Potassium Iodide → HCID 86649929, compound

HRID 1803276Notes

Reaction equation

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

Participants

Conditions

Temperature: 72 °C

Procedure

To a solution of N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-5-(2-(4-chlorobutyl)-1,3-dithian-2-yl)-1H-1,2,4-triazol-3-amine (110 mg, 0.220 mmol) in DMF (3 mL) was added potassium carbonate (122 mg, 0.881 mmol) and potassium iodide (73.1 mg, 0.440 mmol). The mixture was stirred at 72° C. for 5 h. The mixture was concentrated in vacuo. The residue was purified using silica gel column chromatography (0-80% EtOAc/hexanes, linear gradient) to afford N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-5,6,7,8-tetrahydrospiro[[1,2,4]triazolo[1,5-a]azepine-9,2′-[1,3]dithian]-2-amine (90 mg, 0.185 mmol, 84% yield). LC-MS (M+H)+=463.1.

Workup

concentrationThe mixture was concentrated in vacuo
customThe residue was purified

Sources & evidence

ORD record: ord-5547daf4f5f84e27b7505de058934a3c
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349880B2

Reaction notes

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