Hydrogen Bromide → HCID 57513820, compound

HRID 2368406Notes

Reaction equation

HRID 2368406 reaction equation
Br.C(OC(=O)[NH:11][C:12]([C:15](=[O:37])[NH:16][C:17]1[S:18][C:19]([O:29][C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)=[C:20]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[N:21]=1)([CH3:14])[CH3:13])C1C=CC=CC=1>C(O)(=O)C>[NH2:11][C:12]([CH3:14])([CH3:13])[C:15]([NH:16][C:17]1[S:18][C:19]([O:29][C:30]2[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=2)=[C:20]([C:22]2[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=2)[N:21]=1)=[O:37]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 57513819HCID 57513819, compound

Product 1

HCID 57513820HCID 57513820, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

33% HBr (100 mL) was added to a solution of {1-[5-(4-Fluoro-phenoxy)-4-(4-fluoro-phenyl)-thiazol-2-ylcarbamoyl]-1-methyl-ethyl}-carbamic acid benzyl ester (12 g, 23 mmol) in acetic acid (50 mL). The mixture was stirred at room temperature for 18 h. Most of acetic acid was removed by evaporation under vacuum. The mixture was basified with 1M NaOH, and the product was extracted with dichloromethane. The dichloromethane extract was washed with brine, dried over Na2SO4 and concentrated. The residue was chromatographed to give the title compound. m/z 390.9 (MH+).

Workup

  1. customMost of acetic acid was removed by evaporation under vacuum
  2. extractionthe product was extracted with dichloromethane
  3. extractionThe dichloromethane extract
  4. washwas washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was chromatographed

Sources & evidence

ORD record
ord-8f7f5737524741fdaa5c267ccad30093
Source dataset
uspto-grants-2014_04
Patent number
US08703761B2

Reaction notes

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