Hydrochloric Acid → HCID 58558187, compound

HRID 1969788Notes

Reaction equation

HRID 1969788 reaction equation
[CH:1]1([C:7]2[N:11]3[C:12]4[CH:18]=[CH:17][N:16](S(C5C=CC(C)=CC=5)(=O)=O)[C:13]=4[N:14]=[CH:15][C:10]3=[C:9]([CH2:29][CH2:30][C:31]([O:33]CC)=[O:32])[N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].Cl>O1CCOCC1>[CH:1]1([C:7]2[N:11]3[C:12]4[CH:18]=[CH:17][NH:16][C:13]=4[N:14]=[CH:15][C:10]3=[C:9]([CH2:29][CH2:30][C:31]([OH:33])=[O:32])[N:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67998619HCID 67998619, compound

Product 1

HCID 58558187HCID 58558187, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
65 °C

Procedure

To solution of ethyl 3-(1-cyclohexyl-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-3-yl)propanoate (0.031 g, 0.063 mmol, prepared using W from Example #12 Step A) in 1,4-dioxane (3 mL) was added NaOH (2 N aqueous, 1.57 mL, 3.13 mmol). The reaction mixture was heated to about 65° C. After about 2 h, the reaction mixture was cooled to ambient temperature and the pH of the mixture was adjusted to about 1 with 1 N aqueous HCl. The reaction mixture was concd in vacuo and purified by chromatography on silica gel (12 g) eluting with 2-10% MeOH in DCM to provide 3-(1-cyclohexyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-3-yl)propanoic acid (0.005 g, 26%) as a tan solid: LC/MS (Table 1, Method a) Rt=1.68 min; MS m/z: 313 (M+H)+.

Workup

  1. temperaturethe reaction mixture was cooled to ambient temperature
  2. custompurified by chromatography on silica gel (12 g)
  3. washeluting with 2-10% MeOH in DCM

Sources & evidence

ORD record
ord-405080bc16cf4ab9a1e1774d0bf47608
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

Loading…