Trimethylsilyl cyanide → (3-Methoxy-5-methoxymethylphenyl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile

HRID 2079110

반응식

HRID 2079110 반응식
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)[N:3]=1.F[C:15](F)(F)[C:16]([OH:18])=O.C(C1C=CC(N[CH:31]([C:47]2[CH:52]=[C:51]([O:53][CH3:54])[C:50](OC)=C[C:48]=2F)[C:32]2NC(=O)N(C3C=CC=CC=3C(O)=O)[N:33]=2)=CC=1)(=N)N.[C:58](S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Yb+3].C[Si](C#N)(C)C>ClCCl>[CH3:54][O:53][C:51]1[CH:52]=[C:47]([CH:31]([NH:13][C:10]2[CH:11]=[CH:12][C:7]([C:4]3[N:3]=[C:2]([CH3:1])[O:6][N:5]=3)=[CH:8][CH:9]=2)[C:32]#[N:33])[CH:48]=[C:15]([CH2:16][O:18][CH3:58])[CH:50]=1

참가 물질

6

반응물 4

HCID 82115Trimethylsilyl cyanideHCID 2733225Ytterbium triflateHCID 181881764-(5-Methyl-1,2,4-oxadiazol-3-yl)anilineHCID 1363370832-{3-[(4-carbamimidoylphenylamino)-(2-fluoro-4,5-dimethoxyphenyl)methyl]5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}benzoic Acid Trifluoroacetate

생성물 1

HCID 59516906(3-Methoxy-5-methoxymethylphenyl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of the residue in 10 ml of dichloromethane there was added 550 mg of 4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamine, 1g of MS3A, 195 mg of Yb(OTf)3 and 0.79 ml of trimethylsilyl cyanide, and the mixture was stirred at room temperature for 20 hours under a nitrogen atmosphere. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give the title compound (1.25 g) as a light yellow oil.

후처리

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

출처 및 근거

ORD 기록
ord-040e670c1e9f4341b342a22daa81d55a
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07928228B2

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