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

HRID 1524416Notes

Reaction equation

HRID 1524416 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[C:12]1[C:20]2[C:15](=[CH:16][C:17]([S:21]([N:24](CC3C=CC(OC)=CC=3OC)[C:25]3[S:29][N:28]=[CH:27][N:26]=3)(=[O:23])=[O:22])=[CH:18][CH:19]=2)[N:14]([CH3:41])[CH:13]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:10])([F:9])[F:11])[CH:5]=[CH:4][C:3]=1[C:12]1[C:20]2[C:15](=[CH:16][C:17]([S:21]([NH:24][C:25]3[S:29][N:28]=[CH:27][N:26]=3)(=[O:23])=[O:22])=[CH:18][CH:19]=2)[N:14]([CH3:41])[CH:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71259332HCID 71259332, compound

Product 1

HCID 712639263-(2-chloro-4-(trifluoromethyl)phenyl)-1-methyl-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamideYield 105.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(2-chloro-4-(trifluoromethyl)phenyl)-N-(2,4-dimethoxybenzyl)-1-methyl-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamide (0.020 g, 0.032 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. The reaction was concentrated, dissolved in acetonitrile, and passed through a PEAX ion exchange column. 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 3-(2-chloro-4-(trifluoromethyl)phenyl)-1-methyl-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamide (0.016 g) as a tan solid. (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ=8.43 (s, 7 H), 8.03 (s, 1 H), 8.01-7.97 (m, 2 H), 7.79 (d, J=1.1 Hz, 2 H), 7.67 (d, J=8.6 Hz, 4 H), 7.55 (dd, J=1.7, 8.5 Hz, 1 H), 3.98 (s, 3 H). m/z (ESI) 473.1 (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-e679369d7a204b0384f4684bb68b320f
Source dataset
uspto-grants-2015_07
Patent number
US09079902B2

Reaction notes

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