(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

HRID 2296880Notes

Reaction equation

HRID 2296880 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([OH:10])=O)=[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:5]([CH3:17])=[CH:4][N:3]=1.[F:18][C:19]([F:38])([F:37])[C:20]1[CH:21]=[C:22]([CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=1)[CH2:23][NH:24][CH2:25][C@H:26]([CH3:29])[CH2:27][OH:28].CS(OCC1C=C(C(F)(F)F)C=C(C(F)(F)F)C=1)(=O)=O.NC[C@H](C)CO.ClC1C(C(O)=O)=C(C2C=CC=CC=2)C=CN=1.FC(F)(F)C1C=C(C=C(C(F)(F)F)C=1)CNCCO>C1COCC1>[F:18][C:19]([F:37])([F:38])[C:20]1[CH:21]=[C:22]([CH:30]=[C:31]([C:33]([F:34])([F:36])[F:35])[CH:32]=1)[CH2:23][N:24]([CH2:25][C@H:26]([CH3:29])[CH2:27][OH:28])[C:8]([C:7]1[C:2]([Cl:1])=[N:3][CH:4]=[C:5]([CH3:17])[C:6]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10]

Participants

8

Reactant 6

HCID 640990(2S)-3-amino-2-methylpropan-1-olHCID 183872502-Chloro-5-methyl-4-phenyl-3-pyridinecarboxylic acidHCID 18387265[3,5-Bis(trifluoromethyl)phenyl]methyl methanesulfonateHCID 183873122-Chloro-4-phenylnicotinic acidHCID 22248766N-[3,5-bis(trifluoromethyl)benzyl]-N-(2-hydroxyethyl)amineHCID 53883864N-[3,5-bis(trifluoromethyl)benzyl]-N-[(s)-3-hydroxy-2-methylpropyl]amine

Product 1

HCID 54247085N-(3,5-Bis(trifluoromethyl)benzyl]-2-chloro-N-((S)-3-hydroxy-2-methylpropyl]-5-methyl-4-phenyl-3-pyridinecarboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  1. customthis was prepared
  2. customto obtain the entitled compound as a colorless oily substance

Sources & evidence

ORD record
ord-fae3163fc0df481a99aa782387e3dfab
Source dataset
uspto-grants-2002_12
Patent number
US06489315B1

Reaction notes

Loading…