Hydrogen Bromide → HCID 18008905, compound

HRID 987489Notes

Reaction equation

HRID 987489 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH:16]=[C:15]([CH2:17][O:18][C:19](=[O:32])[NH:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:23][CH:22]=3)[N:14]=[CH:13]1)[N:8]=[C:7]([C:33]([O:35]CC)=[O:34])[C:6]([O:38]CC)=[N:5]2.Br.C(O)C>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH:16]=[C:15]([CH2:17][O:18][C:19](=[O:32])[NH:20][C:21]3[CH:22]=[CH:23][C:24]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:25][CH:26]=3)[N:14]=[CH:13]1)[N:8]=[C:7]([C:33]([OH:35])=[O:34])[C:6](=[O:38])[NH:5]2

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 702EthanolHCID 18008887HCID 18008887, compound

Product 1

HCID 18008905HCID 18008905, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of ethyl 6-chloro-3-ethoxy-7-(4-(((4-ethoxycarbonylphenyl)carbamoyloxy)methyl)imidazole-1-yl)quinoxaline-2-carboxylate (64.0 mg, 113 μmol) in acetic acid (3 ml) was added 47% hydrobromic acid (0.3 ml), and the mixture was stirred for 3 hours at room temperature. After allowed to stand overnight, the mixture was stirred for 1 hour at 40° C. After cooling, ethanol was added to the residue obtained by concentrating the reaction mixture under reduced pressure. The precipitated crystals were collected by filtration and air-dried, thereby obtaining 18.8 mg of title compound as brown powder. The residue obtained by concentrating the filtrate under reduced pressure was washed with water and air-dried, thereby obtaining additional 37.4 mg. Total yield 56.2 mg. Yield 97%.

Workup

  1. waitto stand overnight
  2. stirringthe mixture was stirred for 1 hour at 40° C
  3. temperatureAfter cooling
  4. customobtained
  5. concentrationby concentrating the reaction mixture under reduced pressure
  6. filtrationThe precipitated crystals were collected by filtration
  7. customair-dried

Sources & evidence

ORD record
ord-5766124ee1da4c35ac46ba1ee1aff5ce
Source dataset
uspto-grants-2003_10
Patent number
US06632813B1

Reaction notes

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