2-Butanamine, 1-methoxy- → HCID 22249609, compound

HRID 966050Notes

Reaction equation

HRID 966050 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([C:12]3[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=3[CH3:20])[CH:8]=[CH:9][N:10]=2)[N:5]=[C:4]([CH3:21])[C:3]=1[CH2:22][CH2:23]Cl.[NH2:25][CH:26]([CH2:30][CH3:31])[CH2:27][O:28][CH3:29]>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[CH3:29][O:28][CH2:27][CH:26]([N:25]1[C:2]2[C:11]3[N:10]=[CH:9][CH:8]=[C:7]([C:12]4[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=4[CH3:20])[C:6]=3[N:5]=[C:4]([C:21]3[C:13]([CH3:14])=[CH:12][C:7]([CH3:8])=[CH:6][C:11]=3[CH3:2])[C:3]=2[CH:22]=[CH:23]1)[CH2:30][CH3:31]

Participants

5

Reactant 2

HCID 938372-Butanamine, 1-methoxy-HCID 22249907HCID 22249907, compound

Product 1

HCID 22249609HCID 22249609, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

A solution of 4-chloro-3-(2-chloroethyl)-8-mesityl-2-methyl[1,5]naphthyridine (200 mg, 0.557 mmol) in 2-amino-1-methoxybutane (2.0 mL) was stirred at 200° C. for four hours in a sealed tube. After evaporating, the residue was purified by silica gel column chromatography (30-50% ethyl acetate/hexane). Activated manganese dioxide (290 mg, 3.24 mmol) was added to a solution of the resulting product (130 mg, 0.33 mmol) in toluene (20 mL) and the mixture was heated under reflux for one day. After filtering through Celite, the mixture was evaporated. The residue was purified by silica gel column chromatography (10% ethyl acetate/hexane), to give the title compound (108 mg) as white crystals.

Workup

  1. customAfter evaporating
  2. customthe residue was purified by silica gel column chromatography (30-50% ethyl acetate/hexane)
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for one day
  5. filtrationAfter filtering through Celite
  6. customthe mixture was evaporated
  7. customThe residue was purified by silica gel column chromatography (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-b4777ae673454bc3bb681aab632b04a4
Source dataset
uspto-grants-2005_10
Patent number
US06951865B2

Reaction notes

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