Oxalyl chloride → 5-[3-(5-Fluoro-2-methoxyphenyl)-1,2,4-oxadiazol-5-YL]-2-(2-methylpiperidin-1-YL)pyridine

HRID 336314Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.C[C:8]1[C:9]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]2[CH3:23])=[N:10][CH:11]=[C:12]([CH:16]=1)[C:13]([OH:15])=O.[F:24][C:25]1[CH:26]=[CH:27][C:28]([O:35][CH3:36])=[C:29]([C:31](=[N:33]O)[NH2:32])[CH:30]=1.CCN(C(C)C)C(C)C>>[F:24][C:25]1[CH:26]=[CH:27][C:28]([O:35][CH3:36])=[C:29]([C:31]2[N:32]=[C:13]([C:12]3[CH:16]=[CH:8][C:9]([N:17]4[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]4[CH3:23])=[N:10][CH:11]=3)[O:15][N:33]=2)[CH:30]=1

Participants

Reactant 4

HCID 65578Oxalyl chloride

HCID 81531Diisopropylethylamine

HCID 584433645-Methyl-6-(2-methylpiperidin-1-yl)nicotinic acid

HCID 723368235-fluoro-N'-hydroxy-2-methoxybenzenecarboximidamide

Product 1

HCID 252554795-[3-(5-Fluoro-2-methoxyphenyl)-1,2,4-oxadiazol-5-YL]-2-(2-methylpiperidin-1-YL)pyridine

Procedure

Oxalyl chloride (138 μL; 1.63 mmol; 3 eq.), Intermediate 39 (120 mg; 0.54 mmol; 1 eq.), Intermediate 23 (100 mg; 0.54 mmol, 1 eq.) and DIEA (282 μL; 1.54 mmol; 3 eq.) were reacted according to general procedure 2. Purification by column chromatography c-hexane/ethyl acetate, 50/50) afforded the title compound as a yellow oil.

Workup

customPurification by column chromatography c-hexane/ethyl acetate, 50/50)

Sources & evidence

ORD record: ord-d1aed2404db64affa603aeed3c55cebc
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889668B2

Reaction notes

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