Hydrogen Bromide → HCID 19063668, compound

HRID 482347Notes

Reaction equation

HRID 482347 reaction equation
C(OC([NH:11][CH:12]1[C:18](=[O:19])[N:17]([CH2:20][C:21]([N:23]([CH:32]([CH3:34])[CH3:33])[C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)=[O:22])[C:16]2[CH:35]=[CH:36][CH:37]=[CH:38][C:15]=2[C:14]([C:39]2[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=2)=[N:13]1)=O)C1C=CC=CC=1.[BrH:45]>C(O)(=O)C>[BrH:45].[NH2:11][CH:12]1[C:18](=[O:19])[N:17]([CH2:20][C:21]([N:23]([CH:32]([CH3:34])[CH3:33])[C:24]2[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=2)=[O:22])[C:16]2[CH:35]=[CH:36][CH:37]=[CH:38][C:15]=2[C:14]([C:39]2[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=2)=[N:13]1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 19063679HCID 19063679, compound

Product 1

HCID 19063668HCID 19063668, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 1.00 g of 2-[3-(N-benzyloxycarbonyl-amino)-2-oxo-5-pyridin-3-yl-2,3-dihydro-benzo[e][1,4]diazepin-1-yl]-N-isopropyl-N-(4-methoxy-phenyl)-acetamide (1.690 mmol), prepared as in Intermediate 30, in 6 mL glacial acetic acid was saturated with hydrogen bromide gas and stirred at ambient temperature for 16 hrs. The reaction mixture was evaporated in vacuo to a residue and triturated with diethyl ether. The resulting slurry was filtered, washed with diethyl ether, and dried under high vacuum to provide 1.062 g of the title compound as a dihydrobromide salt. 1H NMR (300 MHz, CD3 OD) -- =9.06 (m, 2H), 8.85 (m, 1H), 8.21 (dd, 1H, J=5.8, 8.1), 7.84 (m, 1H), 7.61 (d, 1H, J=8.3), 7.50 (m, 2H), 7.27 (m, 2H), 7.10 (d, 2H, J=8.8), 5.25 (s, 1H), 4.52 (d, 1H, J=16.7), 4.31 (d, 1H, J=16.7), 3.88 (s, 3H), 1.07 (m, 6H); MS (ESI): [M+H]+ =458.

Workup

  1. customThe reaction mixture was evaporated in vacuo to a residue
  2. customtriturated with diethyl ether
  3. filtrationThe resulting slurry was filtered
  4. washwashed with diethyl ether
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-44e536efcc35427ebf9f588787553a53
Source dataset
uspto-grants-1998_08
Patent number
US05795887

Reaction notes

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