Trifluoroacetic acid → HCID 86687672, compound

HRID 1473608Notes

Reaction equation

HRID 1473608 reaction equation
[C:1]([CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[C:20]2[C:15](=[CH:16][C:17]([S:21]([N:24](CC3C=CC(OC)=CC=3OC)[C:25]3[S:26][CH:27]=[CH:28][N:29]=3)(=[O:23])=[O:22])=[CH:18][CH:19]=2)[C:14]([F:41])=[CH:13][N:12]=1)#[N:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]([CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[C:20]2[C:15](=[CH:16][C:17]([S:21]([NH:24][C:25]3[S:26][CH:27]=[CH:28][N:29]=3)(=[O:23])=[O:22])=[CH:18][CH:19]=2)[C:14]([F:41])=[CH:13][N:12]=1)#[N:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86687671HCID 86687671, compound

Product 1

HCID 86687672HCID 86687672, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(2-(cyanomethoxy)phenyl)-N-(2,4-dimethoxybenzyl)-4-fluoro-N-(thiazol-2-yl)isoquinoline-6-sulfonamide (0.084 g, 0.141 mmol) was dissolved in DCM and TFA (0.1 mL, 1.298 mmol) was added. The reaction was stirred for 30 minutes at room temperature. The reaction was concentrated and purified via column chromatography (RediSep Gold 12 g, gradient elution 0-10% MeOH:DCM) to afford 1-(2-(cyanomethoxy)phenyl)-4-fluoro-N-(thiazol-2-yl)isoquinoline-6-sulfonamide as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ=13.00 (br. s., 1H), 8.74 (d, J=1.6 Hz, 1H), 8.51 (d, J=1.6 Hz, 1H), 7.98 (dd, J=1.7, 8.9 Hz, 1H), 7.77 (d, J=8.8 Hz, 1H), 7.69-7.59 (m, 1H), 7.48-7.36 (m, 2H), 7.34-7.22 (m, 2H), 6.89 (d, J=4.4 Hz, 1H), 5.09 (s, 2H). m/z (ESI) 441.0 (M+H)+.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified via column chromatography (RediSep Gold 12 g, gradient elution 0-10% MeOH:DCM)

Sources & evidence

ORD record
ord-c89bdd15f6c24537bc63f7b856aac1cf
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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