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

HRID 1373715

Reaction equation

HRID 1373715 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:18][C:19]([CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[O:20])=[C:6]([CH:17]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=1)=[O:8].[CH3:27][N:28]1[CH2:34][CH2:33][CH2:32][C:31](=O)[CH2:30][CH2:29]1.[BH3-]C#N.[Na+].C(O)(=O)C>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:18][C:19]([CH:21]2[CH2:22][CH2:23][N:24]([CH:31]3[CH2:32][CH2:33][CH2:34][N:28]([CH3:27])[CH2:29][CH2:30]3)[CH2:25][CH2:26]2)=[O:20])=[C:6]([CH:17]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=1)=[O:8]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 2625861-Methylazepan-4-oneHCID 5003444Sodium cyanoborohydrideHCID 210753345-chloro-2-(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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound is prepared from 5-chloro-2-(piperidin-4-ylcarbonylamino)-N-(5-chloropyridin-2-yl)-benzamide and 1-methyl-hexahydro-4H-azepin-4-one by reductive alkylation using NaCNBH3 and 5%-acetic acid in methanol, for example using a procedure similar to that of Example 25-F.

Sources & evidence

ORD record
ord-f3ea6a1a0d5a4e8ab9034749e7fa23fe
Source dataset
uspto-grants-2007_01
Patent number
US07163938B2

Linked notes

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