Trifluoroacetic acid → 1-(2-bromo-4-(trifluoromethyl)phenyl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide

HRID 1473463Notes

Reaction equation

HRID 1473463 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[C:12]1[C:21]2[C:16](=[CH:17][C:18]([S:22]([N:25](CC3C=CC(OC)=CC=3OC)[C:26]3[S:27][CH:28]=[CH:29][N:30]=3)(=[O:24])=[O:23])=[CH:19][CH:20]=2)[CH:15]=[CH:14][N:13]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:9])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[C:12]1[C:21]2[C:16](=[CH:17][C:18]([S:22]([NH:25][C:26]3[S:27][CH:28]=[CH:29][N:30]=3)(=[O:24])=[O:23])=[CH:19][CH:20]=2)[CH:15]=[CH:14][N:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 866873791-(2-bromo-4-(trifluoromethyl)phenyl)-N-(2,4-dimethoxybenzyl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide

Product 1

HCID 866875101-(2-bromo-4-(trifluoromethyl)phenyl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(2-bromo-4-(trifluoromethyl)phenyl)-N-(2,4-dimethoxybenzyl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide (see Example 70, step 3; 0.100 g, 0.150 mmol) was dissolved in DCM (1 mL). TFA (0.1 mL, 1.298 mmol) was added and the reaction was stirred for 30 minutes. The reaction was concentrated and the material was purified via silica gel column chromatography (12 g, gradient elution 0 to 10% MeOH:DCM) to afford 1-(2-bromo-4-(trifluoromethyl)phenyl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm=12.92 (br. s., 1H), 8.74 (d, J=5.8 Hz, 1H), 8.62 (d, J=1.4 Hz, 1H), 8.31-8.18 (m, 2H), 7.97 (d, J=7.9 Hz, 1H), 7.91 (dd, J=1.7, 8.9 Hz, 1H), 7.76 (d, J=7.9 Hz, 1H), 7.65 (d, J=8.8 Hz, 1H), 7.29 (d, J=4.3 Hz, 1H), 6.88 (d, J=4.5 Hz, 1H). m/z (ESI) 514.0 (M+H)+.

Workup

  1. concentrationThe reaction was concentrated
  2. customthe material was purified via silica gel column chromatography (12 g, gradient elution 0 to 10% MeOH:DCM)

Sources & evidence

ORD record
ord-a91ebad8a64e41c8a401f45328e39675
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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