Tetrahydrofuran → HCID 60169173, 화합물

HRID 1518735노트

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HRID 1518735 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([C:13](N(OC)C)=[O:14])=[C:10]([C:19]3[CH:24]=[CH:23][C:22]([S:25](=[O:32])(=[O:31])[N:26]=CN(C)C)=[C:21]([CH3:33])[CH:20]=3)[C:9]=2[CH3:34])=[CH:4][CH:3]=1.[CH2:35]1COC[CH2:36]1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([C:13](=[O:14])[CH2:35][CH3:36])=[C:10]([C:19]3[CH:24]=[CH:23][C:22]([S:25]([NH2:26])(=[O:31])=[O:32])=[C:21]([CH3:33])[CH:20]=3)[C:9]=2[CH3:34])=[CH:4][CH:3]=1

참가 물질

3

반응물 2

HCID 8028TetrahydrofuranHCID 86705033HCID 86705033, 화합물

생성물 1

HCID 60169173HCID 60169173, 화합물수율 18.1%

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온도
0 °C

실험 절차

Grignard reagent (Ethyl magnesium bromide, 0.42 g, 3.17 ml 1M solution in THF, 3.17 mmol) was added drop wise to a stirred solution of (5-(4-chlorophenyl)-3-(4-(N-((dimethylamino)methylene)sulfamoyl)-3-methylphenyl)-N-methoxy-N,4-dimethylthiophene-2-carboxamide (41e, 0.33 g, 0.63 mmol) in anhydrous THF (20 ml) at 25° C. The reaction mixture was then heated to about 70° C. to 75° C. for 1 hr. The progress of the reaction was monitored by TLC. The reaction mixture was then cooled to 0° C. The cooled reaction mixture was quenched by adding saturated solution of ammonium chloride (10 ml) and the mixture was then extracted with ethyl acetate (2×30 ml). The combined organic layer was dried over anhydrous Na2SO4. The solvent was evaporated from the dried organic layer under reduced pressure to obtain a crude product, which was then purified by preparative HPLC to obtain the title compound (0.05 g, 18.1%)

후처리

  1. temperatureThe reaction mixture was then heated to about 70° C. to 75° C. for 1 hr
  2. customThe cooled reaction mixture
  3. customwas quenched
  4. additionby adding saturated solution of ammonium chloride (10 ml)
  5. extractionthe mixture was then extracted with ethyl acetate (2×30 ml)
  6. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  7. customThe solvent was evaporated from the dried organic layer under reduced pressure
  8. customto obtain a crude product, which
  9. customwas then purified by preparative HPLC

출처 및 근거

ORD 기록
ord-f8f6ecdf94cb488e84f96e5f8da19d68
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09072731B2

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