N-{3-[(2E)-3-(dimethylamino)prop-2-enoyl]phenyl}acetamide → N-(3-(3-cyano-2-(4-phenoxyphenyl)pyrazolo[1,5-a]pyrimidin-7-yl)phenyl)acetamide

HRID 64258

반응식

HRID 64258 반응식
C[N:2]([CH3:17])/[CH:3]=[CH:4]/[C:5]([C:7]1[CH:8]=[C:9]([NH:13][C:14](=[O:16])[CH3:15])[CH:10]=[CH:11][CH:12]=1)=O.[NH2:18][C:19]1[NH:23][N:22]=[C:21]([C:24]2[CH:29]=[CH:28][C:27]([O:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:26][CH:25]=2)[C:20]=1C#N>CC(O)=O>[C:19]([C:20]1[C:21]([C:24]2[CH:29]=[CH:28][C:27]([O:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:26][CH:25]=2)=[N:22][N:23]2[C:5]([C:7]3[CH:8]=[C:9]([NH:13][C:14](=[O:16])[CH3:15])[CH:10]=[CH:11][CH:12]=3)=[CH:4][CH:3]=[N:2][C:17]=12)#[N:18]

참가 물질

4

반응물 2

HCID 11183866N-{3-[(2E)-3-(dimethylamino)prop-2-enoyl]phenyl}acetamideHCID 178509389HCID 178509389, 화합물

생성물 1

HCID 117668104N-(3-(3-cyano-2-(4-phenoxyphenyl)pyrazolo[1,5-a]pyrimidin-7-yl)phenyl)acetamide수율 90%

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
118 °C

실험 절차

To a solution of (E)-N-(3-(3-(dimethylamino)acryloyl)phenyl)acetamide (46 mg, 0.2 mmol) in HOAc (5 mL) was added 5-amino-3-(4-phenoxyphenyl)-1H-pyrazole-4-carbonitrile (55 mg, 0.2 mmol). The mixture was stirred at 118° C. for 4 hr. Then the reaction mixture was concentrated to a residue and partitioned between ethyl acetate (100 mL) and brine (100 mL). Organic layer was separated, washed with brine (2×100 mL), dried over sodium sulfate and concentrated to afford 80 mg (90%) of N-(3-(3-cyano-2-(4-phenoxyphenyl)pyrazolo[1,5-a]pyrimidin-7-yl)phenyl)acetamide as a colorless oil. MS (ESI) m/e [M+1]+ 446.

후처리

  1. concentrationThen the reaction mixture was concentrated to a residue
  2. custompartitioned between ethyl acetate (100 mL) and brine (100 mL)
  3. customOrganic layer was separated
  4. washwashed with brine (2×100 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-1062eafbd8514691beed719cb2ae853b
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447106B2

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