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

HRID 336315
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HRID 336315 반응식
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
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참가 물질

5

반응물 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 594958236-[2-(Methoxymethyl)pyrrolidin-1-yl]-5-methylnicotinic acidHCID 723368235-fluoro-N'-hydroxy-2-methoxybenzenecarboximidamide

생성물 1

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

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-6e4205bd98a34a4392cf382b9da7111a
출처 데이터셋
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08889668B2

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