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Water → HCID 178495715, 화합물

HRID 548768
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HRID 548768 반응식
[OH:1][C:2]1[CH:3]=[C:4]([C:14]([NH:16][C:17]2[CH:21]=[CH:20][N:19](C(OC(C)(C)C)=O)[N:18]=2)=[O:15])[CH:5]=[C:6]([O:8][C@@H:9]([CH3:13])[CH2:10][O:11][CH3:12])[CH:7]=1.F[C:30]1[CH:35]=[C:34](F)[C:33]([F:37])=[CH:32][C:31]=1[S:38]([CH:41]1[CH2:45][CH2:44][O:43]C1=O)(=[O:40])=[O:39].C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[F:37][C:33]1[C:34]([O:1][C:2]2[CH:3]=[C:4]([CH:5]=[C:6]([O:8][C@@H:9]([CH3:13])[CH2:10][O:11][CH3:12])[CH:7]=2)[C:14]([NH:16][C:17]2[CH:21]=[CH:20][NH:19][N:18]=2)=[O:15])=[CH:35][C:30]2[O:43][CH2:44][CH2:45][CH2:41][S:38](=[O:40])(=[O:39])[C:31]=2[CH:32]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 576631723-[(2,4,5-trifluorophenyl)sulfonyl]dihydrofuran-2(3H)-oneHCID 59127185tert-Butyl 3-({3-hydroxy-5-[(1S)-2-methoxy-1-methylethoxy]benzoyl}amino)-1H-pyrazole-1-carboxylate

생성물 1

HCID 178495715HCID 178495715, 화합물수율 22.9%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

1,1-Dimethylethyl 3-{[(3-hydroxy-5-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}phenyl) carbonyl]amino}-1H-pyrazole-1-carboxylate (145 mg, 0.5 mmol), 3-[(2,4,5-trifluorophenyl)sulfonyl]dihydrofuran-2(3H)-one (140 mg, 0.5 mmol) and potassium carbonate (138 mg, 2 mmol) in acetonitrile (4 mL) were heated at 130° C. for 1 hour then 160° C. for a further 1 hour in a microwave reactor. Water was added to the reaction mixture and the phases separated. The aqueous phase was extracted with ethyl acetate (3×20 mL), and the combined organics washed with 1M hydrochloric acid, a saturated sodium bicarbonate solution, brine, dried (MgSO4), filtered and evaporated. The residue was chromatographed on alumina, eluting with 0-10% methanol in DCM, to give the desired compound as a white solid (58 mg).

후처리

  1. customthe phases separated
  2. extractionThe aqueous phase was extracted with ethyl acetate (3×20 mL)
  3. washthe combined organics washed with 1M hydrochloric acid
  4. dry with materiala saturated sodium bicarbonate solution, brine, dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was chromatographed on alumina
  8. washeluting with 0-10% methanol in DCM

출처 및 근거

ORD 기록
ord-8ccc8d13c7724b589a92cb1582f18f83
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07943607B2

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