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 971135노트

반응식

HRID 971135 반응식
[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

참가 물질

8

반응물 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

생성물 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 acid수율 97%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8857Ethyl Acetate용매

반응 조건

온도
130 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7c8d284e0252441194b3e3af414f671f
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07312214B2

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