Dipropylamine → HCID 9946468, compound

HRID 2086011Notes

Reaction equation

HRID 2086011 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].[CH2:21]([NH:24][CH2:25][CH2:26][CH3:27])[CH2:22][CH3:23].O=C1C2C(=CC=CC=2)C2C(CC(N)=O)=CC=CC=2N1.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:24]([CH2:25][CH2:26][CH3:27])[CH2:21][CH2:22][CH3:23])[CH:19]=[CH:18][C:17]=2[NH:16]1

Participants

6

Reactant 4

HCID 8902Dipropylamine2×HCID 62657Potassium Phosphate, TribasicHCID 9814438N-(6-oxo-5,6-dihydro-phenanthridin-2-yl)-chloroacetamideHCID 86759421HCID 86759421, compound

Product 1

HCID 9946468HCID 9946468, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared from the compound of Example 2 and dipropylamine. 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 dipropylamine (0.027 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 (25 mg). 1H-NMR (300 MHz, DMSO-d6), 11.70 (br s, 1H), 9.72 (br s, 1H), 8.33 (d, J=8.0 Hz, 2H), 7.89 (m, 1), 7.66 (m, 2H), 7.33 (m, 1H), 3.21 (s, 2H), 1.50 (m, 6H), 0.89 (m, 8H).

Workup

  1. customfollowed by evaporation of the solvent
  2. washThe light brown product was washed with water
  3. filtrationfiltered (25 mg)

Sources & evidence

ORD record
ord-d075d9bfda8a4d7badb1a54bc1cbaf1e
Source dataset
uspto-grants-2004_04
Patent number
US06723733B2

Reaction notes

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