Cesium fluoride → HCID 66598078, compound

HRID 1483788Notes

Reaction equation

[F:1][C:2]1([F:10])[CH2:7][CH2:6][CH:5]([CH2:8][NH2:9])[CH2:4][CH2:3]1.Cl[C:12]1[CH:13]=[CH:14][C:15]2[N:16]([C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]([F:31])([F:30])[F:29])[CH:22]=3)=[CH:19][N:20]=2)[N:17]=1.CCN(C(C)C)C(C)C.[F-].[Cs+]>CS(C)=O>[F:1][C:2]1([F:10])[CH2:7][CH2:6][CH:5]([CH2:8][NH:9][C:12]2[CH:13]=[CH:14][C:15]3[N:16]([C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]([F:29])([F:31])[F:30])[CH:22]=4)=[CH:19][N:20]=3)[N:17]=2)[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 120 °C

Procedure

To the solution of compound (4,4-difluorocyclohexyl)methanamine (100 mg, 6 mmol) and compound 6-chloro-3-(3-(trifluoromethoxy)phenyl)imidazo[1,2-b]pyridazine (190 mg, 6 mmol) in 3 mL DMSO was added DIEA (0.21 mL, 12 mmol) and 10 mg CsF, the solvent was stirred for 5 h at 120° C., Then the mixture was purified by HPLC to afford the compound N-((4,4-difluorocyclohexyl)methyl)-3-(3-(trifluoromethoxy)phenyl)imidazo[1,2-b]pyridazin-6-amine (21 mg, 10%) as a white solid.

Workup

customthe mixture was purified by HPLC

Sources & evidence

ORD record: ord-3738a81ad2ad4c6c8749c421ba028dde
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09416132B2

Reaction notes

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