Dimethylformamide → HCID 22727943, compound

HRID 2086013Notes

Reaction equation

HRID 2086013 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].CN[CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:37][N:38](C)C=O>>[CH:23]1([CH2:37][NH:38][CH2:2][C:3]([NH:5][C:6]2[CH:19]=[CH:18][C:17]3[NH:16][C:15](=[O:20])[C:14]4[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=4)[C:8]=3[CH:7]=2)=[O:4])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 7514N-Methylcyclohexylamine2×HCID 62657Potassium Phosphate, TribasicHCID 9814438N-(6-oxo-5,6-dihydro-phenanthridin-2-yl)-chloroacetamide2×

Product 1

HCID 22727943HCID 22727943, compound

Procedure

Prepared from the compound of Example 2 and N-methylcyclohexylamine. 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 N-methylcyclohexylamine (0.025 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), 11.69 (br s, 1H), 9.76 (br s, 1H), 8.65 (s, 1H), 8.34 (t, 2H), 7.87 (m, 2H), 7.66 (t, 1H), 7.32 (t, 1H), 3.18 (s, 2H), 2.34 (s, 3H), 1.80 (m, 4H), 1.60 (m, 2H), 1.23 (m, 5H).

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-e5e58ce656cb4c6fb484c93e8df5cc21
Source dataset
uspto-grants-2004_04
Patent number
US06723733B2

Reaction notes

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