Hexane → (RS)-S-Ethyl-S-[3-({[4-(isopropylamino)-6-methoxyquinazolin-7-yl]oxy}-methyl)phenyl]sulphoximide

HRID 249979Notes

Reaction equation

HRID 249979 reaction equation
C(OC([N:6]=[S:7]([CH2:33][CH3:34])([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][O:16][C:17]2[CH:26]=[C:25]3[C:20]([C:21]([NH:27][CH:28]([CH3:30])[CH3:29])=[N:22][CH:23]=[N:24]3)=[CH:19][C:18]=2[O:31][CH3:32])[CH:10]=1)=[O:8])=O)C.CCCCCC.C(OCC)(=O)C.CO>CO.ClCCl.CO>[CH2:33]([S:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][O:16][C:17]2[CH:26]=[C:25]3[C:20]([C:21]([NH:27][CH:28]([CH3:29])[CH3:30])=[N:22][CH:23]=[N:24]3)=[CH:19][C:18]=2[O:31][CH3:32])[CH:10]=1)(=[NH:6])=[O:8])[CH3:34]

Participants

6

Reactant 3

HCID 8058HexaneHCID 21584119Ethylacetate methanolHCID 57788042(RS)-N-(Ethoxycarbonyl)-S-ethyl-S-[3-({[4-(isopropylamino)-6-methoxy-quinazolin-7-yl]oxy}methyl)phenyl]sulphoximide

Product 1

HCID 44129662(RS)-S-Ethyl-S-[3-({[4-(isopropylamino)-6-methoxyquinazolin-7-yl]oxy}-methyl)phenyl]sulphoximideYield 82%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 21226129Dichloromethane methanolSolvent

Procedure

According to GWP 6, the conversion of (RS)-N-(ethoxycarbonyl)-S-ethyl-S-[3-({[4-(isopropylamino)-6-methoxyquinazolin-7-yl]oxy}methyl)phenyl]sulphoximide (64 mg, 0.13 mmol) and chromatographic purification (silica gel, hexane, ethyl acetate/methanol: 0→10% methanol, followed by dichloromethane/methanol: 0→15% methanol) gives the desired product in 82% yield (45 mg).

Sources & evidence

ORD record
ord-f77acfc1ef0b4e3dbad2fac62c7f3a21
Source dataset
uspto-grants-2011_01
Patent number
US07863283B2

Reaction notes

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