Hydrochloric Acid → HCID 178484004, compound

HRID 245748Notes

Reaction equation

HRID 245748 reaction equation
C(O[C:9](=O)[N:10]([CH2:12][C@H:13]1[CH2:18][CH2:17][C@H:16]([C:19]2[N:23]3[CH:24]=[CH:25][N:26]=[C:27]([CH3:28])[C:22]3=[C:21]([Br:29])[N:20]=2)[CH2:15][CH2:14]1)C)C1C=CC=CC=1.Cl>>[Br:29][C:21]1[N:20]=[C:19]([C@H:16]2[CH2:17][CH2:18][C@H:13]([CH2:12][NH:10][CH3:9])[CH2:14][CH2:15]2)[N:23]2[CH:24]=[CH:25][N:26]=[C:27]([CH3:28])[C:22]=12

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 178432909HCID 178432909, compound

Product 1

HCID 178484004HCID 178484004, compoundYield 90.2%

Procedure

The impure benzyl((trans)-4-(1-bromo-8-methylimidazo[1,5-a]pyrazin-3-yl)cyclohexyl)methyl(methyl)carbamate (0.299 mmol, 141 mg) in 37% hydrochloric acid (20.94 mmol, 1.745 ml) was stirred for 18 hours at room temperature and one hour at 40° C. The reaction mixture was concentrated in vacuo. The residue dissolved in water and washed with diethyl ether twice. The aqueous layer basified with 2 N aqueous sodium hydroxide and extracted with dichloromethane twice. The combined organic extracts were dried (Na2SO4) and concentrated in vacuo to give impure 1-((trans)-4-(1-bromo-8-methylimidazo[1,5-a]pyrazin-3-yl)cyclohexyl)-N-methylmethanamine (91 mg).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionThe residue dissolved in water
  3. washwashed with diethyl ether twice
  4. extractionextracted with dichloromethane twice
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1cbfc8152b784258ab37e538c23b5302
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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