Ethanol → Methyl 4-cyclopropyl-5-(3H-imidazo[4,5-c]pyridin-2-yl)-2-methylbenzoate

HRID 1487970노트

반응식

HRID 1487970 반응식
[CH:1]1([C:4]2[C:13]([CH:14]=O)=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([CH3:16])[CH:5]=2)[CH2:3][CH2:2]1.[N:17]1[CH:22]=[CH:21][C:20]([NH2:23])=[C:19]([NH2:24])[CH:18]=1.C(O)C>C(=O)(O)[O-].[Na+]>[CH:1]1([C:4]2[C:13]([C:14]3[NH:24][C:19]4[CH:18]=[N:17][CH:22]=[CH:21][C:20]=4[N:23]=3)=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([CH3:16])[CH:5]=2)[CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 702EthanolHCID 59183,4-DiaminopyridineHCID 90021238Methyl 4-cyclopropyl-5-formyl-2-methylbenzoate2회

생성물 1

HCID 90021751Methyl 4-cyclopropyl-5-(3H-imidazo[4,5-c]pyridin-2-yl)-2-methylbenzoate수율 38.1%

시약·촉매·용매 1

HCID 516892Sodium Bicarbonate용매

반응 조건

온도
70 °C

실험 절차

Into a 100-mL round-bottom flask was placed a mixture of methyl 4-cyclopropyl-5-formyl-2-methylbenzoate (compound 87.1, 500 mg, 2.29 mmol), pyridine-3,4-diamine (500 mg, 4.58 mmol), NH4OAc (1.42 g, 18.4 mmol) and ethanol (50 mL). The resulting mixture was stirred open to the air for 3 days at 70° C., then cooled to room temperature and diluted with aqueous sodium bicarbonate (sat., 50 mL). The aqueous phase was extracted with ethyl acetate (2×50 mL) and the combined organic layers were dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with ethyl acetate as the eluent to yield 268 mg (38%) of the title compound as a yellow semi-solid.

후처리

  1. customInto a 100-mL round-bottom flask was placed
  2. temperaturecooled to room temperature
  3. extractionThe aqueous phase was extracted with ethyl acetate (2×50 mL)
  4. dry with materialthe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography with ethyl acetate as the eluent

출처 및 근거

ORD 기록
ord-0f440eda1935477abfbf00d5a05b26d0
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09428502B2

반응 노트

불러오는 중…