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 490264Notes

Reaction equation

HRID 490264 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-344b926624374dcaaf94f6ca92489664
Source dataset
uspto-grants-2009_05
Patent number
US07528137B2

Reaction notes

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