Ammonia → HCID 16755042, compound

HRID 1992429Notes

Reaction equation

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

Participants

Conditions

Temperature: 110 °C

Procedure

A solution of 1-(3-benzyloxy-phenyl)-8-chloro-2H-imidazo[1,5-a]pyrazin-3-one (100 mg, 0.28 mmol) in i-PrOH (4 mL) was saturated with NH3 at −20° C. and heated 110° C. in a sealed tube for 48 hours. The light brown reaction mixture was partitioned in water and DCM and separated. The aqueous layer was washed with DCM (3×) and the combined organic layers were washed with brine (1×), dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was purified by chromatography on silica gel [eluting with 8% MeOH in DCM], resulting in the title compound as a pale brown solid; 1H NMR (DMSO-d6, 400 MHz) δ=5.16 (s, 2H), 5.86 (brs, 2H), 6.70 (d, J=5.2 Hz, 1H), 7.01 (d, J=4.8 Hz, 1H), 7.07-7.14 (m, 2H), 7.24 (brt, J=2 Hz, 1H), 7.32-7.49 (m, 7H); MS (ES+): m/z=333.21 (100) [MH+], HPLC: tR=2.05 min (MicromassZQ, polar—5 min).

Workup

customThe light brown reaction mixture was partitioned in water
customDCM and separated
washThe aqueous layer was washed with DCM (3×)
washthe combined organic layers were washed with brine (1×)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude material was purified by chromatography on silica gel [eluting with 8% MeOH in DCM]

Sources & evidence

ORD record: ord-f6627f26e03b4ec2aa2d9e751402d6ac
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07648987B2

Reaction notes

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