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

HRID 890872노트

반응식

HRID 890872 반응식
Cl[C:2]1[O:3][C:4]([C:13]2[CH:18]=[CH:17][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.[CH3:23]N(C=O)C.C(=O)([O-])[O-].[K+].[K+].[OH:34][C:35]1[CH:36]=[C:37]([CH:41]2[CH2:46][CH:45]([O:47][CH3:48])C[CH2:43][O:42]2)[CH:38]=[CH:39][CH:40]=1>C(OCC)(=O)C>[CH3:43][O:42][C:41]1([C:37]2[CH:36]=[C:35]([CH:40]=[CH:39][CH:38]=2)[O:34][C:2]2[O:3][C:4]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)=[C:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[N:6]=2)[CH2:46][CH2:45][O:47][CH2:48][CH2:23]1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 222460994-(2-Chloro-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-7ffe14c148084c608e2abdde8f6d460f
출처 데이터셋
uspto-grants-2006_02
특허 번호
US06998415B2

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