HCID 59852739, compound → HCID 178501051, compound

HRID 2373869Notes

Reaction equation

HRID 2373869 reaction equation
C(OC1C=C(C(NC(C2CCCCCC2)=O)C2C(Cl)=NC=CN=2)C=CC=1)C1C=CC=CC=1.[CH3:33][O:34][C:35]([C@H:37]1[CH2:42][CH2:41][C@@H:40]([C:43](=O)[NH:44][CH:45]([C:53]2[CH:58]=[CH:57][CH:56]=[C:55]([O:59][CH2:60][C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=3)[CH:54]=2)[C:46]2[C:51]([Cl:52])=[N:50][CH:49]=[CH:48][N:47]=2)[CH2:39][CH2:38]1)=[O:36]>>[CH3:33][O:34][C:35]([C@H:37]1[CH2:38][CH2:39][C@@H:40]([C:43]2[N:47]3[CH:48]=[CH:49][N:50]=[C:51]([Cl:52])[C:46]3=[C:45]([C:53]3[CH:58]=[CH:57][CH:56]=[C:55]([O:59][CH2:60][C:61]4[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=4)[CH:54]=3)[N:44]=2)[CH2:41][CH2:42]1)=[O:36]

Participants

3

Reactant 2

HCID 59852739HCID 59852739, compound2×HCID 178501154HCID 178501154, compound3×

Product 1

HCID 178501051HCID 178501051, compound

Procedure

cis-4-[1-(3-Benzyloxy-phenyl)-8-chloro-imidazo[1,5-a]pyrazin-3-yl]-cyclohexanecarboxylic acid methyl ester (compound of Formula II-A where Z=cyclohexyl, CO2A3=4-cis-CO2Me, and Q1=Ph-(3-OBn)) was prepared according to the procedures described for 1-(3-benzyloxy-phenyl)-8-chloro-3-cyclobutyl-imidazo[1,5-a]pyrazine (compound of Formula II where R1=cyclobutyl and Q1=Ph-(3-OBn)) above except for the substitution of cyclobutanecarboxylic acid [(3-benzyloxy-phenyl)-(3-chloro-pyrazin-2-yl)-methyl]amide (compound of Formula III where R1=cyclobutyl and Q1=Ph-(3-OBn)) with cis-4-{[(3-benzyloxy-phenyl)-(3-chloro-pyrazin-2-yl)-methyl]-carbamoyl}-cyclohexanecarboxylic acid methyl ester (compound of Formula III where R1=trans-4-cyclohexane carboxylic acid methyl ester and Q1=Ph-(3-OBn)); MS (ES) 476.2 (M+1), 478.2 (M+3).

Sources & evidence

ORD record
ord-703a63c5e5f04c94836184c66fffff82
Source dataset
uspto-grants-2008_12
Patent number
US07459554B2

Reaction notes

Loading…