Ammonia → 3-Methyl-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-8-amine

HRID 244091Notes

Reaction equation

Cl[C:2]1[C:3]2[N:4]([C:8]([CH3:27])=[N:9][C:10]=2[C:11]2[CH:20]=[C:19]3[C:14]([CH:15]=[CH:16][C:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[N:18]3)=[CH:13][CH:12]=2)[CH:5]=[CH:6][N:7]=1.[NH3:28]>CC(O)C.C(Cl)Cl>[CH3:27][C:8]1[N:4]2[CH:5]=[CH:6][N:7]=[C:2]([NH2:28])[C:3]2=[C:10]([C:11]2[CH:20]=[C:19]3[C:14]([CH:15]=[CH:16][C:17]([C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)=[N:18]3)=[CH:13][CH:12]=2)[N:9]=1

Participants

Conditions

Temperature: 110 °C

Procedure

7-(8-Chloro-3-methyl-imidazo[1,5-a]pyrazin-1-yl)-2-phenyl-quinoline was dissolved in 10.0 mL of 2.0M NH3 in IPA and 5.0 mL of CH2Cl2. The reaction was heated to 110° C. for 64 h. The salts were filtered off and washed with CH2Cl2. Purified with silica gel column chromatography [Jones Flashmaster, 10 g cartridge, eluting with 1% MeOH:EtOAc] to yield a dark yellow solid; 1H NMR (400 MHz, CDCl3) δ 2.71 (s, 3H), 5.61 (brs, 2H), 7.13 (d, 1H, J=5.1 Hz), 7.2 (d, 1H, J=5.1 Hz), 7.48-7.56 (m, 3H), 7.89-7.97 (m, 3H), 8.18-8.21 (m, 2H), 8.27 (d, 1H, J=8.6 Hz), 8.39 (s, 1H); MS (ES+): 352.06 (M+1), 353.07 (M+2), 354.09 (M+3).

Workup

filtrationThe salts were filtered off
washwashed with CH2Cl2
customPurified with silica gel column chromatography [Jones Flashmaster, 10 g cartridge, eluting with 1% MeOH:EtOAc]
customto yield a dark yellow solid

Sources & evidence

ORD record: ord-b65d45498a704aa7a5b61d1b789d09a8
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653268B2

Reaction notes

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