Trifluoroacetic acid → 1-(4-fluoro-2-hydroxyphenyl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide

HRID 1473435Notes

Reaction equation

HRID 1473435 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([S:18]([N:21](CC4C=CC(OC)=CC=4)[C:22]4[S:23][CH:24]=[CH:25][N:26]=4)(=[O:20])=[O:19])=[CH:15][CH:16]=3)[CH:11]=[CH:10][N:9]=2)=[C:4]([OH:36])[CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([S:18]([NH:21][C:22]4[S:23][CH:24]=[CH:25][N:26]=4)(=[O:19])=[O:20])=[CH:15][CH:16]=3)[CH:11]=[CH:10][N:9]=2)=[C:4]([OH:36])[CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 1364090671-(4-fluoro-2-hydroxyphenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide

Product 1

HCID 1362503551-(4-fluoro-2-hydroxyphenyl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamideYield 22%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(4-fluoro-2-hydroxyphenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide was dissolved in DCM (1 ml) and TFA (1 ml) and stirred at ambient temperature for 2 h. The mixture was purified by reverse phase chromatography, eluting with 0.1% NH4OH in ACN and water as mobile phase to obtain 1-(4-fluoro-2-hydroxyphenyl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide (20 mg, 22%). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.88 (br. s., 1H) 10.19 (s, 1H) 8.65 (d, J=5.67 Hz, 1H) 8.51 (d, J=1.56 Hz, 1H) 8.06 (d, J=5.87 Hz, 1H) 7.78-7.91 (m, 2H) 7.34 (t, J=7.78 Hz, 1H) 7.26 (d, J=4.50 Hz, 1H) 6.76-6.88 (m, 3H). m/z (ESI) 402.0 (M+H)+.

Workup

  1. customThe mixture was purified by reverse phase chromatography
  2. washeluting with 0.1% NH4OH in ACN and water as mobile phase

Sources & evidence

ORD record
ord-740bf6c01cb547da852b6bc455e1e007
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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