Hydrochloric Acid → HCID 22344575, compound

HRID 1070128Notes

Reaction equation

HRID 1070128 reaction equation
[H-].[Na+].[OH:3]/[N:4]=[C:5](/[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)\[CH2:6][CH2:7][C:8]([O:10][CH3:11])=[O:9].[Cl:18][C:19]1[N:24]2[CH:25]=[C:26]([CH2:28][O:29][C:30]3[CH:35]=[CH:34][C:33]([CH2:36]Cl)=[CH:32][CH:31]=3)[N:27]=[C:23]2[CH:22]=[CH:21][CH:20]=1.Cl.C(=O)(O)[O-].[Na+]>CN(C)C=O.C(OCC)(=O)C.CCCCCC>[Cl:18][C:19]1[N:24]2[CH:25]=[C:26]([CH2:28][O:29][C:30]3[CH:31]=[CH:32][C:33]([CH2:36][O:3]/[N:4]=[C:5](/[C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)\[CH2:6][CH2:7][C:8]([O:10][CH3:11])=[O:9])=[CH:34][CH:35]=3)[N:27]=[C:23]2[CH:22]=[CH:21][CH:20]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 12137371methyl (4E)-4-hydroxyimino-4-phenylbutanoateHCID 223445955-Chloro-2-(4-chloromethylphenoxymethyl)imidazo[1,2-a]pyridine

Product 1

HCID 22344575HCID 22344575, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Sodium hydride (60%, in oil, 143 mg) was added to a solution of methyl E-4-(hydroxyimino)-4-phenylbutyrate (676 mg) and 5-chloro-2-(4-chloromethylphenoxymethyl)imidazo[1,2-α]pyridine (1.00 g) in N,N-dimethyformamide (10 ml) at room temperature and stirred for 1 hour. 1N hydrochloric acid (7 ml) was added, an aqueous saturated solution of sodium bicarbonate was added and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was subjected to silica gel chromatography to obtain methyl E-4-[4-(5-chloroimidazo[1,2-α]pyridin-2-ylmethoxy)benzyloxyimino]-4-phenylbutyrate (1.04 g, yield 67%) as a colorless oil from an ethyl acetate-hexane (2:1, v/v)-eluted fraction.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6b7c0d62ea0e4bf6ba4f6f445f8d471f
Source dataset
uspto-grants-2001_06
Patent number
US06251926B1

Reaction notes

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