trans-4-(8-Amino-1-(3-(benzyloxy)phenyl)imidazo[1,5-a]pyrazin-3-yl)cyclohexanecarboxamide → HCID 178508470, compound
Reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([CH:25]3[CH2:30][CH2:29][CH:28]([C:31](N)=[O:32])[CH2:27][CH2:26]3)=[N:9][C:10]=2[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:12]=2)[CH:5]=[CH:6][N:7]=1.C(OC1C=C(C2N=C(C3CCC(CO)CC3)N3C=CN=C(Cl)C=23)C=CC=1)C1C=CC=CC=1>>[NH2:1][C:2]1[C:3]2[N:4]([C:8]([C@H:25]3[CH2:30][CH2:29][C@H:28]([CH2:31][OH:32])[CH2:27][CH2:26]3)=[N:9][C:10]=2[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:12]=2)[CH:5]=[CH:6][N:7]=1Participants
Procedure
trans-{4-[8-Amino-1-(3-benzyloxy-phenyl)-imidazo[1,5-a]pyrazin-3-yl]-cyclohexyl}-methanol (compound of Formula I-B where Z=cyclohexyl and Q1=Ph-(3-OBn)) was prepared according to the procedures described for the synthesis of 4-[8-amino-1-(3-benzyloxy-phenyl)-imidazo[1,5-a]pyrazin-3-yl]-cyclohexanecarboxylic acid amide except for the substitution of trans-4-[1-(3-benzyloxyphenyl)-8-chloro-imidazo[1,5-a]pyrazin-3-yl]cyclohexane carboxylic acid methyl ester (compound of Formula II-A where Z=cyclohexyl, CO2A3=4-trans-CO2Me, and Q1=Ph-(3-OBn)) with {4-[1-(3-benzyloxy-phenyl)-8-chloro-imidazo[1,5-a]pyrazin-3-yl]-cyclohexyl}-methanol (compound of Formula II-B where Z=cyclohexyl and Q1=Ph-(3-OBn)); 1H NMR (CDCl3, 400 MHz) δ 1.21 (ddd, 2H, J=25.2 Hz, 12.8 Hz, 3.6 Hz), 1.65-1.71 (m, 1H), 1.91 (ddd, 2H, J=29.6 Hz, 13.2 Hz, 3.6 Hz), 2.00-2.05 (m, 2H), 2.12-2.16 (m, 2H), 2.93 (tt, 1H, J=11.6 Hz, 4.0 Hz), 3.56 (d, 2H, J=6.0 Hz), 5.11 (bs, 2H), 5.16 (s, 2H), 7.05 (ddd, 1H, J=8.0 Hz, 2.8 Hz, 1.2 Hz), 7.07 (d, 1H, J=5.2 Hz), 7.20-7.22 (m, 2H), 7.23-7.24 (m, 2H), 7.31-7.35 (m, 1H), 7.36-7.41 (m, 2H), 7.42-7.45 (m, 2H); MS (ES) 429.5 (M+1).
Sources & evidence
- ORD record
- ord-d931075c74434e7482600778713a11fd
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07459554B2
Reaction notes
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