Water → HCID 58342140, compound

HRID 339574Notes

Reaction equation

HRID 339574 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[N:18]=[C:19]4[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]4[CH:26]=3)=[CH:13][CH:12]=2)=[O:9])=[CH:4][CH:3]=1.Cl.[CH3:28][NH:29][CH3:30].C([O-])([O-])=O.[K+].[K+].O>CS(C)=O>[CH3:28][N:29]([CH3:30])[C:2]1[N:7]=[CH:6][C:5]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[N:18]=[C:19]4[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]4[CH:26]=3)=[CH:13][CH:12]=2)=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 58342048HCID 58342048, compound

Product 1

HCID 58342140HCID 58342140, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
170 °C

Procedure

A stirred mixture of 6-chloro-N-[4-(6-methylimidazo[1,2-a]pyridin-2-yl)phenyl]pyridine-3-carboxamide (0.15 g, 0.414 mmol), dimethylamine hydrochloride (0.845 g, 10.36 mmol) and K2CO3 (1.43 g, 10.36 mmol) in dry DMSO (10 ml) was heated at 170° C. for 16 h under an atmosphere of argon. The cooled reaction mixture was added to water (200 ml) and the precipitate was collected by filtration and dried in the air. The solid was purified by flash chromatography (12:1 DCM/MeOH) to give the title compound (0.113 g, 73%) as a pale yellow solid.

Workup

  1. customThe cooled reaction mixture
  2. filtrationthe precipitate was collected by filtration
  3. customdried in the air
  4. customThe solid was purified by flash chromatography (12:1 DCM/MeOH)

Sources & evidence

ORD record
ord-a37e601a86634359b68371676d4272e1
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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