Benzenepropanoyl chloride → HCID 135899207, compound

HRID 2100512Notes

Reaction equation

HRID 2100512 reaction equation
[NH2:1][CH2:2][C:3]1[NH:4][C:5](=[O:14])[C:6]2[CH:12]=[C:11]([F:13])[CH:10]=[N:9][C:7]=2[N:8]=1.CCN(C(C)C)C(C)C.[C:24]1([CH2:30][CH2:31][C:32](Cl)=[O:33])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1COCC1.CCOC(C)=O>[F:13][C:11]1[CH:10]=[N:9][C:7]2[N:8]=[C:3]([CH2:2][NH:1][C:32](=[O:33])[CH2:31][CH2:30][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[NH:4][C:5](=[O:14])[C:6]=2[CH:12]=1

Participants

6

Reactant 3

HCID 64801Benzenepropanoyl chlorideHCID 81531DiisopropylethylamineHCID 1363458282-(Aminomethyl)-6-fluoropyrido[2,3-d]pyrimidin-4(3H)-one

Product 1

HCID 135899207HCID 135899207, compoundYield 2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-aminomethyl-6-fluoro-3H-pyrido[2,3-d]pyrimidin-4-one (130 mg, 0.67 mmol) in THF (5 ml) was treated with DIPEA (173 mg, 1.34 mmol) and 3-phenyl-propionyl chloride (136 mg, 0.80 mmol) at 0° C. for 18 hours. The reaction mixture was diluted with EtOAc, washed with water and brine. The organic layers were dried over MgSO4, filtrated, evaporated and chromatographed (silica gel, EtOAc/heptane, 1/1) to yield N-(6-fluoro-4-oxo-3,4-dihydro-pyrido[2,3-d]pyrimidin-2-ylmethyl)-3-phenyl-propionamide (6 mg, 13 μmol; 2%) as yellow solid. MS (m/e): 327.3 [M+H+].

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layers were dried over MgSO4
  3. filtrationfiltrated
  4. customevaporated
  5. customchromatographed (silica gel, EtOAc/heptane, 1/1)

Sources & evidence

ORD record
ord-f43bc49e602b4a64aa486b1deb31a991
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

Loading…