Thiophenol → HCID 57788015, compound

HRID 249984Notes

Reaction equation

HRID 249984 reaction equation
[CH:1]([NH:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][S:22]([CH3:37])(=[N:24]S(C3C=CC([N+]([O-])=O)=CC=3)(=O)=O)=[O:23])=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]=[CH:7][N:6]=1)([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].C1(S)C=CC=CC=1>C(#N)C.O.C(Cl)Cl>[CH:1]([NH:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][S:22]([CH3:37])(=[NH:24])=[O:23])=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]=[CH:7][N:6]=1)([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 7969ThiophenolHCID 10796Cesium carbonateHCID 57787964HCID 57787964, compound

Product 1

HCID 57788015HCID 57788015, compoundYield 51%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

(RS)-S-(4-{[4-(Isopropylamino)-6-methoxyquinazolin-7-yl]oxy}butyl)-S-methyl-N-[(4-nitrophenyl)sulphonyl]sulphoximide (267 mg, 0.48 mmol) is dissolved in acetonitrile (7 ml), treated with caesium carbonate (266 mg, 0.82 mmol) and thiophenol (86 mg, 0.77 mmol) and stirred at room temperature for 20 hours. The reaction batch is diluted with water and methylene chloride. The organic phase is separated off and dried over sodium sulphate. The desired product is obtained after removal of the solvent and preparative HPLC in 51% yield (126 mg).

Workup

  1. customThe organic phase is separated off
  2. dry with materialdried over sodium sulphate

Sources & evidence

ORD record
ord-4f0137e470504439a87b09201c10be2a
Source dataset
uspto-grants-2011_01
Patent number
US07863283B2

Reaction notes

Loading…