Dimethyl-1,3-thiazole-5-carboxylic acid → HCID 66643633, 화합물

HRID 1923600노트

반응식

HRID 1923600 반응식
[CH3:1][C:2]1[S:3][C:4]([C:8]([OH:10])=[O:9])=[C:5]([CH3:7])[N:6]=1.[Li]CCCC.[F:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[C:27]([CH:28]=[O:29])=[CH:26][O:25][N:24]=2)=[N:21][CH:22]=1>C1COCC1>[F:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[C:27]([CH:28]([OH:29])[CH2:1][C:2]3[S:3][C:4]([C:8]([OH:10])=[O:9])=[C:5]([CH3:7])[N:6]=3)=[CH:26][O:25][N:24]=2)=[N:21][CH:22]=1

참가 물질

5

반응물 3

HCID 736488Dimethyl-1,3-thiazole-5-carboxylic acidHCID 866472733-(5-Fluoro-pyridin-2-yl)-isoxazole-4-carbaldehydeHCID 178418339Butyllithium

생성물 1

HCID 66643633HCID 66643633, 화합물수율 55.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a stirred solution of 2,4-dimethyl-thiazole-5-carboxylic acid (1.36 g, 8.63 mmol) in THF (72 mL) at −70° C. and under argon was added BuLi (1.6M in hexanes, 10.8 mL, 17.27 mmol) dropwise. After 2 h a solution of 3-(5-fluoro-pyridin-2-yl)-isoxazole-4-carbaldehyde (1.78 g, 8.63 mmol) in THF (26 mL) was added dropwise. After 1 h the reaction mixture was quenched with citric acid solution (5%, 55 mL) then warmed to room temperature and extracted with ethyl acetate. The combined extracts were washed with brine, water, dried over sodium sulfate, filtered and concentrated. Purification by recrystallization (ethyl acetate) afforded the title compound (1.67 g, 55%) as a light yellow solid. MS: m/e=348.2 [M−H]−.

후처리

  1. customAfter 1 h the reaction mixture was quenched with citric acid solution (5%, 55 mL)
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with brine, water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification
  8. customby recrystallization (ethyl acetate)

출처 및 근거

ORD 기록
ord-6fc7042321a643418103ddab87af1d3e
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178522B2

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