Potassium Iodide → HCID 46864320, compound

HRID 1803258Notes

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]([C:26]3[O:30][N:29]=[C:28]([CH3:31])[N:27]=3)=[C:22]([O:32][CH3:33])[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-:35].[K+].[K+].[I-].[K+].O.C(#N)C>CN(C=O)C>[C:26]([O-:30])(=[O:35])[CH3:23].[NH4+:15].[F:13][C:10]1[CH:11]=[CH:12][C:7]([CH:6]2[CH2:5][CH2:4][CH2:3][CH2:2][N:18]3[N:17]=[C:16]([NH:19][C:20]4[CH:25]=[CH:24][C:23]([C:26]5[O:30][N:29]=[C:28]([CH3:31])[N:27]=5)=[C:22]([O:32][CH3:33])[CH:21]=4)[N:15]=[C:14]23)=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 55 °C

Procedure

A mixture of 5-(5-chloro-1-(4-fluorophenyl)pentyl)-N-(3-methoxy-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)-1H-1,2,4-triazol-3-amine (559 mg, 1.188 mmol), potassium carbonate (657 mg, 4.75 mmol), and potassium iodide (394 mg, 2.376 mmol) in DMF (8 mL) was heated at 55° C. for 16 hrs. The solvent was removed in vacuo. The crude product was purified using reverse phase preparatory-HPLC(Column: Phenomenex Luna C18 30×100 mm, Solvent A=10 mM Ammonium Acetate in 95:5 water/ACN, Solvent B=10 mM Ammonium Acetate in 5:95 water/ACN, Flow rate: 40 ml/min, 30-85% B, 25 min) to afford 9-(4-fluorophenyl)-N-(3-methoxy-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[1,5-a]azepin-2-amine (82 mg, 0.189 mmol, 16% yield). LC-MS (M+H)+ 435.3. 1H NMR (400 MHz, methanol-d4) δ ppm 7.83 (d, J=8.56 Hz, 1 H) 7.56 (d, J=2.01 Hz, 1 H) 7.19-7.28 (m, 2 H) 7.08 (t, J=8.81 Hz, 2 H) 6.99 (dd, J=8.56, 2.01 Hz, 1 H) 4.17-4.43 (m, 3 H) 3.85 (s, 3 H) 2.39 (s, 3 H) 2.17-2.31 (m, 1 H) 2.01-2.11 (m, 1 H) 1.78-1.98 (m, 4 H).

Workup

customThe solvent was removed in vacuo
customThe crude product was purified

Sources & evidence

ORD record: ord-682921600dc24cb6b6fa69d4208a9530
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349880B2

Reaction notes

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