3-(3,5-Bis(trifluoromethyl)benzylamino)propanol → N-[3,5-Bis(trifluoromethyl)benzyl]-2-chloro-N-(3-hydroxypropyl)-6-methyl-4-phenyl-3-pyridinecarboxamide
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)[CH:5]=[C:4]([CH3:17])[N:3]=1.[F:18][C:19]([F:37])([F:36])[C:20]1[CH:21]=[C:22]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[CH2:23][NH:24][CH2:25][CH2:26][CH2:27][OH:28].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>>[F:18][C:19]([F:36])([F:37])[C:20]1[CH:21]=[C:22]([CH:29]=[C:30]([C:32]([F:33])([F:35])[F:34])[CH:31]=1)[CH2:23][N:24]([CH2:25][CH2:26][CH2:27][OH:28])[C:8]([C:7]1[C:2]([Cl:1])=[N:3][C:4]([CH3:17])=[CH:5][C:6]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10]Participants
5
Reactant 4
Product 1
Procedure
The same process as in Step 2 in Reference Example 12 was repeated, except that 2-chloro-6-methyl-4-phenyl-3-pyridinecarboxylic acid was reacted with N-[3,5-bis(trifluoromethyl)benzyl]-N-(3-hydroxypropyl)amine 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 pale-yellow, oily substance. NMR(200 MHz, CDCl3) ppm: 1.15-1.65(2H,m), 2.59(3H,s), 2.75-3.20(2H,m), 4.06(1H×2/5,d,J=15.4 Hz), 4.31(1H×2/5,d,J=15.4 Hz), 4.65(1H×3/5,d,J=15.2 Hz), 4.74(1H×3/5,d,J=15.2 Hz), 7.16(1H,s), 7.20-7.60(5H,m), 7.72(2H,s), 7.78(1H,s)
Workup
- customto obtain the entitled compound as a pale-yellow, oily substance
Sources & evidence
- ORD record
- ord-94368747ed8c4efb8447a587d1b39dcc
- Source dataset
- uspto-grants-2000_11
- Patent number
- US06147071
Reaction notes
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