Hydrochloric Acid → 4-[2-(5-amino-1H-pyrazol-4-yl)-4-chlorophenoxy]-3-cyano-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide

HRID 46242Notes

Reaction equation

C([N:5]1[C:9]([NH:10]C(=O)C(F)(F)F)=[C:8]([C:17]2[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=2[O:24][C:25]2[CH:30]=[CH:29][C:28]([S:31]([N:34](CC3C=CC(OC)=CC=3OC)[C:35]3[S:39][N:38]=[CH:37][N:36]=3)(=[O:33])=[O:32])=[CH:27][C:26]=2[C:51]#[N:52])[CH:7]=[N:6]1)(C)(C)C.Cl>CO>[NH2:10][C:9]1[NH:5][N:6]=[CH:7][C:8]=1[C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=1[O:24][C:25]1[CH:30]=[CH:29][C:28]([S:31]([NH:34][C:35]2[S:39][N:38]=[CH:37][N:36]=2)(=[O:32])=[O:33])=[CH:27][C:26]=1[C:51]#[N:52]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of the N-{1-tert-butyl-4-[5-chloro-2-(2-cyano-4-{[(2,4-dimethoxybenzyl)(1,2,4-thiadiazol-5-yl)amino]sulfonyl}phenoxy)phenyl]-1H-pyrazol-5-yl}-2,2,2-trifluoroacetamide (Preparation 419, 157 mg, 0.20 mmol) in methanol (15 ml) was added hydrogen chloride (4 M in 1,4-dioxane, 3 ml). The resulting yellow solution was stirred and heated at 60° C. for 48 hours. The solvent removed in vacuo to afford a pale yellow residue. The material was purified by column chromatography (80 g silica gel column) eluting with methanol:dichloromethane (5:95, by volume) to afford the title compound as a yellow oily solid, 56 mg, 59% yield.

Workup

customThe solvent removed in vacuo
customto afford a pale yellow residue
customThe material was purified by column chromatography (80 g silica gel column)
washeluting with methanol:dichloromethane (5:95, by volume)

Sources & evidence

ORD record: ord-1008afe1577446e39251d39698e464e3
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541588B2

Reaction notes

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