Oxalyl chloride → 5-[3-(5-Fluoro-2-methoxyphenyl)-1,2,4-oxadiazol-5-YL]-2-[2-(methoxymethyl)pyrrolidin-1-YL]-3-methylpyridine

HRID 1950886Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][CH2:9][CH:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15]1[C:23]([CH3:24])=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][N:16]=1.[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:19]([C:18]3[CH:22]=[C:23]([CH3:24])[C:15]([N:11]4[CH2:12][CH2:13][CH2:14][CH:10]4[CH2:9][O:8][CH3:7])=[N:16][CH:17]=3)[O:21][N:34]=2)[CH:31]=1

Participants

Reactant 4

HCID 65578Oxalyl chloride

HCID 81531Diisopropylethylamine

HCID 594958236-[2-(Methoxymethyl)pyrrolidin-1-yl]-5-methylnicotinic acid

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

Product 1

HCID 252554805-[3-(5-Fluoro-2-methoxyphenyl)-1,2,4-oxadiazol-5-YL]-2-[2-(methoxymethyl)pyrrolidin-1-YL]-3-methylpyridine

Procedure

Oxalyl chloride (122 μL; 1.44 mmol; 3 eq.), Intermediate 40 (120 mg; 0.48 mmol; 1 eq.), Intermediate 23 (88 mg; 0.48 mmol, 1 eq.) and DIEA (245 μL; 1.44 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-6554c62cab2f40d398bbad6fd13d26f2
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08404676B2

Reaction notes

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