Oxalyl chloride → (E)-N-[2-[(5-Ethyl-6-methyl-pyrimidin-4-yl)amino]butyl]-4,4,4-trifluoro-but-2-enamide

HRID 333097ノート

反応式

HRID 333097 の反応式
[F:1][C:2]([F:9])([F:8])/[CH:3]=[CH:4]/[C:5](O)=[O:6].C(Cl)(=O)C(Cl)=O.[CH2:16]([C:18]1[C:19]([NH:25][CH:26]([CH2:29][CH3:30])[CH2:27][NH2:28])=[N:20][CH:21]=[N:22][C:23]=1[CH3:24])[CH3:17].C(N(C(C)C)CC)(C)C>C(Cl)Cl.CN(C=O)C>[CH2:16]([C:18]1[C:19]([NH:25][CH:26]([CH2:29][CH3:30])[CH2:27][NH:28][C:5](=[O:6])/[CH:4]=[CH:3]/[C:2]([F:9])([F:8])[F:1])=[N:20][CH:21]=[N:22][C:23]=1[CH3:24])[CH3:17]

参加物

7

反応物 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 57096144,4,4-Trifluorocrotonic acidHCID 66835480N2-(5-Ethyl-6-methyl-pyrimidin-4-yl)butane-1,2-diamine

生成物 1

HCID 56947464(E)-N-[2-[(5-Ethyl-6-methyl-pyrimidin-4-yl)amino]butyl]-4,4,4-trifluoro-but-2-enamide

試薬・触媒・溶媒 2

HCID 6344Dichloromethane触媒HCID 6228Dimethylformamide溶媒

実験手順

(E)-4,4,4-Trifluorobut-2-enoic acid (15 mg, 0.11 mmol) was dissolved in DCM (1 ml containing one drop of dimethyl formamide), oxalyl chloride was added (9.5 μl, 0.11 mmol) and the solution was stirred at room temperature for 15 minutes. This solution was added to a solution of N2-(5-Ethyl-6-methyl-pyrimidin-4-yl)butane-1,2-diamine (24.5 mg, 0.1 mmol) and diisopropylethylamine (44 μl, 0.25 mmol) dissolved in DMF (1 ml) and the resulting mixture was stirred at room temperature overnight. The volatiles were removed under reduced pressure and the residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 12.7 mg (0.038 mmol, 38%).

後処理

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. customThe volatiles were removed under reduced pressure
  3. customthe residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile)
  4. customto yield 12.7 mg (0.038 mmol, 38%)

出典と根拠

ORDレコード
ord-9508645282fe42af965a655f90344ab6
出典データセット
uspto-grants-2014_11
特許番号
US08877934B2

反応ノート

読み込み中…