Thionyl Chloride → HCID 67262971, compound

HRID 2426367Notes

Reaction equation

HRID 2426367 reaction equation
[NH2:1][C:2]1[C:7]2[N:8]=[C:9]([CH2:15]O)[N:10]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:6]=2[C:5]([CH3:17])=[C:4]([CH3:18])[N:3]=1.S(Cl)([Cl:21])=O>C(Cl)(Cl)Cl>[ClH:21].[Cl:21][CH2:15][C:9]1[N:10]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:6]2[C:5]([CH3:17])=[C:4]([CH3:18])[N:3]=[C:2]([NH2:1])[C:7]=2[N:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 24782597(4-amino-1-isobutyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-2-yl)methanol

Product 1

HCID 67262971HCID 67262971, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of (4-amino-1-isobutyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-2-yl)methanol (1.95 g, 7.85 mmol) and thionyl chloride (1.72 mL, 23.6 mmol) in chloroform (80 mL) was heated at reflux for 2 hours. The solvent was removed under reduced pressure and the residue triturated with chloroform to give 1.53 g of 2-(chloromethyl)-1-isobutyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine hydrochloride as an off-white powder.

Workup

  1. temperatureat reflux for 2 hours
  2. customThe solvent was removed under reduced pressure
  3. customthe residue triturated with chloroform

Sources & evidence

ORD record
ord-2c175a85281a4509ae06b308beba3c38
Source dataset
uspto-grants-2011_06
Patent number
US07968563B2

Reaction notes

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