Dimethylformamide → HCID 69585794, 화합물

HRID 889896노트

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HRID 889896 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11](=[S:13])[NH2:12])[S:10][C:3]=12.CN(C=O)C.Cl[CH:20]([C:26]([CH3:28])=O)[C:21]([O:23][CH2:24][CH3:25])=[O:22]>C1COCC1>[CH2:24]([O:23][C:21]([C:20]1[S:13][C:11]([C:9]2[S:10][C:3]3[C:4](=[N:5][CH:6]=[CH:7][C:2]=3[Cl:1])[CH:8]=2)=[N:12][C:26]=1[CH3:28])=[O:22])[CH3:25]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 11858Ethyl 2-chloroacetoacetateHCID 235951097-Chlorothieno[3,2-b]pyridine-2-carbothioamide

생성물 1

HCID 69585794HCID 69585794, 화합물수율 54%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
80 °C

실험 절차

19.5 g (85.6 mmol) of 7-chloro-thieno[3,2-b]pyridine-2-carbothioic acid amide was added to 160 mL of a 1:1 DMF:THF solution mixture and cooled to 0° C. To this solution was slowly added 17.7 mL (128 mmol) of ethyl 2-chloroacetoacetate. After addition, the reaction was heated to 80° C. for sixteen hours. The reaction was cooled to room temperature and extracted with dichloromethane and water. The organic layer was separated and dried over magnesium sulfate, filtered, concentrated and purified by silica gel chromatography to afford 2-(7-Chloro-thieno[3,2-b]pyridin-2-yl)-4-methyl-thiazole-5-carboxylic acid ethyl ester (15.6 g) in 54% yield. C14H11ClN2O2S2: APCI m/z 339.1/341.0 (pos.); 1H NMR (CDCl3): δ 8.68 (d, 1H , J=5.4 Hz), 8.24 (s, 1H), 7.51 (d, 1H, J=5.4 Hz), 4.36 (q, 2H, J=7.1 Hz), 2.77 (s, 3H), 1.38 (t, 3H, J=7.1 Hz) ppm.

후처리

  1. additionAfter addition
  2. temperatureThe reaction was cooled to room temperature
  3. extractionextracted with dichloromethane and water
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by silica gel chromatography

출처 및 근거

ORD 기록
ord-ae94746106f24abbab2665600e567b57
출처 데이터셋
uspto-grants-2006_02
특허 번호
US06995171B2

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