Ammonia → HCID 67096147, compound

HRID 2076491Notes

Reaction equation

HRID 2076491 reaction equation
[NH3:1].[Br:2][C:3]1[N:4]=[C:5]([CH:13]2[CH2:16][C:15]([CH3:18])([OH:17])[CH2:14]2)[N:6]2[CH:11]=[CH:10][N:9]=[C:8](Cl)[C:7]=12>CC(O)CC>[NH2:1][C:11]1[N:6]2[C:5]([CH:13]3[CH2:16][C:15]([CH3:18])([OH:17])[CH2:14]3)=[N:4][C:3]([Br:2])=[C:7]2[CH:8]=[N:9][CH:10]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 533286223-(1-Bromo-8-chloroimidazo[1,5-A]pyrazin-3-YL)-1-methylcyclobutanol

Product 1

HCID 67096147HCID 67096147, compound

Reagents, catalysts & solvents 1

HCID 6568(+-)-2-ButanolSolvent

Conditions

Temperature
90 °C

Procedure

A 35% ammonia solution (132 ml, 2.9 moles) was added to a suspension of 3-(1-bromo-8-chloroimidazo[1,5-a]pyrazin-3-yl)-1-methylcyclobutanol (22.0 g, 0.06463 mol) in 2-butanol (81 ml). The mixture was heated at 90° C. in a pressure vessel for 15 hr then concentrated to 130 ml, cooled to room temperature and the solid collected by filtration. This material was washed with water (3×22 mL) and dried at 40° C. under vacuum. To afford the desired product. 1H NMR (DMSO-d6, 400 MHz): δ 7.5 (d, 1H), 7.0 (d, 1H), 6.6 (bs, 2H), 5.1 (s, 1H), 3.4 (pentet, 1H), 2.3-2.4 (m, 4H) and 1.4 (s, 3H).

Workup

  1. concentrationthen concentrated to 130 ml
  2. temperaturecooled to room temperature
  3. filtrationthe solid collected by filtration
  4. washThis material was washed with water (3×22 mL)
  5. customdried at 40° C. under vacuum

Sources & evidence

ORD record
ord-51e1547718984cb7891f0547e06e173a
Source dataset
uspto-grants-2011_04
Patent number
US07923555B2

Reaction notes

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