Sodium Iodide → HCID 58110159, compound

HRID 1803239Notes

Reaction equation

HRID 1803239 reaction equation
Cl[CH2:2][CH2:3][CH2:4][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[CH:30]=[N:29][C:28]([CH3:31])=[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][CH2:4][CH2:3][CH2:2][N:18]3[N:17]=2)[CH:25]=[CH:24][C:23]=1[N:26]1[CH:30]=[N:29][C:28]([CH3:31])=[N:27]1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 66859119HCID 66859119, compound

Product 1

HCID 58110159HCID 58110159, compoundYield 44.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 5-(5-chloro-1-(4-fluorophenyl)pentyl)-N-(3-fluoro-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)-1H-1,2,4-triazol-3-amine (1.75 g, 3.81 mmol), sodium iodide (2.86 g, 19.1 mmol), and diisoproplylethylamine (3.33 mL, 19.1 mmol) in acetone (50 mL) was heated in a sealed vessel at 100° C. for 4 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 720 mg (43% yield) of the titled compound as an off-white solid. LC-MS (M+H)+ 422.5. 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 8.39 (d, J=2.4 Hz, 1H), 7.68 (dd, J=13.9, 2.3 Hz, 1H), 7.59 (t, J=8.5 Hz, 1H), 7.14 (dd, J=8.5, 5.2 Hz, 2H), 6.97-7.11 (m, 3H), 6.90 (s, 1H), 4.19-4.39 (m, 3H), 2.49 (s, 3H), 2.16-2.32 (m, 1H), 2.06-2.15 (m, 1H), 1.84-2.03 (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-94b20cd1125c46ccb690859e1b9a0445
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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