HCID 10112144, compound → HCID 10294648, compound

HRID 719207Notes

Reaction equation

HRID 719207 reaction equation
[CH3:1][N:2]([CH3:29])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:21]2[C:12](=[N:13][C:14]3[C:19]([N:20]=2)=[C:18]2[CH:22]=[CH:23][CH:24]=[C:25]([O:26][CH3:27])[C:17]2=[CH:16][CH:15]=3)[CH:11]=[C:10](Cl)[CH:9]=1)=[O:7].[CH3:30][O-:31].[Na+]>CO.C(OCC)(=O)C>[CH3:1][N:2]([CH3:29])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:21]2[C:12](=[N:13][C:14]3[C:19]([N:20]=2)=[C:18]2[CH:22]=[CH:23][CH:24]=[C:25]([O:26][CH3:27])[C:17]2=[CH:16][CH:15]=3)[CH:11]=[C:10]([O:31][CH3:30])[CH:9]=1)=[O:7]

Participants

5

Reactant 2

HCID 10112144HCID 10112144, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 10294648HCID 10294648, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 9-chloro-4-methoxy-benzo[a]phenazine-11-carboxylic acid (2-dimethylamino-ethyl)-amide (85 mg) and a 25% solution of sodium methoxide in methanol (4 mL) was heated to reflux for 6 hours. The reaction mixture was then cooled, diluted with ethyl acetate, washed with water, dried (MgSO4) and the solvent removed in vacuo to yield a yellow solid which was purified using flash chromatography to yield the desired title compound (42 mg).

Workup

  1. temperatureto reflux for 6 hours
  2. temperatureThe reaction mixture was then cooled
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customto yield a yellow solid which
  7. customwas purified

Sources & evidence

ORD record
ord-13c3dd1140164cc1b0bb66b72bf8cba9
Source dataset
uspto-grants-2006_11
Patent number
US07132419B2

Reaction notes

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