Potassium Iodide → HCID 46864913, compound

HRID 1803250Notes

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]=[C:24]([F:26])[C:23]([N:27]3[CH:31]=[C:30]([Cl:32])[N:29]=[CH:28]3)=[C:22]([F:33])[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>[Cl:32][C:30]1[N:29]=[CH:28][N:27]([C:23]2[C:24]([F:26])=[CH:25][C:20]([NH:19][C:17]3[N:18]=[C:14]4[CH:6]([C:7]5[CH:8]=[CH:9][C:10]([F:13])=[CH:11][CH:12]=5)[CH2:5][CH2:4][CH2:3][CH2:2][N:15]4[N:16]=3)=[CH:21][C:22]=2[F:33])[CH:31]=1

Participants

Conditions

Temperature: 55 °C

Procedure

A mixture of 3-(5-chloro-1-(4-fluorophenyl)pentyl)-N-(4-(4-chloro-1H-imidazol-1-yl)-3,5-difluorophenyl)-1H-1,2,4-triazol-5-amine (40 mg, 0.081 mmol), potassium carbonate (11.2 mg, 0.081 mmol), and potassium iodide (13.4 mg, 0.081 mmol) in DMF (2 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 28 mg (72% yield) of the titled compound as a solid. LC-MS (M+H)+ 459.2. 1H NMR (500 MHz, chloroform-d) δ ppm 7.49 (s, 1 H) 7.19 (d, J=10.38 Hz, 2 H) 7.14 (dd, J=8.55, 5.49 Hz, 2 H) 7.06 (t, J=8.55 Hz, 2 H) 7.00 (s, 1 H) 4.18-4.33 (m, 3 H) 2.15-2.28 (m, 1H) 1.78-2.15 (m, 5 H).

Workup

customThe solvent was removed in vacuo
customThe crude product was purified

Sources & evidence

ORD record: ord-ee75d8bdc2324b688858093734e1dea7
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349880B2

Reaction notes

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