Ethyl Acetate → HCID 44197698, compound

HRID 249956Notes

Reaction equation

HRID 249956 reaction equation
[CH:1]1([NH:4][C:5]2[C:14]3[C:9](=[CH:10][C:11]([NH:15][CH2:16][C:17]4[CH:18]=[C:19]([S:23]([CH3:31])(=[N:25]C(OCC)=O)=[O:24])[CH:20]=[CH:21][CH:22]=4)=[CH:12][CH:13]=3)[N:8]=[CH:7][N:6]=2)[CH2:3][CH2:2]1.CCCCCC.C(OCC)(=O)C.C(OCC)(=O)C.ClCCl.CO>CO>[CH:1]1([NH:4][C:5]2[C:14]3[C:9](=[CH:10][C:11]([NH:15][CH2:16][C:17]4[CH:18]=[C:19]([S:23]([CH3:31])(=[NH:25])=[O:24])[CH:20]=[CH:21][CH:22]=4)=[CH:12][CH:13]=3)[N:8]=[CH:7][N:6]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 21226129Dichloromethane methanolHCID 21226206Ethyl acetate hexaneHCID 57788030HCID 57788030, compound

Product 1

HCID 44197698HCID 44197698, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

According to GWP 6, conversion of (RS)-S-[3-({[4-(cyclopropylamino)quinazolin-7-yl]amino}methyl)phenyl]-N-(ethoxycarbonyl)-S-methylsulphoximide (58 mg, 0.13 mmol) and chromatographic purification (silica gel, n-hexane/ethyl acetate: 0→100% ethyl acetate, followed by dichloromethane/methanol: 0→25% methanol) gives the desired product in 74% yield (36 mg).

Sources & evidence

ORD record
ord-7b91d42cc94e4d7b93469ac883b9583c
Source dataset
uspto-grants-2011_01
Patent number
US07863283B2

Reaction notes

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