Hydrochloric Acid → HCID 67398266, compound

HRID 70707Notes

Reaction equation

HRID 70707 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[C:8]([C:12]1[CH:17]=[CH:16][C:15](/[C:18](/[C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([O:29][CH3:30])[N:23]=2)=[CH:19]\[CH2:20][NH2:21])=[CH:14][CH:13]=1)([CH3:11])([CH3:10])[CH3:9].Cl>N1C=CC=CC=1>[C:8]([C:12]1[CH:17]=[CH:16][C:15](/[C:18](/[C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([O:29][CH3:30])[N:23]=2)=[CH:19]\[CH2:20][NH:21][C:1](=[O:3])[CH3:2])=[CH:14][CH:13]=1)([CH3:11])([CH3:9])[CH3:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 67400678(2E)-3-(4-tert-butylphenyl)-3-(5-chloro-6-methoxypyridin-2-yl)prop-2-en-1-amine

Product 1

HCID 67398266HCID 67398266, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride (21 μL) was added to a solution of (2E)-3-(4-tert-butylphenyl)-3-(5-chloro-6-methoxypyridin-2-yl)prop-2-en-1-amine in pyridine (1 mL), and the mixture was stirred at room temperature for 1.5 hours. 1 M hydrochloric acid was added to the reaction solution, followed by extraction with chloroform. The organic layer was dried over magnesium sulfate and filtered, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1→1:1) to give N-[(2E)-3-(4-tert-butylphenyl)-3-(5-chloro-6-methoxypyridin-2-yl)prop-2-en-1-yl]acetamide as a pale yellow amorphous (50 mg, 67% (two steps)).

Workup

  1. extractionfollowed by extraction with chloroform
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customafter which the solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1→1:1)

Sources & evidence

ORD record
ord-e94b963794564c15b4f412c4a15d65fd
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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