Dimethylformamide → 4-[2-(3-(4-methoxy-3,4,5,6-tetrahydro-2H-pyran-4-yl)phenoxy)-4-phenyl-5-oxazolyl]benzenesulfonamide

HRID 263643노트

반응식

HRID 263643 반응식
F[C:2]1[CH:3]=[C:4]([CH:27]=[C:28]([C:30]2([O:36][CH3:37])[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[CH:29]=1)[O:5][C:6]1[O:7][C:8]([C:17]2[CH:22]=[CH:21][C:20]([S:23]([NH2:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:10]=1.CN(C=O)C.C(=O)([O-])[O-].[K+].[K+].OC1C=C(C2CC(OC)CCO2)C=CC=1>C(OCC)(=O)C>[CH3:37][O:36][C:30]1([C:28]2[CH:27]=[C:4]([CH:3]=[CH:2][CH:29]=2)[O:5][C:6]2[O:7][C:8]([C:17]3[CH:22]=[CH:21][C:20]([S:23]([NH2:26])(=[O:25])=[O:24])=[CH:19][CH:18]=3)=[C:9]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:10]=2)[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 129861264-[2-[3-fluoro-5-(4-methoxy-3,4,5,6-tetrahydro-2H-pyran-4-yl)phenoxy]-4-phenyl-5-oxazolyl]benzenesulfonamideHCID 22246254(3-hydroxyphenyl)-4-methoxy-3,4,5,6-tetrahydro-2H-pyran

생성물 1

HCID 129861274-[2-(3-(4-methoxy-3,4,5,6-tetrahydro-2H-pyran-4-yl)phenoxy)-4-phenyl-5-oxazolyl]benzenesulfonamide수율 44%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

4-[2-Chloro-4-phenyl-5-oxazolyl]benzenesulfonamide from Example 4, Step 3, (0.6 g, 1.8 mmol), DMF (20 mL), potassium carbonate (0.5 g, 3.6 mmol), and 4 (3-hydroxyphenyl)-4-methoxy-3,4,5,6-tetrahydro-2H-pyran (0.37 g, 1.8 mmol) [prepared as described by G. C. Crawley, et al, J. Med. Chem., 35, 2600-2609 (1992)]were stirred at room temperature for 16.0 hours. The solution was diluted with ethyl acetate (100 mL), washed with 1N HCl, brine and water, dried over MgSO4 and concentrated. The residue was dissolved in ethyl acetate/hexanes (1:1) and filtered through silica. The eluant was concentrated and the residue recrystallized from ethyl acetate/hexanes to give 4-[2-[3-(4-methoxy-3,4,5,6-tetrahydro-2H-pyran-4-yl)phenoxy]-4-phenyl-5-oxazolyl]benzenesulfonamide as a white solid (0.4 g, 44%): mp 145°-147° C. 1H NMR (CDCl3) 300 MHz δ 7.88 (d, J=8.9 Hz, 2H) 7.70 (d, J=8.9 Hz, 2H) 7.6 (m, 2H) 7.36-7.5 (m, 6H) 7.0-7.1 (dt, J=6.4 Hz and J=2.2 Hz, 1H) 4.85 (bs, 2H) 3.7 (m, 4H) 3.05 (s, 3H) 2.0 (m, 4H). Anal. Calc'd. for C27H26N2O6S: C, 64.02; H, 5.17; N, 5.53. Found: C, 63.94; H, 5.17; N, 5.55.

후처리

  1. washwashed with 1N HCl, brine and water
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in ethyl acetate/hexanes (1:1)
  5. filtrationfiltered through silica
  6. concentrationThe eluant was concentrated
  7. customthe residue recrystallized from ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-3e0bfd7a473645d8a2cf229fcaa4995e
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05643933

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