Methylamine → HCID 11232543, compound

HRID 380168Notes

Reaction equation

HRID 380168 reaction equation
C1C=C2C([N:9]([CH2:12][C:13](O)=[O:14])C(=O)C2=CC=1)=O.S(Cl)(Cl)=O.[CH2:20]([NH:24][C:25]1[C:30]([C:31](=O)[C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[CH:33]=2)=[CH:29][CH:28]=[CH:27][N:26]=1)[CH2:21][CH2:22][CH3:23].C(=O)([O-])[O-].[K+].[K+].CN>C1(C)C=CC=CC=1.N1C=CC=CC=1.O.CN(C)C=O>[CH2:20]([N:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][N:26]=2)[C:31]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[CH:33]=2)=[C:12]([NH2:9])[C:13]1=[O:14])[CH2:21][CH2:22][CH3:23]

Participants

10

Reactant 5

HCID 6329MethylamineHCID 11430Potassium CarbonateHCID 20825N-PhthaloylglycineHCID 24386Thionyl ChlorideHCID 11426125Methanone, [2-(butylamino)-3-pyridinyl](3-methoxyphenyl)-

Product 1

HCID 11232543HCID 11232543, compoundYield 61.3%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1049PyridineSolventHCID 1140TolueneSolvent2×HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
55 °C

Procedure

To a suspension of N-phthaloylglycine (4.76 g, 23.2 mmol) in toluene (24 ml) were added thionyl chloride (5.08 ml, 69.6 mmol) and dimethylformamide (0.4 ml), and the mixture was stirred at 50-60° C. for 30 minutes, cooled, and concentrated under reduced pressure to remove the solvent. To the resulting solid was added toluene (12 ml), and further thereto were added a solution of 2-(butylamino)-3-(3-methoxybenzoyl)pyridine (3.30 g, 11.6 mmol) in toluene (15 ml) and pyridine (27 ml), and the mixture was stirred at 80-90° C. for 2 hours. After allowed to cool, to the mixture were added potassium carbonate (9.62 g, 69.6 mmol) and N,N-dimethylformamide (54 ml), and the mixture was further stirred at 90-100° C. for 8 hours. After allowed to cool, a 40% aqueous methylamine solution (4.99 ml, 58.0 mmol) was added, and the mixture was stirred at room temperature for one hour. Water was added to the reaction solution, and the mixture was extracted with toluene. The extract was washed successively with 1N hydrochloric acid, water, a 5% aqueous sodium hydrogen carbonate solution and a 5% aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting solid was recrytallized from 2-propanol to give the title compound (2.30 g, 7.11 mmol, 61%) as colorless prisms.

Workup

  1. temperaturecooled
  2. concentrationconcentrated under reduced pressure
  3. customto remove the solvent
  4. additionTo the resulting solid was added toluene (12 ml)
  5. stirringthe mixture was stirred at 80-90° C. for 2 hours
  6. temperatureto cool, to the mixture
  7. stirringthe mixture was further stirred at 90-100° C. for 8 hours
  8. temperatureto cool
  9. stirringthe mixture was stirred at room temperature for one hour
  10. extractionthe mixture was extracted with toluene
  11. washThe extract was washed successively with 1N hydrochloric acid, water
  12. dry with materiala 5% aqueous sodium hydrogen carbonate solution and a 5% aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-909511494c6942309c0689cb4e455918
Source dataset
uspto-grants-2001_10
Patent number
US06300500B1

Reaction notes

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