Hydrogen Bromide → HCID 178491353, compound

HRID 1971472Notes

Reaction equation

HRID 1971472 reaction equation
Br.C(OC([N:12]1[CH2:17][CH2:16][C:15]2[N:18]=[C:19]([NH:21][C:22]([NH:24][CH2:25][C:26]3[C:31]([O:32][CH3:33])=[CH:30][CH:29]=[CH:28][C:27]=3[O:34][CH3:35])=[NH:23])[S:20][C:14]=2[CH2:13]1)=O)C1C=CC=CC=1.C(=O)([O-])[O-]>C(O)(=O)C.CO>[CH3:35][O:34][C:27]1[CH:28]=[CH:29][CH:30]=[C:31]([O:32][CH3:33])[C:26]=1[CH2:25][NH:24][C:22]([NH:21][C:19]1[S:20][C:14]2[CH2:13][NH:12][CH2:17][CH2:16][C:15]=2[N:18]=1)=[NH:23]

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 19660Carbonate IonHCID 178491355HCID 178491355, compound

Product 1

HCID 178491353HCID 178491353, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

0.2 ml HBr (33% in glacial acetic acid) were added to 150 mg benzyl-2-{[[(2,6-dimethoxybenzyl)amino](imino)methyl]amino}-6,7-dihydro[1,3]thiazolo[5,4-c]pyridine-5(4H)-carboxylat (0.28 mmol) in 2 ml glacial acetic acid, and the mixture was stirred for 2 hours at room temperature. After reaction completion, the mixture was evaporation-concentrated, was filtered over C18 Chromabond (water/CH3CN+0.1% glacial acetic acid; 0-30%), and the free base was obtained by stirring with polymer-bound carbonate in methanol. 60 mg; ESI-MS [M+H+]=348.15.

Workup

  1. customAfter reaction completion
  2. concentrationthe mixture was evaporation-concentrated
  3. filtrationwas filtered over C18 Chromabond (water/CH3CN+0.1% glacial acetic acid; 0-30%)
  4. customthe free base was obtained

Sources & evidence

ORD record
ord-b4210d97f09a436ea4b259bb471fc154
Source dataset
uspto-grants-2013_04
Patent number
US08431604B2

Reaction notes

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