Dichloromethane → HCID 21096987, compound

HRID 1350619Notes

Reaction equation

HRID 1350619 reaction equation
[CH2:1]([N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12]C(Cl)=[CH:14][CH:15]=2)[N:10]=[C:9]1[CH:20]([NH:24][CH2:25][C:26](=O)[CH2:27][CH2:28][N:29]1C(=O)C2C(=CC=CC=2)C1=O)[CH:21]([CH3:23])[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:43](CC)CC)C.[C:48]1([CH3:57])[CH:53]=[CH:52][C:51]([C:54](Cl)=O)=[CH:50][CH:49]=1.[CH2:58]([Cl:60])Cl>>[NH2:29][CH2:28][CH2:27][C:26]1[N:43]=[C:54]([C:51]2[CH:52]=[CH:53][C:48]([CH3:57])=[CH:49][CH:50]=2)[N:24]([CH:20]([C:9]2[N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:17](=[O:18])[C:16]3[C:11](=[CH:12][C:58]([Cl:60])=[CH:14][CH:15]=3)[N:10]=2)[CH:21]([CH3:22])[CH3:23])[CH:25]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 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 21096987HCID 21096987, compoundYield 35%

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-27102faaee2241c3b37e5fc1edd01e1d
Source dataset
uspto-grants-2007_05
Patent number
US07214800B2

Reaction notes

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