1-(1H-imidazole-1-carboximidoyl)-1H-imidazole → 2-Amino-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17443노트

반응식

HRID 17443 반응식
[NH2:1][C:2]1[C:7]([OH:8])=[C:6]([F:9])[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:4]([CH3:16])[C:3]=1[C:17]#[N:18].[N:19]1(C(N2C=CN=C2)=N)C=CN=[CH:20]1>O1CCCC1>[NH2:19][C:20]1[O:8][C:7]2[C:2](=[C:3]([C:17]#[N:18])[C:4]([CH3:16])=[C:5]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:6]=2[F:9])[N:1]=1

참가 물질

4

반응물 2

HCID 113556541-(1H-imidazole-1-carboximidoyl)-1H-imidazoleHCID 860974464-Amino-3-cyano-6-fluoro-5-hydroxy-2-methylbiphenyl

생성물 1

HCID 685859852-Amino-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile수율 87.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

4-Amino-6-fluoro-5-hydroxy-2-methylbiphenyl-3-carbonitrile (I-41) (1.66 g, 6.86 mmol) and di(imidazol-1-yl)methanimine (2.821 g) were suspended in tetrahydrofuran (33 ml), and stirred under reflux under nitrogen atmosphere for 120 hours. After cooling to room temperature, the solvent was evaporated away under reduced pressure. The residue was fractionated with 10% methanol-containing chloroform and water. The organic layer was separated, and dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, and the solvent was evaporated away under reduced pressure. The residue was recrystallized form methanol to obtain the entitled compound (1.60 g, 87%) as a pale brown solid.

후처리

  1. temperatureunder reflux under nitrogen atmosphere for 120 hours
  2. customthe solvent was evaporated away under reduced pressure
  3. additioncontaining chloroform and water
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe insoluble matter was separated by filtration
  7. customthe solvent was evaporated away under reduced pressure
  8. customThe residue was recrystallized form methanol

출처 및 근거

ORD 기록
ord-98ab37a38b804d2688562a7942c0e842
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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