tert-Butyl 4-formylpiperidine-1-carboxylate → N-(5-Chloropyridin-2-yl)-4-methoxycarbonyl-2-(piperidin-4-ylmethylamino)benzamide

HRID 1883007Notes

Reaction equation

HRID 1883007 reaction equation
[NH2:1][C:2]1[CH:17]=[C:16]([C:18]([O:20][CH3:21])=[O:19])[CH:15]=[CH:14][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][N:8]=1)=[O:5].C(OC([N:29]1[CH2:34][CH2:33][CH:32]([CH:35]=O)[CH2:31][CH2:30]1)=O)(C)(C)C.[B-][N+](C)(C)C>>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([NH:6][C:4](=[O:5])[C:3]2[CH:14]=[CH:15][C:16]([C:18]([O:20][CH3:21])=[O:19])=[CH:17][C:2]=2[NH:1][CH2:35][CH:32]2[CH2:33][CH2:34][NH:29][CH2:30][CH2:31]2)=[N:8][CH:9]=1

Participants

4

Reactant 3

HCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 6327651Borane,N-dimethylmethanamine (1:1)HCID 219063182-amino-N-(5-chloropyridin-2-yl)-4-methoxycarbonylbenzamide

Product 1

HCID 21906188N-(5-Chloropyridin-2-yl)-4-methoxycarbonyl-2-(piperidin-4-ylmethylamino)benzamideYield 84%

Procedure

Using a similar procedure to that described in Example 47-C&D, 2-amino-N-(5-chloropyridin-2-yl)-4-methoxycarbonylbenzamide (1.00 g, 3.28 mmol), 1-tert-butoxycarbonyl-piperidine-4-carboxaldehyde (1.05 g, 4.92 mmol), and borane trimethylamine complex (717 mg, 9.94 mmol) afforded 1.10 g (84%) of the title compound.

Sources & evidence

ORD record
ord-ab777cd1572e4d30a325d40bad5eeb79
Source dataset
uspto-grants-2004_07
Patent number
US06759414B2

Reaction notes

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