Hydrochloric Acid → HCID 10135495, compound

HRID 719202Notes

Reaction equation

HRID 719202 reaction equation
[CH3:1][N:2]([CH3:27])[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]([NH2:26])[C:17]2=[CH:16][CH:15]=3)[CH:11]=[CH:10][CH:9]=1)=[O:7].C=O.[C-:30]#[N:31].[K+].Cl.[CH3:34]O>O.C(=O)(O)[O-].[Na+]>[CH3:1][N:2]([CH3:27])[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]([NH:26][CH2:34][C:30]#[N:31])[C:17]2=[CH:16][CH:15]=3)[CH:11]=[CH:10][CH:9]=1)=[O:7]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 887MethanolHCID 9032Potassium CyanideHCID 10109109HCID 10109109, compound

Product 1

HCID 10135495HCID 10135495, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-amino-benzo[a]phenazine-11-carboxylic acid (2-dimethylamino-ethyl)-amide (69 mg) in methanol (10 mL) was added formaldehyde (37% solution, 11.0 mL), potassium cyanide (102 mg) and 2N HCl (1.0 mL). The reaction mixture was heated to 50° C. for 3 hours. The reaction mixture was then cooled, diluted with water and sodium bicarbonate solution, extracted into dichloromethane, dried (MgSO4) and the solvent removed in vacuo to yield crude product. This was purified using flash chromatography (10% methanol in dichloromethane) to yield the title compound as a violet coloured solid (13 mg).

Workup

  1. temperatureThe reaction mixture was then cooled
  2. extractionextracted into dichloromethane
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customto yield crude product
  6. customThis was purified

Sources & evidence

ORD record
ord-6224340cfdd24f59aa8e467c34cae47f
Source dataset
uspto-grants-2006_11
Patent number
US07132419B2

Reaction notes

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