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

HRID 1950882Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.[C:7]([C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[CH3:24])[C:12]([OH:14])=O)#[N:8].[F:25][C:26]1[CH:27]=[CH:28][C:29]([O:36][CH3:37])=[C:30]([C:32](=[N:34]O)[NH2:33])[CH:31]=1.CCN(C(C)C)C(C)C>>[F:25][C:26]1[CH:27]=[CH:28][C:29]([O:36][CH3:37])=[C:30]([C:32]2[N:33]=[C:12]([C:11]3[CH:15]=[CH:16][C:17]([N:18]4[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]4[CH3:24])=[C:9]([CH:10]=3)[C:7]#[N:8])[O:14][N:34]=2)[CH:31]=1

Participants

Reactant 4

HCID 65578Oxalyl chloride

HCID 81531Diisopropylethylamine

HCID 594957013-Cyano-4-(2-methylpiperidin-1-yl)benzoic acid

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

Product 1

HCID 596065295-[3-(5-Fluoro-2-methoxyphenyl)-1,2,4-oxadiazol-5-yl]-2-(2-methylpiperidin-1-yl)benzonitrile

Procedure

Oxalyl chloride (190 mg; 1.5 mmol; 3 eq.), Intermediate 36 (122 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, 70/30) afforded the title compound as a white solid.

Workup

customPurification by column chromatography (c-hexane/ethyl acetate, 70/30)

Sources & evidence

ORD record: ord-c6776fc34ee049dd8de4cc73802f743b
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08404676B2

Reaction notes

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