Trifluoroacetic acid → (2-{1-[1-(3-Benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-2-methyl-propyl]-2-p-tolyl-1H-imidazol-4-yl}-ethylamino)-acetic acid

HRID 1350631Notes

Reaction equation

HRID 1350631 reaction equation
C([O:5][C:6](=[O:46])[CH2:7][NH:8][CH2:9][CH2:10][C:11]1[N:12]=[C:13]([C:39]2[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][CH:40]=2)[N:14]([CH:16]([C:20]2[N:29]([CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:28](=[O:37])[C:27]3[C:22](=[CH:23][C:24]([Cl:38])=[CH:25][CH:26]=3)[N:21]=2)[CH:17]([CH3:19])[CH3:18])[CH:15]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:30]([N:29]1[C:28](=[O:37])[C:27]2[C:22](=[CH:23][C:24]([Cl:38])=[CH:25][CH:26]=2)[N:21]=[C:20]1[CH:16]([N:14]1[CH:15]=[C:11]([CH2:10][CH2:9][NH:8][CH2:7][C:6]([OH:46])=[O:5])[N:12]=[C:13]1[C:39]1[CH:40]=[CH:41][C:42]([CH3:45])=[CH:43][CH:44]=1)[CH:17]([CH3:19])[CH3:18])[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58861276(2-{1-[1-(3-benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-2-methyl-propyl]-2-p-tolyl-1H-imidazol-4-yl}-ethylamino)-acetic acid tert-butyl ester

Product 1

HCID 21096985(2-{1-[1-(3-Benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-2-methyl-propyl]-2-p-tolyl-1H-imidazol-4-yl}-ethylamino)-acetic acidYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2-{1-[1-(3-benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-2-methyl-propyl]-2-p-tolyl-1H-imidazol-4-yl}-ethylamino)-acetic acid tert-butyl ester (99.6 mg., 0.155 mmol) and trifluoroacetic acid (8 mL) in methylene chloride (4 mL) was stirred at room temperature for 3.0 h. The reaction was concentrated in vacuo and the residue was triturated with diethyl ether and dried to provide the title compound as a white solid (67 mg., 53%). MS(ES+) m/e 584 [M+H]+.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe residue was triturated with diethyl ether
  3. customdried

Sources & evidence

ORD record
ord-f8a167c8b89d49fa9e753999218cf6a3
Source dataset
uspto-grants-2007_05
Patent number
US07214800B2

Reaction notes

Loading…