Sodium Iodide → HCID 58109981, compound

HRID 1803281Notes

Reaction equation

HRID 1803281 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[CH:34]=[N:33][C:32]([CH3:35])=[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[CH:34]=[N:33][C:32]([CH3:35])=[N:31]1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 66858773HCID 66858773, compound

Product 1

HCID 58109981HCID 58109981, compoundYield 22.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 5-(5-chloro-1-(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 (3.07 g, 5.85 mmol), sodium iodide (4.38 g, 29.3 mmol), and diisoproplylethylamine (5.11 mL, 29.3 mmol) in acetone (100 mL) was heated in a sealed vessel at 100° C. for 12 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. Ethanol (50 mL) was added to the residue. The mixture was stirred at rt for 30 min. The solid was collected by vacuum filtration to afford 630 mg (21% yield) of the titled compound as an off-white solid. LC-MS (M+H)+ 488.5. 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 8.39 (d, J=2.4 Hz, 1 H), 7.68 (dd, J=14.0, 2.4 Hz, 1 H), 7.61 (t, J=8.5 Hz, 1 H), 7.17-7.26 (m, 4H), 7.02 (dd, J=89, 2.4 Hz, 1 H), 6.78 (s, 1H), 4.31 (dd, J=8.5, 2.4 Hz, 1 H), 4.26 (t, J=4.9 Hz, 2 H), 2.50 (s, 3 H), 2.17-2.29 (m, 1H), 2.06-2.16 (m, 1H), 1.86-2.03 (m, 4H).

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. additionEthanol (50 mL) was added to the residue
  9. filtrationThe solid was collected by vacuum filtration

Sources & evidence

ORD record
ord-5c12dbf0937541c58b9266a5cfb17017
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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