Potassium Phosphate, Tribasic → 9-(3-Dimethylamino-propylamino)-5-ethyl-5H-phenanthridin-6-one

HRID 968286Notes

Reaction equation

HRID 968286 reaction equation
CN[C:3]([NH:8][CH3:9])(N)[CH2:4][CH2:5][NH2:6].Cl[C:11]1[CH:24]=[C:23]2[C:14]([C:15](=[O:27])[N:16]([CH2:25][CH3:26])[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=32)=[CH:13][CH:12]=1.[CH:28]1(P(C2CCCCC2)C2C=C(C3C=CC=CC=3N(C)C)C=CC=2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:28][N:8]([CH3:9])[CH2:3][CH2:4][CH2:5][NH:6][C:11]1[CH:24]=[C:23]2[C:14]([C:15](=[O:27])[N:16]([CH2:25][CH3:26])[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=32)=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 22288550(3'-Dicyclohexylphosphanylbiphenyl-2-yl)dimethylamineHCID 222885519-chloro-5-ethyl-5H-phenanthridin-6-oneHCID 865929831,1-Dimethylamino-1,3-propanediamine

Product 1

HCID 222885469-(3-Dimethylamino-propylamino)-5-ethyl-5H-phenanthridin-6-oneYield 1,174.9%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

1,1-Dimethylamino-1,3-propanediamine (0.058 ml, 0.46 mmol) was added to a suspension of 9-chloro-5-ethyl-5H-phenanthridin-6-one I-14b (100 mg, 0.39 mmol), Pd2(dba)3 (2 mg, 0.002 mmol), (3′-dicyclohexylphosphanylbiphenyl-2-yl)dimethylamine (2.5 mg, 0.005 mmol), and dibasic potassium phosphate (115 mg, 0.54 mmol) in 1,2-dimethoxyethane (5 ml). The resultant suspension was held at 23° C. for 16 hours. The reaction mixture was concentrated in vacuo and the residue was purified by flash column chromatography (10% ethyl acetate in dichloromethane) to afford 9-(3-Dimethylamino-propylamino)-5-ethyl-5H-phenanthridin-6-one 14A (19 mg, 15%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by flash column chromatography (10% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-e681dddb98ae4b728848a4f3e164f81f
Source dataset
uspto-grants-2005_10
Patent number
US06958347B2

Reaction notes

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