Methylamine → HCID 10504612, compound

HRID 1899997Notes

Reaction equation

HRID 1899997 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-aabdd67a766b44a38a092a1d8cbcde72
Source dataset
uspto-grants-1996_11
Patent number
US05574042

Reaction notes

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