Trifluoroacetic acid → HCID 86687713, compound

HRID 1473641Notes

Reaction equation

HRID 1473641 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[C:13]1[C:22]2[C:17](=[CH:18][C:19]([S:23]([N:26](CC3C=CC(OC)=CC=3)[C:27]3[N:28]=[CH:29][S:30][CH:31]=3)(=[O:25])=[O:24])=[CH:20][CH:21]=2)[CH:16]=[CH:15][N:14]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:6]=[CH:5][C:4]=1[C:13]1[C:22]2[C:17](=[CH:18][C:19]([S:23]([NH:26][C:27]3[N:28]=[CH:29][S:30][CH:31]=3)(=[O:25])=[O:24])=[CH:20][CH:21]=2)[CH:16]=[CH:15][N:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86687712HCID 86687712, compound

Product 1

HCID 86687713HCID 86687713, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(2-methoxy-4-(trifluoromethyl)phenyl)-N-(4-methoxybenzyl)-N-(thiazol-4-yl)isoquinoline-6-sulfonamide (0.070 g, 0.120 mmol) in DCM (1.195 ml) was added TFA (0.276 ml, 3.59 mmol) at room temperature. The resulting mixture stirred for a total of 3 weeks, monitoring every few days by LCMS. The crude mixture was concentrated by allowing the DCM to evaporate and taken up in DMSO. The DMSO solution was injected directly onto the Gilson HPLC for purification to provide 24 mgs (43% yield) of desired product. m/z (ESI) 465.9 (M+H)+.

Workup

  1. waitmonitoring every few days by LCMS
  2. concentrationThe crude mixture was concentrated
  3. customto evaporate
  4. customThe DMSO solution was injected directly onto the Gilson HPLC for purification

Sources & evidence

ORD record
ord-1dcda931d92c44c1a1af4b208019e75b
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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