Sodium Iodide → HCID 66858864, compound

HRID 1803317Notes

Reaction equation

HRID 1803317 reaction equation
Cl[CH2:2][CH2:3][C:4](=[CH2:33])[CH2:5][CH:6]([C:14]1[NH:18][N:17]=[C:16]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([N:26]3[C:30]([CH3:31])=[N:29][CH:28]=[N:27]3)=[C:22]([F:32])[CH:21]=2)[N:15]=1)[C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1.[I-].[Na+]>CC(C)=O>[F:32][C:22]1[CH:21]=[C:20]([NH:19][C:16]2[N:15]=[C:14]3[CH:6]([C:7]4[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=4)[CH2:5][C:4](=[CH2:33])[CH2:3][CH2:2][N:18]3[N:17]=2)[CH:25]=[CH:24][C:23]=1[N:26]1[C:30]([CH3:31])=[N:29][CH:28]=[N:27]1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 66858790HCID 66858790, compound

Product 1

HCID 66858864HCID 66858864, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 5-(5-chloro-1-(4-fluorophenyl)-3-methylenepentyl)-N-(3-fluoro-4-(5-methyl-1H-1,2,4-triazol-1-yl)phenyl)-1H-1,2,4-triazol-3-amine (3.33 g, 7.09 mmol), sodium iodide (5.31 g, 35.4 mmol), and diisoproplylethylamine (2.48 mL, 14.2 mmol) in acetone (50 mL) was heated in a sealed vessel at 100° C. for 1 h. The reaction was concentrated in vacuo. The crude product was purified using silica gel column chromatography (50-100% EtOAc/chloroform). The fractions containing product were combined and concentrated to afford N-(3-fluoro-4-(5-methyl-1H-1,2,4-triazol-1-yl)phenyl)-9-(4-fluorophenyl)-7-methylene-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[1,5-a]azepin-2-amine (2.0 g, 52% yield). LC-MS (M+H)+ 434.1.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customThe crude product was purified
  3. additionThe fractions containing product
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f1c49de22bce4396803215c3ed9e4a13
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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