Morpholine → HCID 11395588, compound

HRID 2354176Notes

Reaction equation

HRID 2354176 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH:7]1([NH:10][C:11]([C:13]2[CH:14]=[CH:15][C:16]([CH3:32])=[C:17]([NH:19][C:20](=[O:31])[C:21]3[CH:26]=[C:25](F)[CH:24]=[CH:23][C:22]=3[N+:28]([O-])=O)[CH:18]=2)=[O:12])[CH2:9][CH2:8]1.[C:33]([O-])(O)=O.[Na+]>CS(C)=O>[CH:7]1([NH:10][C:11](=[O:12])[C:13]2[CH:14]=[CH:15][C:16]([CH3:32])=[C:17]([N:19]3[C:20](=[O:31])[C:21]4[C:22](=[CH:23][CH:24]=[C:25]([N:1]5[CH2:6][CH2:5][O:4][CH2:3][CH2:2]5)[CH:26]=4)[N:28]=[CH:33]3)[CH:18]=2)[CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 516892Sodium BicarbonateHCID 669189745-fluoro-N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-2-nitrobenzamide

Product 1

HCID 11395588HCID 11395588, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Morpholine (0.21 ml) was added to a stirred solution of N-(5-[(cyclopropylamino)carbonyl]-2-methylphenyl)-5-fluoro-2-nitrobenzamide (0.71 g) in DMSO (1.0 ml). The mixture was stirred at room temperature for 18 hours. The mixture was poured into a saturated NaHCO3 solution (100 ml) and the resultant solid was filtered and dried under vacuum at 40° C. There was thus obtained N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-5-morpholin-4-yl-2-nitrobenzamide (0.722 g); NMR Spectrum: (DMSOd6) 0.57 (m, 2H), 0.68 (m, 2H), 2.29 (s, 3H), 2.83 (m, 1H), 3.45 (m, 4H), 3.74 (m, 4H), 7.07 (m, 2H), 7.28 (m, 1H), 7.56 (m, 1H), 7.95 (s, 1H), 8.06 (d, 1H), 8.36 (s, 1H), 9.92 (s, 1H); Mass Spectrum: M+Na+ 447. B) 10% Palladium-on-carbon (0.050 g) was added to a stirred suspension of N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-5-morpholinyl-2-nitrobenzamide (0.722 g) in ethanol (10 ml) and the mixture was stirred under an atmosphere of hydrogen gas at a pressure of 10 bar. After cessation of hydrogen uptake, the catalyst was removed by filtration through diatomaceous earth (Celite®). The filtrate was concentrated under reduced pressure, which provided the crude 2-amino-N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-5-morpholin-4-ylbenzamide which was used without further purification; Mass Spectrum: M+H+ 395.

Workup

  1. filtrationthe resultant solid was filtered
  2. customdried under vacuum at 40° C
  3. additionB) 10% Palladium-on-carbon (0.050 g) was added to a stirred suspension of N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-5-morpholinyl-2-nitrobenzamide (0.722 g) in ethanol (10 ml)
  4. stirringthe mixture was stirred under an atmosphere of hydrogen gas at a pressure of 10 bar
  5. customAfter cessation of hydrogen uptake, the catalyst was removed by filtration through diatomaceous earth (Celite®)
  6. concentrationThe filtrate was concentrated under reduced pressure, which

Sources & evidence

ORD record
ord-907a146a90b9400396efc3b7e67d66ce
Source dataset
uspto-grants-2010_07
Patent number
US07750154B2

Reaction notes

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