Trifluoromethanesulfonic anhydride → 4-(4-Isopropyl-phenyl)-6-prop-2-ynyloxy-1-[(E)-2-(2,4,6-trimethyl-phenyl)-vinyl]-1H-quinazolin-2-one

HRID 641861Notes

Reaction equation

HRID 641861 reaction equation
O[CH:2]([C:28]1[C:33]([CH3:34])=[CH:32][C:31]([CH3:35])=[CH:30][C:29]=1[CH3:36])[CH2:3][N:4]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH2:15][C:16]#[CH:17])=[CH:11][CH:12]=2)[C:7]([C:18]2[CH:23]=[CH:22][C:21]([CH:24]([CH3:26])[CH3:25])=[CH:20][CH:19]=2)=[N:6][C:5]1=[O:27].FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O>ClCCCl>[CH:24]([C:21]1[CH:22]=[CH:23][C:18]([C:7]2[C:8]3[C:13](=[CH:12][CH:11]=[C:10]([O:14][CH2:15][C:16]#[CH:17])[CH:9]=3)[N:4](/[CH:3]=[CH:2]/[C:28]3[C:29]([CH3:36])=[CH:30][C:31]([CH3:35])=[CH:32][C:33]=3[CH3:34])[C:5](=[O:27])[N:6]=2)=[CH:19][CH:20]=1)([CH3:25])[CH3:26]

Participants

4

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 592591561-[2-hydroxy-2-(2,4,6-trimethyl-phenyl)-ethyl]-4-(4-isopropyl-phenyl)-6-prop-2-ynyloxy-1H-quinazolin-2-one

Product 1

HCID 592590904-(4-Isopropyl-phenyl)-6-prop-2-ynyloxy-1-[(E)-2-(2,4,6-trimethyl-phenyl)-vinyl]-1H-quinazolin-2-one

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 50 mg (0.104 mmol) 1-[2-hydroxy-2-(2,4,6-trimethyl-phenyl)-ethyl]-4-(4-isopropyl-phenyl)-6-prop-2-ynyloxy-1H-quinazolin-2-one and 34.3 μl (0.208 mmol) trifluoromethane sulphonic anhydride in 0.5 ml 1,2 dichloroethane is heated to 80° C. for 15 min. Extraction with dichloromethane/aqueous NaHCO3 followed by preparative reversed phase HPLC yielded the title compound.

Workup

  1. extractionExtraction with dichloromethane/aqueous NaHCO3

Sources & evidence

ORD record
ord-e1b605e877824aeea95fd131d48993be
Source dataset
uspto-grants-2010_04
Patent number
US07696216B2

Reaction notes

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