Hydrochloric Acid → HCID 86672052, compound

HRID 1261763Notes

Reaction equation

FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[C:11]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH:10]=1.[CH:25]([C:27]1[CH:36]=[CH:35][C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:29][CH:28]=1)=O.C[O-].[Na+].Cl>CO.O>[CH3:34][O:33][C:31](=[O:32])[C:30]1[CH:35]=[CH:36][C:27](/[CH:25]=[CH:16]/[C:15]([C:12]2[CH:13]=[CH:14][C:9]([Cl:8])=[CH:10][C:11]=2[NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[O:17])=[CH:28][CH:29]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of the trifluoroacetic acid salt of 1-[4-chloro-2-(pyridin-2-ylamino)-phenyl]-ethanone (273 mg, 757 μmol) in methanol (3.78 mL) at 25° C. was treated with methyl 4-formylbenzoate (124 mg, 757 μmol) and sodium methoxide in methanol (4.37M, 520 μL, 2.27 mmol). The reaction was stirred at 25° C. for 3 d. At this time, the reaction was diluted with water (50 mL), neutralized with a 1N aqueous hydrochloric acid solution and extracted with methylene chloride (3×50 mL). The combined organics were dried over sodium sulfate, filtered and concentrated in vacuo to afford 4-{(E)-3-[4-chloro-2-(pyridin-2-ylamino)-phenyl]-3-oxo-propenyl}-benzoic acid methyl ester (287.3 mg, 96.6%) as an orange solid. The material was used without further purification.

Workup

extractionextracted with methylene chloride (3×50 mL)
dry with materialThe combined organics were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-0e54ae7799cc44c48a0c488c48132094
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08471027B2

Reaction notes

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