Hydrochloric Acid → 1-{4-[1-(4-methoxyphenyl)-7-oxo-3-(trifluoromethyl)-1,4,5,7-tetrahydro-6H-pyrazolo[3,4-c]pyridin-6-yl]phenyl}cyclobutane carboxylic acid

HRID 971135ノート

反応式

HRID 971135 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]3[C:14](=[O:18])[NH:15][CH2:16][CH2:17][C:12]=3[C:11]([C:19]([F:22])([F:21])[F:20])=[N:10]2)=[CH:5][CH:4]=1.[C:23]([O-:26])([O-])=[O:24].[K+].[K+].N1[C:42]2[C:33](=[CH:34][CH:35]=[C:36]3[C:41]=2N=[CH:39][CH:38]=[CH:37]3)C=CC=1.Cl.[CH3:44]S(C)=O>[Cu]I.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[C:13]3[C:14](=[O:18])[N:15]([C:33]4[CH:34]=[CH:35][C:36]([C:37]5([C:23]([OH:26])=[O:24])[CH2:38][CH2:39][CH2:44]5)=[CH:41][CH:42]=4)[CH2:16][CH2:17][C:12]=3[C:11]([C:19]([F:22])([F:20])[F:21])=[N:10]2)=[CH:7][CH:8]=1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 13181,10-PhenanthrolineHCID 11430Potassium CarbonateHCID 218914731-(4-Methoxy-phenyl)-3-trifluoromethyl-1,4,5,6-tetrahydro-pyrazolo[3,4-c]pyridin-7-one

生成物 1

HCID 695157611-{4-[1-(4-methoxyphenyl)-7-oxo-3-(trifluoromethyl)-1,4,5,7-tetrahydro-6H-pyrazolo[3,4-c]pyridin-6-yl]phenyl}cyclobutane carboxylic acid収率 97%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
130 °C

実験手順

Part C. The product from part B (1.20 g, 3.97 mmol) and 1-(4-methoxyphenyl)-3-(trifluoromethyl)-1,4,5,6-tetrahydro-7H-pyrazolo[3,4-c]pyridin-7-one (0.87 g, 2.8 mmol) were stirred in DMSO (3 mL) under N2. K2CO3 (1.16 g, mmol, 3.0 eq) was added followed by the addition of 1,10-phenanthroline (100 mg, 20 mol %) and CuI (106 mg, 20 mol %). The resulting mixture was stirred at 130° C. overnight. LC-MS showed completion of the reaction. EtOAc was added to the cooled solution. The solution was acidified with 1N HCl, and the organic layer was washed with H2O and and brine, dried over MgSO4, filtered, and concentrated to afford 1-{4-[1-(4-methoxyphenyl)-7-oxo-3-(trifluoromethyl)-1,4,5,7-tetrahydro-6H-pyrazolo[3,4-c]pyridin-6-yl]phenyl}cyclobutane carboxylic acid (1.34 g, yield 97%). LC/MS (ESI+) 486.6 (M+H)+, tR=2.81 min (10–90% CH3CN/H2O in a 4-min run).

後処理

  1. customcompletion of the reaction
  2. washthe organic layer was washed with H2O and and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-7c8d284e0252441194b3e3af414f671f
出典データセット
uspto-grants-2007_12
特許番号
US07312214B2

反応ノート

読み込み中…