Acetic Acid → HCID 18329325, compound

HRID 1250009Notes

Reaction equation

HRID 1250009 reaction equation
[NH2:1][C:2]1[C:3]([CH3:23])=[C:4]([C:8]2[CH:9]=[C:10]([CH3:22])[C:11]([N:14]([CH3:21])[C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])=[N:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1.C(O)(=O)C.[CH2:28]([O:30][C:31]1(O[Si](C)(C)C)[CH2:33][CH2:32]1)C>CO>[CH3:28][O:30][C:31]1([NH:1][C:2]2[C:3]([CH3:23])=[C:4]([C:8]3[CH:9]=[C:10]([CH3:22])[C:11]([N:14]([CH3:21])[C:15](=[O:20])[C:16]([CH3:18])([CH3:19])[CH3:17])=[N:12][CH:13]=3)[CH:5]=[CH:6][CH:7]=2)[CH2:33][CH2:32]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 18329344HCID 18329344, compound

Product 1

HCID 18329325HCID 18329325, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 5.70 g of N-[5-(3-amino-2-methyl-phenyl)-3-methyl-2-pyridyl]-N,2,2-trimethylpropanamide in 34.2 ml of methanol were added 4.40 g of acetic acid and 4.32 g of 1-ethoxy-1-trimethylsilyloxycyclopropane and the mixture was refluxed for 7 hours under a nitrogen atmosphere. Concentration of the reaction mixture under reduced pressure afforded 6.98 g of N-(5-{3-[(1-methoxycyclopropyl)amino]-2-methylphenyl}-3-methyl-2-pyridyl)-N,2,2-trimethylpropanamide.

Workup

  1. temperaturethe mixture was refluxed for 7 hours under a nitrogen atmosphere

Sources & evidence

ORD record
ord-cb080a354820424a9de311527111b81a
Source dataset
uspto-grants-2002_01
Patent number
US06335447B1

Reaction notes

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