Formaldehyde → 5-Chloro-2-[1-(1-methyl-hexahydroazepin-4-yl)piperidin-4-ylcarbonylamino]-N-(5-chloropyridin-2-yl)benzamide

HRID 1373716Notes

Reaction equation

HRID 1373716 reaction equation
[BH3-][C:2]#[N:3].[Na+].[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([NH:22][C:23]([CH:25]2[CH2:30][CH2:29][N:28]([CH:31]3[CH2:37][CH2:36][CH2:35]N[CH2:33][CH2:32]3)[CH2:27][CH2:26]2)=[O:24])=[C:10]([CH:21]=1)[C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][N:15]=1)=[O:12].C=O>>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([NH:22][C:23]([CH:25]2[CH2:26][CH2:27][N:28]([CH:31]3[CH2:37][CH2:36][CH2:35][N:3]([CH3:2])[CH2:33][CH2:32]3)[CH2:29][CH2:30]2)=[O:24])=[C:10]([CH:21]=1)[C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][N:15]=1)=[O:12]

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 210753195-chloro-2-[1-(hexahydroazepin-4-yl)piperidin-4-ylcarbonylamino]-N-(5-chloropyridin-2-yl)benzamide

Product 1

HCID 210753175-Chloro-2-[1-(1-methyl-hexahydroazepin-4-yl)piperidin-4-ylcarbonylamino]-N-(5-chloropyridin-2-yl)benzamide

Procedure

Alternatively, 5-chloro-2-[1-(1-methyl-hexahydroazepin-4-yl)piperidin-4-ylcarbonylamino]-N-(5-chloropyridin-2-yl)-benzamide is prepared by a NaCNBH3 reductive alkylation of 5-chloro-2-[1-(hexahydroazepin-4-yl)piperidin-4-ylcarbonylamino]-N-(5-chloropyridin-2-yl)benzamide with formaldehyde.

Sources & evidence

ORD record
ord-99ddf83aa5a9437a9981b1c4182bcd2c
Source dataset
uspto-grants-2007_01
Patent number
US07163938B2

Reaction notes

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