Potassium Iodide → Oxetan-3-yl-[2-(4-{2-[2-(2,2,2-trifluoro-ethyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-yl}-pyrazol-1-yl)-ethyl]-amine

HRID 708205Notes

Reaction equation

Cl[CH2:2][CH2:3][N:4]1[CH:8]=[C:7]([C:9]2[CH:32]=[CH:31][C:12]3[C:13]4[N:14]=[C:15]([C:21]5[N:22]([CH2:26][C:27]([F:30])([F:29])[F:28])[N:23]=[CH:24][N:25]=5)[S:16][C:17]=4[CH2:18][CH2:19][O:20][C:11]=3[CH:10]=2)[CH:6]=[N:5]1.[O:33]1[CH2:36][CH:35]([NH2:37])[CH2:34]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C>[O:33]1[CH2:36][CH:35]([NH:37][CH2:2][CH2:3][N:4]2[CH:8]=[C:7]([C:9]3[CH:32]=[CH:31][C:12]4[C:13]5[N:14]=[C:15]([C:21]6[N:22]([CH2:26][C:27]([F:30])([F:29])[F:28])[N:23]=[CH:24][N:25]=6)[S:16][C:17]=5[CH2:18][CH2:19][O:20][C:11]=4[CH:10]=3)[CH:6]=[N:5]2)[CH2:34]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 8-[1-(2-chloro-ethyl)-1H-pyrazol-4-yl]-2-[2-(2,2,2-trifluoro-ethyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene (0.200 g, 0.416 mmol) and 3-oxetanamine (0.608 g, 2.08 mmol) in 5 mL of DMF was added potassium carbonate (0.287 g, 2.08 mmol) and potassium iodide (0.069 g, 0.416 mmol). The reaction mixture was heated at 50° C. for approximately 4 hours. The heated was increased to 70 C and the reaction was continued another 15 hours to give the desired product as determined by LCMS. The crude material was purified by RP-HPLC to cleanly give 461. MS: (ESI+)=518.3

Workup

temperatureThe heated was increased to 70 C

Sources & evidence

ORD record: ord-73ef8bbeaa914e8ea8527558aeb5450d
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09175009B2

Reaction notes

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