Sodium Bicarbonate → HCID 9842936, 화합물

HRID 1166402노트

반응식

HRID 1166402 반응식
CC1[N:3]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:21][CH:20]([C:22]([F:25])([F:24])[F:23])[N:19]=[C:18]3[C:26]3[C:27]([CH3:32])=[N:28][CH:29]=[CH:30][CH:31]=3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])C(C)=CC=1.C(=O)(O)[O-].[Na+]>C(O)(C(F)(F)F)=O.O>[CH3:32][C:27]1[C:26]([C:18]2[N:17]([C:14]3[CH:15]=[CH:16][C:11]([S:8]([NH2:3])(=[O:10])=[O:9])=[CH:12][CH:13]=3)[CH:21]=[C:20]([C:22]([F:23])([F:24])[F:25])[N:19]=2)=[CH:31][CH:30]=[CH:29][N:28]=1

참가 물질

5

반응물 2

HCID 516892Sodium BicarbonateHCID 22997798HCID 22997798, 화합물

생성물 1

HCID 9842936HCID 9842936, 화합물수율 78.5%

시약·촉매·용매 2

HCID 962Water용매2회HCID 6422Trifluoroacetic acid용매

실험 절차

A mixture of 3-[1-[4-[(2,5-dimethyl-1H-pyrrol-1-yl)sulfonyl]phenyl]-4,5-dihydro-4-(trifluoromethyl)-1H-imidazol-2-yl]-2-methylpyridine (Step 4) (4.6 g, 0.01 mol) in 75 mL of TFA and 25 mL of water was heated at reflux for 2 hours. The solution was cooled, treated with 400 mL of water and basified with sodium bicarbonate to pH 8. The aqueous phase was extracted with ethyl acetate (400 mL). The organic layer was washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated and the crude was purified by chromatography on silica gel (ethyl acetate/acetone, 95:5) to afford 4-[2-(2-methylpyridin-3-yl)-4-(trifluoromethyl)-1H-imidazol-1-yl]benzenesulfonamide as a white solid (3.0 g, 78%): mp (DSC): 235-237° C. Anal. Calc'd. for C16H13F3N3O2S: C, 50.26; H, 3.43; N, 14.65; S, 8.39. Found: C, 50.06; H,3.29; N, 14.4; S, 8.52.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. temperatureThe solution was cooled
  4. extractionThe aqueous phase was extracted with ethyl acetate (400 mL)
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated
  9. customthe crude was purified by chromatography on silica gel (ethyl acetate/acetone, 95:5)

출처 및 근거

ORD 기록
ord-baa3ebc49bfd4b6faf8ede6b7f40570a
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06613789B2

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