Trifluoroacetic acid → 8-chloro-2-[(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl]-7-[(1,1,1-trifluoropropan-2-yl)oxy]-3,4-dihydroisoquinolin-1(2H)-one

HRID 577485Notes

Reaction equation

HRID 577485 reaction equation
C([O:8][C:9]1[C:14]([CH2:15][N:16]2[CH2:25][CH2:24][C:23]3[C:18](=[C:19]([Cl:33])[C:20]([O:26][CH:27]([CH3:32])[C:28]([F:31])([F:30])[F:29])=[CH:21][CH:22]=3)[C:17]2=[O:34])=[C:13]([CH3:35])[CH:12]=[C:11]([CH3:36])[N:10]=1)C1C=CC=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:33][C:19]1[C:20]([O:26][CH:27]([CH3:32])[C:28]([F:31])([F:29])[F:30])=[CH:21][CH:22]=[C:23]2[C:18]=1[C:17](=[O:34])[N:16]([CH2:15][C:14]1[C:9](=[O:8])[NH:10][C:11]([CH3:36])=[CH:12][C:13]=1[CH3:35])[CH2:25][CH2:24]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 867237102-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-chloro-7-[(1,1,1-trifluoropropan-2-yl)oxy]-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 867237118-chloro-2-[(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl]-7-[(1,1,1-trifluoropropan-2-yl)oxy]-3,4-dihydroisoquinolin-1(2H)-oneYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-chloro-7-[(1,1,1-trifluoropropan-2-yl)oxy]-3,4-dihydroisoquinolin-1(2H)-one (58b, 70 mg, 0.14 mmol) in CH2Cl2 (5 mL) was added TFA (1 mL) at room temperature. The resulting mixture was stirred at room temperature overnight. The mixture was concentrated under vacuum. The residue was purified by column chromatography (EtOAc) to give the title compound (Example 58, 20 mg, 34%) as a white solid. 1H NMR (400 MHz, chloroform): δ 11.16 (s, 1H), 7.08-7.05 (d, 1H), 7.00-6.98 (d, 1H), 5.94 (s, 1H), 4.75 (s, 2H), 4.57-4.54 (t, 1H), 3.55 (s, 2H), 2.77 (s, 2H), 2.33-2.25 (d, 6H), 1.55 (s, 3H); MS 428.9 [M+H].

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. customThe residue was purified by column chromatography (EtOAc)

Sources & evidence

ORD record
ord-241f7f74e12c497a94a43a71fd175f9b
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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