Sodium Hydroxide → 2-[4-(4-Methylhexahydro-1,4-diazepin-1-yl)-benzylamino]-N-(5-chloropyridin-2-yl)pyridine-3-carboxamide

HRID 1373701Notes

Reaction equation

HRID 1373701 reaction equation
Cl[C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][N:12]=2)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:18][N:19]1[CH2:25][CH2:24][CH2:23][N:22]([C:26]2[CH:33]=[CH:32][C:29]([CH2:30][NH2:31])=[CH:28][CH:27]=2)[CH2:21][CH2:20]1.[OH-].[Na+]>CS(C)=O.O>[CH3:18][N:19]1[CH2:25][CH2:24][CH2:23][N:22]([C:26]2[CH:33]=[CH:32][C:29]([CH2:30][NH:31][C:2]3[C:7]([C:8]([NH:10][C:11]4[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][N:12]=4)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=3)=[CH:28][CH:27]=2)[CH2:21][CH2:20]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 34211092-Chloro-N-(5-chloro-2-pyridinyl)-3-pyridinecarboxamideHCID 185259054-(4-Methyl-1,4-diazepan-1-yl)benzylamine

Product 1

HCID 210753052-[4-(4-Methylhexahydro-1,4-diazepin-1-yl)-benzylamino]-N-(5-chloropyridin-2-yl)pyridine-3-carboxamideYield 8.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of 2-chloro-N-(5-chloropyridin-2-yl)pyridine-3-carboxamide (1.00 g, 3.7 mmol) and 4-(4-methylhexahydro-1,4-diazepin-1-yl)benzylamine (0.63 g, 2.9 mmol), in 5 mL of DMSO, was heated in a sealed tube at 70–75° C. for 35 h. This reaction mixture was diluted with 250 mL of water, basified with 2 N NaOH, and extracted with ethyl acetate and evaporated to give 0.83 g crude product. Flash chromatography purification with 10% MeOH—CHCl3, 1% NH4OH gave the title product (0.11 g, 8.5%).

Workup

  1. extractionextracted with ethyl acetate
  2. customevaporated
  3. customto give 0.83 g crude product
  4. customFlash chromatography purification with 10% MeOH—CHCl3, 1% NH4OH

Sources & evidence

ORD record
ord-bde3b6a3f003469ba749fb886bc0b557
Source dataset
uspto-grants-2007_01
Patent number
US07163938B2

Reaction notes

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