Morpholine → HCID 10268699, compound

HRID 2086014Notes

Reaction equation

HRID 2086014 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:19]=[CH:18][C:17]2[NH:16][C:15](=[O:20])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]=2[CH:7]=1)=[O:4].[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C)C=O>[O:20]=[C:15]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]2[CH:7]=[C:6]([NH:5][C:3](=[O:4])[CH2:2][N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[CH:19]=[CH:18][C:17]=2[NH:16]1

Participants

5

Reactant 3

HCID 8083Morpholine2×HCID 62657Potassium Phosphate, TribasicHCID 9814438N-(6-oxo-5,6-dihydro-phenanthridin-2-yl)-chloroacetamide2×

Product 1

HCID 10268699HCID 10268699, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared from the compound of Example 2 and morpholine. To a solution of 2-chloro-N-(5,6-dihydro-6-oxo-2-phenanthridinyl)-acetamide (45 mg) in N,N-dimethylformamide (10 mL) was added potassium phosphate (68 mg) and morpholine (0.017 mL). The solution stirred at room temperature for 5 hours followed by evaporation of the solvent. The light brown product was washed with water and filtered (30 mg). 1H-NMR (300 MHz, DMSO-d6), 11.68 (br s, 1H), 9.85 (br s, 1H), 8.64 (s, 1H), 8.33 (d, J=9.0 Hz, 2H), 7.89 (t, 1H), 7.77 (d, J=9.0 Hz, 1H), 7.66 (t, 1H), 7.32 (d, J=9.0 Hz, 1H), 3.68 (d, 4), 3.17 (s, 2H), 2.55 (m, 4H).

Workup

  1. customfollowed by evaporation of the solvent
  2. washThe light brown product was washed with water
  3. filtrationfiltered (30 mg)

Sources & evidence

ORD record
ord-3d92d85bed694f5c92f25bf96d002e02
Source dataset
uspto-grants-2004_04
Patent number
US06723733B2

Reaction notes

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