Thiophenol → HCID 57788046, compound

HRID 249986Notes

Reaction equation

HRID 249986 reaction equation
[CH:1]([NH:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:20][CH2:21][CH2:22][CH2:23][S:24]([CH3:39])(=[N:26]S(C3C=CC([N+]([O-])=O)=CC=3)(=O)=O)=[O:25])=[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O: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:20][CH2:21][CH2:22][CH2:23][S:24]([CH3:39])(=[NH:26])=[O:25])=[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:13]=2)[N:8]=[CH:7][N:6]=1)([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 7969ThiophenolHCID 10796Cesium carbonateHCID 57788011HCID 57788011, compound

Product 1

HCID 57788046HCID 57788046, compoundYield 45%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

Ethyl 4-(isopropylamino)-7-[(RS)-3-{S-methyl -N-[(4-nitrophenyl)sulphonyl]-sulphonimidoyl}propoxy]quinazoline-6-carboxylate (270 mg, 0.47 mmol) is dissolved in acetonitrile (7 ml), treated with caesium carbonate (276 mg, 0.85 mmol) and thiophenol (90 mg, 0.82 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, preparative HPLC and subsequent repeated trituration of the residue in 45% yield (83 mg).

Workup

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

Sources & evidence

ORD record
ord-04dc0bbacafe45588abd4d14c495867d
Source dataset
uspto-grants-2011_01
Patent number
US07863283B2

Reaction notes

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