cis-3-(Boc-amino)-5-methylpiperidine → tert-butyl ((3R,5S)-1-(3-(5-(3,4-dimethoxyphenyl)-7-(trifluoromethyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-2-yl)benzoyl)-5-methylpiperidin-3-yl)carbamate
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[CH2:16][CH:15]([C:17]([F:20])([F:19])[F:18])[N:14]3[N:21]=[C:22]([C:24]4[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=4)[C:27](O)=[O:28])[CH:23]=[C:13]3[NH:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:33]([O:37][C:38](=[O:47])[NH:39][C@@H:40]1[CH2:45][C@H:44]([CH3:46])[CH2:43][NH:42][CH2:41]1)([CH3:36])([CH3:35])[CH3:34]>>[C:33]([O:37][C:38](=[O:47])[NH:39][C@@H:40]1[CH2:45][C@H:44]([CH3:46])[CH2:43][N:42]([C:27](=[O:28])[C:26]2[CH:30]=[CH:31][CH:32]=[C:24]([C:22]3[CH:23]=[C:13]4[NH:12][CH:11]([C:5]5[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=5)[CH2:16][CH:15]([C:17]([F:20])([F:18])[F:19])[N:14]4[N:21]=3)[CH:25]=2)[CH2:41]1)([CH3:36])([CH3:34])[CH3:35]Participants
3
Reactant 2
Product 1
Procedure
Example ER-896389 was prepared in two steps from compound 3-(5-(3,4-dimethoxyphenyl)-7-(trifluoromethyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-2-yl)benzoic acid (25 mg, 0.056 mmol) and commercially available tert-butyl((3R,5S)-5-methylpiperidin-3-yl)carbamate (48 mg, 0.224 mmol) in a manner similar to that of example D-6 to afford intermediate tert-butyl((3R,5S)-1-(3-(5-(3,4-dimethoxyphenyl)-7-(trifluoromethyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-2-yl)benzoyl)-5-methylpiperidin-3-yl)carbamate (22 mg, 0.034 mmol, 61% yield). Then, this intermediate (20 mg, 0.031 mmol) was treated with HCl in a manner similar to that of example ER-897560 to afford the desired product ER-896389 (17.5 mg, 97% yield).
Sources & evidence
- ORD record
- ord-cd6f72e049be4b17b53668534ff68bd8
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09446046B2
Reaction notes
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