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

HRID 1935006ノート

反応式

HRID 1935006 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-03e014cf13c043c4b6ffcebe8421996a
出典データセット
uspto-grants-2002_05
特許番号
US06384051B1

反応ノート

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