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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
945,870 | ord_dataset-ed680843f6d14f5c9901869b2a06b4a4 | null | 2010-01-01T00:03:00 | true | [Br:1][C:2]1[C:3](=[O:10])[NH:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1.[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1COCC1>[CH2:11]([N:4]1[C:3](=[O:10])[C:2]([Br:1])=[CH:7][N:6]=[C:5]1[S:8][CH3:9])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1 | CSc1ncc(Br)c(=O)[nH]1 | BrCc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 8 | 5-bromo-2-(methylthio)pyrimidin-4(3H)-one (3.63 g, 16.4 mmol) was suspended in THF (80 ml) and CaH2 powder (1.29, 32.3 mmol) and benzyl bromide (2.6 ml, 22 mmol) were added. The reaction flask was fitted with a reflux condenser and placed in a preheated oil bath (65 C-70 C) and stirred overnight. After 15.5 hours, more... | CSc1ncc(Br)c(=O)n1Cc1ccccc1 | null | 12.6 | null |
612,684 | ord_dataset-5c4ee54447b84205a10f9c0473172972 | null | 2003-01-01T00:10:00 | true | [CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=O)[CH2:10]2)=[CH:5][CH:4]=1.[CH2:14]([N:21]1[CH2:26][CH2:25][CH:24]([NH2:27])[CH2:23][CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH2:14]([N:21]1[CH2:26][CH2:25][CH:24]([NH:27][CH:9]2[CH2:8][CH2:7][C:6... | COc1ccc2c(c1)CC(=O)CC2 | NC1CCN(Cc2ccccc2)CC1 | 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(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 25 | 24 | To a solution of 7-methoxy-3,4-dihydro-1H-naphthalen-2-one (10 g, 56.7 mmol) and 1-benzyl-piperidin-4-ylamine (12.7 mL, 62.4 mmol) in dichloroethane (50 mL) under a nitrogen atmosphere was added sodium triacetoxyborohydride (30 g, 141.8 mmol, 3.5 eq.) in a single portion. The reaction was stirred at room temperature fo... | COc1ccc2c(c1)CC(NC1CCN(Cc3ccccc3)CC1)CC2 | null | null | null |
934,074 | ord_dataset-d8a5dc784dde4465894ec7c69d2e3ba6 | null | 2010-01-01T00:01:00 | true | Br[C@H:2]1[C@H:7]([OH:8])[C:6]2[CH:9]=[C:10]([N+:17]([O-:19])=[O:18])[C:11]([O:13][CH2:14][O:15][CH3:16])=[CH:12][C:5]=2[O:4][C:3]1([CH3:21])[CH3:20].[OH-].[Na+].O>O1CCOCC1>[O:8]1[CH:7]2[CH:2]1[C:3]([CH3:21])([CH3:20])[O:4][C:5]1[CH:12]=[C:11]([O:13][CH2:14][O:15][CH3:16])[C:10]([N+:17]([O-:19])=[O:18])=[CH:9][C:6]=12 | COCOc1cc2c(cc1[N+](=O)[O-])[C@@H](O)[C@H](Br)C(C)(C)O2 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 2 | To a solution of (±)-trans-3-bromo-7-methoxymethoxy-2,2-dimethyl-6-nitro-3,4-dihydro-2H-1-benzopyran-4-ol (550 mg, 1.52 mmol) in dioxane (5.5 mL), 1 mol/L aqueous sodium hydroxide solution (1.82 mL, 1.82 mmol) was added at room temperature, and the resulting mixture was stirred for 2 hours. Upon the completion of the r... | COCOc1cc2c(cc1[N+](=O)[O-])C1OC1C(C)(C)O2 | null | 78 | null |
932,977 | ord_dataset-d8a5dc784dde4465894ec7c69d2e3ba6 | null | 2010-01-01T00:01:00 | true | [F:1][CH:2]([F:13])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][OH:12])=[CH:6][CH:5]=1.C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl>[F:1][CH:2]([F:13])[O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][O:12][S:22]([CH3:21])(=[O:24])=[O:23])=[CH:8][CH:9]=1 | OCCc1ccc(OC(F)F)cc1 | CS(=O)(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | ClCCl | null | null | null | null | null | null | null | null | null | 0 | 1.5 | A solution of 2-(4-difluoromethoxyphenyl)-ethanol (0.582 g, 3.09 mmol, from step (iii) above) in methylene chloride (8 mL) was cooled to 0° C. Triethylamine (0.52 mL, 3.7 mmol) was added followed by a solution of methanesulfonyl chloride (0.26 mL, 3.4 mmol) in methylene chloride (2 mL) and the reaction mixture was stir... | CS(=O)(=O)OCCc1ccc(OC(F)F)cc1 | null | 94.8 | null |
980,458 | ord_dataset-35b56288528641309a040cc2b6710b61 | null | 2010-01-01T00:08:00 | true | [C:1]([C:3]1[N:8]=[C:7]([CH2:9][CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[C:5]([CH3:18])[CH:4]=1)#[N:2].[Cl:19][C:20]1[CH:21]=[C:22]([SH:29])[C:23](=[CH:27][CH:28]=1)[C:24](O)=[O:25]>N1C=CC=CC=1>[Cl:19][C:20]1[CH:28]=[CH:27][C:23]2[C:24](=[O:25])[N:2]=[C:1]([C:3]3[N:8]=[C:7]([CH2:9][CH2:10]... | O=C(O)c1ccc(Cl)cc1S | Cc1cc(C#N)nc(CCC(=O)OC(C)(C)C)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | tert-Butyl 3-(6-cyano-4-methyl-2-pyridyl)propanoate (0.69 g, 2.8 mmol) and 4-chlorothiosalicylic acid (1.05 g, 5.7 mmol) were dissolved in pyridine (10 ml). The mixture was refluxed for 22 hrs. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with hex... | Cc1cc(CCC(=O)OC(C)(C)C)nc(-c2nc(=O)c3ccc(Cl)cc3s2)c1 | null | 28.3 | null |
1,323,188 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | [O:1]1[CH2:6][CH2:5][CH2:4][NH:3][C:2]1=[O:7].[H-].[Na+].Br[CH2:11][C:12]([O:14][CH3:15])=[O:13]>CN(C=O)C>[CH3:15][O:14][C:12](=[O:13])[CH2:11][N:3]1[CH2:4][CH2:5][CH2:6][O:1][C:2]1=[O:7] | O=C1NCCCO1 | COC(=O)CBr | 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 | null | 8 | A solution of 0.20 g (2.0 mmol) of 1,3-oxazinan-2-one from step A in 2 mL of anhydrous DMF was added to a 10 mL round bottom flask containing 0.13 g (3.2 mmol) of a 60% sodium hydride suspension in mineral oil under an atmosphere of nitrogen. After stirring for 10 min 0.37 g (2.4 mmol) of methyl brornoacetate was added... | COC(=O)CN1CCCOC1=O | null | 19.6 | null |
1,518,971 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][N:10]2[C:18]3[CH:17]=[CH:16][C:15]([C:19]([O:21]C)=[O:20])=[CH:14][C:13]=3[C:12]3[CH2:23][N:24]([CH3:27])[CH2:25][CH2:26][C:11]2=3)=[CH:4][CH:3]=1.[OH-].[K+]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][N:10]2[C:18]3[CH:17]=[CH:16][C:15]([C:19]([OH:21])=[O:20])=[CH:14][C:13]=3[... | COC(=O)c1ccc2c(c1)c1c(n2C#Cc2ccc(F)cc2)CCN(C)C1 | null | null | [K+] | [OH-] | 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 | 50 | null | Methyl 5-((4-fluorophenyl)ethynyl)-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-8-carboxylate (0.280 g) was dissolved in MeOH (10 mL) and added 10% aq. KOH solution (5 mL). The reaction mixture was heated at 50° C. for 48 h. Progress of the reaction was monitored by TLC and LCMS. The solvent was evaporated and th... | CN1CCc2c(c3cc(C(=O)O)ccc3n2C#Cc2ccc(F)cc2)C1 | null | null | null |
1,345,441 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | [Si]([O:8][CH2:9][CH2:10][N:11]([S:34]([CH3:37])(=[O:36])=[O:35])[C:12]1[C:13]([O:32][CH3:33])=[CH:14][C:15]2[C:19]([CH:20]=1)=[N:18][N:17]([C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)[C:16]=2[C:28]([NH:30][CH3:31])=[O:29])(C(C)(C)C)(C)C.[F-].[NH4+].O>CO>[F:27][C:24]1[CH:25]=[CH:26][C:21]([N:17]2[C:16]([C:28]... | CNC(=O)c1c2cc(OC)c(N(CCO[Si](C)(C)C(C)(C)C)S(C)(=O)=O)cc2nn1-c1ccc(F)cc1 | null | null | [F-] | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | O | null | null | null | null | null | null | null | null | null | 60 | null | To a stirred solution of Compound (11) (250 mg, 0.45 mmol) in MeOH (20 mL) was added ammonium fluoride (166 mg, 4.5 mmol) and water (5 mL). The reaction mixture was heated to 60° C. for 5 h (monitored by TLC and LCMS). MeOH was removed in vacuo and the residue was diluted with water. The resulting precipitate was filte... | CNC(=O)c1c2cc(OC)c(N(CCO)S(C)(=O)=O)cc2nn1-c1ccc(F)cc1 | null | 33.1 | null |
896,388 | ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded | null | 2009-01-01T00:08:00 | true | [Cl:1][C:2]1[N:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.Cl.[CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]=1[CH2:23][CH2:24][O:25][CH2:26][C:27]([NH2:29])=[NH:28].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>>[Cl:1][C:2]1[N:10]=[CH:9][C:8]([Cl:11])=[CH:7][... | O=C(O)c1cc(Cl)cnc1Cl | N=C(N)COCCc1ccc2ccccc2c1 | null | CN(C)C(On1nnc2ccccc21)=[N+](C)C | Cl | F[B-](F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | null | null | null | In analogy to the procedure described in example 78.3, 2,5-dichloronicotinic acid was reacted with 2-(2-naphthalen-2-yl-ethoxy)-acetamidine hydrochloride in the presence of TBTU and DIPEA to give 2,5-dichloro-N-[1-imino-2-(2-naphthalen-2-yl-ethoxy)-ethyl]-nicotinamide as yellow oil. MS: m/e=402.3 [M+H+]. | N=C(COCCc1ccc2ccccc2c1)NC(=O)c1cc(Cl)cnc1Cl | null | null | null |
12,100 | ord_dataset-7c810806c4564bada4a9550135bbb06f | null | 1976-01-01T00:08:00 | true | [OH-].[K+].[CH2:3]1[O:11][C:10]2[CH:9]=[CH:8][C:7]([OH:12])=[CH:6][C:5]=2[O:4]1.Cl[CH2:14][CH:15]=[C:16]([CH3:23])[CH2:17][CH2:18][O:19][CH:20]([CH3:22])[CH3:21]>COCCOC>[CH:20]([O:19][CH2:18][CH2:17][C:16]([CH3:23])=[CH:15][CH2:14][O:12][C:7]1[CH:8]=[CH:9][C:10]2[O:11][CH2:3][O:4][C:5]=2[CH:6]=1)([CH3:22])[CH3:21] | Oc1ccc2c(c1)OCO2 | CC(=CCCl)CCOC(C)C | null | [K+] | [OH-] | null | 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 | null | 18 | 1.7 g (0.03 mol) of pulverised potassium hydroxide are added to a solution of 4.1 g (0.03 mol) of 3,4-methylendioxy-phenol and 6.2 g (0.035 mol) of 1-chloro-5-isopropoxy-3-methyl-2-pentene in 100 cc of 1,2-dimethoxyethane. The mixture is stirred at 60° for a period of 18 hours, is subsequently filtered and evaporated a... | CC(=CCOc1ccc2c(c1)OCO2)CCOC(C)C | null | null | null |
285,343 | ord_dataset-d63ab258f4634f87bdebbaff0a341c28 | null | 1994-01-01T00:02:00 | true | [C:1]1([CH:9]=O)[CH:6]=[CH:5][C:4]([CH:7]=O)=[CH:3][CH:2]=1.[CH3:11][C:12](=[O:17])[CH2:13][C:14](=[O:16])[CH3:15].S(Cl)(Cl)=O>CC(O)C>[C:14]([C:13]([C:12](=[O:17])[CH3:11])=[CH:9][C:1]1[CH:2]=[CH:3][C:4]([CH:7]=[C:13]([C:12](=[O:17])[CH3:11])[C:14](=[O:16])[CH3:15])=[CH:5][CH:6]=1)(=[O:16])[CH3:15] | O=Cc1ccc(C=O)cc1 | CC(=O)CC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=S(Cl)Cl | CC(C)O | null | null | null | null | null | null | null | null | null | null | null | To a mixture containing 1.34 g of 1,4-benzenedicarboxaldehyde and 2.1 g of 2,4-pentanedione in 20ml of 2-propanol was gradually added 3.0 g of thionyl chloride with stirring and cooling below 20° C. The mixture was stirred over night at room temperature, filtered and washed with 2-propanol. Yield 1.1 g (55%). | CC(=O)C(=Cc1ccc(C=C(C(C)=O)C(C)=O)cc1)C(C)=O | null | null | null |
905,187 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | [F:1][C:2]([F:18])([F:17])[C:3]([NH:5][C:6]1[CH:7]=[CH:8][C:9]2[O:14][CH2:13][C:12](=[O:15])[NH:11][C:10]=2[CH:16]=1)=[O:4].[Cl:19]N1C(=O)CCC1=O>CN(C=O)C>[Cl:19][C:8]1[C:9]2[O:14][CH2:13][C:12](=[O:15])[NH:11][C:10]=2[CH:16]=[C:6]([NH:5][C:3](=[O:4])[C:2]([F:1])([F:17])[F:18])[CH:7]=1 | O=C1COc2ccc(NC(=O)C(F)(F)F)cc2N1 | O=C1CCC(=O)N1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | null | 2,2,2-Trifluoro-N-(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)acetamide was treated with N-chlorosuccinimide in DMF to obtain N-(8-chloro-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)-2,2,2-trifluoroacetamide. | O=C1COc2c(Cl)cc(NC(=O)C(F)(F)F)cc2N1 | null | null | null |
1,768,348 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | [CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH3:14])([CH3:13])[C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1)=[CH2:2]>C(O)C.[C].[Pd]>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH3:13])([CH3:14])[C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1)[CH3:2] | C=Cc1ccc(C(C)(C)C(=O)O)cc1 | 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 | null | 2-(4-Vinylphenyl)-2-methylpropanoic acid (58 g) was dissolved in ethanol, and then stirred for 3 hrs under atmospheric hydrogen pressure in the presence of 10% palladium carbon (5.8 g). The catalyst was removed by filtration, and the filtrate was concentrated to obtain a crude product, which was then suspended and wash... | CCc1ccc(C(C)(C)C(=O)O)cc1 | null | 96.4 | null |
1,442,354 | ord_dataset-275a3da8f45f4536ad29727f0ef9ba66 | null | 2014-01-01T00:06:00 | true | [CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([NH2:11])=[N:8][C:7]=1[CH2:12][CH2:13][CH3:14])=[O:5])[CH3:2].[O:15]1[C:19]2[CH:20]=[CH:21][C:22]([C:24]3([C:27](O)=[O:28])[CH2:26][CH2:25]3)=[CH:23][C:18]=2[O:17][CH2:16]1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>C(#N)C>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:... | O=C(O)C1(c2ccc3c(c2)OCO3)CC1 | CCCc1nc(N)sc1C(=O)OCC | null | CN(C)C(On1nnc2cccnc21)=[N+](C)C | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 65 | 4 | 2-Amino-4-propyl-thiazole-5-carboxylic acid ethyl ester (0.50 g, 2.3 mmol) and 1-benzo[1,3]dioxol-5-yl-cyclopropanecarboxylic acid (0.48 g, 2.3 mmol) were dissolved in acetonitrile (15 mL) containing triethylamine (0.66 mL, 4.7 mmol). O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU, 0.... | CCCc1nc(NC(=O)C2(c3ccc4c(c3)OCO4)CC2)sc1C(=O)OCC | null | 60.9 | null |
1,174,931 | ord_dataset-0f9d2dbe929a45c3892ae75e81e99443 | null | 2012-01-01T00:06:00 | true | [CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[C:15](Cl)[N:14]=[C:13]([O:18][CH3:19])[N:12]=2)[CH2:7][CH2:6]1)=[O:4].[Cl:20][C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1[CH2:28][CH2:29][NH2:30].C(=O)(O)[O-].[Na+].CN1CCCC1=O>O>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[C:15]([NH... | COC(=O)C1CCN(c2cc(Cl)nc(OC)n2)CC1 | NCCc1ccc(Cl)cc1Cl | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN1CCCC1=O | O | null | null | null | null | null | null | null | null | null | 140 | 12 | In a tube is combined 1-(6-chloro-2-methoxy-pyrimidin-4-yl)-piperidine-4-carboxylic acid methyl ester [103 mg, 0.36 mmol], 2-(2,4-dichloro-phenyl)-ethylamine (0.163 mL, 1.08 mmol), sodium bicarbonate (181 mg, 2.16 mmol) and N-methylpyrrolidinone (2 mL). The mixture is heated at 140° C. for 12 h. Additional 2-(2,4-dichl... | COC(=O)C1CCN(c2cc(NCCc3ccc(Cl)cc3Cl)nc(OC)n2)CC1 | null | 44.3 | null |
833,335 | ord_dataset-ec576c604a9d47258c87c732a043ec71 | null | 2008-01-01T00:08:00 | true | [CH3:1][O:2][C:3](=[O:31])[CH:4]([C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]2[CH:28]=[CH:27][C:26]([CH:29]=O)=[CH:25][CH:24]=2)=[CH:18][CH:17]=1)[CH2:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[C:8]([O:14][CH3:15])[CH:7]=1.[S:32]1[CH2:36][C:35](=[O:37])[NH:34][C:33]1=[O:38].C(O)(=O)C1C=CC=CC=1.N1CCCCC1>C1(C)C=CC=CC=1>[... | O=C1CSC(=O)N1 | COC(=O)C(Cc1cc(OC)cc(OC)c1)c1ccc(Oc2ccc(C=O)cc2)cc1 | null | O=C(O)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCNCC1 | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | To a stirred suspension of 16 (1.81 g, 4.3 mmol) in anhydrous toluene (25 mL), 2,4-thiazolidinedione (0.56 g, 4.74 mmol), benzoic acid (0.68 g, 5.60 mmol) and piperidine (0.60 mL, 6.03 mmol) was added sequentially and heated at reflux temperature with continuous removal of water using a Dean-Stark apparatus for 2 h. So... | COC(=O)C(Cc1cc(OC)cc(OC)c1)c1ccc(Oc2ccc(C=C3SC(=O)NC3=O)cc2)cc1 | null | 81.5 | null |
986,079 | ord_dataset-35b56288528641309a040cc2b6710b61 | null | 2010-01-01T00:08:00 | true | Cl[C:2]1[N:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[NH3:13]>CC(C)=O.CO>[NH2:13][C:2]1[N:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5] | COC(=O)c1ccc(Cl)nc1Cl | N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | CO | null | null | null | null | null | null | null | null | null | 25 | 216 | Performed in duplicate on identical scales in two pressure vessels, methyl 2,6-dichloronicotinate (4.5 g, 22 mmol) was dissolved in NH3 solution (250 mL, 0.5 M in 1,4-dioxane; 0.125 mol). The pressure vessels were sealed and heated at (85±5) ° C. for 9 days. The two reaction mixtures were allowed to cool to 25° C., the... | COC(=O)c1ccc(Cl)nc1N | null | 148.1 | null |
431,607 | ord_dataset-8cbb58558c904b2b85fa7a1b084a0de9 | null | 1999-01-01T00:06:00 | true | [CH3:1][C:2]1[CH:21]=[CH:20][C:5]([NH:6][CH:7]([C:10]2[CH:15]=[CH:14][C:13]([S:16](=[O:19])(=[O:18])[NH2:17])=[CH:12][CH:11]=2)[C:8]#N)=[CH:4][CH:3]=1.[CH:22]([CH:24]=C)=O>>[CH3:1][C:2]1[CH:21]=[CH:20][C:5]([N:6]2[CH:24]=[CH:22][CH:8]=[C:7]2[C:10]2[CH:15]=[CH:14][C:13]([S:16](=[O:19])(=[O:18])[NH2:17])=[CH:12][CH:11]=2... | Cc1ccc(NC(C#N)c2ccc(S(N)(=O)=O)cc2)cc1 | C=CC=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 | Following a procedure similar to that described in Example 1(iii), but using α-(4-methylanilino)-α-(4-sulfamoylphenyl)acetonitrile [prepared as described in step (ii) above] and acrolein as starting materials, the title compound was obtained as a pale brown powder (yield 28%), melting at 131-134° C. | Cc1ccc(-n2cccc2-c2ccc(S(N)(=O)=O)cc2)cc1 | null | null | null |
937,159 | ord_dataset-90b0aa1f83334a02919b2be3a1c04542 | null | 2010-01-01T00:02:00 | true | [C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:17]I>CN(C=O)C>[C:1]([O:5][C:6](=[O:16])[N:7]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([Br:15])=[CH:13][CH:14]=1)[CH3:17])([CH3:4])([CH3:2])[CH3:3] | CC(C)(C)OC(=O)NCc1ccc(Br)cc1 | CI | 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 | 50 | 18 | In a 60-mL vial, tert-butyl-4-bromobenzylcarbamate (1.25 g, 4.37 mmol) was dissolved in DMF (12 mL). To this solution was added Ag2O (4.0 g, 17 mmol) followed by the addition of CH3I (0.68 mL, 11 mmol). The mixture was stirred at 50° C. for 18 hours. The reaction mixture was filtered through a bed of celite and the cel... | CN(Cc1ccc(Br)cc1)C(=O)OC(C)(C)C | null | 99.1 | null |
1,537,061 | ord_dataset-8d5c200bca27407ab9febe7598e16458 | null | 2015-01-01T00:01:00 | true | COC1C=CC(C[N:8]2[C:26](=[O:27])[N:25]3[CH:21]([CH2:22][CH:23]([O:28][C:29]4[CH:34]=[C:33]([O:35][CH3:36])[N:32]=[C:31]([C:37]5[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=5)[N:30]=4)[CH2:24]3)[C:20](=[O:43])[NH:19][C:18]3([C:44]([NH:46][S:47]([CH:50]4[CH2:52][CH2:51]4)(=[O:49])=[O:48])=[O:45])[CH:16]([CH2:17]3)[CH:15]=[CH:14]... | COc1ccc(CN2CCCCCC=CC3CC3(C(=O)NS(=O)(=O)C3CC3)NC(=O)C3CC(Oc4cc(OC)nc(-c5ccccc5)n4)CN3C2=O)cc1 | null | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | Compound 6g was dissolved in a 1:2 mixture of TFA:DCM (24 ml) and stirred at RT for 1 h. NaHCO3 was added and the organic layer was separated of, dried, filtered and evaporated. The residue was purified by preparative HPLC which gave the pure title compound (19 mg, 8% over two steps), MS (M+H)+639. | COc1cc(OC2CC3C(=O)NC4(C(=O)NS(=O)(=O)C5CC5)CC4C=CCCCCCNC(=O)N3C2)nc(-c2ccccc2)n1 | null | 8 | null |
470,415 | ord_dataset-f1b9e9741a6a4cc68e7070df811f86bb | null | 2000-01-01T00:07:00 | true | [H-].C([Al+]CC(C)C)C(C)C.C[O:12][C:13](=O)[C:14]1[CH:19]=[C:18]([CH:20]([CH3:22])[CH3:21])[C:17]([O:23][S:24](=[O:45])(=[O:44])[NH:25][C:26](=[O:43])[CH2:27][C:28]2[C:33]([CH:34]([CH3:36])[CH3:35])=[CH:32][C:31]([CH:37]([CH3:39])[CH3:38])=[CH:30][C:29]=2[CH:40]([CH3:42])[CH3:41])=[C:16]([CH:46]([CH3:48])[CH3:47])[CH:15... | COC(=O)c1cc(C(C)C)c(OS(=O)(=O)NC(=O)Cc2c(C(C)C)cc(C(C)C)cc2C(C)C)c(C(C)C)c1 | null | null | CC(C)C[Al+]CC(C)C | [H-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 3 | 3.9 mL of a 1 M solution of diisobutyl aluminum hydride in dichloromethane was added to a solution of 3,5-Diisopropyl-4-{[(2,4,6-triisopropyl-phenyl)-acetyl]sulfamoyloxy}-benzoic acid methyl ester (1.0 g, 1.8 mmol) in 125 mL dichloromethane at -78° C. After 3 hours, the reaction was warmed to room temperature and then ... | CC(C)c1cc(C(C)C)c(CC(=O)NS(=O)(=O)Oc2c(C(C)C)cc(CO)cc2C(C)C)c(C(C)C)c1 | null | 30.3 | null |
653,824 | ord_dataset-fe016e2f90e741a590ad77fd5933161f | null | 2004-01-01T00:11:00 | true | [F:1][C:2]([F:26])([F:25])[CH2:3][NH:4][C:5]([C:7]1([CH2:20][CH2:21][CH2:22][CH2:23]Br)[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)=[O:6].[F:27][C:28]1[CH:29]=[CH:30][C:31]2[N:35]=[C:34]([N:36]3[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]3)[N:33]([CH3:42])[C:32]=2[CH:43]=1>>[F:1... | Cn1c(N2CCNCC2)nc2ccc(F)cc21 | O=C(NCC(F)(F)F)C1(CCCCBr)c2ccccc2-c2ccccc21 | null | null | null | null | null | null | null | 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 1e from 9-(4-bromo-butyl)-9H-fluorene-9-carboxylic acid-(2,2,2-trifluoro-ethyl)-amide and 6-fluoro-1-methyl-2-piperazin-1-yl-1H-benzimidazole | Cn1c(N2CCN(CCCCC3(C(=O)NCC(F)(F)F)c4ccccc4-c4ccccc43)CC2)nc2ccc(F)cc21 | null | null | null |
1,008,538 | ord_dataset-7448b89163bf426c9d9777809ce24cec | null | 2010-01-01T00:11:00 | true | [C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[C:7]([O:15]C)[C:6]=1[C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)=O.CC(C)=O.B(Br)(Br)Br>C(Cl)Cl>[C:11]([C:9]1[CH:8]=[C:7]([OH:15])[C:6]([C:17]2[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=2)=[C:5]([C:1]([CH3:4... | COc1cc(C(C)(C)C)cc(C(C)(C)C)c1-c1ccc(Cl)cc1 | null | null | BrB(Br)Br | O=C=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | ClCCl | null | null | null | null | null | null | null | null | null | 0 | null | A solution of 4.9 g (14.8 mmol) of the product of Step A in 30 mL of CH2Cl2 was placed in an external cooling bath containing dry ice and acetone and stirred under a nitrogen atmosphere. A 1.0 M solution of boron tribromide (20 mL, 20.0 mmol) in CH2Cl2 was added dropwise. After the addition was complete, the reaction m... | CC(C)(C)c1cc(O)c(-c2ccc(Cl)cc2)c(C(C)(C)C)c1 | null | null | null |
1,468,145 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | CC[O-].[Na+].O=[C:6]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[C:14]([O:16]CC)=O.[NH2:19][C:20]([NH2:22])=[S:21].Cl>CCO>[SH:21][C:20]1[N:19]=[C:14]([OH:16])[C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:6]=2[N:22]=1 | NC(N)=S | CCOC(=O)C1CCCCCCC1=O | null | CC[O-] | Cl | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | 700 mg of NaOEt (10 mmol; 1.0 equiv) was added to 6 mL of abs. EtOH. To this solution was added, with stirring, 2 g of ethyl 2-keto-cyclooctylcarboxylate (10 mmol; 1.0 equiv) and 1 g of thiourea (13 mmol; 1.3 equiv). The mixture was refluxed for 6 hours. After cooling, the mixture was poured onto ice and acidified with... | Oc1nc(S)nc2c1CCCCCC2 | null | 63.2 | null |
818,815 | ord_dataset-50f99930fc41474db226bc80774b38df | null | 2008-01-01T00:04:00 | true | C[O:2][C:3]([C:5]1[N:6]([CH3:15])[N:7]=[C:8]2[C:13]=1[CH:12]=[CH:11][CH:10]=[C:9]2[Br:14])=[O:4].[OH-].[Na+]>C(O)C>[Br:14][C:9]1[C:8]2[C:13](=[C:5]([C:3]([OH:4])=[O:2])[N:6]([CH3:15])[N:7]=2)[CH:12]=[CH:11][CH:10]=1 | COC(=O)c1c2cccc(Br)c2nn1C | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 55 | 8 | A mixture of 7-bromo-2-methyl-2H-indazole-3-carboxylic acid methyl ester (35a; 0.215 g, 0.799 mmol), 8 mL of a 2 M aqueous NaOH solution, and 6 mL of ethanol was stirred at 55° C. overnight, then concentrated to remove ethanol. The remaining aqueous layer was acidified with a 10% aqueous HCl solution and extracted with... | Cn1nc2c(Br)cccc2c1C(=O)O | null | 94.7 | null |
1,690,812 | ord_dataset-c1e70ad912eb438f8d34b1dc681f809a | null | 2016-01-01T00:02:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]([OH:14])=[O:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:15](Cl)Cl.C[Si](C=[N+]=[N-])(C)C.CCOCC>CO>[N:8]1([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH:10]([C:12]([O:14][CH3:15])=[O:13])[CH2:11]1 | CC(C)(C)OC(=O)N1CC(C(=O)O)C1 | ClCCl | null | C[Si](C)(C)C=[N+]=[N-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | CO | null | null | null | null | null | null | null | null | null | 0 | 0.17 | 1-(t-butoxycarbonyl)azetidine-3-carboxylic acid (2.03 g, 10.09 mmol) was dissolved in MeOH (10 ml) and DCM (10 mL) and then cooled to 0° C. A 2M solution of trimethylsilyldiazomethane in ether (7.57 ml, 15.1 mmol) was then added drop-wise over 5 minutes. The solution was stirred for 10 minutes at 0° C. and then warmed ... | COC(=O)C1CN(C(=O)OC(C)(C)C)C1 | null | null | null |
1,620,011 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [Na].[CH2:2]([C:9]#[N:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:11][C:12]([CH3:16])=[CH:13][CH:14]=O>CO>[CH3:11][C:12]([CH3:16])=[CH:13][CH:14]=[C:2]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[C:9]#[N:10] | N#CCc1ccccc1 | CC(C)=CC=O | null | [Na] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 20 | Sodium (9.2 g, 0.4 mol) is dissolved in methanol (130 ml) and benzylcyanide (46.8 g, 0.40 mol) is added, followed by the careful addition of a solution of 3-methyl-2-butenal (40.3 g, 0.48) in methanol (100 ml). The resulting suspension is stirred for 20 h at room temperature and then worked up following the procedure d... | CC(C)=CC=C(C#N)c1ccccc1 | null | 61.3 | null |
1,502,879 | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | null | 2014-01-01T00:11:00 | true | Cl.Cl.[F:3][C:4]1[C:12]2[O:11][CH:10]=[CH:9][C:8]=2[C:7]([CH:13]2[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C@H:21]3[CH2:26][CH2:25][C@H:24]([NH2:27])[CH2:23][CH2:22]3)[CH2:15][CH2:14]2)=[CH:6][CH:5]=1.[O:28]1[CH2:33][CH2:32][CH:31]([C:34](O)=[O:35])[CH2:30][CH2:29]1>>[F:3][C:4]1[C:12]2[O:11][CH:10]=[CH:9][C:8]=2[C:7]([CH... | N[C@H]1CC[C@H](CCN2CCC(c3ccc(F)c4occc34)CC2)CC1 | O=C(O)C1CCOCC1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound, off-white solid (87 mg, 76%), MS (ISP) m/z=457.4 [(M+H)+], mp 208° C., was prepared in accordance with the general method of example 1 from trans-4-{2-[4-(7-fluoro-benzofuran-4-yl)-piperidin-1-yl]-ethyl}-cyclohexylamine dihydrochloride (intermediate C) (104 mg, 0.25 mmol) and tetrahydropyran-4-yl-ca... | O=C(N[C@H]1CC[C@H](CCN2CCC(c3ccc(F)c4occc34)CC2)CC1)C1CCOCC1 | null | null | null |
768,003 | ord_dataset-8214eb8444a44dc2900ccb42dbeff15e | null | 2007-01-01T00:05:00 | true | [F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:11]=[C:12]([CH2:27]OS(C)(=O)=O)[C:13](=[O:26])[N:14]([CH2:16][CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[N:15]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[N:33]1([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1>>[C:42]... | COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CCCc3ccc(F)cc3)n2)cc1F | CC(C)(C)OC(=O)N1CCNCC1 | null | null | null | null | null | null | null | 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 1(10), 6-(3-fluoro-4-methoxyphenyl)-2-[3-(4-fluorophenyl)propyl]-4-methanesulfonyloxymethyl-2H-pyridazin-3-one and tert-butyl 1-piperazinecarboxylate were reacted to yield the title compound as a yellow oil (yield: 72.6%). | COc1ccc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(CCCc3ccc(F)cc3)n2)cc1F | null | 72.6 | null |
1,678,365 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | [O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:11]([O:13]C)=O)[CH:8]=2)[NH:3]1.O.[NH2:16][NH2:17]>CCO>[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:11]([NH:16][NH2:17])=[O:13])[CH:8]=2)[NH:3]1 | COC(=O)c1ccc2c(c1)CC(=O)N2 | NN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | 80 | 6 | To a solution of methyl 2-oxoindoline-5-carboxylate (0.40 g, 4.8 mmol) in EtOH (8 ml) was added hydrazine monohydrate (2 ml), and the mixture was stirred for 6 h at 80° C. The mixture was cooled to room temperature, and the resulting precipitate was filtered and dried to afford 2-oxoindoline-5-carbohydrazide (0.25 g, 6... | NNC(=O)c1ccc2c(c1)CC(=O)N2 | null | 63 | null |
1,626,151 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | O1[C:5]2([CH2:10][CH2:9][CH:8]([N:11]3[C:16](=[O:17])[C:15]([CH2:18][C:19]4[CH:24]=[CH:23][C:22]([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=5[C:31]5[NH:35][C:34](=[O:36])[O:33][N:32]=5)=[CH:21][CH:20]=4)=[C:14]([CH2:37][CH2:38][CH3:39])[N:13]4[N:40]=[C:41]([CH3:43])[N:42]=[C:12]34)[CH2:7][CH2:6]2)[O:4]CC1.Cl>O1CCCC1>[... | CCCc1c(Cc2ccc(-c3ccccc3-c3noc(=O)[nH]3)cc2)c(=O)n(C2CCC3(CC2)OCCO3)c2nc(C)nn12 | 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 | 70 | 22 | A mixture of 4-(1,4-dioxaspiro[4.5]dec-8-yl)-2-methyl-6-{[2′-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-7-propyl[1,2,4]triazolo[1,5-a]pyrimidin-5(4H)-one (0.76 g), 6M hydrochloric acid (3 mL) and tetrahydrofuran (4 mL) was stirred at 70° C. for 22 hr. The reaction mixture was extracted with ethyl ace... | CCCc1c(Cc2ccc(-c3ccccc3-c3noc(=O)[nH]3)cc2)c(=O)n(C2CCC(=O)CC2)c2nc(C)nn12 | null | 44.1 | null |
1,544,147 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].[C:10](#[N:12])[CH3:11].Cl[Sn](Cl)(Cl)Cl>ClCCCl>[NH2:12][C:10](=[C:2]([C:1]([O:8][CH3:9])=[O:7])[C:3]([O:5][CH3:6])=[O:4])[CH3:11] | COC(=O)CC(=O)OC | CC#N | null | Cl[Sn](Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCCl | null | null | null | null | null | null | null | null | null | null | null | null | To a stirred solution containing 4.36 mL (38.0 mmol) of dimethyl malonate and 2.00 mL (38.0 mmol) of acetonitrile in 20 mL of 1,2-dichloroethane were added 8.90 mL (76.0 mmol) of SnCl4. The reaction mixture was stirred at reflux for 2 h. The reaction mixture was then concentrated under diminished pressure and the resid... | COC(=O)C(C(=O)OC)=C(C)N | null | null | null |
900,483 | ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded | null | 2009-01-01T00:08:00 | true | [OH:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[C:13]([C:18]([F:21])([F:20])[F:19])[CH:14]=[CH:15][CH:16]=3)[N:11]=[CH:10][C:9]=2[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:23])[CH:5]=[CH:6][CH:7]=1.Br[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([CH3:38])[CH:33]=1>>[CH3:31][C:32]1[CH:33]=[C:34]([CH:35]=[CH... | O=C(c1ccccc1)c1cnc2c(C(F)(F)F)cccc2c1-c1cccc(O)c1 | Cc1cccc(CBr)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from [4-(3-hydroxyphenyl)-8-(trifluoromethyl)quinolin-3-yl](phenyl)methanone and 1-Bromomethyl-3-methylbenzene following the procedure of Example 478: MS (ESI) m/z 498. | Cc1cccc(COc2cccc(-c3c(C(=O)c4ccccc4)cnc4c(C(F)(F)F)cccc34)c2)c1 | null | null | null |
1,170,549 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | FC(F)(F)S([O-])(=O)=O.C[N+]1[CH:14]=[CH:13][N:12]([S:15]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)(=[O:17])=[O:16])C=1.[C@H:24]1([NH:33][C:34]2[CH:43]=[CH:42][C:41]3[C:36](=[CH:37][CH:38]=C(N)C=3)[N:35]=2)[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:26][CH2:25]1>C(#N)C>[C@H:24]1([NH:33][C:34]2[CH:43]=[CH:4... | C[n+]1ccn(S(=O)(=O)N2CCOCC2)c1 | Nc1ccc2nc(N[C@@H]3CCc4ccccc43)ccc2c1 | null | O=S(=O)([O-])C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | 80 | 16 | 1-Methyl-3-(morpholine-4-sulfonyl)-3H-imidazol-1-ium trifluoromethanesulfonate (0.139 g, 0.36 mmol) and (R)—N2-indan-1-yl-quinoline-2,6-diamine (0.10 g, 0.36 mmol) were dissolved in acetonitrile (2 mL) and stirred for 16 h at 80° C. The solvent was removed and the residue subjected to column chromatography (silica gel,... | O=S(=O)(Nc1ccc2nc(N[C@@H]3CCc4ccccc43)ccc2c1)N1CCOCC1 | null | 45.8 | null |
1,183,910 | ord_dataset-9cd817a75dfc4fe7ad19d4232772d5ff | null | 2012-01-01T00:07:00 | true | C(O[C:6](=[O:21])[N:7]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[N:8]1[CH:12]=[CH:11][CH:10]=[CH:9]1)(C)(C)C.[CH2:22]([O:24][C:25](=[O:37])[CH:26](C(OCC)=O)[C:27](OCC)=[O:28])[CH3:23]>>[CH2:22]([O:24][C:25]([C:26]1[C:6](=[O:21])[N:7]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=2)[N:... | CC(C)(C)OC(=O)N(Cc1ccc(F)cc1)n1cccc1 | CCOC(=O)C(C(=O)OCC)C(=O)OCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared according to the thermal cyclization condition used in Example 1 step c) from (4-fluoro-benzyl)-pyrrol-1-yl-carbamic acid tert-butyl ester (1.0 eq.) and 2-ethoxycarbonyl-malonic acid diethyl ester (2.0 eq.). ESI (m/z): 331 (M+H)+. | CCOC(=O)c1c(O)c2cccn2n(Cc2ccc(F)cc2)c1=O | null | null | null |
26,236 | ord_dataset-2ada3fda46fc44719ba0c8001f53c1b3 | null | 1977-01-01T00:06:00 | true | [C:1]([C:5]1[CH:14]=[CH:13][C:12]2[CH2:11][CH2:10][CH2:9][CH:8]([C:15]([NH2:17])=O)[C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:19]>>[C:1]([C:5]1[CH:14]=[CH:13][C:12]2[CH2:11][CH2:10][CH2:9][CH:8]([C:15](=[S:19])[NH2:17])[C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2] | S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3 | CC(C)(C)c1ccc2c(n1)C(C(N)=O)CCC2 | null | null | null | null | null | null | null | 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 2-t-butyl-5,6,7,8-tetrahydroquinoline-8-carboxamide (4 g.) and P2S5 (3 g.) as described in Example 8 and was isolated as creamy needles after recrystallisation from n-hexane m.p. 126° C (650 mgs.). Found: C, 68.18; H, 8.25; N, 11.14%. C14H20N2S requires C,67.70; H, 8.12; N, 11.23%. | CC(C)(C)c1ccc2c(n1)C(C(N)=S)CCC2 | null | null | null |
779,376 | ord_dataset-8034115bd2ec4d3e95bd3ff7cfde0bde | null | 2007-01-01T00:07:00 | true | [CH:1]1([C:4]2[N:9]3[N:10]=[CH:11][C:12]([C:13]#[CH:14])=[C:8]3[N:7]=[C:6]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=3)[CH:5]=2)[CH2:3][CH2:2]1.Br[C:24]1[CH:29]=[CH:28][C:27]([S:30]([NH2:33])(=[O:32])=[O:31])=[CH:26][CH:25]=1>>[CH:1]1([C:4]2[N:9]3[N:10]=[CH:11][C:12]([C:13]#[C:14][C:25]4[CH:26]=[C:27... | C#Cc1cnn2c(C3CC3)cc(-c3ccc(Cl)c(Cl)c3)nc12 | NS(=O)(=O)c1ccc(Br)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from 7-cyclopropyl-5-(3,4-dichloro-phenyl)-3-ethynyl-pyrazolo[1,5-a]pyrimidine (example C.8) (82 mg, 0.25 mmol) and 4-bromo-benzenesulfonamide (59 mg, 0.25 mmol) according to general procedure II. Obtained as a yellow solid (37 mg, 30%). MS (ISP) 483.5 [(M+H)+]; mp 200–202° C. | NS(=O)(=O)c1cccc(C#Cc2cnn3c(C4CC4)cc(-c4ccc(Cl)c(Cl)c4)nc23)c1 | null | null | null |
1,315,441 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | [N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]([F:17])([F:16])[CH:13]([F:15])[F:14])=[CH:6][CH:5]=1)([O-])=O>C(O)(=O)C.[Fe]>[F:16][C:12]([F:17])([CH:13]([F:14])[F:15])[CH2:11][O:10][C:7]1[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=1 | O=[N+]([O-])c1ccc(OCC(F)(F)C(F)F)cc1 | null | null | [Fe] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | 55 | null | Iron powder (1.3 g, 23.2 mol) was added to a solution of 1-nitro-4-(2,2,3,3-tetrafluoro-propoxy)-benzene (600 mg, 2.4 mmol) in acetic acid (4 ml) and heated at 50-60° C. for 1 hr. The reaction mixture was filtered hot over celite and washed with ethyl acetate. The filtrate was washed with water, 5% sodium hydroxide sol... | Nc1ccc(OCC(F)(F)C(F)F)cc1 | null | 56 | null |
562,900 | ord_dataset-7c28974b7fcf4c9c86d5f2a42ba328a2 | null | 2002-01-01T00:09:00 | true | C(OC([NH:8][C:9]1[CH:28]=[C:27]([F:29])[C:26]([F:30])=[CH:25][C:10]=1[C:11]([NH:13][CH2:14][C:15]([NH:17][CH2:18][CH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)=[O:16])=[O:12])=O)(C)(C)C.[CH3:31][C:32]1[CH:39]=[CH:38][C:35]([CH:36]=O)=[CH:34][C:33]=1[N+:40]([O-:42])=[O:41].C(O)(=O)C.[BH3-]C#N.[Na+]>CO>[NH2:8][C:9]1[C... | CC(C)(C)OC(=O)Nc1cc(F)c(F)cc1C(=O)NCC(=O)NCC1CCNCC1 | Cc1ccc(C=O)cc1[N+](=O)[O-] | null | [BH3-]C#N | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | CO | null | null | null | null | null | null | null | null | null | 50 | 8 | To a mixture of 4-[{N-(2-(tert-butoxycarbonylamino)-4,5-difluorobenzoyl)glycyl}aminomethyl]piperidine (0.050 mmol), 4-methyl-3-nitrobenzaldehyde (0.25 mmol), methanol (1.2 mL), and acetic acid (0.050 mL) was added NaBH3CN (0.50 mmol) in methanol (1.0 mL). The reaction mixture was stirred at 50° C. overnight. The mixtur... | Cc1ccc(CN2CCC(CNC(=O)CNC(=O)c3cc(F)c(F)cc3N)CC2)cc1[N+](=O)[O-] | null | null | null |
1,104,264 | ord_dataset-375a420ee9b042918ddca20f02df37d3 | null | 2011-01-01T00:11:00 | true | [NH2:1][CH2:2][CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][C:11]([C:13]([N:15]3[CH:20]4[CH2:21][CH2:22][CH:16]3[CH2:17][CH:18]([OH:23])[CH2:19]4)=[O:14])=[CH:12][C:7]=2[N:6]=[CH:5]1.CCN(C(C)C)C(C)C.[O:33]=[S:34]1(=[O:43])[CH2:39][CH2:38][N:37]([C:40](Cl)=[O:41])[CH2:36][CH2:35]1>C1COCC1>[OH:23][CH:18]1[CH2:19][CH:20]2[N:15]([C:13... | O=C(Cl)N1CCS(=O)(=O)CC1 | NCCn1cnc2cc(C(=O)N3C4CCC3CC(O)C4)ccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 2 | To a solution of [1-(2-aminoethyl)-1H-benzimidazol-5-yl]-(3-hydroxy-8-azabicyclo[3.2.1]oct-8-yl)-methanone (0.2 g, 0.636 mmol) in dry THF (5 mL) was added DIPEA (0.3 mL, 1.91 mmol) at 0° C. To this reaction mixture was added 1,1-dioxo-thiomorpholine-4-carbonyl chloride slowly and stirred for 2 h at ambient temperature.... | O=C(NCCn1cnc2cc(C(=O)N3C4CCC3CC(O)C4)ccc21)N1CCS(=O)(=O)CC1 | null | 2.3 | null |
1,140,882 | ord_dataset-68715347640045adb1b09e6a04722b0e | null | 2012-01-01T00:03:00 | true | [Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(=O)([O-])[O-].[K+].[K+].[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25](OS(C)(=O)=O)[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16]>CN(C=O)C.O>[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([O:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Br:1])[CH2:24][CH... | CC(C)(C)OC(=O)N1CCC(OS(C)(=O)=O)CC1 | Oc1ccccc1Br | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O | null | null | null | null | null | null | null | null | null | 80 | null | To a stirred solution of 2-bromophenol (0.5 g, 0.00289 mole) in DMF (4 mL) was added potassium carbonate (0.478 g, 0.003468 mole), followed by 4-methanesulfonyloxy-piperidine-1-carboxylic acid tert-butyl ester (0.888 g, 0.00318 mole). The reaction mixture was heated at 80° C. for 6 hours. The mixture was then diluted w... | CC(C)(C)OC(=O)N1CCC(Oc2ccccc2Br)CC1 | null | 62.2 | null |
1,628,093 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [CH2:1]([NH2:3])[CH3:2].Cl[SiH:5]1[N:9]([CH:10]([CH3:12])[CH3:11])[CH:8]=[CH:7][N:6]1[CH:13]([CH3:15])[CH3:14]>CCCCCC>[CH2:1]([NH:3][SiH:5]1[N:9]([CH:10]([CH3:11])[CH3:12])[CH:8]=[CH:7][N:6]1[CH:13]([CH3:15])[CH3:14])[CH3:2] | CC(C)N1C=CN(C(C)C)[SiH]1Cl | CCN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCCCC | null | null | null | null | null | null | null | null | null | null | 25 | 4 | In an argon atmosphere, 6.80 g (151 mmol) of ethylamine was dissolved in 20 mL of hexane, and a solution obtained by dissolving 5.73 g (28.0 mmol) of Si(iPrNCHCHNiPr)(H)Cl in 5 mL of hexane was added thereto at −20° C. After stirring at room temperature for 4 hours, insoluble matters produced were separated by filtrati... | CCN[SiH]1N(C(C)C)C=CN1C(C)C | null | 89 | null |
1,117,341 | ord_dataset-4226e9b4f9f845db967ed997270dcafc | null | 2011-01-01T00:12:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH:6]=O.Cl.[NH2:14][C:15]1([C:18]([O:20][CH3:21])=[O:19])[CH2:17][CH2:16]1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH2:6][NH:14][C:15]1([C:18]([O:20][CH3:21])=[O:19])[CH2:17][CH2:16]1 | COC(=O)C1(N)CC1 | COc1ccc(C=O)cc1OC | 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 | Prepared as in Example 12-1b from 3,4-dimethoxybenzaldehyde and methyl 1-aminocyclopropanecarboxylate hydrochloride. Yield 82%. MS 266 (MH+). | COC(=O)C1(NCc2ccc(OC)c(OC)c2)CC1 | null | 82 | null |
912,341 | ord_dataset-c663259b80f947e2a8923796fb0e9a6b | null | 2009-01-01T00:10:00 | true | [Br:1][C:2]1[CH:7]=[C:6](F)[CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[CH3:12].[F:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[OH:21].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([O:21][C:15]2[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:14]=2[F:13])[CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[CH3:12... | Cc1c(Br)cc(F)cc1[N+](=O)[O-] | Oc1ccc(F)cc1F | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 120 | 18 | 1-Bromo-5-fluoro-2-methyl-3-nitro-benzene (9.40 g, 41.45 mmol) was dissolved in 90 mL dry DMF, and 2,4-difluorophenol (5.93 g, 45.58 mmol) and potassium carbonate (6.70 g, 45.58 mmol) were added. The reaction mixture was placed under nitronge and heated to 120° C. with stirring for 18 hours. The reaction mixture was co... | Cc1c(Br)cc(Oc2ccc(F)cc2F)cc1[N+](=O)[O-] | null | 59.5 | null |
1,050,636 | ord_dataset-dd320ded4b3f4764af39de99491533f7 | null | 2011-01-01T00:04:00 | true | C(O)C.C(OC(=O)[NH:10][C:11]1[CH:16]=[C:15]([CH:17]([S:26]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)(=[O:28])=[O:27])[C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=2[F:25])[C:14]([Br:36])=[CH:13][N:12]=1)(C)(C)C.Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[Br:36][C:14]1[C:15]([CH:17]([S:26]([C:29]2[CH:34]=[CH:33... | CC(C)(C)OC(=O)Nc1cc(C(c2cc(F)ccc2F)S(=O)(=O)c2ccc(Cl)cc2)c(Br)cn1 | null | null | Cl | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CCO | null | null | null | null | null | null | null | null | null | 25 | 63 | To an ethanol (2 ml) solution of t-butyl[5-bromo-4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-2-yl]carbamate (130 mg, 0.227 mmol) was added concentrated hydrochloric acid (2 ml). The resulting mixture was stirred at room temperature for 63 hours. The reaction mixture was concentrated under reduced pres... | Nc1cc(C(c2cc(F)ccc2F)S(=O)(=O)c2ccc(Cl)cc2)c(Br)cn1 | null | 67 | null |
1,730,253 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | [CH3:1][O:2][C:3](=[O:17])[CH2:4][N:5]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])C(=O)CC.CN1C(=O)N(C)CCC1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH2:37]1C[O:40][CH2:39][CH2:38]1>>[CH3:1][O:2][C:3](=[O:17])[CH:4]([NH:5][C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[C:39](=[O:40])[CH2:38][CH3:37] | C1CCOC1 | CCC(=O)N(CC(=O)OC)C(=O)OC(C)(C)C | null | C[Si](C)(C)[N-][Si](C)(C)C | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN1CCCN(C)C1=O | null | null | null | null | null | null | null | null | null | null | -78 | 1.5 | Under argon atmosphere, at −78° C., to a stirred solution of methyl-2-[tert-butoxycarbonyl-(propanoyl)-amino]-acetate (0.856 g, 3.5 mmol) in dry THF (4 mL) was initially added DMPU (0.89 g, 7.0 mmol) followed by LHMDS (1M solution in THF, 8.75 mL, 8.75 mmol) over a period of 10 min. After stirring at −78° C. for 1.5 h,... | CCC(=O)C(NC(=O)OC(C)(C)C)C(=O)OC | null | 81 | null |
642,104 | ord_dataset-ce71a906ea9c4399a2014cbaaff88c8f | null | 2004-01-01T00:07:00 | true | [CH3:1][O:2][C:3](=[O:31])[CH:4]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[NH:20])[NH:13][O:14][C:15](OCC)=[O:16])=[CH:8][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].CN(C)C=O>O>[CH3:1][O:2][C:3](=[O:31])[CH:4]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:2... | CCOC(=O)ONC(=N)c1ccc(CC(C(=O)OC)c2cccc(C(F)(F)F)c2)cc1 | null | null | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O | null | null | null | null | null | null | null | null | null | 25 | 48 | A mixture of 3-[4-(N-ethoxycarbonyloxycarbamimidoyl)-phenyl]-2-(3-trifluoromethyl-phenyl)-propionic acid methyl ester (30 mg, 68 μmol), sodium carbonate (2.0 g), dimethylformamide (10 ml), and water (10 ml) was stirred at room temperature for 2 days. The reaction mixture was evaporated, and the residue solved in potass... | COC(=O)C(Cc1ccc(-c2noc(=O)[nH]2)cc1)c1cccc(C(F)(F)F)c1 | null | 82.5 | null |
1,733,409 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | [NH:1]([C:5]1[CH:11]=[CH:10][C:8]([OH:9])=[CH:7][CH:6]=1)[C:2]([CH3:4])=[O:3].Cl.[C:13](Cl)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=1>C1COCC1>[C:13]([O:9][C:8]1[CH:10]=[CH:11][C:5]([NH:1][C:2](=[O:3])[CH3:4])=[CH:6][CH:7]=1)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=1 | O=C(Cl)c1cccnc1 | CC(=O)Nc1ccc(O)cc1 | 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 | 24 | TEA (1.2 ml, 8.6 mmol, 5.0 eq) was added to a solution of paracetamol [4147] (0.26 g, 1.7 mmol, 1.0 eq) in dry THF under argon atmosphere. At 0° C., nicotinoyl chloride hydrochloride [296] (1.53 gm, 8.6 mmol, 5.0 eq) was added to the above reaction mixture. The reaction mixture was stirred at room temperature for 24 h.... | CC(=O)Nc1ccc(OC(=O)c2cccnc2)cc1 | null | 78 | null |
1,492,731 | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | null | 2014-01-01T00:10:00 | true | [N:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[C:17]4[CH2:18][C:19]5[S:20][CH:21]=[CH:22][C:23]=5[C:16]=4[N:15](COCC[Si](C)(C)C)[N:14]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl>CO>[N:1]1([C:7]2[CH:8]=[CH:9][C:10]([C:13]3[C:17]4[CH2:18][C:19]5[S:20][CH:21]=[CH:22][C:23]=5[C:16]=4[NH:15][N:14]=3)=[CH:11][CH:12]... | C[Si](C)(C)CCOCn1nc(-c2ccc(N3CCOCC3)cc2)c2c1-c1ccsc1C2 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 100 | null | 6-(4-Morpholin-4-yl-phenyl)-4-(2-trimethylsilanyl-ethoxymethyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalen (0.21 g, 0.4 mmol) was dissolved in MeOH and treated with concentrated HCl (0.14 mL, 4.3 mmol). The reaction mixture was heated at 100° C. for 4 hr. The solution was cooled to room temperature and the resu... | c1cc2c(s1)Cc1c(-c3ccc(N4CCOCC4)cc3)n[nH]c1-2 | null | 75 | null |
1,729,791 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | [N:1]1[N:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]2=[CH:3][C:2]=1O.O=P(Cl)(Cl)[Cl:13]>>[Cl:13][C:2]1[CH:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][N:5]2[N:1]=1 | O=P(Cl)(Cl)Cl | Oc1cc2ccccn2n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 25 | null | A stirred solution of pyrazolo[1,5-a]pyridin-2-ol (27-1; 0.9 g, 0.0067 mol) in POCl3 (10 mL) was heated in a sealed tube at 145° C. for 6 h. The reaction mixture was cooled to room temperature, poured into ice cold water (20 mL) and extracted with dichloromethane (3×20 mL). The combined organic layers were washed with ... | Clc1cc2ccccn2n1 | null | null | null |
1,219,427 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | [CH2:1]([N:3]([CH2:26][CH3:27])[C:4]1[N:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:20]=[C:19]([CH3:21])[C:18]([OH:22])=[C:17]([CH2:23][CH3:24])[CH:16]=3)[N:11]=2)[CH:7]=[C:6]([CH3:25])[N:5]=1)[CH3:2].[OH-].[Na+].Br[CH:31]([OH:33])[CH3:32]>C(O)(C)C.CCOC(C)=O>[CH2:26]([N:3]([CH2:1][CH3:2])[C:4]1[N:9]=[C:8]([C:10]2[O:... | CC(O)Br | CCc1cc(-c2noc(-c3cc(C)nc(N(CC)CC)n3)n2)cc(C)c1O | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)O | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 25 | 15 | To a solution of Intermediate 11 (1.5 g, 4.08 mmol) in isopropanol (20 mL) is added 3M aq. NaOH (5 mL) followed by bromoethanol (2.90 mL, 40.8 mmol). The reaction mixture is stirred at rt for 15 h, and is then diluted with EtOAc. The org. solution is washed with 1M aq. NaOH followed by brine, dried over Na2SO4, filtere... | CCc1cc(-c2noc(-c3cc(C)nc(N(CC)CC)n3)n2)cc(C)c1OCCO | null | 105.4 | null |
246,314 | ord_dataset-5eb2900a93c842ee98f26c305e657b61 | null | 1992-01-01T00:04:00 | true | [CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]([NH2:15])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl[C:23]([O:25][CH2:26][CH3:27])=[O:24]>ClCCl.O>[C:23]([NH:15][CH:7]([C:3]1[S:4][CH:5]=[CH:6][C:2]=1[CH3:1])[CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)([O:25][CH2:26][CH3:27])... | CCOC(=O)Cl | Cc1ccsc1C(N)Cc1ccccc1 | null | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 8 | To a stirred two-phase mixture of 10 g (0.047 mol) of α-(3-methyl-2-thienyl)benzeneethanamine and 7.4 g (0.07 mol) of sodium carbonate in 150 ml of dichloromethane and 200 ml of water at 0° C. was added dropwise 7.6g (0.07 mol) of ethyl chloroformate. The resulting mixture was allowed to warm to ambient temperature and... | CCOC(=O)NC(Cc1ccccc1)c1sccc1C | null | null | null |
450,625 | ord_dataset-3bcdb559226a40d89406474c02d082d1 | null | 1999-01-01T00:12:00 | true | [NH2:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:6].[C:17]1([N:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:24](Cl)=[O:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C>C(O)C>[C:17]1([N:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:24... | Nc1cccc(C(=O)Nc2ccccc2)c1 | O=C(Cl)N(c1ccccc1)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CCO | null | null | null | null | null | null | null | null | null | null | null | A mixture of 3-amino-N-phenylbenzamide (2.0 g, 9.4 mmol), diphenylcarbamoyl chloride (2.2 g, 9.4 mmol) and triethylamine (2.6 mL, 19 mmol) in ethanol (10 mL) was heated to reflux for 4.5 hours. The mixture was cooled and concentrated, water was added, the slurry was acidified with 1 N HCl and the solid was collected, w... | O=C(Nc1ccccc1)c1cccc(NC(=O)N(c2ccccc2)c2ccccc2)c1 | null | 42.6 | null |
774,295 | ord_dataset-8214eb8444a44dc2900ccb42dbeff15e | null | 2007-01-01T00:05:00 | true | [CH:1]1([CH2:6][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([S:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=2)[C:8]([OH:10])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:22]O>S(=O)(=O)(O)O>[CH3:22][O:9][C:8](=[O:10])[CH:7]([C:11]1[CH:16]=[CH:15][C:14]([S:17][C:18]([F:21])([F:19])[F:20])=[CH:13][CH:12]=1)[CH2:6][CH:1]1[CH2:5][CH2... | O=C(O)C(CC1CCCC1)c1ccc(SC(F)(F)F)cc1 | CO | null | O=S(=O)(O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 25 | null | A solution of 3-cyclopentyl-2-(4-trifluoromethylsulfanyl-phenyl)propionic acid (1.33 g, 4.18 mmol) in methanol (10 mL) was treated slowly with 4 drops of concentrated sulfuric acid. The resulting reaction mixture was heated under reflux for 36 h. The reaction mixture was allowed to cool to 25° C. and then concentrated ... | COC(=O)C(CC1CCCC1)c1ccc(SC(F)(F)F)cc1 | null | 99 | null |
255,111 | ord_dataset-30ad5cf6083a45a387b45bebad1a4d65 | null | 1992-01-01T00:10:00 | true | [CH3:1][O:2][C:3]1[C:19]([O:20][CH3:21])=[CH:18][CH:17]=[CH:16][C:4]=1[CH:5]=[CH:6][C:7]1[S:8][C:9]2[NH:10][CH2:11][CH2:12][CH2:13][C:14]=2[N:15]=1.C(=O)([O-])[O-].[K+].[K+].[ClH:28].[CH3:29][N:30]([CH2:32][CH2:33][Cl:34])[CH3:31].O>CN(C)C=O>[ClH:34].[ClH:28].[CH3:1][O:2][C:3]1[C:19]([O:20][CH3:21])=[CH:18][CH:17]=[CH:... | COc1cccc(C=Cc2nc3c(s2)NCCC3)c1OC | CN(C)CCCl | null | Cl | O=C([O-])[O-] | [K+] | 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 | 90 | 4 | 2-(2,3-Dimethoxystyryl)-4,5,6,7-tetrahydrothiazolo[5,4-b]pyridine (1.0 g, 3.3 mmole) and powdery potassium carbonate (1.37 g, 9.92 mmole) were suspended in dimethylformamide (20 ml). To the suspension was added N,N-dimethylaminoethyl chloride hydrochloride (0.57 g, 3.97 mmole) and the mixture was heated with stirring a... | COc1cccc(C=Cc2nc3c(s2)N(CCN(C)C)CCC3)c1OC | null | 59.1 | null |
1,637,568 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [C:1]([C:5]1[CH:6]=[C:7]([NH:26][C:27]([NH:29][C@@H:30]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[C@H:33]([O:40][C:41]3[CH:42]=[CH:43][C:44]4[N:45]([C:47]([N:50]([CH:54]([CH3:56])[CH3:55])[CH:51]([CH3:53])[CH3:52])=[N:48][N:49]=4)[CH:46]=3)[CH2:32][CH2:31]2)=[O:28])[N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16... | CC(C)N(c1nnc2ccc(O[C@@H]3CC[C@H](NC(=O)Nc4cc(C(C)(C)C)nn4-c4cccc(OCCOC5CCCCO5)c4)c4ccccc43)cn12)C(C)C | null | null | Cc1ccc(S(=O)(=O)[O-])cc1 | c1cc[nH+]cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | To a solution of Intermediate 103d (100 mg, 0.13 mmol) in MeOH (2 mL) was added pyridinium p-toluenesulfonate (65 mg, 0.26 mmol) and the reaction mixture was heated to reflux temperature for 3 h. The volatiles were concentrated in vacuo and the resultant residue was partitioned between EtOAc and water. The aqueous phas... | CC(C)N(c1nnc2ccc(O[C@@H]3CC[C@H](NC(=O)Nc4cc(C(C)(C)C)nn4-c4cccc(OCCO)c4)c4ccccc43)cn12)C(C)C | null | 109.6 | null |
660,147 | ord_dataset-04d607efe1d9485eb99fafa06880f62e | null | 2005-01-01T00:02:00 | true | [Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([CH3:19])[CH:15]=[C:14]2[N:20]1[CH2:25][CH:24]=[C:23]([C:26]#[N:27])[CH2:22][CH2:21]1.Cl.C(O)=[O:30]>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16... | Cc1cc(N2CC=C(C#N)CC2)c2cccc(-c3ccc(Cl)cc3Cl)c2n1 | O=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 | 4 | In 96% formic acid (5 mL) was dissolved 8-(2,4-dichlorophenyl)-2-methyl-4-(4-cyano-1,2,3,6-tetrahydropyridin-1-yl)quinoline (1.0 g), and hydrogen chloride gas was bubbled into the solution under ice-cooling to saturate the solution therewith. The reaction mixture was stirred at room temperature for 4 hours and then dis... | Cc1cc(N2CC=C(C(N)=O)CC2)c2cccc(-c3ccc(Cl)cc3Cl)c2n1 | null | null | null |
1,718,515 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11](=[O:26])[NH:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[CH:14]=1)[C:5](O)=[O:6].[C:27]1([NH:33][CH2:34][CH2:35][NH2:36])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]([NH:36][CH2:35][CH2:34][... | O=C(O)c1ccc(C(=O)Nc2ccc(Cl)c(-c3ccccn3)c2)c(Cl)c1 | NCCNc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 62 mg of 3-chloro-4-(4-chloro-3-(pyridin-2-yl)phenylcarbamoyl)benzoic acid was coupled to N1-phenylethane-1,2-diamine via Procedure G. The crude product was purified on reverse phase HPLC to yield 2-chloro-N1-(4-chloro-3-(pyridin-2-yl)phenyl)-N4-(2-(phenylamino)ethyl)terephthalamide. MS (Q1) 505.1 (M)+. | O=C(NCCNc1ccccc1)c1ccc(C(=O)Nc2ccc(Cl)c(-c3ccccn3)c2)c(Cl)c1 | null | null | null |
1,061,922 | ord_dataset-ffbef48837674f39816de887b5dc8bae | null | 2011-01-01T00:06:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.Br[C:12]1[C:16]([Br:17])=[C:15]([NH:18][C:19]([C@@H:21]2[CH2:23][C@H:22]2[CH3:24])=[O:20])[S:14][N:13]=1>>[Br:17][C:16]1[C:12]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[N:13][S:14][C:15]=1[NH:18][C:19]([C@@H:21]1[CH2:23][C@H:22]1[CH3:24])=[O:20] | OB(O)c1ccc(F)cc1 | C[C@@H]1C[C@H]1C(=O)Nc1snc(Br)c1Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 70 | 24 | Using a similar procedure to that of Preparation VI-3, but using 1.3 equivalents of 4-fluorophenylboronic acid to 1 equivalent of (R,R)—N-[3,4-dibromoisothiazol-5-yl]-2-methylcyclopropanecarboxamide and stirring the reaction mixture at 70° C. for 1 day affords (R,R)—N-[4-bromo-3-(4-fluorophenyl)isothiazol-5-yl]-2-methy... | C[C@@H]1C[C@H]1C(=O)Nc1snc(-c2ccc(F)cc2)c1Br | null | null | null |
581,792 | ord_dataset-60f3171f0342452f8814e7f294e2be8b | null | 2003-01-01T00:02:00 | true | [OH:1][C:2]([C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1)([C:6]1[N:7]=[CH:8][N:9]([C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]=1)[CH:3]([CH3:5])[CH3:4].Br[C:40]1[N:45]=[C:44]([C:46]([NH:48][CH:49]([CH... | CC(C)C(O)(c1ccc(B(O)O)cc1)c1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cn1 | CC(C)NC(=O)c1cccc(Br)n1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | By the reaction in the same manner as in Example 33-(ii) using 4-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]phenylboronic acid (3.10 g), 6-bromo-N-isopropyl-2-pyridinecarboxamide (1.13 g) and tetrakis(triphenylphosphine)palladium(0) (0.160 g), the title compound (1.67 g) was obtained as a colorless amorpho... | CC(C)NC(=O)c1cccc(-c2ccc(C(O)(c3cn(C(c4ccccc4)(c4ccccc4)c4ccccc4)cn3)C(C)C)cc2)n1 | null | 57.9 | null |
1,431,997 | ord_dataset-5e6956e6e8c24a168866a253f4a66c6c | null | 2014-01-01T00:05:00 | true | B(Cl)(Cl)Cl.[Cl:5][C:6]1[N:7]=[N:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH:22]=[CH:21][CH:20]=[N:19]3)=[CH:14][C:13]=2[O:23]C)=[CH:10][CH:11]=1.CO>C(Cl)Cl>[Cl:5][C:6]1[N:7]=[N:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH:22]=[CH:21][CH:20]=[N:19]3)=[CH:14][C:13]=2[OH:23])=[CH:10][CH:11]=1 | COc1cc(-n2cccn2)ccc1-c1ccc(Cl)nn1 | null | null | ClB(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CO | null | null | null | null | null | null | null | null | null | 25 | 5 | BCl3 (1 M in DCM, 91 mL, 91 mmol) was added to a solution of 3-chloro-6-(2-methoxy-4-(1H-pyrazol-1-yl)phenyl)pyridazine (Intermediate 2-1, 8.6 g, 30 mmol) in DCM (150 mL) at 0° C. and the reaction was stirred for 5 h at RT. MeOH (50 mL) was added to the reaction at 0° C., then the reaction was warmed to RT and the solv... | Oc1cc(-n2cccn2)ccc1-c1ccc(Cl)nn1 | null | null | null |
118,511 | ord_dataset-7a32ed4947a84db9890d8863ca9e55fb | null | 1984-01-01T00:06:00 | true | [C:1]([C:4]1[NH:8][CH:7]=[N:6][C:5]=1[CH3:9])(=[O:3])[CH3:2].[Br:10]Br>Br>[CH3:9][C:5]1[N:6]=[CH:7][NH:8][C:4]=1[C:1](=[O:3])[CH2:2][Br:10] | BrBr | CC(=O)c1[nH]cnc1C | null | Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 1.25 | A solution of 1.57 g (12.6 mmol) of 5-acetyl-4-methylimidazole in 15 ml of concentrated hydrobromic acid was warmed to 50° and a solution of 2.01 g (12.6 mmol) of bromine in 15 ml of concentrated hydrobromic acid was added over 0.75 hour. The mixture was stirred at 50° for 1.25 hour, then concentrated. The residue was ... | Cc1nc[nH]c1C(=O)CBr | null | null | null |
1,231,982 | ord_dataset-e96f5a2842f14e5380461c234100f05a | null | 2012-01-01T00:12:00 | true | [OH:1][CH2:2][CH:3]([NH:5][C:6]([C:8]1[C:9]([CH:14]([F:16])[F:15])=[N:10][N:11]([CH3:13])[CH:12]=1)=[O:7])[CH3:4].Br[C:18]1[C:23]([Cl:24])=[CH:22][C:21]([C:25]([F:28])([F:27])[F:26])=[CH:20][N:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:24][C:23]1[C:18]([O:1][CH2:2][CH:3]([NH:5][C:6]([C:8]2[C:9]([CH:14]([F:16])[F:15])... | CC(CO)NC(=O)c1cn(C)nc1C(F)F | FC(F)(F)c1cnc(Br)c(Cl)c1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 100 | 3 | A solution of 2.3 g 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (2-hydroxy-1-methyl-ethyl)-amide (10.0 mmol, prepared as described in example P5a) and 2.6 g 2-bromo-3-chloro-5-trifluoromethyl-pyridine (10 mmol) in dimethylformamide (30 ml) is treated at ambient temperature with 2.8 g potassium carbonate (20... | CC(COc1ncc(C(F)(F)F)cc1Cl)NC(=O)c1cn(C)nc1C(F)F | null | 33.9 | null |
606,587 | ord_dataset-273fda773e864aaf9b71a30a2d9f2162 | null | 2003-01-01T00:08:00 | true | [Cl:1][C:2]1[N:7]=[N:6][C:5]([NH:8][NH:9][C:10](=O)[C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:3]=1>C(OCC)(=O)C>[C:11]([C:10]1[N:6]2[N:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]2=[N:8][N:9]=1)([CH3:14])([CH3:13])[CH3:12] | CC(C)(C)C(=O)NNc1ccc(Cl)nn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | 170 | null | 2.78 g of N′-(6-chloro-3-pyridazinyl)-2,2-dimethylpropionohydrazide was stirred under heating at an external temperature of 170° C. for 10 minutes. After cooling, the reaction mixture was dissolved in ethyl acetate, subjected to silica gel column chromatography, and eluted with ethyl acetate. The desired fraction was c... | CC(C)(C)c1nnc2ccc(Cl)nn12 | null | 92.9 | null |
462,992 | ord_dataset-5ca9db262dd24c5a9315cdc8ef055b7e | null | 2000-01-01T00:04:00 | true | [OH:1][CH:2]1[CH:7]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]3[CH:25]=[CH:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=3)=[CH:10][CH:9]=2)[CH2:6][CH2:5][N:4]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:3]1.[CH3:33][O:34][C:35]1[CH:42]=[CH:41][CH:40]=[CH:39][C:36]=1[CH2:37]Cl>>[CH3:3... | COc1ccccc1CCl | CC(C)(C)OC(=O)N1CCC(c2ccc(OCc3ccc4ccccc4c3)cc2)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 | In analogy to the procedure described in Example 3(c), by alkylating tert-butyl (3RS,4RS)-3-hydroxy-4-[4-(naphthalen-2-ylmethoxy)-phenyl]-piperidine-1-carboxylate with 2-methoxybenzyl chloride there was obtained tert-butyl (3RS,4RS)-3-(2-methoxy-benzyloxy)-4-[4-(naphthalen-2-ylmethoxy)-phenyl]-piperidine-1-carboxylate ... | COc1ccccc1COC1CN(C(=O)OC(C)(C)C)CCC1c1ccc(OCc2ccc3ccccc3c2)cc1 | null | null | null |
1,006,794 | ord_dataset-7448b89163bf426c9d9777809ce24cec | null | 2010-01-01T00:11:00 | true | [CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:16][CH2:15][N:14]([C@H:17]2[CH2:22][CH2:21][C:20](=O)[CH2:19][C@H:18]2[C:24]([O:26][CH3:27])=[O:25])[C:13]1=[O:28])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:29]([NH2:33])([CH3:32])([CH3:31])[CH3:30].[BH4-].[Na+].C([O-])(O)=O.[Na+]>CS(C)=O.CO>[CH2:1]([O:8][C:9]([NH:11][C... | COC(=O)[C@@H]1CC(=O)CC[C@@H]1N1CC[C@H](NC(=O)OCc2ccccc2)C1=O | CC(C)(C)N | null | O=C([O-])O | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | CO | null | null | null | null | null | null | null | null | null | 25 | 2.5 | A solution of (1R,2S)-methyl 2-((S)-3-(benzyloxy-carbonylamino)-2-oxopyrrolidin-1-yl)-5-oxocyclo-hexanecarboxylate (3.1 g, 8 mmol) in DMSO (7 ml) was treated with t-butylamine (1.75 g, 24 mol) and stirred for 10 minutes before Ti(i-OPr)4 (6.8 g, 24 mol) was added and the resulting mixture was stirred at room temperatur... | COC(=O)[C@@H]1C[C@H](NC(C)(C)C)CC[C@@H]1N1CC[C@H](NC(=O)OCc2ccccc2)C1=O | null | 84.2 | null |
1,557,125 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([O:9][CH3:10])=[O:8].[Cl-].[Al+3].[Cl-].[Cl-].[C:15](Cl)([CH3:18])([CH3:17])[CH3:16]>C(Cl)Cl>[C:15]([C:5]1[S:4][C:3]([C:7]([O:9][CH3:10])=[O:8])=[C:2]([CH3:1])[CH:6]=1)([CH3:18])([CH3:17])[CH3:16] | COC(=O)c1sccc1C | CC(C)(C)Cl | null | [Al+3] | [Cl-] | 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 | -78 | 0.17 | A solution of methyl 3-methylthiophene-2-carboxylate 109a (33 g, 0.211 mol) in dry CH2Cl2 (30 mL) was added dropwise to a mixture of aluminum chloride (40 g, 0.297 mol) and dry CH2Cl2 (200 mL) at −78° C., under nitrogen. The reaction mixture was stirred for 10 min at −78° C., and a solution of tert-butyl chloride (23 m... | COC(=O)c1sc(C(C)(C)C)cc1C | null | 42.4 | null |
1,659,166 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [CH2:1]([C:8]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:19](=[O:28])[CH:20]=[CH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:9](=[O:18])[CH:10]=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].C(OCC)(=O)C>[CH2:29]([C:8]([CH2:1][C:2]1[CH:3]=[CH:... | O=C(C=Cc1ccccc1)C(Cc1ccccc1)(Cc1ccccc1)C(=O)C=Cc1ccccc1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | 4,4-Dibenzyl-1,7-diphenyl-1, 6-heptadiene-3,5-dione (12b, 70 mg, 0.2 mmol) and palladium on activated carbon (0.10 g, 10%) were combined in ethyl acetate (25 ml). The mixture was placed under a hydrogen atmosphere (60 psi) on a Parr apparatus for 5 hr at room temperature. The resulting mixture was filtered through celi... | O=C(CCc1ccccc1)C(Cc1ccccc1)(Cc1ccccc1)C(=O)CCc1ccccc1 | null | 65.1 | null |
1,057,045 | ord_dataset-373415d3e0e54004837cf4831e67666f | null | 2011-01-01T00:05:00 | true | [OH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[N:7]([CH3:12])[C:8](=[S:11])[NH:9][N:10]=1.Br[CH2:14][CH:15]1[CH2:17][CH2:16]1.ClCCl.C([O-])(O)=O.[Na+]>CN(C)C=O>[CH:15]1([CH2:14][S:11][C:8]2[N:7]([CH3:12])[C:6]([CH2:5][CH2:4][CH2:3][CH2:2][OH:1])=[N:10][N:9]=2)[CH2:17][CH2:16]1 | BrCC1CC1 | Cn1c(CCCCO)n[nH]c1=S | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CN(C)C=O | null | null | null | null | null | null | null | null | null | 60 | null | 5-(4-hydroxybutyl)-4-methyl-2,4-dihydro-3H-1,2,4-triazole-3-thione (0.3 g), (bromomethyl)cyclopropane (0.17 ml) and triethyl ammine (0.27 ml) were dissolved in dimethylformamide (2 ml). Reaction was heated at 60° C. for 2 h. Dichloromethane and NaHCO3 saturated solution were added. Solvent was removed, under reduced pr... | Cn1c(CCCCO)nnc1SCC1CC1 | null | null | null |
956,666 | ord_dataset-ed65749688da45af8a8432967b017729 | null | 2010-01-01T00:05:00 | true | [Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9](NC1CCN(C2C=CN=C(Cl)N=2)CC1)=[O:10].[Cl:25][C:26]1[CH:27]=[C:28]([CH:31]=[C:32]([N:34]2[CH2:39][CH2:38][CH:37]([OH:40])[CH2:36][CH2:35]2)[N:33]=1)[C:29]#[N:30].CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([... | N#Cc1cc(Cl)nc(N2CCC(O)CC2)c1 | Cc1[nH]c(C(=O)NC2CCN(c3ccnc(Cl)n3)CC2)c(Cl)c1Cl | null | CCOC(=O)/N=N/C(=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 | 18 | 3,4-Dichloro-5-methyl-1H-pyrrole-2-carboxylic acid (Intermediate 3, 164 mg, 0.84 mmol) was dissolved in anhydrous THF (3 ml). 2-Chloro-6-(4-hydroxypiperidin-1-yl)isonicotinonitrile (Intermediate 26), 200 mg, 0.84 mmol) was added, then DEAD (133 μl, 0.84 mmol) was added dropwise followed by triphenylphosphine (221 mg, 0... | Cc1[nH]c(C(=O)OC2CCN(c3cc(C#N)cc(Cl)n3)CC2)c(Cl)c1Cl | null | null | null |
6,175 | ord_dataset-a5669edbeffe43bf8514c1bfede8f882 | null | 1976-01-01T00:04:00 | true | [NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:5]([NH:7][C@H:8]([C:10]([NH:12][C@H:13]([C:23]([NH:25][C@H:26]([C:28]([NH:30][C@H:31]([C:39]([N:41]1[CH2:84][CH2:83][CH2:82][C@H:42]1[C:43]([NH:45][C@H:46]([C:51]([NH:53][C@H:54]([C:64]([NH:66][C@H:67]([C:75]([O:77][C:78]([CH3:81])([CH3:80])[CH3:79])=[O:76])[CH2:68][C:69]1[CH:74]=[C... | CC(C)C[C@H](NC(=O)[C@@H]1CCCN1C(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](C)NC(=O)[C@H](CCC(=O)OC(C)(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)OCc1ccccc1)C(=O)N[C@@H](CCC(=O)OC(C)(C)C)C(=O)N[C@@H](Cc1ccccc1)C(=O)OC(C)(C)C | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | 78.95 g. (60.15 mmoles) of Z-31-39-OtBu are dissolved in 1500 ml. of 80 % acetic acid, and the mixture is hydrogenated in the presence of palladium-on-carbon. When the reaction terminates, the catalyst is filtered off, and the filtrate is evaporated to dryness. The residue is triturated with ether and filtered. 74.35 g... | CC(C)C[C@H](NC(=O)[C@@H]1CCCN1C(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](C)NC(=O)[C@H](CCC(=O)OC(C)(C)C)NC(=O)[C@H](C)NC(=O)[C@@H](N)CO)C(=O)N[C@@H](CCC(=O)OC(C)(C)C)C(=O)N[C@@H](Cc1ccccc1)C(=O)OC(C)(C)C | null | 99 | null |
687,168 | ord_dataset-56747de2718a4ac5bf061651d1cc9e3e | null | 2005-01-01T00:10:00 | true | C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.BrN1C(=O)CCC1=O.[CH:28]1([CH2:34][CH:35]([C:39]2[CH:44]=[CH:43][C:42]([S:45]([CH3:48])(=[O:47])=[O:46])=[C:41]([C:49]([F:52])([F:51])[F:50])[CH:40]=2)[C:36]([OH:38])=O)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.[NH2:53][C:54]1[S:55][CH:56]=[CH:57][N:58]=1>C(Cl)Cl>[CH:28]1([CH2:34][... | Nc1nccs1 | CS(=O)(=O)c1ccc(C(CC2CCCCC2)C(=O)O)cc1C(F)(F)F | null | O=C1CCC(=O)N1Br | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | 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 | A solution of triphenylphosphine (279 mg, 1.06 mmol) in methylene chloride (5 mL) was cooled to 0° C. and then treated with N-bromosuccinimide (188.7 mg, 1.06 mmol). The reaction mixture was stirred at 0° C. for 30 min and then treated with a solution of 3-cyclohexyl-2-(4-methanesulfonyl-3-trifluoromethyl-phenyl)-propi... | CS(=O)(=O)c1ccc(C(CC2CCCCC2)C(=O)Nc2nccs2)cc1C(F)(F)F | null | 28.8 | null |
1,274,567 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[CH:16]=[C:15](/[CH:17]=[CH:18]/[C:19]3[C:27]4[C:22](=[N:23][C:24]([F:28])=[CH:25][CH:26]=4)[N:21]([CH2:29][C:30]4[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=4)[N:20]=3)[N:14]=[C:13]([O:38][CH3:39])[C:12]=2[Cl:40])[CH:9]=1)[C:5]#[N:6].[H][H]>C1COCC1.CO.[Pd]>[C... | [H][H] | COc1ccc(Cn2nc(/C=C/c3cc(Oc4cc(Cl)cc(C#N)c4)c(Cl)c(OC)n3)c3ccc(F)nc32)cc1 | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CO | null | null | null | null | null | null | null | null | null | null | null | Compound 4-1 (400 mg; 0.694 mmol) was dissolved in 6 mL THF/MeOH (1:1) and the system purged with nitrogen (3×). 10% Pd/C (739 mg; 0.694 mmol) was then added to the reaction mixture which was then purged (3×) with nitrogen and then with hydrogen (3×). The purged reaction mixture then remained under atmospheric pressure... | COc1ccc(Cn2nc(CCc3cc(Oc4cc(Cl)cc(C#N)c4)c(Cl)c(OC)n3)c3ccc(F)nc32)cc1 | null | null | null |
539,324 | ord_dataset-49124ff635234889bd8dcfe87f4f9013 | null | 2002-01-01T00:04:00 | true | [NH2-].[Na+].[CH:3]1[CH2:5][CH:4]=1.I[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]=[CH2:14].C(O)C>N.CCOCC>[CH2:14]([C:3]1[CH2:5][CH:4]=1)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH:8]=[CH2:7] | C=CCCCCCCI | C1=CC1 | null | N | [NH2-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | CCOCC | null | null | null | null | null | null | null | null | null | -78 | 0.5 | A mixture of 0.43 g (11 mmol) of sodium amide in roughly 15 ml of ammonia was cooled to −78° C. A chilled solution of cyclopropene in ammonia (1:1, 0.85 g, 10 mmol) was poured into the reaction mixture. The reaction mixture was stirred at −78° C. for ½ hour, warmed briefly to the ammonia boiling point, then recooled to... | C=CCCCCCCC1=CC1 | null | 67 | null |
1,349,186 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | [CH3:1][C:2]1([CH3:17])[CH2:11][CH2:10][C:9]2[N:5]([CH:6]=[CH:7][N:8]=2)[C:4]2[CH:12]=[C:13]([NH2:16])[CH:14]=[CH:15][C:3]1=2.Cl[C:19]1[N:24]=[C:23]([NH:25][C:26]2[C:35]([F:36])=[CH:34][CH:33]=[CH:32][C:27]=2[C:28]([NH:30][CH3:31])=[O:29])[C:22]([Cl:37])=[CH:21][N:20]=1>>[Cl:37][C:22]1[C:23]([NH:25][C:26]2[C:35]([F:36]... | CC1(C)CCc2nccn2-c2cc(N)ccc21 | CNC(=O)c1cccc(F)c1Nc1nc(Cl)ncc1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 2-[5-Chloro-2-(6,6-dimethyl-5,6-dihydro-4H-3,10b-diaza-benz[e]azulen-9-ylamino)-pyrimidin-4-ylamino]-3-fluoro-N-methyl-benzamide was prepared from 6,6-Dimethyl-5,6-dihydro-4H-3,10b-diaza-benz[e]azulen-9-ylamine and 2-(2,5-Dichloro-pyrimidin-4-ylamino)-3-fluoro-N-methyl-benzamide in an analogous manner to Example 1223c.... | CNC(=O)c1cccc(F)c1Nc1nc(Nc2ccc3c(c2)-n2ccnc2CCC3(C)C)ncc1Cl | null | null | null |
975,958 | ord_dataset-f886e51ba1484c76a94bce1482f1eab9 | null | 2010-01-01T00:07:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH:16]3[CH2:17][CH2:18][CH2:19][CH:12]2[C:13](=[CH:21]O)[C:14](=O)[CH2:15]3)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl.[NH2:24][C:25]([NH2:27])=[NH:26]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH:16]3[CH2:17][CH2:18][CH2:19][CH:12]2[C:13]2[CH:21]=[N:24][C:25]([NH2:27])=[N:26][C... | O=C1CC2CCCC(C1=CO)N2S(=O)(=O)c1ccc(Cl)cc1 | N=C(N)N | 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 | Prepared as described in Example 5 using 9-(4-chlorophenylsulfonyl)-2-(hydroxymethylene)-9-azabicyclo[3.3.1]nonan-3-one which was prepared as described in Example 34 and guanidine hydrochloride. See also: Hasan, Mashooda; Rashid, Naghmana; Khan, Khalid Mohammed; Snatzke, Guenther; Duddeck, Helmut; Voelter, Wolfgang Lie... | Nc1ncc2c(n1)CC1CCCC2N1S(=O)(=O)c1ccc(Cl)cc1 | null | null | null |
876,585 | ord_dataset-e1c3af9b105b4af09a5171403bbfc06f | null | 2009-01-01T00:04:00 | true | [N+:1]([C:4]1[CH:19]=[CH:18][C:7]([O:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:6][CH:5]=1)([O-])=O.O.O.[Sn](Cl)Cl.[OH-].[Na+]>C(O)C>[N:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[O:11][CH2:10][CH2:9][O:8][C:7]1[CH:6]=[CH:5][C:4]([NH2:1])=[CH:19][CH:18]=1 | O=[N+]([O-])c1ccc(OCCOc2ccccn2)cc1 | null | null | Cl[Sn]Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCO | null | null | null | null | null | null | null | null | null | null | 1 | 2-[2-(4-Nitrophenoxy)ethoxy]pyridine (100 mg, 0.38 mmol) and tin (II) chloride dihydrate (433 mg, 1.92 mmol) were dissolved in ethanol (1.5 mL) and refluxed under nitrogen for 18 h. The reaction mixture was basified to pH 12 with 3M aqueous sodium hydroxide solution. The reaction mixture was stirred for 1 h and then fi... | Nc1ccc(OCCOc2ccccn2)cc1 | null | null | null |
1,380,476 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | C(OC([N:11]1[CH2:18][C@@H:17]2[C@@:13]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])([CH2:14][CH2:15][C@@H:16]2[F:19])[CH2:12]1)=O)C1C=CC=CC=1.[H][H]>CO.[C].[Pd]>[C:24]([O:23][C:21]([NH:20][C@@:13]12[CH2:14][CH2:15][C@H:16]([F:19])[C@@H:17]1[CH2:18][NH:11][CH2:12]2)=[O:22])([CH3:27])([CH3:25])[CH3:26] | [H][H] | CC(C)(C)OC(=O)N[C@@]12CC[C@H](F)[C@@H]1CN(C(=O)OCc1ccccc1)C2 | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | {(1S,5R,6S)-1-tert-Butoxycarbonylamino-6-fluoro-3-azabicyclo[3,3,0]octan-3-yl}carboxylic acid benzyl ester (132 mg, 0.35 mmol) was dissolved in methanol (10 mL). 10% palladium-carbon (M, wet) (50 mg) was added, and the mixture was stirred in a hydrogen atmosphere for three hours. The catalyst was removed by filtration,... | CC(C)(C)OC(=O)N[C@@]12CC[C@H](F)[C@@H]1CNC2 | null | 99.4 | null |
1,330,032 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | [C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13](Br)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])(C)(C)C.[C:23]([O:27][C:28]([N:30]1[CH2:34][CH2:33][CH2:32][C:31]1([CH:38]=[O:39])[CH2:35][CH2:36][CH3:37])=[O:29])([CH3:26])([CH3:25])[CH3:24]>CCOCC>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH... | CCCC1(C=O)CCCN1C(=O)OC(C)(C)C | CC(C)(C)OC(=O)n1ccc2cc(Br)ccc21 | null | [Li]C(C)(C)C | 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 | 0.5 | To a stirred solution of 5-bromo-indole-1-carboxylic acid tert-butyl ester (0.700 g, 2.37 mmol) in ether (20 mL) at −78° C. and under nitrogen was added tert-butyllithium (3.64 mL of 1.43 M solution in pentanes, 5.21 mmol) dropwise. After 30 minutes, a solution of 2-formyl-2-propyl-pyrrolidine-1-carboxylic acid tert-bu... | CCCC1(C(O)c2ccc3c(ccn3C(=O)OC(C)(C)C)c2)CCCN1C(=O)OC(C)(C)C | null | 43 | null |
735,954 | ord_dataset-76dd1b78ee414d2da0ed30700ef026f7 | null | 2006-01-01T00:10:00 | true | [Br:1][C:2]1[CH:3]=[C:4]([C:11](O)=[O:12])[C:5](=[CH:9][CH:10]=1)[C:6](O)=[O:7]>C1COCC1>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][OH:7])=[C:4]([CH2:11][OH:12])[CH:3]=1 | O=C(O)c1ccc(Br)cc1C(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 3 | To a solution of 4-bromophthalic acid (3.0 g, 12.24 mmol) in 30 mL of THF was added a solution of borane-THF complex (1.0M) dropwise at 0° C. The solution was warmed to rt and stirred for 3 h. The reaction mixture was quenched by addition of HCl (2N) at 0° C. The product was extracted with ethyl acetate and washed with... | OCc1ccc(Br)cc1CO | null | 105.4 | null |
1,515,340 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | S(=O)(=O)(O)O.[O:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[CH:11]=[CH:12][C:13](=[O:25])[C:14](=[CH:19][C:20]1[O:21][CH:22]=[CH:23][CH:24]=1)[CH2:15][C:16]([OH:18])=[O:17].[CH3:26][CH2:27]OC(C)=O.C(=O)(O)[O-].[Na+]>C(O)C>[O:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[CH:11]=[CH:12][C:13](=[O:25])[C:14](=[CH:19][C:20]1[O:21][CH:22]=[CH:23][CH:... | CCOC(C)=O | O=C(O)CC(=Cc1ccco1)C(=O)C=Cc1ccco1 | 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 | CCO | null | null | null | null | null | null | null | null | null | null | 25 | null | To prepare a starting compound of Formula III, 12 g of levulinic acid (0.104 mol, 1.0 eq) was first dissolved in 66 mL of water. A solution of 15.4 g of sodium carbonate (0.146 mol, 2.8 eq of base relative to levulinic acid) was slowly added. The resulting suspension was stirred for 30 minutes at room temperature. The ... | CCOC(=O)CC(=Cc1ccco1)C(=O)C=Cc1ccco1 | null | 88 | null |
263,951 | ord_dataset-a7bd0db0684c464bb02ff6a36065fee3 | null | 1993-01-01T00:03:00 | true | [ClH:1].[O:2]=[S:3]1(=[O:16])[N:7]([CH3:8])[CH2:6][CH2:5][N:4]1[C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1.O=S1(=O)N(C)CC[N:19]1C1C=CC([N+]([O-])=O)=CC=1>>[ClH:1].[O:16]=[S:3]1(=[O:2])[N:7]([CH3:8])[CH2:6][CH2:5][N:4]1[C:9]1[CH:15]=[CH:14][C:12]([NH:13][NH2:19])=[CH:11][CH:10]=1 | CN1CCN(c2ccc(N)cc2)S1(=O)=O | CN1CCN(c2ccc([N+](=O)[O-])cc2)S1(=O)=O | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared in 96% yield from 4-(1,1-dioxo-5-methyl-1,2,5-thiadiazolidin-2-yl)aniline hydrochloride using a similar method to that described for Intermediate 1 (step 1); yellow solid; δH (360 MHz, DMSO-d6) 7.15 (2H, d, J=8.9 Hz, Ar--H), 6.92 (2H, d, J=8.9 Hz, Ar--H), 3.74 (2H, t, J=6.4 Hz, --CH2 --)... | CN1CCN(c2ccc(NN)cc2)S1(=O)=O | null | 96 | null |
665,157 | ord_dataset-5a3d853c53674888a5691dce2e398792 | null | 2005-01-01T00:03:00 | true | [CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][CH3:12])[CH:9]=2)[C:4]([C:13]([OH:15])=O)=[C:3]1[CH3:16].C(Cl)(=O)C(Cl)=O.[CH2:23]([NH2:27])[CH:24]([CH3:26])[CH3:25]>>[CH2:23]([NH:27][C:13]([C:4]1[C:5]2[C:10](=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=2)[N:2]([CH3:1])[C:3]=1[CH3:16])=[O:15])[CH:24]([CH3:26])[CH3:25... | CC(C)CN | COc1ccc2c(C(=O)O)c(C)n(C)c2c1 | null | O=C(Cl)C(=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 | This material was prepared from 1,2-dimethyl-6-methoxy-1H-indole-3-carboxylic acid 16c, oxalyl chloride and isobutylamine in a manner as previously described for example 16d. 1H NMR (300 MHz, CDCl3) δ7.56 (1H, d, J=8.6 Hz), 6.85 (1H, dd, J=2.2, 8.6 Hz), 6.78 (1H, d, J=2.2 Hz), 3.87 (3H, s), 3.63 (3H, s), 3.32 (2H, m), ... | COc1ccc2c(C(=O)NCC(C)C)c(C)n(C)c2c1 | null | null | null |
1,203,264 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][N:11]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]2[CH:28]=[CH:27][N:26]=[C:25](Cl)[N:24]=2)[CH:18]=1)[S:12]([CH3:15])(=[O:14])=[O:13])(C)(C)C.[NH2:31][CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][C:37]([OH:40])=[CH:36][CH:35]=1>>[NH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH2:16][C:17]1[C... | CC(C)(C)OC(=O)NCCCN(Cc1cccc(-c2ccnc(Cl)n2)c1)S(C)(=O)=O | NCCc1ccc(O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Intermediate 4 from above was coupled with tyramine following procedure F and the resulting product deprotected following procedure G. LC-MS showed the product had the expected M+H+ of 456. 1H NMR (Varian 300 MHz, DMSO-d6, shifts relative to the solvent peak at 2.49 ppm) δ 8.5 (d, 1H) 8.1 (m, 2H) 8.0 (s, 2H) 7.6 (m, 2H... | CS(=O)(=O)N(CCCN)Cc1cccc(-c2ccnc(NCCc3ccc(O)cc3)n2)c1 | null | null | null |
424,310 | ord_dataset-1a231de00bfe4443b547e1f03885ed41 | null | 1999-01-01T00:01:00 | true | Cl.Cl.[NH2:3][C:4]1[C:19]([Cl:20])=[CH:18][C:7]([C:8]([NH:10][CH2:11][CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[O:9])=[C:6]([O:21][CH3:22])[CH:5]=1.Br[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([C:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[N:33]([CH:40]([CH3:42])[CH3:41])[CH:32]=1)=[O:30]>>[ClH:20].... | COc1cc(N)c(Cl)cc1C(=O)NCC1CCNCC1 | CC(C)n1cc(C(=O)CCCCCBr)c2ccccc21 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 4-Amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide dihydrochloride (1.90 g) as starting compound and 6-bromo-1-(1-isopropyl-1 H-indol-3-yl)-1-hexanone (1.90 g) were reacted and treated in the same manner as in Example 199 to give 0.70 g of 4-amino-5-chloro-2-methoxy-N-((1-(6-(1-isopropyl-1H-indol-3-yl)-6-oxoh... | COc1cc(N)c(Cl)cc1C(=O)NCC1CCN(CCCCCC(=O)c2cn(C(C)C)c3ccccc23)CC1 | null | 46.3 | null |
788,171 | ord_dataset-4ad5db8537994579bef51f16dd8bf0bd | null | 2007-01-01T00:08:00 | true | [OH:1][CH2:2][C:3]1[N:7]([CH2:8][CH:9]([CH3:11])[CH3:10])[C:6]([SH:12])=[N:5][N:4]=1.I[CH2:14][CH3:15].C(N(CC)CC)C>C(O)C>[CH2:14]([S:12][C:6]1[N:7]([CH2:8][CH:9]([CH3:10])[CH3:11])[C:3]([CH2:2][OH:1])=[N:4][N:5]=1)[CH3:15] | CC(C)Cn1c(S)nnc1CO | CCI | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CCO | null | null | null | null | null | null | null | null | null | null | null | A solution of 3-hydroxymethyl-4-isobutyl-5-mercapto-4H-1,2,4-triazole (1.0 g), iodoethane (1.0 g) and triethylamine (1.1 ml) in ethanol (10 ml) was stirred for 2 days at 70° C. The solvent was removed under reduced pressure, and the obtained residue was purified by column chromatography (ethanol:ethyl acetate 1:9→1:5),... | CCSc1nnc(CO)n1CC(C)C | null | 87 | null |
1,551,181 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [CH3:1][N:2]([CH3:32])[C:3]([C:5]1[N:26]([CH:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)[C:8]2[N:9]=[C:10]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([N:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)=[CH:16][N:15]=3)[N:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4].[CH3:33][C@@H:34]1[CH2:36][O:35]1>C(O)C>[CH3:1][N:2]([CH3:32])[C:3]([C:5]1[N:26]... | CN(C)C(=O)c1cc2cnc(Nc3ccc(N4CCNCC4)cn3)nc2n1C1CCCC1 | C[C@@H]1CO1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | To a solution of 7-cyclopentyl-2-(5-piperazin-1-yl-pyridin-2-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (55 mg, 0.123 mmol) and (R)-2-methyl-oxirane (250 mg, 4.3 mmol) in 5 mL of ethanol is heated at 70° C. for 18 h. Following SiO2 chromatography, eluting with 0-10% (2M NH3 in MeOH)/dichlorome... | C[C@@H](O)CN1CCN(c2ccc(Nc3ncc4cc(C(=O)N(C)C)n(C5CCCC5)c4n3)nc2)CC1 | null | 16.5 | null |
880,792 | ord_dataset-3592bd645cd143ee8274cd0d834ae581 | null | 2009-01-01T00:05:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([OH:18])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].F[C:33]1[CH:40]=[CH:39][C:36]([C:37]#[N:38])=[CH:35][CH:34]=1>CC(N(C)C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=... | N#Cc1ccc(F)cc1 | CC(C)(C)OC(=O)N1CCc2cc(O)ccc2C1 | 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 | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | 25 | null | Combine in a round bottom flask equipped with a Dean Stark Trap 6-Hydroxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (1.59 g, 6.36 mmol), toluene, dimethylacetamide (10 ml and 30 ml respectively), K2CO3 (1.25 g, 9.04 mmol), and 4-Fluorobenzonitrile (0.72 g, 6.04 mmol). Reflux the reaction under a Ni... | CC(C)(C)OC(=O)N1CCc2cc(Oc3ccc(C#N)cc3)ccc2C1 | null | 91.1 | null |
1,666,665 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:29][CH2:28][C:11]3([CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@H:13]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:12]3)[CH2:10][CH2:9]2)[CH:5]=[C:4]([O:30][C@H:31]([C:36]2[CH:41]=[C:40](Br)[CH:39]=[CH:38][C:37]=2Br)[C:32]([F:35])([F:34])[F:33])[N:3]=1.[C:4... | OB(O)c1ccccc1 | CCOC(=O)[C@@H]1CC2(CCN(c3cc(O[C@H](c4cc(Br)ccc4Br)C(F)(F)F)nc(N)n3)CC2)CN1C(=O)OC(C)(C)C | null | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 90 | null | To a solution of (S)-2-tert-butyl 3-ethyl 8-(2-amino-6-((R)-1-(2,5-dibromophenyl)-2,2,2-trifluoroethoxy)pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-2,3-dicarboxylate (660 mg, 0.95 mmol) in dioxane (12 mL) was added phenyl boronic acid (290 mg, 2.4 mmol), Pd2(dppf)Cl2 (70 mg, 0.095 mmol), and Na2CO3 (6.0 mL, 2.0 M, aq). T... | CCOC(=O)[C@@H]1CC2(CCN(c3cc(O[C@H](c4cc(-c5ccccc5)ccc4-c4ccccc4)C(F)(F)F)nc(N)n3)CC2)CN1C(=O)OC(C)(C)C | null | null | null |
200,449 | ord_dataset-31f00a039ca0424788e5e1970d25a8fd | null | 1989-01-01T00:12:00 | true | [OH:1][CH:2]1[NH:6][C:5](=[O:7])[CH:4]=[CH:3]1.[CH:8]1(O)[CH2:12][CH2:11][CH2:10][CH2:9]1>>[CH:8]1([O:1][CH:2]2[NH:6][C:5](=[O:7])[CH:4]=[CH:3]2)[CH2:12][CH2:11][CH2:10][CH2:9]1 | OC1CCCC1 | O=C1C=CC(O)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 | 60 | null | A mixture of 4.5 g of 1,5-dihydro-5-hydroxy-2H-pyrrol-2-one, 100 cm3 of cyclopentanol and 2.25 g of Amberlite IR 120 H is maintained for 8 hours at 60° C. It is then allowed to cool, is filtered, and evaporated to dryness. The residue is chromatographed on silica (eluent: ethyl acetate-n-hexane, 1--1). 3 g of the expec... | O=C1C=CC(OC2CCCC2)N1 | null | null | null |
717,160 | ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | null | 2006-01-01T00:07:00 | true | [OH-].[K+].[CH2:3]([O:5][C:6](=[O:26])[CH:7]([CH2:13][CH:14]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15]1)[C:8]([O:10]CC)=[O:9])[CH3:4]>C(O)C>[CH2:3]([O:5][C:6](=[O:26])[CH:7]([CH2:13][CH:14]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:... | CCOC(=O)C(CC1CCN(C(=O)OC(C)(C)C)C1)C(=O)OCC | null | null | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 25 | 8 | A solution of KOH (0.26 g; 4.6 mmol) in ethanol (7 mL) was added to a solution of 2-(1-tert-butoxycarbonyl-pyrrolidin-3-ylmethyl)-malonic acid diethyl ester (1.52 g; 4.4 mmol) in ethanol (7 mL) at 0° C. The reaction mixture was stirred at room temperature overnight, concentrated under reduced pressure and the residue w... | CCOC(=O)C(CC1CCN(C(=O)OC(C)(C)C)C1)C(=O)O | null | 81.4 | null |
960,467 | ord_dataset-ed65749688da45af8a8432967b017729 | null | 2010-01-01T00:05:00 | true | [F:1][C:2]([F:19])([F:18])[C:3](=O)[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1)=O.[NH2:20][C:21]1[CH:25]=[CH:24][NH:23][N:22]=1>C(O)(=O)C>[F:1][C:2]([F:19])([F:18])[C:3]1[N:22]2[N:23]=[CH:24][CH:25]=[C:21]2[N:20]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[... | Nc1cc[nH]n1 | O=C(CC(=O)C(F)(F)F)c1ccc(C(F)(F)F)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | 25 | null | A mixture of 4,4,4-trifluoro-1-(4-trifluoromethyl-phenyl)-butane-1,3-dione (Example C.1, method 1, step 1) (2.84 g, 10 mmol) and 3-aminopyrazole (0.83 g, 10 mmol) in acetic acid (20 mL) were refluxed for 4 h. The reaction mixture was cooled to rt and poured into ice water (200 mL), extracted with EtOAc, dried over MgSO... | FC(F)(F)c1ccc(-c2cc(C(F)(F)F)n3nccc3n2)cc1 | null | 99 | null |
1,134,019 | ord_dataset-aaeaab5f3720492494c1cbbdd0ed2820 | null | 2012-01-01T00:02:00 | true | [F:1][C:2]1[CH:3]=[C:4]([CH:29]=[C:30]([N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)[CH:31]=1)[C:5]([NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([O:18][C:19]2[CH:24]=[CH:23][N:22]=[C:21](S(C)(=O)=O)[N:20]=2)=[CH:10][CH:9]=1)=[O:6].[CH3:38][OH:39]>CS(C)=O.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:29]=[C... | CO | CS(=O)(=O)c1nccc(Oc2ccc(NC(=O)c3cc(F)cc(N4CCOCC4)c3)c3ccccc23)n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | ClCCl | null | null | null | null | null | null | null | null | null | null | null | A mixture of 3-fluoro-N-(4-{[2-(methylsulfonyl)pyrimidin-4-yl]oxy}-1-naphthyl)-5-morpholin-4-ylbenzamide (0.1 mmol) and methanol (1.0 ml) in DMSO (0.5 ml) is heated using a microwave source at 180° C. for 5 min. The resulting mixture is diluted with CH2Cl2 (5 ml), washed with water, dried over Na2SO4 and concentrated. ... | COc1nccc(Oc2ccc(NC(=O)c3cc(F)cc(N4CCOCC4)c3)c3ccccc23)n1 | null | null | null |
1,422,731 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | [C:1]([O:5][C:6](=[O:38])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:37])[CH2:23][N:24]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:25][C:26]([O:28]C)=[O:27])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1>[C:1]([O:5][C:6]... | COC(=O)CN(CC(=O)NCCCCCCCCCCCCCCC(=O)OC(C)(C)C)C(=O)OC(C)(C)C | null | null | [Na+] | [OH-] | 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 | 16 | 15-[2-(tert-Butoxycarbonyl methoxycarbonylmethyl amino)acetylamino]pentadecanoic acid tert-butyl ester (0.22 g, 0.405 mmol) was dissolved in THF (5 mL) and 1 N NaOH (0.405 mL) was added. The mixture was stirred under nitrogen for 16 h. The mixture was concentrated under vacuum. The residue was suspended in AcOEt (ca 25... | CC(C)(C)OC(=O)CCCCCCCCCCCCCCNC(=O)CN(CC(=O)O)C(=O)OC(C)(C)C | null | null | null |
888,177 | ord_dataset-d728a2f811c0424cbcdb5a84d02b93ae | null | 2009-01-01T00:06:00 | true | C[C@H]1CO[C@@]2([O:9][C@H]3C[C@H]4[C@@H]5CC=C6C[C@@H](O)CC[C@]6(C)[C@H]5CC[C@]4(C)[C@H]3[C@@H]2C)CC1.[OH-].[K+].[CH2:33]([O:37][CH2:38][CH2:39][CH2:40]CCCCCCCCC)[CH:34]1[O:36][CH2:35]1>C1(C)C=CC=CC=1>[CH2:38]([O:37][CH2:33][CH:34]1[O:36][CH2:35]1)[CH:39]1[O:9][CH2:40]1 | C[C@@H]1CC[C@@]2(OC1)O[C@H]1C[C@H]3[C@@H]4CC=C5C[C@@H](O)CC[C@]5(C)[C@H]4CC[C@]3(C)[C@H]1[C@@H]2C | CCCCCCCCCCCCOCC1CO1 | null | [K+] | [OH-] | 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 | 60 | 1 | In a 250 mL, round bottom 3-neck flask equipped with a condenser, a nitrogen in/out let, a mechanical stirrer, a thermo-watch, and a heating mantle, a mixture of 30 g of 10,000 Mw PEG and toluene (80 mL) was heated to 60° C. At this temperature, KOH (1.52 g, 0.04 mol, in 1.5 g of water) was added and the reaction mixtu... | C(OCC1CO1)C1CO1 | null | null | null |
409,174 | ord_dataset-324fb6fdc2414cb79e436bf5d04d4bd2 | null | 1998-01-01T00:08:00 | true | [C:1]([CH:3]([CH3:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[CH:10]([C:12]([CH3:14])=[O:13])=[CH2:11]>C1(C)C=CC=CC=1>[O:13]=[C:12]([CH3:14])[CH2:10][CH2:11][C:3]([C:1]#[N:2])([CH3:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5] | C=CC(C)=O | CCOC(=O)C(C)C#N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 127 mg (1.0 mmol) of ethyl 2-cyanopropanoate, 0.12 ml (1.5 mmol) of methyl vinyl ketone, and 9.4 mg (0.01 mmol) of Rh(acac)(CO)(L) obtained in Example 8 was stirred in 5 ml of toluene at 0° C. for 13 hours. The reaction mixture was concentrated to yield 170 mg (86%) of ethyl 5-oxo-2-cyano-2-methylhexanoate... | CCOC(=O)C(C)(C#N)CCC(C)=O | null | 86.2 | null |
1,323,218 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=1)[NH:7][N:6]=[C:5]2[CH:14]1[CH2:19][CH2:18][N:17]([S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])[CH2:16][CH2:15]1.[OH:25][CH2:26][C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[CH:31][CH:32]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=... | CCS(=O)(=O)N1CCC(c2n[nH]c3c(C(N)=O)cc(Br)cc23)CC1 | OCc1cccc(B(O)O)c1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | Following the general procedure of Example 65, a mixture of 5-bromo-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indazole-7-carboxamide (Intermediate 13) (180 mg, 0.4337 mmols), [3-(hydroxymethyl)phenyl]boronic acid (264 mg, 1.74 mmols), cesium carbonate (282 mg, 0.868 mmol), and Pd(PPh3)4 (22 mg, 0.021 mmol) in dioxane/wate... | CCS(=O)(=O)N1CCC(c2n[nH]c3c(C(N)=O)cc(-c4cccc(CO)c4)cc23)CC1 | null | 67.7 | null |
423,956 | ord_dataset-1a231de00bfe4443b547e1f03885ed41 | null | 1999-01-01T00:01:00 | true | [CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[C:18]([C:23]([O:25]C(C)(C)C)=[O:24])=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:13][CH:12]=2)[C:8]2[CH:30]=[C:31]([Cl:35])[C:32]([Cl:34])=[CH:33][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4].FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]... | CCCCc1nc2cc(Cl)c(Cl)cc2n1Cc1ccc(-c2ccccc2C(=O)OC(C)(C)C)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | Prepared in analogous manner to Example 9 from tert.butyl 4'-[(2-n-butyl-5,6-dichloro-benzimidazol-1-yl)-methyl]biphenyl-2-carboxylate and trifluoroacetic acid in methylene chloride. | CCCCc1nc2cc(Cl)c(Cl)cc2n1Cc1ccc(-c2ccccc2C(=O)O)cc1 | null | null | null |
640,919 | ord_dataset-1c0bae7388cf460091d56129e95b3145 | null | 2004-01-01T00:06:00 | true | [O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:3]1.C(OC(=O)C)(=O)C>[Pd]>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][CH:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:3]1 | CCOC(=O)c1cc(=O)c2ccccc2o1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)OC(C)=O | null | null | null | null | null | null | null | null | null | null | 60 | null | A hydrogenator was charged by adding 6 g of ethyl 4-oxochromene-2-carboxylate, 3.5 mL of acetic anhydride, 1 g of 10% palladium on carbon, 4.0 g of dried 3A molecular sieves (powered), and 30 mL of glacial acetic acid. After purging several times with nitrogen, the hydrogenator was purged several times with hydrogen. W... | CCOC(=O)C1CC(=O)c2ccccc2O1 | null | null | null |
1,113,834 | ord_dataset-4226e9b4f9f845db967ed997270dcafc | null | 2011-01-01T00:12:00 | true | [Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([CH2:12][C:13]([NH:15][NH2:16])=[O:14])=[CH:7][CH:6]=2.[N:17]#[C:18]Br>CO.O>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([CH2:12][C:13]1[O:14][C:18]([NH2:17])=[N:16][N:15]=1)=[CH:7][CH:6]=2 | NNC(=O)Cc1ccc2ncc(Br)cc2c1 | N#CBr | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | O | null | null | null | null | null | null | null | null | null | null | null | A mixture of (3-bromo-quinolin-6-yl)-acetic acid hydrazide (prepared according to procedure described herein) (4.12 g, 14.7 mmol), cyanogen bromide (1.1 eq., 16.2 mmol, 1.7 g) and KHCO3 (1.25 eq., 18.3 mmol, 1.83 g) was stirred in methanol (30 mL) at ambient temperature for 18 hours. The was then diluted with water (40... | Nc1nnc(Cc2ccc3ncc(Br)cc3c2)o1 | null | null | null |
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