Cyclopropylamine → 4-(6-Bromo-8-isobutylamino-imidazo[1,2-a]pyrazin-3-yl)-N-cyclopropyl-2-methyl-benzamide

HRID 1498610Notes

Reaction equation

[Br:1][C:2]1[N:3]=[C:4]([NH:21][CH2:22][CH:23]([CH3:25])[CH3:24])[C:5]2[N:6]([C:8]([C:11]3[CH:19]=[CH:18][C:14]([C:15](O)=[O:16])=[C:13]([CH3:20])[CH:12]=3)=[CH:9][N:10]=2)[CH:7]=1.[CH:26]1([NH2:29])[CH2:28][CH2:27]1.F[P-](F)(F)(F)(F)F.CN([C+](N(C)C)N1C2C(=NC=CC=2)[N+]([O-])=N1)C.C(N(C(C)C)C(C)C)C>CN1CCCC1=O>[Br:1][C:2]1[N:3]=[C:4]([NH:21][CH2:22][CH:23]([CH3:24])[CH3:25])[C:5]2[N:6]([C:8]([C:11]3[CH:19]=[CH:18][C:14]([C:15]([NH:29][CH:26]4[CH2:28][CH2:27]4)=[O:16])=[C:13]([CH3:20])[CH:12]=3)=[CH:9][N:10]=2)[CH:7]=1

Participants

Conditions

Temperature: 23 °C

Procedure

To a solution of 411 mg (1 mmol) 4-(6-Bromo-8-isobutylamino-imidazo[1,2-a]pyrazin-3-yl)-2-methyl-benzoic acid which was prepared according to intermediate example 49b in 4 mL 1-methylpyrrolidin-2-one were added 114.9 mg cyclopropanamine, 760 mg bis(dimethylamino)(3-oxido-1H-[1,2,3]triazolo[4,5-b]pyridin-1-yl)methylium hexafluorophosphate and 685 μL N-ethyl-N-isopropylpropan-2-amine and the mixture was stirred overnight at 23° C. After filtration and removal of the solvent the residue was purified by chromatography to give 65.5 mg (15%) of the title compound.

Workup

filtrationAfter filtration and removal of the solvent the residue
customwas purified by chromatography

Sources & evidence

ORD record: ord-0ba8bcd1246e47ec9175e1d70ce07d83
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199999B2

Reaction notes

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