Chloroacetic anhydride → N-(5-(5-(chloromethyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 570307

Reaction equation

[OH:1][N:2]=[C:3]([C:5]1[CH:6]=[CH:7][C:8]([CH3:23])=[C:9]([NH:11][C:12]([C:14]2[N:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]3=[N:16][CH:15]=2)=[O:13])[CH:10]=1)[NH2:4].[Cl:24][CH2:25][C:26](OC(=O)CCl)=O>CN1C(=O)CCC1.O>[Cl:24][CH2:25][C:26]1[O:1][N:2]=[C:3]([C:5]2[CH:6]=[CH:7][C:8]([CH3:23])=[C:9]([NH:11][C:12]([C:14]3[N:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:17]4=[N:16][CH:15]=3)=[O:13])[CH:10]=2)[N:4]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of N-(5-(N′-hydroxycarbamimidoyl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (9) (500 mg, 1.62 mmol) and 2-chloroacetic anhydride (553 mg, 3.23 mmol) in anhydrous NMP (10 mL) was heated in the microwave at 110° C. for 12 minutes. The crude was diluted with water and extracted with ethyl acetate. The organic was washed with a water/brine mixture and dried over anhydrous sodium sulfate. The solvent was concentrated and the crude product was purified by silica chromatography to yield N-(5-(5-(chloromethyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (38). MS m/z 378.9 (M+1)+.

Workup

extractionextracted with ethyl acetate
washThe organic was washed with a water/brine mixture
dry with materialdried over anhydrous sodium sulfate
concentrationThe solvent was concentrated
customthe crude product was purified by silica chromatography

Sources & evidence

ORD record: ord-28895a24815b4778b06b3fe25ee23e98
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023839B2

Linked notes

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