1-Methylpiperidine-4-methylamine → 7-Methyl-N-((1-methylpiperidin-4-yl)methyl)-3-(3-(trifluoromethoxy)phenyl)-imidazo[1,2-b]pyridazin-6-amine

HRID 2370047Notes

Reaction equation

Cl[C:2]1[C:3]([CH3:22])=[CH:4][C:5]2[N:6]([C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]([F:21])([F:20])[F:19])[CH:12]=3)=[CH:9][N:10]=2)[N:7]=1.[CH3:23][N:24]1[CH2:29][CH2:28][CH:27]([CH2:30][NH2:31])[CH2:26][CH2:25]1.CC([O-])(C)C.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[CH3:22][C:3]1[C:2]([NH:31][CH2:30][CH:27]2[CH2:28][CH2:29][N:24]([CH3:23])[CH2:25][CH2:26]2)=[N:7][N:6]2[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]([F:21])([F:20])[F:19])[CH:12]=3)=[CH:9][N:10]=[C:5]2[CH:4]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To the toluene (5 mL) solvent was added Compound 11 (57 mg, 0.174 mmol), (1-methylpiperidine-4-yl)methanamine 17 (26.8 mg, 0.209 mmol), ligand (10.27 mg, 0.026 mmol), NaOtBu (23.40 mg, 0.244 mmol) and Pd2(dba)3 (11.95, 0.013 mmol). The resulting reaction mixture was degassed for 10 min under argon and then was heated with microwave at 150° C. for 1 h. Concentration and preparative TLC (10% MeOH/DCM) afforded 5.3 mg (7.26%) of Compound 7-37.

Workup

customThe resulting reaction mixture
customwas degassed for 10 min under argon
concentrationConcentration and preparative TLC (10% MeOH/DCM)

Sources & evidence

ORD record: ord-1c77331032204ecbab41b6cf54562b77
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710057B2

Reaction notes

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