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

HRID 1051251Notes

Reaction equation

HRID 1051251 reaction equation
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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-64080db45b25424e9eb0775733e99ba7
Source dataset
uspto-grants-2016_07
Patent number
US09388165B2

Reaction notes

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