Triethylamine → (E)-2-(2,6-difluorobenzamido)-5-[4-(methyl-pyrimidin-2-ylamino)phenyl]pent-4-enoic acid methyl ester

HRID 1360080노트

반응식

HRID 1360080 반응식
C(N(CC)CC)C.[F:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:10]=1[C:11](Cl)=[O:12].[CH3:19][O:20][C:21](=[O:41])[CH:22]([NH2:40])[CH2:23][CH:24]=[CH:25][C:26]1[CH:31]=[CH:30][C:29]([N:32]([CH3:39])[C:33]2[N:38]=[CH:37][CH:36]=[CH:35][N:34]=2)=[CH:28][CH:27]=1.C(=O)([O-])O.[Na+]>ClCCl>[CH3:19][O:20][C:21](=[O:41])[CH:22]([NH:40][C:11](=[O:12])[C:10]1[C:9]([F:8])=[CH:17][CH:16]=[CH:15][C:14]=1[F:18])[CH2:23]/[CH:24]=[CH:25]/[C:26]1[CH:27]=[CH:28][C:29]([N:32]([CH3:39])[C:33]2[N:38]=[CH:37][CH:36]=[CH:35][N:34]=2)=[CH:30][CH:31]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 874382,6-Difluorobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 669119952-Amino-5-[4-(methyl-pyrimidin-2-ylamino)phenyl]pent-4-enoic acid methyl ester

생성물 1

HCID 57762602(E)-2-(2,6-difluorobenzamido)-5-[4-(methyl-pyrimidin-2-ylamino)phenyl]pent-4-enoic acid methyl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Under an argon atmosphere, triethylamine (0.028 ml) and 2,6-difluorobenzoyl chloride (0.015 ml) were added to a solution of 2-amino-5-[4-(methyl-pyrimidin-2-ylamino)phenyl]pent-4-enoic acid methyl ester (31.7 mg) in dichloromethane (2 ml), and the resulting mixture was stirred at room temperature for 2 hours. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction solution and the resulting mixture was extracted with ethyl acetate. Organic layer was washed twice with water and once with saturated brine, and dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the filtrate was concentrated. The residue was purified by thin layer chromatography (silica gel, developing solvent: cyclohexane/ethyl acetate=3/2) to obtain (E)-2-(2,6-difluorobenzamido)-5-[4-(methyl-pyrimidin-2-ylamino)phenyl]pent-4-enoic acid methyl ester (42 mg).

후처리

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washOrganic layer was washed twice with water and once with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customAfter removing anhydrous sodium sulfate
  5. filtrationby filtration
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by thin layer chromatography (silica gel, developing solvent: cyclohexane/ethyl acetate=3/2)

출처 및 근거

ORD 기록
ord-515b18a88ba5427493cb8c9a5de60586
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879837B2

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