Ammonia → HCID 44538894, compound

HRID 449019Notes

Reaction equation

HRID 449019 reaction equation
[NH3:1].Cl[C:3]1[C:4]2[N:5]([C:9]([CH:25]3[CH2:30][CH2:29][CH2:28][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)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 86636025HCID 86636025, compound

Product 1

HCID 44538894HCID 44538894, compound

Reagents, catalysts & solvents 2

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

Procedure

20 M NH3 in H2O (4 mL) was added to a suspension of 8-chloro-3-cyclohexyl-1-(4-phenoxyphenyl)-imidazo[1,5-a]pyrazine (82 mg, 0.20 mmol) in 2-butanol (0.9 mL). The mixture was heated in an oil bath set at 105° C. overnight. The reaction was stopped at this time and concentrated in vacuo. Purification by prep TLC using 3% NH3 in MeOH in DCM afforded 41.4 mg of the title compound as an off white solid. 1H NMR (400 MHz, CDCl3): δ=1.27-1.52 (m, 3H), 1.73-1.96 (m, 5H), 1.99-2.10 (m, 2H), 2.84-3.02 (m, 1H), 5.28 (br. s., 2H), 7.01-7.08 (m, 3H), 7.09-7.14 (m, 3H), 7.23 (d, J=5.31 Hz, 1H), 7.32-7.40 (m, 2H), 7.58-7.65 (m, 2H). MS (ES+): m/z 385.03 (100)[MH+]. HPLC: tR=2.83 min (Open Lynx polar—5 min).

Workup

  1. temperatureThe mixture was heated in an oil bath
  2. concentrationconcentrated in vacuo
  3. customPurification by prep TLC

Sources & evidence

ORD record
ord-0d615d202e7b473982059d3c9804d744
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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