Cyanogen Bromide → 3-(2-Amino-6-benzoylquinazolin-3(4H)-YL)-N-cyclohexyl-N-methylpropanamide

HRID 1968821Notes

Reaction equation

HRID 1968821 reaction equation
[N:1]#[C:2]Br.[NH2:4][C:5]1[CH:24]=[CH:23][C:22]([C:25](=[O:32])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:21][C:6]=1[CH2:7][NH:8][CH2:9][CH2:10][C:11]([N:13]([CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[CH3:14])=[O:12]>CO>[NH2:1][C:2]1[N:8]([CH2:9][CH2:10][C:11]([N:13]([CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]2)[CH3:14])=[O:12])[CH2:7][C:6]2[C:5](=[CH:24][CH:23]=[C:22]([C:25](=[O:32])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:21]=2)[N:4]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 586251113-(2-Amino-5-benzoyl-benzylamino)-N-cyclohexyl-N-methyl-propionamide

Product 1

HCID 167412383-(2-Amino-6-benzoylquinazolin-3(4H)-YL)-N-cyclohexyl-N-methylpropanamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Cyanogen bromide (0.011 mol) was added to a solution of 3-(2-amino-5-benzoyl-benzylamino)-N-cyclohexyl-N-methyl-propionamide (0.01 mol) in methanol (200 mL), stirred at room temperature. The reaction solution was stirred over a weekend at room temperature, then stirred and refluxed for an additional 5 h. The solvent was evaporated to yield a residue. The residue was crystallized from ethyl acetate (100 mLl). The resulting precipitate was filtered off and dried. The product fraction was recrystallized from 2-propanol (50 mL). The crystals were filtered off and dried to yield the title compound as a residue.

Workup

  1. stirringThe reaction solution was stirred over a weekend at room temperature
  2. stirringstirred
  3. temperaturerefluxed for an additional 5 h
  4. customThe solvent was evaporated
  5. customto yield a residue
  6. customThe residue was crystallized from ethyl acetate (100 mLl)
  7. filtrationThe resulting precipitate was filtered off
  8. customdried
  9. customThe product fraction was recrystallized from 2-propanol (50 mL)
  10. filtrationThe crystals were filtered off
  11. customdried

Sources & evidence

ORD record
ord-8e499b58efbd4df9b849cac07e6374b9
Source dataset
uspto-grants-2013_04
Patent number
US08426429B2

Reaction notes

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