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

HRID 1487970ノート

反応式

HRID 1487970 の反応式
[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

参加物

5

反応物 3

HCID 702EthanolHCID 59183,4-DiaminopyridineHCID 90021238Methyl 4-cyclopropyl-5-formyl-2-methylbenzoate2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
70 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0f440eda1935477abfbf00d5a05b26d0
出典データセット
uspto-grants-2016_08
特許番号
US09428502B2

反応ノート

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