(Oxan-4-yl)methanol → HCID 66598032, compound

HRID 1483802Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.Cl[C:10]1[CH:11]=[CH:12][C:13]2[N:14]([C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]([F:29])([F:28])[F:27])[CH:20]=3)=[CH:17][N:18]=2)[N:15]=1.CC([O-])(C)C.[K+]>O1CCOCC1>[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][O:8][C:10]2[CH:11]=[CH:12][C:13]3[N:14]([C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]([F:27])([F:29])[F:28])[CH:20]=4)=[CH:17][N:18]=3)[N:15]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 70 °C

Procedure

To the solution of compound (tetrahydro-2H-pyran-4-yl)methanol (100 mg, 0.86 mmol) and compound 6-chloro-3-(3-(trifluoromethoxy)phenyl)imidazo[1,2-b]pyridazine (270 mg, 0.86 mmol) in 10 mL dioxane was added t-BuOK (200 mg, 1.78 mmol). The mixture was stirred at 70° C. for 4 hrs. Then the mixture was purified by Pre-HPLC to afford the compound 6-((tetrahydro-2H-pyran-4-yl)methoxy)-3-(3-(trifluoromethoxy)phenyl)imidazo[1,2-b]pyridazine (25 mg, 12%) as a white solid.

Workup

customThen the mixture was purified by Pre-HPLC

Sources & evidence

ORD record: ord-c65d7967adc3422d91598135b9d6136e
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09416132B2

Reaction notes

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