Tetrahydrofuran → (S)-3-(5-Methyl-2-oxo-1,2-dihydro-imidazo[4,5-b]pyridin-3-yl)-hexanoic acid ethyl ester

HRID 2175164Notes

Reaction equation

HRID 2175164 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C@@H:6]([NH:10][C:11]1[C:16]([NH2:17])=[CH:15][CH:14]=[C:13]([CH3:18])[N:12]=1)[CH2:7][CH2:8][CH3:9])[CH3:2].C1C[O:23][CH2:22]C1>>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C@@H:6]([N:10]1[C:11]2=[N:12][C:13]([CH3:18])=[CH:14][CH:15]=[C:16]2[NH:17][C:22]1=[O:23])[CH2:7][CH2:8][CH3:9])[CH3:2]

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 58497432(S)-3-(3-Amino-6-methyl-pyridin-2-ylamino)-hexanoic acid ethyl ester

Product 1

HCID 58497440(S)-3-(5-Methyl-2-oxo-1,2-dihydro-imidazo[4,5-b]pyridin-3-yl)-hexanoic acid ethyl esterYield 64%

Procedure

To a solution of (S)-3-(3-amino-6-methyl-pyridin-2-ylamino)-hexanoic acid ethyl ester (350 mg, 1.32 mmol) in THF (10 mL) was added N,N′-carbonyldiimidazole (CDI) (321 mg, 2.0 mmol). The reaction mixture was stirred at room temperature for 5 hours. The reaction mixture was concentrated. The resulting residue was purified by silica gel preparative TLC using 95:5 CH2Cl2:MeOH as an eluent to afford 247 mg (64%) of the title compound as a light brown oily residue. LCMS, M++1, m/z: 292.59.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customThe resulting residue was purified by silica gel preparative TLC

Sources & evidence

ORD record
ord-d080fe7e95864ea7a0fa2ee9ba9e5995
Source dataset
uspto-grants-2015_06
Patent number
US09062056B2

Reaction notes

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