Hydrogen Bromide → HCID 178423602, compound

HRID 1596356Notes

Reaction equation

HRID 1596356 reaction equation
C(OC([NH:11][CH:12]1[N:18]=[C:17]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[C:16]2[CH:25]=[CH:26][CH:27]=[C:28]([CH3:29])[C:15]=2[N:14]([CH2:30][C:31]2[N:32]=[CH:33][N:34](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:35]=2)[C:13]1=[O:55])=O)C1C=CC=CC=1.Br.C(OCC)(=O)C>C(O)(=O)C>[NH2:11][CH:12]1[N:18]=[C:17]([CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[C:16]2[CH:25]=[CH:26][CH:27]=[C:28]([CH3:29])[C:15]=2[N:14]([CH2:30][C:31]2[N:32]=[CH:33][NH:34][CH:35]=2)[C:13]1=[O:55]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 8857Ethyl AcetateHCID 21701268HCID 21701268, compound

Product 1

HCID 178423602HCID 178423602, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of (3RS)-3-benzyloxycarbonylamino-5-cyclohexyl-2,3-dihydro-9-methyl-1-(1-triphenylmethylimidazol-4-yl)methyl-1H-1,4-benzodiazepin-2-one (0.5 g) and 30% hydrobromic acid in acetic acid (2.0 ml) was stirred at room temperature overnight. The reaction mixture was poured into a mixture of an ice and ethyl acetate under stirring. The separated water layer was washed with ethyl acetate once, and neutralized with a saturated aqueous solution of sodium bicarbonate. The resultant aqueous mixture was extracted with ethyl acetate and the extract was dried over sodium sulfate. Removal of the solvent in vacuo afforded (3RS)-3-amino-5-cyclohexyl-2,3-dihydro-1-(imidazol-4-yl)methyl-9-methyl-1H-1,4-benzodiazepin-2-one (174 mg, 72.1%) as a crystalline powder.

Workup

  1. stirringunder stirring
  2. washThe separated water layer was washed with ethyl acetate once
  3. extractionThe resultant aqueous mixture was extracted with ethyl acetate
  4. dry with materialthe extract was dried over sodium sulfate
  5. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-79fd083213744bd2aaeaec52a76aab67
Source dataset
uspto-grants-2001_09
Patent number
US06291452B1

Reaction notes

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