Methanol → 3-Carboethoxy-2,6-dimethyl-8-(2-ethyl-6-methylbenzylamino)imidazo[1,2-a]pyridine

HRID 1386089노트

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HRID 1386089 반응식
[NH2:1][C:2]1[C:3]2[N:4]([C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:10]([CH3:12])[N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[CH2:18]([C:20]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:21]=1[CH:22]=O)[CH3:19].CO>[Cl-].[Cl-].[Zn+2].C(N(CC)CC)C>[C:13]([C:9]1[N:4]2[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([NH:1][CH2:22][C:21]3[C:24]([CH3:28])=[CH:25][CH:26]=[CH:27][C:20]=3[CH2:18][CH3:19])[C:3]2=[N:11][C:10]=1[CH3:12])([O:15][CH2:16][CH3:17])=[O:14]

참가 물질

6

반응물 3

HCID 887MethanolHCID 226725728-Amino-3-carboethoxy-2,6-dimethylimidazo[1,2-a]pyridineHCID 229974692-Ethyl-6-methylbenzaldehyde

생성물 1

HCID 217173483-Carboethoxy-2,6-dimethyl-8-(2-ethyl-6-methylbenzylamino)imidazo[1,2-a]pyridine수율 50.2%

시약·촉매·용매 2

HCID 3007855Zincchloride촉매2회HCID 8471Triethylamine용매

실험 절차

A mixture of 8-amino-3-carboethoxy-2,6-dimethylimidazo[1,2-a]pyridine (1.4 g, 6 mmol), 2-ethyl-6-methylbenzaldehyde (0.9 g, 6.5 mmol), ZnCl2 (1.0 g, 7.4 mmol), NaB(CN)H3 (0.41 g, 6.5 mmol) and MeOH (30 ml) was refluxed for 5 h. More ZnCl2 (0.2 g) and NaB(CN)H3 (0.1 g) were added. The reaction mixture was refluxed for additional 2 h. Triethylamin (2 ml) was added and the mixture was stirred at R.T for 10 min. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel using methylene chloride as eluent. 1.1 g (50%) of the title compound was obtained.

후처리

  1. temperaturewas refluxed for 5 h
  2. temperatureThe reaction mixture was refluxed for additional 2 h
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-f6ae35be5c554fafaaccebb4ddd260f2
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06265415B1

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