Benzenepropanoic acid → HCID 135899280, compound

HRID 2100464Notes

Reaction equation

HRID 2100464 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.[NH2:40][CH2:41][C:42]1[NH:43][C:44](=[O:52])[C:45]2[CH:51]=[CH:50][CH:49]=[N:48][C:46]=2[N:47]=1>CN(C=O)C>[O:52]=[C:44]1[NH:43][C:42]([CH2:41][NH:40][C:9](=[O:11])[CH2:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:47][C:46]2[N:48]=[CH:49][CH:50]=[CH:51][C:45]1=2

Participants

7

Reactant 5

HCID 107Benzenepropanoic acidHCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 136312202HCID 136312202, compound

Product 1

HCID 135899280HCID 135899280, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To 3-phenylpropionic acid [501-52-0] (66.6 mg, 0.444 mmol) in DMF (4 ml) was added EDCI [25952-53-8] (102 mg, 0.532 mmol), HOBt [2592-95-2] (8 mg, 0.059 mmol) and NMM [109-02-4] (0.15 ml, 1.18 mmol) at 0° C. The reaction mixture was stirred at ambient temperature for 2 h, and then was added to a solution of the salt of 2-aminomethyl-3H-pyrido[2,3-d]pyrimidin-4-one (CH3CO2H, HBr) (100 mg) in DMF (2 ml). Stirring was continued for 18 h, the solvents were evaporated and the residue as redissolved in EtOAc/THF and a saturated solution of ammonium chloride. The inorganic layer was extracted with EtOAc. The combined organic phases were washed with brine, dried over Na2SO4, filtrated and evaporated. Column chromatography with CH2Cl2/MeOH 9:1, followed by trituration with TBME gave N-(4-oxo-3,4-dihydro-pyrido[2,3-d]pyrimidin-2-ylmethyl)-3-phenyl-propionamide (43.1 mg, 47%) as a off-white solid, MS (m/e): 309 [M+H+].

Workup

  1. stirringStirring
  2. waitwas continued for 18 h
  3. customthe solvents were evaporated
  4. dissolutionthe residue as redissolved in EtOAc/THF
  5. extractionThe inorganic layer was extracted with EtOAc
  6. washThe combined organic phases were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltrated
  9. customevaporated

Sources & evidence

ORD record
ord-6ef279a8dfb94dd1a9ac1da0c59962e6
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

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