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

HRID 230364Notes

Reaction equation

HRID 230364 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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, mobile phase: 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).

Workup

  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, mobile phase: cyclohexane/ethyl acetate=3/2)

Sources & evidence

ORD record
ord-ad2c7d3c1c914a4ba49ebaf8004a528e
Source dataset
uspto-grants-2009_07
Patent number
US07566724B2

Reaction notes

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