N-[5-methyl-3-(2,4,6-trimethylphenyl)imidazolo[5,4-b]pyridin-7-yl]-2-chloroacetamide → (2-Chloroethyl)[5-methyl-3-(2,4,6-trimethylphenyl)imidazolo[5,4-b]pyridin-7-yl]-amine

HRID 2121598Notes

Reaction equation

HRID 2121598 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[N:8]([C:11]3[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=3[CH3:19])[CH:9]=[N:10][C:5]2=[C:4]([NH:20][C:21](=O)[CH2:22][Cl:23])[CH:3]=1>C1COCC1>[Cl:23][CH2:22][CH2:21][NH:20][C:4]1[CH:3]=[C:2]([CH3:1])[N:7]=[C:6]2[N:8]([C:11]3[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=3[CH3:19])[CH:9]=[N:10][C:5]=12

Participants

3

Reactant 1

HCID 22034148N-[5-methyl-3-(2,4,6-trimethylphenyl)imidazolo[5,4-b]pyridin-7-yl]-2-chloroacetamide

Product 1

HCID 22034143(2-Chloroethyl)[5-methyl-3-(2,4,6-trimethylphenyl)imidazolo[5,4-b]pyridin-7-yl]-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Treat a solution of N-[5-methyl-3-(2,4,6-trimethylphenyl)imidazolo[5,4-b]pyridin-7-yl]-2-chloroacetamide (0.04 g, 0.10 mmol) in THF (5 mL) with borane-methyl sulfide complex (0.03 mL, 0.30 mmol). Heat the mixture to reflux for 8 h and quench at ambient temperature with a large excess of MeOH, followed by 6 N HCl (2 mL). Re-heat the mixture to reflux for 1 h, then concentrate under reduced pressure to obtain the title compound as a yellow solid.

Workup

  1. temperatureHeat the mixture
  2. temperatureto reflux for 8 h
  3. customquench at ambient temperature with a large excess of MeOH
  4. temperatureRe-heat the mixture to reflux for 1 h
  5. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-32098465e73249de9fd244508618477c
Source dataset
uspto-grants-2004_02
Patent number
US06696445B2

Reaction notes

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