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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
1,396,313 | ord_dataset-12dc3bd21bcf44d09e5b4249afe15161 | null | 2014-01-01T00:02:00 | true | Cl.Cl[C:3]1[N:8]=[C:7]([C:9]2([C:13]([OH:15])=O)[CH2:12][CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=1.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][NH2:26])=[CH:20][CH:19]=1.Cl.C(N=C=NCCCN(C)C)C>ClCCl.CN(C)C1C=CN=CC=1>[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][NH:26][C:13]([C:9]2([C:7]3[CH:6]=[... | O=C(O)C1(c2cccc(Cl)n2)CCC1 | COc1ccc(CCN)cc1 | null | CCN=C=NCCCN(C)C | CN(C)c1ccncc1 | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 0.5 | 1-(6-Chloropyridin-2-yl)cyclobutanecarboxylic acid hydrochloride (2.6 g, 10.48 mmol) was suspended in dichloromethane (30 ml). 2-(4-Methoxyphenyl)ethanamine (1.743 g, 11.53 mmol) and 4-dimethylaminopyridine (2.56 g, 20.96 mmol) were added and stirring at room temperature was continued for 30 min. The reaction mixture w... | COc1ccc(CCNC(=O)C2(c3ccccn3)CCC2)cc1 | null | null | null |
1,389,378 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | [CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:9][C:10]1[CH:11]=[C:12]2[C:17](=[C:18]([C:20]([NH2:22])=[O:21])[CH:19]=1)[N:16]=[CH:15][N:14]=[C:13]2[NH:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([C:32]([F:35])([F:34])[F:33])[CH:26]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(Cl)Cl>[CH2:1]([NH:9][C:10]1[CH:11... | NC(=O)c1cc(N)cc2c(NCc3ccc(Cl)c(C(F)(F)F)c3)ncnc12 | BrCc1ccccc1 | null | O=C([O-])[O-] | [Cs+] | 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 | 50 | 8 | Benzylbromide (140 μL, 0.5 M in anhydrous DCM, 0.07 mmol, 1.1 equiv.) was added to a solution of 6-amino-4-{[4-chloro-3-(trifluoromethyl)benzyl]amino}quinazoline-8-carboxamide (25 mg, 0.06 mmol, 1.0 equiv.) and cesium carbonate (62 mg, 0.19 mmol, 3.0 equiv.) in anhydrous DCM (2 mL). The resulting mixture was stirred at... | NC(=O)c1cc(NCc2ccccc2)cc2c(NCc3ccc(Cl)c(C(F)(F)F)c3)ncnc12 | null | 17 | null |
28,967 | ord_dataset-2cb52357eb5f43c2be56ad5c0662f18f | null | 1977-01-01T00:08:00 | true | [CH3:1][N:2]([CH3:7])[S:3](Cl)(=[O:5])=[O:4].[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][CH:10]=1.C>N1C=CC=CC=1>[C:15]([C:12]1[CH:13]=[CH:14][C:9]([NH:8][S:3]([N:2]([CH3:7])[CH3:1])(=[O:5])=[O:4])=[CH:10][CH:11]=1)(=[O:17])[CH3:16] | CC(=O)c1ccc(N)cc1 | CN(C)S(=O)(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | 25 | 8 | Dimethylsulfamoyl chloride (14.4 g., 0.10 mole) is added dropwise to p-aminoacetophenone (13.5 g., 0.10 mole) in pyridine (60 ml.) at 10°-15° C. The mixture is stirred at room temperature overnight and then added to excess 6N HC1 to give 14.1 g. (58%) of solid. The solid is dissolved in base, treated with charcoal, rep... | CC(=O)c1ccc(NS(=O)(=O)N(C)C)cc1 | null | null | null |
891,799 | ord_dataset-11068b1e475b4c5b82e56726ab0dddb7 | null | 2009-01-01T00:07:00 | true | [CH2:1]([O:8][C:9]([N:11]([CH2:32][C:33]([N:35]1[CH2:39][C@@H:38]([F:40])[CH2:37][C@H:36]1[C:41]#[N:42])=[O:34])[C:12]12[CH2:19][CH2:18][C:15]([C:20](ON3C4C=CC=CC=4N=N3)=[O:21])([CH2:16][CH2:17]1)[CH2:14][CH2:13]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:43]([CH:50]1[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]1... | c1ccc(CC2CCNCC2)cc1 | N#C[C@@H]1C[C@H](F)CN1C(=O)CN(C(=O)OCc1ccccc1)C12CCC(C(=O)On3nnc4ccccc43)(CC1)CC2 | null | null | null | null | null | null | null | 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 similar manner to Example 4, (2S,4S)-1-[[N-benzyloxycarbonyl-N-[4-(benzotriazol-1-yl)oxycarbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (50.0 mg) and 4-benzylpiperidine (22.9 μL) were used to obtain (2S,4S)-1-[[N-benzyloxycarbonyl-N-[4-(4-benzylpiperidin-1-yl)carbonylbicyclo[2.2.2]o... | N#C[C@@H]1C[C@H](F)CN1C(=O)CN(C(=O)OCc1ccccc1)C12CCC(C(=O)N3CCC(Cc4ccccc4)CC3)(CC1)CC2 | null | null | null |
122,338 | ord_dataset-a9b95e50436441ff8f3f12dd60d1e1b2 | null | 1984-01-01T00:10:00 | true | [OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:11][CH3:12])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[CH2:20][CH2:21][CH3:22].CN(C)C=O>O>[CH2:19]([O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:11][CH3:12])[CH:3]=1)[CH2:20][CH2:21][CH3:22] | CCCCBr | COc1cc(O)ccc1C(=O)O | 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 mixture of 4.2 g. (0.025 mole) of 4-hydroxy-2-methoxybenzoic acid, 7 g. of potassium carbonate, and 10 g. of n-butyl bromide in 100 ml. of N,N-dimethylformamide was heated at 70° C. for 24 hours. The mixture was cooled, diluted with water and extracted with diethyl ether. The ether extracts were washed with dilute so... | CCCCOc1ccc(C(=O)O)c(OC)c1 | null | null | null |
386,270 | ord_dataset-d330662edaed408d950898172aba7a4c | null | 1997-01-01T00:12:00 | true | [OH:1][CH2:2][C:3]([O:5][CH2:6][CH2:7][CH2:8][CH3:9])=[O:4].C(N(CC)CC)C.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>ClCCl>[CH3:17][S:18]([O:1][CH2:2][C:3]([O:5][CH2:6][CH2:7][CH2:8][CH3:9])=[O:4])(=[O:20])=[O:19] | CS(=O)(=O)Cl | CCCCOC(=O)CO | 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 | 0 | 8 | 27.8 g (0.2 mol) of n-butyl hydroxyacetate (95% pure by GC) and 20.2 g (0.2 mol) of triethylamine are first introduced into 300 ml of dichloromethane at -5° C. 34.4 g (0.3 mol) of methanesulfonyl chloride in 50 ml of dichloromethane are slowly added dropwise at 0° to 5° C. Stirring of the batch at 0° C. is continued ov... | CCCCOC(=O)COS(C)(=O)=O | null | null | null |
81,694 | ord_dataset-f196f0a87dd74fcd82ca019f8ff5cf9c | null | 1981-01-01T00:05:00 | true | [C:1]([CH:11]1[O:17][CH:16]2[C:13]([C:27](=[O:35])[CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)([C:14](=[O:26])[N:15]2[C:18](=[C:23]([CH3:25])[CH3:24])[C:19]([O:21][CH3:22])=[O:20])[NH:12]1)([O:3]CC1C=CC=CC=1)=[O:2]>O1CCCC1.[C].[Pd]>[C:1]([CH:11]1[O:17][CH:16]2[C:13]([C:27](=[O:35])[CH2:28][C:29]3[CH:30]=[CH:... | COC(=O)C(=C(C)C)N1C(=O)C2(C(=O)Cc3ccccc3)NC(C(=O)OCc3ccccc3)OC12 | null | null | [Pd] | 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 | A solution of 4.24 g of methyl α-(3ξ-carbobenzoxy-2-phenylacetyl-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]heptan-6-yl)-α-isopropylideneacetate dissolved in 64 ml of tetrahydrofuran is catalytically hydrogenated on 1.3 g of 5% palladium carbon under atmospheric pressure. The catalyst is removed by filtration and the filtrate ... | COC(=O)C(=C(C)C)N1C(=O)C2(C(=O)Cc3ccccc3)NC(C(=O)O)OC12 | null | 98.2 | null |
1,708,305 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[C@@H:13]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[N:12]([C@@H:21]([CH2:26][CH3:27])[CH:22]=[CH:23][C:24]#[N:25])[C:11](=[O:28])[C@@H:10]([CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[H][H]>CCO.[Pd]>[Cl:1][C:2]1[CH:3]=[C:... | CC[C@@H](C=CC#N)N1C(=O)[C@@H](CC(=O)OC(C)(C)C)C[C@H](c2cccc(Cl)c2)[C@H]1c1ccc(Cl)cc1 | [H][H] | null | [Pd] | 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 | 25 | 2 | To a solution of 56 mg (0.106 mmol) of tert-butyl 2-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-cyanopent-1-en-3-yl)-2-oxopiperidin-3-yl)acetate (Example 30, Step A) in 3.5 mL of EtOH) was added 10% palladium on activated carbon (11.30 mg, 10.62 μmol). Then the reaction mixture was subjected to regular h... | CC[C@@H](CCC#N)N1C(=O)[C@@H](CC(=O)OC(C)(C)C)C[C@H](c2cccc(Cl)c2)[C@H]1c1ccc(Cl)cc1 | null | null | null |
896,959 | ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded | null | 2009-01-01T00:08:00 | true | CS([N:5]1[C:9]([CH3:10])=[CH:8][C:7]([NH:11][C:12]2[N:13]=[C:14]([CH2:24]OS(C)(=O)=O)[C:15]3[C:20]([CH:21]=2)=[CH:19][C:18]([O:22][CH3:23])=[CH:17][CH:16]=3)=[N:6]1)(=O)=O.[NH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1.C([O-])([O-])=O.[K+].[K+]>C1COCC1.CCO>[CH3:23][O:22][C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][CH:17]=1... | COc1ccc2c(COS(C)(=O)=O)nc(Nc3cc(C)n(S(C)(=O)=O)n3)cc2c1 | C1CCNCC1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCO | null | null | null | null | null | null | null | null | null | 120 | null | A 2.0˜5.0 mL process vial was charged with 50 mg methanesulfonic acid 3-(1-methanesulfonyl-5-methyl-1H-pyrazol-3-ylamino)-6-methoxy-isoquinolin-1-ylmethyl ester, 50 mg piperidine, 75 mg K2CO3 in 3 mL THF/EtOH(1:1). The vial was heated at 120° C. for 30 min under microwave irradiation. After cooling, the reaction mixtur... | COc1ccc2c(CN3CCCCC3)nc(Nc3cc(C)[nH]n3)cc2c1 | null | 12.5 | null |
237,702 | ord_dataset-56e7a343b17a4d6da818127ceb19589d | null | 1991-01-01T00:11:00 | true | [NH2:1][C:2]1[S:3][C:4]2[CH2:5][CH2:6][NH:7][CH2:8][CH2:9][C:10]=2[N:11]=1.C(=O)([O-])[O-].[K+].[K+].[Br:18][C:19]1[CH:28]=[CH:27][CH:26]=[CH:25][C:20]=1[CH:21]=[CH:22][CH2:23]Br.C(OC(C)C)(C)C>CN(C)C=O>[NH2:1][C:2]1[S:3][C:4]2[CH2:5][CH2:6][N:7]([CH2:23][CH:22]=[CH:21][C:20]3[CH:25]=[CH:26][CH:27]=[CH:28][C:19]=3[Br:18... | Nc1nc2c(s1)CCNCC2 | BrCC=Cc1ccccc1Br | 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 | CC(C)OC(C)C | null | null | null | null | null | null | null | null | null | null | null | Prepared analogously to Example 1 from 2-amino-4,5,7,8-tetrahydro-6H-thiazolo[5,4-d]azepine, potassium carbonate and 2-bromo-cinnamyl bromide in anhydrous dimethylformamide for 2 hours at 20° C. Yield: 42% of theory, Melting point: 103°-106° C. (diisopropylether). | Nc1nc2c(s1)CCN(CC=Cc1ccccc1Br)CC2 | null | 42 | null |
1,236,356 | ord_dataset-e96f5a2842f14e5380461c234100f05a | null | 2012-01-01T00:12:00 | true | [Cl:1][C:2]1[CH:8]=[C:7]([OH:9])[C:6]([CH3:10])=[CH:5][C:3]=1[NH2:4].C(=O)([O-])[O-].[K+].[K+].[Cl:17][C:18]1([C:21]2[N:25]=[C:24](S(C3C=CC(C)=CC=3)(=O)=O)[S:23][N:22]=2)[CH2:20][CH2:19]1>C(#N)C>[Cl:1][C:2]1[CH:8]=[C:7]([O:9][C:24]2[S:23][N:22]=[C:21]([C:18]3([Cl:17])[CH2:20][CH2:19]3)[N:25]=2)[C:6]([CH3:10])=[CH:5][C:... | Cc1ccc(S(=O)(=O)c2nc(C3(Cl)CC3)ns2)cc1 | Cc1cc(N)c(Cl)cc1O | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | 25 | 0.5 | 3.00 g (19.04 mmol) of 2-chloro-4-hydroxy-5-methylaniline are introduced into 50 ml of acetonitrile, treated at ambient temperature with 3.16 g (22.84 mmol) of potassium carbonate and stirred at ambient temperature for 30 min. Subsequently, 6.26 g (19.04 mmol) of 3-(1-chlorocyclopropyl)-5-[(4-methylphenyl]sulphonyl]-1,... | Cc1cc(N)c(Cl)cc1Oc1nc(C2(Cl)CC2)ns1 | null | 52.8 | null |
1,561,136 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[CH2:17]([CH2:20][OH:21])[CH2:18][NH2:19]>>[CH3:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:6]2[N:7]=[C:2]([NH:19][CH2:18][CH2:17][CH2:20][OH:21])[CH:3]=[CH:4][CH:5]=2)=[CH:10][CH:11]=1 | NCCCO | COc1ccc(Nc2cccc(Cl)n2)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 | 95 mg of 6-chloro-N-(4-methoxyphenyl)pyridin-2-amine were mixed with 244 mg of n-propanolamine and the mixture obtained was treated in a vial analogously to the method as set out in Example 16b. 3-(6-(4-Methoxyphenylamino)pyridin-2-ylamino)propan-1-ol was obtained in the form of a brown oil. | COc1ccc(Nc2cccc(NCCCO)n2)cc1 | null | 64 | null |
956,804 | ord_dataset-ed65749688da45af8a8432967b017729 | null | 2010-01-01T00:05:00 | true | C([O:3][CH:4](OCC)[CH2:5][N:6]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:7](=[O:19])[CH2:8][CH2:9][O:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)C.Cl.ClCCl>O1CCOCC1>[O:3]=[CH:4][CH2:5][N:6]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:2... | CCOC(CN(CCCCCOCCc1ccccc1)C(=O)CCOCCc1ccccc1)OCC | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | ClCCl | null | null | null | null | null | null | null | null | null | null | null | N-(2,2-Diethoxyethyl)-3-phenethyloxy-N-(5-phenethyloxypentyl)propanamide (Example 9b), 0.18 g) was dissolved in anhydrous dioxane (5 mL) and treated with concentrated hydrochloric acid (5 mL) at room temperature. The resultant solution was stirred for 1 hour and then poured into dichloromethane (10 mL), washed with wat... | O=CCN(CCCCCOCCc1ccccc1)C(=O)CCOCCc1ccccc1 | null | null | null |
581,820 | ord_dataset-60f3171f0342452f8814e7f294e2be8b | null | 2003-01-01T00:02:00 | true | [Cl:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[S:11][C:10]3[N:12]=[CH:13][CH:14]=[N:15][C:9]=3[N:8](COC)[C:7]=2[CH:19]=1.Cl>O1CCCC1>[Cl:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[S:11][C:10]3[N:12]=[CH:13][CH:14]=[N:15][C:9]=3[NH:8][C:7]=2[CH:19]=1 | COCN1c2cc(CCl)ccc2Sc2nccnc21 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 0.5 | 6 g of 8-chloromethyl-10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazine was dissolved in 50 ml of tetrahydrofuran and 20 ml of 6 N hydrochloric acid was added thereto at 0° C. After stirring at room temperature for 30 minutes, the reaction mixture was poured into ice-water and extracted with ethyl acetate. The ext... | ClCc1ccc2c(c1)Nc1nccnc1S2 | null | 94.1 | null |
1,492,221 | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | null | 2014-01-01T00:10:00 | true | [Cl:1][C:2]1[CH:3]=[C:4](B2OC(C)(C)C(C)(C)O2)[CH:5]=[C:6]([Cl:14])[C:7]=1[O:8][CH2:9][C:10]([F:13])([F:12])[F:11].Br[C:25]([C:27]([F:30])([F:29])[F:28])=[CH2:26].C([O-])([O-])=O.[K+].[K+]>C1COCC1.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:14][C:6]1[CH:5]=[C:4]([C:... | CC1(C)OB(c2cc(Cl)c(OCC(F)(F)F)c(Cl)c2)OC1(C)C | C=C(Br)C(F)(F)F | null | Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1 | O=C([O-])[O-] | [K+] | 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 | 80 | null | A mixture of 2-(3,5-dichloro-4-(2,2,2-trifluoroethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (530 mg, 1.43 mmol), 2-bromo-3,3,3-trifluoroprop-1-ene (275 mg, 1.57 mmol), K2CO3 (395 mg, 2.86 mmol) and Pd(PPh3)2Cl2 (20 mg, 0.029 mmol) in THF (3 mL) and H2O (3 mL) was heated at 80° C. in a sealed tube for 3 h. The... | C=C(c1cc(Cl)c(OCC(F)(F)F)c(Cl)c1)C(F)(F)F | null | 74.2 | null |
1,162,712 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | [F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([CH2:13][OH:14])=[C:11]([CH3:15])[O:10][N:9]=2)=[N:6][CH:7]=1.[CH3:16][O:17][C:18]([C:20]1[S:24][N:23]=[C:22](O)[CH:21]=1)=[O:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:16][O:17][C:18]([C:20]1[S:24][N:23]=[C:22]([O:14][CH2:13][C:12]2[C:8]([C:... | COC(=O)c1cc(O)ns1 | Cc1onc(-c2ccc(F)cn2)c1CO | null | CCOC(=O)N=NC(=O)OCC | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 8 | To a solution of [3-(5-fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-methanol (458 mg, 2.2 mmol) in THF (10 mL) was added 3-hydroxy-isothiazole-5-carboxylic acid methyl ester (350 mg, 1.9 mmol) and triphenylphosphine (692 mg, 2.6 mmol) at 0° C. under an argon atmosphere. Then diethyl azodicarboxylate (˜40% in toluene, 1... | COC(=O)c1cc(OCc2c(-c3ccc(F)cn3)noc2C)ns1 | null | 73.5 | null |
1,607,603 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | [Br:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([Cl:15])[CH:10]=2)[C:5]([N+:16]([O-])=O)=[CH:4][CH:3]=1.[Cl-].[NH4+]>CO.C1COCC1.[Zn]>[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([Cl:15])[CH:10]=2)[C:5]([NH2:16])=[CH:4][CH:3]=1 | O=[N+]([O-])c1ccc(Br)nc1Nc1ccnc(Cl)c1 | null | null | [Cl-] | [NH4+] | [Zn] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CO | null | null | null | null | null | null | null | null | null | 25 | 0.08 | (6-Bromo-3-nitro-pyridin-2-yl)-(2-chloro-pyridin-4-yl)amine (step 1) (1 eq, 0.303 mmol, 100 mg) is dissolved in MeOH/THF (6 ml of a 1:1 mixture) and stirred for 5 minutes at RT. Zinc (22 eq, 6.6 mmol 350 mg) is added and the reaction mixture is stirred for a further 20 minutes. Saturated aqueous ammonium chloride (0.8 ... | Nc1ccc(Br)nc1Nc1ccnc(Cl)c1 | null | null | null |
1,444,930 | ord_dataset-275a3da8f45f4536ad29727f0ef9ba66 | null | 2014-01-01T00:06:00 | true | C[O:2][C:3](=[O:30])[C@H:4]([NH:6][C:7]([C:9]1[CH:29]=[CH:28][C:12]2[N:13]([CH3:27])[C:14]([NH:16][C:17]3[S:18][C:19]4[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:20]=4[N:21]=3)=[N:15][C:11]=2[CH:10]=1)=[O:8])[CH3:5].[OH-].[Li+]>>[Cl:26][C:24]1[CH:23]=[CH:22][C:20]2[N:21]=[C:17]([NH:16][C:14]3[N:13]([CH3:27])[C:12]4[CH:28]... | COC(=O)[C@@H](C)NC(=O)c1ccc2c(c1)nc(Nc1nc3ccc(Cl)cc3s1)n2C | null | null | [Li+] | [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 | (R)-2-{[2-(6-Chloro-benzothiazol-2-ylamino)-1-methyl-1H-benzoimidazole-5-carbonyl]-amino}-propionic acid (341 mg) was prepared by following General Procedure E starting from (R)-2-{[2-(6-chloro-benzothiazol-2-ylamino)-1-methyl-1H-benzoimidazole-5-carbonyl]-amino}-propionic acid methyl ester (475 mg) and lithium hydroxi... | C[C@@H](NC(=O)c1ccc2c(c1)nc(Nc1nc3ccc(Cl)cc3s1)n2C)C(=O)O | null | 74.1 | null |
1,766,480 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | O[C:2]1[C:3]2[N:11]=[CH:10][CH:9]=[C:8]([C:12]([NH2:14])=[O:13])[C:4]=2[N:5]=[CH:6][N:7]=1.Cl.[N:16]1([CH2:20][C@@H:21]([NH2:32])[C:22]2[CH:27]=[CH:26][C:25]([F:28])=[C:24]([CH:29]([F:31])[F:30])[CH:23]=2)[CH2:19][CH2:18][CH2:17]1>>[N:16]1([CH2:20][C@@H:21]([NH:32][C:2]2[C:3]3[N:11]=[CH:10][CH:9]=[C:8]([C:12]([NH2:14])... | NC(=O)c1ccnc2c(O)ncnc12 | N[C@H](CN1CCC1)c1ccc(F)c(C(F)F)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 | Compound 48 was prepared following general synthesis scheme 7 wherein 4-hydroxypyrido[3,2-d]pyrimidine-8-carboxamide (G) was reacted with (S)-2-Azetidin-1-yl-1-(3-difluoromethyl-4-fluoro-phenyl)-ethylamine hydrochloride to give the title compound as a white solid. LC/MS [409 (M+H)]; 1H NMR (400 MHz, DMSO-d6) δ 9.93 (s,... | NC(=O)c1ccnc2c(N[C@H](CN3CCC3)c3ccc(F)c(C(F)F)c3)ncnc12 | null | null | null |
1,735,888 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | [H-].[Na+].[C:3](#[N:7])[CH2:4][C:5]#[N:6].Br[C:9]([C:15]1[N:16]=[C:17]([CH3:20])[O:18][CH:19]=1)([CH3:14])[C:10]([O:12][CH3:13])=[O:11]>CN(C=O)C>[C:5]([CH:4]([C:3]#[N:7])[C:9]([CH3:14])([C:15]1[N:16]=[C:17]([CH3:20])[O:18][CH:19]=1)[C:10]([O:12][CH3:13])=[O:11])#[N:6] | COC(=O)C(C)(Br)c1coc(C)n1 | N#CCC#N | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | 0.25 | To NaH (60%, 0.293 g, 7.32 mmol) in 10 mL of DMF at room temperature was added dropwise malononitrile (0.483 g, 7.32 mmol) in 5 mL of DMF. After stirring at room temperature for 15 minutes, the intermediate from Step C (1.82 g, 7.32 mmol) in 10 mL of DMF was added. The resulting mixture was stirred for 2 hours and then... | COC(=O)C(C)(c1coc(C)n1)C(C#N)C#N | null | null | null |
854,468 | ord_dataset-faa0236be76c4501841c954527cd1b6c | null | 2008-01-01T00:12:00 | true | [OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([NH:27]C(=O)OC(C)(C)C)[C:10](=[O:26])[NH:11][C:12]2[CH:13]=[C:14]3[C:24](=[O:25])[NH:23][N:22]=[CH:21][C:16]4=[CH:17][NH:18][C:19]([CH:20]=2)=[C:15]34)=[CH:4][CH:3]=1.[ClH:35]>O1CCOCC1>[ClH:35].[NH2:27][C@H:9]([CH2:8][C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=1)[C:10]([... | CC(C)(C)OC(=O)N[C@H](Cc1ccc(O)cc1)C(=O)Nc1cc2c3c(c[nH]c3c1)C=NNC2=O | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | null | Preparation of example 178 from the title compound of Example 155 (90 mg, 0.194 mmol) and 4M HCl in dioxane (10 mL) was carried out analogously to Example 91. Isolation, also in an analogous manner afforded the title compound (56 mg, 0.140 mmol) as an orange/yellow powder in 72% yield. | N[C@H](Cc1ccc(O)cc1)C(=O)Nc1cc2c3c(c[nH]c3c1)C=NNC2=O | null | 72 | null |
620,234 | ord_dataset-2952e63264f5422a84e12cca1e0541ee | null | 2003-01-01T00:12:00 | true | [OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([OH:12])[CH:3]=1.Cl.[CH3:14]O>>[CH3:14][O:12][C:4]1[CH:3]=[C:2]([OH:1])[C:11]2[C:6]([CH:5]=1)=[CH:7][CH:8]=[CH:9][CH:10]=2 | Oc1cc(O)c2ccccc2c1 | CO | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 25 | 24 | To a stirring solution of 1,3-dihydroxynaphthalene (2.31 g, 14.4 mmol) in methanol (150 mL) at 0° C., hydrochloride gas was bubbed for 10 min. The resulting solution was continued stirring at room temperature for 24 hrs. A residue was obtained after evaporation of methanol and purified by silica gel column chromatograp... | COc1cc(O)c2ccccc2c1 | null | 57 | null |
209,511 | ord_dataset-ac1c7aa04d6c4e588e723e3e05721681 | null | 1990-01-01T00:05:00 | true | [C:1]([N:4]1[CH2:9][CH:8]=[C:7]([C:10]2[C:15]([F:16])=[CH:14][C:13]([C:17](=[O:28])[C:18](=[CH:24]OCC)[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:12]([F:29])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[CH:30]1([NH2:33])[CH2:32][CH2:31]1>C(OCC)C>[C:1]([N:4]1[CH2:9][CH:8]=[C:7]([C:10]2[C:15]([F:16])=[CH:14][C:13]([C:17](=[O:... | NC1CC1 | CCOC=C(C(=O)OCC)C(=O)c1cc(F)c(C2=CCN(C(C)=O)CC2)cc1F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | null | 22 | A solution of 4.50 g (11.06 mmol) of ethyl 4-(1-acetyl-1,2,3,6-tetrahydro-4-pyridyl)-α-(ethoxymethylene)-2,5-difluoro-β-oxobenzenepropionate in 50 ml of ethyl ether was treated with 0.77 g (13.5 mmol) of cyclopropylamine and stirred for 22 hours. The title compound was isolated as a syrup after evaporation under vacuum... | CCOC(=O)C(=CNC1CC1)C(=O)c1cc(F)c(C2=CCN(C(C)=O)CC2)cc1F | null | null | null |
963,389 | ord_dataset-ed65749688da45af8a8432967b017729 | null | 2010-01-01T00:05:00 | true | [CH:1]1([C:7]2[N:12]=[N:11][C:10]([C:13]3[CH:54]=[CH:53][C:16]([CH2:17][C:18]4[N:19]([C:31]5[CH:32]=[C:33]([N:37]6[S:41](=[O:43])(=[O:42])[N:40](COCC[Si](C)(C)C)[C:39](=[O:52])[CH2:38]6)[CH:34]=[CH:35][CH:36]=5)[CH:20]=[C:21]([C:23]5[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=5[Cl:30])[N:22]=4)=[CH:15][CH:14]=3)=[CH:9... | C[Si](C)(C)CCOCN1C(=O)CN(c2cccc(-n3cc(-c4ccc(Cl)cc4Cl)nc3Cc3ccc(-c4ccc(C5CCCCC5)nn4)cc3)c2)S1(=O)=O | null | null | CCCC[N+](CCCC)(CCCC)CCCC | [F-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 5-{3-[2-[4-(6-Cyclohexyl-pyridazin-3-yl)-benzyl]-4-(2,4-dichloro-phenyl)-imidazol-1-yl]-phenyl}-1,1-dioxo-2-(2-trimethylsilanyl-ethoxymethyl)-[1,2,5]thiadiazolidin-3-one (16 mg, 0.02 mmol) was treated as described in general procedure W using tetrabutylammonium fluoride (26 mg, 0.1 mmol) to give 5-{3-[2-[4-(6-cyclohexy... | O=C1CN(c2cccc(-n3cc(-c4ccc(Cl)cc4Cl)nc3Cc3ccc(-c4ccc(C5CCCCC5)nn4)cc3)c2)S(=O)(=O)N1 | null | null | null |
924,401 | ord_dataset-cc0899cd744f4f7f8e7f2463560faad1 | null | 2009-01-01T00:12:00 | true | [Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:25])=[C:6]([CH:24]=1)[C:7]([NH:9][C:10]1[CH:15]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:13]=[C:12]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:11]=1)=[O:8].[N:26]1([C:32](Cl)=[O:33])[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][C:32]([N:26]2[CH2:31][C... | CC(C)(C)c1cc(NC(=O)c2cc(Br)ccc2O)cc(C(C)(C)C)c1 | O=C(Cl)N1CCOCC1 | null | null | null | null | null | null | null | 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-bromo-N-{3,5-bis[(1,1-dimethyl)ethyl]phenyl}-2-hydroxybenzamide and morpholine-4-carbonyl chloride as the raw materials, the same operation as the example 71 gave the title compound. | CC(C)(C)c1cc(NC(=O)c2cc(Br)ccc2OC(=O)N2CCOCC2)cc(C(C)(C)C)c1 | null | 93.6 | null |
1,077,376 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([CH2:20][SH:21])=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:23]1[CH:28]=[CH:27][C:26]([C:29]2[N:30]=[C:31]([NH:34][CH2:35][CH:36]3[CH2:38][CH2:37]3)[S:32][CH:33]=2)=[CH:25][CH:24]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=C... | CC(C)(C)OC(=O)N1CCc2ccc(Cl)c(CS)c2CC1 | Brc1ccc(-c2csc(NCC3CC3)n2)cc1 | null | [Pd] | CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21 | O=C(/C=C/c1ccccc1)/C=C/c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 100 | null | To a solution of 3-tert-butoxycarbonyl-7-chloro-6-mercaptomethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine (0.051 g, 0.155 mmol) in dry dioxane (0.7 mL) add N-[4-(4-bromo-phenyl)-thiazol-2-yl]-cyclopropylmethylamine (0.043 g, 0.14 mmol), tris(dibenzylideneacetone)dipalladium(0) (3.2 mg, 0.0035 mmol), Xantphos (4.1 mg, 0.01... | CC(C)(C)OC(=O)N1CCc2ccc(Cl)c(CSc3ccc(-c4csc(NCC5CC5)n4)cc3)c2CC1 | null | 97.6 | null |
702,879 | ord_dataset-c408dfed796e4354b61e312e67f7143f | null | 2006-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[CH:10][C:9]=2[CH2:13][CH2:14][C:15](OC)=[O:16])=[CH:4][C:3]=1[F:19].[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[CH:10][C:9]=2[CH2:13][CH2:14][CH2:15][OH:16])=[CH:4][C:3]=1[F:19] | COC(=O)CCc1cnoc1-c1ccc(Cl)c(F)c1 | null | null | CC(C)C[Al+]CC(C)C | Cl | [H-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 1 | To a solution of methyl 3-[5-(4-chloro-3-fluorophenyl)-4-isoxazolyl]propionate (3.30 g) in tetrahydrofuran (30 ml) was gently added diisobutylaluminum hydride (1.0 M hexane solution, 25 ml) at 0° C., and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into dilute hydrochloric acid,... | OCCCc1cnoc1-c1ccc(Cl)c(F)c1 | null | 93.8 | null |
200,547 | ord_dataset-31f00a039ca0424788e5e1970d25a8fd | null | 1989-01-01T00:12:00 | true | [CH:1]1([S:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH:14][S:15]([CH2:18][CH3:19])(=[O:17])=[O:16])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N+:20]([O-])([OH:22])=[O:21].C(=O)([O-])O.[Na+]>C(O)(=O)C>[CH:1]1([S:7][C:8]2[CH:13]=[C:12]([N+:20]([O-:22])=[O:21])[CH:11]=[CH:10][C:9]=2[NH:14][S:15]([CH2:18][CH3:19])(=[O:17])... | CCS(=O)(=O)Nc1ccccc1SC1CCCCC1 | O=[N+]([O-])O | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | 0 | null | In 20 ml of acetic acid was dissolved 1.5 g of N-[2-(cyclohexylthio)phenyl]ethanesulfonamide, 0.33 g of 61% nitric acid was added dropwise on heating at 80°-85° C., and then the mixture was stirred on heating for 1 hour. The reaction solution was poured into ice water, neutralized with a saturated sodium hydrogen carbo... | CCS(=O)(=O)Nc1ccc([N+](=O)[O-])cc1SC1CCCCC1 | null | 63.8 | null |
595,299 | ord_dataset-278fb6af8a994ac69e4d95e6e6eff756 | null | 2003-01-01T00:05:00 | true | CO[CH2:3][C:4](=[C:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][CH2:9][C:8]2[CH:17]=[CH:18][CH:19]=[CH:20][C:7]1=2)[CH3:5].[BrH:21]>C(O)(=O)C.O>[CH3:5][C:4](=[C:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][CH2:9][C:8]2[CH:17]=[CH:18][CH:19]=[CH:20][C:7]1=2)[CH2:3][Br:21] | COCC(C)=C1c2ccccc2CCc2ccccc21 | Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | The above ether (3.6 g, 13.6 mmol) was dissolved in acetic acid (40 ml) and 48% hydrobromic acid (20 ml) was added. After 7 days the mixture was diluted with water (200 ml) and extracted with benzene (100 ml). The organic phase was dried (MgSO4), filtered and the solvent was evaporated in vacuo to give 3.8 g of crude 5... | CC(CBr)=C1c2ccccc2CCc2ccccc21 | null | null | null |
814,765 | ord_dataset-50f99930fc41474db226bc80774b38df | null | 2008-01-01T00:04:00 | true | [OH:1][C:2]1([C:15]([OH:17])=[O:16])[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[CH2:18](O)[CH2:19][CH2:20][CH3:21].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>O.C1(C)C=CC=CC=1>[OH:1][C:2]1([C:15]([O:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:16])[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:8]=2[C:9]2[... | CCCCO | O=C(O)C1(O)c2ccccc2-c2ccccc21 | null | O=C([O-])O | O=S(=O)(O)O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | To a reactor were added 0.05 mol of 9-hydroxyfluorene-9-carboxlic acid, 0.075 mol of butanol, 40 ml of toluene and 0.4 ml of concentrated sulfuric acid. The reaction was heated to reflux for 6 hrs, while water was separated by a water segregator. At the end of the reaction, the reaction mixture was neutralized with sod... | CCCCOC(=O)C1(O)c2ccccc2-c2ccccc21 | null | 80 | null |
1,626,539 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12](=[O:14])[CH3:13])=[C:5]2Cl.[CH3:16][N:17]([CH3:25])[CH2:18][CH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12](=[O:14])[CH3:13])=[C:5]2[N:22]1[CH2:23][CH2:24][CH:19]([CH2:18]... | CN(C)CC1CCNCC1 | CC(=O)c1cnc2ccc(Br)cc2c1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Following general procedure B, 1-(6-bromo-4-chloroquinolin-3-yl)ethanone (160 mg, 0.560 mmol) was reacted with N,N-dimethyl-1-(piperidin-4-yl)methanamine (172 mg, 0.800 mmol) to afford the desired product (17.7 mg, 8%) as an off-white solid: ESI MS m/z 390 [C19H24BrN3O+H]+. | CC(=O)c1cnc2ccc(Br)cc2c1N1CCC(CN(C)C)CC1 | null | 8.1 | null |
790,856 | ord_dataset-530502f8e61e455784f93c5faa45c94b | null | 2007-01-01T00:09:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([N:13]2[CH2:19][C:18]3[CH:20]=[CH:21][C:22]([Cl:24])=[CH:23][C:17]=3[NH:16][C:15](=[O:25])[CH2:14]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:28](I)[CH3:29]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([N:13]2[CH2:19][C:18]3[CH:20]=[CH:21][C:2... | CCI | CC(C)(C)OC(=O)N1CC[C@@H](N2CC(=O)Nc3cc(Cl)ccc3C2)C1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 0 | 0.25 | (R)-3-(8-Chloro-2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl)pyrrolidine-1-carboxylic acid tert-butyl ester (0.258 g, 0.70 mmol) was dissolved in THF (7 mL) and cooled to 0° C. To the solution was added NaH (0.042 g, 1.0 mmol) and stirred for 15 min, followed by ethyl iodide (0.085 mL, 1.0 mmol). The solution wa... | CCN1C(=O)CN([C@@H]2CCN(C(=O)OC(C)(C)C)C2)Cc2ccc(Cl)cc21 | null | 47.1 | null |
1,431,187 | ord_dataset-5e6956e6e8c24a168866a253f4a66c6c | null | 2014-01-01T00:05:00 | true | [CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]3[N:10]([N:12]=[C:13]([C:16]4[CH:33]=[CH:32][C:19]([O:20][CH2:21][C@@H:22]([NH:24][C:25](=O)[O:26]C(C)(C)C)[CH3:23])=[CH:18][C:17]=4[F:34])[C:14]=3[F:15])[CH:11]=2)[CH2:3][CH2:2]1.Cl.[C:36](OCC)(=O)C>C(OCC)(=O)C>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]3[N:10]([N:12]=[C:13... | CCOC(C)=O | C[C@@H](COc1ccc(-c2nn3cc(OCC4CC4)ccc3c2F)c(F)c1)NC(=O)OC(C)(C)C | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 25 | 6 | A mixture of tert-butyl [(1S)-2-{4-[6-(cyclopropylmethoxy)-3-fluoropyrazolo[1,5-a]pyridin-2-yl]-3-fluorophenoxy}-1-methylethyl]carbamate (67 mg), 4 M hydrogen chloride/ethyl acetate (2 mL), and ethyl acetate (1 mL) was stirred at room temperature for 6 hr. The mixture was concentrated under reduced pressure. The residu... | CC(=O)N[C@@H](C)COc1ccc(-c2nn3cc(OCC4CC4)ccc3c2F)c(F)c1 | null | null | null |
1,627,402 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | CC(C)([O-])C.[K+].[Br:7][C:8]1[CH:13]=[CH:12][NH:11][C:10](=[O:14])[CH:9]=1.C(=O)([O-])[O-].[K+].[K+].CC1C=CC(S(O[CH:32]2[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34][CH2:33]2)(=O)=O)=CC=1>COCCOC>[Br:7][C:8]1[CH:13]=[CH:12][N:11]([CH:32]2[CH2:37][CH2:36][N:35]([C:38]([O:40][C:4... | O=c1cc(Br)cc[nH]1 | Cc1ccc(S(=O)(=O)OC2CCN(C(=O)OC(C)(C)C)CC2)cc1 | null | CC(C)(C)[O-] | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COCCOC | null | null | null | null | null | null | null | null | null | null | 25 | 0.17 | Potassium tert-butoxide (7.09 g) was added at room temperature to a mixture of 4-bromopyridin-2(1H)-one (10 g) in DME (287 mL). The reaction mixture was stirred at room temperature for 10 minutes. Then, potassium carbonate (15.9 g) and tert-butyl 4-(((4-methylphenyl)sulfonyl)oxy)piperidine-1-carboxylate (37.8 g) were a... | CC(C)(C)OC(=O)N1CCC(n2ccc(Br)cc2=O)CC1 | null | 71.6 | null |
1,286,852 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | C([N:8](CC1C=CC=CC=1)[CH:9]1[CH2:13][CH:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:11]([CH2:19][CH3:20])[CH2:10]1)C1C=CC=CC=1.[H][H]>CCO.[OH-].[OH-].[Pd+2]>[NH2:8][CH:9]1[CH2:13][CH:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:11]([CH2:19][CH3:20])[CH2:10]1 | CCOC(=O)C1CC(N(Cc2ccccc2)Cc2ccccc2)CC1CC | [H][H] | null | [Pd+2] | [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 | To a vessel containing a slurry of 20 wt % Pd(OH)2 on C (12.9 g, 18.4 mmol) in EtOH (1.0 L) was added ethyl 4-(dibenzylamino)-2-ethylcyclopentanecarboxylate (129 g, 352 mmol). The reaction was shaken for about 90 min at about 50° C. under about 30 psi of hydrogen. After removal of the hydrogen source, a nitrogen atmosp... | CCOC(=O)C1CC(N)CC1CC | null | 98.9 | null |
1,532,380 | ord_dataset-8d5c200bca27407ab9febe7598e16458 | null | 2015-01-01T00:01:00 | true | [F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:8]=[C:7]2O.O=P(Cl)(Cl)[Cl:20]>>[Cl:20][C:7]1[C:6]2[C:11](=[C:2]([F:1])[CH:3]=[CH:4][CH:5]=2)[N:10]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:8]=1 | CCOC(=O)c1nc(O)c2cccc(F)c2n1 | O=P(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of ethyl 8-fluoro-4-hydroxyquinazoline-2-carboxylate (530 mg, 2.2 mmol) and POCl3 (3 mL) was heated under reflux for 5 h. The mixture was concentrated under reduced pressure, and then toluene was twice added and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting... | CCOC(=O)c1nc(Cl)c2cccc(F)c2n1 | null | 65 | null |
264,915 | ord_dataset-a7bd0db0684c464bb02ff6a36065fee3 | null | 1993-01-01T00:03:00 | true | Cl.[F:2][C:3]1[CH:16]=[CH:15][C:6]([C:7]([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:4]=1.[C:17]1([S:23](Cl)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>N1C=CC=CC=1>[F:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([CH:9]2[CH2:14][CH2:13][N:12]([S:23]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)(... | O=S(=O)(Cl)c1ccccc1 | O=C(c1ccc(F)cc1)C1CCNCC1 | null | Cl | 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 | 8 | A mixture of 4-(4-fluorobenzoyl)piperidine hydrochloride (53.30 g, 0.219 mol) and benzenesulfonyl chloride (44 g, 0.25 mol) in 500 mL of pyridine was stirred at room temperature overnight. The solvent was removed in vacuo, and the residue was partitioned between CH2Cl2 and dilute NaOH. The CH2Cl2 solution was extracted... | O=C(c1ccc(F)cc1)C1CCN(S(=O)(=O)c2ccccc2)CC1 | null | null | null |
988,780 | ord_dataset-35b56288528641309a040cc2b6710b61 | null | 2010-01-01T00:08:00 | true | [S:1]1[C:5]([CH2:6][O:7][C:8]([NH:10][C@H:11]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:12][NH:13][CH2:14][C@H:15]([NH:23][C:24]([O:26][CH2:27][C:28]2[S:32][CH:31]=[N:30][CH:29]=2)=[O:25])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:9])=[CH:4][N:3]=[CH:2]1.[CH:40](=O)[C:41]1[CH:46]=[CH:4... | O=C(N[C@@H](CNC[C@@H](Cc1ccccc1)NC(=O)OCc1cncs1)Cc1ccccc1)OCc1cncs1 | O=Cc1ccccc1 | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | The product from Example 31D (80 mg, 0.141 mmol), benzaldehyde (17 μl, 0.170 mmol), acetic acid (10 μl, 0.166 mmol), and sodium triacetoxyborohydride (48 mg, 0.226 mmol) were processed as described in Example 27 to provide the title compound (17 mg, 18%). 1H NMR (CDCl3) δ 8.73 (s, 2H), 7.78 (s, 2H), 7.32-7.08 (m, 15H),... | O=C(N[C@H](Cc1ccccc1)CN(Cc1ccccc1)C[C@@H](Cc1ccccc1)NC(=O)OCc1cncs1)OCc1cncs1 | null | 18.4 | null |
906,470 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | [Na].[Cl-].[NH2:3][C:4]([NH2:6])=[NH2+:5].[F:7][C:8]([F:30])([F:29])[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[CH:14]([CH2:18][C:19](OCC)=[O:20])[N:13]([CH2:24][CH:25]([CH3:27])[CH3:26])[C:12]2=[O:28]>C(O)C.C(OCC)C>[F:30][C:8]([F:7])([F:29])[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[CH:14]([CH2:18][C:19]([NH:5]... | NC(N)=[NH2+] | CCOC(=O)CC1c2ccc(C(F)(F)F)cc2C(=O)N1CC(C)C | null | [Cl-] | [Na] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | CCO | null | null | null | null | null | null | null | null | null | 20 | 16 | N-[2-(2-Isobutyl-3-oxo-5-trifluoromethyl-2,3-dihydro-1H-isoindol-1-yl)-acetyl]-guanidine is prepared as described in Example 9, starting with 10 cm3 of absolute ethanol, 0.19 g of sodium, 0.78 g of guanidinium chloride and 1.86 g of ethyl (5-trifluoromethyl-2-isobutyl-3-oxo-2,3-dihyrdo-1H-isoindol-1-yl)acetate in 10 cm... | CC(C)CN1C(=O)c2cc(C(F)(F)F)ccc2C1CC(=O)NC(=N)N | null | 17.6 | null |
1,445,446 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | N1CCCCC1.[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][C:8]1=[O:16].[N:17]1[CH:22]=[CH:21][C:20](/[CH:23]=[CH:24]/[C:25]2[C:33]3[C:28](=[CH:29][CH:30]=[C:31]([CH:34]=O)[CH:32]=3)[N:27]([CH2:36][O:37][CH2:38][CH2:39][Si:40]([CH3:43])([CH3:42])[CH3:41])[N:26]=2)=[CH:19][CH:18]=1>CCO>[N:17]1[CH:22]=[CH:21]... | O=C1Cc2ccccc2N1 | C[Si](C)(C)CCOCn1nc(/C=C/c2ccncc2)c2cc(C=O)ccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | C1CCNCC1 | null | null | null | null | null | null | null | null | null | 75 | null | A solution of piperidine (0.2M in EtOH, 0.10 mL, 0.02 mmol) was added to a suspension of oxindole (16.5 mg, 0.12 mmol) and (E)-3-(2-(pyridin-4-yl)vinyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole-5-carbaldehyde (42.5 mg, 0.11 mmol) in EtOH (4 mL). The reaction was then heated to 75° C. for 15 hrs. The solvent was... | C[Si](C)(C)CCOCn1nc(/C=C/c2ccncc2)c2cc(C=C3C(=O)Nc4ccccc43)ccc21 | null | null | null |
866,407 | ord_dataset-b8b98725045d45bdbd73512048f4b47e | null | 2009-01-01T00:02:00 | true | [H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[CH:13]=[C:12]2[NH:14][C:15](=[O:47])[C:16]3([CH:21]([C:22]4[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:23]=4[O:29][C:30]4([C:34](OC)=[O:35])[CH2:33][CH2:32][CH2:31]4)[CH2:20][C:19](=[O:38])[NH:18][CH:17]3[C:39]3[CH:44]=[C:43]([F:45])[CH:42]=[CH:41][C:40]=3[CH3:46])[C:11]2=[CH:... | COC(=O)C1(Oc2ccc(Cl)cc2C2CC(=O)NC(c3cc(F)ccc3C)C23C(=O)Nc2cc(Cl)ccc23)CCC1 | null | null | [Al+3] | [H-] | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 1.5 | To a mixture of LiAlH4 (15 mg, 0.4 mmol) in THF (2 mL) was added racemic (2′S,3S,4′R)-6-chloro-4′-[5-chloro-2-(1-methoxycarbonyl-cyclobutoxy)-phenyl]-2′-(5-fluoro-2-methyl-phenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (RO5247453-000) (60 mg, 0.1 mmol). The mixture was stirred in a ice bath for 1.5 h, quenched ... | Cc1ccc(F)cc1C1NC(=O)CC(c2cc(Cl)ccc2OC2(CO)CCC2)C12C(=O)Nc1cc(Cl)ccc12 | null | 24.6 | null |
1,018,115 | ord_dataset-f024e9664ab64906a71a2ff6004cb3d0 | null | 2010-01-01T00:12:00 | true | [NH2:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]([N:16]3[CH2:21][CH2:20][CH:19]([CH2:22][N:23]([CH3:25])[CH3:24])[CH2:18][CH2:17]3)=[O:15])[CH:8]=2)=[C:4]([F:28])[CH:3]=1.[F:29][C:30]1[CH:35]=[CH:34][C:33]([NH:36][C:37]([C:39]2([C:43](O)=[O:44])[CH2:42][CH2:41][CH2:40]2)=[O:38])=[C... | CN(C)CC1CCN(C(=O)Nc2cc(Oc3ccc(N)cc3F)ccn2)CC1 | O=C(O)C1(C(=O)Nc2ccc(F)cc2)CCC1 | null | CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | 8 | 4-(Dimethylaminomethyl)piperidine-1-carboxylic acid [4-(4-amino-2-fluorophenoxy)pyridin-2-yl]amide (114 mg) was dissolved in N,N-dimethylformamide (4.0 ml). 1-(4-Fluorophenylcarbamoyl)cyclobutanecarboxylic acid (279 mg), triethylamine (0.164 ml) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate... | CN(C)CC1CCN(C(=O)Nc2cc(Oc3ccc(NC(=O)C4(C(=O)Nc5ccc(F)cc5)CCC4)cc3F)ccn2)CC1 | null | 10.7 | null |
708,690 | ord_dataset-c8069773c1a148aca8ab417108daacc5 | null | 2006-01-01T00:05:00 | true | I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[OH:10].[CH:11]#[C:12][CH2:13][CH3:14]>>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]2[CH:11]=[C:12]([CH2:13][CH3:14])[O:10][C:3]=2[CH:4]=1 | C#CCC | COc1ccc(I)c(O)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | This material was prepared from 2-iodo-5-methoxyphenol (1 g, 4 mmole) and 1-butyne in a manner as previously described for example 12a to give 570 mg (81%) of a brown oil. 1H NMR (CDCl3) δ 7.33 (1H, d, J=8.6 Hz), 6.97 (1H, d, J=2.2 Hz), 6.80 (1H, dd, J=2.2, 8.6 Hz), 6.26 (1H, s), 3.83 (3H, s), 3.04 (2H, q, J=7.3 Hz), 1... | CCc1cc2ccc(OC)cc2o1 | null | 81 | null |
596,866 | ord_dataset-843ef38b45484f72826f5f39d8a29c4d | null | 2003-01-01T00:06:00 | true | [N+](C1C=CC(COC([NH:12][CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]3[CH2:26][CH:25]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:24]4[CH:33]=[CH:34][CH:35]=[CH:36][C:23]=4[CH2:22][C:21]=3[CH:37]=2)=O)=CC=1)([O-])=O>[Pd].C(O)C>[NH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:18]=[CH:19][C:20]2[CH2:26][... | CCOC(=O)CC1Cc2ccc(OCCCNC(=O)OCc3ccc([N+](=O)[O-])cc3)cc2Cc2ccccc21 | null | null | [Pd] | 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 | 3 | A mixture of ethyl (±)-10,11-dihydro-3-[3-(4-nitrobenzyloxycarbonylamino)-1-propyloxy]-5H-dibenzo[a,d]cycloheptene-10-acetate (1.6 g 3 mmol), 10% palladium on charcoal (0.8 g, 1 mmol), and ethanol (50 mL) was shaken under H2 (48 psi) for 3 hr, then the catalyst was removed by filtration through celite®D. The filtrate w... | CCOC(=O)CC1Cc2ccc(OCCCN)cc2Cc2ccccc21 | null | 113.2 | null |
1,075,138 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N:12]=[C:13]=[O:14].[NH2:15][C:16]1[CH:17]=[C:18]([CH:30]=[CH:31][CH:32]=1)[CH2:19][CH2:20][NH:21][C:22]1[C:23]([C:27]([NH2:29])=[O:28])=[N:24][NH:25][CH:26]=1>C1COCC1.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3... | O=C=Nc1cc(C(F)(F)F)ccc1F | NC(=O)c1n[nH]cc1NCCc1cccc(N)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 20 | 12 | A solution of 0.14 ml of 1-fluoro-2-isocyanato-4-trifluoromethylbenzene is added at 20° C. to a solution of 0.25 g of 4-[(3-aminobenzyl)methylamino]-1H-pyrazole-3-carboxamide in 25 ml of anhydrous THF. The reaction medium is stirred for 12 hours at 20° C. and then diluted with 100 ml of ethyl acetate. The organic phase... | NC(=O)c1n[nH]cc1NCCc1cccc(NC(=O)Nc2cc(C(F)(F)F)ccc2F)c1 | null | null | null |
922,128 | 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.[F:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH2:19]Br>CN(C)C=O>[F:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH2:19][N:3]1[C:4](=[O:15])[C:5]2[C@@H:6]3[C:11]([CH3:12])([CH3:13])[C@@:9]([CH3... | Fc1ccccc1CBr | 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 | 120 | 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 2-fluoro-benzyl bromide (58 μL, 0.48 mmol) in N,N-dimethylformamide (5 mL) was heated at 100° C. overnight and then allowed to stand at room temperature for five days. The reaction mixture w... | Cn1c2c(c(=O)n1Cc1ccccc1F)[C@H]1CC[C@]2(C)C1(C)C | null | 41.7 | null |
700,899 | ord_dataset-bbd7e53f000345838ad4920a07a169ff | null | 2006-01-01T00:03:00 | true | [F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[C:5]([N:9]2[C:13]([CH3:14])=[C:12]([C:15]([OH:17])=O)[CH:11]=[N:10]2)[CH:6]=[CH:7][CH:8]=1.[NH2:20][C:21]1[CH:22]=[CH:23][C:24]([N:29]2[CH2:34][CH2:33][CH:32]([N:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)[CH2:31][CH2:30]2)=[C:25]([CH:28]=1)[C:26]#[N:27]>>[C:26]([C:25]1[CH:28]=[... | Cc1c(C(=O)O)cnn1-c1cccc(C(F)(F)F)c1 | N#Cc1cc(N)ccc1N1CCC(N2CCOCC2)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | By the reaction and treatment in the same manner as in Example 64 using 1-(3-trifluoromethylphenyl)-5-methylpyrazole-4-carboxylic acid (2.0 g) and 5-amino-2-(4-morpholinopiperidin-1-yl)benzonitrile (2.4 g), the title compound (1.0 g) was obtained, melting point: 215–216° C. | Cc1c(C(=O)Nc2ccc(N3CCC(N4CCOCC4)CC3)c(C#N)c2)cnn1-c1cccc(C(F)(F)F)c1 | null | 25.1 | null |
934,280 | ord_dataset-d8a5dc784dde4465894ec7c69d2e3ba6 | null | 2010-01-01T00:01:00 | true | C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([NH:23][C:24]3[N:25]([C:33]4[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=4)[N:26]=[C:27]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH:28]=3)=[O:22])=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.O1CCOCC1>C1COCC1>[C:29]([C:27]1[CH:28]=[C:24]([NH:2... | Cc1ccc(-n2nc(C(C)(C)C)cc2NC(=O)Nc2ccc(N3CCN(C(=O)OC(C)(C)C)CC3)nc2)cc1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | C1COCCO1 | null | null | null | null | null | null | null | null | null | 60 | null | Place 4-{5-[3-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-ureido]-pyridin-2-yl}-piperazine-1-carboxylic acid tert-butyl ester (565 mg, 1.06 mmol) in THF (10 mL). Add 4 M HCl in dioxane (2.65 mL, 10.6 mmol) and heat to 60° C. for 3 hours. Cool the reaction to room temperature and load onto a Varian™ SCX column. Wash the co... | Cc1ccc(-n2nc(C(C)(C)C)cc2NC(=O)Nc2ccc(N3CCNCC3)nc2)cc1 | null | null | null |
1,207,096 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | Cl.[Br:2][C:3]1[CH:4]=[C:5]([S:9](Cl)(=[O:11])=[O:10])[CH:6]=[N:7][CH:8]=1.C(N(CC)CC)C.[OH:20][CH2:21][CH2:22][NH2:23]>C(Cl)Cl>[Br:2][C:3]1[CH:4]=[C:5]([S:9]([NH:23][CH2:22][CH2:21][OH:20])(=[O:11])=[O:10])[CH:6]=[N:7][CH:8]=1 | O=S(=O)(Cl)c1cncc(Br)c1 | NCCO | null | 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 | null | null | A cooled (0° C.) solution of 5-bromopyridine-3-sulfonyl chloride hydrochloride (3.00 g, 10.2 mmol) in DCM (50 ml) was slowly treated with triethylamine (4.3 ml) and stirred until a clear solution was obtained. This solution was treated dropwise with 2-hydroxyethylamine (0.68 g, 0.68 mL) and stirred at RT for 16 hours. ... | O=S(=O)(NCCO)c1cncc(Br)c1 | null | null | null |
1,034,252 | ord_dataset-83acb82dc5ba4f7aba439b9875aaac43 | null | 2011-01-01T00:02:00 | true | [CH3:1][O:2][C:3]([C:5]1[C:13]2[N:12]=[C:11]([NH2:14])[NH:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4].COC(=O)C1C=C([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)C=C([N+]([O-])=O)C=1N>>[CH3:1][O:2][C:3]([C:5]1[C:13]2[N:12]=[C:11]([NH2:14])[NH:10][C:9]=2[CH:8]=[C:7]([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)[CH:6]=1)=[O:4... | COC(=O)c1cccc2[nH]c(N)nc12 | COC(=O)c1cc(-c2ccncc2)cc([N+](=O)[O-])c1N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 0.25 g (50% overall yield) of 2-amino-6-pyridin-4-yl-1H-benzoimidazole-4-carboxylic acid methyl ester was synthesized according to procedures described for the synthesis of 2-Amino-1H-benzoimidazole-4-carboxylic acid methyl ester (intermediate A) starting from 0.5 g (1.8 mmol) of above synthesized 2-Amino-3-nitro-5-pyr... | COC(=O)c1cc(-c2ccncc2)cc2[nH]c(N)nc12 | null | 50 | null |
1,331,645 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[F:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[N:23]=[CH:24][N:25]([CH:35]3[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]3)[C:26]=2[C:27]2[CH:32]=[CH:31][N:30]=[C:29]([NH:33][CH3:34])[N:28]=2)=[CH:18][CH:17]=1.[O:41]1[CH:45]=[CH:44][C:43]([CH:46]=O)=[N:42]1.C(OCC)C>C1COCC1>[F:15][C:16]1[CH:17]... | O=Cc1ccon1 | CNc1nccc(-c2c(-c3ccc(F)cc3)ncn2C2CCNCC2)n1 | 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 | CCOCC | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 1.5 | Sodium triacetoxyborohydride (135 mg, 0.637 mmol) was added to a solution of 4-[4-(4-fluorophenyl)-1-piperidin-4-yl-1H-imidazol-5-yl]-N-methylpyrimidin-2-amine (C8) (150 mg, 0.426 mmol) and isoxazole-3-carbaldehyde (49.6 mg, 0.511 mmol) in THF (10 mL). After 90 minutes at room temperature, the reaction was concentrated... | CNc1nccc(-c2c(-c3ccc(F)cc3)ncn2C2CCN(Cc3ccon3)CC2)n1 | null | null | null |
855,028 | ord_dataset-faa0236be76c4501841c954527cd1b6c | null | 2008-01-01T00:12:00 | true | [NH2:1][C:2]1[C:11]2[C:6](=[C:7](Br)[CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:13]([NH:15][CH2:16][CH3:17])=[O:14].[CH3:18][O:19][C:20]1[CH:25]=[CH:24][N:23]=[CH:22][C:21]=1B(O)O>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:21]3[CH:22]=[N:23][CH:24]=[CH:25][C:20]=3[O:19][CH3:18])[CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:13]... | COc1ccncc1B(O)O | CCNC(=O)c1nnc2c(Br)cccc2c1N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from 4-amino-8-bromo-N-ethyl-cinnoline-3-carboxamide (70.0 mg, 0.237 mmol) and 4-methoxy-3-pyridine boronic acid (153.0 mg, 0.3439 mmol) according to Method A except that the extraction was carried out with methylene chloride rather than ethyl acetate and the flash column was eluted with... | CCNC(=O)c1nnc2c(-c3cnccc3OC)cccc2c1N | null | 25.6 | null |
731,110 | ord_dataset-eb4226b4f7644a01a737e7547b70014a | null | 2006-01-01T00:09:00 | true | [O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[N:17].[N:18]([Si](C)(C)C)=[N+:19]=[N-:20].C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[N:17]1[NH:18][N:19]=[N:20][C:16]=1[CH2:15][CH2:14][CH2:13][CH2:12][N:3]1[C:4](=[O:11])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[... | N#CCCCCN1C(=O)c2ccccc2C1=O | C[Si](C)(C)N=[N+]=[N-] | null | CCCC[Sn](=O)CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | 100 | null | To a solution of 5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pentanenitrile (6.84 g, 30 mmol) and azidotrimethylsilane (14 mL, 108 mmol) in toluene (40 mL) was added dibutyltin oxide (2.1 g, 6.0 mmol). The mixture was heated at 100° C. for 48 h, concentrated, and flash chromatographed on silica gel column, eluting with EtO... | O=C1c2ccccc2C(=O)N1CCCCc1nn[nH]n1 | null | 82.6 | null |
896,183 | ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded | null | 2009-01-01T00:08:00 | true | Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]2[O:15][CH2:14][CH2:13][NH:12][CH2:11]2)=[CH:6][CH:5]=1.Cl[C:17]1[N:22]([CH3:23])[C:21](=[O:24])[CH:20]=[C:19]([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][N:26]=2)[N:18]=1.C(N(CC)CC)C>O1CCCC1>[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]([C@@H:10]2[O:15][CH2:14][CH2:13][N:12]([C:17]3[N:... | COc1ccc([C@H]2CNCCO2)cc1 | Cn1c(Cl)nc(-c2ccncn2)cc1=O | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | A solution of (S)-2-(4-methoxyphenyl)morpholine hydrochloride (0.30 g, 1.35 mmol), 2-chloro-3-methyl-6-(4-pyrimidyl)-pyrimidin-4-one (0.40 g, 1.75 mmol) and triethylamine (0.56 ml, 4.05 mmol) in tetrahydrofuran(6 ml) was refluxed for several hours. The reaction mixture was removed in vacuo. The residue was dissolved in... | COc1ccc([C@H]2CN(c3nc(-c4ccncn4)cc(=O)n3C)CCO2)cc1 | null | 90.4 | null |
1,353,897 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | [Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[C:13]([F:15])[C:12]([N+:16]([O-])=O)=[CH:11][C:10]=1[Cl:19].[Cl-].[NH4+]>C(O)C.O.[Fe]>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:10]([Cl:19])=[CH:11][C:12]([NH2:16])=[C:13]([F:15])[CH:14]=1 | O=[N+]([O-])c1cc(Cl)c(Oc2ccncc2Br)cc1F | null | null | [Fe] | [Cl-] | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | 70 | null | To a solution of 3-bromo-4-(2-chloro-5-fluoro-4-nitrophenoxy)pyridine (2.00 g, 5.75 mmol) in ethanol/water (9:1, 50 mL) was added iron powder (2.00 g, 35.8 mmol) followed by ammonium chloride (2.00 g, 37.4 mmol). The mixture was heated at 70° C. for 2 h. The reaction mixture was filtered, and the solids were washed wit... | Nc1cc(Cl)c(Oc2ccncc2Br)cc1F | null | null | null |
644,043 | ord_dataset-c975a50a7600448fabd558f4a94a3e29 | null | 2004-01-01T00:08:00 | true | C(OC([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[CH3:26])[C:17]([C:27](=[O:45])[N:28]([CH2:30][C:31]3[CH:36]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:34]=[C:33]([C:41]([F:44])([F:43])[F:42])[CH:32]=3)[CH3:29])=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O... | Cc1ccccc1-c1cc(C2=CCN(C(=O)OC(C)(C)C)CC2)ncc1C(=O)N(C)Cc1cc(C(F)(F)F)cc(C(F)(F)F)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | 25 | null | A solution of 258 mg (0.407 mmol) 5-[(3,5-bis-trifluoromethyl-benzyl)-methyl-carbamoyl]-4-o-tolyl-3′,6′-dihydro-2′H-[2,4′]bipyridinyl-1′-carboxylic acid tert-butyl ester (Example 41) and 0.26 ml (3.2 mmol) trifluoroacetic acid in 2 ml dichloromethane was heated at reflux for 4 h. After cooling to room temperature the m... | Cc1ccccc1-c1cc(C2=CCNCC2)ncc1C(=O)N(C)Cc1cc(C(F)(F)F)cc(C(F)(F)F)c1 | null | 62.2 | null |
1,431,818 | ord_dataset-5e6956e6e8c24a168866a253f4a66c6c | null | 2014-01-01T00:05:00 | true | [Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[N:15]2[N:16]=[CH:17][C:18]([C:19](O)=[O:20])=[C:14]2[N:13]=[CH:12][C:11]=1[C:22]([N:24]1[CH2:29][CH2:28][CH:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:26][CH2:25]1)=[O:23].[CH2:36]([S:38]([NH2:41])(=[O:40])=[O:39])[CH3:37]>>[Cl:1][C:2]1[CH:7]... | O=C(O)c1cnn2c(Nc3ccc(F)cc3Cl)c(C(=O)N3CCC(c4ccccc4)CC3)cnc12 | CCS(N)(=O)=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In the same manner as in Example 1, step 6 and using 7-(2-chloro-4-fluorophenylamino)-6-(4-phenylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (115 mg, 0.23 mmol) obtained in step 2 and ethanesulfonamide (123 mg, 1.17 mmol), the title compound (53 mg, 39%) was obtained. | CCS(=O)(=O)NC(=O)c1cnn2c(Nc3ccc(F)cc3Cl)c(C(=O)N3CCC(c4ccccc4)CC3)cnc12 | null | 39.4 | null |
1,158,890 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | [NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]1=[S:10].[H-].[Na+].Cl[C:14]1[S:15][C:16]([CH:19]=[O:20])=[CH:17][N:18]=1>O1CCCC1>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10][C:14]1[S:15][C:16]([CH:19]=[O:20])=[CH:17][N:18]=1 | O=Cc1cnc(Cl)s1 | S=c1[nH]c2ccccc2[nH]1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | null | 1,3-Dihydro-benzimidazole-2-thione (1.0 g, 6.66 mmol) is suspended into 50 mL of tetrahydrofuran under argon. Then, 479 mg (9.99 mmol) of sodium hydride is added. The reaction mixture is stirred at room temperature until gas evolution has ceased. 2-Chloro-1,3-thiazole-5-carbaldehyde (983 mg, 6.66 mmol) is then added an... | O=Cc1cnc(Sc2nc3ccccc3[nH]2)s1 | null | 70.7 | null |
1,708,149 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [C:1]([O:7][CH2:8][C@H:9]([C:15]1[C:16](Br)=[C:17]2[C:22](=[CH:23][C:24]=1[CH3:25])[N:21]=[C:20]([CH3:26])[CH:19]=[CH:18]2)[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[Cl:28][C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1.C([O-])([O-])=O.[K+].[K+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=... | OB(O)c1ccc(Cl)cc1 | Cc1ccc2c(Br)c([C@@H](COC(=O)C(C)(C)C)OC(C)(C)C)c(C)cc2n1 | 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 | COCCOC | null | null | null | null | null | null | null | null | null | null | 110 | null | Pd(PPh3)4 (69 mg, 0.06 mmol) was added to a mixture (S)-2-(5-bromo-2,7-dimethylquinolin-6-yl)-2-tert-butoxyethyl pivalate (5E) (325 mg, 0.75 mmol), 4-chlorophenylboronic acid (175 mg, 1.1 mmol), K2CO3 (1.3 mL 2 M in water, 2.6 mmol) in 1,2-dimethoxyethane (10 mL). The reaction mixture was flushed with nitrogen, heated ... | Cc1ccc2c(-c3ccc(Cl)cc3)c([C@@H](COC(=O)C(C)(C)C)OC(C)(C)C)c(C)cc2n1 | null | 72.9 | null |
93,077 | ord_dataset-f0d0fe3f599c471ca1c011dbbcdeeff2 | null | 1982-01-01T00:04:00 | true | [N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]Cl)=[C:6]([C:12]([Cl:15])([Cl:14])[Cl:13])[CH:5]=1)([O-:3])=[O:2].[C:16]([OH:20])(=[O:19])[CH2:17][SH:18]>>[C:16]([CH2:17][S:18][S:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=1[C:12]([Cl:15])([Cl:14])[Cl:13])([OH:20])=[O:19] | O=C(O)CS | O=[N+]([O-])c1ccc(SCl)c(C(Cl)(Cl)Cl)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | As in Example 1, 61.4 g of 4-nitro-2-trichloromethylbenzenesulfenyl chloride is reacted with 18.4 g of thioglycolic acid. After the solvent has been distilled off and the residue recrystallized from toluene, there is obtained 62 g of carboxymethyldithio-4-nitro-2-trichloromethylbenzene; m.p.: 140° C. | O=C(O)CSSc1ccc([N+](=O)[O-])cc1C(Cl)(Cl)Cl | null | 85.6 | null |
1,763,332 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | [F:1][CH:2]([F:13])[O:3][C:4]1[C:5](I)=[CH:6][C:7]([O:10][CH3:11])=[N:8][CH:9]=1.[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([C:24]#[N:25])=[C:19](B(O)O)[CH:20]=1>>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([C:24]#[N:25])=[C:19]([C:5]2[C:4]([O:3][CH:2]([F:13])[F:1])=[CH:9][N:8]=[C:7]([O:10][CH3:11])[CH:6]=2)[CH:20]=1 | N#Cc1ccc(Cl)cc1B(O)O | COc1cc(I)c(OC(F)F)cn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 460 mg (purity 90%, 1.38 mmol) of 5-(difluoromethoxy)-4-iodo-2-methoxypyridine and 299 mg (1.65 mmol, 1.2 eq.) of 5-chloro-2-cyanophenylboronic acid in the presence of [1,1-bis(diphenylphosphino)ferrocene]palladium(II) chloride/dichloromethane monoadduct were reacted according to General Method 2A. The crude product wa... | COc1cc(-c2cc(Cl)ccc2C#N)c(OC(F)F)cn1 | null | null | null |
1,205,759 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | [N:1]1([C:5]([C:7]2[O:11][C:10]([S:12]([NH2:15])(=[O:14])=[O:13])=[CH:9][CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1.Cl[C:17]1[CH:22]=[C:21]([O:23][C@H:24]([CH3:46])[CH2:25][O:26][C:27]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=... | C[C@H](COC(c1ccccc1)(c1ccccc1)c1ccccc1)Oc1cc(Cl)nc(SCc2cccc(F)c2F)n1 | NS(=O)(=O)c1ccc(C(=O)N2CCC2)o1 | null | null | null | null | null | null | null | 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 subtitle compound was prepared from 5-(azetidin-1-ylcarbonyl)furan-2-sulfonamide (the product of step iii) (0.40 g) and 4-chloro-2-[[(2,3-difluorophenyl)methyl]thio]-6-[(1R)-1-methyl-2-(triphenylmethoxy)ethoxy]-pyrimidine (the product of Example 13, step iii) (0.41 g) according to the procedure outlined in Example ... | C[C@H](COC(c1ccccc1)(c1ccccc1)c1ccccc1)Oc1cc(NS(=O)(=O)c2ccc(C(=O)N3CCC3)o2)nc(SCc2cccc(F)c2F)n1 | null | null | null |
1,295,946 | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | null | 2013-01-01T00:05:00 | true | [NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]([C:10]2[C:14]3[N:15]=[CH:16][N:17]=[C:18]([C:19]4[C:27]5[O:26][CH2:25][O:24][C:23]=5[CH:22]=[CH:21][C:20]=4[O:28][CH2:29][CH3:30])[C:13]=3[NH:12][CH:11]=2)=[O:9])[CH2:3][CH2:2]1.Cl[C:32]([O:34][CH2:35][CH3:36])=[O:33]>>[CH2:35]([O:34][C:32]([N:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](... | CCOc1ccc2c(c1-c1ncnc3c(C(=O)NC4CCNCC4)c[nH]c13)OCO2 | CCOC(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Starting from 4-(5-ethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ylamide (example A175) and ethyl chloroformate the title compound was obtained as colorless solid. | CCOC(=O)N1CCC(NC(=O)c2c[nH]c3c(-c4c(OCC)ccc5c4OCO5)ncnc23)CC1 | null | null | null |
992,836 | ord_dataset-b6d8835b0c934476a36e6149e7597487 | null | 2010-01-01T00:09:00 | true | [CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:33]([O:35]C)=[O:34])=[CH:12][C:13]=3[N:14]3[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])[CH2:18][C:17]4[CH:27]=[C:28]([O:31][CH3:32])[CH:29]=[CH:30][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>O1CCOCC1.[OH-].[Na+]>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10... | COC(=O)c1ccc2c(C3CCCCC3)c3n(c2c1)CCN(CCN(C)C)Cc1cc(OC)ccc1-3 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 60 | 3 | The crude methyl 14-cyclohexyl-6-[2-(dimethylamino)ethyl]-3-methoxy-5,6,7,8-tetrahydroindolo[2,1-a][2,5]benzodiazocine-11-carboxylate was dissolved in dioxane (0.06 M) and to that solution 10 eq of an aqueous solution of NaOH (2N) were added. The solution was stirred at 60° C. for 3 h. The solvent was evaporated in vac... | COc1ccc2c(c1)CN(CCN(C)C)CCn1c-2c(C2CCCCC2)c2ccc(C(=O)O)cc21 | null | 28 | null |
1,702,269 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | Br[C:2]1[C:10]2[N:9]3[CH2:11][CH2:12][NH:13][C:14](=[O:15])[C:8]3=[C:7]([CH3:16])[C:6]=2[CH:5]=[C:4]([C:17]#[N:18])[CH:3]=1.[F:19][C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1>>[F:19][C:20]1[CH:25]=[C:24]([C:2]2[C:10]3[N:9]4[CH2:11][CH2:12][NH:13][C:14](=[O:15])[C:8]4=[C:7]([CH3:16])[C:6]=3[CH:5]=[C:4]([C:17]#[N... | Cc1c2n(c3c(Br)cc(C#N)cc13)CCNC2=O | OB(O)c1cccc(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, grey solid (61 mg, 76%), MS (ISP) m/z=320.5 [(M+H)+], mp 226° C., was prepared in accordance with the general method of example 1 from 6-bromo-10-methyl-1-oxo-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-8-carbonitrile (intermediate 16) (76 mg, 0.25 mmol) and commercially available 3-fluoro-phenylboroni... | Cc1c2n(c3c(-c4cccc(F)c4)cc(C#N)cc13)CCNC2=O | null | null | null |
1,111,690 | ord_dataset-375a420ee9b042918ddca20f02df37d3 | null | 2011-01-01T00:11:00 | true | [CH2:1]([O:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[C:11]([O:21][CH3:22])[N:12]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]Cl)=[C:8]([NH2:23])[N:7]=1)[CH2:2][CH2:3][CH3:4].[NH:24]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>>[CH2:1]([O:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[C:11]([O:21][CH3:22])[N:12]2[CH2:15][CH2:1... | C1CCCNCCC1 | CCCCOc1nc(N)c2nc(OC)n(CCCCCCl)c2n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared similarly to Intermediate 38 from 2-(butyloxy)-9-(5-chloropentyl)-8-(methyloxy)-9H-purin-6-amine and octahydroazocine. | CCCCOc1nc(N)c2nc(OC)n(CCCCCN3CCCCCCC3)c2n1 | null | null | null |
170,822 | ord_dataset-41558b7e18dd41999311b1762e0e13a3 | null | 1988-01-01T00:04:00 | true | [S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][C:7](=[O:9])[CH3:8].C([Li])CCC.[Cl:15][CH:16]([C:19]1[O:24][C:23](=[O:25])[C:22]2[CH:26]=[CH:27][CH:28]=[C:29]([C:30]([F:33])([F:32])[F:31])[C:21]=2[N:20]=1)[CH2:17][CH3:18]>O1CCCC1.CCCCCC>[Cl:15][CH:16]([CH2:17][CH3:18])[C:19]([NH:20][C:21]1[C:29]([C:30]([F:31])([F:32])[F:33])=[CH... | CC(=O)Nc1nccs1 | CCC(Cl)c1nc2c(C(F)(F)F)cccc2c(=O)o1 | null | [Li]CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCCCCC | null | null | null | null | null | null | null | null | null | null | null | Using the procedure of Step A of Example 6, a solution of 16.58 g of N-(2-thiazolyl)-acetamide in 340 ml of tetrahydrofuran, 155 ml of a solution of butyllithium in hexane and a solution of 17 g of the product of Step A in 170 ml of tetrahydrofuran were reacted to obtain 5.5 g of 2-[(2-chloro-1-oxo-butyl)-amino]-β-oxo-... | CCC(Cl)C(=O)Nc1c(C(=O)CC(=O)Nc2nccs2)cccc1C(F)(F)F | null | 21.7 | null |
479,335 | ord_dataset-21c1b1c06c7e4e09a38b5b1c71a32e52 | null | 2000-01-01T00:10:00 | true | [NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.Cl[C:7]1[N:8]=[C:9]([NH:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]3[O:27][CH2:28][O:29][C:23]=3[CH:22]=2)[C:10]2[CH:15]=[C:14]([CH2:16][CH3:17])[S:13][C:11]=2[N:12]=1>>[N:1]1([C:7]2[N:8]=[C:9]([NH:18][CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]4[O:27][CH2:28][O:29][C:23]=4[CH:22]=3... | CCc1cc2c(NCCc3ccc4c(c3)OCO4)nc(Cl)nc2s1 | c1nc[nH]n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Following the procedure of Example 97, the reaction of 1,2,4-triazole with 2-chloro-6-ethyl-4-(3,4-methylenedioxyphenethylamino)-thieno-[2,3-d]-pyrimidine gives 2-(1,2,4-triazol-1-yl)-6-ethyl-4-(3,4-methylenedioxyphenethylamino)-thieno-[2,3-d]-pyrimidine. | CCc1cc2c(NCCc3ccc4c(c3)OCO4)nc(-n3cncn3)nc2s1 | null | null | null |
352,679 | ord_dataset-127eb5fdd5b4402e92b51d0b55a5dcb5 | null | 1997-01-01T00:01:00 | true | [Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:11])[CH:3]=1.[C:12]1([SiH:18]2[CH2:23][CH2:22][C:21](CCC=CC)([CH:24]3[CH2:29][CH2:28][CH:27](O)[CH2:26][CH2:25]3)[CH2:20][CH2:19]2)C=[CH:16][CH:15]=[CH:14][CH:13]=1>>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][C@H:27]2[CH2:26][CH2:25][C@H:24]([CH:21]3[CH2:20... | CC=CCCC1(C2CCC(O)CC2)CC[SiH](c2ccccc2)CC1 | O=C(O)c1ccc(Cl)cc1F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The general procedure of Example 31 was repeated using 4-chloro-2-fluorobenzoic acid and 4-(4-phenyl-(3-pentenyl)-4-silacyclohexyl)cyclohexanol, thereby obtaining the intended product. | C=CCCC[SiH]1CCC([C@H]2CC[C@H](OC(=O)c3ccc(Cl)cc3F)CC2)CC1 | null | null | null |
890,386 | ord_dataset-11068b1e475b4c5b82e56726ab0dddb7 | null | 2009-01-01T00:07:00 | true | [CH3:1][O:2][C:3](=[O:40])[CH:4]([C:9]1[CH:10]=[C:11]([C:26]2[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[C:28]([C:36]([F:39])([F:38])[F:37])[CH:27]=2)[CH:12]=[C:13]([O:15]C2C=CC=C(C(F)(F)F)C=2)[CH:14]=1)[CH2:5][CH:6]([CH3:8])[CH3:7].[F:41][C:42]1[CH:43]=[C:44](B(O)O)[CH:45]=[C:46]([F:48])[CH:47]=1>>[CH3:1][O:2... | OB(O)c1cc(F)cc(F)c1 | COC(=O)C(CC(C)C)c1cc(Oc2cccc(C(F)(F)F)c2)cc(-c2cc(C(F)(F)F)cc(C(F)(F)F)c2)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared in 15% yield from 2-[3′,5′-bis-trifluoromethyl-5-(3-trifluoromethyl-phenoxy)-biphenyl-3-yl]-4-methyl-pentanoic acid methyl ester (prepared in Example C) and 3,5-difluoro-phenylboronic acid under the conditions described in Example 15, step (g). | COC(=O)C(CC(C)C)c1cc(Oc2cc(F)cc(F)c2)cc(-c2cc(C(F)(F)F)cc(C(F)(F)F)c2)c1 | null | 15 | null |
1,444,867 | ord_dataset-275a3da8f45f4536ad29727f0ef9ba66 | null | 2014-01-01T00:06:00 | true | C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]([C:18]2[CH:41]=[CH:40][C:21]3[N:22]([CH2:36][CH2:37][O:38][CH3:39])[C:23]([NH:25][C:26]4[S:27][C:28]5[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:29]=5[N:30]=4)=[N:24][C:20]=3[CH:19]=2)=[O:17])[CH2:10][CH2:9]1)=O)(C)(C)C>Cl.O1CCOCC1>[ClH:35].[ClH:35].[NH:8]1[CH2:13][... | COCCn1c(Nc2nc3ccc(Cl)cc3s2)nc2cc(C(=O)NCC3CCN(C(=O)OC(C)(C)C)CC3)ccc21 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | null | 2-(6-Chloro-benzothiazol-2-ylamino)-1-(2-methoxy-ethyl)-1H-benzoimidazole-5-carboxylic acid (piperidin-4-ylmethyl)-amide dihydrochloride (145 mg) was prepared by following General Procedure L starting from 4-({[2-(6-chloro-benzothiazol-2-ylamino)-1-(2-methoxy-ethyl)-1H-benzoimidazole-5-carbonyl]-amino}-methyl)piperidin... | COCCn1c(Nc2nc3ccc(Cl)cc3s2)nc2cc(C(=O)NCC3CCNCC3)ccc21 | null | 284.8 | null |
486,940 | ord_dataset-7b02d32cc502407f94aea8e5caf405a2 | null | 2000-01-01T00:12:00 | true | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([N:10]3[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]3[C:16]([O:18]CC3C=CC=CC=3)=[O:17])=[N:7][C:6]=2[CH:26]=1.[OH-].[Li+]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([N:10]3[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]3[C:16]([OH:18])=[O:17])=[N:7][C:6]=2[CH:26]=1 | O=C(OCc1ccccc1)[C@@H]1CCCCN1c1nc2cc(Cl)ccc2o1 | null | null | [Li+] | [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 | The title compound was prepared by a similar method to Preparation 3 from benzyl (2S)-1-(5-chloro-1,3-benzoxazol-2-yl)-2-piperidinecarboxylate [see Preparation 28] and 1N aqueous lithium hydroxide solution to afford (2S)-1-(5-chloro-1,3-benzoxazol-2-yl)-2-piperidinecarboxylic acid as an oil. | O=C(O)[C@@H]1CCCCN1c1nc2cc(Cl)ccc2o1 | null | null | null |
106,140 | ord_dataset-e7e9fe3dd42b4f499d5b17fe63bbf336 | null | 1983-01-01T00:06:00 | true | [OH:1][CH2:2][C:3]1[O:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:30]>>[Cl:30][CH2:7][C:6]1[O:9][C:3]([CH:2]=[O:1])=[CH:4][CH:5]=1 | ClC(Cl)(Cl)Cl | O=Cc1ccc(CO)o1 | null | c1ccc(P(c2ccccc2)c2ccccc2)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 | A mixture of 5-hydroxymethylfurfuraldehyde (0.5 g, 4 mmol) and triphenylphosphine (1.3 g, 5 mmol) in dry carbon tetrachloride (3 ml) was heated at reflux for 30 min and then filtered to give an unstable 1 M solution of 5-chloromethylfurfuraldehyde. | O=Cc1ccc(CCl)o1 | null | null | null |
93,090 | ord_dataset-f0d0fe3f599c471ca1c011dbbcdeeff2 | null | 1982-01-01T00:04:00 | true | [N:1]([O-])=O.[Na+].[CH3:5][N:6]([CH2:8][CH2:9][CH:10]([C:16]1[CH:25]=[CH:24][C:19](C(NN)=O)=[CH:18][CH:17]=1)[C:11]1[NH:12][CH:13]=[CH:14][N:15]=1)[CH3:7].C(=O)([O-])[O-].[Na+].[Na+]>O.Cl>[NH2:1][C:19]1[CH:24]=[CH:25][C:16]([CH:10]([C:11]2[NH:12][CH:13]=[CH:14][N:15]=2)[CH2:9][CH2:8][N:6]([CH3:7])[CH3:5])=[CH:17][CH:1... | O=N[O-] | CN(C)CCC(c1ccc(C(=O)NN)cc1)c1ncc[nH]1 | null | Cl | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | null | 0.5 | A solution of sodium nitrite (0.5 g) in water (5 ml) was added dropwise to a stirred solution of 4-[3-(N,N-dimethylamino)-1-(imidazol-2-yl)propyl]benzoic acid hydrazide (2.0 g) in 2 N hydrochloric acid (10.5 ml) and water (50 ml) at 0° to 5° C. After 30 min. the solution was basified by adding 2 N sodium carbonate (15 ... | CN(C)CCC(c1ccc(N)cc1)c1ncc[nH]1 | null | null | null |
88,579 | ord_dataset-6dbd68e494f94ae796187f53698183da | null | 1981-01-01T00:11:00 | true | [CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:21][CH2:20]1>CS(C)=O.[OH-].[Na+]>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:17][CH2:18][N:19]2[CH2:24][... | ClCCN1CCN(c2ccccc2)CC1 | Oc1ccc(OCc2ccccc2)cc1 | null | [Na+] | [OH-] | 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 | null | null | 26.25 ml 4 N NaOH (0.105 mol) was added to a stirred mixture of 21.0 g (0.105 mol) 4-benzyloxyphenol and 22.5 g (0.1 mol) of 1-(2-chloroethyl)-4-phenylpiperazine in 250 ml DMSO and the reaction was heated at 60° for 60 min. After cooling, the stirred mixture was diluted with 50 ml 1 N NaOH solution and the resulting cr... | c1ccc(COc2ccc(OCCN3CCN(c4ccccc4)CC3)cc2)cc1 | null | null | null |
785,194 | ord_dataset-4ad5db8537994579bef51f16dd8bf0bd | null | 2007-01-01T00:08:00 | true | C([O:14][C:15]1[C:16]2[C:44](=[O:45])[N:43]([CH2:46][C:47]3[CH:52]=[CH:51][C:50]([F:53])=[CH:49][CH:48]=3)[CH2:42][C:17]=2[C:18]([O:25][S:26]([CH2:29][CH2:30][N:31]2[C:39](=[O:40])[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:32]2=[O:41])(=[O:28])=[O:27])=[C:19]2[C:24]=1[N:23]=[CH:22][CH:21]=[CH:20]2)(C1C=CC=CC=1)C... | O=C1c2c(c(OS(=O)(=O)CCN3C(=O)c4ccccc4C3=O)c3cccnc3c2OC(c2ccccc2)c2ccccc2)CN1Cc1ccc(F)cc1 | null | null | CC[SiH](CC)CC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 0.5 | To a solution of 268 (12.2 mg, 0.017 mmol) dissolved in dichloromethane (1 mL) was added trifluoroacetic acid (100 μl) and triethylsilane (200 μl). The reaction mixture was stirred at room temperature for ½ hours under an inert atmosphere then concentrated in vacuo. The residue was triturated with diethyl ether/hexane ... | O=C1c2c(c(OS(=O)(=O)CCN3C(=O)c4ccccc4C3=O)c3cccnc3c2O)CN1Cc1ccc(F)cc1 | null | null | null |
457,216 | ord_dataset-2501595af7f242268dbaab34c9e7ae56 | null | 2000-01-01T00:02:00 | true | [CH2:1]([SH:5])[CH2:2][CH2:3][SH:4].C(=O)([O-])[O-].[K+].[K+].F[C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:33])[C:20]([N:30]([CH3:32])[CH3:31])([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:21][CH3:22])=[CH:15][CH:14]=1>CC(N(C)C)=O>[SH:4][CH2:3][CH2:2][CH2:1][S:5][C:13]1[CH:14]=[CH:15][C:16]([C:19](=[O:33])[C... | CCC(Cc1ccccc1)(C(=O)c1ccc(F)cc1)N(C)C | SCCCS | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)N(C)C | null | null | null | null | null | null | null | null | null | null | 50 | 12 | 32.5 g (0.3 mol) of 1,3-propanedithiol are dissolved in 50 ml of dry dimethylacetamide, and the solution is heated to about 50° C. together with 13.8 g (0.1 mol) of potassium carbonate. 15.0 g (0.05 mol) of 1-(4-fluorophenyl)-2-dimethylamino-2-benzyl-butan-1-one in 30 ml of dry dimethylacetamide are added dropwise. The... | CCC(Cc1ccccc1)(C(=O)c1ccc(SCCCS)cc1)N(C)C | null | null | null |
1,015,915 | ord_dataset-f024e9664ab64906a71a2ff6004cb3d0 | null | 2010-01-01T00:12:00 | true | [F:1][C:2]([F:28])([F:27])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][C:11]([CH2:25][OH:26])=[C:12]([CH2:14][N:15]3[CH2:20][CH2:19][CH:18]([C:21]([F:24])([F:23])[F:22])[CH2:17][CH2:16]3)[N:13]=2)=[CH:5][CH:4]=1.[H-].[Na+].[F:31][CH:32]([F:43])[O:33][C:34]1[CH:41]=[C:40](F)[CH:39]=[CH:38][C:35]=1[C:36]#[N:37].O>CN(C)C=O>[F:31... | OCc1sc(-c2ccc(C(F)(F)F)cc2)nc1CN1CCC(C(F)(F)F)CC1 | N#Cc1ccc(F)cc1OC(F)F | 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 | 5 | 0.5 | To a solution of 3 g of [2-(4-trifluoromethyl-phenyl)-4-(4-trifluoromethyl-piperidin-1-ylmethyl)-thiazol-5-yl]-methanol in 12 mL of dimethylformamide at 5° C. was added 319 mg of a 55% suspension of sodium hydride in mineral oil. The resulting mixture was stirred for 30 minutes at 5° C. 4.7 mL of the resulting solution... | N#Cc1ccc(OCc2sc(-c3ccc(C(F)(F)F)cc3)nc2CN2CCC(C(F)(F)F)CC2)cc1OC(F)F | null | 82.3 | null |
1,117,487 | ord_dataset-4226e9b4f9f845db967ed997270dcafc | null | 2011-01-01T00:12:00 | true | C([N:4]1[C:46]2[C:41](=[CH:42][CH:43]=[C:44]([Cl:47])[CH:45]=2)[C:6]2([CH:11]([C:12]3[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=3[O:19][C:20]([CH2:30][CH3:31])([CH2:28][CH3:29])[C:21]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[O:22])[CH2:10][C:9](=[S:32])[NH:8][CH:7]2[C:33]2[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=... | CCC(CC)(Oc1ccc(Cl)cc1C1CC(=S)NC(c2cc(F)ccc2C)C12C(=O)N(C(C)=O)c1cc(Cl)ccc12)C(=O)NS(C)(=O)=O | null | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 0.25 | A mixture of chiral (2′S, 3S, 4′R)-1-acetyl-6-chloro-4′-[5-chloro-2-(2-methanesulfonylamino-1,1-diethyl-2-oxo-ethoxy)-phenyl]-2′-(5-fluoro-2-methyl-phenyl)-6′-thioxo spiro[3H-indole-3,3′-piperidine]-2(1H)-one (45 mg) and K2CO3 (30 mg) in methanol (2 mL) was stirred at room temperature for 15 min, and then the mixture w... | CCC(CC)(Oc1ccc(Cl)cc1C1CC(=S)NC(c2cc(F)ccc2C)C12C(=O)Nc1cc(Cl)ccc12)C(=O)NS(C)(=O)=O | null | 82.5 | null |
847,080 | ord_dataset-e2b35e721c2741999b0005d12691f9fe | null | 2008-01-01T00:10:00 | true | O.[OH-].[Li+].Cl.[CH3:5][O:6][C:7](=[O:11])[CH2:8][CH2:9][NH2:10].Br[CH2:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[N+:21]([O-:23])=[O:22]>CN(C)C=O>[CH3:5][O:6][C:7](=[O:11])[CH2:8][CH2:9][NH:10][CH2:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[N+:21]([O-:23])=[O:22] | O=[N+]([O-])c1ccc(Cl)cc1CBr | COC(=O)CCN | null | Cl | [Li+] | [OH-] | 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 | 0.33 | A mixture of 4 Å molecular sieve powder (16.9 g) and lithium hydroxide monohydrate (1.80 g, 43 mmol) in N,N-dimethylformamide (100 ml) was stirred at room temperature for 20 minutes. β-Alanine methyl ester hydrochloride (5.0 g, 35.8 mmol) was added and the mixture stirred for a further 45 minutes. 2-(Bromomethyl)-4-chl... | COC(=O)CCNCc1cc(Cl)ccc1[N+](=O)[O-] | null | null | null |
992,615 | ord_dataset-b6d8835b0c934476a36e6149e7597487 | null | 2010-01-01T00:09:00 | true | Cl.[F:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]1[O:14][C:13]([C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([C@H:24]3[CH2:29][CH2:28][C@H:27]([CH2:30][NH:31]C(=O)OC(C)(C)C)[CH2:26][CH2:25]3)=[CH:20][CH:19]=2)=[O:16])=[N:12][N:11]=1>O1CCOCC1>[NH2:31][CH2:30][C@H:27]1[CH2:28][CH2:29][C@H:24]([C:21]2[CH:20]=[CH:19... | CC(C)(C)OC(=O)NC[C@H]1CC[C@H](c2ccc(NC(=O)c3nnc(Nc4ccccc4F)o3)cc2)CC1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | 18 | 4M HCl in 1,4-dioxane (1 mL) was added to tert-butyl [(trans-4-{4-[({5-[(2-fluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]phenyl}cyclohexyl)-methyl]carbamate (Example 618) (50 mg, 0.10 mmol) and the suspension stirred for 18 hours. All volatiles were removed in vacuo and the residue triturated with Et2O (3 mL)... | NC[C@H]1CC[C@H](c2ccc(NC(=O)c3nnc(Nc4ccccc4F)o3)cc2)CC1 | null | null | null |
898,564 | ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded | null | 2009-01-01T00:08:00 | true | [N:1]1([C:7](=[O:15])[CH2:8][N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(=O)(O)[O-].[Na+].[C:21](Cl)([Cl:23])=[O:22]>ClCCl>[N:1]1([C:7](=[O:15])[CH2:8][N:9]2[CH2:10][CH2:11][N:12]([C:21]([Cl:23])=[O:22])[CH2:13][CH2:14]2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1 | O=C(Cl)Cl | O=C(CN1CCNCC1)N1CCOCC1 | 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 | 0 | 0.5 | To the solution of 1-morpholin-4-yl-2-piperazin-1-yl-ethanone (0.5 g, 2.34 mmol) (Oakwood) in dichloromethane (15 mL) was added saturated sodium bicarbonate solution (15 mL). The reaction mixture was cooled to 0° C. and then followed by the dropwise addition of phosgene (20% in toluene, 2.22 mL, 4.21 mmol). The reactio... | O=C(Cl)N1CCN(CC(=O)N2CCOCC2)CC1 | null | null | null |
952,819 | ord_dataset-3feb2a95f66e4706a4a50c977ccd9bf8 | null | 2010-01-01T00:04:00 | true | [CH2:1]([C:3]1[CH:4]=[C:5]([CH2:11][C@@H:12]([NH:16][C:17]([N:19]2[CH2:24][CH2:23][CH:22]([N:25]3[CH2:31][CH2:30][C:29]4[CH:32]=[CH:33][CH:34]=[CH:35][C:28]=4[NH:27][C:26]3=[O:36])[CH2:21][CH2:20]2)=[O:18])[C:13](O)=[O:14])[CH:6]=[CH:7][C:8]=1[CH2:9][CH3:10])[CH3:2].[CH3:37][N:38]1[CH2:44][CH2:43][CH2:42][N:41]([CH:45]... | CCc1ccc(C[C@@H](NC(=O)N2CCC(N3CCc4ccccc4NC3=O)CC2)C(=O)O)cc1CC | CN1CCCN(C2CCNCC2)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared analogously to Example 9i) from 400 mg (0.81 mmol) (R)-3-(3,4-diethyl-phenyl)-2-{[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyl]-amino}-propionic acid and 200 mg (1.01 mmol) 1-methyl-4-piperidin-4-yl-[1,4]diazepan. | CCc1ccc(C[C@@H](NC(=O)N2CCC(N3CCc4ccccc4NC3=O)CC2)C(=O)N2CCC(N3CCCN(C)CC3)CC2)cc1CC | null | null | null |
595,392 | ord_dataset-278fb6af8a994ac69e4d95e6e6eff756 | null | 2003-01-01T00:05:00 | true | [N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][NH2:8].[CH2:9]([O:11][C:12](=[O:19])[CH:13]([CH:17]=O)[C:14](=O)[CH3:15])[CH3:10].N1C=CC=CC=1>C(O)C>[CH2:9]([O:11][C:12]([C:13]1[C:14]([CH3:15])=[N:8][N:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH:17]=1)=[O:19])[CH3:10] | NNc1ccccn1 | CCOC(=O)C(C=O)C(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | Similar to Example 1, equimolar amounts of 2-pyridylhydrazine and 2-formyl-3-oxo-butyric acid ethyl ester were combined in a solution of 50% pyridine in ethanol. Analysis showed that the resulting solid was determined to be the named product (m.p. 49° C.-50° C.). | CCOC(=O)c1cn(-c2ccccn2)nc1C | null | null | null |
166,586 | ord_dataset-5c25f386f4664070a72d578feacedf86 | null | 1987-01-01T00:12:00 | true | [CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C:14]([OH:16])=[O:15])[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][C@@H:18]1[CH2:23][CH2:22][CH2:21][CH2:20][C@H:19]1O.C1CCC(N=C=NC2CCCCC2)CC1>C1COCC1.CN(C)C1C=CN=CC=1.CC(O)=O>[CH3:17][C@@H:18]1[CH2:23][CH2:22][CH2:21][CH2:20][C@H:19]1[O:15][C:14](=[O:16])[C@@H... | C[C@@H]1CCCC[C@H]1O | C[C@@H](NC(=O)OCc1ccccc1)C(=O)O | null | C(=NC1CCCCC1)=NC1CCCCC1 | CN(C)c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | N-Benzyloxycarbonyl-D-alanine (2.5 mmol. 0.556 g) and trans-2-methylcyclohexanol (3 equivalents, 1 mL) were dissolved in 7 mL THF at room temperature, followed by the addition of 70 mg 4-dimethylaminopyridine. DCC (2.5 mmol, 0.515 g) was then introduced with stirring. The solution turned cloudy immediately and was stir... | C[C@@H]1CCCC[C@H]1OC(=O)[C@@H](C)NC(=O)OCc1ccccc1 | null | null | null |
1,055,337 | ord_dataset-373415d3e0e54004837cf4831e67666f | null | 2011-01-01T00:05:00 | true | [CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[C:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:12][O:13][C:14]=2[CH3:15])[N:5]=[N:4][C:3]=1[C:22]([OH:24])=O.[CH:25]1([NH2:28])[CH2:27][CH2:26]1>>[CH:25]1([NH:28][C:22]([C:3]2[N:4]=[N:5][C:6]([O:8][CH2:9][C:10]3[C:11]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4... | NC1CC1 | Cc1cc(OCc2c(-c3ccccc3)noc2C)nnc1C(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | As described for example 44, 4-methyl-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid (200 mg, 0.61 mmol) was converted, using cyclopropylamine instead of 4-amino-tetrahydropyran, to the title compound (SiO2, heptane:ethyl acetate=100:0 to 60:40, 122 mg, 54%) which was obtained as a white solid.... | Cc1cc(OCc2c(-c3ccccc3)noc2C)nnc1C(=O)NC1CC1 | null | 54 | null |
1,441,743 | ord_dataset-275a3da8f45f4536ad29727f0ef9ba66 | null | 2014-01-01T00:06:00 | true | [CH2:1]([C:3]1[CH:4]=[N:5][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([N:15]3[CH2:19][CH2:18][C@H:17]([NH:20]C(=O)OC(C)(C)C)[C:16]3=[O:28])[CH2:11][CH2:10]2)=[N:7][CH:8]=1)[CH3:2]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH2:20][C@H:17]1[CH2:18][CH2:19][N:15]([CH:12]2[CH2:13][CH2:14][N:9]([C:6]3[N:7]=[CH:8][C:3]([CH2:1][CH3:2])=[CH:4][N:5]=3... | CCc1cnc(N2CCC(N3CC[C@H](NC(=O)OC(C)(C)C)C3=O)CC2)nc1 | 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 (S)-tert-butyl 1-(1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)-2-oxopyrrolidin-3-ylcarbamate (1 g, 2.6 mmol) in 50% TFA/CH2Cl2 (10 mL) was stirred at ambient temperature for 1 hour. The mixture was concentrated in vacuo. The residue was dissolved in CH2Cl2 (100 mL) and washed with 1N NaOH (100 mL) and brine. ... | CCc1cnc(N2CCC(N3CC[C@H](N)C3=O)CC2)nc1 | null | 100 | null |
1,232,394 | ord_dataset-e96f5a2842f14e5380461c234100f05a | null | 2012-01-01T00:12:00 | true | [S-:1][C:2]#[N:3].[K+].[NH2:5][C:6]1[CH:33]=[CH:32][C:9]([O:10][C:11]2[CH:12]=[CH:13][C:14]([CH3:31])=[C:15]([NH:17][C:18](=[O:30])[C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]4([C:28]#[N:29])[CH2:27][CH2:26]4)[CH:20]=3)[CH:16]=2)=[CH:8][CH:7]=1.BrBr>C(O)(=O)C>[NH2:3][C:2]1[S:1][C:7]2[CH:8]=[C:9]([O:10][C:11]3[CH:12]=[CH... | Cc1ccc(Oc2ccc(N)cc2)cc1NC(=O)c1cccc(C2(C#N)CC2)c1 | N#C[S-] | null | BrBr | [K+] | 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 | 0.17 | Potassium thiocyanate (7.00 g, 72 mmol) was suspended in acetic acid (120 mL) and the mixture was stirred at room temperature for 10 min. To the obtained solution was added a solution of N-[5-(4-aminophenoxy)-2-methylphenyl]-3-(1-cyanocyclopropyl)benzamide (6.90 g, 18 mmol) in acetic acid (120 mL), and the mixture was ... | Cc1ccc(Oc2ccc3nc(N)sc3c2)cc1NC(=O)c1cccc(C2(C#N)CC2)c1 | null | 79.1 | null |
1,384,524 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | [NH2:1][N:2]1[N:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:16].[CH:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][C:18]=1[CH2:27][C:28](O)=[O:29]>>[CH:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][C:18]=1[CH2:27][C:28]([NH:1][N:2]1... | Nn1nc(C(F)(F)F)c2ccccc2c1=O | O=C(O)Cc1ccc2ccccc2c1 | null | null | null | null | null | null | null | 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 of Example 11B and 2-napthylacetic acid were treated using a method similar to that described in Example 57 to give the title compound. 1H NMR (500 MHz, DMSO-d6/Deuterium Oxide) δ ppm 8.44 (ddd, J=8.0, 1.4, 0.6 Hz, 1H), 8.12-8.16 (m, 1H), 8.01-8.09 (m, 2H), 7.87-7.97 (m, 4H), 7.48-7.59 (m, 3H), 3.91 (s, 2H)... | O=C(Cc1ccc2ccccc2c1)Nn1nc(C(F)(F)F)c2ccccc2c1=O | null | null | null |
1,467,269 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | C[O:2][C:3]([C:5]1([NH:14][C:15](=[O:36])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH2:25][C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[CH:30]=3)([F:28])[F:27])[CH:17]=2)[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)=[O:4].[OH-].[Li+].Cl>C1COCC1.O>[Cl:35][C:31]1[CH:30]=[C:29]([C:2... | COC(=O)C1(NC(=O)c2ccc(OC)c(OCC(F)(F)c3cccc(Cl)c3)c2)Cc2ccccc2C1 | null | null | Cl | [Li+] | [OH-] | 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 | 72 | 20 mg of the compound of step 3 were dissolved in 5 ml of a mixture of THF and water (9:1), and 1.9 mg (77.5 μmol) of lithium hydroxide were added. After stirring at room temperature for 3 d, the mixture was acidified with 1 M hydrochloric acid and evaporated. The residue was purified by silica gel chromatography (DCM/... | COc1ccc(C(=O)NC2(C(=O)O)Cc3ccccc3C2)cc1OCC(F)(F)c1cccc(Cl)c1 | null | 41.1 | null |
362,759 | ord_dataset-0b24d1f58a024ed7bc2bda95b2430c72 | null | 1997-01-01T00:04:00 | true | [OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][C@@H:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:10][C:9]2=[O:19])=[CH:4][CH:3]=1.[C:20](O)(=[O:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:20]([O:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:12][C@@H:11]([C:13]3[CH:18... | CCCCCC(=O)O | O=C1O[C@H](c2ccccc2)CN1c1ccc(O)cc1 | null | C(=NC1CCCCC1)=NC1CCCCC1 | CN(C)c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | null | 0.50 g (1.96 mM) of (5R)-3-(4-hydroxyphenyl)-5-phenyl-2-oxazolidinone synthesized in Example 2, 0.26 g of hexanoic acid and 20 ml of methylene chloride were placed in 50 ml-round bottomed flask, followed by stirring to form a solution. To the solution, 0.43 g (2.08 mM) of N,N'-dicyclohexylcarbodiimide and 0.10 g of 4-d... | CCCCCC(=O)Oc1ccc(N2C[C@@H](c3ccccc3)OC2=O)cc1 | null | 52 | null |
157,877 | ord_dataset-58ec6779628e43e2b3f0972725f262e6 | null | 1987-01-01T00:05:00 | true | [BH4-].[Na+].[CH3:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]2[CH2:13][CH2:14][C:15]([CH2:21][CH:22]=[CH2:23])([CH2:18][CH:19]=[CH2:20])[C:16](=[O:17])[C:5]=12>C(O)C>[CH3:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]2[CH2:13][CH2:14][C:15]([CH2:18][CH:19]=[CH2:20])([CH2:21][CH:22]=[CH2:23])[CH... | C=CCC1(CC=C)CCn2c(c(C)c3ccccc32)C1=O | null | null | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 25 | 24 | Sodium borohydride (10.53 g, 270 mmol) was added portionwise upon cooling to a solution of 6,7,8,9-tetrahydro-10-methyl-8,8-bis(2-propenyl)pyrido[1,2-a]indol-9-one (12.8 g, 45.8 mmol), in ethanol (350 mL) at 25° C. The reaction mixture was stirred at room temperature for 24 hours. The solvent was removed in vacuo to ne... | C=CCC1(CC=C)CCn2c(c(C)c3ccccc32)C1O | null | 98 | null |
723,675 | ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | null | 2006-01-01T00:08:00 | true | [CH:1]1([CH2:4][NH:5][C:6]2[C:7]([S:25][CH3:26])=[N:8][N:9]3[C:14]([C:15]4[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=4[O:23][CH3:24])=[CH:13][CH:12]=[CH:11][C:10]=23)[CH2:3][CH2:2]1.[O:27]1[CH2:32][CH2:31][CH:30]([CH:33]=O)[CH2:29][CH2:28]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>O1CCCC1.C(O... | O=CC1CCOCC1 | COc1cc(C)cc(C)c1-c1cccc2c(NCC3CC3)c(SC)nn12 | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | 1 | After dissolving N-cyclopropylmethyl-N-[7-(2-methoxy-4,6-dimethylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]amine (100 mg) in tetrahydrofuran (2 mL), tetrahydro-2H-4-pyrancarbaldehyde (78 mg) [CAS No. 50675-18-8] and sodium triacetoxyborohydride (87 mg) were added, and the mixture was stirred for 1 hour. Sat... | COc1cc(C)cc(C)c1-c1cccc2c(N(CC3CCOCC3)CC3CC3)c(SC)nn12 | null | 55.2 | null |
1,190,105 | ord_dataset-9cd817a75dfc4fe7ad19d4232772d5ff | null | 2012-01-01T00:07:00 | true | Br[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([NH2:12])=[C:4]([N+:13]([O-:15])=[O:14])[CH:3]=1.[F:16][C:17]([F:28])([F:27])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1B(O)O>CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[N+:13]([C:4]1[C:5]([NH2... | Nc1c([N+](=O)[O-])cc(Br)cc1C(F)(F)F | OB(O)c1ccccc1C(F)(F)F | null | Cl[Pd]Cl | [Fe+2] | c1ccc(P(c2ccccc2)[c-]2cccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 90 | 18 | 4-Bromo-2-nitro-6-trifluoromethyl-phenylamine (10.0 g, 35.2 mmol, as prepared in the previous step), 2-trifluoromethylphenylboronic acid (8.70 g, 45.8 mmol), and (dppf)PdCl2 DCM (1.44 g, 1.76 mmol) were placed in a 500 mL round-bottom flask equipped with a magnetic stir bar and reflux condenser. The flask was evacuated... | Nc1c([N+](=O)[O-])cc(-c2ccccc2C(F)(F)F)cc1C(F)(F)F | null | 92 | null |
558,631 | ord_dataset-f483e698250b4da0a84f425c7bfa965a | null | 2002-01-01T00:08:00 | true | Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[C:6]([N:19]([C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1)[CH:20]=[O:21])=[C:5]2[O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[Li]CCCC.[CH3:41][C:42]([CH3:44])=[O:43].[NH4+].[Cl-]>C1COCC1>[F:1... | CC(C)=O | O=CN(c1cccnc1)c1c(OCc2ccccc2)c2cc(Br)ccc2n1Cc1ccc(F)cc1 | null | [Cl-] | [Li]CCCC | [NH4+] | 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 | -100 | 0.5 | To a solution of 201 mg of {5-Bromo-1-[(4-fluorophenyl)methyl]-3-(phenylmethoxy)indol-2-yl}-N-(3-pyridyl)formamide in 10 mL of THF at −100° C. was added 0.5 mL of n-BuLi (1.6 M in hexanes) and the mixture was stirred at −100° C. for 30 min. To this cold solution, 190 μL of acetone was added and the reaction mixture was... | CC(C)(O)c1ccc2c(c1)c(OCc1ccccc1)c(N(C=O)c1cccnc1)n2Cc1ccc(F)cc1 | null | null | null |
1,477,355 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [O:1]=[C:2]1[CH:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH2:5][CH2:4][NH:3]1.S(Cl)([Cl:16])(=O)=O.C(=O)([O-])O.[Na+]>C1COCC1>[Cl:16][C:7]1([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH2:5][CH2:4][NH:3][C:2]1=[O:1] | CCOC(=O)C1CCCNC1=O | O=S(=O)(Cl)Cl | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 18 | To a mixture of ethyl 2-oxopiperidine-3-carboxylate (30 g) in THF (300 mL) was added dropwise sulfuryl chloride (14.2 mL) at 0° C.-5° C., and the mixture was stirred at room temperature for 18 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution (300 mL) at 0° C., and the mixture w... | CCOC(=O)C1(Cl)CCCNC1=O | null | null | null |
650,705 | ord_dataset-271c0b74f4794a06992957029b3151ba | null | 2004-01-01T00:10:00 | true | Cl.[OH:2][C:3]1[CH:13]=[CH:12][C:6]([C:7](=N)OCC)=[CH:5][CH:4]=1.[NH2:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[NH:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)[C:18]#[N:19]>CO>[OH:2][C:3]1[CH:13]=[CH:12][C:6]([C:7]2[N:23]([CH:24]3[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]3)[C:22]3[CH:21]=[CH:20][C:17]([C:... | N#Cc1ccc(NC2CCCCC2)c(N)c1 | CCOC(=N)c1ccc(O)cc1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | null | A solution of ethyl 4-hydroxybenzimidate hydrochloride (5, 1.26 g, 6.7 mmol) and compound 4 (1.5 g, 5.0 mmol) in methanol (10 mL) was refluxed overnight under a nitrogen atmosphere. The reaction mixture was cooled to rt, filtered, and washed with methanol to afford 6 as a pinkish brown solid (1.26 g, 68%). ESI-MS m/e 3... | N#Cc1ccc2c(c1)nc(-c1ccc(O)cc1)n2C1CCCCC1 | null | 79.4 | null |
54,976 | ord_dataset-159c363342e44b539e7a5975c873e30d | null | 1979-01-01T00:05:00 | true | Cl.[S:2]1[CH:6]=[CH:5][C:4]2[CH:7]([NH2:12])[CH2:8][CH2:9][CH2:10][CH2:11][C:3]1=2.[O-:13][C:14]#[N:15].[K+]>O>[S:2]1[CH:6]=[CH:5][C:4]2[CH:7]([NH:12][C:14]([NH2:15])=[O:13])[CH2:8][CH2:9][CH2:10][CH2:11][C:3]1=2 | NC1CCCCc2sccc21 | N#C[O-] | null | Cl | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | null | 1 | A mixture of 50 grams of 5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophen-4-amine hydrochloride in 100 ml. of water is stirred at about 15° C. and a solution of 23.1 grams of potassium cyanate in 100 ml. of water is added dropwise. After completion of the addition, the mixture is warmed slowly to 70°-75° C. and held there f... | NC(=O)NC1CCCCc2sccc21 | null | null | null |
136,829 | ord_dataset-a1d4c9f5edd844798727d514977ca73e | null | 1985-01-01T00:11:00 | true | Br[C:2]1[C:3]2[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][OH:14])=[CH:8][C:4]=2[S:5][C:6]=1[CH3:7].C([Li])CCC.[C:20](=[O:22])=[O:21].C1(C)C=CC=CC=1>CCOCC>[OH:14][CH2:13][CH2:12][C:9]1[CH:10]=[CH:11][C:3]2[C:2]([C:20]([OH:22])=[O:21])=[C:6]([CH3:7])[S:5][C:4]=2[CH:8]=1 | Cc1sc2cc(CCO)ccc2c1Br | O=C=O | null | [Li]CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | CCOCC | null | null | null | null | null | null | null | null | null | null | null | Successive treatment of 3-bromo-6-(2-hydroxyethyl)-2-methylbenzo[b]thiophene with n-butyl lithium in ether followed by carbon dioxide according to the method of Example 11(ii) gave 6-(2-hydroxyethyl)-2-methylbenzo[b]thiophene-3-carboxylic acid, m.p. 166°-169° C. (from toluene). | Cc1sc2cc(CCO)ccc2c1C(=O)O | null | null | null |
409,484 | ord_dataset-324fb6fdc2414cb79e436bf5d04d4bd2 | null | 1998-01-01T00:08:00 | true | [OH:1][C:2]1[CH:3]=[C:4]([O:15][S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])(=[O:18])=[O:17])[CH:5]=[CH:6][C:7]=1[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:26]([O:30][C:31]([N:33]1[CH2:38][CH2:37][CH:36]([CH2:39]O)[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27].CN1CCOCC1.C1(P(C2C=CC=C... | CC(C)(C)OC(=O)N1CCC(CO)CC1 | O=S(=O)(Oc1ccc(Cc2ccccc2)c(O)c1)c1ccccc1Cl | null | CCOC(=O)N=NC(=O)OCC | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN1CCOCC1 | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 1 | To 294 mg (0.787 mmol) of 2-chlorobenzenesulfonic acid 3-hydroxy-4-benzylphenyl ester, as prepared in the preceding step, in tetrahydrofuran (5 mL) containing 236 μL (1.10 mmol) of N-tert-butoxycarbonyl-4-piperidinemethanol, as prepared in step f of Example 1, 300 μL (2.72 mmol) of N-methylmorpholine, and 309 mg (1.18 ... | CC(C)(C)OC(=O)N1CCC(COc2cc(OS(=O)(=O)c3ccccc3Cl)ccc2Cc2ccccc2)CC1 | null | 84.8 | null |
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