Picolinoyl Chloride Hydrochloride → 4-[2-({4-[[3-(4-Chlorophenyl)propyl](methyl)amino]-6-[4-(2-pyridinylcarbonyl)-1-piperazinyl]-1,3,5-triazin-2-yl}amino)ethyl]phenol

HRID 496022

Reaction equation

HRID 496022 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][N:11]([CH3:34])[C:12]2[N:17]=[C:16]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[N:15]=[C:14]([NH:24][CH2:25][CH2:26][C:27]3[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=3)[N:13]=2)=[CH:4][CH:3]=1.Cl.[N:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[C:42](Cl)=[O:43]>C(Cl)Cl.CCOC(C)=O.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][N:11]([CH3:34])[C:12]2[N:17]=[C:16]([N:18]3[CH2:19][CH2:20][N:21]([C:42]([C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][N:36]=4)=[O:43])[CH2:22][CH2:23]3)[N:15]=[C:14]([NH:24][CH2:25][CH2:26][C:27]3[CH:28]=[CH:29][C:30]([OH:33])=[CH:31][CH:32]=3)[N:13]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 135033Picolinoyl Chloride HydrochlorideHCID 102995574-(2-{[4-[[3-(4-Chlorophenyl)propyl](methyl)amino]-6-(1-piperazinyl)-1,3,5-triazin-2-yl]amino}ethyl)phenol

Product 1

HCID 101450604-[2-({4-[[3-(4-Chlorophenyl)propyl](methyl)amino]-6-[4-(2-pyridinylcarbonyl)-1-piperazinyl]-1,3,5-triazin-2-yl}amino)ethyl]phenolYield 46%

Reagents, catalysts & solvents 1

HCID 21901258Dichloromethane ethyl acetate methanolSolvent

Procedure

The title compound was prepared in 46% yield via the procedure outlined for Example 3 using 4-(2-{[4-[[3-(4-chlorophenyl)propyl](methyl)amino]-6-(1-piperazinyl)-1,3,5-triazin-2-yl]amino}ethyl)phenol and picolinoyl chloride hydrochloride to give a white glass: 1H NMR (CDCl3, 300 MHz) δ 8.65 (bs, 1H), 7.83 (t, 1H, J=7.5), 7.72 (d, 1H, J=7.5), 7.40 (t, 1H, J=5.7), 7.24-7.21 (m, 2H), 7.12-7.04 (m, 4H), 6.73 (d, 2H, J=8.1), 3.96-3.78 (m, 4H), 3.75-3.55 (m, 6H), 3.10 (s, 3H), 2.80 (t, 2H, J=6.6), 2.65-2.60 (m, 2H), 1.95-1.89 (m, 2H); low resolution MS (ES+) m/e 588 (MH+); TLC (CH2Cl2/EtOAc/MeOH (5:5:1)): Rf=0.62.

Workup

  1. customto give a white glass

Sources & evidence

ORD record
ord-3a131a92e5cf41879452c243cafb2e79
Source dataset
uspto-grants-2005_09
Patent number
US06943162B2

Linked notes

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