1-Hydroxybenzotriazole → Methyl cis(+/-)-4-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-6-methylpyridine-2-carboxylate
Reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[C:12]([CH3:14])[N:11]=[C:10]([C:15]([O:17][CH3:18])=[O:16])[CH:9]=2)[CH2:4][C@H:3]1[O:19][CH3:20].[Cl:21][C:22]1[N:23]=[C:24]([C:29](O)=[O:30])[NH:25][C:26]=1[CH2:27][CH3:28].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>>[Cl:21][C:22]1[N:23]=[C:24]([C:29]([NH:1][C@H:2]2[CH2:7][CH2:6][N:5]([C:8]3[CH:13]=[C:12]([CH3:14])[N:11]=[C:10]([C:15]([O:17][CH3:18])=[O:16])[CH:9]=3)[CH2:4][C@H:3]2[O:19][CH3:20])=[O:30])[NH:25][C:26]=1[CH2:27][CH3:28]Participants
5
Reactant 4
Product 1
Procedure
The same operation as in Example (1g) was performed using methyl cis(±)-4-(4-amino-3-methoxypiperidin-1-yl)-6-methylpyridine-2-carboxylate obtained in Example (168b) (129 mg, 0.44 mmol), 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid obtained by the method described in Example (1d) (64 mg, 0.37 mmol), WSC hydrochloride (211 mg, 1.1 mmol) and HOBt (49.7 mg, 0.37 mmol), to obtain 174 mg of the title compound as a pale yellow oily substance.
Workup
- customobtained by the method
Sources & evidence
- ORD record
- ord-ea77d56b89fc4f8abcc9051ad08d2417
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08927588B2
Reaction notes
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