Bromoacetonitrile → HCID 10157757, compound

HRID 719191Notes

Reaction equation

HRID 719191 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]([OH:26])[C:17]2=[CH:16][CH:15]=3)[CH:11]=[CH:10][CH:9]=1)=[O:7].CC(C)([O-])C.[K+].Br[CH2:35][C:36]#[N:37]>CN(C)C=O.C(OCC)(=O)C>[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]([O:26][CH2:35][C:36]#[N:37])[C:17]2=[CH:16][CH:15]=3)[CH:11]=[CH:10][CH:9]=1)=[O:7]

Participants

6

Reactant 3

HCID 11534BromoacetonitrileHCID 23665647Potassium tert-butoxideHCID 178483817HCID 178483817, compound

Product 1

HCID 10157757HCID 10157757, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of 4-hydroxy-benzo[a]phenazine-11-carboxylic acid (2-dimethylamino-ethyl)-amide: hydrobromide salt (230 mg) in dry N,N-dimethylformamide (3 mL) was added potassium tert-butoxide (175 mg) and then bromoacetonitrile (47 μL). The reaction mixture was heated to 100° C. for 1 hour. The reaction mixture was then cooled, diluted with ethyl acetate, washed with sodium carbonate solution and brine, dried (MgSO4) and the solvent removed in vacuo to provide crude product. This was purified using flash chromatography (silica, 25% MeOH in ethyl acetate) to yield the title compound as a yellow solid (74 mg).

Workup

  1. temperatureThe reaction mixture was then cooled
  2. washwashed with sodium carbonate solution and brine
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customto provide crude product
  6. customThis was purified

Sources & evidence

ORD record
ord-89a7693c2e8348218db6817249217a0a
Source dataset
uspto-grants-2006_11
Patent number
US07132419B2

Reaction notes

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