Cyanogen Bromide → [3-(2-Amino-3-propyl-3,4-dihydro-quinazolin-6-yloxy)-phenyl]-carbamic acid benzyl ester

HRID 1968811Notes

Reaction equation

HRID 1968811 reaction equation
[CH2:1]([O:8][C:9](=[O:30])[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]2[CH:23]=[CH:22][C:21]([NH2:24])=[C:20]([CH2:25][NH:26][CH2:27][CH2:28][CH3:29])[CH:19]=2)[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:31]#[C:32]Br>C(O)C>[CH2:1]([O:8][C:9](=[O:30])[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]2[CH:19]=[C:20]3[C:21](=[CH:22][CH:23]=2)[N:24]=[C:32]([NH2:31])[N:26]([CH2:27][CH2:28][CH3:29])[CH2:25]3)[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 58625165[3-(4-Amino-3-propylaminomethyl-phenoxy)-phenyl]-carbamic acid benzyl ester

Product 1

HCID 58625107[3-(2-Amino-3-propyl-3,4-dihydro-quinazolin-6-yloxy)-phenyl]-carbamic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of [3-(4-Amino-3-propylaminomethyl-phenoxy)-phenyl]-carbamic acid benzyl ester (0.032 mol) and cyanogen bromide (0.035 mol) in ethanol (250 mL) was stirred and refluxed for 2 hours, then the reaction mixture was cooled to room temperature and the solvent was evaporated. The residue was converted into its free base with a NaOH solution and the resulting mixture was extracted with CH2Cl2. The organic layer was separated and the solvent was evaporated, then the residue was stirred in diisopropyl ether, filtered off and dried under vacuum to yield the title compound as a solid.

Workup

  1. temperaturerefluxed for 2 hours
  2. customthe solvent was evaporated
  3. extractionthe resulting mixture was extracted with CH2Cl2
  4. customThe organic layer was separated
  5. customthe solvent was evaporated
  6. stirringthe residue was stirred in diisopropyl ether
  7. filtrationfiltered off
  8. customdried under vacuum

Sources & evidence

ORD record
ord-ee3e12d57af1497a834ce466d71dee41
Source dataset
uspto-grants-2013_04
Patent number
US08426429B2

Reaction notes

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