Dichloromethane → HCID 86687494, compound

HRID 1473448Notes

Reaction equation

HRID 1473448 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:30]2[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][C:31]=2[O:40][CH3:41])[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([S:12]([N:15](CC1C=CC(OC)=CC=1)[C:16]1[S:17][CH:18]=[CH:19][N:20]=1)(=[O:14])=[O:13])=[CH:7][CH:6]=2.C(Cl)Cl.C(O)(C(F)(F)F)=O>CO>[Cl:1][C:2]1[N:3]=[C:4]([C:30]2[CH:35]=[CH:34][C:33]([C:36]([F:37])([F:38])[F:39])=[CH:32][C:31]=2[O:40][CH3:41])[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([S:12]([NH:15][C:16]1[S:17][CH:18]=[CH:19][N:20]=1)(=[O:14])=[O:13])=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 866874313-chloro-1-(2-methoxy-4-(trifluoromethyl)phenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide

Product 1

HCID 86687494HCID 86687494, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A flask was charged with 3-chloro-1-(2-methoxy-4-(trifluoromethyl)phenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide (Intermediate RRR) (58.43 mg, 0.094 mmol), DCM (1 mL), and TFA (0.5 mL) to give a yellow solution (8:45 am). After 30 min of stirring at RT, the mixture was diluted with MeOH and concentrated. The residue was purified by chromatography on silica gel (0-10% MeOH/DCM) to give 47 mg of a light yellow solid. The solid was concentrated from DCM (2×), then taken up in DCM and filtered. The collected solid was washed with DCM (2×), then dried under vacuum for 10 min to give 3-chloro-1-(2-methoxy-4-(trifluoromethyl)phenyl)-n-(thiazol-2-yl)isoquinoline-6-sulfonamide as a white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm=12.95 (s, 1H), 8.57 (d, J=1.8 Hz, 1H), 8.39 (s, 1H), 7.87 (dd, J=1.8, 8.9 Hz, 1H), 7.72 (d, J=8.9 Hz, 1H), 7.61 (d, J=7.7 Hz, 1H), 7.56-7.48 (m, 2H), 7.30 (d, J=4.7 Hz, 1H), 6.90 (d, J=4.6 Hz, 1H), 3.76 (s, 3H). m/z (ESI) 500.2 (M+H)+.

Workup

  1. customto give a yellow solution (8:45 am)
  2. concentrationconcentrated
  3. customThe residue was purified by chromatography on silica gel (0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-8384bcc510034ce7a4bb872b28db5b0c
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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