Potassium Carbonate → 2-(4-(2-chloro-5-cyano-3-((7-cyano-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazin-2-yl)amino)phenyl)-3-oxopiperazin-1-yl)-N-methylacetamide

HRID 921878Notes

Reaction equation

HRID 921878 reaction equation
[Cl:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][C:9]2=[O:14])=[CH:6][C:5]([C:15]#[N:16])=[CH:4][C:3]=1[NH:17][C:18]1[N:23]=[C:22]([NH:24][CH:25]2[CH2:27][CH2:26]2)[C:21]2=[N:28][CH:29]=[C:30]([C:31]#[N:32])[N:20]2[N:19]=1.Br[CH2:34][C:35]([NH:37][CH3:38])=[O:36].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[C:3]([NH:17][C:18]2[N:23]=[C:22]([NH:24][CH:25]3[CH2:27][CH2:26]3)[C:21]3=[N:28][CH:29]=[C:30]([C:31]#[N:32])[N:20]3[N:19]=2)=[CH:4][C:5]([C:15]#[N:16])=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([CH2:34][C:35]([NH:37][CH3:38])=[O:36])[CH2:10][C:9]1=[O:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 154907452-Bromo-N-methylacetamideHCID 89922950HCID 89922950, compound

Product 1

HCID 899228262-(4-(2-chloro-5-cyano-3-((7-cyano-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazin-2-yl)amino)phenyl)-3-oxopiperazin-1-yl)-N-methylacetamideYield 25.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To solution of 2-((2-chloro-5-cyano-3-(2-oxopiperazin-1-yl)phenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (Example 628)(20 mg, 0.045 mmol) in DMF (0.5 mL) was added 2-bromo-N-methylacetamide (13.54 mg, 0.089 mmol) followed by K2CO3 (73.9 mg, 0.535 mmol) at room temperature and stirred at room temperature for 1 h, LC-MS indicated completion. Purification via preparative HPLC gave the title compound as a yellow solid (5.9 mg).

Workup

  1. customPurification via preparative HPLC

Sources & evidence

ORD record
ord-e6f208491eed46eaa0be1eb79ca0ec73
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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