Hydrochloric Acid → 2-[6-(4-Iodo-phenyl)-7-oxo-3-trifluoromethyl-4,5,6,7-tetrahydro-pyrazolo[3,4-c]pyridin-1-yl]-5-methoxy-benzoic acid

HRID 130493

反応式

HRID 130493 の反応式
C[O:2][C:3](=[O:33])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[N:12]1[C:16]2[C:17](=[O:28])[N:18]([C:21]3[CH:26]=[CH:25][C:24]([I:27])=[CH:23][CH:22]=3)[CH2:19][CH2:20][C:15]=2[C:14]([C:29]([F:32])([F:31])[F:30])=[N:13]1.[OH-].[Na+].Cl>O1CCCC1>[I:27][C:24]1[CH:23]=[CH:22][C:21]([N:18]2[CH2:19][CH2:20][C:15]3[C:14]([C:29]([F:30])([F:32])[F:31])=[N:13][N:12]([C:5]4[CH:6]=[CH:7][C:8]([O:10][CH3:11])=[CH:9][C:4]=4[C:3]([NH:12][C:16]4[CH:17]=[N:18][CH:19]=[CH:20][CH:15]=4)=[O:33])[C:16]=3[C:17]2=[O:28])=[CH:26][CH:25]=1.[I:27][C:24]1[CH:25]=[CH:26][C:21]([N:18]2[CH2:19][CH2:20][C:15]3[C:14]([C:29]([F:31])([F:32])[F:30])=[N:13][N:12]([C:5]4[CH:6]=[CH:7][C:8]([O:10][CH3:11])=[CH:9][C:4]=4[C:3]([OH:33])=[O:2])[C:16]=3[C:17]2=[O:28])=[CH:22][CH:23]=1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 693099032-[6-(4-Iodo-phenyl)-7-oxo-3-trifluoromethyl-4,5,6,7-tetrahydro-pyrazolo[3,4-c]pyridin-1-yl]-5-methoxy-benzoic acid methyl ester

生成物 2

HCID 586302342-[6-(4-Iodo-phenyl)-7-oxo-3-trifluoromethyl-4,5,6,7-tetrahydro-pyrazolo[3,4-c]pyridin-1-yl]-5-methoxy-N-pyridin-3-yl-benzamideHCID 693098972-[6-(4-Iodo-phenyl)-7-oxo-3-trifluoromethyl-4,5,6,7-tetrahydro-pyrazolo[3,4-c]pyridin-1-yl]-5-methoxy-benzoic acid収率 100%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

The title compound was prepared from 2-[6-(4-iodo-phenyl)-7-oxo-3-trifluoromethyl-4,5,6,7-tetrahydro-pyrazolo[3,4-c]pyridin-1-yl]-5-methoxy-benzoic acid methyl ester as obtained in Example 1. The ester (270 mg, 0.47 mmol) was stirred in tetrahydrofuran (1 mL) and 10% sodium hydroxide (1 mL) for 5 h. The reaction was acidified with 1N hydrochloric acid to pH 3 and extracted with ethyl acetate (3×5 mL). The combined extracts were washed with water (2×5 mL), dried over sodium sulfate, filtered, and evaporated to give 2-[6-(4-iodo-phenyl)-7-oxo-3-trifluoromethyl-4,5,6,7-tetrahydro-pyrazolo[3,4-c]pyridin-1-yl]-5-methoxy-benzoic acid (263 mg, 100%) as a colorless solid. The acid (263 mg, 0.47 mmol) was dissolved in dimethylformamide (3 mL) to which were added triethylamine (233 mL, 1.68 mmol) and 3-aminopyridine (54 mg, 0.58 mmol). After 10 minutes benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP reagent) was added and stirring continued for 24 hr. The reaction was poured into ethyl acetate/water, and the phases were separated. The aqueous was extracted twice with ethyl acetate. The combined organics were washed with water (4×) and once with brine, dried over sodium sulfate, filtered, and evaporated to give 278 mg (91%) of a light orange colored solid. The material was purified by preparative HPLC to give the title compound as a colorless solid. MS (ES+) 634.0 (M+H)+(100%).

後処理

  1. customas obtained in Example 1
  2. extractionextracted with ethyl acetate (3×5 mL)
  3. washThe combined extracts were washed with water (2×5 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

出典と根拠

ORDレコード
ord-3bef702e3a244f0abd97924961851527
出典データセット
uspto-grants-2008_06
特許番号
US07381732B2

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