1-Methylhomopiperazine → 2-[4-(4-Methylhexahydro-1,4-diazepin-1-yl)piperidin-1-ylcarbonyl]amino-N-(5-chloropyridin-2-yl)benzamide

HRID 1373714Notes

Reaction equation

HRID 1373714 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:26])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][C:17]([N:19]2[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]2)=[O:18])=[N:6][CH:7]=1.[CH3:27][N:28]1[CH2:34][CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.C([BH3-])#N.[Na+]>C(O)(=O)C.CO>[CH3:27][N:28]1[CH2:34][CH2:33][CH2:32][N:31]([CH:22]2[CH2:23][CH2:24][N:19]([C:17]([NH:16][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[C:9]([NH:8][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=3)=[O:26])=[O:18])[CH2:20][CH2:21]2)[CH2:30][CH2:29]1

Participants

6

Reactant 3

HCID 2283491-MethylhomopiperazineHCID 5003444Sodium cyanoborohydrideHCID 21906655N-(5-Chloropyridin-2-yl)-2-(4-oxopiperidin-1-ylcarbonyl)aminobenzamide

Product 1

HCID 210753062-[4-(4-Methylhexahydro-1,4-diazepin-1-yl)piperidin-1-ylcarbonyl]amino-N-(5-chloropyridin-2-yl)benzamide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 887MethanolSolvent2×

Procedure

A solution of N-(5-chloropyridin-2-yl)-2-(4-oxo-piperidin-1-ylcarbonyl)aminobenzamide (100 mg, 0.268 mmol) and 4-methyl(hexahydro-1,4-diazepine) (0.03 mL, 0.241 mmol) in 10% acetic acid in methanol (2.2 mL) was treated with sodium cyanoborohydride (20 mg, 0.268 mmol). After 15 h, the mixture was loaded onto a SCX column, which was pretreated with a solution of 5% acetic acid in methanol. The column was eluted with methanol followed by 2 N ammonia in methanol. The eluent was concentrated to afford title compound.

Workup

  1. washThe column was eluted with methanol
  2. concentrationThe eluent was concentrated

Sources & evidence

ORD record
ord-f11a75d437d447ea94c534a460c374b2
Source dataset
uspto-grants-2007_01
Patent number
US07163938B2

Reaction notes

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