Acetonitrile → HCID 11071460, compound

HRID 496026Notes

Reaction equation

HRID 496026 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]([CH2:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[CH3:9])[N:5]=[C:4]([NH:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)[N:3]=1.[OH:30][CH2:31][CH2:32][N:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1.CC#N.C(O)(C(F)(F)F)=O>O>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][CH2:11][CH2:10][N:8]([CH3:9])[C:6]2[N:7]=[C:2]([N:36]3[CH2:37][CH2:38][N:33]([CH2:32][CH2:31][OH:30])[CH2:34][CH2:35]3)[N:3]=[C:4]([NH:20][CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=3)[N:5]=2)=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 6422Trifluoroacetic acidHCID 76771-(2-Hydroxyethyl)piperazineHCID 10895309HCID 10895309, compound

Product 1

HCID 11071460HCID 11071460, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared in 91% yield via the procedure outlined for Example 14 using 4-[2-({4-chloro-6-[[3-(4-chlorophenyl)propyl](methyl)amino]-1,3,5-triazin-2-yl}amino)ethyl]phenol and 1-(2-hydoxyethyl)piperazine to give a white solid: 1H NMR (CDCl3, 400 MHz) δ 7.23 (d, 2H, J=8.0), 7.10 (d, 2H, J=8.0), 7.09 (d, 2H, J=8.0), 6.67 (d, 2H, J=8.0), 4.88(s, br, 1H), 3.80-3.55 (m, 9H), 3.05 (s, br, 3H), 2.77 (t, 2H, J=6.6), 2.57-2.48 (m, 8H), 1.86 (s,br, 2H); low-resolution MS (ES+) m/e 526 (MH+); RP-HPLC (Capcell Pak C-18 25 cm×4.6 mm; 0-95% CH3CN in H2O with 0.1% TFA buffer; 30 minutes; 1 mL/min) tr=11.20 min, 99% purity.

Workup

  1. customto give a white solid

Sources & evidence

ORD record
ord-f88d5bfc4a864460a9f6fd0e5d93679e
Source dataset
uspto-grants-2005_09
Patent number
US06943162B2

Reaction notes

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