4-Methylmorpholine → HCID 67128469, compound

HRID 1971772Notes

Reaction equation

HRID 1971772 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH:7]([CH3:11])[C:8]([OH:10])=O.[CH3:12]N(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:36][O:37][C:38](=[O:46])[C:39]1[CH:44]=[CH:43][C:42]([NH2:45])=[CH:41][CH:40]=1.CN1CCOCC1>CN(C=O)C.C(OCC)(=O)C>[CH3:12][N:45]([C:42]1[CH:43]=[CH:44][C:39]([C:38]([O:37][CH3:36])=[O:46])=[CH:40][CH:41]=1)[C:8](=[O:10])[CH:7]([N:3]1[CH2:4][CH2:5][CH2:6][C:2]1=[O:1])[CH3:11]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 12082Methyl 4-aminobenzoateHCID 30187022-(2-Oxopyrrolidin-1-yl)propanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 67128469HCID 67128469, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

To 2-(2-oxopyrrolidin-1-yl)propanoic acid (942 mgs, 6.0 mmol) in DMF (8 mL), was added HATU (2.4 g, 6.4 mmol), 4-Amino-benzoic acid methyl ester (660 mg, 4.0 mmol) and NMM (1.8 mL, 16.0 mmol) and stirred at 55° C. for 16 hours. The reaction mixture was diluted with ethyl acetate (100 mL) and washed with 1 N HCl, saturated NaHCO3, water, brine and dried over MgSO4. Filtration and concentration gave methyl 4-(N-methyl-2-(2-oxopyrrolidin-1-yl)propanamido)benzoate.

Workup

  1. washwashed with 1 N HCl, saturated NaHCO3, water, brine
  2. dry with materialdried over MgSO4
  3. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-82d84bf0379a49348500162f84e9be63
Source dataset
uspto-grants-2013_04
Patent number
US08431610B2

Reaction notes

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