HCID 59852764, compound → HCID 178508469, compound

HRID 2373870Notes

Reaction equation

HRID 2373870 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([C@H:25]3[CH2:30][CH2:29][C@H: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]=1

Participants

3

Reactant 2

HCID 59852764HCID 59852764, compoundHCID 178508468HCID 178508468, compound

Product 1

HCID 178508469HCID 178508469, compound

Procedure

cis-{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 trans-4-[8-amino-1-(3-benzyloxy-phenyl)-imidazo[1,5-a]pyrazin-3-yl]-cyclohexanecarboxylic acid amide except for the substitution of cis-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-cis-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)); MS (ES) 429.2 (M+1).

Sources & evidence

ORD record
ord-c01b3b73e06943f99e55b5db73e58088
Source dataset
uspto-grants-2008_12
Patent number
US07459554B2

Reaction notes

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