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

HRID 449028Notes

Reaction equation

HRID 449028 reaction equation
[NH3:1].Cl[C:3]1[C:4]2[N:5]([C:9]([CH:25]3[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)C>[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)[CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 866360308-Chloro-3-cyclopentyl-1-(4-phenoxyphenyl)-imidazo[1,5-a]pyrazine

Product 1

HCID 210368713-Cyclopentyl-1-(4-phenoxyphenyl)-imidazo[1,5-a]pyrazin-8-ylamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

20 M NH3 in H2O (2 mL) was added to a suspension of 8-chloro-3-cyclopentyl-1-(4-phenoxyphenyl)-imidazo[1,5-a]pyrazine (21 mg, 0.054 mmol) in i-PrOH (2 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 using 10% MeOH in DCM afforded 9 mg of the title compound as an off white solid. The compound was registered as OSIP 700099. 1H NMR (400 MHz, CDCl3): δ=1.61-1.95 (m, 4H), 2.02-2.23 (m, 4H), 3.30-3.43 (m, 1H), 5.07 (br. s., 2H), 7.03-7.08 (m, 3H), 7.08-7.16 (m, 3H), 7.23 (d, J=5.05 Hz, 1H), 7.30-7.41 (m, 2H), 7.61 (d, 2H). MS (ES+): m/z 370.83 (100)[MH+]. HPLC: tR=2.61 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

Sources & evidence

ORD record
ord-0592626016c0482498a7be3ee7ecca69
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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