Methylamine → 2,2-dimethyl-N-[5-(6-methylaminoimidazo[2,1-f]pyridazin-2-yl)-2-(trifluoromethyl)phenyl]propanamide

HRID 539750Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][C:5]2=[N:8][C:9]([C:11]3[CH:12]=[CH:13][C:14]([C:24]([F:27])([F:26])[F:25])=[C:15]([NH:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[CH:16]=3)=[CH:10][N:4]2[N:3]=1.[CH3:28][NH2:29]>C1COCC1>[CH3:20][C:19]([CH3:22])([CH3:21])[C:18]([NH:17][C:15]1[CH:16]=[C:11]([C:9]2[N:8]=[C:5]3[N:4]([CH:10]=2)[N:3]=[C:2]([NH:29][CH3:28])[CH:7]=[CH:6]3)[CH:12]=[CH:13][C:14]=1[C:24]([F:27])([F:26])[F:25])=[O:23]

Participants

Conditions

Temperature: 80 °C

Procedure

A 8 mL vial is charged with N-[5-(6-chloroimidazo[2,1-f]pyridazin-2-yl)-2-(trifluoromethyl)phenyl]-2,2-dimethyl-propanamide (0.032 g, 0.08 mmol), THF (0.649 mL), and methylamine (0.08 mL, 2 M in THF, 0.16 mol). The mixture is stirred and heated to 80° C. for 16 hr. The mixture is concentrated onto celite and purified by silica gel chromatography (0-100% EtOAc in CH2Cl2) to give the title compound (11 mg, 35% yield). LCMS m/z=392.5 [M+H]+, tR=2.36 min. (compound same as Example 137)

Workup

concentrationThe mixture is concentrated onto celite
custompurified by silica gel chromatography (0-100% EtOAc in CH2Cl2)

Sources & evidence

ORD record: ord-14af928eb8af48288ebbdc6417568f2d
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871767B2

Reaction notes

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