Triethylamine → 3-Acetylamino-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]-5-(trifluoromethyl)-benzamide

HRID 1441756ノート

反応式

HRID 1441756 の反応式
[CH2:1](OP(C#N)(=O)OCC)C.C[C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]2[N:24]=[C:23]([C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)[CH:22]=[CH:21][N:20]=2)=[CH:14][C:13]=1[NH2:31].[C:32]([NH:35][C:36]1[CH:37]=[C:38]([CH:42]=[C:43]([C:45]([F:48])([F:47])[F:46])[CH:44]=1)[C:39](O)=[O:40])(=[O:34])[CH3:33].C(N(CC)CC)C.C(=O)([O-])O.[Na+]>CN(C)C=O>[C:32]([NH:35][C:36]1[CH:37]=[C:38]([CH:42]=[C:43]([C:45]([F:48])([F:47])[F:46])[CH:44]=1)[C:39]([NH:31][C:13]1[CH:12]=[CH:17][C:16]([CH3:1])=[C:15]([NH:18][C:19]2[N:24]=[C:23]([C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)[CH:22]=[CH:21][N:20]=2)[CH:14]=1)=[O:40])(=[O:34])[CH3:33]

参加物

7

反応物 5

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 2868483-Acetamido-5-(trifluoromethyl)benzoic acidHCID 516892Sodium BicarbonateHCID 24820369N-(3-amino-4-methylphenyl)-4-(pyridin-3-yl)-2-pyrimidine-amine

生成物 1

HCID 117559093-Acetylamino-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]-5-(trifluoromethyl)-benzamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
20 °C

実験手順

Diethylcyanophosphonate (Aldrich, Buchs, Switzerland; 0.66 mL, 4.0 mmol) is added to a stirred mixture of 4-methyl-N-[4-(3-pyridinyl)-2-pyrimidinyl]-1,3-benzenediamine (554 mg, 2.0 mmol), 3-acetylamino-5-(trifluoromethyl)-benzoic acid (495 mg, 2.0 mmol) and triethylamine (1.12 mL, 8.0 mmol) in 10 mL N,N-dimethylformamide at 20° C. under an argon atmosphere. After stirring for 18 hours at 20° C., the mixture is treated with saturated aqueous solution of sodium hydrogen carbonate and extracted twice with ethyl acetate. The combined extracts are dried (MgSO4), filtered and the solvent is evaporated off under reduced pressure to afford a crude product. The crude product is purified by column chromatography on silica gel, eluent dichloromethane/methanol/aqueous ammonia. The pure fractions are combined, the solvent is evaporated off under reduced pressure and the residue is crystallised from ethyl acetate-hexane to give the title compound as a cream crystalline solid.

後処理

  1. extractionextracted twice with ethyl acetate
  2. dry with materialThe combined extracts are dried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent is evaporated off under reduced pressure
  5. customto afford a crude product
  6. customThe crude product is purified by column chromatography on silica gel, eluent dichloromethane/methanol/aqueous ammonia
  7. customthe solvent is evaporated off under reduced pressure
  8. customthe residue is crystallised from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-30cc0a4bcb1e435e8444fde8960e1ead
出典データセット
uspto-grants-2010_02
特許番号
US07655669B2

反応ノート

読み込み中…