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

HRID 405837
Notes
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Reaction equation

HRID 405837 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>CN1CCCC1=O.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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 10946Chloroacetic anhydrideHCID 86677441N-(5-(N'-hydroxycarbamimidoyl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide

Product 1

HCID 86677445N-(5-(5-(chloromethyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidone
Solvent

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 1-methyl-2-pyrrolidinone (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 water/brine mixture and dried over anhydrous sodium sulfate. The crude product was purified by silica chromatography. MS m/z 368.08 (M+1)+.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic was washed with water/brine mixture
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe crude product was purified by silica chromatography

Sources & evidence

ORD record
ord-3fa0a85c1d5141e5a6e1c73da4977fbc
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08754071B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes