Hydrogen Peroxide → 4-amino-6-(4-(1-(2-(azetidin-1-yl)ethyl)-4-(4-fluoro-3-methoxyphenyl)-1H-imidazol-2-yl)piperidin-1-yl)pyrimidine-5-carboxamide

HRID 2284043Notes

Reaction equation

HRID 2284043 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]3[N:17]([CH2:30][CH2:31][N:32]4[CH2:35][CH2:34][CH2:33]4)[CH:18]=[C:19]([C:21]4[CH:26]=[CH:25][C:24]([F:27])=[C:23]([O:28][CH3:29])[CH:22]=4)[N:20]=3)[CH2:12][CH2:11]2)[N:5]=[CH:4][N:3]=1.[OH:36]O.[OH-].[Na+]>CS(C)=O>[NH2:1][C:2]1[C:7]([C:8]([NH2:9])=[O:36])=[C:6]([N:10]2[CH2:11][CH2:12][CH:13]([C:16]3[N:17]([CH2:30][CH2:31][N:32]4[CH2:33][CH2:34][CH2:35]4)[CH:18]=[C:19]([C:21]4[CH:26]=[CH:25][C:24]([F:27])=[C:23]([O:28][CH3:29])[CH:22]=4)[N:20]=3)[CH2:14][CH2:15]2)[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 89442607HCID 89442607, compound

Product 1

HCID 894426794-amino-6-(4-(1-(2-(azetidin-1-yl)ethyl)-4-(4-fluoro-3-methoxyphenyl)-1H-imidazol-2-yl)piperidin-1-yl)pyrimidine-5-carboxamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A reaction mixture of 4-Amino-6-{4-[1-(2-azetidin-1-yl-ethyl)-4-(4-fluoro-3-methoxy-phenyl)-1H-imidazol-2-yl]-piperidin-1-yl}-pyrimidine-5-carbonitrile (100.00 mg; 0.21 mmol; 1.00 eq.), DMSO 8 ml was stirred at RT added H2O2 (0.20 ml; 2.10 mmol; 10.00 eq.) and 2.0M NaOH.2.0MNaOH aq (1.05 ml; 2.10 mmol; 10.00 eq.), stirred at RT for 2 hr, got desired as major detected by lc-ms, purified the product by prep HPLC (basic), title compound 66 mg, 63%. LC-MS (M+1=495, obsd.=495).

Workup

  1. stirring2.0MNaOH aq (1.05 ml; 2.10 mmol; 10.00 eq.), stirred at RT for 2 hr
  2. custompurified the product by prep HPLC (basic), title compound 66 mg, 63%

Sources & evidence

ORD record
ord-e3ac649441a344118c133ebe68f5c8e1
Source dataset
uspto-grants-2015_09
Patent number
US09145392B2

Reaction notes

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