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Chloro-N,N-dimethylformiminium chloride → N-((5-bromo-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)methylene)-N-methylmethanaminium chloride

HRID 1475955
Notes
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Reaction equation

HRID 1475955 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[CH:10]=[C:4]2[CH:3]=1.[Cl-].[Cl:20][CH:21]=[N+:22]([CH3:24])[CH3:23]>ClCCCl>[Cl-:20].[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=3)[C:10]([CH:21]=[N+:22]([CH3:24])[CH3:23])=[C:4]2[CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 679814685-Bromo-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridine

Product 1

HCID 68276032N-((5-bromo-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)methylene)-N-methylmethanaminium chloride

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a stirred suspension of 5-bromo-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridine (200 mg, 0.66 mmol) in 1,2-dichloroethane (6 mL) was added N-(Chloromethylene)-N-methylmethanaminium chloride (195 mg, 1.5 mmol). The mixture was stirred at 20° C. for 20 h then heated to 50° C. for 1 h at which time monitoring the reaction by LC indicated all starting material had converted to the title compound. The solids were collected by filtration and dried under reduced pressure to afford the title compound as a solid (260 mg, 100%). LCMS m/z 331.0, 333.0 (M-(CH3)2NH+H2O)+, ret. time=2.13 min.

Workup

  1. temperaturethen heated to 50° C. for 1 h at which time
  2. customthe reaction by LC

Sources & evidence

ORD record
ord-59fef1b24fe744e0b39ad8de87cd9c44
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09018395B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes