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

HRID 2121602Notes

Reaction equation

HRID 2121602 reaction equation
[CH3:1][C:2]1[N:3]([C:17]2[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=2[CH3:25])[C:4]2[C:9]([N:10]=1)=[C:8]([NH:11][C:12](=O)[CH2:13][Cl:14])[CH:7]=[C:6]([CH3:16])[N:5]=2>C1COCC1>[CH3:1][C:2]1[N:3]([C:17]2[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=2[CH3:25])[C:4]2[C:9]([N:10]=1)=[C:8]([NH:11][CH2:12][CH2:13][Cl:14])[CH:7]=[C:6]([CH3:16])[N:5]=2

Participants

3

Reactant 1

HCID 22034101N-[2,5-Dimethyl-3-(2,4,6-trimethylphenyl)imidazolo[5,4-b]pyridin-7-yl]-2-chloroacetamide

Product 1

HCID 22034113[2,5-Dimethyl-3-(2,4,6-trimethylphenyl)imidazolo[5,4-b]pyridin-7-yl](2-chloroethyl)amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Treat a solution of N-[2,5-dimethyl-3-(2,4,6-trimethylphenyl)imidazolo[5,4-b]pyridin-7-yl]-2-chloroacetamide (0.91 g, 2.55 mmol) in THF (5 mL) with borane-methyl sulfide complex (0.8 mL, 7.65 mmol). Heat the mixture to reflux for 18 h and quench at ambient temperature with a large excess of MeOH, followed by 6N HCl (5 mL). Re-heat the mixture to reflux for 1 h, then concentrate under reduced pressure to obtain the title compound as a white crystalline solid.

Workup

  1. temperatureHeat the mixture
  2. temperatureto reflux for 18 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-8a48dec01a344d86bf5f177555147553
Source dataset
uspto-grants-2004_02
Patent number
US06696445B2

Reaction notes

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