Hydrogen Peroxide → HCID 89442652, compound

HRID 2284051Notes

Reaction equation

HRID 2284051 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([N:13]2[CH:17]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[C:20]([C:25]([F:28])([F:27])[F:26])[CH:19]=3)[N:15]=[C:14]2[CH:29]2[CH2:34][CH2:33][N:32]([C:35]3[C:40]([C:41]#[N:42])=[C:39]([NH2:43])[N:38]=[CH:37][N:36]=3)[CH2:31][CH2:30]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH:44]O>CS(C)=O>[NH2:43][C:39]1[N:38]=[CH:37][N:36]=[C:35]([N:32]2[CH2:31][CH2:30][CH:29]([C:14]3[N:13]([CH:10]4[CH2:11][CH2:12][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9]4)[CH:17]=[C:16]([C:18]4[CH:23]=[CH:22][C:21]([F:24])=[C:20]([C:25]([F:28])([F:27])[F:26])[CH:19]=4)[N:15]=3)[CH2:34][CH2:33]2)[C:40]=1[C:41](=[O:44])[NH2:42]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 89442643HCID 89442643, compound

Product 1

HCID 89442652HCID 89442652, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A reaction mixture of 3-[2-[1-(6-amino-5-cyano-pyrimidin-4-yl)-piperidin-4-yl]-4-(4-fluoro-3-trifluoromethyl-phenyl)-imidazol-1-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester (100.00 mg; 0.17 mmol; 1.00 eq.) and 2.0N NaOHaq (0.83 ml; 1.66 mmol; 10.00 eq.), in DMSO 8 ml was stirred at RT for 5 mins, added H2O2 (0.16 ml; 1.66 mmol; 10.00 eq.) stirred at RT for 2 hr. Purified the product by HPLC (basic), collected title compound 45 mg, yield 43%.

Workup

  1. customPurified the product by HPLC (basic)

Sources & evidence

ORD record
ord-f085d097feff4b148156f053a5218e4c
Source dataset
uspto-grants-2015_09
Patent number
US09145392B2

Reaction notes

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