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

HRID 390197Notes

Reaction equation

HRID 390197 reaction equation
[NH2:1][C:2]1[CH:21]=[CH:20][C:19]([C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:18][C:3]=1[CH2:4][NH:5][CH2:6][CH2:7][C:8]([N:10]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[CH3:11])=[O:9].[N:30]#[C:31]Br>CO>[NH2:30][C:31]1[N:5]([CH2:6][CH2:7][C:8]([N:10]([CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[CH3:11])=[O:9])[CH2:4][C:3]2[C:2](=[CH:21][CH:20]=[C:19]([C:22](=[O:29])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:18]=2)[N:1]=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

To a solution of 3-(2-amino-5-benzoyl-benzylamino)-N-cyclohexyl-N-methyl-propionamide (3.94 g, 0.0100 mol) in methanol (200 mL) was added cyanogen bromide (1.16 g, 0.0110 mol). The resulting mixture was stirred at room temperature over the weekend and then was heated at reflux for 5 h. The solvent was evaporated to yield a residue that was crystallized from EtOAc (100 mL). The resulting precipitate was filtered and dried to yield crude product that was recrystallized from 2-propanol (50 mL) to yield the title compound, 3-(2-amino-6-benzoyl-4H-quinazolin-3-yl)-N-cyclohexyl-N-methyl-propionamide.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 h
  3. customThe solvent was evaporated
  4. customto yield a residue that
  5. customwas crystallized from EtOAc (100 mL)
  6. filtrationThe resulting precipitate was filtered
  7. customdried
  8. customto yield crude product that
  9. customwas recrystallized from 2-propanol (50 mL)

Sources & evidence

ORD record
ord-3f18b05074fd4f97863bc684e8acce8d
Source dataset
uspto-grants-2013_02
Patent number
US08383637B2

Reaction notes

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