HCID 57465131, compound → HCID 57465090, compound

HRID 1170872Notes

Reaction equation

HRID 1170872 reaction equation
C([O:3][C:4]([C:6]1[N:10]2[CH2:11][CH2:12][CH2:13][CH2:14][C:9]2=[N:8][C:7]=1[N:15]([CH2:25][CH2:26][CH2:27][CH3:28])[C:16](=[O:24])[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=1)=[O:5])C>CO.O1CCOCC1.O>[CH2:25]([N:15]([C:16](=[O:24])[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=1)[C:7]1[N:8]=[C:9]2[CH2:14][CH2:13][CH2:12][CH2:11][N:10]2[C:6]=1[C:4]([OH:5])=[O:3])[CH2:26][CH2:27][CH3:28]

Participants

4

Reactant 1

HCID 57465131HCID 57465131, compound

Product 1

HCID 57465090HCID 57465090, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21966525Dioxane MethanolSolvent

Procedure

2-[butyl-(3-chloro-benzoyl)-amino]-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine-3-carboxylic acid ethyl ester (11.7 mmol) was dissolved in a solution of 190 mL MeOH/dioxan/4 M NaOH in water in a ratio of 15/4/1 and the solution was stirred over night at room temperature. The solvent was removed under vacuum, EtOAc (700 mL) was added thereto and the organic phase was washed with 0.5 M KHSO4 in water (700 mL). The aqueous phase was extracted with EtOAc (300 mL) and the combined organic phases were washed with saturated aqueous NaCl solution (700 mL) and dried over sodium sulphate, and the solvent was removed under vacuum. 4.13 g (94% over two stages) of the desired product 2-[butyl-(3-chloro-benzoyl)-amino]-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine-3-carboxylic acid were obtained.

Workup

  1. customThe solvent was removed under vacuum, EtOAc (700 mL)
  2. additionwas added
  3. washthe organic phase was washed with 0.5 M KHSO4 in water (700 mL)
  4. extractionThe aqueous phase was extracted with EtOAc (300 mL)
  5. washthe combined organic phases were washed with saturated aqueous NaCl solution (700 mL)
  6. dry with materialdried over sodium sulphate
  7. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-fd14403a5579451ca3708ea17f4d077c
Source dataset
uspto-grants-2010_11
Patent number
US07829568B2

Reaction notes

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