Sodium Iodide → HCID 58110118, compound

HRID 1803282Notes

Reaction equation

HRID 1803282 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([C:18]1[NH:22][N:21]=[C:20]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([N:30]3[C:34]([CH3:35])=[N:33][CH:32]=[N:31]3)=[C:26]([F:36])[CH:25]=2)[N:19]=1)[C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]([F:17])([F:16])[F:15])=[CH:9][CH:8]=1.[I-].[Na+]>CC(C)=O>[F:36][C:26]1[CH:25]=[C:24]([NH:23][C:20]2[N:19]=[C:18]3[CH:6]([C:7]4[CH:12]=[CH:11][C:10]([O:13][C:14]([F:17])([F:16])[F:15])=[CH:9][CH:8]=4)[CH2:5][CH2:4][CH2:3][CH2:2][N:22]3[N:21]=2)[CH:29]=[CH:28][C:27]=1[N:30]1[C:34]([CH3:35])=[N:33][CH:32]=[N:31]1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 66858718HCID 66858718, compound

Product 1

HCID 58110118HCID 58110118, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 5-(5-chloro-1-(4-(trifluoromethoxy)phenyl)pentyl)-N-(3-fluoro-4-(5-methyl-1H-1,2,4-triazol-1-yl)phenyl)-1H-1,2,4-triazol-3-amine (2.00 g, 3.81 mmol), sodium iodide (2.90 g, 19.1 mmol), and diisoproplylethylamine (3.33 mL, 19.1 mmol) in acetone (25 mL) was heated in a sealed vessel at 100° C. for 6 h. The reaction was concentrated in vacuo. Water (250 mL) was added and the mixture was extracted with EtOAc (2×250 mL). The combined organic layers were washed with brine (50 mL), dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified using silica gel column chromatography (70% EtOAc/chloroform) to afford 350 mg (19% yield) of the titled compound as a white solid. LC-MS (M+H)+ 488.1. 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 7.96 (s, 1 H), 7.68 (dd, J=12.7, 2.3 Hz, 1 H), 7.26-7.29 (m, 1 H), 7.19-7.25 (m, 4 H), 7.04 (dd, J=8.9, 2.1 Hz, 1H), 6.87 (s, 1 H), 4.31 (dd, J=8.9, 2.4 Hz, 1 H), 4.27 (t, J=5.0 Hz, 2 H), 2.39 (s, 3 H), 2.17-2.29 (m, 1 H), 2.06-2.16 (m, 1 H), 1.84-2.04 (m, 4 H).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. additionWater (250 mL) was added
  3. extractionthe mixture was extracted with EtOAc (2×250 mL)
  4. washThe combined organic layers were washed with brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified

Sources & evidence

ORD record
ord-f9b188876d104aec98feed8d314818f2
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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