Sodium borohydride → HCID 23287283, compound

HRID 862555Notes

Reaction equation

HRID 862555 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]([NH:8][C:9]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:10]=1[CH2:11][NH:12][C:13]1[C:14]2[N:15]([C:19]([CH:23]=[O:24])=[C:20]([CH3:22])[N:21]=2)[CH:16]=[CH:17][CH:18]=1)=[O:7].[BH4-].[Na+]>CO>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]([NH:8][C:9]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:10]=1[CH2:11][NH:12][C:13]1[C:14]2[N:15]([C:19]([CH2:23][OH:24])=[C:20]([CH3:22])[N:21]=2)[CH:16]=[CH:17][CH:18]=1)=[O:7]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 19698534HCID 19698534, compound

Product 1

HCID 23287283HCID 23287283, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.8 g (7.06 mmol) of 8-{2-[(2-methoxyethoxy)carbonylamino]-6-methylbenzylamino}-2-methylimidazo[1,2-a]-pyridine-3-carboxaldehyde are reduced with sodium borohydride analogously to Example 2, methanol is distilled off in vacuo, and the residue is treated with water and ethyl acetate and adjusted to pH 9 using potassium hydrogen phosphate solution. The mixture is extracted several times with ethyl acetate, dried and concentrated in vacuo, and the residue is recrystallized from toluene/diisopropyl ether. 2.28 g (81%) of the title compound of m.p. 138°-140° C. are obtained.

Workup

  1. distillationis distilled off in vacuo
  2. additionthe residue is treated with water and ethyl acetate
  3. extractionThe mixture is extracted several times with ethyl acetate
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customthe residue is recrystallized from toluene/diisopropyl ether

Sources & evidence

ORD record
ord-f45a7163839643ad8198e5f2ef91d9b8
Source dataset
uspto-grants-1998_02
Patent number
US05719161

Reaction notes

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