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

HRID 971137노트

반응식

HRID 971137 반응식
I[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:12]2[CH2:14]C2)[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[C:27]3[C:28](=[O:32])[NH:29][CH2:30][CH2:31][C:26]=3[C:25]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[N:24]2)=[CH:19][CH:18]=1.C([O-])([O-])=O.[K+].[K+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.Cl>CS(C)=O.[Cu]I.CCOC(C)=O>[CH2:36]([O:35][C:33]([C:25]1[C:26]2[CH2:31][CH2:30][N:29]([C:2]3[CH:3]=[CH:4][C:5]([C:8]4([C:9]([OH:11])=[O:10])[CH2:12][CH2:14]4)=[CH:6][CH:7]=3)[C:28](=[O:32])[C:27]=2[N:23]([C:20]2[CH:19]=[CH:18][C:17]([O:16][CH3:15])=[CH:22][CH:21]=2)[N:24]=1)=[O:34])[CH3:37]

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 13181,10-PhenanthrolineHCID 11430Potassium CarbonateHCID 22240468Ethyl 1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo(3,4-c)pyridine-3-carboxylateHCID 695169744-Iodophenylcyclopropyl acetic acid

생성물 1

HCID 695164601-{4-[3-(ethoxycarbonyl)-1-(4-methoxyphenyl)-7-oxo-1,4,5,7-tetrahydro-6H-pyrazolo[3,4-c]pyridin-6-yl]phenyl}cyclopropanecarboxylic acid수율 72.6%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
110 °C

실험 절차

Part A. 4-Iodophenylcyclopropyl acetic acid (1.93 g, 6.70 mmol) and 1-(4-methoxyphenyl)-3-(ethoxycarbonyl)-1,4,5,6-tetrahydro-7H-pyrazolo[3,4-c]pyridin-7-one (1.41 g, 4.46 mmol) were stirred in DMSO (4 mL) under N2. K2CO3 (1.84 g, 13.33 mmol, 3.0 eq) was added followed by the addition of 1,10-phenanthroline (0.15 g, 20 mol %) and CuI (0.16 g, 20 mol %). The resulting mixture was stirred at 110° C. overnight. LC-MS showed completion of the reaction. EtOAc was added to the cooled solution. It was acidified with 1N HCl, and the organic layer was washed with H2O, and brine, dried over MgSO4, filtered, and concentrated to afford 1-{4-[3-(ethoxycarbonyl)-1-(4-methoxyphenyl)-7-oxo-1,4,5,7-tetrahydro-6H-pyrazolo[3,4-c]pyridin-6-yl]phenyl}cyclopropanecarboxylic acid (1.54 g, yield: 72.6%). LC/MS (ESI+) 476.4 (M+H)+, tR=2.58 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 brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c25e834455b14700a0e4141103f0d2e8
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07312214B2

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