Dimethylformamide → 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

HRID 1350630Notes

Reaction equation

HRID 1350630 reaction equation
N[CH2:2][CH2:3][C:4]1[N:5]=[C:6]([C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)[N:7]([CH:9]([C:13]2[N:22]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:21](=[O:30])[C:20]3[C:15](=[CH:16][C:17]([Cl:31])=[CH:18][CH:19]=3)[N:14]=2)[CH:10]([CH3:12])[CH3:11])[CH:8]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:46][C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48].C[N:55](C=O)C>O>[C:50]([O:49][C:47](=[O:48])[CH2:46][NH:55][CH:3]([C:4]1[N:5]=[C:6]([C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)[N:7]([CH:9]([C:13]2[N:22]([CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:21](=[O:30])[C:20]3[C:15](=[CH:16][C:17]([Cl:31])=[CH:18][CH:19]=3)[N:14]=2)[CH:10]([CH3:11])[CH3:12])[CH:8]=1)[CH3:2])([CH3:53])([CH3:52])[CH3:51]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 210969872-{1-[4-(2-Amino-ethyl)-2-p-tolyl-imidazol-1-yl]-2-methyl-propyl}-3-benzyl-7-chloro-3H-quinazolin-4-one

Product 1

HCID 865918912-{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 esterYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-{1-[4-(2-Amino-ethyl)-2-p-tolyl-imidazol-1-yl]-2-methyl-propyl}-3-benzyl-7-chloro-3H-quinazolin-4-one (181 mg, 0.343 mmol), potassium carbonate (47 mg., 0.343 mmol), and tert-butyl bromoacetate (67 mg., 0.343 mmol) in DMF (2.0 mL) was stirred at room temperature for 4.5 h. The reaction was diluted with water and the resulting white precipitate was filtered and purified by flash chromatography ( silica gel, 95:5 methylene chloride: methanol) to provide the title compound as a white solid (109 mg., 50%). MS(ES+) m/e 640 [M+H]+.

Workup

  1. filtrationthe resulting white precipitate was filtered
  2. custompurified by flash chromatography ( silica gel, 95:5 methylene chloride: methanol)

Sources & evidence

ORD record
ord-d36cc69bd97f43dc80292a2320b1212b
Source dataset
uspto-grants-2007_05
Patent number
US07214800B2

Reaction notes

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