original_index int64 2 1.77M | extracted_from_file stringclasses 489
values | date_of_experiment timestamp[ns]date | grant_date timestamp[ns]date 1976-01-01 00:01:00 2016-01-01 00:09:00 | is_mapped bool 1
class | rxn_str stringlengths 87 6.12k | reactant_000 stringlengths 1 902 | reactant_001 stringlengths 1 902 ⌀ | reactant_002 null | agent_000 stringlengths 1 540 ⌀ | agent_001 stringlengths 1 852 ⌀ | agent_002 stringlengths 1 247 ⌀ | agent_003 null | agent_004 null | agent_005 null | agent_006 null | agent_007 null | agent_008 null | agent_009 null | agent_010 null | agent_011 null | agent_012 null | agent_013 null | agent_014 null | agent_015 null | agent_016 null | solvent_000 stringclasses 446
values | solvent_001 stringclasses 405
values | solvent_002 null | solvent_003 null | solvent_004 null | solvent_005 null | solvent_006 null | solvent_007 null | solvent_008 null | solvent_009 null | solvent_010 null | temperature float64 -230 30.1k ⌀ | rxn_time float64 0 2.16k ⌀ | procedure_details stringlengths 8 24.5k | product_000 stringlengths 1 484 | product_001 null | yield_000 float64 0 90,205,156,600B ⌀ | yield_001 float64 0 100M ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
1,753,739 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:19][CH3:20])[C:12]2([C:15]([O:17]C)=[O:16])[CH2:14][CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.O.O[Li].O>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:19][CH3:20])[C:12]2([C:15]([OH:17])=[O:16])[CH2:14][CH2:13]2)(=[O:9])=[O:10])=[CH:4][CH:3]=1 | CCN(C1(C(=O)OC)CC1)S(=O)(=O)c1ccc(Cl)cc1 | null | null | [Li]O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | O | null | null | null | null | null | null | null | null | null | 25 | 3 | Compound 14B (750 mg, 2.36 mmol) dissolved in THF (10 ml) and water (5 ml) was added with LiOH.H2O (3 equiv., 297 mg) and the reaction was stirred at rt 3 hours. The reaction was concentrated under vacuum. Water was added and 10% HCl till precipitation of the acid. The acid was extracted with ethyl acetate and the orga... | CCN(C1(C(=O)O)CC1)S(=O)(=O)c1ccc(Cl)cc1 | null | 90.7 | null |
1,449,225 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [Br:1][C:2]1[C:3](Br)=[N:4][CH:5]=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].[CH3:14]B(O)O.C(=O)([O-])[O-].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1>[Br:1][C:2]1[C:... | CB(O)O | CCOC(=O)c1cnc(Br)c(Br)c1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 110 | 72 | An oven-dried resealable Schlenk tube was charged with ethyl 5,6-dibromonicotinate (preparation 47b, 1.09 g, 3.5 mmol), methylboronic acid (0.24 g, 4.0 mmol), potassium carbonate (1.46 g, 10.6 mmol) and 1,4-dioxane (27 mL). The Schlenk tube was subjected to three cycles of evacuation-backfilling with argon, and then te... | CCOC(=O)c1cnc(C)c(Br)c1 | null | 48 | null |
716,639 | ord_dataset-c8a367b56b4f406b878f51867b157d19 | null | 2006-01-01T00:06:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1I.[NH:9]1[C:17]2[C:12](=[C:13]([CH2:18][N:19]3[CH2:24][CH2:23][CH:22]([C:25]4[CH:26]=[C:27]([NH:31][C:32](=[O:36])[CH:33]([CH3:35])[CH3:34])[CH:28]=[CH:29][CH:30]=4)[CH2:21][CH2:20]3)[CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10]1>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:9... | CC(C)C(=O)Nc1cccc(C2CCN(Cc3cccc4[nH]ccc34)CC2)c1 | Clc1ccccc1I | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared by Procedure C and Scheme Q1, with CuBr in place of Cu, using 1-chloro-2-iodobenzene and N-{3-[1-(1H-indol-4-ylmethyl)-4-piperidinyl]phenyl}-2-methylpropanamide: ESMS m/e: 486.1 (M+H)+. | CC(C)C(=O)Nc1cccc(C2CCN(Cc3cccc4c3ccn4-c3ccccc3Cl)CC2)c1 | null | null | null |
1,701,518 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [OH:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([C:10]2([C:14]#[N:15])[CH2:13][CH2:12][CH2:11]2)=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl.Br[CH2:27][CH2:28][CH2:29][N:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1>CC#N>[CH3:9][O:8][C:7]1[C:2]([O:1][CH2:27][CH2:28][CH2:29][N:30]2[CH2:34][CH2:33][CH2:32][CH... | BrCCCN1CCCC1 | COc1cc(C2(C#N)CCC2)c([N+](=O)[O-])cc1O | null | Cl | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | 100 | 3 | To a solution of 1-(4-(hydroxyl)-5-methoxy-2-nitrophenyl)cyclobutanecarbonitrile (0.73 g, 2.93 mmol), from Step 3, in MeCN (20 mL) was added potassium carbonate (1.215 g, 8.79 mmol) and 1-(3-bromopropyl)pyrrolidine hydrochloride (1 g, 4.4 mmol) and stirred at 100° C. for 3 hours. The reaction mixture was concentrated, ... | COc1cc(C2(C#N)CCC2)c([N+](=O)[O-])cc1OCCCN1CCCC1 | null | 59.8 | null |
1,673,381 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [BH4-].[Na+].[Br:3][C:4]1[CH:19]=[CH:18][C:7]([CH2:8][N:9]2[CH:14]3[CH2:15][CH2:16][CH:10]2[CH2:11][C:12](=[O:17])[CH2:13]3)=[CH:6][CH:5]=1>CO.O>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]2[CH:14]3[CH2:15][CH2:16][CH:10]2[CH2:11][CH:12]([OH:17])[CH2:13]3)=[CH:18][CH:19]=1 | O=C1CC2CCC(C1)N2Cc1ccc(Br)cc1 | null | null | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CO | null | null | null | null | null | null | null | null | null | null | 0.5 | Sodium borohydride (95 mg, 1.50 mmol) was added to a solution of 8-(4-bromobenzyl)-8-azabicyclo-[3.2.1]octan-3-one (0.22 g, 0.75 mmol) in methanol (10 mL) and the reaction mixture was stirred for 30 minutes. The reaction was diluted with water (10 mL) and extracted into DCM (3×20 mL). The combined organic layer was was... | OC1CC2CCC(C1)N2Cc1ccc(Br)cc1 | null | 90 | null |
67,467 | ord_dataset-b5f1497361c94e5fa55257200189a6a4 | null | 1980-01-01T00:06:00 | true | [Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)=[O:4].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([OH:22])[CH2:20]O)=[CH:15][CH:14]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>O>[Br:1][CH2:2][C:3]1([C:5]2[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=2)[O:22][CH:19]([C:16]2[CH:17]=[CH:18][C:13]([Cl:12])=[... | O=C(CBr)c1ccc(Cl)cc1 | OCC(O)c1ccc(Cl)cc1 | null | Cc1ccc(S(=O)(=O)O)cc1 | 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 | A mixture of 11.7 parts of 2-bromo-4'-chloroacetophenone, 9 parts of 1-(p-chlorophenyl)-1,2-ethanediol, 0.5 parts of p-toluenesulfonic acid and 80 parts of benzene is stirred and refluxed for 2 days with water-separator. The reaction mixture is cooled and washed successively twice with a sodium hydrogen carbonate solut... | Clc1ccc(C2COC(CBr)(c3ccc(Cl)cc3)O2)cc1 | null | null | null |
1,735,507 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | [CH:1]1([C:4]2[N:8]([CH3:9])[C:7]3[CH:10]=[C:11]([N:14]4[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]4=[O:21])[CH:12]=[CH:13][C:6]=3[N:5]=2)[CH2:3][CH2:2]1.[F:22][C:23]1[CH:24]=[C:25]([CH2:30]O)[CH:26]=[CH:27][C:28]=1[F:29].C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1COCC1>[CH:1]1([C:4]2[N:8]([CH3:9])[C:7]3[CH:1... | Cn1c(C2CC2)nc2ccc(-n3ccc(O)cc3=O)cc21 | OCc1ccc(F)c(F)c1 | null | CCCCP(CCCC)CCCC | O=C(N=NC(=O)N1CCCCC1)N1CCCCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 60 | 4 | To a solution of 1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-hydroxypyridin-2(1H)-one (150 mg), (3,4-difluorophenyl)methanol (153 mg) and tributylphosphine (322 mg) in THF (15 ml) was added 1,1′-(azodicarbonyl)dipiperidine (401 mg). The mixture was stirred under sonication at 60° C. for 4 h. The reaction mixture ... | Cn1c(C2CC2)nc2ccc(-n3ccc(OCc4ccc(F)c(F)c4)cc3=O)cc21 | null | 39.1 | null |
1,752,790 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [CH:1]1([CH2:4][N:5]2[C:13]3[CH:12]=[C:11]([C:14]([O:16]C(C)(C)C)=[O:15])[N:10]=[CH:9][C:8]=3[CH:7]=[CH:6]2)[CH2:3][CH2:2]1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH:1]1([CH2:4][N:5]2[C:13]3[CH:12]=[C:11]([C:14]([OH:16])=[O:15])[N:10]=[CH:9][C:8]=3[CH:7]=[CH:6]2)[CH2:2][CH2:3]1 | CC(C)(C)OC(=O)c1cc2c(ccn2CC2CC2)cn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | 50 | 15 | A mixture of tert-butyl 1-(cyclopropylmethyl)-1H-pyrrolo[3,2-c]pyridine-6-carboxylate (2A, 1.1 g, 4.0 mmol) in DCM (5 ml) and TFA (5 ml) was stirred at 50° C. for 15 h. The mixture was concentrated in vacuo to give 1-(cyclopropylmethyl)-1H-pyrrolo[3,2-c]pyridine-6-carboxylic acid (2B, 0.9 g, 4.0 mmol) as a brown oil. T... | O=C(O)c1cc2c(ccn2CC2CC2)cn1 | null | 100 | null |
528,051 | ord_dataset-f027aa93238e424fbbf9bad1c7699adc | null | 2001-01-01T00:12:00 | true | O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[CH3:15][S:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:31])[C:25]([CH3:30])([CH3:29])[C:26]([OH:28])=O)=[CH:19][CH:18]=1>CS(O)(=O)=O>[CH3:29][C:25]1([CH3:30])[C:26](=[O:28])[C:19]2[C:20](=[CH:21][CH:22]=[C:17]([S:16][CH3:15])[CH:18]=2)[NH:23][C:24]1=[O:31] | CSc1ccc(NC(=O)C(C)(C)C(=O)O)cc1 | null | null | CS(=O)(=O)O | O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 70 | 1.5 | Phosphorus pentoxide (4.49 g, 0.032 mol) was added to a stirred solution of N-(4-methylthiophenyl)-2,2-dimethylmalonamic acid (5.0 g, 0.020 mol) in methanesulfonic acid (35 ml). The reaction mixture was warmed to 70° C. and stirred for 90 mins. The product mixture was then cooled to room temperature and poured over ice... | CSc1ccc2c(c1)C(=O)C(C)(C)C(=O)N2 | null | null | null |
779,282 | ord_dataset-8034115bd2ec4d3e95bd3ff7cfde0bde | null | 2007-01-01T00:07:00 | true | [CH:1]1([C:4]2[N:9]3[N:10]=[CH:11][C:12](C(O)=O)=[C:8]3[CH:7]=[C:6]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)[CH:5]=2)[CH2:3][CH2:2]1.CC([O-])=O.[Na+].[I:31]Cl.O>C(O)(=O)C>[CH:1]1([C:4]2[N:9]3[N:10]=[CH:11][C:12]([I:31])=[C:8]3[CH:7]=[C:6]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([... | O=C(O)c1cnn2c(C3CC3)cc(-c3ccc(C(F)(F)F)cc3)cc12 | ClI | null | CC(=O)[O-] | [Na+] | 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 | 23 | 2 | A mixture of 7-cyclopropyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyridine-3-carboxylic acid (example C.28 step 6) (1.03 g, 2.97 mmol) in acetic acid (40 mL) was refluxed for 20 h. Cooled to 23° C., added NaOAc (325 mg, 3.95 mmol) and ICl (2M in HOAc, 1.85 mL, 3.7 mmol) and the mixture was stirred at 23° C. for 2 ... | FC(F)(F)c1ccc(-c2cc(C3CC3)n3ncc(I)c3c2)cc1 | null | null | null |
871,685 | ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | null | 2009-01-01T00:03:00 | true | O[CH:2]([C:5]1[C:13]2[O:12][CH2:11][CH:10]([C:14]3[CH:19]=[CH:18][C:17]([CH:20]([CH3:22])[CH3:21])=[CH:16][CH:15]=3)[C:9]=2[C:8]([CH3:23])=[C:7]([NH:24][C:25](=[O:31])[CH2:26][C:27]([CH3:30])([CH3:29])[CH3:28])[C:6]=1[CH3:32])[CH2:3][CH3:4]>C(OCC)(=O)C.CCCCCC>[CH:20]([C:17]1[CH:18]=[CH:19][C:14]([CH:10]2[C:9]3[C:8]([CH... | CCC(O)c1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CCCCCC | null | null | null | null | null | null | null | null | null | null | null | Using a diastereo mixture of N-(7-(1-hydroxypropyl)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in the synthesis in Examples 30 and 31, the title compound was synthesized in the same manner as in Example 23. Yield: 86%. Melting point: 145-148° C. (ethyl acetate-hexa... | CCCc1c(C)c(NC(=O)CC(C)(C)C)c(C)c2c1OCC2c1ccc(C(C)C)cc1 | null | 86 | null |
1,187,811 | ord_dataset-9cd817a75dfc4fe7ad19d4232772d5ff | null | 2012-01-01T00:07:00 | true | [CH:1]1([CH2:6][CH:7]([C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH2:26][CH2:27]O)(=[O:25])=[O:24])=[CH:19][CH:18]=2)[C:8]2[NH:16][C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.CS(Cl)(=O)=O>ClCCl>[CH:1]1([CH2:6][CH:7]([C:8]2[NH:16][C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[CH... | O=S(=O)(CCO)c1ccc(C(CC2CCCC2)c2cc3cccnc3[nH]2)cc1 | null | null | CS(=O)(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 0 | 0.5 | To a solution of (2-{4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-benzenesulfonyl}-ethanol (prepared as in Example 91, 600 mg, 1.5 mmol) and triethylamine (0.42 ml, 3.0 mmol) in dichloromethane (15 mL) at 0° C. was added a solution of methanesulfonyl chloride (0.18 ml, 2.2 mmol) in dichloromethane. The mix... | C=CS(=O)(=O)c1ccc(C(CC2CCCC2)c2cc3cccnc3[nH]2)cc1 | null | 66.6 | null |
1,297,362 | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | null | 2013-01-01T00:05:00 | true | Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[CH2:10]([NH2:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(#N)C>[C:6]([O:5][C:3](=[O:4])[CH2:2][NH:17][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:9])([CH3:8])[CH3:7] | NCc1ccccc1 | CC(C)(C)OC(=O)CBr | 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 | 2.5 | 0.08 | 40 g (205 mmol, 1 eq.) tert-butyl bromoacetate were dissolved in 200 ml acetonitrile. The solution was cooled to 0-5° C. and 47 g benzylamine (2.14 eq.) in solution in 90 ml acetonitrile were added over 15 min. After 5 min, the reaction mixture was warmed to room temperature and stirred for 3 h (IPC by GC). The resulti... | CC(C)(C)OC(=O)CNCc1ccccc1 | null | 108 | null |
908,421 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | [Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[C:12]#[C:13][C:14]([OH:16])=O.[NH2:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[N:24]=[C:23](C1CCCCN1)[CH:22]=[CH:21]2>ClCCl.CO>[N:24]1([C:23]2[CH:22]=[CH:21][C:20]3[C:25](=[CH:26][CH:27]=[C:18]([NH:17][C:14](=[O:16])[C:13]#[C:12][C:3]4[CH:4... | O=C(O)C#Cc1ccc(C(F)(F)F)cc1Cl | Nc1ccc2nc(C3CCCCN3)ccc2c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | ClCCl | null | null | null | null | null | null | null | null | null | null | null | Prepared analogously to Example 2.3.f. from (2-chloro-4-trifluoromethylphenyl)propynoic acid and 6-amino-2-piperidin-2-ylquinoline. Yield: 170 mg (37.1% of theory); melting point: 176° C.-179° C.; C24H19ClF3N3O (M=457.88); calc.: molecular ion peak (M+H)+: 456/458; found: molecular ion peak (M+H)+: 456/458; Rf value: 0... | O=C(C#Cc1ccc(C(F)(F)F)cc1Cl)Nc1ccc2nc(N3CCCCC3)ccc2c1 | null | null | null |
1,452,135 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [CH2:1]([N:3]([CH2:25][CH3:26])[C:4](=[O:24])[CH2:5][C:6]1[C:7]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)=[N:8][N:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[N:11][C:10]=12)[CH3:2].[Na+].[I-:28]>CO>[CH2:25]([N:3]([CH2:1][CH3:2])[C:4](=[O:24])[CH2:5][C:6]1[C:7]([C:17]2[CH:18]=[CH:19][C:20]([OH:23])=[C:21]... | [I-] | CCN(CC)C(=O)Cc1c(-c2ccc(O)cc2)nn2c(C)cc(C)nc12 | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | 1 | To a solution of 3 (100 mg, 0.28 mmol) in MeOH (15 mL) was added NaI (52 mg, 0.35 mmol) and chloroamine-T hydrate (80 mg, 0.35 mmol). The reaction mixture was stirred for 1 h and then concentrated under vacuum. The residue was purified by column chromatography (CH2Cl2/MeOH, 20:1 (v/v), as eluent) to yield 4 (60 mg, 45%... | CCN(CC)C(=O)Cc1c(-c2ccc(O)c(I)c2)nn2c(C)cc(C)nc12 | null | 44.8 | null |
1,191,838 | ord_dataset-4e81c470cc3b429faf5e1caa50f70a98 | null | 2012-01-01T00:08:00 | true | C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:30])[NH:22][C:23]3[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][CH:24]=3)=[CH:17][C:16]=2[NH:31][C:32]2[C:33]3[CH:41]=[CH:40][C:39]([CH:42]([CH3:44])[CH3:43])=[N:38][C:34]=3[N:35]=[CH:36][N:37]=2)=[CH:10][CH:9]=1)(C)(C)C.FC(F)(F)C(O)=O>C(C... | CC(C)c1ccc2c(Nc3cc(C(=O)Nc4ccc(Br)cc4)ccc3Oc3ccc(NC(=O)OC(C)(C)C)cc3)ncnc2n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | null | null | The product of Example 49D (2.78 g, 4.152 mmol) was treated with trifluoroacetic acid (25 mL) in methylene chloride (25 mL) at room temperature for 30 minutes. The solvents were removed under vacuum by rotary evaporation and the residual oil taken up in ethyl acetate (400 mL) and washed with saturated aqueous sodium bi... | CC(C)c1ccc2c(Nc3cc(C(=O)Nc4ccc(Br)cc4)ccc3Oc3ccc(N)cc3)ncnc2n1 | null | 74.9 | null |
186,522 | ord_dataset-754e10d30fb249229e130865010ab25b | null | 1989-01-01T00:03:00 | true | [CH2:1]([C:4]1[C:17]([OH:18])=[C:16]([Cl:19])[C:15]2[O:14][C:13]3[C:8](=[C:9]([Cl:20])[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:21])[C:6]=2[CH:5]=1)[CH:2]=C.ClC1C=CC=C(C(OO)=O)C=1.C(Cl)(Cl)Cl.[C:37](=[O:40])([O-])[O-:38].[K+].[K+]>O>[Cl:20][C:9]1[C:8]2[C:7](=[O:21])[C:6]3[CH:5]=[C:4]4[CH2:1][CH:2]([C:37]([OH:38])=[O:40])[O:18... | O=C([O-])[O-] | C=CCc1cc2c(=O)c3c(Cl)cccc3oc2c(Cl)c1O | null | O=C(OO)c1cccc(Cl)c1 | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | 25 | 5 | A mixture of 2-allyl-4,8-dichloro-3-hydroxy-9-oxo-9H-xanthene (14 g), m-chloroperbenzoic acid (11 g) and chloroform (1,000 ml) was stirred at room temperature for 5 hours and thereafter left to stand overnight. To the mixture, potassium carbonate (20 g) and water (500 ml) were added and the resulting mixture was extrac... | O=C(O)C1Cc2cc3c(=O)c4c(Cl)cccc4oc3c(Cl)c2O1 | null | 32.7 | null |
712,200 | ord_dataset-c8a367b56b4f406b878f51867b157d19 | null | 2006-01-01T00:06:00 | true | [Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[CH:11][NH:12][C:13]=1[C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[Cl:21].[CH3:22]I.[H-].[Na+]>CN(C=O)C>[Cl:21][C:15]1[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:14]=1[C:13]1[N:12]=[CH:11][N:10]([CH3:22])[C:9]=1[C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7... | CI | Clc1ccc(-c2nc[nH]c2-c2ccc(Cl)cc2Cl)c(Cl)c1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | 3 | To a solution of 4,5-di-(2,4-dichlorophenyl)imidazole (230 mg, 0.65 mmol) from Step B and methyl iodide (0.062 mL, 1.0 mmol) in DMF (5 mL) was added sodium hydride (60% in mineral oil, 52 mg, 1.3 mmol). The reaction was stirred at rt for 3 hr and was then quenched with aq. sodium bicarbonate and extracted twice with et... | Cn1cnc(-c2ccc(Cl)cc2Cl)c1-c1ccc(Cl)cc1Cl | null | null | null |
878,118 | ord_dataset-e1c3af9b105b4af09a5171403bbfc06f | null | 2009-01-01T00:04:00 | true | COC(=O)C1C=CC=C(N[C:11](=[O:38])[CH2:12][N:13]2[N:19]=[C:18]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[C:17]3[CH:26]=[CH:27][CH:28]=[CH:29][C:16]=3[N:15]([CH2:30][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])[C:14]2=[O:37])C=1.[CH2:40]([O:42]C(C1SC=C(C2C=CC=C(N)C=2)N=1)=O)[CH3:41]>>[CH2:40]([O:42][C:11](=[... | COC(=O)c1cccc(NC(=O)CN2N=C(C3CCCCC3)c3ccccc3N(CC(=O)C(C)(C)C)C2=O)c1 | CCOC(=O)c1nc(-c2cccc(N)c2)cs1 | null | null | null | null | null | null | null | 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 obtained by the method used in the preparation of 3-{2-[5-cyclohexyl-1-(3,3-dimethyl-2-oxo-butyl)-2-oxo-1,2-dihydro-3H-1,3,4-benzotriazepin-3-yl]-acetylamino}-benzoic acid methyl ester (Example 1) except that 4-(3-amino-phenyl)-thiazole-2-carboxylic acid ethyl ester (prepared in two steps from 2-... | CCOC(=O)CN1N=C(C2CCCCC2)c2ccccc2N(CC(=O)C(C)(C)C)C1=O | null | null | null |
468,610 | ord_dataset-f1b9e9741a6a4cc68e7070df811f86bb | null | 2000-01-01T00:07:00 | true | C(O[C:6]([N:8](C)[NH:9][C:10](=[O:12])[CH3:11])=O)(C)(C)C.[F:14][C:15]([F:20])([F:19])[C:16]([OH:18])=[O:17]>C(Cl)Cl>[F:14][C:15]([F:20])([F:19])[C:16]([OH:18])=[O:17].[CH3:6][NH:8][NH:9][C:10](=[O:12])[CH3:11] | CC(=O)NN(C)C(=O)OC(C)(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | 1 | To a solution of N'-acetyl-N-methylhydrazinecarboxylic acid tert-butyl ester (0.3 g, 1.59 mmol) in methylene chloride (2 ml) was added trifluoroacetic acid (2 ml) and the mixture was stirred for 60 min. The mixture was concentrated in vacuo and stripped three times with methylene chloride to give 0.32 g (100%) of aceti... | CNNC(C)=O | null | null | null |
1,023,333 | ord_dataset-136cfada6ce247b4919085a57363459e | null | 2011-01-01T00:01:00 | true | [NH2:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11]#[N:12])=[CH:8][CH:7]=[C:6]([N+:13]([O-:15])=[O:14])[CH:5]=2.CO[CH:18]1[CH2:22][CH2:21][CH:20](OC)O1.C(=O)(O)[O-].[Na+].C(=O)=O>C(O)(=O)C.O>[N+:13]([C:6]1[CH:5]=[C:4]2[C:9]([C:10]([C:11]#[N:12])=[C:2]([N:1]3[CH:18]=[CH:22][CH:21]=[CH:20]3)[NH:3]2)=[CH:8][CH:7]=1)([O-:15])=[O... | COC1CCC(OC)O1 | N#Cc1c(N)[nH]c2cc([N+](=O)[O-])ccc12 | null | O=C([O-])O | O=C=O | [Na+] | 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 | 25 | null | A solution of 2-amino-6-nitro-1H-indole-3-carbonitrile (362 mg, 1.79 mmol) in acetic acid (5 mL) is treated with 2,5-dimethoxytetrahydrofuran (0.30 mL, 2.27 mmol), and the solution is heated to reflux for 14 h. After cooling to ambient temperature, the solution is poured into water (100 mL), and solid sodium bicarbonat... | N#Cc1c(-n2cccc2)[nH]c2cc([N+](=O)[O-])ccc12 | null | null | null |
1,509,353 | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | null | 2014-01-01T00:11:00 | true | [CH3:1][N:2]1[C:6]([C@H:7]2[CH2:11][CH2:10][CH2:9][C@@H:8]2[OH:12])=[CH:5][CH:4]=[N:3]1>CCCCCC.C(O)C>[CH3:1][N:2]1[C:6]([C@@H:7]2[CH2:11][CH2:10][CH2:9][C@H:8]2[OH:12])=[CH:5][CH:4]=[N:3]1 | Cn1nccc1[C@H]1CCC[C@@H]1O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCCCC | CCO | null | null | null | null | null | null | null | null | null | null | null | The (1S*,2R*)-2-(1-methyl-1H-pyrazol-5-yl)cyclopentanol prepared in Example 8a was optically resolved with CHIRALPAK IC (Daicel Corp.; hexane/ethanol=8:2) to yield the title compound as a colorless oil. | Cn1nccc1[C@@H]1CCC[C@H]1O | null | null | null |
1,289,185 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]([N:14]=[N+]=[N-])[C@H:10]([OH:17])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]([NH2:14])[C@H:10]([OH:17])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3] | [H][H] | CC(C)(C)OC(=O)N1CC[C@@H](N=[N+]=[N-])[C@H](O)C1 | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | To a stirred solution of (±)-trans-4-azido-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (10 mmol, 2.42 g) in methanol (25 mL) was added 10% palladium on carbon (0.5 g, wet), and the resultant reaction mixture was subjected to hydrogenation using a balloon full of hydrogen for 8 h. The catalyst was filtered t... | CC(C)(C)OC(=O)N1CC[C@@H](N)[C@H](O)C1 | null | null | null |
287,299 | ord_dataset-3577d334f6eb4dc4bd73564fee3f0dfc | null | 1994-01-01T00:03:00 | true | Br[CH2:2][C:3]1[C:8]2[S:9][CH:10]=[C:11]([Cl:12])[C:7]=2[CH:6]=[CH:5][CH:4]=1.Cl.[Cl:14]/[CH:15]=[CH:16]/[CH2:17][NH:18][CH3:19].C(=O)([O-])[O-].[K+].[K+].ClCCl>CS(C)=O>[Cl:12][C:11]1[C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([CH2:2][N:18]([CH2:17]/[CH:16]=[CH:15]/[Cl:14])[CH3:19])[C:8]=2[S:9][CH:10]=1 | Clc1csc2c(CBr)cccc12 | CNC/C=C/Cl | null | Cl | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 16 | To a solution of 2.62 g-(10 mmol) of 7-bromomethyl-3-chlorobezo(b]thiophene in 10 ml of dimethyl sulfoxide were added 1.7 g (12 mmol) of (E)-N-(3-chloro-2-propenyl)methylamine hydrochloride and 2.07 g (15 mmol) of ground potassium carbonate. The mixture was stirred for 16 hours at room temperature, and poured into 150 ... | CN(C/C=C/Cl)Cc1cccc2c(Cl)csc12 | null | 74 | null |
1,693,495 | ord_dataset-c1e70ad912eb438f8d34b1dc681f809a | null | 2016-01-01T00:02:00 | 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[CH2:11][CH2:12][NH:13][C:14](=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21]Cl)[CH:16]=1.[CH3:24][N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>C1COCC1>[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][CH2:12][NH:13][C:... | CN1CCNCC1 | O=C(NCCc1c[nH]c2ccc(Cl)cc12)c1cccc(CCl)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 70 | null | N-(2-(5-Chloro-1H-indol-3-yl)ethyl)-3-((4-methylpiperazin-1-yl)methyl)benzamide was prepared following Method C starting from N-(2-(5-chloro-1H-indol-3-yl)ethyl)-3-(chloromethyl)benzamide (0.050 g; 0.144 mmol) and N-methylpiperazine (0.0554 mL; 0.5 mmol) in THF (3 mL). The mixture was heated at 70° C. for 5 hours. Flas... | CN1CCN(Cc2cccc(C(=O)NCCc3c[nH]c4ccc(Cl)cc34)c2)CC1 | null | 65.9 | null |
1,576,986 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | [Br:1][C:2]1[C:3]([O:11][CH3:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](O)=[O:6]>C1COCC1>[Br:1][C:2]1[C:3]([O:11][CH3:12])=[C:4]([CH2:5][OH:6])[CH:8]=[CH:9][CH:10]=1 | COc1c(Br)cccc1C(=O)O | null | 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 | 0 | 15 | In a 250 ml round bottom flask, 3-bromo-2-methoxybenzoic acid (4.0 g, 17 mmol, 1.0 eq) was dissolved in THF (100 mL). The solution was cooled to 0° C. To above solution was added dropwise borane/THF complex (1 N, 17.3 mL, 17.3 mmol). The solution was warmed to r.t. and let stirred at r.t for 15 hr. The reaction was que... | COc1c(Br)cccc1CO | null | null | null |
1,329,384 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | [N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9]OS(C)(=O)=O)=[CH:3][CH:2]=1.[CH3:15][S-:16].[Na+]>CO>[CH3:15][S:16][CH2:9][CH2:8][CH2:7][C:4]1[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=1 | C[S-] | CS(=O)(=O)OCCCc1ccncc1 | null | [Na+] | 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 | 1 | To a solution of methanesulfonic acid 3-pyridin-4-yl-propyl ester (6.5 g, 30.19 mmol) in methanol (150 mL) was added sodium thiomethoxide (6.35 g, 90.57 mmol, Aldrich). The mixture was stirred at room temperature for 1 h then concentrated in vacuo. The residue was diluted with ethyl acetate and washed with water (2×), ... | CSCCCc1ccncc1 | null | 44.4 | null |
1,574,448 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | [CH3:1][NH:2][C:3]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][CH:11]=[C:10]([N:14]3[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]3)[C:8]=2[CH:9]=1)=[O:4].FC(F)(F)C(O)=O>ClCCl>[CH3:1][NH:2][C:3]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][CH:11]=[C:10]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[C:8]=2[CH:9]=1)=[O:4] | CNC(=O)c1cc2c(N3CCN(C(=O)OC(C)(C)C)CC3)cccc2o1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | null | null | tert-Butyl 4-(2-(methylcarbamoyl)benzofuran-4-yl)piperazine-1-carboxylate (5.8 g, 16.1 mmol) was stirred in dichloromethane (50 mL) and trifluoroacetic acid (12.4 mL, 161.4 mmol) at rt for 4 h. The solvent was removed by rotary evaporation. The residue was dissolved in dichloromethane and 20 mL of 7 N NH3 in methanol w... | CNC(=O)c1cc2c(N3CCNCC3)cccc2o1 | null | null | null |
1,113,005 | ord_dataset-375a420ee9b042918ddca20f02df37d3 | null | 2011-01-01T00:11:00 | true | [OH:1][C:2]1[CH:7]=[CH:6][N:5]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16]O)=[CH:12][CH:11]=2)[C:4](=[O:18])[CH:3]=1.P(Br)(Br)[Br:20]>C(Cl)Cl>[Br:20][CH2:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][CH2:8][N:5]2[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][C:4]2=[O:18])=[CH:11][CH:12]=1 | O=c1cc(O)ccn1CCc1ccc(CO)cc1 | BrP(Br)Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 8 | To 2.45 g (10.0 mmol) 4-hydroxy-1-[2-(4-hydroxymethyl-phenyl)-ethyl]-1H-pyridin-2-one (preparation 2.b) in 25 mL DCM is added 470 μL (5.00 mmol) phosphorus tribromide at 0° C. The mixture is stirred overnight at RT and then poured into ice water. The precipitate is collected, washed with DCM and dried. | O=c1cc(O)ccn1CCc1ccc(CBr)cc1 | null | null | null |
1,036,771 | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | null | 2011-01-01T00:03:00 | true | [F:1][C:2]([F:23])([F:22])[C:3]([N:5]1[CH2:10][CH2:9][N:8]([S:11]([C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2[CH3:21])(=[O:13])=[O:12])[CH2:7][CH2:6]1)=[O:4].C1C(=O)N([Br:31])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:31][CH2:21][C:15]1[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:14]=1[S:11]([N:8]1[CH2:7][... | O=C1CCC(=O)N1Br | Cc1ccc(F)cc1S(=O)(=O)N1CCN(C(=O)C(F)(F)F)CC1 | null | CC(C)(C#N)N=NC(C)(C)C#N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of Intermediate 2 (37.5 g, 105.9 mmol), NBS (19.4 g, 105.9 mmol) and AIBN (0.45 g, 2.8 mmol) in carbon tetrachloride (500 mL) was refluxed for 4 h. The mixture was cooled, concentrated and purified over silica gel eluting with EtOAc to give the title compound contaminated with starting material and dibrominat... | O=C(N1CCN(S(=O)(=O)c2cc(F)ccc2CBr)CC1)C(F)(F)F | null | null | null |
509,889 | ord_dataset-85c00026681b46f89ef8634d2b8618c3 | null | 2001-01-01T00:07:00 | true | [C:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1)#[N:2].Br[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.BrCC(OCC)=O.[Zn]>[NH2:2][C:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1)=[CH:10][C:11]([O:13][CH2:14][CH3:15])=[O:12] | N#Cc1cccnc1 | CCOC(=O)CBr | null | O=C([O-])[O-] | [K+] | [Zn] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 0.83 | In an atmosphere of argon, activated zinc powder (4.88 g, 0.07 g atom) was suspended in anhydrous tetrahydrofuran (THF) (25.0 ml) to which was subsequently added dropwise several drops of ethyl bromoacetate while heating under reflux. When color of the reaction solution became green, 3-cyanopyridine (1.59 g, 15.0 mmol)... | CCOC(=O)C=C(N)c1cccnc1 | null | 78.4 | null |
231,882 | ord_dataset-67c9ee844bf341888b345c8e36183b40 | null | 1991-01-01T00:07:00 | true | [CH3:1][Si:2](Cl)([CH3:4])[CH3:3].N1C=CN=C1.[CH:11]1([C@@:17]([OH:27])([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:18](=[O:20])[CH3:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.CCOCC>CN(C=O)C>[CH:21]1([C@:17]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)([O:27][Si:2]([CH3:4])([CH3:3])[CH3:1])[C:18](=[O:20])[CH... | C[Si](C)(C)Cl | CC(=O)[C@](O)(c1ccccc1)C1CCCCC1 | null | c1c[nH]cn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCOCC | null | null | null | null | null | null | null | null | null | 85 | null | To a solution of 12 ml (95 mmoles) of trimethylsilyl chloride and 11.6 g (172 mmoles) of imidazole in 100 ml of DMF was added 20 g (86 mmoles) of (R)-1-cyclohexyl-1-hydroxy-1-phenyl-2-propanone. This mixture was heated to 85° C. overnight. The next day, the mixture was cooled and poured onto a mixture of 100 ml of petr... | CC(=O)[C@](O[Si](C)(C)C)(c1ccccc1)C1CCCCC1 | null | 68.7 | null |
1,664,631 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | C([O:3][C:4]([C:6]1[C:7]([N:29]([CH3:31])[CH3:30])=[N:8][C:9]2[C:14]([C:15]=1[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[Cl:23])=[CH:13][C:12]([Cl:24])=[CH:11][C:10]=2[C:25]([F:28])([F:27])[F:26])=[O:5])C.[OH-].[Na+]>C(O)C>[Cl:24][C:12]1[CH:13]=[C:14]2[C:9](=[C:10]([C:25]([F:28])([F:26])[F:27])[CH:11]=1)[N:8]... | CCOC(=O)c1c(N(C)C)nc2c(C(F)(F)F)cc(Cl)cc2c1Cc1ccccc1Cl | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared in analogy to example 12 step B from a mixture of 6-chloro-4-(2-chloro-benzyl)-2-dimethylamino-8-trifluoromethyl-quinoline-3-carboxylic acid ethyl ester (50 mg, 0.106 mmol) and 1N NaOH in ethanol. Pale yellow solid (22 mg, 47%). LC-MS (ESI): 441 (M−H)−. | CN(C)c1nc2c(C(F)(F)F)cc(Cl)cc2c(Cc2ccccc2Cl)c1C(=O)O | null | null | null |
437,577 | ord_dataset-a1e9aa99368e4e5da8b1786b1c05521d | null | 1999-01-01T00:08:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:12][CH3:13])[C:10]=1[OH:11])[CH:6]=O.[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:12][CH3:13])[C:10]=1[OH:11])[CH:6]=[N:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1 | COc1cc(C=O)cc(OC)c1O | Nc1ccccc1 | 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 | 8 | 3,5-Dimethoxy-4-hydroxybenzaldehyde (1 g, 5.46 mmol) was dissolved in methanol (50 ml) and aniline (560 mg, 6.01 mmol, 0.35 ml, neat liquid) was added to the solution by syringe. The resultant reaction mixture was stirred overnight at room temperature under nitrogen then taken to dryness in vacuo. The yellow crystals t... | COc1cc(C=Nc2ccccc2)cc(OC)c1O | null | null | null |
1,747,076 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | [C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH:13]([CH3:15])[CH3:14])[C:6]([OH:8])=O)#[N:2].C(Cl)(=O)C(Cl)=O.[CH2:22]([CH2:24][NH2:25])[OH:23]>C(Cl)Cl.CN(C=O)C>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH:13]([CH3:15])[CH3:14])[C:6]([NH:25][CH2:24][CH2:22][OH:23])=[O:8])#[N:2] | CC(C)Oc1ccc(C(=O)O)cc1C#N | NCCO | null | O=C(Cl)C(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CN(C)C=O | null | null | null | null | null | null | null | null | null | 50 | 2 | To a stirring suspension of 3-cyano-4-isopropoxybenzoic acid (1.0 g, 4.8 mmol) in DCM (20 mL) was added oxalyl chloride (3.7 g, 29.2 mmol) followed by two drops DMF. The reaction mixture was stirred at 50° C. for 2 h. The mixture was concentrated and the residue re-dissolved in DCM (10 mL). Ethanolamine (0.6 g, 9.7 mmo... | CC(C)Oc1ccc(C(=O)NCCO)cc1C#N | null | 83.9 | null |
1,317,388 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | [C:1]([O:5][C:6]([NH:8][C@@H:9]([CH3:13])[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C[N:15]1CCOCC1.ClC(OCC(C)C)=O.[OH-].[NH4+]>C1COCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH3:13])[C:10]([NH2:15])=[O:11])([CH3:4])([CH3:3])[CH3:2] | CN1CCOCC1 | C[C@H](NC(=O)OC(C)(C)C)C(=O)O | null | CC(C)COC(=O)Cl | [NH4+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 5 | To a stirred solution of (2S)-2-[(tert-butoxycarbonyl)amino]propanoic acid (1 g, 0.005 mol) in THF at 0° C. was added 4-methylmorpholine (0.588 g, 0.00581 mol) followed by dropwise addition of isobutyl chloroformate (0.794 g, 0.00581 mol) over 2 min. The reaction was stirred at 0° C. for 30 min. after which a solution ... | C[C@H](NC(=O)OC(C)(C)C)C(N)=O | null | null | null |
945,611 | ord_dataset-ed680843f6d14f5c9901869b2a06b4a4 | null | 2010-01-01T00:03:00 | true | [Br:1][C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C1([O:20][C:21]([O:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=O)C=CC=CC=1>>[Br:1][C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:9][CH2:10][N:11]([C:21]([O:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[O:20])[CH2:12][CH2:13]2)=[C... | Brc1ccc(N2CCNCC2)cn1 | CCOC(=O)COC(=O)Oc1ccccc1 | null | null | null | null | null | null | null | 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 process is performed as described in Example 1 (step 1.2.). Starting with 3.57 g (14.76 mmol) of 1-(6-bromo-3-pyridyl)piperazine, obtained in step 7.3., and 3.97 g (17.71 mmol) of ethyl [(phenyloxycarbonyl)oxy]acetate, prepared in step 1.1. of Example 1, and after chromatography on silica gel, eluting with a 99/1 a... | CCOC(=O)COC(=O)N1CCN(c2ccc(Br)nc2)CC1 | null | null | null |
1,283,945 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | CC1C=CC(S(O[CH:12]2[CH2:40][CH2:39][C:15]3([O:19][N:18]=[C:17]([C:20]4[C:21]([NH:32][CH:33]5[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]5)=[C:22]5[C:28](C)=[N:27][N:26]([CH2:30][CH3:31])[C:23]5=[N:24][CH:25]=4)[CH2:16]3)[CH2:14][CH2:13]2)(=O)=O)=CC=1.[N-:41]=[N+:42]=[N-:43].[Na+].O>CN(C)C=O>[N:41]([CH:12]1[CH2:40][CH2:39][... | [N-]=[N+]=[N-] | CCn1nc(C)c2c(NC3CCCCC3)c(C3=NOC4(CCC(OS(=O)(=O)c5ccc(C)cc5)CC4)C3)cnc21 | null | [Na+] | null | 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 | 65 | 8 | 3-[4-(Cyclohexylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridin-5-yl]-1-oxa-2-azaspiro[4.5]dec-2-en-8-yl 4-methylbenzenesulfonate (0.00090 mole) (example 39) is taken in dimethylformamide. Sodium azide (0.0027 mole) is added. The reaction mixture is stirred at 60-70° C. overnight. It is cooled and water is added and extractio... | CCn1ncc2c(NC3CCCCC3)c(C3=NOC4(CCC(N=[N+]=[N-])CC4)C3)cnc21 | null | null | null |
336,930 | ord_dataset-65c44df6676d4ce3a1874db5d7958ca9 | null | 1996-01-01T00:08:00 | true | B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:17]([C:18]3[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=3)=[CH:16][C:15]([C:28]([F:31])([F:30])[F:29])=[N:14]2)=[CH:9][CH:8]=1>ClCCl>[OH:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]2[C:17]([C:18]3[CH:19]=[CH:20][C:21]([S:24]([CH3:27])(=[O:26])=[O:2... | COc1ccc(-n2nc(C(F)(F)F)cc2-c2ccc(S(C)(=O)=O)cc2)cc1 | null | null | BrB(Br)Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 5 | 2 | Boron tribromide (1M in dichloromethane; 11 ml) was added to an ice-cooled solution of 1-(4-methoxyphenyl)-5-[4-(methylsulfonyl)phenyl]-3-(trifluoromethyl)pyrazole (1.4 g) in dichloromethane (30 ml). The mixture was stirred at 5° C. for 2 hours and concentrated in vacuo. The residue was triturated in dilute hydrochlori... | CS(=O)(=O)c1ccc(-c2cc(C(F)(F)F)nn2-c2ccc(O)cc2)cc1 | null | 67.4 | null |
1,767,106 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | [C:1]([C:5]1[CH:9]=[C:8]([NH2:10])[NH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:17]([O:19][C:20](=[O:29])[C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23](Br)[CH:22]=1)[CH3:18]>[Cu]I>[CH2:17]([O:19][C:20](=[O:29])[C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([N:7]2[C:8]([NH2:10])=[CH:9][C:5]([C:1]([C... | CC(C)(C)c1cc(N)[nH]n1 | CCOC(=O)c1cc(Cl)cc(Br)c1 | null | [Cu]I | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 3-(Tert-butyl)-1H-pyrazol-5-amine (1.10 g, 7.90 mmol), potassium carbonate (2.29 g, 16.6 mmol), and copper (I) iodide (75.0 mg, 1.58 mmol) were weighed into a microwave vial and purged with argon. 3-Bromo-5-chloro-benzoic acid ethyl ester (2.50 g, 9.49 mmol) was then added, followed by trans-N,N′-dimethylcyclohexane-di... | CCOC(=O)c1cc(Cl)cc(-n2nc(C(C)(C)C)cc2N)c1 | null | 19.2 | null |
1,257,894 | ord_dataset-266f60b4555945d6afb2d2bdf5fa04e0 | null | 2013-01-01T00:02:00 | true | Br[C:2]1[N:7]=[C:6]([CH:8]([F:16])[CH2:9][N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:5]=[CH:4][CH:3]=1.[NH2:17][C:18]1[S:19][C:20]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([OH:35])([CH3:34])[CH3:33])=[CH:28][C:27]=2[F:36])=[CH:21][C:22]=1[C:23]([NH2:25])=[O:24]>>[F:36][C:27]1[CH:28]=[C:29]([C:32]([OH:35])([CH3:33])[C... | FC(CN1CCOCC1)c1cccc(Br)n1 | CC(C)(O)c1ccc(-c2cc(C(N)=O)c(N)s2)c(F)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared according to the general procedure in Example 1 using 4-[2-(6-bromopyridin-2-yl)-2-fluoroethyl]morpholine (80 mg, 0.28 mmol) and 2-amino-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide (81 mg, 0.28 mmol) as the starting materials. | CC(C)(O)c1ccc(-c2cc(C(N)=O)c(Nc3cccc(C(F)CN4CCOCC4)n3)s2)c(F)c1 | null | null | null |
1,329,568 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | [C:1]([C:5]1[N:10]=[CH:9][C:8]([C:11]2[N:12]([C:32]([N:34]3[CH2:39][CH2:38][CH:37]([CH2:40][C:41]([OH:43])=O)[CH2:36][CH2:35]3)=[O:33])[C@@:13]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)([CH3:24])[C@@:14]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)([CH3:16])[N:15]=2)=[C:7]([O:44][CH2:45][CH3:46... | FC(F)(F)C1CCCN1 | CCOc1cc(C(C)(C)C)ncc1C1=N[C@@](C)(c2ccc(Cl)cc2)[C@@](C)(c2ccc(Cl)cc2)N1C(=O)N1CCC(CC(=O)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 | In a manner analogous to the method described in example 163, {1-[(4S,5R)-2-(6-tert-butyl-4-ethoxy-pyridin-3-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl]-piperidin-4-yl}-acetic acid was reacted with 2-trifluoromethyl-pyrrolidine (Aldrich) to give the title compound. HR-MS (ES, m/z) calcu... | CCOc1cc(C(C)(C)C)ncc1C1=N[C@@](C)(c2ccc(Cl)cc2)[C@@](C)(c2ccc(Cl)cc2)N1C(=O)N1CCC(CC(=O)N2CCCC2C(F)(F)F)CC1 | null | null | null |
1,597,712 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | O1[C:5]2([CH2:10][CH2:9][CH:8]([CH:11]([NH:14][S:15]([C:18]([F:21])([F:20])[F:19])(=[O:17])=[O:16])[CH2:12][CH3:13])[CH2:7][CH2:6]2)[O:4]CC1.Cl>CC#N>[F:20][C:18]([F:19])([F:21])[S:15]([NH:14][CH:11]([CH:8]1[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]1)[CH2:12][CH3:13])(=[O:16])=[O:17] | CCC(NS(=O)(=O)C(F)(F)F)C1CCC2(CC1)OCCO2 | null | null | Cl | 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 | A solution of N-(1-1,4-dioxaspiro[4.5]decan-8-ylpropyl)-1,1,1-trifluoromethanesulfonamide (as prepared in the previous step, 47 mg, 0.14 mmol, 1.00 equiv) in CH3CN (5 mL) and HCl (2M, 1 mL) was stirred for 2 h at room temperature. The resulting mixture was concentrated under vacuum. The residue was diluted with 10 mL o... | CCC(NS(=O)(=O)C(F)(F)F)C1CCC(=O)CC1 | null | null | null |
1,213,901 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | [NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1.[OH-].[K+].[CH3:25]I>CC(C)=O>[CH3:25][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([C... | CI | CC(C)(C)OC(=O)N1CCC(c2nc3ccccc3[nH]2)CC1 | null | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | null | null | null | null | null | null | null | null | null | null | 25 | 0.17 | The tert-butyl 4-(1H-benzimidazol-2-yl)piperidine-1-carboxylate (50.0 mg, 0.166 mmol) was dissolved in 2 mL of acetone with freshly ground potassium hydroxide (46.4 mg, 0.830 mmol). The mixture was stirred for 10 minutes at ambient temperature, and then methyl iodide (11.4 μL, 0.183 mmol) was added. After 10 minutes, t... | Cn1c(C2CCN(C(=O)OC(C)(C)C)CC2)nc2ccccc21 | null | null | null |
922,124 | ord_dataset-8e59bd24817446f7b1c68e805b8e5f1d | null | 2009-01-01T00:11:00 | true | [CH3:1][N:2]1[C:10]2[C@@:9]3([CH3:14])[C:11]([CH3:13])([CH3:12])[C@H:6]([CH2:7][CH2:8]3)[C:5]=2[C:4](=[O:15])[NH:3]1.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C=O>[CH2:16]([N:3]1[C:4](=[O:15])[C:5]2[C@@H:6]3[C:11]([CH3:12])([CH3:13])[C@@:9]([CH3:14])([CH2:8][CH2:7]3)[C:10]=2[N:2]1[CH3:1])[C:17]1[C... | BrCc1ccccc1 | Cn1[nH]c(=O)c2c1[C@]1(C)CC[C@H]2C1(C)C | 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 | 100 | null | A mixture of (4S,7R)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 19; 100 mg, 0.49 mmol) and benzyl bromide (52 μL, 0.44 mmol) in N,N-dimethylformamide (4.5 mL) was heated at 100° C. overnight. The reaction mixture was evaporated and the residue was purified using a Biotage 40S syst... | Cn1c2c(c(=O)n1Cc1ccccc1)[C@H]1CC[C@]2(C)C1(C)C | null | 54.8 | null |
194,130 | ord_dataset-b83b16f2fb1a4f8782f3d82c1766cc6b | null | 1989-01-01T00:08:00 | true | [CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]([OH:16])=O)[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:18][C@@H:19]([CH2:28][CH:29]([CH3:31])[CH3:30])[CH:20]([OH:27])[C:21]([O:23][CH:24]([CH3:26])[CH3:25])=[O:22].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C>CN(C)C=O>[CH2:1]([O:8][C:9]([NH:11][... | CC(C)C[C@H](N)C(O)C(=O)OC(C)C | C[C@H](NC(=O)OCc1ccccc1)C(=O)O | null | Cl | [N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | To a solution of 61 mg of N-benzyloxycarbonyl-L-alanine and 79 mg of isopropyl (2RS, 3S)-3-amino-2-hydroxy-5-methylhexanoate hydrochloride in 5 ml of N,N-dimethylformamide were added successively 0.071 ml of diphenylphosphoryl azide and 0.125 ml of triethylamine with stirring under ice-cooling, and the mixture was stir... | CC(C)C[C@H](NC(=O)[C@H](C)NC(=O)OCc1ccccc1)C(O)C(=O)OC(C)C | null | 50.2 | null |
511,650 | ord_dataset-85c00026681b46f89ef8634d2b8618c3 | null | 2001-01-01T00:07:00 | true | [CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][C@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2C(OC(C)(C)C)=O)[CH2:4][CH2:3]1>FC(F)(F)C(O)=O.ClCCl>[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][C@H:10]2[CH2:14][CH2:13][CH2:12][NH:11]2)[CH2:4][CH2:3]1 | CC1CCN(CC[C@H]2CCCN2C(=O)OC(C)(C)C)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | null | null | A solution of the protected amine, (R)-2-[2-(4-methyl-piperidin-1-yl)ethyl ]pyrrolidine-1-carboxylic acid, tert-butyl ester (D5) (3.0 g, 10 mmol) in trifluoroacetic acid (15 ml) and dichloromethane (50 ml) was heated to reflux for 18 hours. The reaction mixture was concentrated and the residue partitioned between CH2Cl... | CC1CCN(CC[C@H]2CCCN2)CC1 | null | 101.9 | null |
1,284,054 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [C-:1]#[N:2].[K+].[CH:4]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH:13]([CH3:15])[CH3:14])[C:8]=1[NH:16][C:17](=[O:38])[CH2:18][N:19]1[C:23](=[O:24])[C:22]2([CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[N:21]([C:30]2[CH:35]=[CH:34][C:33](I)=[CH:32][CH:31]=2)[C:20]1=[O:37])([CH3:6])[CH3:5]>O1CCCC1.C(OCC)(=O)C.[Cu](I)I.C1C=CC([... | [C-]#N | CC(C)c1cccc(C(C)C)c1NC(=O)CN1C(=O)N(c2ccc(I)cc2)C2(CCCCC2)C1=O | null | I[Cu]I | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 80 | null | 38 mg (0.58 mmol, 2 eq.) of potassium cyanide and 5.5 mg (0.029 mmol, 0.1 eq.) of copper iodide are added to 170 mg (0.29 mmol, 1 eq.) of N-(2,6-diisopropyl-phenyl)-2-[1-(4-iodo-phenyl)-2,4-dioxo-1,3-diaza-spiro[4.5]dec-3-yl]acetamide in 10 ml of tetrahydrofuran. The reaction medium is degassed with nitrogen for 20 min... | CC(C)c1cccc(C(C)C)c1NC(=O)CN1C(=O)N(c2ccc(C#N)cc2)C2(CCCCC2)C1=O | null | null | null |
319,242 | ord_dataset-0c61835e3a0b4986aabf2b61b708e322 | null | 1995-01-01T00:11:00 | true | C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])[CH:10]([CH2:21][CH2:22][OH:23])[CH2:9]1)C1C=CC=CC=1>CO.[Pd]>[OH:23][CH2:22][CH2:21][CH:10]1[N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])[CH2:12][CH2:13][NH:8][CH2:9]1 | Cc1ccccc1N1CCN(Cc2ccccc2)CC1CCO | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | 1-Benzyl-3-(2-hydroxyethyl)-4-(2-methylphenyl)piperazine from Step 1 above (1.5 g; 4.8 mmol) in 50 mL of MeOH containing 150 mg of palladium black was shaken on a Parr apparatus under an atmosphere of hydrogen (55 psig) for 18 h. The catalyst was removed by filtration through Celite and the filtercake was washed with M... | Cc1ccccc1N1CCNCC1CCO | null | 97 | null |
1,731,167 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | [CH2:1]([O:3][P:4]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].O.O.[OH-].[Al+3:17].[OH-].[OH-]>CC(C)=O>[CH2:7]([O:6][P:4]([CH2:9][CH2:10][C:11]([O-:13])=[O:12])([O:3][CH2:1][CH3:2])=[O:5])[CH3:8].[CH2:7]([O:6][P:4]([CH2:9][CH2:10][C:11]([O-:13])=[O:12])([O:3][CH2:1][CH3:2])=[O:5])[CH3:8].[... | CCOP(=O)(CCC(=O)O)OCC | null | null | [Al+3] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | O | null | null | null | null | null | null | null | null | null | 90 | 8 | Use as a reaction vessel a 500 milliliter (mL) single neck round bottomed flask fitted with a condenser with a nitrogen inlet. Charge the vessel with 3-(diethyoxyphosphoryl)propanoic acid (20.30 g) followed by the addition of water (150 mL) and aluminum hydroxide monohydrate (2.709 g). Heat the resulting solution to 90... | CCOP(=O)(CCC(=O)[O-])OCC | null | null | null |
150,653 | ord_dataset-b9a9e369e9da4413999591aa08f4c3e3 | null | 1986-01-01T00:11:00 | true | [NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].[OH-].[Na+].[CH3:12][S:13](Cl)(=[O:15])=[O:14]>>[CH3:12][S:13]([CH:6]([CH2:5][CH2:4][CH2:3][CH2:2][NH2:1])[C:7]([OH:9])=[O:8])(=[O:15])=[O:14] | NCCCCCC(=O)O | CS(=O)(=O)Cl | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Analogously to Example 20a, 65.6 g of ε-aminocaproic acid are reacted with 40 ml of methanesulfonyl chloride in the presence of 2N NaOH and the mixture is worked up. The DCA salt is prepared, and 42.3 g of melting point 134° are obtained. | CS(=O)(=O)C(CCCCN)C(=O)O | null | null | null |
716,878 | ord_dataset-c8a367b56b4f406b878f51867b157d19 | null | 2006-01-01T00:06:00 | true | [CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:25]=[CH:26][CH:27]=1)[CH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=2)[C:12]([CH:23]=[O:24])=[CH:11][N:10]=1)([CH3:3])[CH3:2].[Se](=O)=[O:29]>C(OCC)(=O)C>[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:25]=[CH:26][CH:27]=1)[C:8]([C:9]1[C:18]2[C:13](=[CH:14]... | COc1cc2c(C=O)cnc(Cc3cccc(OC(C)C)c3)c2cc1OC | O=[Se]=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 1-(3-isopropoxy-benzyl)-6,7-dimethoxy-isoquinoline-4-carbaldehyde (200 mg, 0.547 mmol) and selenium dioxide (121 mg, 1.09 mmol) in ethyl acetate was refluxed for 45 min. The mixture was cooled and filtered through celite. The celite was washed well with ethyl acetate and the combined filtrates were concen... | COc1cc2c(C=O)cnc(C(=O)c3cccc(OC(C)C)c3)c2cc1OC | null | 77.1 | null |
1,410,507 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | [Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:20])[C:7]=1[S:8][C:9]1[S:13][C:12]([C:14](Cl)=[O:15])=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18].[NH2:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1>>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:20])[C:7]=1[S:8][C:9]1[S:13][C:12]([C:14]([NH:21][CH2:22][CH2:23][C:24]2[C... | NCCc1ccccn1 | O=C(Cl)c1cc([N+](=O)[O-])c(Sc2c(Cl)cncc2Cl)s1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared according to the procedure described for example 50 from 5-[(3,5-dichloro-4-pyridyl)sulfanyl]-4-nitro-thiophene-2-carbonyl chloride (150 mg, 0.41 mmol) and 2-(2-aminoethyl)pyridine (65 mg, 0.49 mmol). The title compound was obtained as a solid (55 mg, 30% yield). 1H NMR (400 MHz, d6-DMSO) δ: 8.98 (2H, s), 8.94... | O=C(NCCc1ccccn1)c1cc([N+](=O)[O-])c(Sc2c(Cl)cncc2Cl)s1 | null | null | null |
1,389,340 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]=[C:13]([NH2:23])[N:14]=[C:15]([O:18][CH2:19][CH2:20][O:21][CH3:22])[C:16]=3[N:17]=2)=[CH:4][CH:3]=1.[CH3:24]OCCO>>[NH2:23][C:13]1[N:14]=[C:15]([O:18][C@@H:19]2[CH2:24][CH2:22][O:21][CH2:20]2)[C:16]2[N:17]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=... | COCCOc1nc(N)nc2ccc(-c3ccc(F)cc3)nc12 | COCCO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 6-(4-fluoro-phenyl)-4-(2-methoxy-ethoxy)-pyrido[3,2-d]pyrimidin-2-ylamine (example 23) was obtained from 2-methoxy-ethanol; MS (m/z): 315 ([M+H]+, 100). | Nc1nc(O[C@@H]2CCOC2)c2nc(-c3ccc(F)cc3)ccc2n1 | null | null | null |
1,654,805 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[C:19]([OH:20])=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][N:11]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][CH:29]1[CH2:33][O:32][C:31]([CH3:35])([CH3:34])[CH2:30]1.O>CN(C=O)C>[CH3:34][C:31]1([CH3:35])[O:32][CH2:33][CH:29]([CH2:28][O:20][C:19]2[C:10]... | COC(=O)c1cnc(-c2cc(OC)ccc2F)c(O)c1 | CC1(C)CC(CBr)CO1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | A solution of methyl 6-(2-fluoro-5-methoxyphenyl)-5-hydroxynicotinate (700 mg), potassium carbonate (1.10 g) and 4-(bromomethyl)-2,2-dimethyltetrahydrofuran (730 mg) in DMF (5.0 mL) was stirred at 80° C. for 4 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate and the extract ... | COC(=O)c1cnc(-c2cc(OC)ccc2F)c(OCC2COC(C)(C)C2)c1 | null | 99.7 | null |
1,690,346 | ord_dataset-c1e70ad912eb438f8d34b1dc681f809a | null | 2016-01-01T00:02:00 | true | [OH:1][C@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@:3]1([CH2:20][C:21]1[CH:31]=[CH:30][C:24]([C:25](OCC)=[O:26])=[CH:23][CH:22]=1)[C:11]1[CH2:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2.[NH2:32][C:33]1[CH:34]=[CH:35][C:36]([OH:42])=[C:37]([CH:41]=1)[C:38]([OH:40])=[O:39].C[Al](C)C>C1COCC1... | CCOC(=O)c1ccc(C[C@]2(C3=Cc4ccccc4C3)Cc3ccccc3[C@@H]2O)cc1 | Nc1ccc(O)c(C(=O)O)c1 | null | C[Al](C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | To a mixture of ethyl 4-(((1R,2R)-1-hydroxy-2,3-dihydro-1H,1′H-[2,2′-biinden]-2-yl)methyl)benzoate (11, 200 mg, 0.48 mmol), 5-amino-2-hydroxybenzoic acid (75 mg, 0.48 mmol) and THF (1.0 mL) in a 5 mL microwave vial, was added trimethylaluminium (0.5 mL, 20% solution in toluene) and the mixture irradiated at 100° C. for... | O=C(Nc1ccc(O)c(C(=O)O)c1)c1ccc(C[C@]2(C3=Cc4ccccc4C3)Cc3ccccc3[C@@H]2O)cc1 | null | 30.2 | null |
522,012 | ord_dataset-262b40ea420c471da9b9244fe9b8f645 | null | 2001-01-01T00:10:00 | true | Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][O:10][C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[C:13](=[O:23])[C:14](=[C:20]([CH3:22])[CH3:21])[O:15]3)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[F:30][C:31]1[CH:45]=[CH:44][C:34]([C:35]([NH:37][CH:38]2[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]2)=[O:36])=[CH:33][CH:32]=1>CN(C)C... | O=C(NC1CCNCC1)c1ccc(F)cc1 | CC(C)=C1Oc2cccc(OCc3ccc(CCl)cc3)c2C1=O | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 60 | null | A mixture of 570 mg 4-(4-chloromethyl-phenylmethoxy)-2-isopropylidenecoumaran-3-one (preparation 2), 240 mg potassium carbonate, 400 mg 4-(4-fluorobenzamido)piperidine and 15 ml dimethylformamide is warmed to 60° C. for 3 hours, then evaporated, mixed with water and extracted with ethyl acetate. After evaporation of th... | CC(C)=C1Oc2cccc(OCc3ccc(CN4CCC(NC(=O)c5ccc(F)cc5)CC4)cc3)c2C1=O | null | 20.2 | null |
1,166,563 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | [C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].[H-].[Na+].[Cl:12][C:13]1[CH:14]=[C:15]([C:20](=[O:22])[CH3:21])[CH:16]=[N:17][C:18]=1Cl>CS(C)=O>[C:20]([C:15]1[CH:14]=[C:13]([Cl:12])[C:18]([CH:2]([C:1]([O:8][CH3:9])=[O:7])[C:3]([O:5][CH3:6])=[O:4])=[N:17][CH:16]=1)(=[O:22])[CH3:21] | COC(=O)CC(=O)OC | CC(=O)c1cnc(Cl)c(Cl)c1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | null | null | null | null | null | null | null | null | null | null | 25 | 0.67 | Dimethyl malonate (4.69 g, 35.5 mmol) was dissolved in DMSO (24.0 ml). This solution was added 70% NaH (1.33 g, 33.2 mmol) at 0° C. The resulting mixture was warmed up to room temperature, then stirred at the same temperature for 40 min. To this solution was added 1-(5,6-dichloropyridin-3-yl)ethanone (Tetrahedron 1992,... | COC(=O)C(C(=O)OC)c1ncc(C(C)=O)cc1Cl | null | 32.2 | null |
830,972 | ord_dataset-47bd90bf5ec74fcd99ce250a56e18c8f | null | 2008-01-01T00:07:00 | true | [CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[C:17]([O:21][C:22]([N:24]1[CH2:28][CH2:27][CH2:26][C@@H:25]1[CH2:29]OS(C1C=CC(C)=CC=1)(=O)=O)=[O:23])([CH3:20])([CH3:19])[CH3:18]>CN(C=O)C>[C:17]([O:21][C:22]([N:24]1[CH2:28][CH2:27][CH2:26][C@@H:25]1[CH2:2... | Oc1ccc(Cc2ccccc2)cc1 | Cc1ccc(S(=O)(=O)OC[C@H]2CCCN2C(=O)OC(C)(C)C)cc1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 0 | 0.17 | To a solution of 4-benzylphenol (103 mg, 0.56 mmol) in DMF (1 mL) was added 95% NaH (19 mg, 0.75 mmol) at 0° C., and the resulting mixture was stirred at 0° C. for 10 min. A solution of the tosylate (200 mg, 0.56 mmol) from Step 1 in DMF (2 mL) was added to the reaction mixture dropwise over 5 min., and the reaction wa... | CC(C)(C)OC(=O)N1CCC[C@@H]1COc1ccc(Cc2ccccc2)cc1 | null | 72.9 | null |
432,590 | ord_dataset-8cbb58558c904b2b85fa7a1b084a0de9 | null | 1999-01-01T00:06:00 | true | C(O[C:4]([C:6]1([C:29]([O:31]CC)=[O:30])[O:10][C:9]2[CH:11]=[CH:12][C:13]([CH2:15][CH:16]([NH:18][CH2:19][CH:20]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=3)[OH:21])[CH3:17])=[CH:14][C:8]=2[O:7]1)=[O:5])C.[O:34]1[CH:38]=[CH:37][CH:36]=[C:35]1[CH2:39][NH2:40]>C(O)C>[O:34]1[CH:38]=[CH:37][CH:36]=[C:35]1[CH2:39... | NCc1ccco1 | CCOC(=O)C1(C(=O)OCC)Oc2ccc(CC(C)NCC(O)c3cccc(Cl)c3)cc2O1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 5-{2-[2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-propyl}-benzo[1,3]dioxole-2,2-dicarboxylic acid bis-ethyl ester (2.4 g, 5 mmol) and 2-furanylmethylamine (10 mL, excess) was refluxed in ethanol for 48 h. The reaction mixture was concentrated and the residue obtained was extracted with chloroform:methanol (3... | CC(Cc1ccc2c(c1)OC(C(=O)O)(C(=O)N(Cc1ccco1)Cc1ccco1)O2)NCC(O)c1cccc(Cl)c1 | null | null | null |
1,421,950 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | [CH3:1][Si:2]([CH3:40])([CH3:39])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]4[C:25]([CH:26]=3)=[CH:24][C:23]([F:27])=[CH:22][CH:21]=4)=[C:12]2[N:11]=[C:10]([CH:28]([OH:30])[CH3:29])[CH:9]=1.C(N(CC)CC)C.[C... | CS(=O)(=O)Cl | CC(O)c1cc(N(COCC[Si](C)(C)C)COCC[Si](C)(C)C)n2ncc(-c3cnc4ccc(F)cc4c3)c2n1 | 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 | null | 0.25 | To a solution of 1-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(6-fluoroquinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)ethanol (6.1 g, 10.4 mmol) in methylene chloride (100 mL) and triethylamine (7.1 mL, 50.9 mmol) under nitrogen was added methanesulfonyl chloride (2.4 mL, 31.0 mmol) dropwise. After 15 minutes the r... | CC(OS(C)(=O)=O)c1cc(N(COCC[Si](C)(C)C)COCC[Si](C)(C)C)n2ncc(-c3cnc4ccc(F)cc4c3)c2n1 | null | 98.8 | null |
1,113,068 | ord_dataset-375a420ee9b042918ddca20f02df37d3 | null | 2011-01-01T00:11:00 | true | O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[S:20][CH:21]=[CH:22][CH:23]=3)=[CH:13][C:12]2=[O:24])=[CH:5][CH:4]=1.[NH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1>>[N:25]1([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]4[S:2... | C1CCNC1 | O=c1cc(OCc2cccs2)ccn1CCc1ccc(CO)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 | 1-[2-(4-Pyrrolidin-1-ylmethyl-phenyl)-ethyl]-4-(thiophen-2-ylmethoxy)-1H-pyridin-2-one is prepared as example 2.1b from 45 mg (mg (0.13 mmol) 1-[2-(4-hydroxymethyl-phenyl)-ethyl]-4-(thiophen-2-ylmethoxy)-1H-pyridin-2-one (example 2.1a) and 22 μL (0.26 mmol) pyrrolidine. The product is purified via reverse HPLC chromato... | O=c1cc(OCc2cccs2)ccn1CCc1ccc(CN2CCCC2)cc1 | null | null | null |
478,962 | ord_dataset-21c1b1c06c7e4e09a38b5b1c71a32e52 | null | 2000-01-01T00:10:00 | true | [C:1]([C:5]1[C:10]2[CH2:11][C:12]([CH:15]=[CH:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])([CH3:14])[O:13][C:9]=2[CH:8]=[C:7]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:6]=1[OH:27])([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.[C].[Pd]>[C:1]([C:5]1[C:10]2[CH2:11][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[... | CC1(C=CCCCC(=O)O)Cc2c(cc(C(C)(C)C)c(O)c2C(C)(C)C)O1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | 24 | To a solution of 0.11 g of 6-(4,6-di-t-butyl-5-hydroxy-2-methyl-2,3-dihydrobenzofuran-2-yl)-5-hexenoic acid synthesized in Example 77 in 10 ml of ethyl acetate was added a catalytic amount of 10% palladium-carbon, and the mixture was stirred for 24 hours under a hydrogen atmosphere. After the catalyst was filtered off,... | CC1(CCCCCC(=O)O)Cc2c(cc(C(C)(C)C)c(O)c2C(C)(C)C)O1 | null | 90.4 | null |
1,193,785 | ord_dataset-4e81c470cc3b429faf5e1caa50f70a98 | null | 2012-01-01T00:08:00 | true | [N:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH3:16][CH:17]=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH2:16]([N:4]1[CH2:5][CH2:6][N:1]([C:7]2[CH:8]=[CH:9][C:10]([C:13](=[O:15])[CH3:14])=[CH:11][CH:12]=2)[CH2:2][CH2:3]1)[CH3:17] | CC(=O)c1ccc(N2CCNCC2)cc1 | CC=O | 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 | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 8 | A mixture of 1-(4-piperazin-1-yl-phenyl)-ethanone (500 mg, 2.45 mmol), CH3CHO (161 mg, 3.67 mmol) and NaBH(OAc)3 (778 mg, 3.67 mmol) in DCM (15 ml) was stirred at room temperature overnight. The resulting solution was partitioned between water and DCM and the organic phase was extracted with 1 M HCl. The aqueous layer ... | CCN1CCN(c2ccc(C(C)=O)cc2)CC1 | null | 43.9 | null |
1,363,896 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | [CH2:1]([O:3][C:4]([C:6]1([NH:9][C:10]2[N:15]=[C:14]([O:16][CH2:17][C:18]([F:21])([F:20])[F:19])[N:13]=[C:12]([NH:22][C:23]3[CH:35]=[CH:34][C:26]([C:27]([O:29]C(C)(C)C)=[O:28])=[CH:25][CH:24]=3)[N:11]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].C(O)(C(F)(F)F)=O>ClCCl>[CH2:1]([O:3][C:4]([C:6]1([NH:9][C:10]2[N:15]=[C:14]([O:16][CH2... | CCOC(=O)C1(Nc2nc(Nc3ccc(C(=O)OC(C)(C)C)cc3)nc(OCC(F)(F)F)n2)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 16 | To a suspension of tert-butyl 4-(4-(1-(ethoxycarbonyl)cyclopropylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoate (1.6 g) in dichloromethane (15 mL) was added TFA (4.96 mL). The mixture was stirred at r.t. for 16 hours. All solvents were removed under vacuum to give product 4-(4-(1-(ethoxycarbonyl)cycl... | CCOC(=O)C1(Nc2nc(Nc3ccc(C(=O)O)cc3)nc(OCC(F)(F)F)n2)CC1 | null | 95.1 | null |
1,707,537 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [O-:1][CH2:2][CH3:3].[Na+].[F:5][C:6]([F:16])([F:15])[C:7]1[N:12]=[C:11]([C:13]#[N:14])[CH:10]=[CH:9][CH:8]=1>C(O)C>[F:16][C:6]([F:15])([F:5])[C:7]1[N:12]=[C:11]([C:13](=[NH:14])[O:1][CH2:2][CH3:3])[CH:10]=[CH:9][CH:8]=1 | CC[O-] | N#Cc1cccc(C(F)(F)F)n1 | null | [Na+] | 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 | 2 | Sodium ethoxide (197 mg, 2.9 mmol) was added to a solution of 6-(trifluoromethyl)picolinonitrile (250 mg, 1.45 mmol) in ethanol (10 mL) at room temperature. The reaction mixture was stirred for 2 h. The solvent was removed under reduced pressure and the resulting residue was dissolved in dichloromethane, washed with wa... | CCOC(=N)c1cccc(C(F)(F)F)n1 | null | 92 | null |
1,086,291 | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | null | 2011-01-01T00:09:00 | true | N[C:2]1[C:3]([C:13]#[N:14])=[CH:4][C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[I:15]CI.N(OCCC(C)C)=O>C1COCC1.[Cu](I)I>[C:13]([C:3]1[C:2]([I:15])=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([CH3:12])[CH:4]=1)#[N:14] | COC(=O)c1cc(N)c(C#N)cc1C | ICI | null | I[Cu]I | CC(C)CCON=O | 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 | 85 | 3 | To a solution of methyl 5-amino-4-cyano-2-methylbenzoate (5.0 g, 0.0262 mol) in THF (100 mL) was added copper iodide (5.0 g, 0.0262 mol), diiodomethane (10.5 mL, 0.131 mol) and isoamyl nitrite (10.5 mL, 0.0786 mol). The reaction mixture was heated to 85° C. and stirred for 3 h, at which time it was cooled to room tempe... | COC(=O)c1cc(I)c(C#N)cc1C | null | 46.9 | null |
137,966 | ord_dataset-3fa0a6b7d51b4fc6a5380aa0d03ac884 | null | 1985-01-01T00:12:00 | true | B(Br)(Br)[Br:2].[Cl:5][C:6]1[C:7]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:8][C:9]([O:15]C)=[C:10]([CH2:12][CH2:13]O)[CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[Br:2][CH2:13][CH2:12][C:10]1[CH:11]=[C:6]([Cl:5])[C:7]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:8][C:9]=1[OH:15] | COc1cc(N2CCCCC2)c(Cl)cc1CCO | BrB(Br)Br | null | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 5 | 5.0 ml of boron tribromide are added dropwise over a period of approximately 5 minutes to a solution, cooled to 0°, of 2.70 g (10 mmole) of 2-[5-chloro-2-methoxy-4-(piperidin-1-yl)-phenyl]-ethanol in 70 ml of absolute methylene chloride. The reaction mixture is then stirred for a further 5 hours at room temperature, po... | Oc1cc(N2CCCCC2)c(Cl)cc1CCBr | null | null | null |
697,181 | ord_dataset-4e9c2fa02a7544fd839206719263345f | null | 2006-01-01T00:02:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:13]([C:14]([O-:16])=[O:15])=[C:12]([CH3:17])[NH:11][C:10]([CH3:18])=[C:9]2[C:19]([O:21][CH2:22][CH2:23][C:24]#[N:25])=[O:20])[CH:5]=[CH:6][CH:7]=1.[C:26]1([C:32]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[CH:33][CH2:34]O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.Cl.CN(C)CCCN=C=NCC... | OCC=C(c1ccccc1)c1ccccc1 | CC1=C(C(=O)[O-])C(c2cccc(Cl)c2)C(C(=O)OCCC#N)=C(C)N1 | null | CCN=C=NCCCN(C)C | CN(C)c1ccncc1 | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | ClCCl | null | null | null | null | null | null | null | null | null | null | null | 308 mg (0.85 mmol) of mono(2-cyanoethyl) 4-(3-chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, 348 mg (1.65 mmol) of 3,3-diphenyl-2-propene-1-ol, 260 mg (1.36 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 26 mg (0.21 mmol) of 4-dimethylaminopyridine were stirred together in 1... | CC1=C(C(=O)OCC=C(c2ccccc2)c2ccccc2)C(c2cccc(Cl)c2)C(C(=O)OCCC#N)=C(C)N1 | null | null | null |
168,419 | ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | null | 1988-01-01T00:02:00 | true | [F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH:16]=[CH:15][CH:14]=[CH:13]1)[N:8]([NH2:17])[CH:7]=[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:5]2=[O:23].[C:24](OC(=O)C)(=[O:26])C>C(O)=O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH:13]=[CH:14][CH:15]=[CH:16]1)[N:8]([NH:17][CH:24]=[O:26])[CH:7]=[C... | CCOC(=O)c1cn(N)c2cc(-n3cccc3)c(F)cc2c1=O | CC(=O)OC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=CO | null | null | null | null | null | null | null | null | null | null | 0 | null | A solution of 3.15 g (0.01 mol) of ethyl 6-fluoro-7-(pyrrol-1-yl)-1-amino-4-oxo-1,4-dihydroquinoline-3-carboxylate in 25 ml of formic acid is added dropwise to a mixture of 9.5 ml (0.01 mol) of acetic anhydride and 4 ml (0.01 mol) of formic acid, cooled to 0° C., the addition being carried out so as to maintain room te... | CCOC(=O)c1cn(NC=O)c2cc(-n3cccc3)c(F)cc2c1=O | null | null | null |
483,993 | ord_dataset-cb5c1a9eddff4790b1bd650617c32d34 | null | 2000-01-01T00:11:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH:9]2[OH:21])=[CH:4][CH:3]=1.[CH3:22][O:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Cl)=[CH:26][CH:25]=1.[H-].[Na+]>CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16]... | CC(C)(C)OC(=O)N1CCC(c2ccc(F)cc2)C(O)C1 | COc1ccc(CCl)cc1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | 3 | 200 mg (0.68 mmol) of tert-butyl (3RS,4RS)-4-(4-fluorophenyl)-3-hydroxy-piperidine-1-carboxylate and 159 mg (1.01 mmol) of 4-methoxybenzyl chloride were dissolved in 3 ml of dimethylformamide. 40 mg (1.01 mmol) of a 60% sodium hydride suspension were added and the mixture was stirred at room temperature for 3 hours. Su... | COc1ccc(COC2CN(C(=O)OC(C)(C)C)CCC2c2ccc(F)cc2)cc1 | null | 88.5 | null |
815,167 | ord_dataset-50f99930fc41474db226bc80774b38df | null | 2008-01-01T00:04:00 | true | [CH2:1]([N:8]([CH2:32][CH3:33])[C:9](=[O:31])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][O:20][C:21]2[CH:30]=[CH:29][CH:28]=[CH:27][C:22]=2[C:23]([O:25]C)=[O:24])=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+]>C1COCC1.O>[CH2:1]([N:8]([CH2:32][CH3:33])[C:9](=[O:31])[CH2:10][O:11][C... | CCN(Cc1ccccc1)C(=O)COc1ccc(CCOc2ccccc2C(=O)OC)cc1 | null | null | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | Methyl 2-[2-(4-{2-[benzyl(ethyl)amino]-2-oxoethoxy}phenyl)ethoxy]benzoate (0.138 g, 0.308 mmol) was dissolved in a mixture of THF/water (1/1, 4 ml). Lithium hydroxide (0.015 g, 0.617 mmol) was added. The reaction was performed in an single node microwave oven (14 min, 150 deg). Workup by removing the solvent by evapora... | CCN(Cc1ccccc1)C(=O)COc1ccc(CCOc2ccccc2C(=O)O)cc1 | null | 109.3 | null |
1,289,725 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][C:2]1=[O:7].C(N(CC)CC)C.[Cl:15][C:16]1[N:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>C(Cl)Cl>[Cl:15][C:16]1[N:21]=[CH:20][C:19]([S:22]([N:4]2[CH2:5][CH2:6][NH:1][C:2](=[O:7])[CH2:3]2)(=[O:24])=[O:23])=[CH:18][CH:17]=1 | O=S(=O)(Cl)c1ccc(Cl)nc1 | O=C1CNCCN1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 25 | 0.5 | To a mixture of 2-piperazinone (0.46 g, 4.59 mmol, Sigma-Aldrich, St. Louis, Mo.) and triethylamine (1.5 mL, 10.76 mmol) in CH2Cl2 (20 mL) at 0° C. was added 6-chloropyridine-3-sulfonyl chloride (0.974 g, 4.59 mmol, Organic Process Research & Development 2009, 13, 875). The resulting slurry was stirred at room temperat... | O=C1CN(S(=O)(=O)c2ccc(Cl)nc2)CCN1 | null | 88.5 | null |
576,121 | ord_dataset-f4512fe8cd804ac79da66cbc0c2b9d42 | null | 2002-01-01T00:12:00 | true | [CH3:1][C:2]1[CH:3]=[C:4]([CH2:11][S:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N+:15]=2[O-:20])=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].C(OO)(=[O:23])C>C(O)(=O)C>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:11][S:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N+:15]=2[O-:20])(=[O:23])=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[... | CC(=O)OO | Cc1cc(CS(=O)c2cccc[n+]2[O-])ccc1[N+](=O)[O-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | 25 | null | To a mixture of 9.5 g of 2-[[(3-methyl-4-nitrophenyl)methyl]sulfinyl]-pyridine-1-oxide in 50 ml of acetic acid was added, dropwise with stirring at room temperature, 9.17 g of 40% peracetic acid in acetic acid. After addition, a short period of heating was required to complete the reaction. Excess peracetic acid was th... | Cc1cc(CS(=O)(=O)c2cccc[n+]2[O-])ccc1[N+](=O)[O-] | null | null | null |
548,149 | ord_dataset-e967d076b4894c2c854795f019ed3c39 | null | 2002-01-01T00:06:00 | true | [C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].C[Al](C)C.CCCCCC.[C:32]([C:34]1[CH:35]=[C:36](/[C:40](/[CH:46]([CH3:48])[CH3:47])=[CH:41]\[C:42](OC)=[O:43])[CH:37]=[CH:38][CH:39]=1)#[N:33]>ClCCl>[C:1]([NH:5][S... | CC(C)(C)NS(=O)(=O)c1ccccc1-c1ccc(N)cc1 | COC(=O)/C=C(\c1cccc(C#N)c1)C(C)C | null | C[Al](C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCCCCC | null | null | null | null | null | null | null | null | null | 25 | 8 | To a solution of 2′-tert-butylaminosulfonyl-4-amino-[1,1′]-biphenyl (139 mg, 0.46 mmol) in 4 ml anhydrous dichloromethane was added a solution of 2M trimethylaluminum in hexane (0.69 ml, 1.38 mmol). Reaction was stirred at room temperature for 20 minutes to which a solution of crude methyl (2Z)-3-(3-cyanophenyl)-4-meth... | CC(C)/C(=C/C(=O)Nc1ccc(-c2ccccc2S(=O)(=O)NC(C)(C)C)cc1)c1cccc(C#N)c1 | null | 82.3 | null |
1,092,340 | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | null | 2011-01-01T00:09:00 | true | Cl[C:2]1[N:7]=[CH:6][C:5]([N:8]2[C:12]3[N:13]=[C:14]([N:42]4[CH2:47][CH2:46][O:45][CH2:44][CH2:43]4)[N:15]=[C:16]([C:17]4[CH:18]=[N:19][C:20]([N:23]([CH2:33][C:34]5[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=5)[CH2:24][C:25]5[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=5)=[N:21][CH:22]=4)[C:11]=3[CH2:1... | CN1CCNCC1 | COc1ccc(CN(Cc2ccc(OC)cc2)c2ncc(-c3nc(N4CCOCC4)nc4c3CCN4c3ccc(Cl)nc3)cn2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Using {5-[7-(6-chloro-pyridin-3-yl)-2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl]-pyrimidin-2-yl}-bis-(4-methoxy-benzyl)-amine (200 mg, 0.31 mmol) obtained in Step A in Example 1-D-48 and N-methylpiperazine (46 mg, 0.46 mmol) instead of N,N,N′-trimethyl ethylenediamine, in the same manner as Example 1-D... | COc1ccc(CN(Cc2ccc(OC)cc2)c2ncc(-c3nc(N4CCOCC4)nc4c3CCN4c3ccc(N4CCN(C)CC4)nc3)cn2)cc1 | null | 99.3 | null |
444,852 | ord_dataset-ba7561dae3884c07a8beddd0b9f1222e | null | 1999-01-01T00:10:00 | true | [CH2:1]([O:8][C:9]([N:11]1[C:19]2[CH:18]=[C:17]3[CH:20]([CH2:23][C:24]([OH:26])=O)[CH2:21][O:22][C:16]3=[CH:15][C:14]=2[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:27]([N:29](CC)[CH2:30]C)C.ClC(OCC)=O>ClCCl>[CH2:1]([O:8][C:9]([N:11]1[C:19]2[CH:18]=[C:17]3[CH:20]([CH2:23][C:24]([N:29]([CH3:30]... | O=C(O)CC1COc2cc3c(cc21)N(C(=O)OCc1ccccc1)CC3 | CCN(CC)CC | null | CCOC(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | 2 | 5-(Benzyloxycarbonyl)-2,3,6,7-tetrahydrofuro[2,3-f]indol-3-ylacetic acid (D22, 0.89 g, 2.5 mmol) and triethylamine (0.7 ml, 5 mmol) were stirred in dichloromethane (80 ml) under Ar at 0° C. as ethyl chloroformate (0.27 ml, 92.8 mmol) was added. The mixture was stirred for 2 h, and dimethylamine gas was then bubbled thr... | CN(C)C(=O)CC1COc2cc3c(cc21)N(C(=O)OCc1ccccc1)CC3 | null | 46.3 | null |
234,784 | ord_dataset-45d20d09e4d64f45bdd419044025b4d3 | null | 1991-01-01T00:09:00 | true | Cl.[CH3:2][C:3]1[C:12]([CH2:13][CH2:14]Cl)=[C:11](Cl)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[CH3:17][O:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[C:21]([CH3:26])[CH:20]=1>C(O)C>[CH3:17][O:18][C:19]1[CH:25]=[CH:24][C:22]([N:23]2[C:11]3[C:10]4[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=4[N:4]=[C:3]([CH3:2])[C:12]=3[CH2:13... | Cc1nc2ccccc2c(Cl)c1CCCl | COc1ccc(N)c(C)c1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | 2-Methyl-3-(2-chloroethyl)-4-chloroquinoline hydrochloride (5.53 g, 20 mmol) and 4-methoxy-2-methylaniline (5.15 ml, 40 mmol) in ethanol (100 ml)were heated at 170° C. in a pressure vessel for 24 hours, then the solvent evaporated, the crude product taken up in dichloromethane, washed with aqueous sodium bicarbonate, d... | COc1ccc(N2CCc3c(C)nc4ccccc4c32)c(C)c1 | null | 33.5 | null |
105,133 | ord_dataset-4ac1b977dc504cb5a6a8e85d7d777c45 | null | 1983-01-01T00:05:00 | true | [CH2:1]([NH:10][CH3:11])/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[CH2:13][C:14]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[O:17][CH2:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[O:17]1[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:14]([CH2:13][N:10]([CH2:1]/[CH:2]=[CH:3]/[C:4]2[CH:9]=[CH:8][C... | ClCC1=CCOc2ccccc21 | CNC/C=C/c1ccccc1 | 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 | null | null | null | null | null | null | null | null | null | null | null | 24 | 1.15 g of trans-N-cinnamyl-methylamine in 20 ml of dimethylformamide are slowly added dropwise with stirring to 1.4 g of 4-chloromethyl-2H-1-benzopyrane and 0.8 g of sodium carbonate in 40 ml dimethylformamide. Stirring is continued for 24 hours at room temperature, the resulting mixture evaporated under vacuum and the... | CN(C/C=C/c1ccccc1)CC1=CCOc2ccccc21 | null | null | null |
1,632,045 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:8][C:9]1[CH:23]=[CH:22][C:12]([CH2:13][NH:14]C(=O)OC(C)(C)C)=[C:11]([CH2:24][NH:25][C:26]([C@@H:28]2[CH2:33][O:32][CH2:31][CH2:30][N:29]2[C:34](=[O:41])[C@H:35]([OH:40])[C:36]([CH3:39])([CH3:38])[CH3:37])=[O:27])[CH:10]=1>C(Cl)Cl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4... | CC(C)(C)OC(=O)NCc1ccc(Cl)cc1CNC(=O)[C@@H]1COCCN1C(=O)[C@H](O)C(C)(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | 0 | 0.5 | Trifluoroacetic acid (50% solution in CH2Cl2, 3 mL) was added to a solution of tert-Butyl 4-chloro-2-[{(S)-4-{(R)-2-hydroxy-3,3-dimethylbutanoyl}morpholine-3-carboxamido}-methyl]-benzylcarbamate (0.25 g, 0.50 mmol) in CH2Cl2 (1 mL) and the reaction was stirred at 0° C. for 30 min. The reaction mixture was concentrated ... | CC(C)(C)[C@@H](O)C(=O)N1CCOC[C@H]1C(=O)NCc1cc(Cl)ccc1CN | null | null | null |
790,538 | ord_dataset-530502f8e61e455784f93c5faa45c94b | null | 2007-01-01T00:09:00 | true | [OH:1][CH2:2][CH2:3][O:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[C:9]#[N:10].C(N(C(C)C)CC)(C)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>ClCCl>[CH3:23][S:24]([O:1][CH2:2][CH2:3][O:4][CH2:5][C:6]1[CH:13]=[CH:12][CH:11]=[C:8]([C:9]#[N:10])[CH:7]=1)(=[O:26])=[O:25] | N#Cc1cccc(COCCO)c1 | CS(=O)(=O)Cl | 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 | null | 2 | To a solution of 3-[(2-hydroxyethoxy)methyl]benzonitrile (example 28vi) (6.00 g) and diisopropylethylamine (11.8 ml) in dichloromethane (100 ml) at 0° C. was added methanesulphonyl chloride (3.14 ml) dropwise and the mixture allowed to stir for 2 h. The resultant mixture was partitioned between dichloromethane and satu... | CS(=O)(=O)OCCOCc1cccc(C#N)c1 | null | null | null |
1,466,209 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH:13]3[CH2:18][CH2:17][CH:16]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:15][CH2:14]3)[CH:8]=2)[CH:3]=1.C([Li])CCC.CCCCCC.Br[CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37]>CCOCC>[CH2:39]([O:38][C:36](=[O:37])[CH2:35][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]... | CC(C)(C)C1CCC(Oc2ccc3cc(Br)ccc3c2)CC1 | CCOC(=O)CBr | null | [Li]CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCCCC | CCOCC | null | null | null | null | null | null | null | null | null | 0 | 0.5 | A solution of 2-bromo-6-(4-tert-butyl-cyclohexyloxy)-naphthalene (2 g, 5.5 mmol) in ether (10 mL) under nitrogen was added 1.6 M n-butyllithium in hexane (4 mL, 6.4 mmol) at 0° C. The solution was stirred for 30 min at 0° C., then treated with copper(I) bromide-dimethyl sulfide complex (0.8 g, 3.9 mmol). After 2 hrs st... | CCOC(=O)Cc1ccc2cc(OC3CCC(C(C)(C)C)CC3)ccc2c1 | null | 22.2 | null |
290,836 | ord_dataset-5fb693db3950403e9ce1a516570153bf | null | 1994-01-01T00:05:00 | true | [Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][S:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]=NCCCC.C(OC(=O)C)(=O)C.[N+:26]([CH2:29][C:30](=[O:32])[CH3:31])([O-:28])=[O:27]>C1C=CC=CC=1>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][S:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]=[C:29]([N+:26]([O-:28])=[O:27])[C:30](=[O:32])[CH3:... | CCCCN=Cc1ccccc1SCCCCCl | CC(=O)C[N+](=O)[O-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccccc1 | CC(=O)OC(C)=O | null | null | null | null | null | null | null | null | null | 25 | 8 | To a 2 liter 4-neck round-bottom flask fitted with mechanical stirrer and thermowell, under a nitrogen atmosphere, was added 138.2 g of N-{2-[(4-chlorobutyl)thio]phenylmethylene}-1-butanamine and 350 ml of benzene, followed by 91.9 ml of acetic anhydride. The mixture was cooled in an ice water bath as 50.18 g of nitroa... | CC(=O)C(=Cc1ccccc1SCCCCCl)[N+](=O)[O-] | null | null | null |
548,896 | ord_dataset-e967d076b4894c2c854795f019ed3c39 | null | 2002-01-01T00:06:00 | true | [CH2:1]([O:8][C:9]([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][C@H:12]1[C:20]([OH:22])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23]([NH2:26])[CH2:24][CH3:25]>>[CH2:23]([NH:26][C:20]([C@@H:12]1[CH2:13][C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:11]1[C:9]([O:8][CH2:1][C:2]1[CH:7]=[... | O=C(O)[C@@H]1Cc2ccccc2N1C(=O)OCc1ccccc1 | CCCN | null | null | null | null | null | null | null | 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 process is performed as in Example 14 a), starting with N-benzyloxycarbonyl-2(S)-indolinecarboxylic acid prepared as in Example 16 a) and n-propylamine. A white solid is obtained, which is recrystallized from CCl4. | CCCNC(=O)[C@@H]1Cc2ccccc2N1C(=O)OCc1ccccc1 | null | null | null |
1,026,358 | ord_dataset-83acb82dc5ba4f7aba439b9875aaac43 | null | 2011-01-01T00:02:00 | true | [I:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:4][CH:3]=1.[H-].[Na+].I[CH:18]([CH3:20])[CH3:19].O>CN(C=O)C>[I:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH:18]([CH3:20])[CH3:19])[C:9]2[N:10]=[CH:11][CH:12]=[CH:13][N:14]=2)=[CH:6][CH:7]=1 | Ic1ccc(Nc2ncccn2)cc1 | CC(C)I | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 1.33 | Under an argon atmosphere, a solution of N-(4-iodophenyl)pyrimidin-2-amine (8.00 g) in anhydrous DMF (50 ml) was added dropwise to a suspension of sodium hydride (1.08 g) in anhydrous DMF (200 ml), and the resulting mixture was stirred at room temperature for 80 minutes. To the reaction solution, 2-iodopropane (4.03 ml... | CC(C)N(c1ccc(I)cc1)c1ncccn1 | null | null | null |
849,638 | ord_dataset-171b840ae6e84e45bab43b987d09f5c7 | null | 2008-01-01T00:11:00 | true | [F:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][C:7]2[C:20](=[O:21])[N:19]([CH3:22])[C:10]3[N:11]=[C:12](S(C)(=O)=O)[N:13]=[CH:14][C:9]=3[CH:8]=2)=[CH:4][CH:3]=1.[F:25][C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=1.CO>CN1CCCC1=O>[F:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][C:7]2[C:20](=[O:21])[N:19]([CH3:22])[C:10]3[N:11]=[C:1... | Cn1c(=O)c(Oc2ccc(F)cc2)cc2cnc(S(C)(=O)=O)nc21 | Nc1ccc(F)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN1CCCC1=O | CO | null | null | null | null | null | null | null | null | null | 110 | 12 | A mixture of 6-(4-fluorophenoxy)-8-methyl-2-(methylsulfonyl)pyrido[2,3-d]pyrimidin-7(8H)-one (see Example 8 replacing methyl 2-fluorophenoxyacetate with methyl 4-fluorophenoxyacetate-Step A-B, 0.35 g, 1 mmol) and 4-fluoroaniline (0.284 mL, 3 mmol) in 0.5 mL 1-methyl-2-pyrrolidinone was stirred at 110° C. for 12 hours a... | Cn1c(=O)c(Oc2ccc(F)cc2)cc2cnc(Nc3ccc(F)cc3)nc21 | null | null | null |
693,614 | ord_dataset-35824232b132464aa99e71aba765981d | null | 2005-01-01T00:12:00 | true | [C:1]1([C:7]#[C:8][C:9]2[CH:10]=[C:11]([C:15]([OH:17])=O)[CH:12]=[N:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[C:51]([O:55][C:56]([N:58]([CH2:66][C:67]1[CH:68]=[C:69]([CH:73]2[CH2:78][CH2:77][NH:76][CH2:75][CH2:74]2)[CH:70]=[CH:71][CH:72]=... | O=C(O)c1cncc(C#Cc2ccccc2)c1 | CC(C)(C)OC(=O)N(Cc1cccc(C2CCNCC2)c1)C(=O)OC(C)(C)C | null | CN(C)C(On1nnc2cccnc21)=[N+](C)C | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 25 | 0.25 | A solution of 5-phenylethynyl-pyridine-3-carboxylic acid (0.25 g, 1.1 mmol) in anhydrous dimethylformamide (5 ml) was treated with O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (0.42 g, 1.1 mmol) and diisopropylethylamine (0.5 ml, 3 mmol). This mixture was stirred 15 minutes at ambient tempe... | CC(C)(C)OC(=O)N(Cc1cccc(C2CCN(C(=O)c3cncc(C#Cc4ccccc4)c3)CC2)c1)C(=O)OC(C)(C)C | null | 42 | null |
1,420,270 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH:13]3[O:18][CH2:17][CH2:16][NH:15][CH2:14]3)[NH:11][CH:12]=2)=[CH:4][CH:3]=1.[Cl:19][C:20]1[CH:25]=[C:24](Cl)[N:23]=[C:22]([NH2:27])[N:21]=1.CCN(C(C)C)C(C)C>C(O)C>[Cl:19][C:20]1[CH:25]=[C:24]([N:15]2[CH2:16][CH2:17][O:18][CH:13]([C:10]3[NH:11][CH:12]=[C:8]([C:5]4[CH:... | Clc1ccc(-c2c[nH]c(C3CNCCO3)n2)cc1 | Nc1nc(Cl)cc(Cl)n1 | 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 | CCO | null | null | null | null | null | null | null | null | null | null | null | A solution of 2-[4-(4-chlorophenyl)-1H-imidazol-2-yl]morpholine (322 mg, 1.22 mmol), 4,6-dichloro-2-pyrimidinamine (200 mg, 1.220 mmol) and Hunig's base (531 μL, 3.05 mmol) in ethanol (6.1 mL) was heated at 85° C. overnight. The mixture was evaporated and chromatographed (PE-EtOAc, 2:3) to afford the title compound (22... | Nc1nc(Cl)cc(N2CCOC(c3nc(-c4ccc(Cl)cc4)c[nH]3)C2)n1 | null | 46.1 | null |
1,515,938 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | [Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8](C(Cl)(Cl)Cl)[N:7]([C:14]3[CH:19]=[CH:18][N:17]=[C:16]([NH2:20])[N:15]=3)[C:6]=2[CH:21]=1.[CH2:22]([OH:25])[CH2:23][OH:24].C(=O)([O-])[O-].[Cs+].[Cs+]>O>[NH2:20][C:16]1[N:15]=[C:14]([N:7]2[C:6]3[CH:21]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=3[N:9]=[C:8]2[O:24][CH2:23][CH2:22][OH:25])[... | OCCO | Nc1nccc(-n2c(C(Cl)(Cl)Cl)nc3ccc(Br)cc32)n1 | null | O=C([O-])[O-] | [Cs+] | 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 | 25 | 8 | A mixture of 4-[6-bromo-2-(trichloromethyl)-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine (1 g, 2.45 mmol), ethane-1,2-diol (15 mL) and cesium carbonate (3 g, 9.18 mmol) was stirred overnight at room temperature and then diluted with 200 mL of water. The resulting solution was extracted with 2×200 mL of dichloromethane. Th... | Nc1nccc(-n2c(OCCO)nc3ccc(Br)cc32)n1 | null | 34 | null |
545,475 | ord_dataset-d31180f42ced44719fd9e72685c798bf | null | 2002-01-01T00:05:00 | true | Br[CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:11])[CH:8]=2)[C:3]1=[O:12].[C:13]([C:17]1[CH:27]=[CH:26][C:20]([O:21][CH2:22][C:23]([NH2:25])=[S:24])=[CH:19][CH:18]=1)([CH3:16])([CH3:15])[CH3:14]>CC(C)=O>[C:13]([C:17]1[CH:27]=[CH:26][C:20]([O:21][CH2:22][C:23]2[S:24][CH:2]3[CH2:10][C:9]4[CH:8]=[C:7]([Cl:11])[CH:6]... | CC(C)(C)c1ccc(OCC(N)=S)cc1 | O=C1c2ccc(Cl)cc2CC1Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | null | null | null | null | null | null | null | null | null | null | 25 | 12 | At room temperature, 0.49 g of 2-bromo-5-chlorindan-1-on and 0.45 g of 2-(4-tert-butylphenoxy)-thioacetamide were dissolved in 10 ml of dry acetone, and the mixture was stirred at room temperature for 12 h. The precipitated hydrobromide was filtered off with suction and washed with acetone. The residue was suspended in... | CC(C)(C)c1ccc(OCC2=NC3(O)c4ccc(Cl)cc4CC3S2)cc1 | null | null | null |
1,610,796 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:12][C@@:11]([CH2:14][N:15]=[N+:16]=[N-:17])(O)[CH2:10][C@H:9]1[C:18](=[O:29])[NH:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:22]=1[F:28])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(S(F)(F)[F:36])CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@:11]([CH2:14][N:15]=[N+:1... | CCN(CC)S(F)(F)F | CC(C)(C)OC(=O)N1C[C@](O)(CN=[N+]=[N-])C[C@H]1C(=O)NCc1cccc(Cl)c1F | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 1.5 | To a solution of (2S,4S)-4-azidomethyl-2-(3-chloro-2-fluoro-benzylcarbamoyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (430 mg, 1.0 mmol) in CH2Cl2 (25 mL) under N2 atmosphere at −78° C. was added DAST (266 μL, 2.01 mmol). The reaction mixture was allowed to warm up to RT and further stirred for 1.5 h. T... | CC(C)(C)OC(=O)N1C[C@@](F)(CN=[N+]=[N-])C[C@H]1C(=O)NCc1cccc(Cl)c1F | null | null | null |
656,674 | ord_dataset-f5d908a6dcb44353a706166b5e9f7f88 | null | 2004-01-01T00:12:00 | true | [C:1]1([S:7][C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[CH:11]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C@@H:16]1([NH2:26])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][CH2:18][CH2:17]1>>[C:1]1([S:7][C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[CH2:11][NH:26][C@@H:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:2... | N[C@H]1CCCc2ccccc21 | O=Cc1cccc(Sc2ccccc2)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The product from Example 71A and (1S)-1,2,3,4-tetrahydro-1-naphthalenylamine were processed as described in Example 1A to provide the title compound as a clear oil. (1.06 g, 46%). | c1ccc(Sc2cccc(CN[C@H]3CCCc4ccccc43)c2)cc1 | null | null | null |
742,456 | ord_dataset-437aa6654d5044ddaef3346dc4c6e08a | null | 2006-01-01T00:11:00 | true | [Si:1]([O:8][C@H:9]([C:36]1[CH:41]=[CH:40][C:39]([OH:42])=[C:38]([CH2:43][OH:44])[CH:37]=1)[CH2:10][NH:11][C@H:12]([CH3:35])[CH2:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[NH:19][C:18]([C:23]([NH:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[O:33][CH3:34])=[O:24])=[CH:17]2)([C:4]([CH3:7])([CH3:6])[CH... | COc1ccccc1CNC(=O)c1cc2cc(C[C@@H](C)NC[C@H](O[Si](C)(C)C(C)(C)C)c3ccc(O)c(CO)c3)ccc2[nH]1 | COc1cccc(OC)c1CN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared analogously to 5-[(2R)-2-({(2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)propyl]-N-(2-methoxybenzyl)-1H-indole-2-carboxamide using 2,6-dimethoxybenzylamine to give the title compound as a pale yellow foam. | COc1cccc(OC)c1CNC(=O)c1cc2cc(C[C@@H](C)NC[C@H](O[Si](C)(C)C(C)(C)C)c3ccc(O)c(CO)c3)ccc2[nH]1 | null | null | null |
706,488 | ord_dataset-c8069773c1a148aca8ab417108daacc5 | null | 2006-01-01T00:05:00 | true | CCN=C=NCCCN(C)C.[CH2:12]([O:14][CH2:15][C:16]([OH:18])=O)[CH3:13].Br.[NH2:20][C:21]1[S:22][C:23]([Br:26])=[CH:24][N:25]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[Br:26][C:23]1[S:22][C:21]([NH:20][C:16](=[O:18])[CH2:15][O:14][CH2:12][CH3:13])=[N:25][CH:24]=1 | Nc1ncc(Br)s1 | CCOCC(=O)O | null | Br | CCN=C=NCCCN(C)C | 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 | null | 1 | EDCI (0.53 g, 2.78 mmol) was added to a solution of ethoxyacetic acid (0.29 g, 2.78 mmol) in CH2Cl2 (5 ml) under ice-cooling. After stirring for 1 h, a solution of 2-amino-5-bromothiazole hydrobromide (0.60 g, 2.31 mmol) and diisopropylethylamine (0.40 ml, 2.34 mmol) in CH2Cl2 (5 ml) was added dropwise, and the entire ... | CCOCC(=O)Nc1ncc(Br)s1 | null | 70.2 | null |
62,860 | ord_dataset-9240b22758dd4f9e981f9ad2d5394155 | null | 1980-01-01T00:02:00 | true | Br.[NH2:2][C@H:3]([C:5]([N:7]1[CH2:20][CH2:19][CH2:18][C@H:8]1[C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:10])=[O:6])[CH3:4].[C:21](OC(=O)C)(=[O:23])[CH3:22]>N1C=CC=CC=1>[C:21]([NH:2][C@H:3]([C:5]([N:7]1[CH2:20][CH2:19][CH2:18][C@H:8]1[C:9]([NH:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:1... | CC(=O)OC(C)=O | C[C@H](N)C(=O)N1CCC[C@H]1C(=O)Nc1ccccc1 | null | Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | 25 | 1 | 2 g (0.00585 mol) of L-alanyl-L-proline anilide hydrobromide were dissolved in 40 ml of dry pyridine and 1.1 ml (0.0117 mol) of acetic anhydride were added. The solution was stirred at room temperature for 1 hour and then evaporated. Final traces of pyridine were removed by addition of 20 ml of toluene ane re-evaporati... | CC(=O)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)Nc1ccccc1 | null | 92.4 | null |
344,007 | ord_dataset-d0003732f14e4648a00d341275654590 | null | 1996-01-01T00:11:00 | true | [CH:1]1[CH:6]=[C:5]2[C:7]([C:9](O)(O)[C:10](=[O:11])[C:4]2=[CH:3][CH:2]=1)=[O:8].Cl.[CH2:15]([O:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH3:26])=[CH:20][C:19]=1[NH:27][C:28](=[O:31])[NH:29][NH2:30])[CH3:16]>>[CH2:15]([O:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH3:26])=[CH:20][C:19]=1[NH:27][C:28](=[O:31])... | O=C1c2ccccc2C(=O)C1(O)O | CCOc1ccc(OCC)c(NC(=O)NN)c1 | 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 | ninhydrin, 4-(2,5-diethoxyphenyl)-semicarbazide hydrochloride | CCOc1ccc(OCC)c(NC(=O)NN=c2c(=O)c3ccccc3c2=O)c1 | null | null | null |
1,725,027 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | [NH2:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH2:3]1.Cl[C:17]1[N:22]=[CH:21][CH:20]=[CH:19][N:18]=1>CN(C=O)C.CCOC(C)=O>[N:18]1[CH:19]=[CH:20][CH:21]=[N:22][C:17]=1[NH:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:1... | CC(C)(C)OC(=O)N[C@H]1CC[C@@H](N)CC1 | Clc1ncccn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | As shown in step 5-i of Scheme 5, a mixture of tert-butyl ((cis)-4-aminocyclohexyl)carbamate (compound 1009, 490 mg, 2.3 mmol), 2-chloropyrimidine (262 mg, 2.3 mmol) and TEA (463 mg, 637θL, 4.6 mmol) in DMF (10 mL) was subjected to microwave irradiation for 20 minutes at 150° C. The reaction mixture was diluted with Et... | CC(C)(C)OC(=O)N[C@H]1CC[C@@H](Nc2ncccn2)CC1 | null | null | null |
1,477,239 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([C:22]([O:24]CC)=O)[O:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.C([NH2:29])=O.C[O-].[Na+]>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([C:22]([NH2:29])=[O:24])[O:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([... | NC=O | CCOC(=O)c1nc(-c2ccc(OC)cc2)c(-c2ccc(OC)cc2)o1 | null | C[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In WO2004/065374 is disclosed a method in which ethyl 4,5-bis(4-methoxyphenyl)-1,3-oxazole-2-carboxylate, which is a carboxylic acid ester, is allowed to react with formamide in the presence of sodium methoxide, which is a metal alkoxide, to give 4,5-bis(4-methoxyphenyl)-1,3-oxazole-2-carboxamide, which is a carboxamid... | COc1ccc(-c2nc(C(N)=O)oc2-c2ccc(OC)cc2)cc1 | null | 71.9 | null |
412,669 | ord_dataset-fbdd058349aa456f812e3546c84baab5 | null | 1998-01-01T00:09:00 | true | C([Li])(C)(C)C.[C:6]([SiH2:10][O:11][C:12]([CH3:29])([CH3:28])[C:13]1[C:26]2[S:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]([CH3:27])[C:17]=2[CH:16]=[CH:15][CH:14]=1)([CH3:9])([CH3:8])[CH3:7].CN(C)CCN(C)C.[CH:38](N1CCCCC1)=[O:39].Cl>C(OCC)C>[C:6]([SiH2:10][O:11][C:12]([CH3:29])([CH3:28])[C:13]1[CH:14]=[CH:1... | O=CN1CCCCC1 | CN1c2ccccc2Sc2c1cccc2C(C)(C)O[SiH2]C(C)(C)C | null | CN(C)CCN(C)C | Cl | [Li]C(C)(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | 0 | 0.5 | 36.4 ml of tert-butyllithium solution (1.4M in pentane) were slowly added dropwise under argon at -78° to a solution of 14.0 g (39.2 mmol) of 4-(tert-butyl-dimethyl-silanyloxymethyl)-10-methyl-phenothiazine and 6.39 ml of N,N,N',N'-tetramethylethylenediamine in 120 ml of diethyl ether. The reaction mixture was stirred ... | CN1c2cccc(CO)c2Sc2c1cccc2C(C)(C)O[SiH2]C(C)(C)C | null | 30.1 | null |
670,352 | ord_dataset-e90cd41afe844e49875435eb99903799 | null | 2005-01-01T00:05:00 | true | [F:1][C:2]1[C:3]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][OH:21])=[CH:15][C:14]=2[F:22])=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([OH:7])=O.[NH2:23][O:24][CH2:25][CH2:26][OH:27].C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-]>CO>[F:1][C:2]1[C:3]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][OH:21])=[CH:15][C:... | NOCCO | O=C(O)c1ccc(F)c(F)c1Nc1ccc(CCO)cc1F | null | COc1nc(OC)nc([N+]2(C)CCOCC2)n1 | [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 | 3,4-Difluoro-2-[2-fluoro-4-(2-hydroxyethyl)anilino]benzoic acid was dissolved in MeOH and prepared from reaction with 2(aminooxy)ethanol and DMT-MM by the general procedure of Example 6, Step B, affording a crude yellow oil after workup which was purified by filtration through a plug of silica gel (100% EtOAc as eluant... | O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(CCO)cc1F | null | null | null |
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