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5-Thiazolecarboxylic acid, 2-methyl- → 2-{2-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-2-hydroxy-ethyl}-thiazole-5-carboxylic acid

HRID 1923581
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HRID 1923581 반응식
[CH3:1][C:2]1[S:3][C:4]([C:7]([OH:9])=[O:8])=[CH:5][N:6]=1.[Li]CCCC.[F:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]2[C:26]([CH:27]=[O:28])=[C:25]([CH3:29])[O:24][N:23]=2)=[N:20][CH:21]=1>C1COCC1>[F:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]2[C:26]([CH:27]([OH:28])[CH2:1][C:2]3[S:3][C:4]([C:7]([OH:9])=[O:8])=[CH:5][N:6]=3)=[C:25]([CH3:29])[O:24][N:23]=2)=[N:20][CH:21]=1
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참가 물질

5

반응물 3

HCID 988455-Thiazolecarboxylic acid, 2-methyl-HCID 866472723-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazole-4-carbaldehydeHCID 178418339Butyllithium

생성물 1

HCID 666436562-{2-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-2-hydroxy-ethyl}-thiazole-5-carboxylic acid수율 66%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매
2회

실험 절차

To a stirred solution of 2-methyl-thiazole-5-carboxylic acid (1.15 g, 8.05 mmol) in THF (67 mL) at −70° C. and under argon was added BuLi (1.6M in hexanes, 10.06 mL, 16.1 mmol) dropwise. After 2 h a solution of 3-(5-fluoro-pyridin-2-yl)-5-methyl-isoxazole-4-carbaldehyde (1.66 g, 8.05 mmol) in THF (24 mL) was added dropwise. After 3 h the reaction mixture was quenched with citric acid solution (5%, 50 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 trituration (ethyl acetate) afforded the title compound (1.85 g, 66%) as a light yellow solid. MS: m/e=348.2 [M−H]−.

후처리

  1. customAfter 3 h the reaction mixture was quenched with citric acid solution (5%, 50 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 by trituration (ethyl acetate)

출처 및 근거

ORD 기록
ord-70c6b216fa2e4510bec1273ad2f673ea
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08178522B2

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