Sodium Iodide → HCID 58110066, compound

HRID 1803325Notes

Reaction equation

HRID 1803325 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([C:19]1[NH:23][N:22]=[C:21]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([N:31]3[CH:35]=[N:34][C:33]([CH3:36])=[N:32]3)=[C:27]([F:37])[CH:26]=2)[N:20]=1)[C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]([F:17])([F:16])[F:15])=[C:9]([F:18])[CH:8]=1.[I-].[Na+].C(N(C(C)C)CC)(C)C>CC(C)=O>[F:37][C:27]1[CH:26]=[C:25]([NH:24][C:21]2[N:20]=[C:19]3[CH:6]([C:7]4[CH:12]=[CH:11][C:10]([O:13][C:14]([F:17])([F:16])[F:15])=[C:9]([F:18])[CH:8]=4)[CH2:5][CH2:4][CH2:3][CH2:2][N:23]3[N:22]=2)[CH:30]=[CH:29][C:28]=1[N:31]1[CH:35]=[N:34][C:33]([CH3:36])=[N:32]1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 866499415-(5-chloro-1-(3-fluoro-4-(trifluoromethoxy)phenyl)pentyl)-N-(3-fluoro-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)-1H-1,2,4-triazol-3-amine

Product 1

HCID 58110066HCID 58110066, compoundYield 22.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 5-(5-chloro-1-(3-fluoro-4-(trifluoromethoxy)phenyl)pentyl)-N-(3-fluoro-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)-1H-1,2,4-triazol-3-amine (989 mg, 1.83 mmol), sodium iodide (1.37 g, 9.13 mmol), and diisopropylethylamine (1.60 mL, 9.13 mmol) in acetone (25 mL) was heated in a sealed vessel at 100° C. for 6 h. The reaction was concentrated in vacuo. The crude product was purified using silica gel column chromatography (70% EtOAc/chloroform). The purified product was recrystallized from EtOAc/hexane to afford 211 mg (22% yield) of the titled compound as a white solid. LC-MS (M+H)+ 506.1. 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 8.40 (1 H, d, J=2.4 Hz), 7.68 (1 H, dd, J=13.9, 2.3 Hz), 7.62 (1 H, t, J=8.7 Hz), 7.31 (1 H, t, J=8.1 Hz), 7.08 (1 H, dd, J=11.0, 2.1 Hz), 7.03 (1 H, dd, J=8.9, 2.4 Hz), 6.98 (1 H, d, J=8.5 Hz), 6.68 (1 H, s), 4.20-4.33 (3 H, m), 2.50 (3 H, s), 2.08-2.22 (2 H, m), 1.94-2.06 (2 H, m), 1.84-1.93 (2 H, m).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customThe crude product was purified
  3. customThe purified product was recrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-24d892d4bd0848a9b4d12da63951f08b
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

Loading…