Hydrochloric Acid → HCID 57940946, compound

HRID 1437469Notes

Reaction equation

HRID 1437469 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[N:10]([CH2:24][C:25]([O:27]C(C)(C)C)=[O:26])[C:11]3[C:12]([N:23]=2)=[N:13][CH:14]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:16]=3)[CH:6]=[CH:7][CH:8]=1.Cl.O>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[N:10]([CH2:24][C:25]([OH:27])=[O:26])[C:11]3[C:12]([N:23]=2)=[N:13][CH:14]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:16]=3)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 86597981HCID 86597981, compound

Product 1

HCID 57940946HCID 57940946, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To tert-butyl [2-(3-methoxyphenyl)-6-phenyl-1H-imidazo[4,5-b]pyridin-1-yl]acetate (209 mg) was added a solution of 4 N hydrogen chloride in ethyl acetate (8.0 ml), and the mixture was stirred at room temperature for 5 hours to hydrolyze. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water and dried over MgSO4, and the solvent was distilled off under reduced pressure. The resulting crystals were collected by filtration to obtain [2-(3-methoxyphenyl)-6-phenyl-1H-imidazo[4,5-b]pyridin-1-yl]acetic acid (129 mg, 43%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over MgSO4
  4. distillationthe solvent was distilled off under reduced pressure
  5. filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-1cb46109dec847e3947f8e7e0cc788a5
Source dataset
uspto-grants-2009_11
Patent number
US07622479B2

Reaction notes

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