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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
255,742 | ord_dataset-30ad5cf6083a45a387b45bebad1a4d65 | null | 1992-01-01T00:10:00 | true | [CH:1]([NH2:4])([CH3:3])[CH3:2].Br[CH2:6][CH2:7][N:8]1[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[O:10][C:9]1=[O:17]>C(#N)C>[CH:1]([NH:4][CH2:6][CH2:7][N:8]1[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[O:10][C:9]1=[O:17])([CH3:3])[CH3:2] | CC(C)N | O=c1oc2cccnc2n1CCBr | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | null | null | 0.1 mol of isopropylamine and 0.01 mol of 3-(2-bromoethyl)-3H-oxazolo[4,5-b]pyridin-2-one, dissolved beforehand in 40 cm3 of acetonitrile, are introduced into a 100-cm3 ground-necked round-bottomed flask equipped with a reflux condenser. The mixture is heated to reflux for 15 hours. After cooling, the precipitate obtai... | CC(C)NCCn1c(=O)oc2cccnc21 | null | null | null |
1,382,570 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | C[O:2][C:3](=[O:13])[CH:4]=[CH:5][CH2:6][N:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[ClH:14]>>[ClH:14].[N:7]1([CH2:6][CH:5]=[CH:4][C:3]([OH:13])=[O:2])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1 | COC(=O)C=CCN1CCCCC1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 4-Piperidin-1-yl-but-2-enoic acid methyl ester (2.05 g, 11.2 mmol) and concentrated hydrochloric acid (10 mL) were combined in dioxanes (30 mL) and heated to reflux overnight. The mixture was concentrated in vacuo. The residue was crystallized from IPA to yield the desired product (390 mg, 17%). 400 MHz 1H NMR (DMSO-d6... | O=C(O)C=CCN1CCCCC1 | null | 17 | null |
148,108 | ord_dataset-0b70410902ae4139bd5d334881938f69 | null | 1986-01-01T00:09:00 | true | [N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8]2)[CH:2]=1.[Cl-].[CH2:17]([O:19][C:20](=[O:27])[CH2:21][CH2:22][CH2:23][C:24](O)=[O:25])[CH3:18].[OH-].[NH4+]>C(Cl)Cl>[O:25]=[C:24]([C:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5]... | CCOC(=O)CCCC(=O)O | c1cncc(-n2ccc3ccccc32)c1 | null | [Cl-] | [NH4+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | 8 | To a mixture of 10.0 g of N-(3-pyridyl)-indole (J. Chem. Soc. (C), 85, 1970) and 13.8 g of glutaric acid monoethyl ester chloride in 90 ml of methylene chloride is added dropwise over a period of 3 hours a solution of 20.1 g of stannic chloride in 60 ml of methylene chloride. The reaction mixture is stirred at room tem... | CCOC(=O)CCCC(=O)c1cn(-c2cccnc2)c2ccccc12 | null | null | null |
1,144,889 | ord_dataset-68715347640045adb1b09e6a04722b0e | null | 2012-01-01T00:03:00 | true | [CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.[CH:11](=O)[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1>>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][N:8]=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH:5][CH:4]=1 | COc1ccc(CN)cc1 | COc1ccc(C=O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 25 | 2 | 4-Methoxybenzylamine (40 g, 290 mmol) was cooled to 0° C., and p-anisaldehyde (39.7 g, 292 mmol) was added dropwise. The reaction was stirred at ambient temperature for two hours, concentrated under reduced pressure, and further dried under high vacuum overnight to provide 97 g of N-(4-methoxybenzyl)-N-[(4-methoxypheny... | COc1ccc(C=NCc2ccc(OC)cc2)cc1 | null | 131 | null |
1,473,974 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | Br[C:2]1[N:3]=[CH:4][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][N:17]=3)[CH2:12][CH2:11]2)=[O:9])=[N:6][CH:7]=1.[CH3:24][C@@H:25]1[CH2:29][O:28][C:27](=[O:30])[NH:26]1>>[CH3:22][C:21]1[C:16]([N:13]2[CH2:14][CH2:15][N:10]([C:8]([C:5]3[N:6]=[CH:7][C:2]([N:26]4[C@H:25]... | C[C@@H]1COC(=O)N1 | Cc1cnc(N2CCN(C(=O)c3cnc(Br)cn3)CC2)c(C)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Using (5-bromopyrazin-2-yl) [4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone (130 mg) described in Preparation Example 232 and (R)-4-methyloxazolidin-2-one (35 mg) and by the reaction and treatment in the same manner as in Example 1, the title compound (110 mg) was obtained. | Cc1cnc(N2CCN(C(=O)c3cnc(N4C(=O)OC[C@H]4C)cn3)CC2)c(C)c1 | null | 80.3 | null |
378,385 | ord_dataset-846d411edee44814931e062174d7ef12 | null | 1997-01-01T00:09:00 | true | [CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:27])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][NH2:24])=[C:17]([O:25][CH3:26])[CH:16]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].[C:28]([O:31][C:32]1[C:33](=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:34](O)=[O:35])(=[O:30])[CH3:29].ON1C2C=CC=CC=2N=N1>C(#N)C... | CC(=O)Oc1ccccc1C(=O)O | COc1cc(CC(=O)NCCCc2ccc(C)c(C)c2)ccc1OCCN | null | On1nnc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CC#N | null | null | null | null | null | null | null | null | null | null | null | 0.27 g (0.66 mmol) of N-{3-(3,4-dimethylphenyl)propyl}-4-(2-aminoethoxy)-3-methoxyphenylacetamide obtained in Step 5 of Example 3, 0.17 g (0.94 mmol) of acetylsalicylic acid and 0.10 g (0.74 mmol) of 1-hydroxylbenzotriazole were dissolved in 15 ml of a mixture of acetonitrile and dimethylformamide(1:2). 0.19 g (0.92 mm... | COc1cc(CC(=O)NCCCc2ccc(C)c(C)c2)ccc1OCCNC(=O)c1ccccc1OC(C)=O | null | 62.6 | null |
276,291 | ord_dataset-02ee2261663048188cf6d85d2cc96e3f | null | 1993-01-01T00:09:00 | true | C(OC([N:8](C(OC(C)(C)C)=O)[C:9]1[N:17]=[C:16]2[C:12]([N:13]=[CH:14][N:15]2[O:18][CH2:19][C@H:20]([O:40][CH2:41][P:42]([O:47][CH2:48][CH3:49])([O:44][CH2:45][CH3:46])=[O:43])[CH2:21][O:22][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)=[C:11]([O:50][CH3:51])[N:10]=1)=O)(C)(C)C>FC(F)(F)C(O)=O>[NH2:8][C:9]1[N:17]=[C:16]2[C:12]([N... | CCOP(=O)(CO[C@@H](COn1cnc2c(OC)nc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)nc21)CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)OCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | A solution of (S)-2-[bis-(t-butyloxycarbonyl)amino]-9-[3-(t-butyldiphenylsilyloxy)-2-(diethoxyphosphorylmethoxy)propoxy]-6-methoxypurine (300 mg, 0.36 mmol) in 67% aqueous trifluoroacetic acid (3 ml) was kept at ambient temperature for 3 hours. The solution was washed with hexane (3×10 ml) and the aqueous phase evapora... | CCOP(=O)(CO[C@H](CO)COn1cnc2c(OC)nc(N)nc21)OCC | null | 69.2 | null |
1,674,603 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [C:1]([O:5][C:6]([N:8]([CH2:14][C:15]1[CH:20]=[C:19]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:18]=[CH:17][N:16]=1)[CH2:9][CH2:10][CH2:11][CH:12]=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:26]([NH:33][CH:34]1[CH2:36][CH2:35]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[CH2:26]([N:33]([CH:34]1[CH2:35][CH2:36]1)[CH2:12... | CCOC(=O)c1ccnc(CN(CCCC=O)C(=O)OC(C)(C)C)c1 | c1ccc(CNC2CC2)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 | By General Procedure A from ethyl 2-({[(tert-butoxy)carbonyl](4-oxobutyl)amino}methyl)pyridine-4-carboxylate and N-benzylcyclopropanamine. Purification by column chromatography (5% MeOH/DCM) gave the title compound as colorless oil. 1H-NMR (300 MHz, CDCl3): δ 8.60 (d, 1H), 7.70 (s, 1H), 7.60 (d, 1H), 7.10 (m, 5H), 4.50... | CCOC(=O)c1ccnc(CN(CCCCN(Cc2ccccc2)C2CC2)C(=O)OC(C)(C)C)c1 | null | null | null |
281,592 | ord_dataset-1953a9402dda47b6bcfe3e3cb9ab8a07 | null | 1993-01-01T00:12:00 | true | [NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:12]1.Cl[CH2:23][C:24]1[O:28][C:27]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+].CN(C)C=O>O>[CH2:32]([O:31][C:29]([C:27]1[O:28][C:24]([... | CCOC(=O)c1ccc(CCl)o1 | CCOC(=O)N1CCC(Nc2nc3ccccc3[nH]2)CC1 | null | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O | null | null | null | null | null | null | null | null | null | null | null | A mixture of 28.8 parts of ethyl 4-(1H-benzimidazol-2-ylamino)-1-piperidinecarboxylate (as prepared in Example XIV of U.S. Pat. No. 4,219,559), 33.9 parts of ethyl 5-chloromethyl-2-furancarboxylate, 15.9 parts of sodium carbonate and 282 parts of N,N-dimethylformamide was stirred for 2 nights at 70° C. The reaction mix... | CCOC(=O)c1ccc(Cn2c(NC3CCN(C(=O)OCC)CC3)nc3ccccc32)o1 | null | 70.8 | null |
1,541,214 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | Br[C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][N:20]([CH:23]4[CH2:26][O:25][CH2:24]4)[CH2:19][C@H:18]3[CH3:27])=[CH:13][N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[C:28]([O:31][CH2:32][C:33]1[C:38](B2OC(C)(C)C(C)(C)O2)=[CH:37][C:36]([F:48])=[CH:35][C:34]=1[N:49]1[C:61](=[O:62])[C:60]2... | C[C@@H]1CN(C2COC2)CCN1c1ccc(Nc2cc(Br)cn(C)c2=O)nc1 | CC(=O)OCc1c(B2OC(C)(C)C(C)(C)O2)cc(F)cc1-n1ncc2c3c(sc2c1=O)CCCC3 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Following the procedure in Example 102 and starting with (R)-5-bromo-1-methyl-3-(5-(2-methyl-4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)pyridin-2(1H)-one 115f (217 mg, 0.50 mmol) and 117e (249 mg, 0.50 mmol) afforded 117f as a yellow solid (174 mg, 48%). MS: [M+H]+ 726. | CC(=O)OCc1c(-c2cc(Nc3ccc(N4CCN(C5COC5)C[C@H]4C)cn3)c(=O)n(C)c2)cc(F)cc1-n1ncc2c3c(sc2c1=O)CCCC3 | null | 47.9 | null |
664,045 | ord_dataset-5a3d853c53674888a5691dce2e398792 | null | 2005-01-01T00:03:00 | true | [CH3:1][NH:2][C@H:3]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]3[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=3)[CH:10]=2)[CH2:4]1.Cl[CH2:28][C:29]1[CH:34]=[CH:33][N:32]=[C:31]([C:35]2[CH:40]=[C:39]([O:41][CH3:42])[C:38]([O:43][CH3:44])=[C:37]([O:45][CH3:46... | CN[C@H]1CCN(Cc2ccnc(-c3cc(OC)c(OC)c(OC)c3)c2)C1 | COc1cc(-c2cc(CCl)ccn2)cc(OC)c1OC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | (3S)-3-methylamino-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]pyrrolidine (104 mg) and 4-chloromethyl-2-(3,4,5-trimethoxyphenyl)pyridine (85 mg) was condensed in the same manner as described in Example 2. Yellow syrup obtained was converted to a tetrahydrochloride by the usual method giving the title compound as... | COc1cc(-c2cc(CN3CC[C@H](N(C)Cc4ccnc(-c5cc(OC)c(OC)c(OC)c5)c4)C3)ccn2)cc(OC)c1OC | null | null | null |
919,165 | ord_dataset-8e59bd24817446f7b1c68e805b8e5f1d | null | 2009-01-01T00:11:00 | true | [S:1]1[C:5]([C:6]2[CH:11]=[CH:10][N:9]=[C:8]([NH:12][CH:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C:21]#[N:22])[CH2:15][CH2:14]3)[N:7]=2)=[CH:4][C:3]2[CH:23]=[CH:24][CH:25]=[CH:26][C:2]1=2.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:22][CH2:21][CH2:20][CH2:19][N:16]1[CH2:15][CH2:14][CH:13]([NH:12][C:8]2[N:7]=[C:6](... | N#CCCN1CCC(Nc2nccc(-c3cc4ccccc4s3)n2)CC1 | null | null | [Al+3] | [H-] | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | Compound of Example 151 was reduced with LAH in THF at 60° C. analogous to Example 53. | NCCCN1CCC(Nc2nccc(-c3cc4ccccc4s3)n2)CC1 | null | null | null |
810,510 | ord_dataset-da49b0378abf41bf92ab8ecdd3feb28b | null | 2008-01-01T00:02:00 | true | N[C@@H:2]([CH:6](C)C)[C@H:3](O)[CH3:4].[NH2:9][C@@H:10]([CH:19]([CH3:21])[CH3:20])[C@@H:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[OH:12].C([O-])([O-])=O.[Na+].[Na+].C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O.CCCCCC>[CH3:20][CH:19]([CH3:21])[C@H:10]([N:9]1[CH2:4][CH2:3][CH2:2][CH2:6]1)[C@@H:11]([C:13]1[CH:18]=[CH:17]... | CC(C)[C@H](N)[C@@H](C)O | CC(C)[C@H](N)[C@H](O)c1ccccc1 | null | O=C([O-])[O-] | [K+] | [Na+] | 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 | Repeat Step (a) of EXAMPLE 1, but replace (2R,3S)-3-amino-4-methylpentan-2-ol with (1R,2S)-2-amino-3-methyl-1-phenylbutan-1-ol, and replace Na2CO3 (1.16 g, 11.0 mmol) with K2CO3 (1.52 g, 11.0 mmol). Column chromatography (Silica gel, eluent is n-Hexane:EtOAc=10:1) is used to purify the coarse product and a slightly-yel... | CC(C)[C@@H]([C@H](O)c1ccccc1)N1CCCC1 | null | 86 | null |
1,583,124 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | [Si:1]([O:8][C@H:9]1[CH2:18][C:17]([CH3:20])([CH3:19])[CH2:16][C:15]2[N:14]=[C:13]([CH:21]([CH3:23])[CH3:22])[C:12]3[C@@H:24]([C:33]4[C:38]([F:39])=[CH:37][C:36]([C:40]([F:43])([F:42])[F:41])=[CH:35][N:34]=4)[O:25][C:26]4([CH2:31][CH2:30][O:29][CH2:28][CH:27]4I)[C:11]=3[C:10]1=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3]... | CC(C)c1nc2c(c3c1[C@@H](c1ncc(C(F)(F)F)cc1F)OC31CCOCC1I)[C@@H](O[Si](C)(C)C(C)(C)C)CC(C)(C)C2 | null | null | [Pd+2] | [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 | Obtained by starting from (3S,9S)-9-(tert-butyldimethylsilyloxy)-3-(3-fluoro-5-(trifluoromethyl)pyridin-2-yl)-3′-iodo-4-isopropyl-7,7-dimethyl-2′,3′,5′,6,6′,7,8,9-octahydro-3H-spiro[furo[3,4-c]quinoline-1,4′-pyran]. 10% palladiumhydroxide on charcoal is used instead of 10% palladium on charcoal. | CC(C)c1nc2c(c3c1[C@@H](c1ncc(C(F)(F)F)cc1F)OC31CCOCC1)[C@@H](O[Si](C)(C)C(C)(C)C)CC(C)(C)C2 | null | null | null |
1,583,143 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | [Si:1]([O:8][C@H:9]1[CH2:18][C:17]2([CH2:21][CH2:20][CH2:19]2)[CH2:16][C:15]2[N:14]=[C:13]([CH:22]([CH3:24])[CH3:23])[C:12]([CH:25]=[O:26])=[C:11]([I:27])[C:10]1=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Br[C:29]1[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][N:30]=1>>[Si:1]([O:8][C@H:9]1[CH2:18][... | CC(C)c1nc2c(c(I)c1C=O)[C@@H](O[Si](C)(C)C(C)(C)C)CC1(CCC1)C2 | FC(F)(F)c1ccc(Br)nc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Obtained by starting from (S)-5′-(tert-butyldimethylsilyloxy)-4′-iodo-2′-isopropyl-6′,8′-dihydro-5′H-spiro[cyclobutane-1,7′-quinoline]-3′-carbaldehyde and 2-bromo-5-(trifluoromethyl)pyridine. | CC(C)c1nc2c(c(I)c1[C@@H](O)c1ccc(C(F)(F)F)cn1)[C@@H](O[Si](C)(C)C(C)(C)C)CC1(CCC1)C2 | null | null | null |
287,202 | ord_dataset-3577d334f6eb4dc4bd73564fee3f0dfc | null | 1994-01-01T00:03:00 | true | [C:1]([C:5]1[N:6]=[C:7]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:13]=2[CH:20]=O)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C(OC(=O)C)(=O)C>C1(C)C(C)=CC=CC=1>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:13]=3[CH:20]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3]... | COc1ccc(OCc2nc(C(C)(C)C)cs2)c(C=O)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1C | CC(=O)OC(C)=O | null | null | null | null | null | null | null | null | null | 140 | 14 | A mixture of 4-tert-butyl-2-(2-formyl-4-methoxyphenoxymethyl)thiazole (3.23 g) and acetic anhydride (3.2 ml) in xylene (30 ml) was stirred at 140° C. for 14 hours. After being cooled, the resulting mixture was concentrated to give a syrup. The syrup was subjected to column chromatography on silica gel and eluted with t... | COc1ccc2oc(-c3nc(C(C)(C)C)cs3)cc2c1 | null | 79 | null |
509,458 | ord_dataset-85c00026681b46f89ef8634d2b8618c3 | null | 2001-01-01T00:07:00 | true | [C:1]1([C:7]2[N:11]3[N:12]=[C:13]([O:22][CH2:23][C:24]4[N:25](COCC[Si](C)(C)C)[N:26]=[CH:27][N:28]=4)[C:14]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:15][C:10]3=[N:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[C:1]1([C:7]2[N:11]3[N:12]=[C:13]([O:22][CH2:23][C:24]4[NH:25][N... | C[Si](C)(C)CCOCn1ncnc1COc1nn2c(-c3ccccc3)nnc2cc1-c1ccccc1 | null | null | Cl | O=C([O-])[O-] | [Na+] | 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 | 65 | null | The product from Example 72 Step b) (0.68 g) was suspended in ethanol (10 ml) with 2 N hydrochloric acid (21 ml) and heated at 65° C. for 5.5 h. Saturated sodium carbonate solution was added dropwise until a solid precipitated and this was collected by filtration and washed several. times with water in the sinter funne... | c1ccc(-c2cc3nnc(-c4ccccc4)n3nc2OCc2ncn[nH]2)cc1 | null | null | null |
1,219,846 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | C([O:8][C:9]1[C:14]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[CH:13][CH:12]=[CH:11][C:10]=1[C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)C1C=CC=CC=1>CO>[N:17]1[CH:18]=[CH:19][CH:20]=[C:15]([C:14]2[CH:13]=[CH:12][CH:11]=[C:10]([C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)[C:9]=2[OH:8])[CH:16]=1 | c1ccc(COc2c(-c3cccnc3)cccc2-c2cccnc2)cc1 | null | 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 | 25 | 16 | 2,6-Bis(3-pyridyl)phenyl benzyl ether (16.70 g, 49.35 mmol) was dissolved in MeOH (200 mL). Argon was bubbled through this solution for 10 min to remove oxygen. Then Pd/C (500 mg 5 w %) was added, and the reaction mixture was put into the Parr-reactor and shaken for 16 hr under a hydrogen atmosphere at 80 psi. After th... | Oc1c(-c2cccnc2)cccc1-c1cccnc1 | null | null | null |
1,235,733 | ord_dataset-e96f5a2842f14e5380461c234100f05a | null | 2012-01-01T00:12:00 | true | [F:1][C:2]1[CH:25]=[C:24]([N+:26]([O-])=O)[CH:23]=[CH:22][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[N:15]=[CH:16][N:17]([CH2:19][CH2:20][CH3:21])[CH:18]=3)[S:13][C:6]=12.[BH4-].[Na+]>CO.C1COCC1.Cl[Ni]Cl>[F:1][C:2]1[CH:25]=[C:24]([CH:23]=[CH:22][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=... | CCCn1cnc(-c2cc3nccc(Oc4ccc([N+](=O)[O-])cc4F)c3s2)c1 | null | null | Cl[Ni]Cl | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CO | null | null | null | null | null | null | null | null | null | null | 1 | To a solution of the nitro compound 132 (4.13 g, 10.36 mmol) in MeOH/THF (100 ml/100 mL) was added NiCl2×6H2O (4.92 g, 20.73 mmol) and NaBH4 (1.54 mg, 41.44 mmol). The reaction mixture was allowed to stir for 1 hr, concentrated to dryness and the resultant solid was dissolved in 2 M HCl. The acidic solution was then ma... | CCCn1cnc(-c2cc3nccc(Oc4ccc(N)cc4F)c3s2)c1 | null | 86.7 | null |
1,307,104 | ord_dataset-78c3f723155a4347a902b53bcee1524d | null | 2013-01-01T00:06:00 | true | BrC1C=CC=C2C=1C(C1C(O)=CC3OCOC=3C=1)[C:5](=[O:16])N2CCCCC.[Br:27][C:28]1[CH:36]=[CH:35][CH:34]=[C:33]2[C:29]=1[CH:30]([C:44]1[CH:49]=[C:48]([F:50])[C:47]([F:51])=[CH:46][C:45]=1[OH:52])[C:31](=[O:43])[N:32]2[CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39]>>[Br:27][C:28]1[CH:36]=[CH:35][CH:34]=[C:33]2[C:29]=1[C:30]([C:44]1... | CCOC(=O)CN1C(=O)C(c2cc(F)c(F)cc2O)c2c(Br)cccc21 | CCCCCN1C(=O)C(c2cc3c(cc2O)OCO3)c2c(Br)cccc21 | null | null | null | null | null | null | null | 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 PREPARATION 1E, and making non-critical variations to replace 4-bromo-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1-pentyl-1,3-dihydro-2H-indol-2-one with ethyl [4-bromo-3-(4,5-difluoro-2-hydroxyphenyl)-2-oxo-2,3-dihydro-1H-indol-1-yl]acetate, the title compound was obtained (83%): MS (ES... | CCOC(=O)CN1C(=O)C(CO)(c2cc(F)c(F)cc2O)c2c(Br)cccc21 | null | null | null |
1,404,718 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | [F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[F:10][C:11]([Si](C)(C)C)([F:13])[F:12].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([OH:7])[C:11]([F:13])([F:12])[F:10])=[CH:4][CH:3]=1 | C[Si](C)(C)C(F)(F)F | O=Cc1ccc(F)cc1 | null | CCCC[N+](CCCC)(CCCC)CCCC | [F-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | According to Reference Example 8-12, by use of 4-fluorobenzaldehyde (500 mg, 4.03 mmol), (trifluoromethyl)trimethylsilane (715 μL, 4.83 mmol), tetrabutylammonium fluoride (a 1.0 mol/L solution in tetrahydrofuran, 403 μL, 0.403 mmol) and tetrahydrofuran (10 mL), the mixture was stirred and reacted at room temperature fo... | OC(c1ccc(F)cc1)C(F)(F)F | null | 121.2 | null |
258,835 | ord_dataset-b17fdf55f5f945a48d47a588fc255573 | null | 1992-01-01T00:12:00 | true | [NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:46]/[O:47][CH3:48])/[C:8]([NH:10][CH:11]2[C:44](=[O:45])[N:13]3[C:14]([C:28]([O:30]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:29])=[C:15]([C:18]4[C:21](=[O:22])[C:20](=[O:23])[C:19]=4[O:24][CH:25]([CH3:27])[CH3:26])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.FC(F)(F)C(O)=O>C1(OC)C=CC=CC=1>[NH2:... | CO/N=C(\C(=O)NC1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(c3c(OC(C)C)c(=O)c3=O)CS[C@H]12)c1csc(N)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 | COc1ccccc1 | null | null | null | null | null | null | null | null | null | null | 1 | Diphenylmethyl 7-[2-(2-aminothiazol-4-yl)-(Z)-2-methoxyiminoacetamido]-3-[3,4-dioxo-2-(2-propoxy)-1-cyclobutenyl]-3-cephem-4-carboxylate (33 mg) was added to a stirred, cooled (ice/H2O bath) solution of trifluoroacetic acid (100 μL) and anisole (50 μL). The cooling bath was removed, and stirring was continued for 1 hr ... | CO/N=C(\C(=O)NC1C(=O)N2C(C(=O)O)=C(c3c(OC(C)C)c(=O)c3=O)CS[C@H]12)c1csc(N)n1 | null | null | null |
1,078,863 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | [F:1][C:2]1[C:7]2[C:8]([C:18](=[O:21])[NH:19][CH3:20])=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[O:10][C:6]=2[CH:5]=[CH:4][C:3]=1[C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][C:30]=1[CH3:31])[C:25]([OH:27])=O.[CH3:32][C:33]1[CH:38]=[C:37]([CH3:39])[N:36]=[C:35]([C:40]2([NH2:43])[CH2:42][CH2:41]2)[N:34]=1.F[P... | CNC(=O)c1c(-c2ccc(F)cc2)oc2ccc(-c3cc(C(=O)O)ccc3C)c(F)c12 | Cc1cc(C)nc(C2(N)CC2)n1 | null | CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | 8 | To a mixture of 3-(4-fluoro-2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-5-yl)-4-methylbenzoic acid (50 mg, 0.12 mmol), crude 1-(4,6-dimethylpyrimidin-2-yl)cyclopropanamine (150 mg) in 2 ml DMF at room temperature was added BOP (106 mg, 0.24 mmol, 2.0 eq.) and triethyl amine (0.050 ml, 0.36 mmol, 3.0 eq.), and the ... | CNC(=O)c1c(-c2ccc(F)cc2)oc2ccc(-c3cc(C(=O)NC4(c5nc(C)cc(C)n5)CC4)ccc3C)c(F)c12 | null | null | null |
1,424,907 | ord_dataset-5e6956e6e8c24a168866a253f4a66c6c | null | 2014-01-01T00:05:00 | true | [CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][C@@H:13]([C:17]([OH:19])=O)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C=O)C.CO.C(Cl)(=O)C([Cl:30])=O>>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][C@@H:13]([C:17]([Cl:30])=[O:19])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1 | O=C(O)[C@@H]1CCCN(C(=O)OCc2ccccc2)C1 | O=C(Cl)C(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CO | null | null | null | null | null | null | null | null | null | 25 | 1 | (R)-Piperidine-1,3-dicarboxylic acid 1-benzyl ester (XXVIII) (8.00 g, 30.4 mmol) was taken in neat oxalyl chloride (20 ml), 0.2 ml of DMF were added and the mixture was stirred at room temperature for 1 hour. The completion of reaction was monitored by TLC which showed the formation of a non-polar spot after treatment ... | O=C(Cl)[C@@H]1CCCN(C(=O)OCc2ccccc2)C1 | null | null | null |
1,240,773 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [OH:1][B:2]1[C:6]2[CH:7]=[C:8]([OH:12])[CH:9]=[C:10]([CH3:11])[C:5]=2[CH:4]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[O:3]1.CCN(C(C)C)C(C)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>C(Cl)Cl>[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([O:12][S:29]([CH3:28])(=[O:31])=[O:30])[CH:9]=[C:10]([CH3:11])[C:5]=2[CH:4]([CH2:13][C:14]([O:16][CH2... | CS(=O)(=O)Cl | CCOC(=O)CC1OB(O)c2cc(O)cc(C)c21 | 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 | 8 | To a solution of ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (500 mg, 2 mmol), DIPEA (774 mg, 6 mmol) in DCM (10 mL) was slowly added MsCl (366 mg, 3.2 mmol) at −78° C. The reaction mixture was stirred overnight at room temperature, quenched with saturated NH4Cl and washed with saturat... | CCOC(=O)CC1OB(O)c2cc(OS(C)(=O)=O)cc(C)c21 | null | null | null |
241,537 | ord_dataset-9f54014563f44962b72e288618421b97 | null | 1992-01-01T00:02:00 | true | Cl.Cl[CH2:3][CH2:4][NH:5][CH2:6][CH2:7]Cl.[CH3:9][O:10][C:11]1[CH:12]=[C:13]([CH:15]=[C:16]([O:20][CH3:21])[C:17]=1[O:18][CH3:19])[NH2:14].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH3:21][O:20][C:16]1[CH:15]=[C:13]([N:14]2[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]2)[CH:12]=[C:11]([O:10][CH3:9])[C:17]=1[O:18][CH3:19] | COc1cc(N)cc(OC)c1OC | ClCCNCCCl | null | Cl | O=C([O-])[O-] | [K+] | 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 | 16 | A solution of 44.3 g (0.25 mol) of bis(2-chloroethyl)amine hydrochloride and 45.5 g (0.25 mol) of 3,4,5-trimethoxyaniline in 550 mL of absolute ethanol was heated at reflux for 16 h under a nitrogen atmosphere. The mixture was cooled and 50.0 g (0.36 mol) of potassium carbonate was added and heating was continued for 1... | COc1cc(N2CCNCC2)cc(OC)c1OC | null | 37.4 | null |
1,653,910 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [F:1][C:2]1[C:3]([OH:24])=[C:4]([CH:18]=[C:19]([N+:21]([O-:23])=[O:22])[CH:20]=1)[CH2:5][N:6]([CH3:17])[C:7](=[O:16])[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Si:25]([O:32][CH2:33][C@H:34](O)[CH3:35])([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N... | C[C@@H](O)CO[Si](C)(C)C(C)(C)C | CN(Cc1cc([N+](=O)[O-])cc(F)c1O)C(=O)OCc1ccccc1 | null | CC(C)OC(=O)/N=N/C(=O)OC(C)C | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 16 | To a solution of 27B (400 mg, 1.197 mmol), 33A (251 mg, 1.316 mmol) and triphenylphosphine (345 mg, 1.316 mmol) in THF (10 mL) at 0° C., was added DIAD (0.256 mL, 1.316 mmol) dropwise. The reaction mixture was allowed to slowly warm to rt and stirred for 16 h, then was concentrated. The crude product was purified by fl... | C[C@@H](CO[Si](C)(C)C(C)(C)C)Oc1c(F)cc([N+](=O)[O-])cc1CN(C)C(=O)OCc1ccccc1 | null | 95.2 | null |
1,002,615 | ord_dataset-70899a0178cc441482746c093624afa0 | null | 2010-01-01T00:10:00 | true | CC(C)([O-])C.[K+].[CH2:7]([NH:9][C:10]([C:12]1[S:30][C:15]2[N:16]=[C:17]([NH2:29])[N:18]=[C:19]([C:20]3[CH:25]=[C:24]([OH:26])[C:23]([Cl:27])=[CH:22][C:21]=3[Cl:28])[C:14]=2[CH:13]=1)=[O:11])[CH3:8].O.[CH2:32]([O:34][CH:35]([O:38][CH2:39][CH3:40])[CH2:36]Br)[CH3:33]>C(#N)C>[CH2:7]([NH:9][C:10]([C:12]1[S:30][C:15]2[N:16... | CCNC(=O)c1cc2c(-c3cc(O)c(Cl)cc3Cl)nc(N)nc2s1 | CCOC(CBr)OCC | null | CC(C)(C)[O-] | [K+] | 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 | Potassium tert-butoxide was added to a suspension of 2-Amino-4-(2,4-dichloro-5-hydroxyphenyl)-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl amide in acetonitrile, bromoacetaldehyde diethyl acetal was added and the suspension heated under reflux for ˜8 hrs. The resulting suspension was allowed to cool and water added,... | CCNC(=O)c1cc2c(-c3cc(OCC(OCC)OCC)c(Cl)cc3Cl)nc(N)nc2s1 | null | null | null |
241,916 | ord_dataset-9f54014563f44962b72e288618421b97 | null | 1992-01-01T00:02:00 | true | [F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:11][CH:10]=1.[C:23](=[O:25])=[O:24]>>[CH2:16]([O:15][C:12]1[CH:13]=[CH:14][C:9]([C:3]2[CH:4]=[CH:5][C:6]([C:23]([OH:25])=[O:24])=[C:7]([F:8])[C:2]=2[F:1])=[CH:10][CH:11]=1)[C... | CCCCCCCOc1ccc(-c2cccc(F)c2F)cc1 | O=C=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | -78 | 3 | 0.1 mol of 2,3-difluoro-4'-heptyloxybiphenyl is metalated according to 1b). The mixture is stirred for 3 hours at -78° C. and the reaction mixture is then tipped in one swing onto 200 g of pulverized dry ice. The mixture is subsequently worked up as customary. | CCCCCCCOc1ccc(-c2ccc(C(=O)O)c(F)c2F)cc1 | null | null | null |
407,080 | ord_dataset-d5bb2294ac964841b8ffc9e0a34e93af | null | 1998-01-01T00:07:00 | true | C1(OC(=O)N[C:10]2[C:11]([O:19][CH3:20])=[N:12][C:13]([CH3:18])=[C:14]([CH2:16][CH3:17])[CH:15]=2)C=CC=CC=1.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1>>[CH2:16]([C:14]1[CH:15]=[C:10]([CH2:14][CH2:13][NH:12][C:11]([N:33]2[CH2:34][CH2:35][N:30]([C:25]3[CH:26]... | COc1ccccc1N1CCNCC1 | CCc1cc(NC(=O)Oc2ccccc2)c(OC)nc1C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Phenyl-N-(5-ethyl-2-methoxy-6-methylpyridin-3-yl)carbamate and 1-(2-methoxyphenyl)piperazine were reacted by the same way with the example 1 to obtain the titled compound. | CCc1cc(CCNC(=O)N2CCN(c3ccccc3OC)CC2)c(OC)nc1C | null | 63 | null |
49,793 | ord_dataset-0bb2e99daa66408fb8dbd6a0781d241c | null | 1978-01-01T00:12:00 | true | C(O[C:4]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[CH:5][C:6]1[CH2:10][CH2:9][CH2:8][N:7]=1)C.F[B-](F)(F)F>C(N)(C)C>[CH:6]([N:7]=[C:4]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH:5]=[C:6]1[CH2:10][CH2:9][CH2:8][NH:7]1)([CH3:10])[CH3:5] | CCOC(=CC1=NCCC1)c1ccccc1 | null | null | F[B-](F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)N | null | null | null | null | null | null | null | null | null | null | null | null | By refluxing the solution of 9.1 g (0.03 mole) of 2-(2-ethoxy-2-phenyl-ethenyl)-1-pyrroline-tetrafluoroborate in 30 ml of isopropylamine for 1 hour and processing analogously to Example 1, there is obtained crude 2-[2-(isopropylimino)-2-phenylethylidene]-pyrrolidine. The crude base is dissolved in isopropanol, and 2.8 ... | CC(C)N=C(C=C1CCCN1)c1ccccc1 | null | null | null |
351,421 | ord_dataset-127eb5fdd5b4402e92b51d0b55a5dcb5 | null | 1997-01-01T00:01:00 | true | Cl[CH2:2][C:3]1[S:4][C:5]([CH3:14])=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1.[OH:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=1>>[CH3:14][C:5]1[S:4][C:3]([CH2:2][O:15][C:16]2[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=2)=[N:7][C:6]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]... | Cc1sc(CCl)nc1-c1ccccc1 | O=Cc1ccc(O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | According to the method described for Reference Example 45, 2-chloromethyl-5-methyl-4-phenylthiazole was allowed to react with p-hydroxybenzaldehyde to give 4-(5-methyl-4-phenyl-2-thiazolylmethoxy)benzaldehyde. Recrystallization from ethyl acetate--isopropyl ether gave colorless prisms, m.p.81°-82° C. | Cc1sc(COc2ccc(C=O)cc2)nc1-c1ccccc1 | null | null | null |
949,633 | ord_dataset-3feb2a95f66e4706a4a50c977ccd9bf8 | null | 2010-01-01T00:04:00 | true | [NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])=[N:6][CH:7]=1.[Cl:17]N1C(=O)CCC1=O>C(#N)C>[NH2:1][C:2]1[C:7]([Cl:17])=[N:6][C:5]([CH:8]([C:9]([F:10])([F:11])[F:12])[C:13]([F:16])([F:14])[F:15])=[CH:4][CH:3]=1 | O=C1CCC(=O)N1Cl | Nc1ccc(C(C(F)(F)F)C(F)(F)F)nc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | null | null | In 10 ml of acetonitrile was dissolved 0.56 g (2.3 mmol) of 5-amino-2-[2,2,2-trifluoro-1-(trifluoromethyl)ethyl]pyridine, to which was added 0.31 g (2.3 mmol) of N-chlorosuccinimide (NCS). The mixture thus obtained was heated under reflux for one hour to make progress a reaction. The solvent was distilled off under red... | Nc1ccc(C(C(F)(F)F)C(F)(F)F)nc1Cl | null | 85.8 | null |
1,717,896 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [CH:1]1([C:4]2[O:8][C:7]([C:9]3[C:10]([NH2:25])=[N:11][CH:12]=[C:13]([C:15]4[CH:16]=[C:17]5[C:21](=[CH:22][CH:23]=4)[N:20]([CH3:24])[CH:19]=[CH:18]5)[CH:14]=3)=[N:6][N:5]=2)[CH2:3][CH2:2]1.C([SiH](CC)CC)C.C([O-])(O)=O.[Na+]>C(O)(C(F)(F)F)=O.O>[CH:1]1([C:4]2[O:8][C:7]([C:9]3[C:10]([NH2:25])=[N:11][CH:12]=[C:13]([C:15]4[... | Cn1ccc2cc(-c3cnc(N)c(-c4nnc(C5CC5)o4)c3)ccc21 | null | null | CC[SiH](CC)CC | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | O | null | null | null | null | null | null | null | null | null | 0 | 2 | To a solution of 3-(5-cyclopropyl-[1,3,4]oxadiazol-2-yl)-5-(1-methyl-1H-indol-5-yl)-pyridin-2-ylamine (160 mg, 0.48 mmol) in TFA at 0° C. was added triethylsilane (0.2 mL, 1.20 mmol) drop-wise over a period of 5 min, and stirred for 2 h at 0° C. The reaction mixture was diluted with water (20 mL) and neutralized with s... | CN1CCc2cc(-c3cnc(N)c(-c4nnc(C5CC5)o4)c3)ccc21 | null | 50 | null |
886,512 | ord_dataset-d728a2f811c0424cbcdb5a84d02b93ae | null | 2009-01-01T00:06:00 | true | [OH:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:9][C:10]1[CH:11]=[C:12]([CH:14]=[CH:15][CH:16]=1)[NH2:13]>O.CC(C)=O>[Cl:9][C:10]1[CH:11]=[C:12]([NH:13][C:5]2[C:4]([NH:13][C:12]3[CH:14]=[CH:15][CH:16]=[C:10]([Cl:9])[CH:11]=3)=[N:3][C:2](=[O:1])[C:7](=[O:8])[CH:6]=2)[CH:14]=[CH:15][CH:16]=1 | Nc1cccc(Cl)c1 | Oc1cccnc1O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(C)=O | null | null | null | null | null | null | null | null | null | null | 2 | 2,3-dihydroxypyridine (0.0027 mol), m-chloroaniline (0.0054 mol), and NaIO3 (0.0009 mol) were dissolved in 160 ml of water/acetone (80:1, v/v) solvent. The reaction mixture was stirred for 2 hours, and maintained still overnight. It was then filtered and recrystallized with chloroform. The final product was 5,6-di(m-ch... | O=C1C=C(Nc2cccc(Cl)c2)C(Nc2cccc(Cl)c2)=NC1=O | null | 36 | null |
242,308 | ord_dataset-9f54014563f44962b72e288618421b97 | null | 1992-01-01T00:02:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2([S:19][CH2:20][CH3:21])[CH2:18][CH2:17]2)([OH:15])[CH2:9][C:10]2[N:14]=[CH:13][NH:12][N:11]=2)=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:30])C=1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2([S:19]([CH2:20][CH3:21])=[O:30])[CH2:17][CH2:18]2)([OH:15])[CH2:9][C:10]2[N:14]=[CH:... | CCSC1(C(O)(Cc2nc[nH]n2)c2ccc(Cl)cc2)CC1 | O=C(OO)c1cccc(Cl)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | null | 5 g (0.0155 mol) of 1-(4-chlorophenyl)-1-[1-(ethylthio)-1-cyclopropyl]-2-(1,2,4-triazol-yl)-1-ethanol (see Example 1) are stirred with 3.3 g of m-chloroperbenzoic acid (80-90% strength) in 40 ml of methylene chloride overnight at room temperature and then for one hour under reflux. Thereafter, the mixture is washed wit... | CCS(=O)C1(C(O)(Cc2nc[nH]n2)c2ccc(Cl)cc2)CC1 | null | 57 | null |
397,589 | ord_dataset-a4a191e812a64d0598ea918f047e8da7 | null | 1998-01-01T00:04:00 | true | [O:1]=[C:2]1[N:8]([CH2:9][C:10]([N:12]([CH:21]([CH3:23])[CH3:22])[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[O:11])[C:7]2[CH:24]=[CH:25][CH:26]=[CH:27][C:6]=2[N:5]([C:28]2[N:33]=[CH:32][CH:31]=[CH:30][N:29]=2)[C:4](=[O:34])[C:3]1=[N:35]NC1C=CC=CC=1>C(O)(=O)C.[Zn]>[NH2:35][CH:3]1[C:2](=[O:1])[N:8]([C... | COc1ccc(N(C(=O)Cn2c(=O)c(=NNc3ccccc3)c(=O)n(-c3ncccn3)c3ccccc32)C(C)C)cc1 | null | null | [Zn] | 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 | 1 | To a stirred solution of 2-[2,4-dioxo-3-(phenyl-hydrazono)-5-pyrimidin-2-yl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepine-1-yl]-N-isopropyl-N-(4-methoxy-phenyl)-acetamide (500 mg, 0.886 mmol) in acetic acid (12 mL) at ambient temperature was added zinc dust (530 mg) and the resulting mixture was stirred 1 h. The zinc was s... | COc1ccc(N(C(=O)CN2C(=O)C(N)C(=O)N(c3ncccn3)c3ccccc32)C(C)C)cc1 | null | 60.6 | null |
627,133 | ord_dataset-e44331dc51de453ca14b7032593c1958 | null | 2004-01-01T00:02:00 | true | [CH2:1]([C:3]1(O)[CH:10]2[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:12][CH:4]1[CH2:5]3)[CH2:9]2)[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH:1](=[C:3]1[CH:4]2[CH2:12][CH:8]3[CH2:7][CH:6]([CH2:11][CH:10]1[CH2:9]3)[CH2:5]2)[CH3:2] | CCC1(O)C2CC3CC(C2)CC1C3 | null | null | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | 70 g of 2-ethyl-2-adamantanol was dissolved in toluene, 1 g of p-toluenesulfonic acid was added, and water was removed by distillation by use of a Dean and Stark dehydrator under heating so as to obtain 2-ethylideneadamantane. To 50 g of the obtained 2-ethylideneadamantane, 500 g of methacrylic acid and 0.1 ml of conce... | CC=C1C2CC3CC(C2)CC1C3 | null | null | null |
56,749 | ord_dataset-12a0ec4f3cda46e2badc694da2072c39 | null | 1979-01-01T00:06:00 | true | Cl[C:2]1([CH2:10][CH:11]=[CH2:12])[C:7](=[O:8])[CH2:6][CH2:5][CH2:4]C1=O>C1(C)C(C)=CC=CC=1>[CH2:10]([C:2]1[C:7](=[O:8])[CH2:6][CH2:5][CH:4]=1)[CH:11]=[CH2:12] | C=CCC1(Cl)C(=O)CCCC1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1C | null | null | null | null | null | null | null | null | null | null | null | 4.5 | Anhydrous powdered sodium carbonate (670 g) and 1300 ml of dry (alumina) xylene were placed in a 3-l., three-necked flask equipped with a Dean-Stark trap, condenser, vibra-mixer, dropping funnel and argon inlet. The flask was flushed with argon and the contents brought to reflux. A solution of 2-chloro-2-allyl-1, 3-cyc... | C=CCC1=CCCC1=O | null | 49.5 | null |
1,093,104 | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | null | 2011-01-01T00:09:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][C:17]([CH:24]=[O:25])=[CH:16][N:15]=2)[CH2:10][C@H:9]1[CH3:26])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([C:20]([F:23])([F:21])[F:22])=[CH:18][C:17]([CH2:2... | C[C@@H]1CN(c2ncc(C=O)cc2C(F)(F)F)CCN1C(=O)OC(C)(C)C | 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 | To a solution of (2R)-4-(5-formyl-3-trifluoromethyl-pyridin-2-yl)-2-methyl-piperazine-1-carboxylic acid tert-butyl ester from step (e) above (4.48 g, 12 mmol) in methanol (30 mL) was added portionwise NaBH4 (542 mg, 14.4 mmol, Aldrich) with stirring at 0° C. The mixture was stirred at 0° C. for 30 min and the solvent w... | C[C@@H]1CN(c2ncc(CO)cc2C(F)(F)F)CCN1C(=O)OC(C)(C)C | null | null | null |
699,686 | ord_dataset-bbd7e53f000345838ad4920a07a169ff | null | 2006-01-01T00:03:00 | true | I[CH2:2][C:3]1([CH3:19])[O:14][C:13]2[C:5](=[C:6]3[C:10](=[C:11]([CH3:16])[C:12]=2[CH3:15])[NH:9][C:8]([CH3:18])([CH3:17])[CH2:7]3)[CH2:4]1.Cl.[CH3:21][N:22]([CH:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1)[C:23]1[S:24][C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=2[N:27]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C(=O)C>[CH3:2... | CN(c1nc2ccccc2s1)C1CCNCC1 | Cc1c(C)c2c(c3c1NC(C)(C)C3)CC(C)(CI)O2 | null | Cl | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)N(C)C | O | null | null | null | null | null | null | null | null | null | 180 | 6 | A suspension of 1,6,7,8-tetrahydro-2-(iodomethyl)-2,4,5,7,7-pentamethyl-2H-furo[3,2-e]indole (372 mg, 1.0 mmol), N-methyl-N-(4-piperidinyl)-1,3-benzothiazole-2-amine hydrochloride (427 mg, 1.5 mmol) and potassium carbonate (485 mg, 3.5 mmol) in N,N-dimethylacetamide (2 mL) was stirred at 180° C. for 6 hours under the n... | Cc1c(C)c2c(c3c1NC(C)(C)C3)CC(C)(CN1CCC(N(C)c3nc4ccccc4s3)CC1)O2 | null | 56.2 | null |
435,871 | ord_dataset-386da077ab2340638cada986e2ef0770 | null | 1999-01-01T00:07:00 | true | [ClH:1].[NH:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH2:7][CH2:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][CH:10]=1>Cl>[ClH:1].[NH:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH2:7][CH2:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=1 | COC(=O)c1ccc(CCc2ncc[nH]2)cc1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 16 | Ester 23-4 (450 mg; 1.77 mmol) was dissolved in 6N HCl and stirred for 16 h. Concentration provided 23-5 as dark oil. Rf 0.28 (silica, 4:1:1 CH2Cl2 /MeOH/HOAc). | O=C(O)c1ccc(CCc2ncc[nH]2)cc1 | null | null | null |
605,451 | ord_dataset-273fda773e864aaf9b71a30a2d9f2162 | null | 2003-01-01T00:08:00 | true | [OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:19])[C:7]([CH3:18])=[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:9]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:26](Br)[C:27]#[CH:28]>CC(C)=O>[C:26]([O:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:19])[C:7]([CH3:18])=[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=... | C#CCBr | Cc1c(-c2ccccc2)oc2cc(O)ccc2c1=O | null | O=C([O-])[O-] | [K+] | 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 | A mixture of 7-hydroxy-3-methylflavone (2.52 g, 0.01 mol), K2CO3 (2.8 g, 0.02 mol), Kl (0.166 g, 0.001 mol), propargyl bromide (1.78 g, 0.015 mol) and acetone (100 mL) was refluxed 10 h and hot filtered. The solvent was evaporated and the residue was crystallized by toluene. This yields 2.32 g of a product with the fol... | CC#COc1ccc2c(=O)c(C)c(-c3ccccc3)oc2c1 | null | null | null |
964,326 | ord_dataset-ed65749688da45af8a8432967b017729 | null | 2010-01-01T00:05:00 | true | [O:1]=[S:2]1(=[O:30])[CH2:7][CH2:6][N:5]([C:8]([C:10]2[NH:11][C:12]3[C:17]([CH:18]=2)=[CH:16][C:15]([C:19]([N:21]2[CH2:26][CH2:25][N:24]([CH:27]([CH3:29])[CH3:28])[CH2:23][CH2:22]2)=[O:20])=[CH:14][CH:13]=3)=[O:9])[CH2:4][CH2:3]1.[Cl:31][C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][N:33]=1.N1C=CC=CC=1>C([O-])(=O)C.[Cu+2]... | OB(O)c1ccc(Cl)nc1 | CC(C)N1CCN(C(=O)c2ccc3[nH]c(C(=O)N4CCS(=O)(=O)CC4)cc3c2)CC1 | null | [Cu+2] | CC(=O)[O-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | The title compound was synthesized in analogy to example 66, from [2-(1,1-dioxo-thiomorpholine-4-carbonyl)-1H-indol-5-yl]-(4-isopropyl-piperazin-1-yl)-methanone (example 1), 2-chloropyridine-5-boronic acid, copper(II) acetate, pyridine and using chloroforme instead of dichloromethane as solvent, to give the desired pro... | CC(C)N1CCN(C(=O)c2ccc3c(c2)cc(C(=O)N2CCS(=O)(=O)CC2)n3-c2ccc(Cl)nc2)CC1 | null | 19 | null |
1,096,659 | ord_dataset-af85e6f81c2d49f08086afd6d9e6959c | null | 2011-01-01T00:10:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[O:12].Br[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2([OH:12])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1 | Brc1ccccn1 | O=C1Nc2ccc(Cl)cc2C1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | With 10.0 g of 5-chloro-1H-indol-2,3-dione and 25.3 g of bromo pyridine as starting materials, 5.03 g of the title compound (orange color solid) was obtained by a similar method to Step 34-3. | O=C1Nc2ccc(Cl)cc2C1(O)c1ccccn1 | null | 35 | null |
1,463,280 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | COC1C=C(OC)C=CC=1C[N:6]1[CH2:10][C@H:9]([CH:11]([CH3:13])[CH3:12])[N:8]([CH2:14][C:15]([NH:17][C:18]2[CH:19]=[N:20][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:23]=2)=[O:16])[C:7]1=[O:28]>FC(F)(F)C(O)=O>[O:28]=[C:7]1[NH:6][CH2:10][C@H:9]([CH:11]([CH3:12])[CH3:13])[N:8]1[CH2:14][C:15]([NH:17][C:18]1[CH:19]=[N:20][C:2... | COc1ccc(CN2C[C@H](C(C)C)N(CC(=O)Nc3ccc(C(F)(F)F)nc3)C2=O)c(OC)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | 25 | 3 | Trifluoroacetic acid (20 mL) was added to 2-[(5S)-3-(2,4-dimethoxybenzyl)-2-oxo-5-(propan-2-yl)imidazolidin-1-yl]-N-[6-(trifluoromethyl)pyridin-3-yl]acetamide (900 mg), and the mixture was stirred at room temperature for 3 hr. The solvent was distilled off under reduced pressure, and saturated sodium hydrogen carbonate... | CC(C)[C@H]1CNC(=O)N1CC(=O)Nc1ccc(C(F)(F)F)nc1 | null | 50.1 | null |
1,315,188 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | [CH:1]([O:4][C:5](=[O:21])[NH:6][C@@H:7]1[CH2:20][C:10]2[NH:11][C:12]3[CH:13]=[CH:14][C:15]([C:18]#[N:19])=[CH:16][C:17]=3[C:9]=2[CH2:8]1)([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:28][O:29][C:30]1[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=1[CH2:32]Cl>CN(C=O)C.O>[CH:1]([O:4][C:5](=[O:21])[NH:6][C@@H:7]1[CH2:20][C:10]2... | CC(C)OC(=O)N[C@@H]1Cc2[nH]c3ccc(C#N)cc3c2C1 | COc1ccccc1CCl | null | O=C([O-])[O-] | [Cs+] | 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 | 50 | null | A mixture of ((S)-7-cyano-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-carbamic acid isopropyl ester (2.0 g, 7.06 mmol) and cesium carbonate (3.22 g, 9.88 mmol) in DMF (40 mL) is treated with 2-methoxybenzyl chloride (1.16 g, 7.41 mmol). The reaction is heated at 50° C. for 18 h. The reaction is cooled to room temperatu... | COc1ccccc1Cn1c2c(c3cc(C#N)ccc31)C[C@H](NC(=O)OC(C)C)C2 | null | 98.3 | null |
1,619,603 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([NH:12][S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N+:22]([O-])=O)(=[O:15])=[O:14])[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.Cl[Sn]Cl>Cl.CCO>[NH2:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[S:13]([NH:12][C:10]1[CH:11]=[C:2]([F:1])[CH:3]=[C:4]2[C:9]=1[N:8]=[CH:7][CH:6]=[CH:... | O=[N+]([O-])c1ccccc1S(=O)(=O)Nc1cc(F)cc2cccnc12 | null | null | Cl | Cl[Sn]Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | In a similar fashion using route 1 general procedure 4, N-(6-fluoro-quinolin-8-yl)-2-nitro-benzenesulfonamide (Intermediate 244) (520 mg, 1.49 mmol), SnCl2 (983 mg, 5.99 mmol), 6N HCl (3 drops) and EtOH (10 ml) for 4 h at 80° C. gave the title compound (410 mg, 86%) which was used in the next step without further purif... | Nc1ccccc1S(=O)(=O)Nc1cc(F)cc2cccnc12 | null | 86.7 | null |
1,242,165 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [CH2:1](Br)[CH:2]=[CH2:3].[F:5][C:6]1[CH:11]=[CH:10][C:9]([Mg]Br)=[CH:8][CH:7]=1>O1CCCC1.C(OCC)C.[Cl-].[NH4+]>[CH2:3]([C:9]1[CH:10]=[CH:11][C:6]([F:5])=[CH:7][CH:8]=1)[CH:2]=[CH2:1] | Fc1ccc([Mg]Br)cc1 | C=CCBr | null | [Cl-] | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCOCC | null | null | null | null | null | null | null | null | null | null | 16 | Allyl bromide (4.33 mL, 50 mmol) was added dropwise to a solution of 4-fluorophenyl magnesium bromide (50 mmol) in tetrahydrofuran (25 mL) and diethyl ether (25 mL). After 16 hours, the reaction suspension was diluted with diethyl ether (100 mL) and saturated aqueous ammonium chloride (50 mL). The layers were separated... | C=CCc1ccc(F)cc1 | null | null | null |
1,701,447 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [C:1]1([S:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH:14][C:15](=[NH:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.Cl[P:29]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[C:36]1([P:29]([C:30]2[CH:31]=[CH:32][CH:33]=... | ClP(c1ccccc1)c1ccccc1 | N=C(Nc1ccccc1Sc1ccccc1)c1ccccc1 | null | [Li]CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Procedure as described for NP Amidine I using the following amounts and modifications: 1.34 g of N1-(2-(phenylthio)phenyl)benzamidine (Amidine XIV, 4.4 mmol), 2.20 mL of 2.0 M butyllithium (4.4 mmol), 0.78 mL chlorodiphenylphosphine (4.4 mmol). After filtration to remove lithium chloride and removal of solvent, a stick... | c1ccc(Sc2ccccc2NC(=NP(c2ccccc2)c2ccccc2)c2ccccc2)cc1 | null | null | null |
1,642,358 | ord_dataset-bcc0b01d4f58457a8733b10a099f43ba | null | 2015-01-01T00:10:00 | true | [F:1][C:2]1[CH:26]=[CH:25][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[C:18]4=[N:19][S:20](=[O:24])(=[O:23])[CH2:21][CH2:22][N:17]4[CH:16]=[CH:15][CH:14]=3)=[CH:9][CH:8]=2)=[C:4]([CH3:27])[CH:3]=1>C1COCC1.CO.[Pt](=O)=O>[F:1][C:2]1[CH:26]=[CH:25][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([CH:13]3[C:18]4=[N:19][S:20](=[O:24]... | Cc1cc(F)ccc1Oc1ccc(C2=CC=CN3CCS(=O)(=O)N=C23)cc1 | null | null | O=[Pt]=O | 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 | 50 | 4 | Platinum(IV) oxide (30 mg) was added to a solution of 9-[4-(4-fluoro-2-methylphenoxy)phenyl]-3,4-dihydropyrid o[2,1-c][1,2,4]thiadiazine 2,2-dioxide (303 mg) in THF (dry) (30 mL) and MeOH (30 mL) and the mixture was stirred at 50° C. under hydrogen for 4 hr. The starting material was purified by column chromatography (... | Cc1cc(F)ccc1Oc1ccc(C2CCCN3CCS(=O)(=O)N=C23)cc1 | null | 37.6 | null |
1,463,826 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | [Mg].Cl[CH:3]1[CH2:8][CH2:7][N:6]([CH3:9])[CH2:5][CH2:4]1.[Cl:10][C:11]1[CH:46]=[CH:45][C:14]([C:15]([C:17]2[CH:18]=[C:19]([C:35]3[CH:40]=[CH:39][N:38]=[C:37]([NH:41][C:42](=[O:44])[CH3:43])[CH:36]=3)[S:20][C:21]=2[C:22]2[N:26]=[CH:25][N:24]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[N:23]=2)=[O... | CC(=O)Nc1cc(-c2cc(C(=O)c3ccc(Cl)cc3)c(-c3ncn(COCC[Si](C)(C)C)n3)s2)ccn1 | CN1CCC(Cl)CC1 | null | [Mg] | 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 | 45 | 12 | A 25 mL round bottom flask charged with magnesium turnings (23.0 mg, 0.947 mmol) was flame-dried. To the flask was added tetrahydrofuran (1.00 mL) and a drop of 1,2-dibromoethane. The mixture was heated to 45° C. for 10 min and cooled to rt. To the mixture was added 4-chloro-N-methylpiperidine (126 mg, 0.947 mmol). The... | CC(=O)Nc1cc(-c2cc(C(O)(c3ccc(Cl)cc3)C3CCN(C)CC3)c(-c3ncn(COCC[Si](C)(C)C)n3)s2)ccn1 | null | 44.3 | null |
20,850 | ord_dataset-39f318aa6ec5450182abaf3662294306 | null | 1977-01-01T00:03:00 | true | [NH2:1][CH2:2][CH2:3][SH:4].[CH3:5][C:6]([CH:8]([CH3:10])[CH3:9])=O.C1C=CC=CC=1>O>[CH:8]([C:6]1([CH3:5])[NH:1][CH2:2][CH2:3][S:4]1)([CH3:10])[CH3:9] | NCCS | CC(=O)C(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | 15.43 g (0.2 mol) of cysteamine and 29.0 g (0.2 mol) of isopropyl methyl ketone were treated with 200 ml of benzene and boiled under an inert gas atmosphere for 14 hours on a water-separator. The solution was concentrated on a rotary evaporator and filtered over 25 g of neutral aluminium oxide (activity I). The alumini... | CC(C)C1(C)NCCS1 | null | 77.5 | null |
1,543,961 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [F:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5](O)[N:6]=[C:7]3[C:12]=2[CH:11]=[CH:10][CH:9]=[CH:8]3)[CH:3]=1.P(Cl)(Cl)([Cl:19])=O>CN(C)C=O>[Cl:19][C:5]1[N:6]=[C:7]2[C:12](=[C:13]3[C:4]=1[CH:3]=[C:2]([F:1])[CH:15]=[CH:14]3)[CH:11]=[CH:10][CH:9]=[CH:8]2 | Oc1nc2ccccc2c2ccc(F)cc12 | O=P(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 80 | 3 | To a mixture of 8-fluorophenanthridin-6-ol (Example 2a, 0.15 g, 0.69 mmol) in phosphorus oxychloride (1.06 g, 0.65 mL, 6.9 mmol) was added dimethylformamide (5 mg, 5 μL), and the reaction mixture was warmed to 80° C. and stirred under nitrogen for 3 h. The reaction mixture was cooled to room temperature and evaporated ... | Fc1ccc2c(c1)c(Cl)nc1ccccc12 | null | 93.8 | null |
933,715 | ord_dataset-d8a5dc784dde4465894ec7c69d2e3ba6 | null | 2010-01-01T00:01:00 | true | [OH:1][CH:2]1[CH:8]([OH:9])[CH:7]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)[NH:6][C:5](=[O:18])[NH:4][CH:3]1[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1.CO[C:29](OC)([CH3:31])[CH3:30]>CN(C=O)C>[OH:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][CH:3]2[NH:4][C:5](=[O:18])[NH:6][CH:7]([CH... | COC(C)(C)OC | O=C1NC(Cc2ccc(O)cc2)C(O)C(O)C(Cc2ccc(O)cc2)N1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 65 | 3 | Diol 2.9 (1.8 g, 5.03 mmol) was dissolved in DMF (6 mL) and 2,2-dimethoxypropane (12 mL). P-TsOH (95 mg) was added and the mixture stirred at 65° C. for 3 h. A vacuum was applied to remove water and then the mixture was stirred at 65° C. for a further 1 h. The excess dimethoxypropane was then distilled and the remainin... | CC1(C)OC2C(Cc3ccc(O)cc3)NC(=O)NC(Cc3ccc(O)cc3)C2O1 | null | null | null |
30,942 | ord_dataset-56c07ce5503b46d1805bdf471f8f1c55 | null | 1977-01-01T00:10:00 | true | [F:1][C:2]([F:22])([F:21])[C:3]1[S:7][C:6]([N:8]2[CH:13]([OH:14])[CH2:12][CH2:11][N:10]([C:15]([CH3:19])([CH3:18])[C:16]#[CH:17])[C:9]2=[O:20])=[N:5][N:4]=1.[CH2:23]([N:25]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[O:35][CH3:36])[C:26](Cl)=[O:27])[CH3:24].N1C=CC=CC=1>C1(C)C=CC=CC=1>[F:22][C:2]([F:1])([F:21])[C:3]1[... | CCN(C(=O)Cl)c1ccccc1OC | C#CC(C)(C)N1CCC(O)N(c2nnc(C(F)(F)F)s2)C1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | c1ccncc1 | null | null | null | null | null | null | null | null | null | 25 | 3 | Tetrahydro-1-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)-3-(1,1-dimethylprop-2-ynyl)-6-hydroxy-2(1H)-pyrimidinone (0.05 mole), N-ethyl-N-(2-methoxyphenyl)carbamoyl chloride (0.06 mole), pyridine (0.06 mole) and toluene (150 ml) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and r... | C#CC(C)(C)N1CCC(OC(=O)N(CC)c2ccccc2OC)N(c2nnc(C(F)(F)F)s2)C1=O | null | null | null |
1,137,297 | ord_dataset-aaeaab5f3720492494c1cbbdd0ed2820 | null | 2012-01-01T00:02:00 | true | [C:1]([O:5][C:6](=[O:29])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]2[C:21]3[CH:22]=[C:23]([Cl:26])[CH:24]=[CH:25][C:20]=3[N+:19]([O-])=[N:18][C:17]2=[O:28])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>C(O)(=O)C.O.[Zn]>[C:1]([O:5][C:6](=[O:29])[NH:7][CH:8]1[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][N:16]2[C:21... | CC(C)(C)OC(=O)NC1CCN(CCn2c(=O)n[n+]([O-])c3ccc(Cl)cc32)CC1 | null | null | [Zn] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | O | null | null | null | null | null | null | null | null | null | null | 0.5 | To a solution of tert-butyl{1-[2-(6-chloro-1-oxido-3-oxo-1,2,4-benzotriazin-4(3H)-yl)ethyl]piperidin-4-yl}carbamate (Intermediate 206) (0.43 g) in acetic acid (8 mL) and water (2 mL) was added zinc dust (0.50 g). After 30 minutes, the solution was filtered and the filtrate concentrated. The residue was then treated wit... | CC(C)(C)OC(=O)NC1CCN(CCn2c(=O)nnc3ccc(Cl)cc32)CC1 | null | 16 | null |
315,327 | ord_dataset-bd998d3fe946475e835418aaf647c00d | null | 1995-01-01T00:08:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[CH2:15][NH:14][C:13](=[O:16])[CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH3:17][OH:18]>C1C=CC=CC=1>[CH3:17][O:18][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:8]=1[O:9][CH3:10])[CH2:11][N:14]1[CH2:15][CH:11]([C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:12][C:13... | CO | COc1ccc(C2CNC(=O)C2)cc1OC | null | null | null | 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 | 60 | 6 | 30 g (0.136M) of the pyrrolidone (9) was treated with Triton B (60 ml of a 40% methanol solution in 400 ml of benzene. Benzene was distilled off in vacuo, and 400 ml of benzene was again added to the residue. This procedure was repeated three times, and 25.31 g of 3,4-dimethoxybenzyl chloride was added thereto at room ... | COc1ccc(CN2CC(c3ccc(OC)c(OC)c3)CC2=O)cc1OC | null | 82 | null |
373,050 | ord_dataset-ee5599340390470d8e5b5ac1feddf9d6 | null | 1997-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:22][CH:23]=O)[CH2:10][C:11]([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14]2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].Cl.[C:26]1([C:32]2([OH:38])[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[BH3-]C#N.[Na+]>CO.C1COCC1>[Cl:1][C:2]1[C... | OC1(c2ccccc2)CCNCC1 | O=CCC(CC(=O)n1ccc2ccccc21)c1ccc(Cl)c(Cl)c1 | null | Cl | [BH3-]C#N | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 18 | 1-[3-(3,4-dichlorophenyl)-1,5-dioxopentyl]-1H-indole (740 mg), in MeOH/THF (1:1, 30 mL) was treated sequentially with molecular sieves 3A (880 mg), 4-phenyl-4-hydroxypiperidine HCl (880 mg) and NaBH3CN (130 mg). The resulting mixture was stirred at room temperature for 18 hours. The reaction mixture was with quenched w... | O=C(CC(CCN1CCC(O)(c2ccccc2)CC1)c1ccc(Cl)c(Cl)c1)n1ccc2ccccc21 | null | 56 | null |
937,903 | ord_dataset-90b0aa1f83334a02919b2be3a1c04542 | null | 2010-01-01T00:02:00 | true | Cl[C:2]1[N:11]=[C:10]([OH:12])[C:9]2[C:4](=[C:5]([CH3:15])[C:6]([O:13][CH3:14])=[CH:7][CH:8]=2)[N:3]=1.[CH:16]([C:19]1[CH:23]=[CH:22][NH:21][N:20]=1)([CH3:18])[CH3:17]>>[OH:12][C:10]1[C:9]2[C:4](=[C:5]([CH3:15])[C:6]([O:13][CH3:14])=[CH:7][CH:8]=2)[N:3]=[C:2]([N:21]2[CH:22]=[CH:23][C:19]([CH:16]([CH3:18])[CH3:17])=[N:2... | COc1ccc2c(O)nc(Cl)nc2c1C | CC(C)c1cc[nH]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 | 155 | null | A mixture of 2-chloro-4-hydroxy-7-methoxy-8-methylquinazoline (140) (502 mg, 2.23 mmol) and 3-isopropylpyrazole (500 mg, 4.55 mmol) was heated at 155° C. for 10 min. Then, the reaction mixture was successively cooled down to room temperature, partitioned between CH2Cl2 and water, dried (Na2SO4) and evaporated. The resi... | COc1ccc2c(O)nc(-n3ccc(C(C)C)n3)nc2c1C | null | 63.4 | null |
1,754,026 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [CH:1]1([C:4]2[C:5]([O:13][CH2:14][C:15]([F:18])([F:17])[F:16])=[CH:6][C:7]([C:10]([OH:12])=O)=[N:8][CH:9]=2)[CH2:3][CH2:2]1.Cl.[CH3:20][C:21]([NH:27]C)([CH2:25][CH3:26])[C:22]([NH2:24])=[O:23]>>[C:22]([C:21]([NH:27][C:10]([C:7]1[CH:6]=[C:5]([O:13][CH2:14][C:15]([F:18])([F:17])[F:16])[C:4]([CH:1]2[CH2:2][CH2:3]2)=[CH:9... | CCC(C)(NC)C(N)=O | O=C(O)c1cc(OCC(F)(F)F)c(C2CC2)cn1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was synthesized in analogy to Example 63b, using 5-Cyclopropyl-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid (Example 48c) and 2-Methyl-2-methylamino-butyramide hydrochloride (CAN 18305-22-1) as starting materials and isolated (19.6 mg, 16%) as a white solid; MS (ESI, m/z): 360.5 (M+H+). | CCC(C)(NC(=O)c1cc(OCC(F)(F)F)c(C2CC2)cn1)C(N)=O | null | null | null |
1,246,557 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=2)[N:3]=1.[NH2:16][CH2:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][N:19]1[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25].C(N(C(C)C)CC)(C)C>C1COCC1>[C:27]([O:26][C:24]([N:19]1[CH2:20][CH2:21][CH2:22][CH2:23][CH:18]1[CH2:17... | CC(C)(C)OC(=O)N1CCCCC1CN | Clc1cccc(Nc2nccc(Cl)n2)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 25 | null | To a solution of 4-chloro-N-(3-chlorophenyl)pyrimidin-2-amine (300 mg, 1.25 mmol) and tert-butyl 2-(aminomethyl)-piperidine-1-carboxylate (540 mg, 2.50 mmol) in THF (10 mL) is added diisopropylethyl-amine (0.43 mL, 2.50 mmol). The reaction is heated at reflux for 18 hours and then cooled to room temperature. The crude ... | CC(C)(C)OC(=O)N1CCCCC1CNc1ccnc(Nc2cccc(Cl)c2)n1 | null | 51.3 | null |
685,970 | ord_dataset-56747de2718a4ac5bf061651d1cc9e3e | null | 2005-01-01T00:10:00 | true | [C:1]1([CH3:42])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH2:21][CH2:20][N:19]([S:22]([C:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=3)(=[O:24])=[O:23])[CH2:18][CH2:17][N:16]([S:32]([C:35]3[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=3)(=[O:34])=[O:33])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)(=[O:9])=[O:8])=[CH:3][CH... | Cc1ccc(S(=O)(=O)N2CCNCCN(S(=O)(=O)c3ccc(C)cc3)CCN(S(=O)(=O)c3ccc(C)cc3)CC2)cc1 | CC1(C)OCC2OC2CO1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | null | 50 g (78.76 mmol) of 4,7,10-tris(p-toluenesulfonyl)-1,4,7,10-tetraazacyclododecane and 13.63 g (94.51 mmol) of 4,4-dimethyl-3,5,8-trioxabicyclo-[5.1.0]-octane are dissolved in 300 ml of dimethylformamide and heated in an autoclave for 24 hours to 170° C. It is evaporated to dryness and the residue is chromatographed on... | Cc1ccc(S(=O)(=O)N2CCN(C3COC(C)(C)OCC3O)CCN(S(=O)(=O)c3ccc(C)cc3)CCN(S(=O)(=O)c3ccc(C)cc3)CC2)cc1 | null | null | null |
593,222 | ord_dataset-278fb6af8a994ac69e4d95e6e6eff756 | null | 2003-01-01T00:05:00 | true | [O:1]([CH2:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:17][S:18](O)(=[O:20])=[O:19].ClCCl.P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+]>C(Cl)(Cl)Cl>[N:11]1([CH2:10][CH2:9][CH2:8][O:1][C:2]2[CH:7]=[CH:6][C:5]([S:18]([Cl:17])(=[O:20])=[O:19])=[CH:4][CH:3]=2)[CH2:... | O=S(=O)(O)Cl | c1ccc(OCCCN2CCOCC2)cc1 | null | O=P([O-])([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 0.5 | [3-(Morpholin-4-yl) propoxy] benzene-4-sulfonyl chloride was prepared by chlorosulfonylation of 4-(3-phenoxypropyl)morpholine using chlorosulfonic acid in the presence of dichloromethane or chloroform. For example, to a solution of 2.2 g (10 mmole) of N-(3-phenoxypropyl) morpholine in 20 ml of chloroform, 2 ml of chlor... | O=S(=O)(Cl)c1ccc(OCCCN2CCOCC2)cc1 | null | null | null |
136,310 | ord_dataset-3007013966624a1096d71142f31cb5a3 | null | 1985-01-01T00:10:00 | true | [CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][C:21](OCC)=[O:22])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.[BH4-].[Na+]>CO>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22])[CH2:13][CH2:12]1)=[O:10])[C:2... | CCOC(=O)CCCCC1CCN(C(=O)OCc2ccccc2)CC1 | null | null | [BH4-] | [Na+] | 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 | null | To a stirred mixture of ethyl 5-(1-benzyloxycarbonyl-4-piperidyl)valerate (26.8 g), tetrahydrofuran (200 ml) and sodium borohydride (13.4 g) is added dropwise methanol (40 ml) for 1.5 hours at 70°-80° C. After the addition is complete, the mixture is refluxed for 2 hours with stirring. After evaporation of solvent, the... | O=C(OCc1ccccc1)N1CCC(CCCCCO)CC1 | null | 97.6 | null |
1,094,033 | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | null | 2011-01-01T00:09:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:21][O:22][CH:23]([C:25]3[CH:26]=[C:27]([C:35]([F:38])([F:37])[F:36])[CH:28]=[C:29]4[C:33]=3[N:32](C)[CH:31]=[CH:30]4)[CH3:24])[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(=O)=O>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([... | CC(OCC1(c2ccc(F)cc2)CCN(C(=O)OC(C)(C)C)CC1)c1cc(C(F)(F)F)cc2ccn(C)c12 | null | null | O=C=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Enantiomers A and B of tert-butyl 4-(4-fluorophenyl)-4-((1-(1-methyl-5-(trifluoromethyl)-1H-indol-7-yl)ethoxy)methyl)piperidine-1-carboxylate. (±)-tert-butyl 4-(4-fluorophenyl)-4-((1-(1-methyl-5-(trifluoromethyl)-1H-indol-7-yl)ethoxy)methyl)piperidine-1-carboxylate (derived from tert-Butyl 4-(4-fluorophenyl)-4-((1-(5-(... | CC(OCC1(c2ccc(F)cc2)CCN(C(=O)OC(C)(C)C)CC1)c1cc(C(F)(F)F)cc2cc[nH]c12 | null | null | null |
1,368,693 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | [F:1][C:2]([F:39])([F:38])[C:3]1[CH:4]=[C:5]([N:13]([CH3:37])[C:14]([N:16]([CH3:36])[C@@H:17]2[C@@H:21]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18]2)=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[ClH:40].CC(O)C>>[ClH:40].[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6... | CN(C(=O)N(C)[C@H]1CN(C(=O)OC(C)(C)C)C[C@@H]1c1ccc(F)cc1)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)O | null | null | null | null | null | null | null | null | null | null | 50 | 2 | To the compound (0.30 g) obtained in Example 139 was added 2N hydrogen chloride/2-propanol (5 mL), and the mixture was stirred at 50° C. for 2 hr. The reaction mixture was concentrated under reduced pressure to give the title compound (0.23 g, 87%) as a white powder. | CN(C(=O)N(C)[C@H]1CNC[C@@H]1c1ccc(F)cc1)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 | null | 87 | null |
1,240,806 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [Cl:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]([CH3:25])[C:12]3[CH:16]([CH2:17][C:18]([O:20]CC)=[O:19])[O:15][B:14]([OH:23])[C:13]=3[CH:24]=2)[CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO.C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]([CH3:25])[C:12]3[CH:16]([CH2:17][C:18]([OH:20])=[O:19])[O:15][B:14]([OH:23])[C:1... | CCOC(=O)CC1OB(O)c2cc(Oc3cccc(Cl)n3)cc(C)c21 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 2 | To a solution of ethyl 2-(6-(6-chloropyridin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate in MeOH/THF (6 mL, 1:1) was added aqueous NaOH solution (100 mg in 1.5 mL of water). After stirring at room temperature for two hours, the reaction mixture was evaporated and then acidified to pH 3 usi... | Cc1cc(Oc2cccc(Cl)n2)cc2c1C(CC(=O)O)OB2O | null | null | null |
1,729,375 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | [CH2:1]([C@@H:8]([CH2:12][CH2:13][C@H:14]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:15](=[O:31])[NH:16][C@@H:17]1[CH2:23][CH2:22][CH2:21][CH2:20][N:19]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]1=[O:30])[C:9]([OH:11])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:39][C@H:40]1[CH2:46][CH2:45... | N#C[C@@H]1CCC[C@@H]2SCC[C@H](N)C(=O)N12 | O=C(O)[C@H](CC[C@H](Cc1ccccc1)C(=O)N[C@@H]1CCCCN(c2ccccc2)C1=O)Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | (2R,5R)-2,5-Dibenzyl-N1-((4S,7S,10aS)-7-cyano-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)-N6-((S)-2-oxo-1-phenylazepan-3-yl)hexanediamide was synthesized as described in General Procedure H using Intermediate 24 (10 mg, 0.020 mmol) and Intermediate 36 (6.1 mg, 0.023 mmol) to give a white solid (8.0 mg, 57% yiel... | N#C[C@@H]1CCC[C@@H]2SCC[C@H](NC(=O)[C@H](CC[C@H](Cc3ccccc3)C(=O)N[C@H]3CCCCN(c4ccccc4)C3=O)Cc3ccccc3)C(=O)N12 | null | null | null |
214,840 | ord_dataset-5ebf3d05077a4f7fb91a1cd9bdc504d2 | null | 1990-01-01T00:09:00 | true | [OH:1][C:2]1[CH:7]=[C:6]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])[C:5]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:4][C:3]=1[C:20]([CH3:22])=[O:21].[C:23](OCC)(=O)[C:24]([O:26][CH2:27][CH3:28])=[O:25].[H-].[Na+].Cl>C(O)C>[CH2:27]([O:26][C:24]([C:23]1[O:1][C:2]2[CH:7]=[C:6]([NH:8][S:9]([CH3:12])(=[O:11])=[O:... | CCOC(=O)C(=O)OCC | CC(=O)c1cc(Oc2ccccc2)c(NS(C)(=O)=O)cc1O | null | Cl | [H-] | [Na+] | 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 | 80 | 0.17 | 5.0 g of methyl 2-hydroxy-4-methylsulfonylamino-5-phenoxyphenyl ketone was suspended in 85 ml of ethanol. Thereto was added 4.5 ml of diethyl oxalate. Further, 3.1 g of sodium hydride (purity: 60%) was added thereto in portions in 10 minutes. The mixture was refluxed for 1.5 hours. The reaction mixture was introduced i... | CCOC(=O)c1cc(=O)c2cc(Oc3ccccc3)c(NS(C)(=O)=O)cc2o1 | null | 56 | null |
323,612 | ord_dataset-24ad29d930104afea313b6c3bd11099e | null | 1996-01-01T00:01:00 | true | [Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=O)[N:7]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][C:8]3=[N:9]2)=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:27])=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[S:27])[N:7]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][C:8]3=[N:9]2)=[CH:4][CH:3]=1 | COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1 | O=c1c2ccc(Cl)cc2nc2n1CCCCC2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | 10 g of 3-chloro-7,8,9,10-tetrahydroazepino[2,1-b]quinazolin-12(6H)-one was treated with 15 g of Lawesson's reagent in toluene at reflux under nitrogen, until the starting material was consumed, as checked by TLC, using chloroform as eluent (24 hours). The mixture was concentrated in vacuo and chromatographed on silica... | S=c1c2ccc(Cl)cc2nc2n1CCCCC2 | null | null | null |
1,157,420 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | [C:1]([O:5][C:6](=[O:17])[CH2:7][C@@H:8]([OH:16])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])([CH3:4])([CH3:3])[CH3:2].I[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>>[C:1]([O:5][C:6](=[O:17])[C@@H:7]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C@@H:8]([OH:16])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13... | CCCCCCC[C@H](O)CC(=O)OC(C)(C)C | CCCCCCI | null | null | null | null | null | null | null | 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 target compound (2.20 g, 41%) was obtained in the same manner as in Production Example C-1, except that the (S)-3-hydroxydecanoic acid t-butyl ester (4.00 g, 16.4 mmol) obtained in Production Example B-6 and 1-iodohexane (5.20 g, 24.5 mmol) were used. | CCCCCCC[C@H](O)[C@H](CCCCCC)C(=O)OC(C)(C)C | null | null | null |
830,889 | ord_dataset-47bd90bf5ec74fcd99ce250a56e18c8f | null | 2008-01-01T00:07:00 | true | C(OC([N:8]1[CH2:17][CH2:16][C:15]2[C:11](=[C:12](OS(C(F)(F)F)(=O)=O)[N:13]([CH:18]3[CH2:22][CH2:21][C:20]([CH3:24])([CH3:23])[CH2:19]3)[N:14]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[F:33][C:34]1[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=1>>[CH3:24][C:20]1([CH3:23])[CH2:21][CH2:22][CH:18]([N:13]2[C:12]([C:37]3[CH:38]=[CH:39][C:... | CC1(C)CCC(n2nc3c(c2OS(=O)(=O)C(F)(F)F)CCN(C(=O)OC(C)(C)C)CC3)C1 | OB(O)c1ccc(F)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound (52.6 mg) was prepared as in Example 177, Steps C and D, using 201.7 mg of 2-(3,3-dimethyl-cyclopentyl)-3-trifluoromethanesulfonyloxy-4,5,7,8-tetrahydro-2H-1,2,6-triaza-azulene-6-carboxylic acid tert-butyl ester (Example 221, Step A) and 180 mg of 4-fluorophenylboronic acid. MS (ESI): exact mass calc... | CC1(C)CCC(n2nc3c(c2-c2ccc(F)cc2)CCNCC3)C1 | null | 38.4 | null |
47,315 | ord_dataset-6d529f04a1724b5d85dcc290cf4c38bb | null | 1978-01-01T00:10:00 | true | [C:1]1([NH:7][C:8](OC2C(O)=C(C3C=CC=CC=3)S(=O)(=O)C=2C2C=CC=CC=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>ClC1C=CC=CC=1Cl>[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1 | O=C(Nc1ccccc1)OC1=C(c2ccccc2)S(=O)(=O)C(c2ccccc2)=C1O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Clc1ccccc1Cl | null | null | null | null | null | null | null | null | null | null | null | null | 2.1 g of 3-(phenylcarbamyloxy)-4-hydroxy-2,5-diphenylthiophene-1,1-dioxide in 50 ml of o-dichlorobenzene are heated at 150° C. for 2 hours. The phenyl isocyanate formed is then distilled off under reduced pressure produced by a water pump. | O=C=Nc1ccccc1 | null | null | null |
541,343 | ord_dataset-49124ff635234889bd8dcfe87f4f9013 | null | 2002-01-01T00:04:00 | true | Br[C:2]1[C:10]2[O:9][C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])=[N:7][C:6]=2[CH:5]=[C:4]([Cl:18])[CH:3]=1.[CH3:19][CH:20]([OH:23])[C:21]#[CH:22].C(N(CC)CC)C>C1(C)C=CC=CC=1.[Cu]I>[Cl:18][C:4]1[CH:3]=[C:2]([C:22]#[C:21][CH:20]([OH:23])[CH3:19])[C:10]2[O:9][C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=... | C#CC(C)O | Clc1cc(Br)c2oc(-c3ccccc3Cl)nc2c1 | null | [Cu]I | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | 15.98 g (46.6 mmol) of 7-bromo-5-chloro-2-(2-chlorophenyl)-benzoxazole and 5 5.48 ml (69.9 mmol) of (±)-3-butyn-2-ol were heated for 6 h at 90-5° C. in 47 ml of toluene with 47 ml of triethylamine, 163.5 mg (233 μmol) of bis-triphenylphosphine-palladium(II)-dichloride and 8.9 mg (46.6 23 μmol) of copper(I) iodide. The ... | CC(O)C#Cc1cc(Cl)cc2nc(-c3ccccc3Cl)oc12 | null | null | null |
22,176 | ord_dataset-19b9e29d593f4660ab77c07b459da9bb | null | 1977-01-01T00:04:00 | true | Cl.[NH2:2][C@H:3]1[C:18](=[O:19])[N:5]2[C:6]([C:15]([O-:17])=[O:16])=[C:7]([CH:10]3[CH2:14][CH2:13][CH2:12][CH2:11]3)[CH2:8][S:9][C@H:4]12>[N+](C)([O-])=O>[NH2:2][C@H:3]1[C:18](=[O:19])[N:5]2[C:6]([C:15]([OH:17])=[O:16])=[C:7]([CH:10]3[CH2:11][CH2:12][CH2:13][CH2:14]3)[CH2:8][S:9][C@H:4]12 | N[C@H]1C(=O)N2C(C(=O)[O-])=C(C3CCCC3)CS[C@H]12 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C[N+](=O)[O-] | null | null | null | null | null | null | null | null | null | null | 0 | null | A current of gaseous hydrogen chloride was passed through a mixture of 585 mg of the product of Step G and 12 ml of nitromethane cooled to 0° C for 15 minutes and the mixture was evaporated to dryness under reduced pressure. The residue was taken up in ether and the crystals were recovered by vacuum filtration. The res... | N[C@H]1C(=O)N2C(C(=O)O)=C(C3CCCC3)CS[C@H]12 | null | null | null |
1,752,995 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [Cl:1][C:2]1[C:10]([CH3:11])=[N:9][C:8]2[N:4]([N:5]=[C:6]3[CH2:14][N:13]([C:15]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[O:23][CH2:24][CH2:25][NH:26][CH3:27])=[O:16])[CH2:12][C:7]3=2)[C:3]=1[CH3:28].[C:29]([Si:33]([CH3:39])([CH3:38])[O:34][CH2:35][CH:36]=O)([CH3:32])([CH3:31])[CH3:30].C(O[BH-](OC(=O)C)OC(=O)C)(=O)... | CC(C)(C)[Si](C)(C)OCC=O | CNCCOc1ccccc1C(=O)N1Cc2nn3c(C)c(Cl)c(C)nc3c2C1 | 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 | ClCCCl | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of Example 144 (100 mg; 0.25 mmol; 1 eq.), (tert-butyl-dimethyl-silanyloxy)-acetaldehyde (87 mg; 0.50 mmol; 2 eq.) and sodium triacetoxyborohydride (58 mg; 0.28 mmol; 1.1 eq.) in DCE (10 mL) was stirred at 70° C. for 1 hour. The solution was washed with 0.1M NaOH (2×), dried over sodium sulfate and concentrat... | Cc1nc2c3c(nn2c(C)c1Cl)CN(C(=O)c1ccccc1OCCN(C)CCO[Si](C)(C)C(C)(C)C)C3 | null | 32.2 | null |
137,580 | ord_dataset-3fa0a6b7d51b4fc6a5380aa0d03ac884 | null | 1985-01-01T00:12:00 | true | [N:1]1([CH2:7][CH2:8][CH2:9][OH:10])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[CH2:12][C:13]([N:15]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[C:19](=[O:26])[NH:18][C:17]2[CH:27]=[CH:28][CH:29]=[N:30][C:16]1=2)=[O:14].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[OH:10][CH2:9][CH2:8][CH2:7][N:1]1[CH2:6][CH2:5][N:4]([CH2:12][C:13](... | O=C1Nc2cccnc2N(C(=O)CCl)c2ccccc21 | OCCCN1CCNCC1 | null | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | 1-Piperazinepropanol (8 g) was added to a suspension of 11-(2-chloroacetyl)-5,11-dihydro-6H-pyrido-[2,3-b][1,4]benzodiazepin-6-one (15 g) and anhydrous sodium carbonate (15 g) in absolute ethanol (250 ml). | O=C1Nc2cccnc2N(C(=O)CN2CCN(CCCO)CC2)c2ccccc21 | null | null | null |
77,731 | ord_dataset-0c37e633e9814a6e886187796cacf216 | null | 1981-01-01T00:03:00 | true | [Mg].[CH2:2](Br)[C:3]#[CH:4].[Cl:6][CH2:7][C:8](=[O:13])[CH2:9][CH2:10][CH2:11][CH3:12].[Cl-].[NH4+]>CCOCC>[Cl:6][CH2:7][C:8]([OH:13])([CH2:9][CH2:10][CH2:11][CH3:12])[CH2:4][C:3]#[CH:2] | C#CCBr | CCCCC(=O)CCl | null | [Cl-] | [Mg] | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | 25 | 1 | To a stirred suspension of 2.1 g. of magnesium and 20 mg. of mercuric chloride in 25 ml. of ether is added 0.8 ml. of propargyl bromide. After a few minutes of vigorous stirring, to this is added a mixture of 10.75 g. of 1-chloro-2-hexanone and 7.2 ml. of propargyl bromide in 25 ml. of ether, at such a rate that the re... | C#CCC(O)(CCl)CCCC | null | null | null |
5,838 | ord_dataset-a5669edbeffe43bf8514c1bfede8f882 | null | 1976-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]=[C:12]([N+]([O-])=O)[CH3:13].C(O)(=[O:19])C.S(=O)(O)[O-].[Na+]>CC(C)=O.O.[Fe]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C:12](=[O:19])[CH3:13] | CC(=Cc1c[nH]c2ccc(Cl)cc12)[N+](=O)[O-] | CC(=O)O | null | [Fe] | O=S([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(C)=O | null | null | null | null | null | null | null | null | null | 20 | 4 | A mixture of 104g of 5-chloro-3-(2-nitropropen-1-yl)indole, 115g of powdered iron and 6g of ferric chloride dissolved in 1250 ml of acetone is brought to reflux. Heating ceases as soon as reflux commences and a solution of 265 ml of acetic acid in 800 ml of water is added over 30 minutes. The reaction mixture is again ... | CC(=O)Cc1c[nH]c2ccc(Cl)cc12 | null | null | null |
641,753 | ord_dataset-ce71a906ea9c4399a2014cbaaff88c8f | null | 2004-01-01T00:07:00 | true | [C:1]([C@@H:3]([NH:8][C:9]([C@@H:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]1[NH:17][C:18]([C:20]1[N:21]([CH2:29][CH2:30][CH2:31]Cl)[C:22]2[C:27]([CH:28]=1)=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])=[O:10])[CH2:4][CH:5]([CH3:7])[CH3:6])#[N:2].[I-].[Na+].C(#N)C.[NH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1>O>[C:1](... | C1CCNCC1 | CC(C)C[C@@H](C#N)NC(=O)[C@@H]1CCCC[C@@H]1NC(=O)c1cc2ccccc2n1CCCCl | null | [I-] | [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 | 50 | 24 | To 1-(3-chloro-propyl)-1H-indole-2-carboxylic acid [(1S,2R)-2-((S)-1-cyano-3-methyl-butylcarbamoyl)cyclohexyl]-amide (200 mg, 0.44 mmol) was added sodium iodide (66 mg, 0.44 mmol), acetonitrile (2 mL), and piperidine (0.1 mL, 1.3 mmol). The reaction mixture was heated to 50° C. and stirred for 24 hrs. Water (15 mL) was... | CC(C)C[C@@H](C#N)NC(=O)[C@@H]1CCCC[C@@H]1NC(=O)c1cc2ccccc2n1CCCN1CCCCC1 | null | 67.4 | null |
267,415 | ord_dataset-134cf2fa32ab464880d75db06c38f35a | null | 1993-01-01T00:05:00 | 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]([CH3:53])=[CH:43][CH:44]2[CH2:49][... | O=C(Cl)C1CC1 | CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(N)C(OC)C3)C(C)C(O)CC1=O)C(C)CC2OC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | ClCCl | null | null | null | null | null | null | null | null | null | 0 | 0.5 | A solution of 32 mg of 17-ethyl-1,14-dihydroxy-12-[2'-(4"-amino-3"-methoxycyclohexyl)-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 (from Example 3) in dry methylene chloride (0.4 ml) was cooled to 0° C. To this solution was added trieth... | CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(NC(=O)C4CC4)C(OC)C3)C(C)C(O)CC1=O)C(C)CC2OC | null | 57.5 | null |
589,984 | ord_dataset-7a74d48eeefd45aba53e7258f3ae067a | null | 2003-01-01T00:04:00 | true | Br[CH2:2][C:3]([C:5]1[CH:6]=[C:7]([C:11]2[CH2:17][C:16](=[O:18])[NH:15][C:14]3[CH:19]=[C:20]([Cl:26])[C:21]([N:23]([CH3:25])[CH3:24])=[CH:22][C:13]=3[N:12]=2)[CH:8]=[CH:9][CH:10]=1)=O.C(C([O:33][CH2:34][C:35]([NH2:37])=[S:36])=O)(C)(C)C>CCO.CCOC(C)=O>[Cl:26][C:20]1[C:21]([N:23]([CH3:24])[CH3:25])=[CH:22][C:13]2[N:12]=[... | CN(C)c1cc2c(cc1Cl)NC(=O)CC(c1cccc(C(=O)CBr)c1)=N2 | CC(C)(C)C(=O)OCC(N)=S | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 80 | 0.33 | A mixture of 4-(3-bromoacetyl-phenyl)-8-chloro-7-dimethylamino-1,3-dihydro-benzo[b][1,4]diazepin-2-one (0.22 g) and 2-(tert.-butylcarbonyl-oxy)thioacetamide (0.11 g) in EtOH (3 mL) was heated at 80° C. for 0.5 h. The solution was diluted with AcOEt, washed with sat. NaHCO3 solution and with brine, dried and evaporated.... | CN(C)c1cc2c(cc1Cl)NC(=O)CC(c1cccc(-c3csc(CO)n3)c1)=N2 | null | 416.6 | null |
461,251 | ord_dataset-5ca9db262dd24c5a9315cdc8ef055b7e | null | 2000-01-01T00:04:00 | true | [CH2:1]([N:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1)[CH3:2].Cl[C:10]1[N:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][CH:11]=1>O>[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:10]2[N:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][CH:11]=2)[CH2:5][CH2:4]1)[CH3:2] | CCN1CCNCC1 | COC(=O)c1ccc(Cl)nc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | null | null | To 100 g of 1-ethylpiperazine warmed to 80° C. was added at 80-100° C. with stirring 50 g of methyl 6-chloropyridine-3-carboxylate. To the reaction solution was added 0.5 1 of water and the mixture was stirred. The crystal thus precipitated out was recovered by filtration, dried under reduced pressure to afford 68.8 g ... | CCN1CCN(c2ccc(C(=O)OC)cn2)CC1 | null | 94.7 | null |
797,428 | ord_dataset-a2d74266062e4398bc26c4f876903ab8 | null | 2007-01-01T00:11:00 | true | [CH2:1]([O:3][C@@H:4]([C@H:9](O)[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18](CNC)[CH:17]=2)=[CH:12][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])[CH3:2].[CH2:26]([N:28](CC)[CH2:29]C)C>FC(F)(F)C(O)=O>[CH2:1]([O:3][C@@H:4]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:... | CCO[C@H](C(=O)OC)[C@H](O)c1ccc(-c2cccc(CNC)c2)cc1 | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | 25 | 48 | 19.6 g of the crude product methyl (2S,3R)-2-ethoxy-3-hydroxy-3-(3′-methylaminomethylbiphenyl-4-yl)propionate are dissolved in 200 ml of trifluoroacetic acid and 41.7 ml (297 mmol) of triethylamine are added. The reaction medium is stirred at room temperature for 48 hours and then extracted with ethyl acetate. The orga... | CCO[C@@H](Cc1ccc(-c2ccccc2)cc1CNC)C(=O)OC | null | 10 | null |
766,498 | ord_dataset-7a8649d55889427e85b208ae89475895 | null | 2007-01-01T00:04:00 | true | [N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=O.[NH2:9][CH:10]([P:19](=[O:26])([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22])[P:11](=[O:18])([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:9][CH:10]([P:11](=[O:18])([O:12][CH2:13][... | CCOP(=O)(OCC)C(N)P(=O)(OCC)OCC | O=Cc1ccccn1 | null | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | 12 | A mixture of 2-pyridinecarboxaldehyde (1.23 g, 11.5 mmol), tetraethyl aminomethylenediphosphonate (3.0 g, 9.9 mmol) and a catalytic amount of p-toluenesulfonic acid dissolved in 10 ml toluene was heated to reflux for 7 h. Toluene was evaporated and the residue dissolved in ethanol was submitted for 12 h to catalytic hy... | CCOP(=O)(OCC)C(NCc1ccccn1)P(=O)(OCC)OCC | null | null | null |
1,152,858 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | [OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[O:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15].[CH2:16]([O:18][C:19]([CH:21]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:20])[CH3:17]>O1CCCC1>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH:21][C:19]([O:18][CH2:16][CH3:17])=[O:20])=[CH:4][C:3]=1[O:10][CH2:11][CH2:12][CH2:13]... | COCCCOc1cc(C=O)ccc1O | CCOC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1 | 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 | 8 | 4-hydroxy-3-(3-methoxypropoxy)benzaldehyde (15 g, 71.3 mmol) was dissolved in tetrahydrofuran (142 mL) and (ethoxycarbonylmethylene)triphenylphosphorane (24.8 g, 71.3 mmol) was added at room temperature portionwise. The mixture was then stirred overnight. The solvents were evaporated under reduced pressure and the resi... | CCOC(=O)C=Cc1ccc(O)c(OCCCOC)c1 | null | 80.1 | null |
1,015,999 | ord_dataset-f024e9664ab64906a71a2ff6004cb3d0 | null | 2010-01-01T00:12:00 | true | [CH2:1]([N:3]1[CH2:8][CH:7]=[C:6]([C:9]2[C:10]([F:16])=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=2)[CH2:5][CH2:4]1)[CH3:2].Cl>[Pd].CO>[CH2:1]([N:3]1[CH2:8][CH2:7][CH:6]([C:9]2[C:10]([F:16])=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=2)[CH2:5][CH2:4]1)[CH3:2] | CCN1CC=C(c2cccc(O)c2F)CC1 | null | null | [Pd] | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | Preparation according to Example 2: 3-(1-ethyl-1,2,3,6-tetrahydropyridin-4-yl)-2-fluorophenol (1.1 g, 4.97 mmol), methanol (20 ml), palladium on carbon (0.26 g) and hydrochloric acid (0.2 ml, conc). Yield: 1.1 g. MS m/z (relative intensity, 70 eV) 223 (M+, 32), 222 (17), 209 (13), 208 (bp) 84 (20). | CCN1CCC(c2cccc(O)c2F)CC1 | null | null | null |
899,462 | ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded | null | 2009-01-01T00:08:00 | true | [CH:1]1([CH:6]2[CH2:8][C:7]2([C:12]2[S:13][C:14]([S:17](=[O:24])(=[O:23])/[N:18]=[CH:19]\[N:20]([CH3:22])[CH3:21])=[CH:15][CH:16]=2)[C:9]([OH:11])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:25][C:26]1[S:27][CH:28]=[CH:29][N:30]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C>>[S:27]1[CH:28]=[CH:29][N:30]=[C:... | CN(C)/C=N\S(=O)(=O)c1ccc(C2(C(=O)O)CC2C2CCCC2)s1 | Nc1nccs1 | null | CN(C)C(On1nnc2ccccc21)=[N+](C)C | F[B-](F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | null | According to method 16h was used (±)-(Z)-2-cyclopentyl-1-[5-(dimethylaminomethylene-sulfamoyl)-thiophen-2-yl]-cyclopropanecarboxylic acid (65 mg, max. 0.344 mmol), 2-amino-thiazole (19 mg, 0.188 mmol), TBTU (60 mg, 0.188 mmol) and triethylamine (57 μL, 0.402 mmol) to give 43 mg of purified product. MS (m/e): 453.0 (M+H... | CN(C)/C=N\S(=O)(=O)c1ccc(C2(C(=O)Nc3nccs3)CC2C2CCCC2)s1 | null | 50.5 | null |
1,373,799 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | [Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[N:6][CH:7]=1.[C:10](N1C=CN=C1)(N1C=CN=C1)=[O:11].O>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[NH:9][C:10](=[O:11])[NH:8][C:5]2=[N:6][CH:7]=1 | O=C(n1ccnc1)n1ccnc1 | Nc1cc(Br)cnc1N | 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 | 25 | 8 | 5-Bromopyridine-2,3-diamine (2.45 g) was dissolved in THF (25 mL) and 1,1′-carbonyldiimidazole (2.54 g, 1.2 eq) was added. The reaction was stirred at room temperature under nitrogen gas overnight. Water was then added to the mixture and the product was collected by filtration. The solid was dried under vacuum deliveri... | O=c1[nH]c2cc(Br)cnc2[nH]1 | null | 92.2 | null |
1,518,062 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | [C:1]1([O:7][CH:8]([CH2:10][O:11][CH:12]([CH2:14][OH:15])C)C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:16](O)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCCCCCC>S(=O)(=O)(O)O.O>[C:16]([O:15][CH2:14][CH2:12][O:11][CH2:10][CH2:8][O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=... | O=C(O)c1ccccc1 | CC(CO)OCC(C)Oc1ccccc1 | null | O=S(=O)(O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCCCCCC | null | null | null | null | null | null | null | null | null | 115 | null | In a 2-L one-neck flask equipped with a magnetic stirrer, a heating mantle, and a Dean-Stark trap connected to a nitrogen purged condenser were placed 517.5 g dipropylene glycol phenyl ether technical grade containing a total hydroxyl content of 3.0 moles, 363.3 g (2.97 mole) benzoic acid, 300 ml heptane, and 20 drops ... | O=C(OCCOCCOc1ccccc1)c1ccccc1 | null | null | null |
1,616,109 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [F:1][C:2]1[CH:28]=[CH:27][CH:26]=[CH:25][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]2[N:19]=[C:18](O)[C:17]([C:21]([O:23][CH3:24])=[O:22])=[CH:16][N:15]=2)=[N:6]1.P(Cl)(Cl)([Cl:31])=O.CCN(C1C=CC=CC=1)CC>>[Cl:31][C:18]1[C:17]([C:21]([O:23][CH3:24])=[O:22])=[CH:16][N:15]=[C:14]([C:7]2[C:8]3... | O=P(Cl)(Cl)Cl | COC(=O)c1cnc(-c2nn(Cc3ccccc3F)c3ncccc23)nc1O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | 6.54 g (17.2 mmol) of methyl 2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4-hydroxypyrimidine-5-carboxylate (example 105A) were taken up in 26.5 ml (284 mmol) of phosphoryl chloride. Then 5.95 g (34.5 mmol) of diethylaniline were added and the mixture was reacted at 90° C. for 60 min. After cooling, the precip... | COC(=O)c1cnc(-c2nn(Cc3ccccc3F)c3ncccc23)nc1Cl | null | null | null |
209,639 | ord_dataset-ac1c7aa04d6c4e588e723e3e05721681 | null | 1990-01-01T00:05:00 | true | [C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]=[CH2:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])(O)=O.[Na+].O.[Br:18][C:19](Br)=[N:20][OH:21]>C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[O:21][N:20]=[C:19]([Br:18])[CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2] | C=CCNC(=O)OC(C)(C)C | ON=C(Br)Br | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | To a solution of N-tert-butoxycarbonyl allyl amine, 20 gm, in 700 ml of ethyl acetate and containing 65 gm of NaHCO3 and 50 ml of water, was added portion-wise 80 gm of dibromoformaldoxime at room temperature with vigorous stirring. After completion of the reaction, the organic portion was washed with water (2×100 ml),... | CC(C)(C)OC(=O)NCC1CC(Br)=NO1 | null | null | null |
541,448 | ord_dataset-49124ff635234889bd8dcfe87f4f9013 | null | 2002-01-01T00:04:00 | true | [N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[CH2:11]([O:13][C:14](=[O:28])[CH:15]([CH2:19][C:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:16](=O)[CH3:17])[CH3:12].CC1C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH2:11]([O:13][C:14]([C:15]1[CH:19]=[C:20]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]... | CCOC(=O)C(CC(=O)c1ccccc1)C(C)=O | Nc1ccccc1[N+](=O)[O-] | null | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | o-Nitroaniline (15 mmol, 2.1 g), 3-oxo-2-(2-oxo-2-phenyl-ethyl)-butyric acid ethyl ester (15 mmol, 3.7 g), and tosic acid (0.1 g) were combined in ethanol, then heated under reflux. The resulting oil was purified over three silica gel columns to yield the named product, 1H-NMR (CDCl3, ppm): 1.36 t (3H), 2.36 s (3H), 4.... | CCOC(=O)c1cc(-c2ccccc2)n(-c2ccccc2[N+](=O)[O-])c1C | null | null | null |
1,121,881 | ord_dataset-285df12e34cd46e993e3c8ebc3a8962a | null | 2012-01-01T00:01:00 | true | [F:1][C:2]([F:19])([F:18])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:14][C:13]([C:15](=[O:17])[CH3:16])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.[Cl:20][C:21]1[C:28]([Cl:29])=[C:27]([OH:30])[CH:26]=[CH:25][C:22]=1[CH:23]=O>>[Cl:20][C:21]1[C:28]([Cl:29])=[C:27]([OH:30])[CH:26]=[CH:25][C:22]=1[CH:23]=[CH:16][C:15]([C:13]1[S:14][C:1... | CC(=O)c1ccc(-c2ccc(OC(F)(F)F)cc2)s1 | O=Cc1ccc(O)c(Cl)c1Cl | null | null | null | null | null | null | null | 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-(2,3-Dichloro-4-hydroxyphenyl)-1-(5-(4-(trifluoromethoxy)phenyl)thien-2-yl)prop-2-en-1-one is prepared from 1-(5-(4-(trifluoromethoxy)phenyl)thien-2-yl)-ethanone and 2,3-dichloro-4-hydroxybenzaldehyde according to general procedure B. The evaporation residue is crystallized from acetonitrile. | O=C(C=Cc1ccc(O)c(Cl)c1Cl)c1ccc(-c2ccc(OC(F)(F)F)cc2)s1 | null | null | null |
758,697 | ord_dataset-1b0cd79134f0450eaac8396a4f956c30 | null | 2007-01-01T00:02:00 | true | FC(F)(F)S([O:6][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8])(=O)=O.[CH3:16][O:17][C:18]1[N:23]=[CH:22][C:21]([N:24]2[C:28]([C:29]3[CH:34]=[CH:33][C:32](O)=[CH:31][CH:30]=3)=[CH:27][C:26]([O:36][CH2:37][C:38]([F:41])([F:40])[F:39])=[N:25]2)=[CH:20][CH:19]=1.N1C=CC=CC=1>C(Cl)Cl>[F:13][C:10]([F:11])([F:12])[S:7]([O:6... | O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F | COc1ccc(-n2nc(OCC(F)(F)F)cc2-c2ccc(O)cc2)cn1 | null | null | 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 | null | 1 | A solution of trifluoromethanesulfonic anhydride (207 μl) in CH2Cl2 (1 mg) was added to a solution of 4-[1-(6-methoxy-3-pyridinyl)-3-(2,2,2-trifluoroethoxy)-1H-pyrazol-5-yl]phenol (300 mg) and pyridine (199 μl) in CH2C12 (3 ml) under ice-bath cooling. The mixture was stirred at same temperature for 1 hour. The reaction... | COc1ccc(-n2nc(OCC(F)(F)F)cc2-c2ccc(OS(=O)(=O)C(F)(F)F)cc2)cn1 | null | null | null |
1,227,365 | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | null | 2012-01-01T00:11:00 | true | CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[C:23]([SiH2:27][O:28][C:29]([CH3:42])([CH3:41])[C:30]1[CH:31]=[C:32]([CH2:39][OH:40])[CH:33]=[C:34]([N:36]([CH3:38])[CH3:37])[CH:35]=1)([CH3:26])([CH3:25])[CH3:24].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:23]([SiH2:27][O:28][C:29]([CH3:42])([CH3:41])[C:30]1[CH:31]=[C:32]([CH:33]=[C:3... | CN(C)c1cc(CO)cc(C(C)(C)O[SiH2]C(C)(C)C)c1 | null | null | CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21 | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | 0.25 | A suspension of Dess-Martin periodinane (available from Aldrich Chemical Company, Inc., 1001 West Saint Paul Avenue, Milwaukee, Wis. 53233, USA; 538 mg, 1.27 mmol) in methylene chloride (10 mL) was pipetted into a magnetically stirred solution of [3-(tert-butyl-dimethyl-silanyloxymethyl)-5-dimethylamino-phenyl]-methano... | CN(C)c1cc(C=O)cc(C(C)(C)O[SiH2]C(C)(C)C)c1 | null | 64.6 | null |
844,146 | ord_dataset-e2b35e721c2741999b0005d12691f9fe | null | 2008-01-01T00:10:00 | true | Cl[CH2:2][C:3]([NH:5][C:6]1[CH:16]=[CH:15][C:9]2[NH:10][C:11](=[O:14])[CH2:12][O:13][C:8]=2[CH:7]=1)=[O:4].[F:17][C:18]1[CH:30]=[CH:29][C:21]([CH2:22][CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[CH:20][CH:19]=1>C(OCC)C>[F:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:22][CH:23]2[CH2:24][CH2:25][N:26]([CH2:2][C:3]([NH:5][C... | O=C(CCl)Nc1ccc2c(c1)OCC(=O)N2 | Fc1ccc(CC2CCNCC2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | null | null | The title compound is prepared from 2-chloro-N-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-7-yl)-acetamide (Example 153a) and 4-(4-fluoro-benzyl)-piperidine according to the method described in Example 142b. Melting Point: 209-211° C. (diethylether) | O=C(CN1CCC(Cc2ccc(F)cc2)CC1)Nc1ccc2c(c1)OCC(=O)N2 | null | null | null |
1,441,256 | ord_dataset-275a3da8f45f4536ad29727f0ef9ba66 | null | 2014-01-01T00:06:00 | true | [Cl:1][C:2]1[CH:6]=[N:5][N:4]([CH3:7])[C:3]=1[C:8]1[CH:9]=[C:10]([NH2:16])[CH:11]=[CH:12][C:13]=1[O:14][CH3:15].[F:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[N:25]=[C:26]=[O:27]>>[Cl:1][C:2]1[CH:6]=[N:5][N:4]([CH3:7])[C:3]=1[C:8]1[CH:9]=[C:10]([NH:16][C:26]([NH:25][C:19]2[CH:20]=[CH:21][C:22]([F:24])=[CH:2... | COc1ccc(N)cc1-c1c(Cl)cnn1C | O=C=Nc1ccc(F)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 | 3-(4-Chloro-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenylamine was treated with 2,4-difluorophenyl isocyanate in a similar manner as described in Example 1.53, providing 26.7 mg (36%) of Compound 29: LCMS m/z (%)=395 (M+H37Cl, 35), 393 (M+H35Cl, 100). 1H NMR (400 MHz, DMSO-d6) δ: 9.00 (s, 1H), 8.43 (s, 1H), 8.03 (m, J1=12... | COc1ccc(NC(=O)Nc2ccc(F)cc2F)cc1-c1c(Cl)cnn1C | null | 36 | null |
840,711 | ord_dataset-074f86301ec5441ab3b52d902ac06949 | null | 2008-01-01T00:09:00 | true | [F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([C:9]2([C:12](Cl)=[O:13])[CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.[NH2:17][C:18]1[N:23]([C:24]2[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=2)[CH2:22][N:21]=[C:20]2[O:31][CH:32]=[CH:33][C:19]=12>>[NH2:17][C:18]1[N:23]([C:24]2[CH:25]=[CH:26][C:27]([NH:30][C:12]([C:9]3([C:5]4... | O=C(Cl)C1(c2cccc(C(F)(F)F)c2)CC1 | NC1=c2ccoc2=NCN1c1ccc(N)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 compound was prepared following the procedure described in making Example 474, using 1-(3-Trifluoromethyl-phenyl)-cyclopropanecarbonyl chloride as the acid chloride of choice, and 4-Amino-3-(4-aminophenyl)furo[2,3-d]pyrimidine (9) as the diamine of choice. MS(ES) m/e 436 [M+H]+. | NC1=c2ccoc2=NCN1c1ccc(NC(=O)C2(c3cccc(C(F)(F)F)c3)CC2)cc1 | null | null | null |
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