Triethylamine → HCID 21097052, compound

HRID 490252Notes

Reaction equation

HRID 490252 reaction equation
[CH2:1]([N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][C:13]([Cl:19])=[CH:14][CH:15]=2)[N:10]=[C:9]1[CH:20]([NH:24][CH2:25][C:26](=[O:40])[CH2:27][CH2:28][N:29]1[C:37](=[O:38])[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:30]1=[O:39])[CH:21]([CH3:23])[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:48]1([CH3:57])[CH:53]=[CH:52][C:51]([C:54](Cl)=[O:55])=[CH:50][CH:49]=1>C(Cl)Cl>[CH2:1]([N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][C:13]([Cl:19])=[CH:14][CH:15]=2)[N:10]=[C:9]1[CH:20]([N:24]([CH2:25][C:26](=[O:40])[CH2:27][CH2:28][N:29]1[C:37](=[O:38])[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:30]1=[O:39])[C:54](=[O:55])[C:51]1[CH:52]=[CH:53][C:48]([CH3:57])=[CH:49][CH:50]=1)[CH:21]([CH3:23])[CH3:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 134054-Methylbenzoyl ChlorideHCID 690786472-{4-[1-(3-Benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-2-methyl-propylamino]-3-oxo-butyl}-isoindole-1,3-dione

Product 1

HCID 21097052HCID 21097052, compoundYield 42.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-{4-[1-(3-benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-2-methyl-propylamino]-3-oxo-butyl}-isoindole-1,3-dione (1.5 g from previous step), triethylamine (245 mg, 2.42 mmol), and p-toluoyl chloride (374 mg, 2,42 mmol) in methylene chloride (10 mL) was stirred at room temperature for 2.0 h. The reaction was washed sequentially with 0.5 N HCl, water, 5% NaHCO3, water, and brine and dried (Na2SO4). The filtrate was concentrated in vacuo and purified by flash chromatography (silica gel 3:2 hexanes:EtOAc as eluent) to provide the title compound as a white solid (0.7 g, 35%, 2 steps). MS(ES+) m/e 675 [M+H]+.

Workup

  1. washThe reaction was washed sequentially with 0.5 N HCl, water, 5% NaHCO3, water, and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationThe filtrate was concentrated in vacuo
  4. custompurified by flash chromatography (silica gel 3:2 hexanes:EtOAc as eluent)

Sources & evidence

ORD record
ord-4f96f855b6fa40a280996f4d3a273420
Source dataset
uspto-grants-2009_05
Patent number
US07528137B2

Reaction notes

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