Pyridine → HCID 3226079, compound

HRID 1172737Notes

Reaction equation

Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]=[C:13]([CH:15]3[CH2:20][CH2:19][CH2:18][NH:17][CH2:16]3)[O:12][N:11]=2)=[CH:6][CH:5]=1.N1C=CC=CC=1.F[C:28]1[CH:36]=[CH:35][C:31]([C:32](Cl)=[O:33])=[CH:30][CH:29]=1>C1COCC1>[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:14]=[C:13]([CH:15]3[CH2:20][CH2:19][CH2:18][N:17]([C:32]([C:31]4[CH:35]=[CH:36][CH:28]=[CH:29][CH:30]=4)=[O:33])[CH2:16]3)[O:12][N:11]=2)=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 3-[3-(4-Methoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-piperidine hydrochloride (0.320 g, 1.08 mmol) in THF (2.3 ml, 0.5M) was added Pyridine (0.3 ml, 3.78 mmol). The reaction mixture was cooled to 0° C. and 4-Fluoro-benzoyl chloride (0.172 g-0.87 mmol) was slowly added. The reaction was to go up to R.T and stirred for 24 h. The solution was concentrated and DCM was added following by HCl 1N. The aqueous phase was separated and organic phase was extracted twice with HCl 1N and twice with water, dried over Na2SO4, filtered and concentrated. The crude product was purified by flash chromatography (DCM/MeOH: 99/1) to afford 0.26 mg (66%) of {3-[3-(4-Methoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-piperidin-1-yl}-phenyl-methanone as a white powder.

Workup

concentrationThe solution was concentrated
additionDCM was added
customThe aqueous phase was separated
extractionorganic phase was extracted twice with HCl 1N and twice with water
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe crude product was purified by flash chromatography (DCM/MeOH: 99/1)

Sources & evidence

ORD record: ord-51422432fc714c45953b6eb1ca4438d2
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07834035B2

Reaction notes

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