Tetrahydrofuran → 8-(2-Ethyl-6-methylbenzylamino)-3-hydroxymethyl-2-methylimidazo(1,2-a)pyridine-6-carboxamide

HRID 427482Notes

Reaction equation

HRID 427482 reaction equation
[NH2:1][C:2]([C:4]1[CH:5]=[C:6]([NH:19][CH2:20][C:21]2[C:26]([CH3:27])=[CH:25][CH:24]=[CH:23][C:22]=2[CH2:28][CH3:29])[C:7]2[N:8]([C:10]([C:14](OCC)=[O:15])=[C:11]([CH3:13])[N:12]=2)[CH:9]=1)=[O:3].[BH4-].[Li+].O1CCCC1>CO.O>[CH2:28]([C:22]1[CH:23]=[CH:24][CH:25]=[C:26]([CH3:27])[C:21]=1[CH2:20][NH:19][C:6]1[C:7]2[N:8]([C:10]([CH2:14][OH:15])=[C:11]([CH3:13])[N:12]=2)[CH:9]=[C:4]([C:2]([NH2:1])=[O:3])[CH:5]=1)[CH3:29]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 4148881Lithium borohydride3×HCID 18357437Ethyl 6-(aminocarbonyl)-8-(2-ethyl-6-methylbenzylamino)-2-methylimidazo[1,2-a]pyridine-3-carboxylate

Product 1

HCID 97985998-(2-Ethyl-6-methylbenzylamino)-3-hydroxymethyl-2-methylimidazo(1,2-a)pyridine-6-carboxamideYield 46%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 962WaterSolvent

Procedure

Ethyl 6-(aminocarbonyl)-8-(2-ethyl-6-methylbenzylamino)-2-methylimidazo[1,2-a]pyridine-3-carboxylate (280 mg, 0.71 mmol) and lithium borohydride (16 mg, 0.71 mmol) were added to tetrahydrofuran (10 ml) and the reaction mixture was refluxed for 70 min. Additional amounts of lithium borohydride (16 mg) and methanol (45 mg, 1.42 mmol) were added and the mixture was refluxed for 80 min. Additional amounts of lithium borohydride (16 mg) and methanol (22 mg, 71 mmol) were added and the mixture was refluxed for 4 h. The reaction mixture was allowed to reach R.T. and water (1 ml) and methanol (5 ml) and was stirred for 40 min. at R.T. The solvents were evaporated under reduced pressure and the residue was added to water and was stirred for 80 min. The crystals were filtered off and washed with water, ethyl acetate/ethanol and diethyl ether to give the desired product (115 mg, 46%).

Workup

  1. temperaturethe reaction mixture was refluxed for 70 min
  2. temperaturethe mixture was refluxed for 80 min
  3. temperaturethe mixture was refluxed for 4 h
  4. customto reach R.T.
  5. customThe solvents were evaporated under reduced pressure
  6. additionthe residue was added to water
  7. filtrationThe crystals were filtered off
  8. washwashed with water, ethyl acetate/ethanol and diethyl ether

Sources & evidence

ORD record
ord-feaf4d957cc14c3b8d545d41070b4a4c
Source dataset
uspto-grants-2001_11
Patent number
US06313137B1

Reaction notes

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