Sodium Iodide → HCID 58110173, compound

HRID 1803329Notes

Reaction equation

HRID 1803329 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:14]2[NH:18][N:17]=[C:16]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([N:26]4[CH:30]=[C:29]([Cl:31])[N:28]=[CH:27]4)=[C:22]([O:32][CH3:33])[CH:21]=3)[N:15]=2)[CH2:9][CH2:10][CH2:11][CH2:12]Cl)=[CH:4][CH:3]=1.[I-].[Na+].C(N(C(C)C)CC)(C)C>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12][N:18]3[N:17]=[C:16]([NH:19][C:20]4[CH:25]=[CH:24][C:23]([N:26]5[CH:30]=[C:29]([Cl:31])[N:28]=[CH:27]5)=[C:22]([O:32][CH3:33])[CH:21]=4)[N:15]=[C:14]23)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 66858196HCID 66858196, compound

Product 1

HCID 58110173HCID 58110173, compoundYield 20.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 5-(1-(4-bromophenyl)-5-chloropentyl)-N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-1H-1,2,4-triazol-3-amine (2.5 g, 4.54 mmol), sodium iodide (3.40 g, 22.7 mmol), and diisopropylethylamine (0.793 mL, 4.54 mmol) in acetone (10 mL) was heated in a sealed vessel at 100° C. for 12 h. The reaction was concentrated in vacuo. The crude product was purified using silica gel column chromatography (50% EtOAc/chloroform) to afford 475 mg (19% yield) of the titled compound as an off-white solid. LC-MS (M+H)+ 515.1. 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 7.45-7.47 (m, 3 H), 7.40 (d, J=2.1 Hz, 1 H), 7.04-7.10 (m, 3 H), 7.00 (d, J=1.5 Hz, 1 H), 6.79 (dd, J=8.5, 2.4 Hz, 1 H), 6.64 (s, 1 H), 4.15-4.27 (m, 3 H), 3.76 (s, 3 H), 2.14-2.21 (m, 1 H), 1.91-2.10 (m, 3 H), 1.80-1.91 (m, 2 H).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customThe crude product was purified

Sources & evidence

ORD record
ord-d8dea7f98bdb4582b9afcfba1cdb99e4
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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