Potassium Iodide → HCID 58110009, compound

HRID 1803249Notes

Reaction equation

HRID 1803249 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([C:14]1[N:18]=[C:17]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[C:30]([CH3:32])[N:29]=[N:28][CH:27]=3)=[C:22]([O:33][CH3:34])[CH:21]=2)[NH:16][N:15]=1)[C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C>[F:13][C:10]1[CH:11]=[CH:12][C:7]([CH:6]2[CH2:5][CH2:4][CH2:3][CH2:2][N:15]3[N:16]=[C:17]([NH:19][C:20]4[CH:25]=[CH:24][C:23]([C:26]5[CH:31]=[C:30]([CH3:32])[N:29]=[N:28][CH:27]=5)=[C:22]([O:33][CH3:34])[CH:21]=4)[N:18]=[C:14]23)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 178493067HCID 178493067, compound

Product 1

HCID 58110009HCID 58110009, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 3-(5-chloro-1-(4-fluorophenyl)pentyl)-N-(3-methoxy-4-(6-methylpyridazin-4-yl)phenyl)-1H-1,2,4-triazol-5-amine (102 mg, 0.212 mmol), potassium carbonate (117 mg, 0.848 mmol), and potassium iodide (70.4 mg, 0.424 mmol) in DMF (5 mL) was heated at 55° C. for 5 hrs. The solvent was removed in vacuo. The crude product was purified using silica gel column chromatography (0-10% MeOH/CH2Cl2, linear gradient) to afford 36 mg (36% yield) of the titled compound as a solid. LC-MS (M+H)+ 455.3. 1H NMR (500 MHz, methanol-d4) δ ppm 9.19 (s, 1 H) 7.68 (s, 1 H) 7.45 (s, 1 H) 7.33 (d, J=8.55 Hz, 1 H) 7.20 (dd, J=8.09, 5.65 Hz, 2 H) 7.00-7.10 (m, 3 H) 4.34 (d, J=8.24 Hz, 1 H) 4.14-4.30 (m, 2 H) 3.77 (s, 3 H) 2.64 (s, 3 H) 2.11-2.26 (m, 1 H) 1.71-2.08 (m, 5 H).

Workup

  1. customThe solvent was removed in vacuo
  2. customThe crude product was purified

Sources & evidence

ORD record
ord-fd278cc336c2456bb9c4678542deb159
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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