Hydrochloric Acid → 2-((2-Chloro-5-cyano-3-(4-(2,2-difluoroethyl)piperazin-1-yl)phenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile, hydrochloride

HRID 1430808Notes

Reaction equation

HRID 1430808 reaction equation
[Cl:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH:15]([F:17])[F:16])[CH2:10][CH2:9]2)=[CH:6][C:5]([C:18]#[N:19])=[CH:4][C:3]=1[NH:20][C:21]1[N:26]=[C:25]([NH:27][CH:28]2[CH2:30][CH2:29]2)[C:24]2=[N:31][CH:32]=[C:33]([C:34]#[N:35])[N:23]2[N:22]=1.Cl>C(#N)C.O>[ClH:1].[Cl:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH:15]([F:17])[F:16])[CH2:10][CH2:9]2)=[CH:6][C:5]([C:18]#[N:19])=[CH:4][C:3]=1[NH:20][C:21]1[N:26]=[C:25]([NH:27][CH:28]2[CH2:29][CH2:30]2)[C:24]2=[N:31][CH:32]=[C:33]([C:34]#[N:35])[N:23]2[N:22]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 729483172-((2-Chloro-5-cyano-3-(4-(2,2-difluoroethyl)piperazin-1-yl)phenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile

Product 1

HCID 1317323752-((2-Chloro-5-cyano-3-(4-(2,2-difluoroethyl)piperazin-1-yl)phenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile, hydrochlorideYield 199.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To the stirred solution of ((2-chloro-5-cyano-3-(4-(2,2-difluoroethyl)piperazin-1-yl)phenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (0.045 g, 0.090 mmol) in dry acetonitrile (2.0 mL), water (4.0 mL) was added 1N HCl (90 μL, 0.090 mmol) at room temperature. The reaction mixture stirred at room temperature for 10 minutes. The reaction mixture converted in to clear solution. This mixture was freeze dried and lyophilized to afford 2-((2-chloro-5-cyano-3-(4-(2,2-difluoroethyl)piperazin-1-yl)phenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile, hydrochloride (48.0 mg) as an off-white solid.

Workup

  1. customdried

Sources & evidence

ORD record
ord-98a600f1f30c470d8e512da6a62696c9
Source dataset
uspto-grants-2015_01
Patent number
US08940736B2

Reaction notes

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