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

HRID 427482노트

반응식

HRID 427482 반응식
[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]

참가 물질

6

반응물 3

HCID 8028TetrahydrofuranHCID 4148881Lithium borohydride3회HCID 18357437Ethyl 6-(aminocarbonyl)-8-(2-ethyl-6-methylbenzylamino)-2-methylimidazo[1,2-a]pyridine-3-carboxylate

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매3회HCID 962Water용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-feaf4d957cc14c3b8d545d41070b4a4c
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313137B1

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