Dimethyl-1,3-thiazole-5-carboxylic acid → HCID 67495517、化合物

HRID 2365238ノート

反応式

HRID 2365238 の反応式
[CH3:1][C:2]1[S:3][C:4]([C:8]([OH:10])=[O:9])=[C:5]([CH3:7])[N:6]=1.[Li]CCCC.[CH3:16][N:17]1[C:21]([CH:22]=[O:23])=[C:20]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)[N:19]=[N:18]1>C1COCC1>[OH:23][CH:22]([C:21]1[N:17]([CH3:16])[N:18]=[N:19][C:20]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1)[CH2:1][C:2]1[S:3][C:4]([C:8]([OH:10])=[O:9])=[C:5]([CH3:7])[N:6]=1

参加物

5

反応物 3

HCID 736488Dimethyl-1,3-thiazole-5-carboxylic acidHCID 86664842HCID 86664842、化合物HCID 178418339Butyllithium

生成物 1

HCID 67495517HCID 67495517、化合物収率 83.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-75 °C

実験手順

To a suspension of 2,4-dimethylthiazole-5-carboxylic acid (157 mg, 1.0 mmol) in THF (8 mL) was added dropwise n-BuLi (1.6 M in hexanes, 1.25 mL, 2.0 mmol) under Ar at −75° C. The brown suspension was stirred at −75° C. for 2 h and then a solution of 3-methyl-5-pyridin-2-yl-3H-[1,2,3]triazole-4-carbaldehyde (188 mg, 1.0 mmol) in THF (3 mL) was added at −75° C. and the brown suspension was stirred at −75° C. for 2 h. The mixture was then quenched with an aqueous solution of citric acid (5%, 10 mL), allowed to warm to room temperature. The mixture was then poured into saturated ammonium chloride solution and extracted with ethyl acetate and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated. Purification by recrystallisation from ethylacetate-heptane afforded the title compound (288 mg, 83%) as a light red solid. MS: m/e=344.0 [M−H]−.

後処理

  1. stirringthe brown suspension was stirred at −75° C. for 2 h
  2. customThe mixture was then quenched with an aqueous solution of citric acid (5%, 10 mL)
  3. temperatureto warm to room temperature
  4. additionThe mixture was then poured into saturated ammonium chloride solution
  5. extractionextracted with ethyl acetate
  6. washthe combined organic extracts washed with brine
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltered
  9. customevaporated
  10. customPurification
  11. customby recrystallisation from ethylacetate-heptane

出典と根拠

ORDレコード
ord-583922f8c6a04cf5b1f626b46a4fdfd2
出典データセット
uspto-grants-2014_04
特許番号
US08697696B2

反応ノート

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