Hydrochloric Acid → HCID 59698850, compound

HRID 2237527Notes

Reaction equation

HRID 2237527 reaction equation
C([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([CH2:24][C:25]2[N:26]=[C:27]([NH:30][C:31](=[O:39])[C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=3)[S:28][CH:29]=2)=[O:23])=[C:17]([F:40])[CH:16]=1)(=[O:8])=[O:7])(C)(C)C.Cl>C(Cl)(Cl)Cl.CO>[Cl:38][C:35]1[CH:34]=[CH:33][C:32]([C:31]([NH:30][C:27]2[S:28][CH:29]=[C:25]([CH2:24][C:22](=[O:23])[NH:21][C:18]3[CH:19]=[CH:20][C:15]([C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=4[S:6](=[O:7])(=[O:8])[NH2:5])=[CH:16][C:17]=3[F:40])[N:26]=2)=[O:39])=[CH:37][CH:36]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59698892N-{4-[(2'-tert-butylsulfamoyl-3-fluoro-biphenyl-4-ylcarbamoyl)-methyl]-thiazol-2-yl}-4-chloro-benzamide

Product 1

HCID 59698850HCID 59698850, compoundYield 75.8%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

A solution of 163 mg N-{4-[(2′-tert-butylsulfamoyl-3-fluoro-biphenyl-4-ylcarbamoyl)-methyl]-thiazol-2-yl}-4-chloro-benzamide in 8 ml CHCl3/MeOH 3:1 was cooled to −11° C. A stream of HCl gas was passed over the stirred solution for 10 min. The reaction mixture was kept at 4° C. over night, then concentrated. The crude product was purified by chromatography on silica using a gradient from CH2Cl2 to CH2Cl2/MeOH 9:1 in 20 minutes to give 112 mg 4-chloro-N-{4-[(3-fluoro-2′-sulfamoyl-biphenyl-4-ylcarbamoyl)-methyl]-thiazol-2-yl}-benzamide as white solid. MS 545.3 ([M+H]+)

Workup

  1. waitThe reaction mixture was kept at 4° C. over night
  2. concentrationconcentrated
  3. customThe crude product was purified by chromatography on silica using a gradient from CH2Cl2 to CH2Cl2/MeOH 9:1 in 20 minutes

Sources & evidence

ORD record
ord-8399a12751814b1baa9d7c72014e8d0e
Source dataset
uspto-grants-2010_05
Patent number
US07718659B2

Reaction notes

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