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Dimethylformamide → (R)-3-[1-(4,6-dimethyl-1,2-benzisothiazol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-butyric acid methyl ester

HRID 388469
Notes
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Reaction equation

HRID 388469 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH2:4][C@H:5]([N:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]1=[O:18])[CH3:6].Br[CH2:21][C:22]1[C:26]2[C:27]([CH3:32])=[CH:28][C:29]([CH3:31])=[CH:30][C:25]=2[S:24][N:23]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH3:1][O:2][C:3](=[O:19])[CH2:4][C@H:5]([N:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([CH2:21][C:22]2[C:26]3[C:27]([CH3:32])=[CH:28][C:29]([CH3:31])=[CH:30][C:25]=3[S:24][N:23]=2)[C:8]1=[O:18])[CH3:6]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 584973913-Bromomethyl-4,6-dimethyl-benzo[d]isothiazoleHCID 68728457(R)-3-(2,4-Dioxo-1,4-dihydro-2H-quinazolin-3-yl)-butyric acid methyl ester

Product 1

HCID 68751053(R)-3-[1-(4,6-dimethyl-1,2-benzisothiazol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-butyric acid methyl ester
Yield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(R)-3-(2,4-Dioxo-1,4-dihydro-2H-quinazolin-3-yl)-butyric acid methyl ester (124 mg, 0.5 mmol) (prepared according to example 4, steps 1-2), 3-bromomethyl-4,6-dimethyl-1,2-benzisothiazole (150 mg, 0.59 mmol) (prepared according to example 5, steps 1-6), and potassium carbonate (345.5 mg, 2.5 mmol) are combined in a reaction vial and DMF (1 mL) is added. The reaction mixture is agitated at ambient temperature for 18 hours then diluted with water (15 mL). The product is isolated by filtration and purified by flash chromatography using an ethyl acetate/hexane gradient to provide (R)-3-[1-(4,6-dimethyl-1,2-benzisothiazol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-butyric acid methyl ester (196 mg, 93%).

Workup

  1. additionis added
  2. customThe product is isolated by filtration
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-c6a92ba26d4c4c9f9edd014e772ef8a5
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08377949B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes