2-Amino-1-dimethylaminopropane → 4-Methoxy-benzo[a]phenazine-11-carboxylic acid (2-dimethylamino-1-methyl-ethyl)-amide

HRID 719189Notes

Reaction equation

HRID 719189 reaction equation
C[O:2][C:3]([C:5]1[C:18]2[C:9](=[N:10][C:11]3[C:16]([N:17]=2)=[C:15]2[CH:19]=[CH:20][CH:21]=[C:22]([O:23][CH3:24])[C:14]2=[CH:13][CH:12]=3)[CH:8]=[CH:7][CH:6]=1)=O.[CH3:25][N:26]([CH3:31])[CH2:27][CH:28]([NH2:30])[CH3:29]>>[CH3:25][N:26]([CH3:31])[CH2:27][CH:28]([NH:30][C:3]([C:5]1[C:18]2[C:9](=[N:10][C:11]3[C:16]([N:17]=2)=[C:15]2[CH:19]=[CH:20][CH:21]=[C:22]([O:23][CH3:24])[C:14]2=[CH:13][CH:12]=3)[CH:8]=[CH:7][CH:6]=1)=[O:2])[CH3:29]

Participants

3

Reactant 2

HCID 990272-Amino-1-dimethylaminopropaneHCID 695968574-Methoxy-benzo[a]phenazine-11-carboxylic Acid Methyl Ester

Product 1

HCID 110903784-Methoxy-benzo[a]phenazine-11-carboxylic acid (2-dimethylamino-1-methyl-ethyl)-amide

Conditions

Temperature
110 °C

Procedure

A mixture of 4-methoxy-benzo[a]phenazine-11-carboxylic acid methyl ester (IV.1) (350 mg) and 1-dimethylamino-2-propylamine (2 mL)(commercially available) was heated to 110° C. under N2 for 4 hours. The reaction mixture was then cooled and the excess amine was removed in vacuo. The residue was then purified using flash chromatography (silica, ethyl acetate and then 25% methanol in ethyl acetate) to yield the title compound as a yellow solid (164 mg).

Workup

  1. temperatureThe reaction mixture was then cooled
  2. customthe excess amine was removed in vacuo
  3. customThe residue was then purified

Sources & evidence

ORD record
ord-49b3eaebe82e4b37adb2ebf63972057d
Source dataset
uspto-grants-2006_11
Patent number
US07132419B2

Reaction notes

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