Tetrahydrofuran → ethyl 1-(3-chloro-2-pyridinyl)-3-isopropyl-1H-pyrazole-5-carboxylate

HRID 251952

反応式

HRID 251952 の反応式
CON=[C:4]([CH2:10][C:11](=O)[CH:12]([CH3:14])[CH3:13])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[Cl:16][C:17]1[C:18]([NH:23][NH2:24])=[N:19][CH:20]=[CH:21][CH:22]=1.O1CCCC1>C(O)(=O)C>[Cl:16][C:17]1[C:18]([N:23]2[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:10][C:11]([CH:12]([CH3:13])[CH3:14])=[N:24]2)=[N:19][CH:20]=[CH:21][CH:22]=1

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 5561003-Chloro-2-hydrazinylpyridineHCID 86632548Ethyl 2-methoxyimino-5-methyl-4-oxohexanoate

生成物 1

HCID 66855071ethyl 1-(3-chloro-2-pyridinyl)-3-isopropyl-1H-pyrazole-5-carboxylate収率 26.1%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A mixture of 3.0 g of ethyl 2-methoxyimino-5-methyl-4-oxohexanoate, 2.4 g of 3-chloro-2-hydrazinopyridine, 50 ml of tetrahydrofuran and 100 ml of acetic acid was stirred at room temperature for 20 hours, and then heated to reflux for 4 hours. The reaction mixture was concentrated under reduced pressure. Water was poured into the residue, and the mixture was extracted with methyl t-butyl ether two times. The combined organic layer was washed successively with a 1N aqueous sodium hydroxide solution, water and an aqueous saturated chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 1.07 g of ethyl 1-(3-chloro-2-pyridinyl)-3-isopropyl-1H-pyrazole-5-carboxylate of the formula:

後処理

  1. temperatureheated
  2. temperatureto reflux for 4 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionWater was poured into the residue
  5. extractionthe mixture was extracted with methyl t-butyl ether two times
  6. washThe combined organic layer was washed successively with a 1N aqueous sodium hydroxide solution, water
  7. dry with materialan aqueous saturated chloride solution, dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-07f466220d5d42fd845d237452580c95
出典データセット
uspto-grants-2011_01
特許番号
US07867949B2

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