Diisopropylethylamine → N-[2-(4-{[4-Chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)ethyl]-N-methylguanidine

HRID 474574Notes

Reaction equation

HRID 474574 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13]C(CCNC)=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:19]([F:22])([F:21])[F:20].[CH3:23]CN(C(C)C)C(C)C.[N:32]1([C:37](=[NH:39])[NH2:38])[CH:36]=[CH:35][CH:34]=N1>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:34]([CH2:35][CH2:36][N:32]([CH3:23])[C:37]([NH2:38])=[NH:39])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:19]([F:20])([F:21])[F:22]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2734673PraxadineHCID 67774711HCID 67774711, compound

Product 1

HCID 67775141N-[2-(4-{[4-Chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)ethyl]-N-methylguanidineYield 93.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)-N-methylethanamine (300 mg, 0.910 mmol) and DIPEA (0.477 mL, 2.73 mmol) in DMF (5 mL) was added 1H-pyrazole-1-carboximidamide (150 mg, 1.365 mmol). The reaction mixture was stirred at room temperature overnight. Purification via a reverse phase Biotage then afforded the title compound (315 mg, 93% yield) as a white powder. LCMS: rt=2.88 min, [M+H+]=371.9

Workup

  1. customPurification via a reverse phase Biotage

Sources & evidence

ORD record
ord-dcbebbf65d684fb79df2fd39df4f4f1d
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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