Acetonitrile → HCID 22324129, compound

HRID 496025Notes

Reaction equation

HRID 496025 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]([F:19])=[CH:15][CH:14]=2)[CH3:9])[N:5]=[C:4]([CH2:20][NH:21][CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)[N:3]=1.[CH3:31][N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1.CC#N.C(O)(C(F)(F)F)=O>O>[F: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:35]3[CH2:36][CH2:37][N:32]([CH3:31])[CH2:33][CH2:34]3)[N:3]=[C:4]([CH2:20][NH:21][CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=3)[N:5]=2)=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 6422Trifluoroacetic acidHCID 531671-MethylpiperazineHCID 87977285HCID 87977285, compound

Product 1

HCID 22324129HCID 22324129, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared in 97% yield via the procedure outlined for Example 14 using 4-{2-[(4-chloro-6-{[3-(4-fluorophenyl)propyl]methylamino}-1,3,5-triazin-2-yl)methylamino]ethyl}phenol and 1-methypiperazine to give a white solid: 1H NMR (CDCl3, 400 MHz) δ 7.12 (s, br, 2H), 7.06 (d, 2H, J=8.0), 6.94 (m, 2H); 6.72 (d, 2H, J=8.0), 4.88 (s, br, 1H) 3.79-3.58 (m, 9H), 3.08 (s, 3H), 3.02 (s, br, 3H), 2.78 (m, 2H), 2.60 (t, 2H, J=7.0), 2.45 (s, br, 4H), 2.34 (s, 3H), 1.88 (m, 2H); low-resolution MS (ES+) m/e 495 (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=12.04 min, 99% purity.

Workup

  1. customto give a white solid

Sources & evidence

ORD record
ord-060b8cd806d9473bb746b2507c66a35a
Source dataset
uspto-grants-2005_09
Patent number
US06943162B2

Reaction notes

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