Water → 3-(3,5-Dibromo-4-hydroxyphenyl)-n-ethyl-n-(3-(trifluormethyl)benzyl)-1,2,4-oxadiazole-5-carboxamide

HRID 222360노트

반응식

HRID 222360 반응식
[Br:1][C:2]1[CH:3]=[C:4]([C:19]2[N:23]=[C:22]([C:24]([NH:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=3)=[O:25])[O:21][N:20]=2)[CH:5]=[C:6]([Br:18])[C:7]=1[O:8]CC1C=CC(OC)=CC=1.[CH3:38][C:39](C)([O-])C.[Na+].C(I)C.O>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([C:19]2[N:23]=[C:22]([C:24]([N:26]([CH2:38][CH3:39])[CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=3)=[O:25])[O:21][N:20]=2)[CH:5]=[C:6]([Br:18])[C:7]=1[OH:8]

참가 물질

6

반응물 4

HCID 962WaterHCID 6340IodoethaneHCID 23676156Sodium t-butoxideHCID 579197343-(3,5-Dibromo-4-(4-methoxybenzyloxy)phenyl)-N-(3-(trifluoromethyl)benzyl)-1,2,4-oxadiazole-5-carboxamide

생성물 1

HCID 1358705353-(3,5-Dibromo-4-hydroxyphenyl)-n-ethyl-n-(3-(trifluormethyl)benzyl)-1,2,4-oxadiazole-5-carboxamide수율 32%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

3-(3,5-Dibromo-4-(4-methoxybenzyloxy)phenyl)-N-(3-(trifluoromethyl)benzyl)-1,2,4-oxadiazole-5-carboxamide (128 mg, 0.2 mmol) was dissolved in dimethylformamide (2 mL) and sodium-tert-butoxide (21 mg, 0.22 mmol) was added in one portion followed by ethyl iodide (34 mg, 0.22 mmol). The mixture was stirred at room temperature for 20 h and was then treated with water (8 mL) and extracted with ethyl acetate (4 mL). The extract was evaporated to dryness and the residue was dissolved in dichloromethane (2 mL), trifluoroacetic acid (0.2 mL) was added and the solution was allowed to stand for 1 h. Methanol (0.5 mL) was added, the solution was evaporated to dryness and the residue was purified by preparative HPLC to give the title compound (32.8 mg, 32%) as a colourless solid. 1H NMR δ (ppm) (DMSO-d6): 1.14 and 1.29 (3H, two t), 3.47 and 3.62 (2H, two q), 4.88 and 4.97 (2H, two s), 7.60-7.75 (3H, m), 7.78 and 7.89 (1H, two s), 8.04 and 8.15 (2H, two s), 10.9 (1H, s, br). LCMS (10 cm_apci_formic) tR 4.33 min; m/z 546/548/550 [M−H]−.

후처리

  1. extractionextracted with ethyl acetate (4 mL)
  2. customThe extract was evaporated to dryness
  3. dissolutionthe residue was dissolved in dichloromethane (2 mL)
  4. additiontrifluoroacetic acid (0.2 mL) was added
  5. waitto stand for 1 h
  6. additionMethanol (0.5 mL) was added
  7. customthe solution was evaporated to dryness
  8. customthe residue was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-c0c8247c40c7416f92070886877d5e7a
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207205B2

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