Ethanol → (RS)-S-[3-({[4-(Isopropylamino)-6-methoxyquinazolin-7-yl]oxy}methyl)phenyl]-S-methylsulphoximide

HRID 249974Notes

Reaction equation

C(OC([N:6]=[S:7]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][O:17][C:18]2[CH:27]=[C:26]3[C:21]([C:22]([NH:28][CH:29]([CH3:31])[CH3:30])=[N:23][CH:24]=[N:25]3)=[CH:20][C:19]=2[O:32][CH3:33])[CH:11]=1)([CH3:9])=[O:8])=O)C.C(O)C.[O-]CC.[Na+]>ClCCl.CO>[CH:29]([NH:28][C:22]1[C:21]2[C:26](=[CH:27][C:18]([O:17][CH2:16][C:12]3[CH:11]=[C:10]([S:7]([CH3:9])(=[NH:6])=[O:8])[CH:15]=[CH:14][CH:13]=3)=[C:19]([O:32][CH3:33])[CH:20]=2)[N:25]=[CH:24][N:23]=1)([CH3:30])[CH3:31]

Participants

Conditions

Temperature: 80 °C

Procedure

(RS)-N-(Ethoxycarbonyl)-S-[3-({[4-(isopropylamino)-6-methoxyquinazolin-7-yl]oxy}-methyl)phenyl]-S-methylsulphoximide (105 mg, 0.22 mmol) is introduced into 2.5 ml of ethanol. 1.0 ml of a 1-molar ethanolic sodium ethoxide solution is added and the mixture is heated to 80° C., until starting material is no longer present according to TLC checking (eluent dichloromethane/methanol 10:1). The reaction solution is concentrated in vacuo, and the residue is taken up in ethyl acetate and washed with saturated sodium carbonate solution. The organic phase is dried over sodium sulphate and concentrated. The crude product is purified by preparative HPLC and the desired product is obtained in 36% yield (32 mg).

Workup

concentrationThe reaction solution is concentrated in vacuo
washwashed with saturated sodium carbonate solution
dry with materialThe organic phase is dried over sodium sulphate
concentrationconcentrated
customThe crude product is purified by preparative HPLC

Sources & evidence

ORD record: ord-63ea4ec651fd49ed9c78ba2da63f3ba8
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863283B2

Reaction notes

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