Sodium Iodide → HCID 46864817, compound

HRID 1803244Notes

Reaction equation

HRID 1803244 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([C:15]1[NH:19][N:18]=[C:17]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH:31]=[C:30]([Cl:32])[N:29]=[CH:28]3)=[C:23]([O:33][CH3:34])[CH:22]=2)[N:16]=1)[C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[C:9]([F:14])[CH:8]=1.[I-].[Na+]>CC(C)=O>[Cl:32][C:30]1[N:29]=[CH:28][N:27]([C:24]2[CH:25]=[CH:26][C:21]([NH:20][C:17]3[N:16]=[C:15]4[CH:6]([C:7]5[CH:12]=[C:11]([F:13])[CH:10]=[C:9]([F:14])[CH:8]=5)[CH2:5][CH2:4][CH2:3][CH2:2][N:19]4[N:18]=3)=[CH:22][C:23]=2[O:33][CH3:34])[CH:31]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 66860145HCID 66860145, compound

Product 1

HCID 46864817HCID 46864817, compoundYield 4.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 5-(5-chloro-1-(3,5-difluorophenyl)pentyl)-N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-1H-1,2,4-triazol-3-amine (855 mg, 1.685 mmol), sodium iodide (1.26 g, 8.43 mmol), and diisoproplylethylamine (0.589 mL, 3.37 mmol) in acetone (20 mL) was heated in a sealed vessel at 100° C. for 4 h. The reaction was concentrated in vacuo. The crude product was purified using reverse phase preparatory-HPLC (MeOH/water/TFA). The purified material was crystallized from methanol to afford 34 mg (4% yield) of the titled compound as a white solid. LC-MS (M+H)+ 471.3. 1H NMR (500 MHz, chloroform-d) δ ppm 7.52 (d, J=1.53 Hz, 1 H) 7.42 (d, J=2.44 Hz, 1 H) 7.10 (d, J=8.55 Hz, 1 H) 7.03 (d, J=1.53 Hz, 1 H) 6.84 (dd, J=8.55, 2.44 Hz, 1 H) 6.70-6.80 (m, 3 H) 6.65 (s, 1 H) 4.18-4.32 (m, 3 H) 3.81 (s, 3 H) 2.06-2.25 (m, 2 H) 1.84-2.03 (m, 4 H).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customThe crude product was purified
  3. customThe purified material was crystallized from methanol

Sources & evidence

ORD record
ord-bb90578f281d472aaca113d5a9561435
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

Loading…