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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2296880Generated: October 31, 2026

(2S)-3-amino-2-methylpropan-1-ol → N-(3,5-Bis(trifluoromethyl)benzyl]-2-chloro-N-((S)-3-hydroxy-2-methylpropyl]-5-methyl-4-phenyl-3-pyridinecarboxamide

https://huagongshe.com/reaction/2296880

Reaction equation

Participants

RoleNameHCIDCharge
Reactant(2S)-3-amino-2-methylpropan-1-olHCID 640990—
Reactant2-Chloro-5-methyl-4-phenyl-3-pyridinecarboxylic acidHCID 18387250—
Reactant[3,5-Bis(trifluoromethyl)phenyl]methyl methanesulfonateHCID 18387265—
Reactant2-Chloro-4-phenylnicotinic acidHCID 18387312—
ReactantN-[3,5-bis(trifluoromethyl)benzyl]-N-(2-hydroxyethyl)amineHCID 22248766—
ReactantN-[3,5-bis(trifluoromethyl)benzyl]-N-[(s)-3-hydroxy-2-methylpropyl]amineHCID 53883864—
SolventTetrahydrofuranHCID 8028—
ProductN-(3,5-Bis(trifluoromethyl)benzyl]-2-chloro-N-((S)-3-hydroxy-2-methylpropyl]-5-methyl-4-phenyl-3-pyridinecarboxamideHCID 54247085—

Reaction Steps

The same process as in Step 2 in Reference Example 12 was repeated, except that 2-chloro-5-methyl-4-phenyl-3-pyridinecarboxylic acid was reacted with N-[3,5-bis(trifluoromethyl)benzyl]-N-[(S)-3-hydroxy-2-methylpropyl]amine [this was prepared by reacting 3,5-bis(trifluoromethyl)benzyl methanesulfonate with (S)-3-amino-2-methylpropanol in THF, and this is a colorless oily substance and was identified by NMR(200 MHz, CDCl3) ppm: 0.86(3H,d,J=6.8 Hz), 1.98(1H,m), 2.63(1H,dd,J=9.4,11.8 Hz), 2.70-2.90(3H,m), 3.56(1H,dd,J=8.6,10.6 Hz), 3.71(1H,ddd,J=1.4,4.0,10.6 Hz), 3.87(1H,d,J=13.8 Hz), 3.98(1H,d,J=13.8 Hz), 7.79(3H,s)] in place of reacting 2-chloro-4-phenyl-3-pyridinecarboxylic acid with N-[3,5-bis(trifluoromethyl)benzyl]-N-(2-hydroxyethyl)amine, to obtain the entitled compound as a colorless oily substance.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06489315B1
Source datasetuspto-grants-2002_12
ORD IDord-fae3163fc0df481a99aa782387e3dfab
Source noteuspto-grants-2002_12