Ethyl chloroformate → N-[(S)-2-(3,4-Dichlorophenyl)-4-[4-[(S)-2-methylsulfinylphenyl]-1-piperidinyl]butyl]-N-ethyl-3-cyano-1-naphthamide
Reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:13]([OH:15])=O)[C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)#[N:2].[Cl:16][C:17]1[CH:18]=[C:19]([C@H:24]([CH2:29][CH2:30][N:31]2[CH2:36][CH2:35][CH:34]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[S@:43]([CH3:45])=[O:44])[CH2:33][CH2:32]2)[CH2:25][NH:26][CH2:27][CH3:28])[CH:20]=[CH:21][C:22]=1[Cl:23].ClC1C=C([C@H](CCN2CCC(C3C=CC=CC=3[S@](C)=O)CC2)CNC)C=CC=1Cl.ClC(OCC)=O>>[Cl:16][C:17]1[CH:18]=[C:19]([C@H:24]([CH2:29][CH2:30][N:31]2[CH2:32][CH2:33][CH:34]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[S@:43]([CH3:45])=[O:44])[CH2:35][CH2:36]2)[CH2:25][N:26]([CH2:27][CH3:28])[C:13]([C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:12]=[C:3]([C:1]#[N:2])[CH:4]=2)=[O:15])[CH:20]=[CH:21][C:22]=1[Cl:23]Participants
5
Reactant 4
Product 1
Procedure
Using standard acylation conditions, 3-cyano-1-naphthoic acid (0.118 g) was converted to the acid chloride and reacted with N-[(S)-2-(3,4-dichlorophenyl)-4-[4-[(S)-2-methylsulfinylphenyl]-1-piperidinyl]butyl]-N-ethylamine (0.336 g) (prepared according to methods described for N-[(S)-2-(3,4-dichlorophenyl)-4-[4-[(S)-2-methylsulfinylphenyl]-1-piperidinyl]butyl]-N-methylamine, except ethyl chloroformate was used in place of acetyl chloride for the amine acylation prior to amide reduction). mp 115-118° C. (dec); 1H NMR (300 MHz, DMSO-d6) δ 8.65 (d), 8.10 (m), 7.95-7.15 (m), 6.50 (m), 3.60 (s), 3.25-2.95 (m), 2.95-2.40 (m), 2.40-1.70 (m), 1.35 (m), 0.9 (m); MS APCI, m/z=646 (M+).
Workup
- customprepared
Sources & evidence
- ORD record
- ord-fbb6be677d8d4c51a9d55fc88f532c4c
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06365602B1
Reaction notes
Loading…