Isobutyryl chloride → 2-(ethoxymethyl)-1-[2-(1-isobutyrylpiperidin-4-yl)ethyl]-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine

HRID 2085259Notes

Reaction equation

HRID 2085259 reaction equation
[C:1](Cl)(=[O:5])[CH:2]([CH3:4])[CH3:3].[CH2:7]([O:9][CH2:10][C:11]1[N:12]([CH2:23][CH2:24][CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[C:13]2[C:18]([CH3:19])=[C:17]([CH3:20])[N:16]=[C:15]([NH2:21])[C:14]=2[N:22]=1)[CH3:8]>ClCCl.C(Cl)(Cl)Cl>[CH2:7]([O:9][CH2:10][C:11]1[N:12]([CH2:23][CH2:24][CH:25]2[CH2:26][CH2:27][N:28]([C:1](=[O:5])[CH:2]([CH3:4])[CH3:3])[CH2:29][CH2:30]2)[C:13]2[C:18]([CH3:19])=[C:17]([CH3:20])[N:16]=[C:15]([NH2:21])[C:14]=2[N:22]=1)[CH3:8]

Participants

5

Reactant 2

HCID 62325Isobutyryl chlorideHCID 129729622-(ethoxymethyl)-6,7-dimethyl-1-(2-piperidin-4-ylethyl)-1H-imidazo[4,5-c]pyridin-4-amine

Product 1

HCID 101507972-(ethoxymethyl)-1-[2-(1-isobutyrylpiperidin-4-yl)ethyl]-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amineYield 50.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Isobutyryl chloride (96 μL, 0.917 mmol) was added drop wise to a chilled (0° C.) solution of 2-(ethoxymethyl)-6,7-dimethyl-1-(2-piperidin-4-ylethyl)-1H-imidazo[4,5-c]pyridin-4-amine (304 mg, 0.917 mmol) in dichloromethane (10 mL). The reaction mixture was allowed to stir overnight then it was diluted with chloroform and washed with 5% sodium hydroxide, water and brine. The organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was recrystallized from acetonitrile to provide 185 mg of 2-(ethoxymethyl)-1-[2-(1-isobutyrylpiperidin-4-yl)ethyl]-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine as a yellowish solid, m.p. 167.5-169.2° C.

Workup

  1. washwashed with 5% sodium hydroxide, water and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-484f9a1f9ae64972a9f58eb8db9de8db
Source dataset
uspto-grants-2004_04
Patent number
US06720333B2

Reaction notes

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