Trifluoroacetic acid → 1-methyl-3-(3-(pyridin-4-yl)-5-(trifluoromethyl)phenyl)-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamide

HRID 1524411Notes

Reaction equation

HRID 1524411 reaction equation
COC1C=C(OC)C=CC=1C[N:6]([C:36]1[S:40][N:39]=[CH:38][N:37]=1)[S:7]([C:10]1[CH:18]=[C:17]2[C:13]([C:14]([C:20]3[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[C:22]([C:30]4[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=4)[CH:21]=3)=[CH:15][N:16]2[CH3:19])=[CH:12][CH:11]=1)(=[O:9])=[O:8].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:19][N:16]1[C:17]2[C:13](=[CH:12][CH:11]=[C:10]([S:7]([NH:6][C:36]3[S:40][N:39]=[CH:38][N:37]=3)(=[O:8])=[O:9])[CH:18]=2)[C:14]([C:20]2[CH:25]=[C:24]([C:26]([F:28])([F:29])[F:27])[CH:23]=[C:22]([C:30]3[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=3)[CH:21]=2)=[CH:15]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71259417N-(2,4-dimethoxybenzyl)-1-methyl-3-(3-(pyridin-4-yl)-5-(trifluoromethyl)phenyl)-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamide

Product 1

HCID 712594861-methyl-3-(3-(pyridin-4-yl)-5-(trifluoromethyl)phenyl)-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamideYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(2,4-dimethoxybenzyl)-1-methyl-3-(3-(pyridin-4-yl)-5-(trifluoromethyl)phenyl)-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamide (0.050 g, 0.075 mmol) was dissolved in 0.5 mL of DCM and TFA (0.5 ml, 6.49 mmol) was added. The reaction was stirred for 15 minutes at room temperature. The reaction was concentrated, dissolved in acetonitrile, and passed through a PEAX ion exchange column (purchased from Biotage, LLC, Charlotte, N.C.). The column was flushed several times with acetonitrile, then the product was liberated by flushing several times with an 1M HCl solution in 15% MeOH/EtOAc. The solution was concentrated to afford 1-methyl-3-(3-(pyridin-4-yl)-5-(trifluoromethyl)phenyl)-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamide (0.029 g, 0.056 mmol, 75% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ=8.94-8.84 (m, 2 H), 8.46 (s, 1 H), 8.41 (s, 1 H), 8.32 (s, 1 H), 8.30 (d, J=6.1 Hz, 2 H), 8.14-8.09 (m, 3 H), 8.05 (d, J=1.3 Hz, 1 H), 7.62 (dd, J=1.6, 8.6 Hz, 1 H), 3.98 (s, 3 H). m/z (ESI). 516.0 (M+H)+.

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutiondissolved in acetonitrile
  3. customThe column was flushed several times with acetonitrile
  4. customby flushing several times with an 1M HCl solution in 15% MeOH/EtOAc
  5. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-bf33eb8a0f2f4fe5b0b2de6aae2b9347
Source dataset
uspto-grants-2015_07
Patent number
US09079902B2

Reaction notes

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