1,1'-Carbonyldiimidazole → (R)-3-(5-Methyl-2-oxo-1,2-dihydro-imidazo[4,5-b]pyridin-3-yl)-3-phenyl-propionic acid ethyl ester

HRID 2175168Notes

Reaction equation

HRID 2175168 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C@@H:6]([NH:13][C:14]1[C:19]([NH2:20])=[CH:18][CH:17]=[C:16]([CH3:21])[N:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2].C1N=CN([C:28](N2C=NC=C2)=[O:29])C=1>C1COCC1.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C@@H:6]([N:13]1[C:14]2=[N:15][C:16]([CH3:21])=[CH:17][CH:18]=[C:19]2[NH:20][C:28]1=[O:29])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH3:2]

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 58497458(R)-3-(3-Amino-6-methyl-pyridin-2-ylamino)-3-phenyl-propionic acid ethyl ester

Product 1

HCID 58497418(R)-3-(5-Methyl-2-oxo-1,2-dihydro-imidazo[4,5-b]pyridin-3-yl)-3-phenyl-propionic acid ethyl esterYield 59.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-3-(3-amino-6-methyl-pyridin-2-ylamino)-3-phenyl-propionic acid ethyl ester (390 mg, 1.30 mmol) in THF (10 mL) was added CDI (317 mg, 1.95 mmol). The reaction mixture was stirred at room temperature for 2 hours and then heated to 60° C. for another 2 hours. The reaction mixture was diluted with ethyl acetate and washed with water. The organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel prep TLC using 95:5 CH2Cl2:MeOH as an eluent to afford 250 mg (59%) of the title compound as a light brown foamy residue. LCMS, M++1, m/z: 326.43

Workup

  1. temperatureheated to 60° C. for another 2 hours
  2. washwashed with water
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe resulting residue was purified by silica gel prep TLC

Sources & evidence

ORD record
ord-d8be883bf1184dc9b9097f5147bb8c98
Source dataset
uspto-grants-2015_06
Patent number
US09062056B2

Reaction notes

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