Water → HCID 59317726, compound

HRID 472732Notes

Reaction equation

HRID 472732 reaction equation
[C:1]([O:5][C:6](=[O:20])[CH2:7][N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][C:9]1=[O:19])([CH3:4])([CH3:3])[CH3:2].Br[CH2:22][C:23]([NH:25][C:26]1[CH:31]=[C:30]([Cl:32])[N:29]=[C:28]([Cl:33])[CH:27]=1)=[O:24].C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[C:1]([O:5][C:6](=[O:20])[CH2:7][N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:22][C:23](=[O:24])[NH:25][C:26]2[CH:31]=[C:30]([Cl:32])[N:29]=[C:28]([Cl:33])[CH:27]=2)[C:9]1=[O:19])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 53432550tert-Butyl (2,4-dioxo-1,4-dihydroquinazolin-3(2H)-yl)acetate2×HCID 86641477HCID 86641477, compound2×

Product 1

HCID 59317726HCID 59317726, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture comprising (2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-acetic acid tert-butyl ester (Intermediate L) (226.7 mg, 0.82 mmol), 2-bromo-N-(2,6-dichloro-pyridine-4-yl)-acetamide (Intermediate N) (256.5 mg, 0.902 mmol) and Cs2CO3 (545.1 mg, 1.64 mmol) in DMF (5 ml) is stirred at RT for 3 hours. The resulting mixture is treated with water and the precipitate is filtered under vacuum. The solid is washed with water, iso-hexane and then dried to give the title compound, [M+H]+ 479

Workup

  1. filtrationthe precipitate is filtered under vacuum
  2. washThe solid is washed with water, iso-hexane
  3. customdried

Sources & evidence

ORD record
ord-687fad0e6a054041962efb0d62869552
Source dataset
uspto-grants-2014_01
Patent number
US08633211B2

Reaction notes

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