4-Methylmorpholine → HCID 42626054, compound

HRID 905642Notes

Reaction equation

HRID 905642 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:25]([O:29][C:30](=[O:39])[NH:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[NH2:38])([CH3:28])([CH3:27])[CH3:26].[CH3:40][O:41][C:42]([C:44]1[CH:45]=[CH:46][C:47]([C:50](O)=[O:51])=[N:48][CH:49]=1)=[O:43].CN1CCOCC1>CN(C=O)C.O>[C:25]([O:29][C:30]([NH:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[NH:38][C:50]([C:47]1[CH:46]=[CH:45][C:44]([C:42]([O:41][CH3:40])=[O:43])=[CH:49][N:48]=1)=[O:51])=[O:39])([CH3:28])([CH3:26])[CH3:27]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 3149925-(Methoxycarbonyl)pyridine-2-carboxylic acidHCID 676311N-(tert-Butoxycarbonyl)-1,2-phenylenediamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 42626054HCID 42626054, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

HATU (21 g, 55 mmol) was added to a solution of 2-aminophenylcarbamic acid t-butyl ester (Reference Compound No. 1-1, 10 g, 50 mmol), 5-methoxycarbonylpyridine-2-carboxylic acid (10 g, 55 mmol), and N-methylmorpholine (11 mL, 100 mmol) in DMF (100 mL), and then the reaction mixture was stirred at room temperature for 20 hours. Water (300 mL) was added thereto, and then the whole was extracted with ethyl acetate (300 mL) three times. The organic layer was washed with brine (200 mL), and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and then the obtained solid was collected by filtration to give 15 g of the title reference compound as a pale brown solid. (Yield 79%)

Workup

  1. extractionthe whole was extracted with ethyl acetate (300 mL) three times
  2. washThe organic layer was washed with brine (200 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. filtrationthe obtained solid was collected by filtration
  6. customto give 15 g of the title reference compound as a pale brown solid

Sources & evidence

ORD record
ord-c30380a723f447e7afeb7275c317bb34
Source dataset
uspto-grants-2011_09
Patent number
US08012972B2

Reaction notes

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