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

HRID 222360ノート

反応式

HRID 222360 の反応式
[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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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]−.

後処理

  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

出典と根拠

ORDレコード
ord-c0c8247c40c7416f92070886877d5e7a
出典データセット
uspto-grants-2012_06
特許番号
US08207205B2

反応ノート

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