Trifluoroacetic acid → 1-(2-(pyridin-4-yl)-4-(trifluoromethyl)phenyl)-N-(1,2,4-thiadiazol-5-yl)isoquinoline-6-sulfonamide

HRID 1473321Notes

Reaction equation

HRID 1473321 reaction equation
COC1C=CC(C[N:8]([C:38]2[S:42][N:41]=[CH:40][N:39]=2)[S:9]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[C:18]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][C:23]=2[C:32]2[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=2)=[N:17][CH:16]=[CH:15]3)(=[O:11])=[O:10])=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:35]1[CH:34]=[CH:33][C:32]([C:23]2[CH:24]=[C:25]([C:28]([F:30])([F:29])[F:31])[CH:26]=[CH:27][C:22]=2[C:18]2[C:19]3[C:14](=[CH:13][C:12]([S:9]([NH:8][C:38]4[S:42][N:41]=[CH:40][N:39]=4)(=[O:11])=[O:10])=[CH:21][CH:20]=3)[CH:15]=[CH:16][N:17]=2)=[CH:37][CH:36]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86687374N-(4-methoxybenzyl)-1-(2-(pyridin-4-yl)-4-(trifluoromethyl)phenyl)-N-(1,2,4-thiadiazol-5-yl)isoquinoline-6-sulfonamide

Product 1

HCID 715862281-(2-(pyridin-4-yl)-4-(trifluoromethyl)phenyl)-N-(1,2,4-thiadiazol-5-yl)isoquinoline-6-sulfonamideYield 7.65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(4-methoxybenzyl)-1-(2-(pyridin-4-yl)-4-(trifluoromethyl)phenyl)-N-(1,2,4-thiadiazol-5-yl)isoquinoline-6-sulfonamide (100 mg, 0.158 mmol) in DCM (1578 μl) was added TFA (60.8 μl, 0.789 mmol). The reaction mixture was stirred at room temperature. After 2 hours, LC/MS showed mainly product. Purification was done using a Phenomenex Gemini 5 μm, C18, 110 Å, 150×30 mm column with 0.1% TFA in ACN and water as mobile phase to afford 1-(2-(pyridin-4-yl)-4-(trifluoromethyl)phenyl)-N-(1,2,4-thiadiazol-5-yl)isoquinoline-6-sulfonamide (6.2 mg, 0.012 mmol, 7.65%). MS (ESI): 514.0 [M+H]+; 1H NMR (500 MHz, DMSO-d6) δ ppm 7.19-7.22 (m, 2H), 7.80 (s, 2H), 7.85 (d, J=8.01 Hz, 1H), 8.01-8.06 (m, 2H), 8.11 (d, J=5.77 Hz, 1H), 8.37 (br. s., 2H), 8.47 (s, 1H), 8.54 (s, 1H), 8.61 (d, J=5.66 Hz, 1H).

Workup

  1. customPurification

Sources & evidence

ORD record
ord-523603285ca74deba988c096cc7dafb1
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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