Sodium ethoxide → HCID 57787998, compound
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([S:24]([CH3:32])(=[N:26]C(OCC)=O)=[O:25])[CH:19]=1)[N:12]=[CH:11][N:10]=[C:9]2[NH:33][C:34]1[S:35][CH:36]=[CH:37][N:38]=1)=[O:5])[CH3:2].[O-]CC.[Na+]>>[CH3:32][S:24]([C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=1)[CH2:17][O:16][C:15]1[CH:14]=[C:13]2[C:8]([C:9]([NH:33][C:34]3[S:35][CH:36]=[CH:37][N:38]=3)=[N:10][CH:11]=[N:12]2)=[CH:7][C:6]=1[C:4]([O:3][CH2:1][CH3:2])=[O:5])(=[NH:26])=[O:25]Participants
3
Procedure
According to GWP 6, ethyl-7-({(RS)-3-[N-(ethoxycarbonyl)-S-methyl-sulphonimidoyl]-benzyl}oxy)-4-(thiazol-2-ylamino)quinazoline-6-carboxylate (175 mg, 0.182 mmol) is reacted at 80° C. for 2 hours with sodium ethoxide (55 mg, 0.8 mmol). After cooling, the reaction mixture is concentrated to dryness. The residue is taken up in ethyl acetate and water. The organic phase is separated off, dried over sodium sulphate and subsequently concentrated. The desired product is obtained after chromatographic purification (silica gel, dichloromethane/methanol: 9/1) in 42% yield (39 mg).
Workup
- temperatureAfter cooling
- concentrationthe reaction mixture is concentrated to dryness