Oxalyl chloride → 1-{4-[3-(5-Fluoro-2-methoxyphenyl)-1,2,4-oxadiazol-5-YL]-2-nitrophenyl}-2-methylpiperidine

HRID 336271Notes

Reaction equation

HRID 336271 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[N+:23]([O-:25])=[O:24].[F:26][C:27]1[CH:28]=[CH:29][C:30]([O:37][CH3:38])=[C:31]([C:33](=[N:35]O)[NH2:34])[CH:32]=1.CCN(C(C)C)C(C)C>>[F:26][C:27]1[CH:28]=[CH:29][C:30]([O:37][CH3:38])=[C:31]([C:33]2[N:34]=[C:18]([C:17]3[CH:21]=[CH:22][C:14]([N:9]4[CH2:10][CH2:11][CH2:12][CH2:13][CH:8]4[CH3:7])=[C:15]([N+:23]([O-:25])=[O:24])[CH:16]=3)[O:20][N:35]=2)[CH:32]=1

Participants

5

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 431767024-(2-Methylpiperidin-1-yl)-3-nitrobenzoic acidHCID 723368235-fluoro-N'-hydroxy-2-methoxybenzenecarboximidamide

Product 1

HCID 252563871-{4-[3-(5-Fluoro-2-methoxyphenyl)-1,2,4-oxadiazol-5-YL]-2-nitrophenyl}-2-methylpiperidine

Procedure

Oxalyl chloride (190 mg; 1.5 mmol; 3 eq.), Intermediate 8 (132 mg; 0.5 mmol; 1 eq.), Intermediate 23 (92 mg; 0.5 mmol, 1 eq.) and DIEA (194 mg; 1.5 mmol; 3 eq.) were reacted according to general procedure 2. Purification by column chromatography (c-hexane/ethyl acetate, 80/20) followed by crystallisation from ethyl acetate/n-pentane afforded the title compound as a yellow solid.

Workup

  1. customPurification by column chromatography (c-hexane/ethyl acetate, 80/20)
  2. customfollowed by crystallisation from ethyl acetate/n-pentane

Sources & evidence

ORD record
ord-7c71984599a14d8bb4b796c40571eb43
Source dataset
uspto-grants-2014_11
Patent number
US08889668B2

Reaction notes

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