Methanol → HCID 178499252, 화합물

HRID 1190039

반응식

HRID 1190039 반응식
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([Br:19])=[CH:8][C:9]=1[NH:10][CH:11]1[CH2:16][O:15][C:14]([CH3:18])([CH3:17])[O:13][CH2:12]1)=[O:4].N1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[CH3:26]O.C([O:31][CH2:32][CH3:33])(=O)C>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([Br:19])=[CH:8][C:9]=1[N:10]([CH:11]1[CH2:16][O:15][C:14]([CH3:17])([CH3:18])[O:13][CH2:12]1)[C:32]([C@H:33]1[CH2:25][CH2:24][C@H:23]([CH3:26])[CH2:22][CH2:21]1)=[O:31])=[O:4]

참가 물질

6

반응물 4

HCID 887MethanolHCID 1049Pyridine3회HCID 8857Ethyl AcetateHCID 577954295-Bromo-3-(2,2-dimethyl-[1,3]dioxan-5-ylamino)-thiophene-2-carboxylic acid methyl ester

생성물 1

HCID 178499252HCID 178499252, 화합물

시약·촉매·용매 1

HCID 1140Toluene용매4회

반응 조건

온도
5 °C

실험 절차

To a mixture of 5-bromo-3-(2,2-dimethyl-[1,3]dioxan-5-ylamino)-thiophene-2-carboxylic acid methyl ester (200 mg, 0.57 mmol) in toluene (1 mL) and pyridine (100 μl, 1.23 mmol), acid chloride in toluene prepared above (1.1 mL, 1.05 mmol) was added. The reaction mixture was refluxed for 16 h. TLC showed the presence of starting material. Pyridine (50 μl, 0.62 mmol) and acid chloride in toluene (0.5 mL, 0.47 mmol) were added and the refluxing was continued for 24 h. The mixture was cooled to 5° C. Toluene (2 mL) and pyridine (0.2 mL) were added. After stirring for 5 min MeOH (0.5 mL) was added and the mixture was stirred for 10 min. It was diluted with ethyl acetate, washed with saturated NaHCO3 and brine, dried and evaporated. The crude reaction mixture was chromatographed over silica gel (hexane-ethyl acetate mixtures as eluents) yielding 5-bromo-3-[(2,2-dimethyl-[1,3]dioxan-5-yl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester (35 mg) contaminated with a small impurity. This material was used for the next step.

후처리

  1. customprepared above (1.1 mL, 1.05 mmol)
  2. additionwas added
  3. temperatureThe reaction mixture was refluxed for 16 h
  4. additionwas added
  5. washwashed with saturated NaHCO3 and brine
  6. customdried
  7. customevaporated
  8. customThe crude reaction mixture
  9. customwas chromatographed over silica gel (hexane-ethyl acetate mixtures as eluents)

출처 및 근거

ORD 기록
ord-efe3663babf04f7b99b16373e091fedc
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08674118B2

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