Triethylamine → N-{3-Cyano-4-[(3,4-difluorophenyl)amino]-6-quinolinyl}-2-propenamide

HRID 1935006노트

반응식

HRID 1935006 반응식
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]#[N:13])=[C:5]2[NH:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[C:17]([F:22])[CH:16]=1.C(N(CC)CC)C.[C:30](Cl)(=[O:33])[CH:31]=[CH2:32].C(=O)(O)[O-].[Na+]>CN(C=O)C.C1COCC1>[C:12]([C:6]1[CH:7]=[N:8][C:9]2[C:4]([C:5]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[C:17]([F:22])[CH:16]=1)=[CH:3][C:2]([NH:1][C:30](=[O:33])[CH:31]=[CH2:32])=[CH:11][CH:10]=2)#[N:13]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 516892Sodium BicarbonateHCID 224665706-Amino-4-[(3,4-difluorophenyl)amino]-3-quinolinecarbonitrile

생성물 1

HCID 22466577N-{3-Cyano-4-[(3,4-difluorophenyl)amino]-6-quinolinyl}-2-propenamide수율 28.1%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

Dissolved 1.00 g (3.37 mmol) 6-amino-4-[(3,4-difluorophenyl)amino]-3-quinolinecarbonitrile in 2 ml DMF, added 12 ml THF, and chilled to 0° C. under N2. Added 517 μl (3.71 mmol) triethylamine and 310 μl (3.72 mmol) acryloyl chloride. Removed ice bath a 15 minutes. At 3.5 hours stripped solvent and slurried residue with dilute sodium bicarbonate. Collected solids, washed with water, and air dried. Boiled in ethyl acetate, collected solids and dried in vacuo, giving 332 mg of yellow solid: mass spectrum (electrospray m/e): M+H=351.1.

후처리

  1. customa 15 minutes
  2. customCollected solids
  3. washwashed with water, and air
  4. customdried
  5. customcollected solids
  6. customdried in vacuo

출처 및 근거

ORD 기록
ord-03e014cf13c043c4b6ffcebe8421996a
출처 데이터셋
uspto-grants-2002_05
특허 번호
US06384051B1

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