Ethylene Glycol → 2-Hydroxyethyl 3-(6-aminopyridin-3-yl)-2-(1-cyclohexyl-1H-imidazol-4-yl)propionate

HRID 2370915Notes

Reaction equation

HRID 2370915 reaction equation
Cl.Cl.[NH2:3][C:4]1[N:9]=[CH:8][C:7]([CH2:10][CH:11]([C:15]2[N:16]=[CH:17][N:18]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[CH:19]=2)[C:12]([OH:14])=[O:13])=[CH:6][CH:5]=1.[CH2:26](O)[CH2:27][OH:28]>>[NH2:3][C:4]1[N:9]=[CH:8][C:7]([CH2:10][CH:11]([C:15]2[N:16]=[CH:17][N:18]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[CH:19]=2)[C:12]([O:14][CH2:26][CH2:27][OH:28])=[O:13])=[CH:6][CH:5]=1

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 694540453-(6-Aminopyridin-3-yl)-2-(1-cyclohexyl-1H-imidazol-4-yl)propionic acid hydrochloride

Product 1

HCID 116533642-Hydroxyethyl 3-(6-aminopyridin-3-yl)-2-(1-cyclohexyl-1H-imidazol-4-yl)propionate

Procedure

0.4 ml of an HCl-saturated ether solution was added to a solution of 50.0 mg (0.16 mmol) of the compound from example 1i in 1 ml of ethylene glycol and stirred at RT for 1 h. The solution was then concentrated to dryness, and the residue was taken up in sat. NaHCO3 solution and extracted with EA several times. The combined EA extracts were dried, filtered and concentrated. The resulting residue was dried under high vacuum, resulting in 33 mg of the title compound in the form of a pale yellow oil.

Workup

  1. concentrationThe solution was then concentrated to dryness
  2. extractionextracted with EA several times
  3. dry with materialThe combined EA extracts were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was dried under high vacuum

Sources & evidence

ORD record
ord-e2bcf4895b3c47a09f26fe6c8a7e2c1d
Source dataset
uspto-grants-2014_04
Patent number
US08710232B2

Reaction notes

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