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

HRID 333097노트

반응식

HRID 333097 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane촉매HCID 6228Dimethylformamide용매

실험 절차

(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%).

후처리

  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%)

출처 및 근거

ORD 기록
ord-9508645282fe42af965a655f90344ab6
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877934B2

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