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

HRID 2175195Notes

Reaction equation

HRID 2175195 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][C@@H:6]([NH:13][C:14]1[C:19]([NH2:20])=[CH:18][CH:17]=[C:16]([C:21]#[N:22])[N:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2].C1N=CN([C:29](N2C=NC=C2)=[O:30])C=1.C1CCN2C(=NCCC2)CC1>C1COCC1>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][C@@H:6]([N:13]1[C:14]2=[N:15][C:16]([C:21]#[N:22])=[CH:17][CH:18]=[C:19]2[NH:20][C:29]1=[O:30])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH3:2]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 58497449(R)-3-(3-Amino-6-cyano-pyridin-2-ylamino)-3-phenyl-propionic acid ethyl ester

Product 1

HCID 58497426(R)-3-(5-Cyano-2-oxo-1,2-dihydro-imidazo[4,5-b]pyridin-3-yl)-3-phenyl-propionic acid ethyl esterYield 19%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (R)-3-(3-amino-6-cyano-pyridin-2-ylamino)-3-phenyl-propionic acid ethyl ester (600 mg, 1.93 mmol) in THF (20 ml) was added CDI (630 mg, 3.87 mmol) and DBU (0.12 ml, 0.77 mmol). The resulting solution was stirred at room temperature for 18 hours after which time the reaction appeared complete. Added silica gel and concentrated. The remaining solid was purified via silica gel flash column chromatography (Companion, 12 g silica gel, 30-60% EtOAc/hexanes) to give 120 mg (19%) of the title compound.

Workup

  1. concentrationAdded silica gel and concentrated
  2. customThe remaining solid was purified via silica gel flash column chromatography (Companion, 12 g silica gel, 30-60% EtOAc/hexanes)

Sources & evidence

ORD record
ord-69c5ff9435a94d8b9460d3c86ddeb614
Source dataset
uspto-grants-2015_06
Patent number
US09062056B2

Reaction notes

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