Hydrochloric Acid → HCID 178483816, compound

HRID 719190Notes

Reaction equation

HRID 719190 reaction equation
[CH3:1][N:2]([CH3:28])[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][C:24]([O:26]C)=[CH:25][C:17]2=[CH:16][CH:15]=3)[CH:11]=[CH:10][CH:9]=1)=[O:7].[S-]CC.[Na+].Cl>CN(C)C=O>[CH3:1][N:2]([CH3:28])[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][C:24]([OH:26])=[CH:25][C:17]2=[CH:16][CH:15]=3)[CH:11]=[CH:10][CH:9]=1)=[O:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4459711Sodium ethanethiolateHCID 10199414HCID 10199414, compound

Product 1

HCID 178483816HCID 178483816, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-methoxy-benzo[a]phenazine-11-carboxylic acid (2-dimethylamino-ethyl)-amide (170 mg) in dry N,N-dimethylformamide (3 mL) was added sodium thioethoxide (380 mg). The reaction mixture was then heated to reflux under argon for 3 hours. The reaction mixture was cooled, acidified (dilute HCl) and volatiles removed in vacuo. The residue was purified using column chromatography (20% methanol in dichloromethane) to yield the title compound as a red solid (142 mg).

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux under argon for 3 hours
  3. temperatureThe reaction mixture was cooled
  4. customvolatiles removed in vacuo
  5. customThe residue was purified

Sources & evidence

ORD record
ord-a06d3c803cdc405a8cf02f991f9decb3
Source dataset
uspto-grants-2006_11
Patent number
US07132419B2

Reaction notes

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