Tetrahydrofuran → 4-(Imidazo[1,2-b]pyridazin-3-yl)-5-methylthiophene-2-carboxylic acid

HRID 2046403노트

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HRID 2046403 반응식
[N:1]1[CH:2]=[C:3]([C:10]2[CH:11]=[C:12]([C:16]([O:18]C)=[O:17])[S:13][C:14]=2[CH3:15])[N:4]2[C:9]=1[CH:8]=[CH:7][CH:6]=[N:5]2.C1COCC1.[OH-].[K+]>CO>[N:1]1[CH:2]=[C:3]([C:10]2[CH:11]=[C:12]([C:16]([OH:18])=[O:17])[S:13][C:14]=2[CH3:15])[N:4]2[C:9]=1[CH:8]=[CH:7][CH:6]=[N:5]2

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 58046374Methyl 4-(imidazo[1,2-b]pyridazin-3-yl)-5-methylthiophene-2-carboxylate

생성물 1

HCID 580464044-(Imidazo[1,2-b]pyridazin-3-yl)-5-methylthiophene-2-carboxylic acid

시약·촉매·용매 1

HCID 887Methanol용매2회

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온도
60 °C

실험 절차

Methyl 4-(imidazo[1,2-b]pyridazin-3-yl)-5-methylthiophene-2-carboxylate (0.54 g, 1.98 mmol) was dissolved in methanol (9.88 mL) and THF (9.88 mL) and a solution of KOH in methanol was added (1 M, 5.93 mL, 5.93 mmol). The reaction mixture was left to stir overnight at 60° C. The reaction mixture was then cooled to room temperature, concentrated, and acidified with aqueous 1N HCl. The aqueous layer was extracted three times with ethyl acetate, then extracted one time with a 3:1 CHCl3:isopropanol mixture. The combined organics were dried with magnesium sulfate, filtered, and concentrated to afford the title compound. 1H NMR (500 MHz, CD3SOCD3) δ 8.77 (d, 1H); 8.34 (d, 1H); 8.25 (s, 1H); 8.11 (s, 1H); 7.51 (dd, 1H); 2.56 (s, 3H). LRMS (APCI) calc'd for (C12H9N3O2S) [M+H]+, 260.0. found 260.0.

후처리

  1. waitThe reaction mixture was left
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. concentrationconcentrated
  4. extractionThe aqueous layer was extracted three times with ethyl acetate
  5. extractionextracted one time with a 3:1 CHCl3
  6. dry with materialThe combined organics were dried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a4700d4c094d4b6fbeae3b65e75c56c4
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08592425B2

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