4-Methylmorpholine → HCID 21111685, compound

HRID 2113917Notes

Reaction equation

HRID 2113917 reaction equation
CN1CCOCC1.[N+:8]([C:11]1[N:12]([CH2:16][C:17]([OH:19])=O)[CH:13]=[CH:14][N:15]=1)([O-:10])=[O:9].ClC(OCC(C)C)=O.Cl.[F:29][C:30](=[CH2:33])[CH2:31][NH2:32]>C1COCC1>[N+:8]([C:11]1[N:12]([CH2:16][C:17]([NH:32][CH2:31][C:30]([F:29])=[CH2:33])=[O:19])[CH:13]=[CH:14][N:15]=1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 79724-Methylmorpholine2×HCID 62365Isobutyl chloroformateHCID 3275442-(2-Nitroimidazol-1-yl)acetic acidHCID 167237042-Fluoroprop-2-en-1-amine hydrochloride

Product 1

HCID 21111685HCID 21111685, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-methylmorpholine (1.01 g, 10 mmol) was added to 2-(2-nitro-1H-imidazol-1-yl)-acetic acid (1.71 g, 10 mmol) in 150 mL of dry THF under nitrogen at 0° C. and stirred for 10 minutes. Isobutyl chloroformate (1.43 mL, 11 mmol) was added. After 30 minutes, 2-fluoro allyl amine hydrochloride (1.23 g, 11 mmol) and N-methylmorpholine (1.21 g, 12 mmol) was added to the solution and the mixture was stirred at room temperature overnight. The solution was filtered and the organic solvent evaporated to give a yellow solid. Purified by column afforded a light yellow solid (1.1 g, 50%).

Workup

  1. waitAfter 30 minutes
  2. stirringthe mixture was stirred at room temperature overnight
  3. filtrationThe solution was filtered
  4. customthe organic solvent evaporated
  5. customto give a yellow solid
  6. customPurified by column

Sources & evidence

ORD record
ord-7ff87455f0c2433bb8541c6fef7d8231
Source dataset
uspto-grants-2008_10
Patent number
US07432295B2

Reaction notes

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