Hydrochloric Acid → HCID 71259325, compound

HRID 1524404Notes

Reaction equation

HRID 1524404 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]=[CH:24][C:23](C(F)(F)F)=[CH:22][C:21]=3[C:30]3[N:34]([CH3:35])[N:33]=[CH:32][CH:31]=3)=[CH:15][N:16]2[CH3:19])=[CH:12][CH:11]=1)(=[O:9])=[O:8].[ClH:47]>CO>[Cl:47][C:23]1[CH:24]=[CH:25][C:20]([C:14]2[C:13]3[C:17](=[CH:18][C:10]([S:7]([NH:6][C:36]4[S:40][N:39]=[CH:38][N:37]=4)(=[O:8])=[O:9])=[CH:11][CH:12]=3)[N:16]([CH3:19])[CH:15]=2)=[C:21]([C:30]2[N:34]([CH3:35])[N:33]=[CH:32][CH:31]=2)[CH:22]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71259623HCID 71259623, compound

Product 1

HCID 71259325HCID 71259325, compoundYield 44.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 10-mL round-bottom flask was charged with N-(2,4-dimethoxybenzyl)-1-methyl-3-(2-(1-methyl-1H-pyrazol-5-yl)-4-(trifluoromethyl)phenyl)-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamide (35.79 mg, 0.056 mmol) and methanol (1 mL). Hydrogen chloride (4M in 1,4-dioxane) (141 μl, 0.563 mmol) was added, and the resulting solution was stirred for 45 min. The reaction mixture was loaded onto a 500 mg SCX-2 ion exchange column (Silicycle, Quebec City, Canada). The column was eluted with methanol, then with a solution of 2N ammonia in methanol. The basic fractions were combined and concentrated. The residue was purified further by chromatography on silica gel (0 to 10% MeOH/DCM) to give 3-(4-chloro-2-(1-methyl-1H-pyrazol-5-yl)phenyl)-1-methyl-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamide (12.05 mg, 0.025 mmol, 44.1% yield) as a cream colored solid. 1H NMR (400 MHz, DMSO-d6) δ=8.35 (br. s., 1 H), 7.90 (d, J=1.1 Hz, 1 H), 7.62 (d, J=1.3 Hz, 2 H), 7.56-7.31 (m, 4 H), 7.12 (s, 1 H), 6.27 (d, J=1.9 Hz, 1 H), 3.79 (s, 3 H), 3.23 (s, 3 H). m/z (ESI) 485.1 (M+H)+.

Workup

  1. washThe column was eluted with methanol
  2. concentrationconcentrated
  3. customThe residue was purified further by chromatography on silica gel (0 to 10% MeOH/DCM)

Sources & evidence

ORD record
ord-ceb9e8618b624f67b8659c83240be8e9
Source dataset
uspto-grants-2015_07
Patent number
US09079902B2

Reaction notes

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