Trifluoroacetic acid → HCID 66590273, compound

HRID 1894809Notes

Reaction equation

HRID 1894809 reaction equation
C(OC([CH2:8][NH:9][C:10]1[N:15]=[C:14]([C:16]2[CH:21]=[CH:20][C:19]([CH:22]=[CH:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:18][CH:17]=2)[CH:13]=[CH:12][CH:11]=1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+].[CH2:41]([N:48]=[C:49]=[O:50])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47].CN(C1C=CC=CN=1)C>ClCCl.C(N(CC)CC)C.O>[CH2:41]([NH:48][C:49](=[O:50])[N:9]([C:10]1[N:15]=[C:14]([C:16]2[CH:17]=[CH:18][C:19]([CH:22]=[CH:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:20][CH:21]=2)[CH:13]=[CH:12][CH:11]=1)[CH3:8])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47]

Participants

9

Reactant 5

HCID 6422Trifluoroacetic acidHCID 218852-DimethylaminopyridineHCID 138341n-Heptyl isocyanateHCID 516892Sodium BicarbonateHCID 66591177HCID 66591177, compound

Product 1

HCID 66590273HCID 66590273, compoundYield 51.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

300 mg (0.78 mmol) of ethyl 3-{4-[6-(tert-butoxycarbonylmethylamino)pyrid-2-yl]phenyl}acrylate are dissolved in 5 mL of dichloromethane. 2 mL of trifluoroacetic acid are added. The reaction mixture is stirred for 3 hours at room temperature. The reaction is stopped by adding 30 mL of saturated sodium hydrogen carbonate solution and is then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the oil obtained is then dissolved in 5 ml of dichloromethane in the presence of 1 ml of triethylamine. 630 μL (3.9 mmol, 5 eq) of heptyl isocyanate are added along with 100 mg of dimethylaminopyridine. The reaction mixture is stirred for 16 hours at reflux. The reaction is stopped by adding 30 mL of water and is then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then chromatographed on silica gel (80/20 to 70/30 heptane/ethyl acetate). 170 mg of ethyl 3-{4-[6-(3-heptyl-1-methylureido)pyrid-2-yl]phenyl}acrylate are obtained. Yield=51%.

Workup

  1. extractionis then extracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. customThe solvents are evaporated off
  4. customthe oil obtained
  5. stirringThe reaction mixture is stirred for 16 hours
  6. temperatureat reflux
  7. extractionis then extracted with ethyl acetate
  8. dry with materialdried over sodium sulfate
  9. customThe solvents are evaporated off
  10. customthe residue is then chromatographed on silica gel (80/20 to 70/30 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-7c4cf1b9ebf24a75bbae3c62eac69a1a
Source dataset
uspto-grants-2013_08
Patent number
US08513297B2

Reaction notes

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