Methylamine → HCID 10504612, compound

HRID 1290180Notes

Reaction equation

HRID 1290180 reaction equation
[Br:1][C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[C:10]([O:11][CH2:12][C:13]3[C:18]([Cl:19])=[CH:17][CH:16]=[C:15]([N:20]([CH3:33])[C:21](OC4C=CC([N+]([O-])=O)=CC=4)=[O:22])[C:14]=3[Cl:34])[C:5]2=[N:4][C:3]=1[CH3:35].[CH3:36][NH2:37]>CO>[Br:1][C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[C:10]([O:11][CH2:12][C:13]3[C:18]([Cl:19])=[CH:17][CH:16]=[C:15]([N:20]([CH3:33])[C:21]([NH:37][CH3:36])=[O:22])[C:14]=3[Cl:34])[C:5]2=[N:4][C:3]=1[CH3:35]

Participants

4

Reactant 2

HCID 6329Methylamine2×HCID 10817049HCID 10817049, compound

Product 1

HCID 10504612HCID 10504612, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of 3-bromo-8-[2,6-dichloro-3-[N-methyl-N-(4-nitrophenyloxycarbonyl)amino]benzyloxy]-2-methylimidazo[1,2-a]pyridine (63 mg) and 30% solution of methylamine in methanol (2 ml) was heated under reflux for 3 hours. After addition of 30% solution of methylamine in methanol (1 ml), the mixture was heated under reflux for additional 1 hour. The mixture was evaporated in vacuo and the residue was extracted with ethyl acetate. The extract was evaporated in vacuo and the residue was purified by preparative thin-layer chromatography (5% solution of methanol in dichloromethane) followed by crystallization from diethyl ether to give 3-bromo-8-[2,6-dichloro-3-(N-methyl-N'-methylureido)benzyloxy]-2-methylimidazo[1,2-a]pyridine (28 mg) as crystals.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for additional 1 hour
  5. customThe mixture was evaporated in vacuo
  6. extractionthe residue was extracted with ethyl acetate
  7. customThe extract was evaporated in vacuo
  8. customthe residue was purified by preparative thin-layer chromatography (5% solution of methanol in dichloromethane)
  9. customfollowed by crystallization from diethyl ether

Sources & evidence

ORD record
ord-f732dc9e3ae549949c9f760d7c85d37e
Source dataset
uspto-grants-1998_05
Patent number
US05750699

Reaction notes

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