HCID 22034146, compound → HCID 22034141, compound

HRID 2121606Notes

Reaction equation

HRID 2121606 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]2=[N:14][C:15]([CH3:23])=[CH:16][C:17]([NH:18][C:19](=O)[CH2:20][Cl:21])=[C:12]2[N:11]=[C:10]1[CH3:24]>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]2=[N:14][C:15]([CH3:23])=[CH:16][C:17]([NH:18][CH2:19][CH2:20][Cl:21])=[C:12]2[N:11]=[C:10]1[CH3:24]

Participants

3

Reactant 1

HCID 22034146HCID 22034146, compound

Product 1

HCID 22034141HCID 22034141, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Treat a solution of N-[3-(2,4-dichlorophenyl)-2,5-dimethylimidazolo[5,4-b]pyridin-7-yl]-2-chloroacetamide (1.0 g, 2.6 mmol) in THF (5 mL) with borane-methyl sulfide complex (0.8 mL, 7.8 mmol). Heat the mixture to reflux for 3 h and quench at ambient temperature with a large excess of MeOH followed by 5 N HCl (2 mL). Re-heat the mixture to reflux for 1 h, then concentrate under reduced pressure. Purify by flash column chromatography (50% EtOAc-hexane) to obtain the title compound as a beige solid.

Workup

  1. temperatureHeat the mixture
  2. temperatureto reflux for 3 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
  6. customPurify by flash column chromatography (50% EtOAc-hexane)

Sources & evidence

ORD record
ord-0800d3594e7d452391c752d51a8c70d5
Source dataset
uspto-grants-2004_02
Patent number
US06696445B2

Reaction notes

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