Cyclohexanecarboxylic acid [2-(2-amino-5-benzoyl-benzylamino)-ethyl]-amide → Cyclohexanecarboxylic acid [2-(2-amino-6-benzoyl-4H-quinazolin-3-yl)-ethyl]-amide

HRID 1968780Notes

Reaction equation

HRID 1968780 reaction equation
[NH2:1][C:2]1[CH:20]=[CH:19][C:18]([C:21](=[O:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:17][C:3]=1[CH2:4][NH:5][CH2:6][CH2:7][NH:8][C:9]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:10].[Br].[N:30]#[C:31]C#N>C(O)C>[NH2:30][C:31]1[N:5]([CH2:6][CH2:7][NH:8][C:9]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:10])[CH2:4][C:3]2[C:2](=[CH:20][CH:19]=[C:18]([C:21](=[O:28])[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:17]=2)[N:1]=1

Participants

4

Reactant 2

HCID 58625175Cyclohexanecarboxylic acid [2-(2-amino-5-benzoyl-benzylamino)-ethyl]-amideHCID 178511328HCID 178511328, compound

Product 1

HCID 58625077Cyclohexanecarboxylic acid [2-(2-amino-6-benzoyl-4H-quinazolin-3-yl)-ethyl]-amide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of cyclohexanecarboxylic acid [2-(2-amino-5-benzoyl-benzylamino)-ethyl]-amide (0.0032 mol) in ethanol (30 mL) was stirred at room temperature. Cyanogen bromine (0.0048 mol) was added. The reaction mixture was stirred and refluxed for 2 hours, then cooled and stirred overnight at room temperature resulting in a precipitate. The precipitate was filtered off, washed with diisopropyl ether and dried to yield the title compound as a residue.

Workup

  1. stirringThe reaction mixture was stirred
  2. temperaturerefluxed for 2 hours
  3. temperaturecooled
  4. stirringstirred overnight at room temperature
  5. customresulting in a precipitate
  6. filtrationThe precipitate was filtered off
  7. washwashed with diisopropyl ether
  8. customdried

Sources & evidence

ORD record
ord-ae816875f1554525b150b0d9be3556b5
Source dataset
uspto-grants-2013_04
Patent number
US08426429B2

Reaction notes

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