Ammonia → 3-Cyclopropyl-1-(4-phenoxyphenyl)-imidazo[1,5-a]pyrazin-8-ylamine

HRID 449025Notes

Reaction equation

HRID 449025 reaction equation
[NH3:1].Cl[C:3]1[C:4]2[N:5]([C:9]([CH:25]3[CH2:27][CH2:26]3)=[N:10][C:11]=2[C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:14][CH:13]=2)[CH:6]=[CH:7][N:8]=1>O.CC(O)CC>[CH:25]1([C:9]2[N:5]3[CH:6]=[CH:7][N:8]=[C:3]([NH2:1])[C:4]3=[C:11]([C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:14][CH:13]=3)[N:10]=2)[CH2:27][CH2:26]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 866360288-Chloro-3-cyclopropyl-1-(4-phenoxyphenyl)-imidazo[1,5-a]pyrazine

Product 1

HCID 445388953-Cyclopropyl-1-(4-phenoxyphenyl)-imidazo[1,5-a]pyrazin-8-ylamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6568(+-)-2-ButanolSolvent

Procedure

A solution of NH3 in H2O (20 M, 2 mL) was added to a suspension of 8-chloro-3-cyclopropyl-1-(4-phenoxyphenyl)-imidazo[1,5-a]pyrazine (33 mg, 0.091 mmol) in 2-butanol (0.4 mL). The mixture was heated in an oil bath set at 105° C. overnight. Reaction mixture was concentrated in vacuo and purification by prep TLC (4% MeOH in DCM as eluent) afforded the title compound as a solid. 1H NMR (400 MHz, CDCl3): δ 0.95-1.22 (m, 4H), 1.93-2.09 (m, 1H), 5.10 (br. s., 2H), 7.02-7.18 (m, 6H), 7.32-7.44 (m, 3H), 7.55-7.62 (m, 2H). MS (ES+): m/z 343.15 (100)[MH+]. HPLC: tR=2.52 min (Open Lynx polar—5 min).

Workup

  1. temperatureThe mixture was heated in an oil bath
  2. customReaction mixture
  3. concentrationwas concentrated in vacuo and purification by prep TLC (4% MeOH in DCM as eluent)

Sources & evidence

ORD record
ord-6c58f9950c9a49b386994fb4db98f1f2
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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