperazinecarboxylate, prepared in step 1.3., in 14 ml of methanol. Stirring is continued at room temperature for 12 hours. Aft... | CNC(=O)COC(=O)N1CCN(c2ccc(-c3ccc(OC(F)(F)F)cc3)cc2)CC1 | null | null | null |
863,740 | ord_dataset-b8b98725045d45bdbd73512048f4b47e | null | 2009-01-01T00:02:00 | true | [CH3:1][C:2]1([CH:7]([CH3:11])[C:8]([OH:10])=O)[O:6][CH2:5][CH2:4][O:3]1.C(Cl)(=O)C(Cl)=O.[CH2:18]([NH2:26])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>ClCCl.N1C=CC=CC=1>[CH3:1][C:2]1([CH:7]([CH3:11])[C:8]([NH:26][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:10])[O:3][CH2:4][CH2:5][O:6]1 | CC(C(=O)O)C1(C)OCCO1 | NCCc1ccccc1 | null | O=C(Cl)C(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 0.08 | 2-(2-Methyl-[1,3]dioxolan-2-yl)-propionic acid of Example 1b (1.60 g, 10 mmol) in dry dichloromethane (15 mL) was cooled to 0° C. under an argon atmosphere. A solution of oxalyl dichloride (2.92 g, 2.0 mL, 23.0 mmol) in dichloromethane (5 mL) was added dropwise. After 5 min at 0° C., the mixture was allowed to warm to ... | CC(C(=O)NCCc1ccccc1)C1(C)OCCO1 | null | 68.7 | null |
1,301,026 | ord_dataset-78c3f723155a4347a902b53bcee1524d | null | 2013-01-01T00:06:00 | true | [H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.O=[C:18]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19]1>O1CCCC1>[C:26]([O:25][C:23]([N:20]1[CH2:21][CH2:22][C:18](=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:19]1)=[O:24])([CH3:29])([CH3:27])[CH3:28] | CC(C)(C)OC(=O)N1CCC(=O)C1 | CCOC(=O)CP(=O)(OCC)OCC | 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 | 0 | 1 | A flask was charged with NaH (50 g, 1.25 mol, 60% in mineral oil) and tetrahydrofuran (2,500 ml) and cooled to 0° C. A solution of ethyl 2-(diethoxyphosphoryl)acetate (260 g, 1.16 mol) in tetrahydrofuran F (200 ml) was added dropwise. The resulting solution was allowed stir for 1 h at 0° C. Then a solution of tert-buty... | CCOC(=O)C=C1CCN(C(=O)OC(C)(C)C)C1 | null | null | null |
929,278 | ord_dataset-d8a5dc784dde4465894ec7c69d2e3ba6 | null | 2010-01-01T00:01:00 | true | [F:1][C:2]([F:21])([F:20])[C:3]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][NH2:19])=[CH:14][CH:13]=2)[N:4]=1.[CH:22]1([S:27](Cl)(=[O:29])=[O:28])[CH2:26][CH2:25][CH2:24][CH2:23]1>>[F:21][C:2]([F:1])([F:20])[C:3]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]([C:12]2[CH:17]=... | NCc1ccc(-n2nc(C(F)(F)F)c3c2CCCC3)cc1 | O=S(=O)(Cl)C1CCCC1 | null | null | null | null | null | null | null | 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-[3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl]phenyl}methyl)amine and cyclopentanesulphonyl chloride using a similar procedure to that described for Example 88. | O=S(=O)(NCc1ccc(-n2nc(C(F)(F)F)c3c2CCCC3)cc1)C1CCCC1 | null | null | null |
1,223,909 | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | null | 2012-01-01T00:11:00 | true | Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[CH3:9][C:10]1[N:11]=[CH:12][NH:13][CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[Cl:8][C:6]1[CH:7]=[C:2]([N:13]2[CH:14]=[C:10]([CH3:9])[N:11]=[CH:12]2)[N:3]=[CH:4][N:5]=1 | Clc1cc(Cl)ncn1 | Cc1c[nH]cn1 | null | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | A mixture of 4,6-dichloropyrimidine (11.92 g, 80 mmol), 4-methyl-1H-imidazole (6.57 g, 80 mmol), and cesium carbonate (26.1 g, 80 mmol) was stirred in DMF (50 mL) at room temperature for 18 h. The reaction was diluted into 200 mL water and extracted three times with 200 mL EtOAc. The combined organic layers were concen... | Cc1cn(-c2cc(Cl)ncn2)cn1 | null | 36.6 | null |
645,075 | ord_dataset-c975a50a7600448fabd558f4a94a3e29 | null | 2004-01-01T00:08:00 | true | [NH2:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[C:5]([CH:7]1[CH2:12][CH2:11][N:10]([CH3:13])[CH2:9][CH2:8]1)=[O:6].[F:17][C:18]([F:29])([F:28])[C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1>>[F:17][C:18]([F:28])([F:29])[C:19]1[CH:27]=[CH:26][C:22]([C:23]([NH:1][C:2]2[CH:3]=[C:4]([CH:14]=[CH:15][CH... | CN1CCC(C(=O)c2cccc(N)c2)CC1 | O=C(Cl)c1ccc(C(F)(F)F)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Beginning with 4-[3-aminobenzoyl]-1-methylpiperidine (50 mg, 0.229 mmol) and 4-(trifluoromethyl)benzoyl chloride (102 μl, 0.687 mmol), 88.0 mg (98%) of the title compound were recovered. | CN1CCC(C(=O)c2cccc(NC(=O)c3ccc(C(F)(F)F)cc3)c2)CC1 | null | 98.4 | null |
1,578,249 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([CH2:14]Cl)[N:11]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:10][C@H:9]1[CH3:23])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:24][C@H:25]1[CH2:29][CH2:28][NH:27][CH2:26]1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([CH2:14][N:27]2[CH2:28][CH2:29][C@H:25]([F:24])[CH2:26]2)[N:... | F[C@H]1CCNC1 | C[C@@H]1CN(Cc2ccccc2)[C@@H](CCl)CN1C(=O)OC(C)(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared following similar methods to those described in Preparation 352 starting from (2R,5R)-4-benzyl-5-chloromethyl-2-methyl-piperazine-1-carboxylic acid tert-butyl ester (300 mg, 0.88 mmol) and (S)-3-fluoro-pyrrolidine (165 mg, 1.32 mmol). MS: [M+H]+=392. | C[C@@H]1CN(Cc2ccccc2)[C@@H](CN2CC[C@H](F)C2)CN1C(=O)OC(C)(C)C | null | null | null |
156,403 | ord_dataset-36f7bef430f14c2e8db5e3f7c3640d9b | null | 1987-01-01T00:04:00 | true | Cl[CH2:2][CH:3]([OH:20])[CH2:4][N:5]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH-].[Na+].C(Cl)(Cl)Cl>O>[CH2:6]([N:5]([CH2:4][CH:3]1[CH2:2][O:20]1)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1 | OC(CCl)CN(Cc1ccccc1)Cc1ccccc1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | 50.7 g (0.175 mol) of 1-chloro-3-dibenzylamino-2-propanol and 9.5 g (0.24 mol) of sodium hydroxide in 5 ml of water are stirred together for one hour at 95° c. After the addition of 50 ml of chloroform and 20 ml of water, the phases are separated and the organic phase is washed with 20 ml of water, dehydrated with sodi... | c1ccc(CN(Cc2ccccc2)CC2CO2)cc1 | null | 76 | null |
1,341,352 | ord_dataset-08852243bba44cb28769a5833f1515fe | null | 2013-01-01T00:09:00 | true | [Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH2:12]([NH:19][C:20]([C:22]1[S:26][C:25]([NH2:27])=[N:24][C:23]=1[CH3:28])=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[CH2:12]([NH:19][C:20]([C:22]1[S:26][C:25]([NH:27][C:4](=[O:5])[C:3]2[CH:7]=[CH:8][C:9]([Cl:11])=[CH:10][C:2]=2[Cl:1])... | O=C(Cl)c1ccc(Cl)cc1Cl | Cc1nc(N)sc1C(=O)NCc1ccccc1 | null | null | null | null | null | null | null | 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 as described in Example 2, making variations only as required to use 2,4-dichlorobenzoyl chloride in place of benzoyl chloride to react with 2-amino-4-methylthiazole-5-carboxylic acid benzylamide, the title compound was obtained as a white solid in 21% yield; 1H NMR (CDCl3, 300 MHz) δ 7.74 (d, J... | Cc1nc(NC(=O)c2ccc(Cl)cc2Cl)sc1C(=O)NCc1ccccc1 | null | 21 | null |
882,228 | ord_dataset-3592bd645cd143ee8274cd0d834ae581 | null | 2009-01-01T00:05:00 | true | [CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:29]([O:31][CH3:32])=[O:30])=[CH:12][C:13]=3[N:14]3[CH2:20][C:19]([C:21]([O:23]C)=[O:22])=[CH:18][C:17]4[CH:25]=[CH:26][CH:27]=[CH:28][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Li+].[OH-]>CN(C)C=O>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:29]([O:31][CH3:32])=[O:... | COC(=O)C1=Cc2ccccc2-c2c(C3CCCCC3)c3ccc(C(=O)OC)cc3n2C1 | null | null | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 50 | null | Methyl 13-cyclohexyl-6-(methoxycarbonyl)-7H-indolo[2,1-a][2]benzazepine-10-carboxylate (308 mg, 0.72 mmol) was dissolved in N,N-dimethylformamide (5 mL) and treated with LiOH (173 mg, 7.2 mmol). The mixture was heated at 50° C. for 4 hr, afterwhich the solvent was removed in vacuo. The residue was dissolved in H2O (5 m... | COC(=O)c1ccc2c(C3CCCCC3)c3n(c2c1)C=C(C(=O)O)Cc1ccccc1-3 | null | 96.9 | null |
1,169,449 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | [H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([C:11]2[NH:12][C:13]([CH2:16][CH2:17][C:18]3[N:19]([S:29]([N:32]([CH3:34])[CH3:33])(=[O:31])=[O:30])[CH:20]=[C:21]([CH2:23][C:24]([CH3:28])([CH3:27])[CH2:25][CH3:26])[N:22]=3)=[N:14][N:15]=2)[CH:7]=[CH:8][C:9]=1[F:10].[CH3:35]I>CN(C=O)C>[F:3][C:4]1[CH:5]=[C:6]([C:11]2[N:12]=[C:13]([CH... | CCC(C)(C)Cc1cn(S(=O)(=O)N(C)C)c(CCc2nnc(-c3ccc(F)c(F)c3)[nH]2)n1 | CI | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | 0.5 | Sodium hydride (21 mg, 0.87 mmol) was added to a solution of 2-{2-[5-(3,4-difluorophenyl)-4H-1,2,4-triazol-3-yl]ethyl}-4-(2,2-dimethylbutyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide (135 mg, 0.29 mmol) in DMF (4 mL) at 0° C., and the reaction was stirred at rt for 30 min. Methyliodide (0.09 mL, 1.4 mmol) was added and s... | CCC(C)(C)Cc1cn(S(=O)(=O)N(C)C)c(CCc2nc(-c3ccc(F)c(F)c3)nn2C)n1 | null | null | null |
1,663,204 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [I:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([OH:9])=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:16]=[C:15](Cl)[N:14]=[CH:13][N:12]=1.C([O-])([O-])=O.[K+].[K+]>CC(N(C)C)=O>[Cl:10][C:11]1[CH:16]=[C:15]([O:9][C:5]2[C:6]([CH3:8])=[N:7][C:2]([I:1])=[CH:3][CH:4]=2)[N:14]=[CH:13][N:12]=1 | Clc1cc(Cl)ncn1 | Cc1nc(I)ccc1O | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)N(C)C | null | null | null | null | null | null | null | null | null | null | 110 | 16 | 6-Iodo-2-methylpyridin-3-ol (2.00 g, 8.51 mmol) and 4,6-dichloropyrimidine (5.00 g, 33.6 mmol) were dissolved in DMA (40 mL) and sonicated and sparged with Ar for 10 min. K2CO3 (2.00 g, 14.5 mmol) was added and the reaction mixture was stirred at 110° C. for 16 h. The mixture was partitioned between water (260 mL) and ... | Cc1nc(I)ccc1Oc1cc(Cl)ncn1 | null | 94.7 | null |
1,545,202 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:21])=[C:8]2[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:13][S:12][C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2].[Br:22]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:21])=[C:8]2[C:14]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:2... | CCOC(=O)c1ncc2snc(-c3ccccc3)c2c1O | O=C1CCC(=O)N1Br | null | O=C(OOC(=O)c1ccccc1)c1ccccc1 | 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 | null | 4 | To a solution of 4-hydroxy-3-phenyl-isothiazolo[5,4-c]pyridine-5-carboxylic acid ethyl ester (1.07 g, 3.56 mmol) in CCl4 was added N-bromosuccinimide (666 mg, 3.74 mmol) and benzoyl peroxide (43.1 mg, 0.18 mmol). The reaction mixture was refluxed with stirring for 4 h. After cooling to r. t. the mixture was filtered. T... | CCOC(=O)c1nc(Br)c2snc(-c3ccccc3)c2c1O | null | 80 | null |
689,575 | ord_dataset-6214af00a7eb47f3887ef21a94320a7e | null | 2005-01-01T00:11:00 | true | C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])=[CH:10][C:9]=1[NH:21][C:22](=[O:36])[CH2:23][C:24]([C:26]1[N:27]=[C:28]([N:31]2[CH:35]=[CH:34][N:33]=[CH:32]2)[S:29][CH:30]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:11]1[CH:1... | CC(C)(C)OC(=O)Nc1ccc(-c2ccccc2F)cc1NC(=O)CC(=O)c1csc(-n2ccnc2)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 | null | null | Prepared from {2′-fluoro-3-[3-(2-imidazol-1-yl-thiazol-4-yl)-3-oxo-propionylamino]-biphenyl-4-yl}-carbamic acid tert.-butyl ester (Example K91) by treatment with TFA in CH2Cl2 according to the general procedure M. Obtained as a light yellow solid (46 mg). | O=C1CC(c2csc(-n3ccnc3)n2)=Nc2ccc(-c3ccccc3F)cc2N1 | null | null | null |
217,878 | ord_dataset-67ed03c283094854909157b1038e38e3 | null | 1990-01-01T00:10:00 | true | C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([OH:11])[CH:5]=1.CO.O.[NH2:16][NH2:17]>O>[OH:11][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[OH:10])[C:3]([NH:16][NH2:17])=[O:2] | NN | COC(=O)c1ccc(O)c(O)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | O | null | null | null | null | null | null | null | null | null | null | null | 120 g of 3,4-dihydroxybenzoic acid methyl ester was subjected to reaction with 340 ml of methanol and 340 ml of hydrazine hydrate over 3 days at room temperature. Then 340 ml of water was added thereto and the solvent was evaporated in vacuum. Addition of water and evaporation were repeated twice. Subsequently the prod... | NNC(=O)c1ccc(O)c(O)c1 | null | null | null |
195,908 | ord_dataset-a58d1baeeea441fb9918c10f18f2cdb9 | null | 1989-01-01T00:09:00 | true | C([NH:4][C:5]1[C:18]([F:19])=[CH:17][C:8]([CH:9]([OH:16])[CH2:10][NH:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[C:7]([F:20])[CH:6]=1)(=O)C.[OH-].[Na+]>CCO>[NH2:4][C:5]1[C:18]([F:19])=[CH:17][C:8]([CH:9]([OH:16])[CH2:10][NH:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[C:7]([F:20])[CH:6]=1 | CC(=O)Nc1cc(F)c(C(O)CNC(C)(C)C)cc1F | null | null | [Na+] | [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 | A stirred mixture consisting of 3.6 g of 4-acetamido-α-[(tert-butylamino)methyl]-2,5-difluorobenzyl alcohol, 36 mL of EtOH and 36 mL of 10% aqueous NaOH is heated at reflux under N2 for 4 h. The EtOH is evaporated in vacuo and the residue is extracted with 4×60 mL of CH2Cl2. The combined organic extracts are washed wit... | CC(C)(C)NCC(O)c1cc(F)c(N)cc1F | null | 90 | null |
736,270 | ord_dataset-76dd1b78ee414d2da0ed30700ef026f7 | null | 2006-01-01T00:10:00 | true | CC(C)(OC([NH:7][C@H:8]([CH2:21][C:22]1[CH:27]=[C:26]([F:28])[C:25]([F:29])=[CH:24][C:23]=1[F:30])[CH2:9][C:10]([N:12]1[CH2:17][CH2:16][N:15]2[CH:18]=[CH:19][N:20]=[C:14]2[CH2:13]1)=[O:11])=O)C.[ClH:32]>CO>[ClH:32].[ClH:32].[NH2:7][C@H:8]([CH2:21][C:22]1[CH:27]=[C:26]([F:28])[C:25]([F:29])=[CH:24][C:23]=1[F:30])[CH2:9][... | CC(C)(C)OC(=O)N[C@@H](CC(=O)N1CCn2ccnc2C1)Cc1cc(F)c(F)cc1F | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from 7-[(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoyl]-5,6,7,8-tetrahydroimidazo[1,2-α]pyrazine (38 mg, 0.075 mmol, from Step A), in 1.5 mL of methanol saturated with hydrogen chloride, using a procedure analogous to that described in Example 1, Step D. Eva... | N[C@@H](CC(=O)N1CCn2ccnc2C1)Cc1cc(F)c(F)cc1F | null | null | null |
1,616,469 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [NH2:1][C:2]1[C:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[C:9]=2[Cl:15])=[C:5]([OH:16])[NH:4][N:3]=1.[C:17]1(=O)[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19](=[O:26])[O:18]1>C(O)(=O)C>[Cl:15][C:9]1[C:10]([Cl:14])=[CH:11][CH:12]=[CH:13][C:8]=1[CH2:7][C:6]1[C:5]([OH:16])=[N:4][NH:3][C:2]=1[N:1]1[C:17... | Nc1n[nH]c(O)c1Cc1cccc(Cl)c1Cl | O=C1OC(=O)c2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 3-amino-4-(2,3-dichlorobenzyl)-1H-pyrazol-5-ol (18 g, 70 mmol) and isobenzofuran-1,3-dione (20 g, 140 mmol) in acetic acid (100 mL), was stirred under reflux for 16 h. The reaction mixture was cooled and filtered to provide the titled compound (13 g, 50%); LC/MS: MS (ES+) m/e 388 (MH+); 1H NMR (300 MHz, DM... | O=C1c2ccccc2C(=O)N1c1[nH]nc(O)c1Cc1cccc(Cl)c1Cl | null | 47.8 | null |
1,725,599 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | [OH:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][C:5]([N+:10]([O-:12])=[O:11])=[CH:4][C:3]=1[CH2:13][OH:14].CCOC(C)=O.CCCCCC>CCOC(C)=O.O=[Mn]=O>[OH:1][C:2]1[C:3]([CH:13]=[O:14])=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[CH:6][C:7]=1[CH:8]=[O:9] | O=[N+]([O-])c1cc(CO)c(O)c(CO)c1 | null | null | O=[Mn]=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCCCC | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | A mixture of (2-hydroxy-5-nitro-1,3-phenylene)dimethanol (0.50 mmol) and MnO2 (3.5 mmol) was dissolved in 2 ml EtOAc and the reaction was refluxed for 24 hours while being monitored by TLC (using EtOAc/Hexane 30:70 as eluent). The reaction mixture, once completed, was concentrated by evaporation under reduced pressure.... | O=Cc1cc([N+](=O)[O-])cc(C=O)c1O | null | 40 | null |
743,190 | ord_dataset-437aa6654d5044ddaef3346dc4c6e08a | null | 2006-01-01T00:11:00 | true | [N:1]1[S:5][N:4]=[C:3]2[CH:6]=[C:7]([C:10](O)=[O:11])[CH:8]=[CH:9][C:2]=12.C(N(CC)CC)C.C(OC(Cl)=O)C(C)C.[BH4-].[Na+]>O1CCCC1>[N:1]1[S:5][N:4]=[C:3]2[CH:6]=[C:7]([CH2:10][OH:11])[CH:8]=[CH:9][C:2]=12 | O=C(O)c1ccc2nsnc2c1 | null | null | CC(C)COC(=O)Cl | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 0 | 0.5 | Benzo[1,2,5]thiadiazole-5-carboxylic acid (2.00 g, 11.11 mmol) was dissolved in tetrahydrofuran (50 mL) and cooled to 0° C. To this was added triethylamine (1.80 mL, 12.87 mmol) followed by isobutylchloroformate (1.62 mL, 12.40 mmol) in a dropwise manner. The resulting slurry was stirred for a further 30 minutes at 0° ... | OCc1ccc2nsnc2c1 | null | null | null |
613,658 | ord_dataset-5c4ee54447b84205a10f9c0473172972 | null | 2003-01-01T00:10:00 | true | [CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]([OH:15])[CH:9]=1.N1C=CC=CC=1.[C:22](OC(=O)C)(=[O:24])[CH3:23]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:22]([O:15][CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])=[CH:9]1)(=[O:24])[CH3:23] | Cc1ccccc1C1=CC(O)CCCC1 | CC(=O)OC(C)=O | null | CN(C)c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | c1ccncc1 | null | null | null | null | null | null | null | null | null | 25 | 24 | To a solution of the compound obtained in Step B (6.2 g/0.03 mol) in 100 ml of CH2Cl2 there are added, in succession, pyridine (4.9 ml/0.06 mol), DMAP (1.83 g/0.015 mol), and then, dropwise, acetic anhydride (5.7 ml/0.06 mol). The whole is then stirred at room temperature for 24 hours. The reaction mixture is then conc... | CC(=O)OC1C=C(c2ccccc2C)CCCC1 | null | null | null |
498,948 | ord_dataset-18e9ed24dbd44e98b33bdc22aa7580a8 | null | 2001-01-01T00:04:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)([CH2:13][CH2:14][OH:15])[CH2:9]1)=[O:7].C(N(CC)C(C)C)(C)C.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([O:27][CH... | CS(=O)(=O)Cl | COc1cc(C(=O)N2CCC(CCO)(c3ccncc3)C2)cc(OC)c1OC | 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 | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 1 | Combine 1-(3,4,5-trimethoxybenzoyl)-3-(pyrid-4-yl)-3-(2-hydroxyethyl)pyrrolidine (0.32 g, 0.83 mmol) and N,N-diisopropylethylamine (0.46 mL, 2.64 mmol) in dichloromethane (50 mL). Cool in an ice bath. Add dropwise methanesulfonyl chloride (0.096 mL, 1.24 mmol). After 1 hour, warm to ambient temperature. Again cool in a... | COc1cc(C(=O)N2CCC(CCOS(C)(=O)=O)(c3ccncc3)C2)cc(OC)c1OC | null | null | null |
116,949 | ord_dataset-3708161f4ba04e959b9a7a8d59fd86e1 | null | 1984-01-01T00:05:00 | true | [OH:1][C@@H:2]1[CH2:6][CH:5]=[CH:4][C@H:3]1[NH2:7].C(N(CC)CC)C.C[O:16][C:17]([C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21](Cl)=[O:22])=O>O1CCCC1>[OH:1][C@@H:2]1[CH2:6][CH:5]=[CH:4][C@H:3]1[N:7]1[C:17](=[O:16])[C:19]2=[CH:27][CH:26]=[CH:25][CH:24]=[C:20]2[C:21]1=[O:22] | COC(=O)c1ccccc1C(=O)Cl | N[C@@H]1C=CC[C@H]1O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | A quantity of dl-trans-4-hydroxy-3-amino-cyclopentene is dissolved in 450 ml of tetrahydrofuran and 87 ml. (0.60 M) of triethylamine. The solution is cooled to 0° and treated dropwise with 59.6 g. (0.3 M) of o-methoxycarbonylbenzoylchloride over 50 min. The reaction is then allowed to warm to 25°. After 66 hours the re... | O=C1c2ccccc2C(=O)N1[C@@H]1C=CC[C@H]1O | null | null | null |
1,229,860 | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | null | 2012-01-01T00:11:00 | true | Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:9][C:10]([CH:13]([C:21]3[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][CH:22]=3)[CH2:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:11][CH:12]=2)=[N:6][CH:7]=1.[CH2:31]([Sn](CCCC)(CCCC)C=C)[CH2:32]CC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC... | C=C[Sn](CCCC)(CCCC)CCCC | CS(=O)(=O)c1ccc(C(CC2CCOCC2)c2ccc(-c3ccc(Br)cn3)[nH]2)cc1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | 110 | 8 | To a solution of 5-bromo-2-(5-{1-[4-(methylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridine (1.50 g) in toluene (20 mL) were added tributyl(vinyl)tin (900 μL) and tetrakistriphenylphosphinepalladium(0) (315 mg), and the mixture was stirred under argon atmosphere at 110° C. overnight. After co... | C=Cc1ccc(-c2ccc(C(CC3CCOCC3)c3ccc(S(C)(=O)=O)cc3)[nH]2)nc1 | null | 71 | null |
783,233 | ord_dataset-8034115bd2ec4d3e95bd3ff7cfde0bde | null | 2007-01-01T00:07:00 | true | [CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][C:10]([C:16]#[N:17])=[C:9]2Cl)=[O:5])[CH3:2].[CH:19]1(B(O)O)[CH2:21][CH2:20]1.C(=O)([O-])[O-].[Na+].[Na+]>>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][C:10]([C:16]#[N:17])=[C:9]2[CH:19]1[CH2:21][CH2:20]1)=[O:... | CCOC(=O)c1ccc2ncc(C#N)c(Cl)c2c1 | OB(O)C1CC1 | null | O=C([O-])[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 | Similar procedure as described in example 46d was used, starting from 4-chloro-3-cyano-quinoline-6-carboxylic acid ethyl ester (example 46c), cyclopropylboronic acid, sodium carbonate and POPd to give 3-cyano-4-cyclopropyl-quinoline-6-carboxylic acid ethyl ester as colorless oil. LC-MS m/e 267 (MH+). | CCOC(=O)c1ccc2ncc(C#N)c(C3CC3)c2c1 | null | null | null |
581,047 | ord_dataset-60f3171f0342452f8814e7f294e2be8b | null | 2003-01-01T00:02:00 | true | Cl[C:2]1[C:3]([N+:21]([O-:23])=[O:22])=[CH:4][C:5]([N+:18]([O-:20])=[O:19])=[C:6]([CH:17]=1)[C:7]([NH:9][CH2:10][CH2:11][N:12]1[CH:16]=[CH:15][N:14]=[CH:13]1)=[O:8].[NH:24]1[CH2:26][CH2:25]1>C1COCC1>[N:24]1([C:2]2[C:3]([N+:21]([O-:23])=[O:22])=[CH:4][C:5]([N+:18]([O-:20])=[O:19])=[C:6]([CH:17]=2)[C:7]([NH:9][CH2:10][CH... | C1CN1 | O=C(NCCn1ccnc1)c1cc(Cl)c([N+](=O)[O-])cc1[N+](=O)[O-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 4 | A stirred suspension of the above benzamide (150 mg, 0.44 mmol) in THF (40 mL) was treated with aziridine (91 μL, 1.76 mmol) at room temperature for 4 h, then additional aziridine (91 μL) was added. After a further 4 h, the mixture was concentrated under reduced pressure below 25° C., and the residue was partitioned be... | O=C(NCCn1ccnc1)c1cc(N2CC2)c([N+](=O)[O-])cc1[N+](=O)[O-] | null | 36.8 | null |
1,509,508 | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | null | 2014-01-01T00:11:00 | true | C([N:4]1[CH2:11][CH:10]2[C:6]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)([NH:7][O:8][CH2:9]2)[CH2:5]1)C=C.Cl>C(Cl)(Cl)Cl.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:12]1([C:6]23[CH2:5][NH:4][CH2:... | C=CCN1CC2CONC2(c2ccccc2)C1 | null | null | [Pd] | Cl | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | 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 | 18 | 5-Allyl-6a-phenyl-3,3a,4,6-tetrahydro-1H-pyrrolo[3,4-c]isoxazole (3.89 g, 16.89 mmol) is dissolved in chloroform (168 mL) and the solution is degassed with dry nitrogen for 10 minutes. N,N-Dimethylbarbituric acid (13.19 g, 84.45 mmol) is added to the solution and the solution is degassed with nitrogen for another 5 min... | c1ccc(C23CNCC2CON3)cc1 | null | 99.9 | null |
546,411 | ord_dataset-d31180f42ced44719fd9e72685c798bf | null | 2002-01-01T00:05:00 | true | [CH2:1]=[C:2]([CH3:4])[CH3:3].[C:5]([C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][C:10]([C:18]([OH:20])=[O:19])([CH2:11]3)[CH2:9]1)[CH2:15]2)([OH:7])=[O:6]>>[C:2]([O:19][C:18]([C:10]12[CH2:16][CH:14]3[CH2:13][CH:12]([CH2:17][C:8]([C:5]([O:7][C:2]([CH3:4])([CH3:3])[CH3:1])=[O:6])([CH2:15]3)[CH2:9]1)[CH2:11]2)=[O:20])(... | O=C(O)C12CC3CC(C1)CC(C(=O)O)(C3)C2 | C=C(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In accordance with a conventional method in which isobutene is used under acidic conditions, 10 mmol of 1,3-dicarboxyadamantane was t-butoxylated to give 1,3-di(t-butoxycarbonyl)adamantane. | CC(C)(C)OC(=O)C12CC3CC(C1)CC(C(=O)OC(C)(C)C)(C3)C2 | null | null | null |
333,098 | ord_dataset-ba1248d90e3e465693710bbc45866f37 | null | 1996-01-01T00:07:00 | true | [CH3:1][N:2]1[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.Cl.[C-:10]#[N:11].[K+]>O>[OH:8][C:5]1([C:10]#[N:11])[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1 | [C-]#N | CN1CCC(=O)CC1 | null | Cl | [K+] | 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 | 10 | 2 | To freshly distilled 1-methylpiperidin-4-one (81.72 g, 0.72 mole) in water (200 cc), were added about 100 cc HCl 37% to pH 3. The reaction mixture was cooled in an ice bath and potassium cyanide (49 g, 0.75 mole) in water (200 cc) was added at an adequate rate in order to maintain an internal temperature of about 10° C... | CN1CCC(O)(C#N)CC1 | null | 67 | null |
1,671,262 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [C:1]([C:4]1[C:5]2[N:6]([CH:41]=[N:42][N:43]=2)[C:7]([CH2:32][C:33]2[C:38]([Cl:39])=[CH:37][CH:36]=[CH:35][C:34]=2[Cl:40])=[N:8][C:9]=1[NH:10][C:11]1[C:16]([F:17])=[CH:15][C:14]([N:18]2[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]2)=[C:13]([F:31])[CH:12]=1)(=[O:3])[NH2:2].FC(F)(F)C(O)=O>ClCCl>[Cl:39][C:38]1[CH... | CC(C)(C)OC(=O)N1CCN(c2cc(F)c(Nc3nc(Cc4c(Cl)cccc4Cl)n4cnnc4c3C(N)=O)cc2F)CC1 | 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 | 4 | To a solution of the product of Example 15G (230 mg, 0.36 mmol) in dichloromethane (8 mL) was added trifluoroacetic acid (2 mL) dropwise. The mixture was stirred at ambient temperature for 4 hours and concentrated. The solid was washed with ethanol and dried under vacuum to give the title compound. 1H NMR (DMSO-d6, 300... | NC(=O)c1c(Nc2cc(F)c(N3CCNCC3)cc2F)nc(Cc2c(Cl)cccc2Cl)n2cnnc12 | null | null | null |
243,602 | ord_dataset-fa3b512e2d924b9b965301ebcba6853d | null | 1992-01-01T00:03:00 | true | [C:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[C:14]([OH:16])=O)=[CH:11][CH:10]=[CH:9][CH:8]=2)(=[O:3])[CH3:2].[Cl:17][C:18]1[CH:19]=[C:20]([NH:24][C:25](=[O:28])[NH:26][NH2:27])[CH:21]=[CH:22][CH:23]=1>>[Cl:17][C:18]1[CH:19]=[C:20]([NH:24][C:25](=[O:28])[NH:26][N:27]=[C:14]([C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:... | CC(=O)c1cnc2ccccc2c1C(=O)O | NNC(=O)Nc1cccc(Cl)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 | In the same manner, 3-acetyl-4-quinolinecarboxylic acid is reacted with 4-(3-chlorophenyl)semicarbazide to give 3-acetyl-4-quinolinecarboxylic acid 4-(3-chlorophenyl)semicarbazone, m.p. 229° (compound 104). | CC(=O)c1cnc2ccccc2c1C(O)=NNC(=O)Nc1cccc(Cl)c1 | null | null | null |
1,304,014 | ord_dataset-78c3f723155a4347a902b53bcee1524d | null | 2013-01-01T00:06:00 | true | Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:5]=[C:4]([N:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[C:22]([O:23][CH3:24])[C:17]=3[N:16]=[C:15]2[CH:25]([F:27])[F:26])[N:3]=1.[NH:28]1[CH2:31][CH:30]([NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])[CH2:29]1>>[F:26][CH:25]([F:27])[C:15]1[N:14]... | COc1cccc2c1nc(C(F)F)n2-c1nc(Cl)nc(N2CCOCC2)n1 | CC(C)(C)OC(=O)NC1CNC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Reaction of 1-[4-chloro-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-(difluoromethyl)-4-methoxy-1H-benzimidazole and tert-butyl 3-azetidinylcarbamate gave tert-butyl 1-[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-3-azetidinylcarbamate in 90% yield: mp (CH2Cl2/hexanes) 217-220°... | COc1cccc2c1nc(C(F)F)n2-c1nc(N2CCOCC2)nc(N2CC(NC(=O)OC(C)(C)C)C2)n1 | null | 90 | null |
1,661,513 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [ClH:1].C(OC(=O)[NH:8][C:9]1[N:10]=[C:11]2[N:15]([CH:16]=1)[CH:14]=[C:13]([Br:17])[S:12]2)(C)(C)C>O1CCOCC1>[ClH:1].[Br:17][C:13]1[S:12][C:11]2=[N:10][C:9]([NH2:8])=[CH:16][N:15]2[CH:14]=1 | CC(C)(C)OC(=O)Nc1cn2cc(Br)sc2n1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 25 | 4 | To a solution of 4M HCl in dioxane (2 mL) was added compound 10 (0.13 mmol). The reaction mixture was stirred at room temperature for 4 hrs. The mixture was concentrated under vacuum and the solid was dried in vacuo to give compound 11 as a white solid in quantitative yield. 1H NMR (CDCl3, 400 MHz) δ (ppm) 5.26 (s, 2H)... | Nc1cn2cc(Br)sc2n1 | null | null | null |
428,141 | ord_dataset-8cce6f317d644b348a7978a2dce3ea01 | null | 1999-01-01T00:03:00 | true | C([C:3]12[CH:8]([C:9]([OH:11])=[O:10])[CH:7]1[CH2:6][CH2:5][C:4]2=[O:12])C.[OH-].[Na+]>>[O:12]=[C:4]1[CH2:5][CH2:6][CH:7]2[CH:3]1[CH:8]2[C:9]([OH:11])=[O:10] | CCC12C(=O)CCC1C2C(=O)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 | null | null | (+)-2-Aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid may be prepared by reacting carbethoxymethyl dimethylsulfonium bromide with 2-cyclopenten-1-one in the presence of a base, such as 1,8-diazabicyclo[5.4.0]undec-7-ene to afford ethyl 2-oxobicyclo[3.1.0]hexane-6-carboxylate. This ester may then be reacted with an aque... | O=C(O)C1C2CCC(=O)C21 | null | null | null |
977,735 | ord_dataset-f886e51ba1484c76a94bce1482f1eab9 | null | 2010-01-01T00:07:00 | true | [CH2:1]([C:3]1[NH:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)=[N:5][C:4]=1[C:15]([O:17]CC)=[O:16])[CH3:2].[OH-].[Na+].C(O)C>O1CCCC1>[CH2:1]([C:3]1[NH:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)=[N:5][C:4]=1[C:15]([OH:17])=[O:16])[CH3:2] | CCOC(=O)c1nc(-c2ccc(F)cc2)[nH]c1CC | null | null | [Na+] | [OH-] | 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 | 25 | 8 | A mixture of ethyl 5-ethyl-2-(4-fluorophenyl)imidazol-4-carboxylate (2.81 g), 4N aqueous sodium hydroxide solution (14 ml), ethanol (35 ml) and tetrahydrofuran (15 ml) was stirred at room temperature overnight, followed by refluxing for 3 hours. 4N aqueous sodium hydroxide solution (28 ml) was added to the mixture and ... | CCc1[nH]c(-c2ccc(F)cc2)nc1C(=O)O | null | 42.2 | null |
1,380,777 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | [CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[N:10]=[CH:9][NH:8][C:7]2=O)[CH3:2].O=P(Cl)(Cl)[Cl:19]>C1(C)C=CC=CC=1>[Cl:19][C:7]1[C:6]2[C:11](=[CH:12][C:13]([O:14][CH3:15])=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=2)[N:10]=[CH:9][N:8]=1 | CCOc1cc2c(=O)[nH]cnc2cc1OC | O=P(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | 125 | null | According to the procedure described in Example 6A Step 5, a mixture of 6-ethoxy-7-methoxyquinazolin-4(3H)-one (0.52 g, 2.36 mmol) and POCl3 (1 mL) in toluene (10 mL) was heated at 125° C. for 3.5 hours. The residue was purified by silica gel chromatography with 0-25% EtOAc/hexane as eluants to afford 4-chloro-6-ethoxy... | CCOc1cc2c(Cl)ncnc2cc1OC | null | 34 | null |
1,556,705 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[O:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19].[CH:23]([C:26]1[CH:30]=[C:29]([NH:31][C:32](=O)[O:33]C2C=CC=CC=2)[N:28]([C:41]2[CH:42]=[N:43][CH:44]=[CH:45][CH:46]=2)[N:27]=1)([CH3:25])[CH3:24]>C1COCC1.CN(C1C=CN=C... | COc1cc2ncnc(Oc3cccc(N)c3)c2cc1OC | CC(C)c1cc(NC(=O)Oc2ccccc2)n(-c2cccnc2)n1 | null | CN(C)c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | Using the procedure described in Example 306B, to a solution of 3-(6,7-dimethoxyquinazolin-4-yloxy)aniline (91 mg, 0.3 mmol), prepared as described in Example 113A, in THF (2 ml) was added DMAP (20 mg, 0.16 mmol) and phenyl 3-isopropyl-1-(pyridin-3-yl)-1H-pyrazol-5-ylcarbamate (110 mg, 0.34 mmol), described in the prev... | COc1cc2ncnc(Oc3cccc(NC(=O)Nc4cc(C(C)C)nn4-c4cccnc4)c3)c2cc1OC | null | 57.7 | null |
618,316 | ord_dataset-2952e63264f5422a84e12cca1e0541ee | null | 2003-01-01T00:12:00 | true | [Si:1]([O:8][C@H:9]([C:43]1[CH:44]=[N:45][CH:46]=[CH:47][CH:48]=1)[CH2:10][N:11]([CH2:19][C@@H:20]1[CH2:29][CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[C:25]([C:30]3[CH:31]=[CH:32][C:33]4[C:38](=[O:39])[O:37][C:36](C)(C)[O:35][C:34]=4[CH:42]=3)[CH:26]=2)[O:21]1)[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])([C:4]([... | CC(C)(C)OC(=O)N(C[C@@H]1CCc2cc(-c3ccc4c(c3)OC(C)(C)OC4=O)ccc2O1)C[C@H](O[Si](C)(C)C(C)(C)C)c1cccnc1 | null | null | O=C([O-])[O-] | [K+] | 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 | 18 | To a solution of the compound of Example 179 in methanol (10 mL) was added potassium carbonate (0.12 g) at room temperature. The reaction mixture was allowed to stir at room temperature for 18 hours and then concentrated under reduced pressure. The resulting residue was washed with distilled water (10 mL) and extracted... | COC(=O)c1ccc(-c2ccc3c(c2)CC[C@@H](CN(C[C@H](O[Si](C)(C)C(C)(C)C)c2cccnc2)C(=O)OC(C)(C)C)O3)cc1O | null | 94 | null |
817,086 | ord_dataset-50f99930fc41474db226bc80774b38df | null | 2008-01-01T00:04:00 | true | CS([C:5]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)[S:7][N:6]=1)(=O)=O.[CH2:17]([OH:21])[C:18]#[C:19][CH3:20].[H-].[Na+].[Cl-].[Na+]>CN(C)C=O>[F:16][C:12]1[CH:11]=[C:10]([C:8]2[S:7][N:6]=[C:5]([O:21][CH2:17][C:18]#[C:19][CH3:20])[N:9]=2)[CH:15]=[CH:14][CH:13]=1 | CC#CCO | CS(=O)(=O)c1nsc(-c2cccc(F)c2)n1 | null | [Cl-] | [H-] | [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 | null | 0.17 | In 3 ml of N,N-dimethylformamide, 350 mg of 3-methylsulfonyl-5-(3-fluorophenyl)-1,2,4-thiadiazole and 105 mg of 2-butyne-1-ol were dissolved, to the resulting solution was added 65 mg of sodium hydride (60% oily) with ice-cooling, and the mixture was stirred for 10 minutes, and further stirred at room temperature for 4... | CC#CCOc1nsc(-c2cccc(F)c2)n1 | null | 85.9 | null |
1,432,094 | ord_dataset-5e6956e6e8c24a168866a253f4a66c6c | null | 2014-01-01T00:05:00 | true | Cl.[CH2:2]([O:9][C:10]1[CH:11]=[C:12]([C:26]2[O:27][C:28]([CH3:31])=[CH:29][N:30]=2)[CH:13]=[C:14]([O:17]COCC[Si](C)(C)C)[C:15]=1[Br:16])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C1COCC1.O>[CH2:2]([O:9][C:10]1[C:15]([Br:16])=[C:14]([OH:17])[CH:13]=[C:12]([C:26]2[O:27][C:28]([CH3:31])=[CH:29][N:30]=2)[CH:11]=1)[C:3]1[CH:... | Cc1cnc(-c2cc(OCOCC[Si](C)(C)C)c(Br)c(OCc3ccccc3)c2)o1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | O | null | null | null | null | null | null | null | null | null | 25 | 3 | Concentrated hydrochloric acid (3 mL) was added to a solution of 2-(3-(benzyloxy)-4-bromo-5-((2-(trimethylsilyl)ethoxy)methoxy)phenyl)-5-methyloxazole (0.60 g, 1.22 mmol) in THF (8 mL) and stirred at room temperature for three hours. The solution was diluted with water and extracted with 1:1 ethyl acetate/diethyl ether... | Cc1cnc(-c2cc(O)c(Br)c(OCc3ccccc3)c2)o1 | null | null | null |
1,412,773 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | [Cl:1][C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:14][CH3:15])[CH:8]=2)[N:3]=1.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[Mg]Br.O>C1COCC1>[Cl:1][C:2]1[C:11]([CH:12]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[O:17][CH3:16])[OH:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:... | COc1ccccc1[Mg]Br | COc1ccc2nc(Cl)c(C=O)cc2c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1CCOC1 | null | null | null | null | null | null | null | null | null | -78 | null | 2-Chloro-6-methoxyquinoline-3-carbaldehyde (2.66 g, 12 mmol) was dissolved in THF (40 mL) under nitrogen and cooled to −78° C. At this temperature, a solution of 2-methoxyphenyl magnesium bromide (1M, 12.1 mL, 13.32 mmol) in THF was added by drops. Then the mixture was heated slowly to room temperature. The batch was m... | COc1ccc2nc(Cl)c(C(O)c3ccccc3OC)cc2c1 | null | null | null |
1,305,979 | ord_dataset-78c3f723155a4347a902b53bcee1524d | null | 2013-01-01T00:06:00 | true | [F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=O)[CH3:10].[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1>CCCCCC.[Ti](Cl)(Cl)(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)=[CH2:10] | CC(=O)c1ccc(F)cc1F | C1CCNC1 | null | Cl[Ti](Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCCCC | null | null | null | null | null | null | null | null | null | null | 25 | 24 | To a solution of 1-(2,4-difluorophenyl)ethanone (10.0 g, 64.0 mmol) and pyrrolidine (32.1 mL, 384 mmol) in hexane (150 mL) was added titanium tetrachloride (3.86 mL, 35.2 mmol) dropwise at 0° C. over 15 minutes. The reaction mixture was stirred at room temperature for 24 hours and filtered. The filtrate was evaporated ... | C=C(c1ccc(F)cc1F)N1CCCC1 | null | 36.6 | null |
937,667 | ord_dataset-90b0aa1f83334a02919b2be3a1c04542 | null | 2010-01-01T00:02:00 | true | [CH3:1][C:2]1[C:3]([O:20][CH3:21])=[C:4]([C:8]([CH3:19])([CH3:18])[CH2:9][C:10]([OH:17])([C:13]([F:16])([F:15])[F:14])[CH:11]=O)[CH:5]=[CH:6][CH:7]=1.[NH2:22][C:23]1[CH:32]=[CH:31][CH:30]=[C:29]2[C:24]=1[CH:25]=[N:26][N:27]([CH3:34])[C:28]2=[O:33]>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[CH3:21][O:20][C:3]1[C:2]([CH3:1])=[CH:7][CH:6]... | COc1c(C)cccc1C(C)(C)CC(O)(C=O)C(F)(F)F | Cn1ncc2c(N)cccc2c1=O | null | Cl[Ti](Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | null | Analogously to Example 10, the corresponding imine is produced starting from 600 mg of 4-(3-methyl-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal and 316 mg of 5-amino-2-methylphthalazin-1-one. As in Example 3, 460 mg of the imine is reacted by reaction with 5.2 ml of titanium tetrachloride (1 M in dic... | COc1c(C)ccc2c1C(C)(C)CC(O)(C(F)(F)F)C2Nc1cccc2c(=O)n(C)ncc12 | null | 4.3 | null |
294,916 | ord_dataset-bb4579c57ddc48c6a01fad97dacb6293 | null | 1994-01-01T00:08:00 | true | [BH4-].[Na+].[CH3:3][O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([O:15][CH3:16])=[CH:7][C:6]=1[CH:17]=[CH2:18].[OH2:19]>COCCOC.[Ti](Cl)(Cl)(Cl)Cl>[CH3:3][O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([O:15][CH3:16])=[CH:7][C:6]=1[CH2:17][CH2:18][OH:19] | O | C=Cc1cc(OC)c2ccccc2c1OC | null | Cl[Ti](Cl)(Cl)Cl | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COCCOC | null | null | null | null | null | null | null | null | null | null | 25 | 1 | 1.61 g of titanium tetrachloride were added to a mixture of 0.65 g of sodium borohydride and 20 ml of dry ethylene glycol dimethyl ether, and the resulting mixture was stirred at room temperature for 1 hour. A solution of 1.83 g of 1,4-dimethoxy-2-vinylnaphthalene [prepared as described in step (b) above] in 40 ml of d... | COc1cc(CCO)c(OC)c2ccccc12 | null | null | null |
1,218,639 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | [CH2:1]([C:6]1([CH:12]=[CH2:13])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].C12CCCC(CCC1)B12[H]B2(C3CCCC2CCC3)[H]1.[OH:34]O.[OH-].[Na+]>C1COCC1.O>[CH2:1]([C:6]1([CH2:12][CH2:13][OH:34])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1)[CH2:2][CH2:3][CH2:4][CH3:5] | C=CC1(CCCCC)CCCCC1 | OO | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 2.5 | A solution of 2-5 (90 mg, 0.50 mmol) in THF (3.4 mL) was added to a solution of 9-BBN dimer (206 mg, 0.84 mmol) in THF (3 mL). The reaction was placed in a 60° C. oil bath and after 2.5 h, a solution of H2O2 (35%, 1.4 mL)/NaOH (0.5 M, 1.4 mL)/H2O (0.35 mL) was added. The reaction was heated to reflux for 1 h and then a... | CCCCCC1(CCO)CCCCC1 | null | 71 | null |
1,166,872 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | C1(C[NH:8][C:9]2[C:14]3[CH2:15][O:16][CH2:17][C:18]4[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[C:19]=4[C:13]=3[CH:12]=[CH:11][C:10]=2[O:30][CH3:31])C=CC=CC=1>[Pd].C(OCC)(=O)C>[CH3:31][O:30][C:10]1[CH:11]=[CH:12][C:13]2[C:19]3[C:20]([O:28][CH3:29])=[C:21]([O:26][CH3:27])[C:22]([O:24][CH3... | COc1ccc2c(c1NCc1ccccc1)COCc1cc(OC)c(OC)c(OC)c1-2 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | The N-phenylmethyl-3,9,10,11-tetramethoxy-5,7-dihydrodibenzo[c,e]oxepin-4-amine (45.3 mg) and palladium on charcoal (10% w/w; 2.3 mg) in ethyl acetate (3 mL) in a steel autoclave was stirred under hydrogen (2 bar) for 2.5 hours. The mixture was then passed through a plug of alumina and concentrated in vacuo to afford a... | COc1ccc2c(c1N)COCc1cc(OC)c(OC)c(OC)c1-2 | null | 24.1 | null |
1,614,015 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | Br[C:2]1[CH:3]=[CH:4][C:5]2[O:14][CH2:13][CH2:12][N:11]3[C:7](=[N:8][C:9]([C:15]4[N:16]([CH:21]([CH3:23])[CH3:22])[N:17]=[C:18]([CH3:20])[N:19]=4)=[CH:10]3)[C:6]=2[CH:24]=1.[CH3:25][N:26]1[CH2:31][CH2:30][CH:29]([CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][NH:33]2)[CH2:28][CH2:27]1.CC(C)([O-])C.[Na+]>O1CCOCC1.CC(C)([P](C(C... | Cc1nc(-c2cn3c(n2)-c2cc(Br)ccc2OCC3)n(C(C)C)n1 | CN1CCC(C2CCCCN2)CC1 | null | CC(C)(C)[P]([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)(C(C)(C)C)C(C)(C)C | CC(C)(C)[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 100 | null | A mixture of 9-bromo-2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene from Example 6 (200 mg, 0.51 mmol), l′-methyl-[2,4]bipiperidinyl (234 mg, 1.28 mmol), sodium tertbutoxide (148 mg, 1.5 mmol) and Pd(P(tBu)3)2 (13 mg, 0.026 mmol) in dioxane was degassed with a stream of argo... | Cc1nc(-c2cn3c(n2)-c2ccc(N4CCCCC4C4CCN(C)CC4)cc2OCC3)n(C(C)C)n1 | null | 12 | null |
1,146,776 | ord_dataset-68715347640045adb1b09e6a04722b0e | null | 2012-01-01T00:03:00 | true | Cl[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8]CC)=[O:7])=[CH:4][N:3]=1.[O:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[CH2:19][OH:20]>>[O:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[CH2:19][O:20][C:2]1[CH:12]=[CH:11][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1 | CCOC(=O)c1ccc(Cl)nc1 | OCC1CCCCO1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 1.5 | The title compound was synthesized as described for Intermediate example I-92 in 34% yield starting from ethyl 6-chloronicotinate and tetrahydro-2H-pyran-2-ylmethanol, the final reaction mixture was stirred for 1.5 h; 1H NMR (400 MHz, DMSO-d6) δ ppm 8.69 (d, 1 H), 8.13 (dd, 1 H), 6.91 (d, 1 H), 4.26 (d, 2 H), 3.87 (d, ... | O=C(O)c1ccc(OCC2CCCCO2)nc1 | null | 34 | null |
670,464 | ord_dataset-e90cd41afe844e49875435eb99903799 | null | 2005-01-01T00:05:00 | true | [ClH:1].[OH:2][NH:3][C:4]([C:6]1([S:15]([C:18]2[CH:23]=[CH:22][C:21]([S:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH2:11][CH2:10][N:9]([CH2:12][C:13]#[CH:14])[CH2:8][CH2:7]1)=[O:5].C([O-])([O-])=O.[K+].[K+].C(Br)C=C>CN(C=O)C>[ClH:1].[OH:2][NH:3][C:4]([C:6]1([S:15]([C:18]2[CH:... | C#CCN1CCC(C(=O)NO)(S(=O)(=O)c2ccc(Sc3ccccc3)cc2)CC1 | null | 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 | C=CCBr | null | null | null | null | null | null | null | null | null | 25 | 5 | Part A: To a solution of the amine hydrochloride salt of Example 9, part E (4.78 g, 10.8 mmol) in DMF (25 mL) were added K2CO3 (2.98 g, 21.6 mmol) and allyl bromide (0.935 mL, 10.8 mmol), and the solution was stirred for 5 hours at ambient temperature. The solution was partitioned between ethyl acetate and H2O, and the... | C=CCN1CCC(C(=O)NO)(S(=O)(=O)c2ccc(Sc3ccccc3)cc2)CC1 | null | null | null |
99,308 | ord_dataset-b37811c5ed724c3b844cc4d2b5640398 | null | 1982-01-01T00:09:00 | true | [CH3:1][CH:2]([CH2:17]S(C1C=CC=CC=1)(=O)=O)[CH2:3][CH:4]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:5]1=O.CC(C)([O-])C.[K+]>>[CH3:17][CH:2]1[CH2:3][C:4]2[C:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]=2)=[CH:1]1 | CC(CC1CCCCCCCCCCC1=O)CS(=O)(=O)c1ccccc1 | null | null | CC(C)(C)[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 0.756 g (2 mmole) of 2-(2-methyl-3-phenylsulfonyl-prop-1-yl)-cyclododecanone and 0.672 g (6 mmole) of potassium tert-butoxide were progressively heated to 160° under 0.02 Torr and the formed title compound directly distilled from the reaction mixture. There were thus isolated 0.216 g (50% yield) of the desired compound... | CC1C=C2CCCCCCCCCC=C2C1 | null | null | null |
108,788 | ord_dataset-d9235b0d1f9f4e85b2690ee8f860dc30 | null | 1983-01-01T00:09:00 | true | [C:1]([CH2:9][CH2:10][C:11]([OH:13])=O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:15][NH2:16]>C(O)C>[C:2]1([C:1]2[CH2:9][CH2:10][C:11](=[O:13])[NH:15][N:16]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1 | NN | O=C(O)CCC(=O)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | null | null | A mixture of 3-benzoylpropionic acid (89 g), 80% hydrazine hydrate (25.5 ml) in ethanol (1000 ml) is refluxed for 6 hrs, cooled and filtered to give 75.6 g of 6-phenyl-4,5-dihydro-3(2H)-pyridazinone. Bromine (70 g) is added dropwise to a solution of the above pyridazinone in acetic acid (200 ml) at 80° C. After the add... | O=C1CCC(c2ccccc2)=NN1 | null | null | null |
718,804 | ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | null | 2006-01-01T00:07:00 | true | Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[OH:23][C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[NH:29][C:28]([CH3:33])=[CH:27]2.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6... | Cc1cc2cc(O)ccc2[nH]1 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1 | 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 | O | null | null | null | null | null | null | null | null | null | 100 | 2 | A suspension of 4-chloro-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline (0.13 g, 0.4 mmol), 5-hydroxy-2-methylindole (74 mg, 0.5 mmol) and potassium carbonate (83 mg, 0.6 mmol) in DMF (1.5 ml) was stirred at 100° C. for 2 hours. After cooling to ambient temperature, water (20 ml) was added. The precipitate was col... | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCCN1CCCC1 | null | 46.2 | null |
70,602 | ord_dataset-06d4002fc4d34860a0688cba690e12dc | null | 1980-01-01T00:09:00 | true | [CH2:1]([O:4][C:5]1[CH:12]=[C:11]([CH3:13])[C:8]([CH:9]=O)=[C:7]([CH3:14])[C:6]=1[CH3:15])[CH:2]=[CH2:3]>CC(C)=O>[CH2:1]([O:4][C:5]1[CH:12]=[C:11]([CH3:13])[C:8]([CH:9]=[CH:3][CH2:2][CH:1]=[O:4])=[C:7]([CH3:14])[C:6]=1[CH3:15])[CH:2]=[CH2:3] | C=CCOc1cc(C)c(C=O)c(C)c1C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | The 5-(4-allyloxy-2,3,6-trimethyl-phenyl)-3-methyl-penta-2,4-diene-1-triphenylphosphonium bromide employed as the starting material can be prepared by the procedure of Example 3. This procedure is carried out by alkylation of 1,3,5-trimethylphenol with allyl bromide to give 1,3,5-trimethyl-phenyl allyl ether (boiling p... | C=CCOc1cc(C)c(C=CCC=O)c(C)c1C | null | null | null |
1,372,849 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][C:30]=1[F:31])[CH2:26]Br>>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19]... | CC(C)(C)OC(=O)N1CCC[C@@H]1COc1ccc(O)cc1 | Fc1ccc(CBr)cc1F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Followed the same procedure as that of step 2 in Example 91 with the use of (R)-2-(4-hydroxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (150 mg, 0.5 mmol) and 3,4-difluoro-benzyl bromide (145 mg, 0.6 mmol) to afford the title product, (120 mg, 55% yield); LCMS; 100% APCI+, Calcd: 419.5; Found m/z: 42... | CC(C)(C)OC(=O)N1CCC[C@@H]1COc1ccc(OCc2ccc(F)c(F)c2)cc1 | null | 57.2 | null |
1,044,869 | ord_dataset-dd320ded4b3f4764af39de99491533f7 | null | 2011-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:28]([F:31])([F:30])[F:29])=[C:6]([CH:27]=1)[CH2:7][N:8]1[CH2:13][CH2:12][NH:11][C:10]2[N:14]=[CH:15][C:16]([C:18]3[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=3)[C:21](O)=[O:22])=[CH:17][C:9]1=2.[F:32][C:33]([F:47])([F:46])[C:34]1[CH:35]=[C:36]([CH:39]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:... | O=C(O)c1cccc(-c2cnc3c(c2)N(Cc2cc(Cl)ccc2C(F)(F)F)CCN3)c1 | NCc1cc(C(F)(F)F)cc(C(F)(F)F)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 | 3-{1-[5-chloro-2-(trifluoromethyl)benzyl]-1,2,3,4-tetrahydropyrido[2,3-b]pyrazin-7-yl}benzoic acid was reacted with 3,5-bis(trifluoromethyl)benzylamine as in General Procedure 10 to give the title compound. LCMS: m/z=672.88 (M+H+); retention time=1.11 minutes. | O=C(NCc1cc(C(F)(F)F)cc(C(F)(F)F)c1)c1cccc(-c2cnc3c(c2)N(Cc2cc(Cl)ccc2C(F)(F)F)CCN3)c1 | null | null | null |
1,512,193 | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | null | 2014-01-01T00:11:00 | true | [C:1]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:6]=[CH:5][C:4]([C:7]2[C:27]([Cl:28])=[CH:26][C:10]3[N:11]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:12](S(C)(=O)=O)=[N:13][C:9]=3[CH:8]=2)=[CH:3][CH:2]=1.[OH:35][CH:36]1[CH2:40][CH2:39][CH:38]([C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH2... | C[Si](C)(C)CCOCn1c(S(C)(=O)=O)nc2cc(-c3ccc(-c4ccccc4)cc3)c(Cl)cc21 | CCOC(=O)C1CCC(O)C1 | null | null | null | 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 | 80 | null | To a solution of 5-(biphenyl-4-yl)-6-chloro-2-(methylsulfonyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazole (Intermediate 3, 0.350 g, 0.682 mmol) and ethyl 3-hydroxycyclopentanecarboxylate (Intermediate 9, 0.647 mL, 4.09 mmol) in 2.3 mL DMF was added DSU (0.514 mL. 3.41 mmol) dropwise via syringe. The reaction... | CCOC(=O)C1CCC(Oc2nc3cc(-c4ccc(-c5ccccc5)cc4)c(Cl)cc3n2COCC[Si](C)(C)C)C1 | null | null | null |
1,352,694 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | N#N.[CH3:3][CH:4]1[CH2:8][CH2:7][CH:6]([CH3:9])[NH:5]1.Br[CH2:11][CH2:12][CH2:13][C:14]#[N:15].C([O-])([O-])=O.[K+].[K+]>CC#N>[CH3:3][CH:4]1[CH2:8][CH2:7][CH:6]([CH3:9])[N:5]1[CH2:11][CH2:12][CH2:13][CH2:14][NH2:15] | CC1CCC(C)N1 | N#CCCCBr | null | N#N | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | 25 | 15 | In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to a solution of 2,5-dimethylpyrrolidine (250 mg, 2.34 mmol) and 4-bromobutyronitrile (0.24 mL, 2.34 mmol) in dry CH3CN (12 mL) was added K2CO3 (1.78 g, 12.89 mmol) at rt followed by KI (39 mg, 0.23 mmol). The react... | CC1CCC(C)N1CCCCN | null | null | null |
1,574,906 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | [CH3:1][P:2]1(=[O:8])[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.F[C:10]1[CH:11]=[CH:12][C:13]([N+:18]([O-:20])=[O:19])=[C:14]([O:16][CH3:17])[CH:15]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:17][O:16][C:14]1[CH:15]=[C:10]([N:5]2[CH2:6][CH2:7][P:2](=[O:8])([CH3:1])[CH2:3][CH2:4]2)[CH:11]=[CH:12][C:13]=1[N+:18]([O-:20])=[O:19] | CP1(=O)CCNCC1 | COc1cc(F)ccc1[N+](=O)[O-] | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 50 | 2 | A mixture of 4-methyl-[1,4]azaphosphinane-4-oxide (133 mg, 1.00 mmol), 5-fluoro-2-nitroanisole (340 mg, 2.00 mmol), K2CO3 (345 mg, 2.50 mmol), and DMF (5 mL) was heated to 50° C. After 2 h, the reaction mixture was concentrated and purified by silica gel chromatography (0-5% 7N ammonia in methanol:dichloromethane) to a... | COc1cc(N2CCP(C)(=O)CC2)ccc1[N+](=O)[O-] | null | 95.7 | null |
1,767,388 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([CH3:13])=[N:10][C:9]=2[C:14]([N:16]2[CH2:21][CH2:20][CH2:19][C@@H:18]([CH3:22])[C@H:17]2[CH2:23][N:24]2C(=O)C3C(=CC=CC=3)C2=O)=[O:15])=[CH:4][CH:3]=1.O.NN>CO>[NH2:24][CH2:23][C@@H:17]1[C@H:18]([CH3:22])[CH2:19][CH2:20][CH2:21][N:16]1[C:14]([C:9]1[N:10]=[C:11]([CH3:13])[... | Cc1nc(C(=O)N2CCC[C@@H](C)[C@H]2CN2C(=O)c3ccccc3C2=O)c(-c2ccc(F)cc2)s1 | null | null | NN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | O | null | null | null | null | null | null | null | null | null | null | null | A mixture of 2-(((2S,3R)-1-(5-(4-fluorophenyl)-2-methylthiazole-4-carbonyl)-3-methylpiperidin-2-yl)methyl)isoindoline-1,3-dione (130 mg, 272 μmol) and hydrazine hydrate (67 μL, 1.36 mmol) in MeOH (3 mL) was heated at reflux for 2 h. The mixture was cooled and the solvent was removed in vacuo. The crude was dissolved in... | Cc1nc(C(=O)N2CCC[C@@H](C)[C@H]2CN)c(-c2ccc(F)cc2)s1 | null | null | null |
344,772 | ord_dataset-d0003732f14e4648a00d341275654590 | null | 1996-01-01T00:11:00 | true | [CH3:1]/[C:2](/[CH2:6][CH2:7]/[CH:8]=[C:9](\[CH3:21])/[CH2:10][CH2:11]/[CH:12]=[C:13](\[CH3:20])/[CH2:14][CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18])=[CH:3]\[CH2:4][OH:5]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1]/[C:2](/[CH2:6][CH2:7]/[CH:8]=[C:9](\[CH3:21])/[CH2:10][CH2:11]/[CH:12]=[C:13](\[CH3:20])/[CH2:14][CH2:15][CH:16]=[C:1... | CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CO | null | null | [Mn+4] | [O-2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | 16 | To a solution of (E,E,E)-3,7,11,15 tetramethyl-2,6,10,14-hexadecatetraen-1-ol (320 mg, 1.1 mmol) in dry methylene chloride (10 ml) at room temperature was added manganese dioxide (957 mg, 0.011 mol) and the resulting mixture stirred for 16 hours. The solids were removed by filtration through a pad of celite washing wit... | CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/C=O | null | null | null |
48,418 | ord_dataset-b43eb0158fd54801957aaa07bbdf3057 | null | 1978-01-01T00:11:00 | true | Br[CH:2]([C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[CH:9][CH:8]=1)[C:3]([O:5][CH3:6])=[O:4].[CH3:21][C:22]1([C:28]2[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>>[CH3:6][O:5][C:3](=[O:4])[CH:2]([O:34][C:31]1[CH:32]=[CH:33][C:28]... | CC1(c2ccc(O)cc2)CCCCC1 | COC(=O)C(Br)c1ccc(Oc2ccc(Cl)cc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In a manner similar to Example 16, 7.11 g of methyl α-bromo-α-[p-(p-chlorophenoxy)phenyl]acetate is reacted with 4.75 g of p-(1-methylcyclohexyl)phenol for 4 hrs. Chilling and filtering gives 7.4 g of product, mp 110°-112° C. Recrystallization from methanol-chloroform gives 6.3 g of white crystals, mp 111°-112.5° C. | COC(=O)C(Oc1ccc(C2(C)CCCCC2)cc1)c1ccc(Oc2ccc(Cl)cc2)cc1 | null | 79.6 | null |
1,210,247 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[N:6][CH:7]=1.[CH2:15]([O:17][C:18]([C:20]1([CH2:35]I)[CH2:24][CH2:23][N:22]([C:25](=[O:34])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[O:32][CH3:33])[CH2:21]1)=[O:19])[CH3:16]>>[CH2:15]([O:17][C:18]([C:20]1([CH2:35][O:14][C:11]2[CH:... | CCOC(=O)C1(CI)CCN(C(=O)c2ccccc2OC)C1 | Oc1ccc(-c2ccc(Cl)cn2)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 was prepared according to the method described for Preparation 29 using 4-(5-chloro-pyridin-2-yl)-phenol (Preparation 17) and 3-iodomethyl-1-(2-methoxy-benzoyl)-pyrrolidine-3-carboxylic acid ethyl ester (Preparation 15) to afford the racemate as a white solid (133 mg, 54.7%) | CCOC(=O)C1(COc2ccc(-c3ccc(Cl)cn3)cc2)CCN(C(=O)c2ccccc2OC)C1 | null | null | null |
394,758 | ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | null | 1998-01-01T00:03:00 | true | [C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)=[C:19]([O:28][CH2:29][CH2:30][O:31][C:32]3[CH:37]=[CH:36][C:35]([C:38]#[N:39])=[CH:34][CH:33]=3)[N:18]=[CH:17][N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C([Sn]([N:53]=[N+:54]=[N-... | CCCC[Sn](CCCC)(CCCC)N=[N+]=[N-] | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(C#N)cc2)cc1 | null | [F-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | 25 | 0.33 | A mixture of 4-tert-butyl-N-{6-[2-(4-cyanophenoxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzensulfonamide (1.31 g), tributyltin azide (1.60 g) and toluene (13 ml) is refluxed under argon atmosphere for 24 hours. After cooling, ethyl acetate and 10% aqueous potassium fluoride solution are added to the reaction soluti... | Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ccc(-c3nnn[nH]3)cc2)cc1 | null | 89.1 | null |
277,242 | ord_dataset-ad17798fcea64e26ba91604fca520090 | null | 1993-01-01T00:10:00 | true | [CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH2:27][CH:26]([CH3:31])[CH2:25][CH:24]([O:32][CH3:33])[CH:23]2[O:34][C:19]([OH:38])([CH:20]([CH3:37])[CH2:21][CH:22]2[O:35][CH3:36])[C:18](=[O:39])[C:17](=[O:40])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:41])[O:9][CH:8]([C:42]([CH3:52])=[CH:43][CH:44]2[CH2:49][... | C=C(CC)OC(=N)C(Cl)(Cl)Cl | CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O)C(O)C3)C(C)C(O)CC1=O)C(C)CC2OC | null | O=S(=O)(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 25 | null | To a solution of 17-ethyl-1,14-dihydroxy-12-[2'-(3",4"-dihydroxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone (150 mg in 3 ml 33% methylene chloride in cyclohexane), sec-butenyl trichloroacetimidate (62 μl neat) was added and... | C=C(CC)OC1CC(C=C(C)C2OC(=O)C3CCCCN3C(=O)C(=O)C3(O)OC(C(OC)CC(C)CC(C)=CC(CC)C(=O)CC(O)C2C)C(OC)CC3C)CCC1O | null | null | null |
1,353,924 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | C(O)(=[O:3])C.[CH3:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][CH2:24][O:25][P:26]1([O:32][CH2:31][C@H:30]([CH2:33][N:34]2[C:39](=[O:40])[N:38]=[C:37]([NH2:41])[CH:36]=[CH:35]2)[O:29][CH2:28]1)=[O:27]>[OH-].[Na+]>[CH3:5][CH... | CCCCCCCCCCCCCCCCOCCCOP1(=O)CO[C@@H](Cn2ccc(N)nc2=O)CO1 | CC(=O)O | 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 | 1.5 | As described in U.S. Pat. No. 6,716,825, in Step 1 of the scheme above, cidofovir was suspended in N,N-DMF and N,N′-dicyclohexyl-4-morpholine-carboxamide was added. The mixture was stirred overnight to dissolve the cidofovir. The clear solution was then charged to an addition funnel and slowly added (30 min) to a stirr... | CCCCCCCCCCCCCCCCOCCCOP(=O)(O)CO[C@H](CO)Cn1ccc(N)nc1=O | null | null | null |
1,130,661 | ord_dataset-285df12e34cd46e993e3c8ebc3a8962a | null | 2012-01-01T00:01:00 | true | C[O:2][C:3](=[O:38])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][CH:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]3[N:22]([C:29]4[C:34]([Cl:35])=[CH:33][CH:32]=[CH:31][C:30]=4[Cl:36])[N:23]=[N:24][C:25]=3[CH:26]([CH3:28])[CH3:27])=[CH:15][C:14]=2[CH3:37])[CH3:12])[CH:5]=1.[OH-].[Li+]>O1CCOCC1>[Cl:36][C:30]1[CH:31]=[CH... | COC(=O)c1cccc(SC(C)c2ccc(OCc3c(C(C)C)nnn3-c3c(Cl)cccc3Cl)cc2C)c1 | null | null | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 50 | null | To an ambient temperature solution of 3-(1-{4-[3-(2,6-dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy]-2-methyl-phenyl}-ethylsulfanyl)-benzoic acid methyl ester (53 mg, 0.0934 mmol) in dioxane (2 mL) is added a solution of lithium hydroxide (140 μL, 0.280 mmol, 2.0N in water). The reaction is heated to 50° C... | Cc1cc(OCc2c(C(C)C)nnn2-c2c(Cl)cccc2Cl)ccc1C(C)Sc1cccc(C(=O)O)c1 | null | 94.3 | null |
1,573,398 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | [C:1]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[CH:5][C:4]([C:7]2[NH:11][C:10]3[CH:12]=[CH:13][CH:14]=[C:15]([C:16](O)=[O:17])[C:9]=3[N:8]=2)=[CH:3][CH:2]=1.C[N:26]1CCOCC1.ClC(OCC(C)C)=O>C1COCC1>[C:1]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[CH:5][C:4]([C:7]2[NH:11][C:10]3[CH:12]=[CH:13][CH... | CN1CCOCC1 | O=C(O)c1cccc2[nH]c(-c3ccc(-c4ccccc4)cc3)nc12 | null | CC(C)COC(=O)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 | -50 | 2 | To the solution of 2-biphenyl-4-yl-1H-benzoimidazole-4-carboxylic acid (0.35 g, 1.1 mmol) in THF (20 mL) was added N-methyl morpholine (0.2 mL, 1.6 mmol) and the mixture was cooled to −50° C. Isobutyl chloroformate (0.22 mL, 1.6 mmol) was then added drop wise, the reaction mixture was warmed to −10° C. and stirred for ... | NC(=O)c1cccc2[nH]c(-c3ccc(-c4ccccc4)cc3)nc12 | null | 69.6 | null |
1,584,413 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | FC(F)(F)C(O)=O.[Br:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2(O)[CH2:18][CH:17]([C:19]([O:21][CH3:22])=[O:20])[CH2:16]2)=[CH:11][CH:10]=1.[SiH](CC)(CC)CC>>[Br:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]2[CH2:16][CH:17]([C:19]([O:21][CH3:22])=[O:20])[CH2:18]2)=[CH:13][CH:14]=1 | COC(=O)C1CC(O)(c2ccc(Br)cc2)C1 | null | null | CC[SiH](CC)CC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | 17.5 | null | Into a 20-L 4-necked round-bottom flask was placed trifluoroacetic acid (12 L), methyl 3-(4-bromophenyl)-3-hydroxycyclobutane-1-carboxylate (2330 g, 8.17 mol, 1.00 equiv), followed by the addition of Et3SiH (3556 g, 30.58 mol, 5.00 equiv) dropwise with stirring at 10-25° C. The resulting solution was stirred at room te... | COC(=O)C1CC(c2ccc(Br)cc2)C1 | null | 98.9 | null |
971,713 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | [CH2:1]([O:3][C:4](=[O:20])/[CH:5]=[C:6](/[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]([F:19])([F:18])[F:17])[CH:10]=1)\[CH3:7])[CH3:2].[Br:21]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.O>C(Cl)(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:20])/[CH:5]=[C:6](/[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]([F:... | O=C1CCC(=O)N1Br | CCOC(=O)/C=C(\C)Oc1cccc(OC(F)(F)F)c1 | null | O=C(OOC(=O)c1ccccc1)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)(Cl)Cl | O | null | null | null | null | null | null | null | null | null | null | null | To a stirred mixture of (E)-3-(3-trifluoromethoxy-phenoxy)-but-2-enoic acid ethyl ester (9.87 g, 0.034 mol) in carbon tetrachloride (60 mL) under a nitrogen atmosphere was added N-bromosuccinimide (9.08 g, 0.051 mol) and benzoyl peroxide in water (75%, 1.09 g, 0.003 mol). Nitrogen gas was bubbled through the mixture fo... | CCOC(=O)/C=C(\CBr)Oc1cccc(OC(F)(F)F)c1 | null | 29.5 | null |
1,024,662 | ord_dataset-136cfada6ce247b4919085a57363459e | null | 2011-01-01T00:01:00 | true | [CH:1]1([N:7]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[C:8]([NH:10][C:11]2[S:12][C:13]([CH:16]=O)=[CH:14][N:15]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(=O)C.[NH:28]1[CH2:33][CH2:32][S:31][CH2:30][CH2:29]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[CH:1]1([N:7]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][C... | C1CSCCN1 | O=Cc1cnc(NC(=O)N(C2CCCCC2)C2CCCCC2)s1 | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | Prepared as described in general procedure (P) using 1,1-dicyclohexyl-3-(5-formyl-thiazol-2-yl)-urea (60 mg. 0.18 mmol), acetic acid (11 μL, 0.18 mmol), thiomorpholine (21 μL, 0.22 mmol) and sodium triacetoxyborohydride (38 mg, 0.20 mmol) to afford 7 mg (9%) of the desired product after purification. | O=C(Nc1ncc(CN2CCSCC2)s1)N(C1CCCCC1)C1CCCCC1 | null | 9.2 | null |
1,532,133 | ord_dataset-8d5c200bca27407ab9febe7598e16458 | null | 2015-01-01T00:01:00 | true | [CH3:1][C:2]([C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[C:8]([N+:13]([O-])=O)[CH:7]=1)([CH3:5])[CH2:3][CH3:4].O.[Cl-].[Ca+2].[Cl-]>CCO.[Fe]>[CH3:5][C:2]([C:6]1[CH:7]=[C:8]([NH2:13])[C:9]([NH2:10])=[CH:11][CH:12]=1)([CH3:1])[CH2:3][CH3:4] | CCC(C)(C)c1ccc(N)c([N+](=O)[O-])c1 | null | null | [Fe] | [Ca+2] | [Cl-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCO | null | null | null | null | null | null | null | null | null | null | null | To a stirred solution of 4-(1,1-dimethylpropyl)-2-nitroaniline (Preparation 94, 11 g, 0.052 mol) in EtOH:water (240 mL:60 mL) was added iron powder (14.8 g, 0.254 mol) and calcium chloride (11.7 g, 0.105 mol). The reaction was heated to reflux for 6 hours before cooling and concentrating in vacuo. The residue was extra... | CCC(C)(C)c1ccc(N)c(N)c1 | null | 66.9 | null |
865,958 | ord_dataset-b8b98725045d45bdbd73512048f4b47e | null | 2009-01-01T00:02:00 | true | Br[C:2]1[C:3]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:17])=[CH:11][CH:10]=2)=[N:4][N:5]([CH2:7][CH3:8])[CH:6]=1.[C:25]1([S:31]([N:34]2[C:38]3=[N:39][CH:40]=[CH:41][C:42](B4OC(C)(C)C(C)(C)O4)=[C:37]3[CH:36]=[C:35]2[CH:52]=[O:53])(=[O:33])=[O:32])[CH:30]=[CH:29]... | CC1(C)OB(c2ccnc3c2cc(C=O)n3S(=O)(=O)c2ccccc2)OC1(C)C | CCn1cc(Br)c(-c2ccc(NC(=O)Nc3ccccc3)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 | Following the procedure described in Intermediate 100 with N-[4-(4-bromo-1-ethyl-1H-pyrazol-3-yl)phenyl]-N′-phenylurea and 1-(phenylsulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde provided the title compound. ESMS [M+H]+: 591.4 | CCn1cc(-c2ccnc3c2cc(C=O)n3S(=O)(=O)c2ccccc2)c(-c2ccc(NC(=O)Nc3ccccc3)cc2)n1 | null | null | null |
1,260,332 | ord_dataset-266f60b4555945d6afb2d2bdf5fa04e0 | null | 2013-01-01T00:02:00 | true | [I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[NH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].F[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1.O>CN(C=O)C>[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[N:4]([C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)[N:3... | Nc1ncnc2[nH]nc(I)c12 | O=[N+]([O-])c1ccc(F)cc1 | 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 | 100 | 24 | To a solution of 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (1) (5.22 g, 20 mmol) in DMF (60 mL) were added K2CO3 (8.3 g, 60 mmol) and 1-fluoro-4-nitrobenzene (2.96 g, 21 mmol). After the resulting mixture was stirred at 100° C. for 24 hr under N2 atmosphere, the reaction mixture was cooled to RT before pouring into wa... | Nc1ncnc2c1c(I)nn2-c1ccc([N+](=O)[O-])cc1 | null | 89 | null |
311,118 | ord_dataset-04982f13ed08448d93df6794846500f3 | null | 1995-01-01T00:06:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([NH2:14])=[O:13])=[C:6]2[O:15][CH:16]([CH3:18])[CH3:17].[H-].[Na+].[CH3:21][O:22][CH2:23]Cl>CN(C)C=O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:21][O:22][CH3:23])[C:7]([C:12]([NH2:14])=[O:13])=[C:6]2[O:15][CH:16... | COCCl | COc1ccc2[nH]c(C(N)=O)c(OC(C)C)c2c1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 25 | 8 | 5-Methoxy-3-(1-methylethoxy)-1H-indole-2-carboxamide (106 mg, 0.43 mmol) in 4 mL of dimethylformamide is added to a suspension of sodium hydride (60% by weight) (30 mg, 0.75 mol) in 2 mL of dimethylformamide. After 1 hour chloromethyl methyl ether (60 μL, 0.79 mmol) is added, and the solution is stirred at room tempera... | COCn1c(C(N)=O)c(OC(C)C)c2cc(OC)ccc21 | null | 31.8 | null |
1,481,273 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13](=[O:38])[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[NH:27][C:28]([C@@H:30]1[CH2:34][CH2:33][CH2:32][N:31]1C([O-])=O)=[O:29])=O)(C)(C)C.Cl.O1CCOCC1>>[C:16]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[NH:27][C:28]([... | CC(C)(C)OC(=O)N1CCC[C@H]1C(=O)Nc1ccccc1-c1ccccc1NC(=O)[C@@H]1CCCN1C(=O)[O-] | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 25 | 4 | (2S,2′S)-tert-butyl-2,2′-(biphenyl-2,2′-diylbis(azanediyl))bis(oxomethylene)dipyrrolidine-1-carboxylate d (0.140 g, 0.24 mmol) was suspended in a solution of 4M HCl/dioxane and stirred at room temperature for 4 h until LCMS indicated complete deprotection. The reaction mixture was concentrated to give (2S,2′S)—N,N′-(bi... | O=C(Nc1ccccc1-c1ccccc1NC(=O)[C@@H]1CCCN1)[C@@H]1CCCN1 | null | null | null |
551,916 | ord_dataset-ec9decb576c4424c9685993f6262bd9c | null | 2002-01-01T00:07:00 | true | [Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:4](Cl)[N:3]=1.[NH2:17][CH2:18][C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1>C(N(CC)CC)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:4]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][N... | Clc1nc(Cl)c2ncn(C3CCCC3)c2n1 | NCc1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | null | 2-Chloro-6-[(4-pyridyl)methylamino]-9-cyclopentylpurine is prepared from 2,6-dichloro-9-cyclopentylpurine, 4-aminomethylpyridine, and triethylamine essentially as described above in Example 1, Scheme A, step b. | Clc1nc(NCc2ccncc2)c2ncn(C3CCCC3)c2n1 | null | null | null |
407,367 | ord_dataset-d5bb2294ac964841b8ffc9e0a34e93af | null | 1998-01-01T00:07:00 | true | [CH2:1]([N:8]([CH2:34][CH2:35][CH2:36][CH2:37][C:38]1[CH:39]=[N:40][CH:41]=[CH:42][CH:43]=1)[CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([N:20]3[C:24](=[O:25])[NH:23][N:22]=[N:21]3)[CH:18]=2)[NH:13][C:12]=1[C:26]1[CH:31]=[C:30]([CH3:32])[CH:29]=[C:28]([CH3:33])[CH:27]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH... | Cc1cc(C)cc(-c2[nH]c3ccc(-n4nn[nH]c4=O)cc3c2CCN(CCCCc2cccnc2)Cc2ccccc2)c1 | O=C([O-])[O-] | null | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CI | ClCCl | null | null | null | null | null | null | null | null | null | null | 2 | To a solution of 1-[3-{2-[benzyl-(4-pyridin-3-yl-butyl)-amino]ethyl}-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-1,4-dihydrotetrazol-5-one (25 mg in 1.5 mL dry N,N-dimethylformamide) at 0° C. was added 13 mg potassium carbonate followed by 0.033 mL of a 10% solution of iodomethane in methylene cloride, and the mixture stirre... | Cc1cc(C)cc(-c2[nH]c3ccc(-n4nnn(C)c4=O)cc3c2CCN(CCCCc2cccnc2)Cc2ccccc2)c1 | null | 78.1 | null |
67,101 | ord_dataset-b5f1497361c94e5fa55257200189a6a4 | null | 1980-01-01T00:06:00 | true | [I:1]/[CH:2]=[CH:3]/[C:4](=[O:15])[C:5]([CH3:14])([CH3:13])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[BH4-].[Na+]>CO>[I:1]/[CH:2]=[CH:3]/[CH:4]([OH:15])[C:5]([CH3:13])([CH3:14])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1 | CC(C)(Cc1ccccc1)C(=O)/C=C/I | 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 | 0 | null | An ice-cold solution of 7.5 g. of 1-iodo-4,4-dimethyl-5-phenyl-trans-1-penten-3-one in 150 ml. of methanol was treated with 0.89 g. of sodium borohydride and stirred at 0° for 11/2 hours. The solvent was evaporated and the residue was dissolved in water and then extracted with ether. The ether was dried and evaporated ... | CC(C)(Cc1ccccc1)C(O)/C=C/I | null | null | null |
247,336 | ord_dataset-75ca79f43dad4cc8a934fe6487fa8eb1 | null | 1992-01-01T00:05:00 | true | [OH:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:15])[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=1[OH:8].[C:22](Cl)(=[O:40])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]>O1CCOCC1>[C:... | CCCCCCCCCCCCCCCCCC(=O)Cl | O=C(C=Cc1cc(O)c(O)c([N+](=O)[O-])c1)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 90 | null | A solution containing 2.0 g of the product obtained in Example 8 and 10.0 g of stearoyl chloride in 10 ml of dioxane was stirred and heated for 18 h at 90° C. After cooling petroleum ether was added and the product was filtered. Recrystallization from dichloromethane-petroleum ether yielded 0.64 g (17%) of the desired ... | CCCCCCCCCCCCCCCCCC(=O)Oc1cc(C=CC(=O)c2ccccc2)cc([N+](=O)[O-])c1O | null | 16.5 | null |
1,747,105 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | [C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH:13]([CH3:15])[CH3:14])[C:6]([OH:8])=O)#[N:2].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.O[NH:31][C:32]([C:34]1[CH:35]=[CH:36][C:37]2[O:41][CH:40]=[CH:39][C:38]=2[CH:42]=1)=[NH:33]>CN(C=O)C.C([O-])(O)=O.[Na+]>[O:41]1[C:37]2[CH:36]=[CH:35][C:34]([C:32]3[N:31]=[C:6]([C:5]4[CH:9]... | CC(C)Oc1ccc(C(=O)O)cc1C#N | N=C(NO)c1ccc2occc2c1 | null | O=C([O-])O | On1nnc2ccccc21 | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | ClCCCl | null | null | null | null | null | null | null | null | null | 25 | 0.5 | Prepared using General Procedure 2. A flask containing 3-cyano-4-isopropoxybenzoic acid (147.7 mg, 0.72 mmol), HOBt (143 mg, 0.94 mmol) and EDC (180 mg, 0.94 mmol) in DMF (2.0 mL) was stirred for 0.5 h at room temperature under an atmosphere of N2. A solution of N-hydroxybenzofuran-5-carboximidamide INT-68 (218 mg, 0.7... | CC(C)Oc1ccc(-c2nc(-c3ccc4occc4c3)no2)cc1C#N | null | 44 | null |
875,537 | ord_dataset-e1c3af9b105b4af09a5171403bbfc06f | null | 2009-01-01T00:04:00 | true | Cl[C:2]1[N:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([NH:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])[CH:3]=1.[OH:21][CH2:22][C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1.C([O-])([O-])=O.[Na+].[Na+]>C(#N)C.O.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(... | OCc1cccc(B(O)O)c1 | COc1nc(Cl)cc(NCCc2ccc(Cl)cc2Cl)n1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | O | null | null | null | null | null | null | null | null | null | null | 0.42 | In a hard walled glass tube, a solution of (6-chloro-2-methoxy-pyrimidin-4-yl)-[2-(2,4-dichloro-phenyl)-ethyl]-amine (250 mg, 0.75 mmol), 3-(hydroxymethyl)phenylboronic acid (137 mg, 0.9 mmol) and Na2CO3 (79.7 mg, 0.75 mmol) in acetonitrile/water (6 mL, 2:1) is degassed over nitrogen for 10 minutes. Tetrakis(triphenylp... | COc1nc(NCCc2ccc(Cl)cc2Cl)cc(-c2cccc(CO)c2)n1 | null | 54.4 | null |
1,743,941 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | [C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[N:11]=[C:12]([N:19]3[CH2:24][CH2:23][CH2:22][C@@H:21]([NH:25][C:26](=[O:36])[C:27]4[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH3:35])=[CH:29][CH:28]=4)[CH2:20]3)[N:13]=[N:14][C:15]=2[C:16]([NH2:18])=[O:17])=[CH:5][CH:4]=1)#[N:2].Cl.[CH3:38][OH:39]>>[C:16]([C:15]1[N:14]=[N:13][C:1... | CO | CCOc1ccc(C(=O)N[C@@H]2CCCN(c3nnc(C(N)=O)c(Nc4ccc(C#N)cc4)n3)C2)cc1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 25 | 8 | (R)-5-(4-Cyanophenylamino)-3-(3-(4-ethoxybenzamido)piperidin-1-yl)-1,2,4-triazine-6-carboxamide (194) (90 mg, 0.18 mmol) was dissolved in 25 mL dry MeOH. It was chilled in an ice bath, and was then charged with HCl gas from a lecture bottle using a long needle to bubble the gas into the bottom of the solution until sat... | CCOc1ccc(C(=O)N[C@@H]2CCCN(c3nnc(C(N)=O)c(Nc4ccc(C(=N)OC)cc4)n3)C2)cc1 | null | null | null |
904,963 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | [CH:1]([C:4]1[C:12]([CH:13]=O)=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][N:6]2[N:5]=1)([CH3:3])[CH3:2].Cl.[NH2:16][NH:17][C:18]([NH2:20])=[O:19].C(N(CC)CC)C>CO>[CH:1]([C:4]1[C:12](/[CH:13]=[N:16]/[NH:17][C:18]([NH2:20])=[O:19])=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][N:6]2[N:5]=1)([CH3:2])[CH3:3] | NNC(N)=O | CC(C)c1nn2ccccc2c1C=O | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CO | null | null | null | null | null | null | null | null | null | null | null | A mixture of 2-isopropylpyrazolo[1,5-a]pyridine-3-carbaldehyde (0.5 g, 1 equivalent), semicarbazide hydrochloride (0.35 g, 1.2 equivalents), and triethylamine (0.4 mL, 1.1 equivalent) in 5 mL of methanol was reflux for 30 minutes. The solution was concentrated and the crude solids produced were extracted with THF, and ... | CC(C)c1nn2ccccc2c1/C=N/NC(N)=O | null | 70.6 | null |
1,171,498 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | [CH3:1][NH:2][C:3]([C:5]1[N:6]=[C:7]([CH2:26][CH3:27])[N:8]2[CH2:13][CH2:12][NH:11][CH:10]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)[C:9]=12)=[O:4].[CH3:28][NH:29][C:30]([C@@H:32](OS(C1C=CC(C)=CC=1)(=O)=O)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:31]>>[CH3:1][... | CNC(=O)[C@@H](OS(=O)(=O)c1ccc(C)cc1)c1ccccc1 | CCc1nc(C(=O)NC)c2n1CCNC2CCc1ccc(C(F)(F)F)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared by reaction of 3-ethyl-8-[2-(4-trifluoromethyl-phenyl)-ethyl]-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid methylamide (22 mg; 0.057 mmol) with toluene-4-sulfonic acid (S)-methylcarbamoyl-phenyl-methyl ester. Purification by preparative HPLC afforded the mixture of 2 diastereoisomers. LC-MS: tR=... | CCc1nc(C(=O)NC)c2n1CCN(C(C(=O)NC)c1ccccc1)C2CCc1ccc(C(F)(F)F)cc1 | null | null | null |
1,391,265 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | [CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[C:15]3[CH:16]=[C:17]([CH2:21]O)[CH:18]=[C:19]([CH3:20])[C:14]=3[N:13]=[C:12]2[CH2:23][CH2:24][CH3:25])=[CH:6][C:5]=1[F:26].CCN(C(C)C)C(C)C.CS(Cl)(=O)=O.[N-:42]=[N+:43]=[N-:44].[Na+]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][... | CCCc1nc2c(C)cc(CO)cc2n1Cc1ccc(C(=O)OC)c(F)c1 | [N-]=[N+]=[N-] | null | CN(C)c1ccncc1 | CS(=O)(=O)Cl | [Na+] | 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 | 25 | 3 | Intermediate (8a) (2.4 g, 6.5 mmol) was added to 125 mL of DCM followed by DIPEA (4.6 mL, 26.1 mmol) and 4-dimethylaminopyridine (80 mg, 653 μmol). Methanesulfonyl chloride (1.0 mL, 13.1 mmol) was then added at 0° C. and the mixture was warmed to room temperature. After 3 hours, the mixture was concentrated and the mat... | CCCc1nc2c(C)cc(CN=[N+]=[N-])cc2n1Cc1ccc(C(=O)OC)c(F)c1 | null | 81.7 | null |
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