Oxalyl chloride → 1-[4-[3-(2-Methoxyphenyl)-1,2,4-oxadiazol-5-YL]-2-(trifluoromethyl)phenyl]-2-methylpiperidine

HRID 336274Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.[CH3:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][N:9]1[C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=O)=[CH:16][C:15]=1[C:23]([F:26])([F:25])[F:24].O[N:28]=[C:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[O:37][CH3:38])[NH2:30].CCN(C(C)C)C(C)C>>[CH3:38][O:37][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=1[C:29]1[N:28]=[C:18]([C:17]2[CH:21]=[CH:22][C:14]([N:9]3[CH2:10][CH2:11][CH2:12][CH2:13][CH:8]3[CH3:7])=[C:15]([C:23]([F:26])([F:25])[F:24])[CH:16]=2)[O:20][N:30]=1

Participants

Reactant 4

HCID 65578Oxalyl chloride

HCID 81531Diisopropylethylamine

HCID 4652214N-Hydroxy-2-methoxy-benzamidine

HCID 594956554-(2-Methylpiperidin-1-YL)-3-(trifluoromethyl)benzoic acid

Product 1

HCID 252551761-[4-[3-(2-Methoxyphenyl)-1,2,4-oxadiazol-5-YL]-2-(trifluoromethyl)phenyl]-2-methylpiperidine

Procedure

Oxalyl chloride (106 μL; 1.25 mmol; 3 eq.), Intermediate 24 (120 mg; 0.42 mmol; 1 eq.), Intermediate 1 (69 mg; 0.42 mmol, 1 eq.) and DIEA (93 μL; 1.25 mmol; 3 eq.) were reacted according to general procedure 2. Purification by column chromatography c-hexane/ethyl acetate, 80/20) followed by precipitation from n-pentane afforded the title compound as a white solid.

Workup

customPurification by column chromatography c-hexane/ethyl acetate, 80/20)
customfollowed by precipitation from n-pentane

Sources & evidence

ORD record: ord-7a66e7dd73d74f2284bee7b954e39f0d
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889668B2

Reaction notes

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