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 921639Notes

Reaction equation

HRID 921639 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 0.2%

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-9ef97d1e8f8b495b815e2127265b9f82
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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