1,1'-Carbonyldiimidazole → HCID 58497373, compound

HRID 2175189Notes

Reaction equation

HRID 2175189 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH:5]([CH2:9][NH:10][C:11]1[C:16]([NH2:17])=[CH:15][CH:14]=[CH:13][N:12]=1)[CH2:6][CH2:7][CH3:8])[CH3:2].C1N=CN([C:24](N2C=NC=C2)=[O:25])C=1>C1COCC1>[CH2:1]([O:3][C:4](=[O:18])[CH:5]([CH2:9][N:10]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:16]2[NH:17][C:24]1=[O:25])[CH2:6][CH2:7][CH3:8])[CH3:2]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 58497453HCID 58497453, compound

Product 1

HCID 58497373HCID 58497373, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-[(3-amino-pyridin-2-ylamino)-methyl]-pentanoic acid ethyl ester (70 mg, 0.28 mmol) in THF (10 ml) was added CDI (135 mg, 0.84 mmol). The resulting solution was stirred at room temperature for 5 days after which time the reaction appeared to be complete. Silica gel was added and the mixture was concentrated. The remaining solid was purified via silica gel flash column chromatography (Companion, 12 g silica gel, 30-100% EtOAc/hexanes) to give 50 mg (65%) of the title compound as oil which solidified on standing.

Workup

  1. additionSilica gel was added
  2. concentrationthe mixture was concentrated
  3. customThe remaining solid was purified via silica gel flash column chromatography (Companion, 12 g silica gel, 30-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-835502a9299d472194642534c09a1888
Source dataset
uspto-grants-2015_06
Patent number
US09062056B2

Reaction notes

Loading…