Potassium Iodide → HCID 46864914, compound

HRID 1803251Notes

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

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 5-(5-chloro-1-(4-fluorophenyl)pentyl)-N-(4-(4-chloro-1H-imidazol-1-yl)-3-fluoro-5-methoxyphenyl)-1H-1,2,4-triazol-3-amine (120 mg, 0.237 mmol), potassium carbonate (98 mg, 0.710 tunnel) and potassium iodide (58.9 mg, 0.355 mmol) in DMF (5 mL) was heated at 60° C. for 16 hrs. The solvent was removed in vacuo. The crude product was purified using silica gel column chromatography (0-100% EtOAc/CH2Cl2, linear gradient) to afford 72 mg (65% yield) of the titled compound as a solid. LC-MS (M+H)+ 471.2. 1H NMR (500 MHz, chloroform-d) δ ppm 7.41 (s, 1 H) 7.13 (dd, J=8.39, 5.34 Hz, 2 H) 7.03-7.06 (m, 3 H) 6.91 (s, 1 H) 6.89 (dd, J=11.90, 2.14 Hz, 1 H) 4.28 (d, J=7.32 Hz, 1 H) 4.23 (t, J=4.88 Hz, 2 H) 3.72 (s, 3 H) 2.15-2.26 (m, 1 H) 2.05-2.11 (m, 1 H) 1.79-2.03 (m, 4 H).

Workup

customThe solvent was removed in vacuo
customThe crude product was purified

Sources & evidence

ORD record: ord-dd1578632390489e90f5c610f5bea6a0
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349880B2

Reaction notes

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