Hydrogen Bromide → HCID 178442451, compound

HRID 425424Notes

Reaction equation

HRID 425424 reaction equation
Br.C(OC(=O)[NH:11][C:12]([C:28]1[NH:29][CH:30]=[C:31]([CH2:33][C:34]([CH3:38])([CH3:37])[CH2:35][CH3:36])[N:32]=1)([CH3:27])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][N:21]=2)=[CH:16][CH:15]=1)C1C=CC=CC=1>C(Cl)Cl>[CH3:37][C:34]([CH3:38])([CH2:35][CH3:36])[CH2:33][C:31]1[N:32]=[C:28]([C:12]([NH2:11])([CH3:27])[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][N:21]=3)=[CH:16][CH:15]=2)[NH:29][CH:30]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 178442445HCID 178442445, compound

Product 1

HCID 178442451HCID 178442451, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Hydrogen bromide (37 wt % in acetic acid) (1 mL) was added to a solution of benzyl{1-[4-(2,2-dimethylbutyl)-1H-imidazol-2-yl]-2-[4-(5-fluoropyridin-2-yl)phenyl]-1-methylethyl}carbamate (Example 58) (10 mg, 0.02 mmol) in methylene chloride (0.5 mL). After stirring at ambient temperature for 1 h, volatiles were removed in vacuo, azeotroping with toluene. The residue was diluted with 1 N aqueous sodium hydroxide and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (sodium sulfate) and concentrated in vacuo to afford the title compound. (M+H) found: 381.

Workup

  1. customvolatiles were removed in vacuo
  2. customazeotroping with toluene
  3. additionThe residue was diluted with 1 N aqueous sodium hydroxide
  4. extractionextracted with ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8a42a5169d624156ad82a6421ac9e141
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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