Oxalyl chloride → 5-[4-(2,5-Dimethylpyrrolidin-1-yl)-3-nitrophenyl]-3-(2-methoxyphenyl)-1,2,4-oxadiazole

HRID 336281Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.[CH3:7][CH:8]1[CH2:12][CH2:11][CH:10]([CH3:13])[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].O[N:27]=[C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[O:36][CH3:37])[NH2:29].CCN(C(C)C)C(C)C>>[CH3:13][CH:10]1[CH2:11][CH2:12][CH:8]([CH3:7])[N:9]1[C:14]1[CH:22]=[CH:21][C:17]([C:18]2[O:20][N:29]=[C:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[O:36][CH3:37])[N:27]=2)=[CH:16][C:15]=1[N+:23]([O-:25])=[O:24]

Participants

Reactant 4

HCID 65578Oxalyl chloride

HCID 81531Diisopropylethylamine

HCID 4652214N-Hydroxy-2-methoxy-benzamidine

HCID 596065544-(2,5-Dimethylpyrrolidin-1-yl)-3-nitrobenzoic acid

Product 1

HCID 252564825-[4-(2,5-Dimethylpyrrolidin-1-yl)-3-nitrophenyl]-3-(2-methoxyphenyl)-1,2,4-oxadiazole

Procedure

Oxalyl chloride (152 mg; 1.2 mmol; 3 eq.), Intermediate 25 (106 mg; 0.4 mmol; 1 eq.), Intermediate 1 (66 mg; 0.4 mmol, 1 eq.) and DIEA (155 mg; 1.2 mmol; 3 eq.) were reacted according to general procedure 2. Purification by precipitation from Et2O/n-pentane afforded the title compound as a yellow solid.

Workup

customPurification
customby precipitation from Et2O/n-pentane

Sources & evidence

ORD record: ord-992a881eae5843aba1b743f965ef3696
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889668B2

Reaction notes

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