Trifluoroacetic acid → 1-amino-N-(2-methyl-5-(3-(trifluoromethyl)benzamido)phenyl)isoquinoline-5-carboxamide

HRID 1051251ノート

反応式

HRID 1051251 の反応式
C([NH:5][C:6]1[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([C:16]([NH:18][C:19]3[CH:24]=[C:23]([NH:25][C:26](=[O:37])[C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=4)[CH:22]=[CH:21][C:20]=3[CH3:38])=[O:17])[C:10]=2[CH:9]=[CH:8][N:7]=1)(C)(C)C.C(O)(C(F)(F)F)=O.C(=O)(O)[O-].[Na+]>O1CCCC1.C(OCC)(=O)C>[NH2:5][C:6]1[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([C:16]([NH:18][C:19]3[CH:24]=[C:23]([NH:25][C:26](=[O:37])[C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:35])([F:34])[F:36])[CH:28]=4)[CH:22]=[CH:21][C:20]=3[CH3:38])=[O:17])[C:10]=2[CH:9]=[CH:8][N:7]=1

参加物

6

反応物 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 1180908921-(t-butylamino)-N-(2-methyl-5-(3-(trifluoromethyl)benzamido)phenyl)isoquinoline-5-carboxamide

生成物 1

HCID 1180907921-amino-N-(2-methyl-5-(3-(trifluoromethyl)benzamido)phenyl)isoquinoline-5-carboxamide収率 8.6%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

1-(t-Butylamino)-N-(2-methyl-5-(3-(trifluoromethyl)benzamido)phenyl)isoquinoline-5-carboxamide (0.13 g, 0.25 mmol) obtained in Step (3) above was dissolved in tetrahydrofuran (1 mL), slowly added with TFA (3 mL) at 0° C., and stirred for about 4 hours at 70° C. The reaction mixture was cooled to room temperature, and adjusted to have a pH value in a range of 10˜11 by adding a saturated aqueous sodium bicarbonate solution. The reaction mixture was diluted with ethyl acetate, followed by washing with distilled water. The organic layer thus obtained was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The concentrated compound was purified using silica gel chromatography to obtain the title compound (10 mg, 8%).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washby washing with distilled water
  3. customThe organic layer thus obtained
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe concentrated compound was purified

出典と根拠

ORDレコード
ord-64080db45b25424e9eb0775733e99ba7
出典データセット
uspto-grants-2016_07
特許番号
US09388165B2

反応ノート

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