Hydrogen Peroxide → HCID 89647760, compound

HRID 2281013Notes

Reaction equation

HRID 2281013 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:13][C@@H:14]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[CH:31]=2)[CH2:15][N:16]([CH3:29])S(C2C=CC([N+]([O-])=O)=CC=2)(=O)=O)=[C:7]2[C:12]=1[N:11]=[CH:10][N:9]=[CH:8]2)#[N:2].[OH-:37].[Na+].OO>CS(C)=O>[F:36][C:32]1[CH:31]=[C:30]([C@H:14]([NH:13][C:6]2[CH:5]=[CH:4][C:3]([C:1]([NH2:2])=[O:37])=[C:12]3[C:7]=2[CH:8]=[N:9][CH:10]=[N:11]3)[CH2:15][NH:16][CH3:29])[CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 89647984HCID 89647984, compound

Product 1

HCID 89647760HCID 89647760, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
40 °C

Procedure

To a stirred solution of N—[(S)-2-(8-Cyano-quinazolin-5-ylamino)-2-(3-fluoro-phenyl)-ethyl]-N-methyl-4-nitro-benzenesulfonamide (120.00 mg; 0.24 mmol; 1.00 eq.) in DMSO (8 ml) was added aqueous 2.0M NaOH (0.59 ml; 1.18 mmol; 5.00 eq.) and aqueous 35% hydrogen peroxide (0.14 ml; 1.42 mmol; 6.00 eq.) and continued stirring at 40° C. overnight. The crude product was purified by prep-HPLC to yield the desired product, which was then added of acetonitrile (2 ml), thiophenol (0.1 ml), CsCO3 (200 mg), and stirred at 40° C. overnight. The crude was purified by prepHPLC to afford the title product. LC-MS (M+H=434, obsd.=434).

Workup

  1. customThe crude product was purified by prep-HPLC

Sources & evidence

ORD record
ord-538f2ef0d2cd4156b796429224965318
Source dataset
uspto-grants-2015_09
Patent number
US09139568B2

Reaction notes

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