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 971137ノート

反応式

HRID 971137 の反応式
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]

参加物

9

反応物 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

生成物 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 acid収率 72.6%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
110 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c25e834455b14700a0e4141103f0d2e8
出典データセット
uspto-grants-2007_12
特許番号
US07312214B2

反応ノート

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