Sodium Methoxide → N-cyclopropyl-5-fluoro4'-[5-(methoxymethyl)-1,3,4-oxadiazol-2-yl]-6-methyl-1,1'-biphenyl-3-carboxamide

HRID 31467노트

반응식

HRID 31467 반응식
[CH3:1][O-:2].[Na+].Cl[CH2:5][C:6]1[O:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[C:22]([CH3:23])=[C:21]([F:24])[CH:20]=[C:19]([C:25]([NH:27][CH:28]4[CH2:30][CH2:29]4)=[O:26])[CH:18]=3)=[CH:13][CH:12]=2)=[N:8][N:7]=1>CO>[CH:28]1([NH:27][C:25]([C:19]2[CH:18]=[C:17]([C:14]3[CH:15]=[CH:16][C:11]([C:9]4[O:10][C:6]([CH2:5][O:2][CH3:1])=[N:7][N:8]=4)=[CH:12][CH:13]=3)[C:22]([CH3:23])=[C:21]([F:24])[CH:20]=2)=[O:26])[CH2:30][CH2:29]1

참가 물질

4

반응물 2

HCID 10942334Sodium Methoxide2회HCID 693149174'-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-5-fluoro-6-methyl-1,1'-biphenyl-3-carboxamide2회

생성물 1

HCID 10317702N-cyclopropyl-5-fluoro4'-[5-(methoxymethyl)-1,3,4-oxadiazol-2-yl]-6-methyl-1,1'-biphenyl-3-carboxamide

시약·촉매·용매 1

HCID 887Methanol용매3회

실험 절차

Freshly prepared sodium methoxide in methanol (0.2M, 0.8 ml) was added to a solution of (4′-[5-chloromethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-5-fluoro-6-methyl-1,1′-biphenyl-3-carboxamide (Intermediate 34) (50 mg) in methanol (1 ml) and the reaction stirred at room temperature for 18 hours. Further sodium methoxide in methanol (0.2M, 1.6 ml) was added and the reaction continued for 72 hours. The reaction was reduced to dryness under vacuum and the residue partitioned between ethyl acetate and water. The organic phase was reduced to dryness and loaded onto a bond-elut (silica, 10 g). Eluted with an ethyl acetate/cyclohexane gradient. The solvent was evaporated from the product fractions under vacuum to give N-cyclopropyl-5-fluoro4′-[5-(methoxymethyl)-1,3,4-oxadiazol-2-yl]-6-methyl-1,1′-biphenyl-3-carboxamide.

후처리

  1. waitthe reaction continued for 72 hours
  2. customthe residue partitioned between ethyl acetate and water
  3. washEluted with an ethyl acetate/cyclohexane gradient
  4. customThe solvent was evaporated from the product fractions under vacuum

출처 및 근거

ORD 기록
ord-5a6be07d112d4df9a703a6ea1848b3aa
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425555B2

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