Methanesulfonyl chloride → HCID 131732432, compound

HRID 1846326Notes

Reaction equation

HRID 1846326 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:22](=[O:23])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=[C:14]2[C:24]2[CH:29]=[C:28]([CH3:30])[C:27]([O:31][CH2:32][CH2:33][OH:34])=[C:26]([CH3:35])[CH:25]=2)=[CH:9][CH:8]=1>C(Cl)Cl>[CH3:1][S:2]([O:34][CH2:33][CH2:32][O:31][C:27]1[C:26]([CH3:35])=[CH:25][C:24]([C:14]2[N:13]([C:10]3[CH:11]=[CH:12][C:7]([N:6]([S:2]([CH3:1])(=[O:4])=[O:3])[S:2]([CH3:1])(=[O:4])=[O:3])=[CH:8][CH:9]=3)[C:22](=[O:23])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)=[CH:29][C:28]=1[CH3:30])(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 46841271HCID 46841271, compound

Product 1

HCID 131732432HCID 131732432, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TEA (0.24 mL, 1.70 mmol) followed by methanesulfonyl chloride (0.13 mL, 1.70 mmol) were added to a solution of 3-(4-aminophenyl)-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)quinazolin-4(3H)-one (0.230 g, 0.57 mmol) in CH2Cl2 (10 mL). After stirring for 6 hours at room temperature, the mixture was concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 2% to 8% MeOH in CH2Cl2, afforded 2-(2,6-dimethyl-4-(3-(4-(N-(methylsulfonyl)methylsulfonamido) phenyl)-4-oxo-3,4-dihydroquinazolin-2-yl)phenoxy)ethyl methanesulfonate (0.280 g, 77%).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customPurification by flash chromatography on silica gel
  3. washeluting with 2% to 8% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-8f8861315d0444f186aabc8877e14c8c
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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