5-(Benzyloxy)-2-methylbenzoic acid → 2-(1-{[5-(Benzyloxy)-2-methylphenyl]carbonyl}piperidin-4-yl)-5-(7-methoxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-4-yl)-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one
Reaction equation
Cl.[CH3:2][O:3][C:4]1[C:12]2[O:11][C:10]([CH3:14])([CH3:13])[CH2:9][C:8]=2[C:7]([C:15]2[C:16]([CH3:28])([CH3:27])[C:17](=[O:26])[N:18]([CH:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[N:19]=2)=[CH:6][CH:5]=1.[CH2:29]([O:36][C:37]1[CH:38]=[CH:39][C:40]([CH3:46])=[C:41]([CH:45]=1)[C:42](O)=[O:43])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[CH2:29]([O:36][C:37]1[CH:38]=[CH:39][C:40]([CH3:46])=[C:41]([C:42]([N:23]2[CH2:24][CH2:25][CH:20]([N:18]3[C:17](=[O:26])[C:16]([CH3:28])([CH3:27])[C:15]([C:7]4[C:8]5[CH2:9][C:10]([CH3:14])([CH3:13])[O:11][C:12]=5[C:4]([O:3][CH3:2])=[CH:5][CH:6]=4)=[N:19]3)[CH2:21][CH2:22]2)=[O:43])[CH:45]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1Participants
3
Reactant 2
Product 1
Procedure
The title compound is prepared analogously as described for GP2-WU2 using 5-(7-methoxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-4-yl)-4,4-dimethyl-2-piperidin-4-yl-2,4-dihydro-3H-pyrazol-3-one (compound B5) and 5-(benzyloxy)-2-methylbenzoic acid (compound F1) as starting compounds. The crude product is purified by chromatography (amino phase silica gel and DCM) and by crystallization from DCM and diethyl ether to yield the title compound.
Workup
- customThe title compound is prepared analogously
- customThe crude product is purified by chromatography (amino phase silica gel and DCM) and by crystallization from DCM and diethyl ether
Sources & evidence
- ORD record
- ord-e4310d4ac17f4bbaa43cd5cb1f2b57e9
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08609848B2
Reaction notes
Loading…