Potassium Iodide → (6-(2-([1,2,4]Triazolo[4,3-a]pyridin-3-yl)propan-2-yl)imidazo[1,2-b]pyridazin-2-yl)(cyclopropyl)methanone

HRID 1925163Notes

Reaction equation

F[C:2](F)(F)[C:3](O)=O.[N:8]1[N:9]=[C:10]([C:17]([C:20]2[N:25]=[N:24][C:23]([NH2:26])=[CH:22][CH:21]=2)([CH3:19])[CH3:18])[N:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=12.BrCC(N[C:32]([CH:34]1[CH2:36][CH2:35]1)=[O:33])=O.P([O-])([O-])(O)=O.[Na+].[Na+].[I-].[K+]>CC(N(C)C)=O>[N:8]1[N:9]=[C:10]([C:17]([C:20]2[CH:21]=[CH:22][C:23]3[N:24]([CH:2]=[C:3]([C:32]([CH:34]4[CH2:35][CH2:36]4)=[O:33])[N:26]=3)[N:25]=2)([CH3:19])[CH3:18])[N:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=12

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 6-(2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)propan-2-yl)pyridazin-3-amine 2,2,2-trifluoroacetate (50 mg, 0.136 mmol), N-(2-bromoacetyl)cyclopropanecarboxamide (28.0 mg, 0.136 mmol), sodium hydrogenphosphate (57.8 mg, 0.407 mmol), and potassium iodide (22.54 mg, 0.136 mmol) in DMA (Volume: 1160 μl) was heated in a microwave on high absorbance for 1 hr at 100° C. The reaction was purified by preparative LCMS to provide the title compound, (6-(2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)propan-2-yl)imidazo[1,2-b]pyridazin-2-yl)(cyclopropyl)methanone (54, 13 mg, 26%) as a TFA salt. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.81 (d, J=6.06 Hz, 4 H) 1.87-2.00 (m, 7 H) 6.92-6.97 (m, 1 H) 7.12 (d, J=9.60 Hz, 1 H) 7.55 (dd, J=8.97, 6.69 Hz, 1 H) 7.87-8.01 (m, 3H) 8.04 (s, 1 H) 11.16 (s, 1 H). ESI-MS:m/z 362.1 (M+H)+.

Workup

customThe reaction was purified by preparative LCMS

Sources & evidence

ORD record: ord-63d24aa437f84b4c8592ef1ef52d45ba
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178534B2

Reaction notes

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