Water → 2-[4-(2-Ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)phenyl]ethyl propionate

HRID 724017Notes

Reaction equation

HRID 724017 reaction equation
[NH2:1][C:2]1[C:3]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][OH:19])=[CH:13][CH:12]=2)=[N:4][C:5]([CH3:9])=[CH:6][C:7]=1[CH3:8].[C:20](Cl)(=[O:23])[CH2:21][CH3:22].O.[C:26]1(C)[CH:31]=CC=C[CH:27]=1>>[C:20]([O:19][CH2:18][CH2:17][C:14]1[CH:15]=[CH:16][C:11]([N:10]2[C:3]3=[N:4][C:5]([CH3:9])=[CH:6][C:7]([CH3:8])=[C:2]3[N:1]=[C:27]2[CH2:26][CH3:31])=[CH:12][CH:13]=1)(=[O:23])[CH2:21][CH3:22]

Participants

5

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 62324Propionyl chlorideHCID 218759922-{4-[(3-Amino-4,6-dimethyl-2-pyridinyl)amino]phenyl}ethanol

Product 1

HCID 218759342-[4-(2-Ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)phenyl]ethyl propionate

Procedure

To a stirred suspension of 2-{4-[(3-amino-4,6-dimethyl-2-pyridinyl)amino]phenyl}ethanol (step 4, 1.3 g, 5.1 mmol) in toluene (30 mL) was added dropwise propionyl chloride (990 mg, 10.7 mmol) at 0° C., and the reaction mixture was heated at reflux temperature for 2 h. After cooling, the mixture was poured into water (50 mL) and extracted with ethyl acetate (100 mL). The organic layer was washed with 2N aqueous NaOH (50 mL) and brine (50 mL), then dried (MgSO4). Removal of solvent gave 1.8 g (quant.) of the title compound as brown solids: 1H-NMR (CDCl3) δ 7.41 (2H, d, J=8.4 Hz), 7.33 (2H, d, J=8.4 Hz), 6.90 (1H, s), 4.37 (2H, t, J=6.9 Hz), 3.04 (2H, t, J=6.9 Hz), 2.82 (2H, q, J=7.6 Hz), 2.65 (3H, s), 2.52 (3H, s), 2.35 (2H, q, J=7.6 Hz), 1.27 (3H, t, J=7.6 Hz), 1.14 (3H, t, J=7.6 Hz).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux temperature for 2 h
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate (100 mL)
  5. washThe organic layer was washed with 2N aqueous NaOH (50 mL) and brine (50 mL)
  6. dry with materialdried (MgSO4)
  7. customRemoval of solvent

Sources & evidence

ORD record
ord-dd4ec59a10a84ab9a9e934c7e569d1ed
Source dataset
uspto-grants-2006_11
Patent number
US07141580B2

Reaction notes

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