Hydrogen Peroxide → HCID 78135264, compound

HRID 2281012Notes

Reaction equation

HRID 2281012 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:13][CH:14]2[CH:18]([C:19]3[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=3)[CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15]2)=[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:27][C:26]([F:29])([F:28])[O:25][C:22]1[CH:21]=[CH:20][C:19]([CH:18]2[CH2:17][NH:16][CH2:15][CH:14]2[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)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 89647507HCID 89647507, compound

Product 1

HCID 78135264HCID 78135264, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Tert-butyl 3-(8-Cyano-quinazolin-5-ylamino)-4-(4-trifluoromethoxy-phenyl)-pyrrolidine-1-carboxylate (100.00 mg; 0.20 mmol; 1.00 eq.) was stirred with aqueous 2.0M NaOH (1 ml; 2.00 mmol; 10.00 eq.) and aqueous 35% H2O2 (0.19 ml; 2.00 mmol; 10.00 eq.) in DMSO (8 ml) at 40° C. overnight. The crude was purified by pre-HPLC to yield the title compound (58 mg, 56.0%).

Workup

  1. customThe crude was purified by pre-HPLC

Sources & evidence

ORD record
ord-2db0bc22ac904e448a7e1049a1e6b5c8
Source dataset
uspto-grants-2015_09
Patent number
US09139568B2

Reaction notes

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