Ammonia → HCID 11560235, compound

HRID 422650Notes

Reaction equation

C(Cl)Cl.Cl[CH:5]1[NH:10][CH:9]=[CH:8][N:7]2[C:11]([CH:30]3[CH2:33][CH2:32][CH2:31]3)=[N:12][C:13]([C:14]3[CH:23]=[C:22]4[C:17]([N:18]=[CH:19][C:20]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)=[N:21]4)=[CH:16][CH:15]=3)=[C:6]12.[N:34]#N.N>CC(O)C>[CH:30]1([C:11]2[N:7]3[CH:8]=[CH:9][N:10]=[C:5]([NH2:34])[C:6]3=[C:13]([C:14]3[CH:23]=[C:22]4[C:17](=[CH:16][CH:15]=3)[N:18]=[CH:19][C:20]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[N:21]4)[N:12]=2)[CH2:33][CH2:32][CH2:31]1

Participants

Conditions

Temperature: 100 °C

Procedure

DCM solution of 7-(8-chloro-3-cyclobutyl-7,8-dihydroimidazo[1,5-a]pyrazin-1-yl)-2-phenylquinoxaline (61 mg, 0.15 mmol) was evaporated to dryness by passing a stream of N2. The residue was suspended in anh. i-PrOH (4 mL) and the suspension was saturated with gaseous NH3 at 0° C. (2 min). The reaction vessel was sealed and heated to 100° C. (external temperature) for 63 h. Then the reaction was cooled to rt, concentrated under reduced pressure and purified by flash chromatography (silica gel, 0-5% MeOH in DCM) and then preparative TLC (4% MeOH in CH3CN) to afford the title compound as a light yellow solid; 1H NMR (400 MHz, CDCl3) δ 9.36 (d, J=4 Hz, 1H), 8.43 (s, 1H), 8.30-8.25 (m, 4H), 7.65-7.50 (m, 3H), 7.15 (m, 2H), 5.26 (br, 2H), 3.86 (quintet, J=8 Hz, 1H), 2.75-2.60 (m, 2H), 2.60-2.45 (m, 2H), 2.20 (q, J=8 Hz, 1H), 2.07 (br, 1H). MS (ES+): m/z 393.1 (100) [MH+]; HPLC: tR=2.30 min (OpenLynx, polar—5 min).

Workup

custom(2 min)
customThe reaction vessel was sealed
temperatureThen the reaction was cooled to rt
concentrationconcentrated under reduced pressure
custompurified by flash chromatography (silica gel, 0-5% MeOH in DCM)

Sources & evidence

ORD record: ord-de205427a80244beba550e06ecefde1a
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101613B2

Reaction notes

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