Water → N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxamide

HRID 1925101Notes

Reaction equation

HRID 1925101 reaction equation
Cl.[I:2][C:3]1[CH:4]=[CH:5][C:6]2[N:7]([CH:9]=[C:10]([NH2:12])[N:11]=2)[N:8]=1.[CH:13]1([C:16](Cl)=[O:17])[CH2:15][CH2:14]1.O>CC(N(C)C)=O>[I:2][C:3]1[CH:4]=[CH:5][C:6]2[N:7]([CH:9]=[C:10]([NH:12][C:16]([CH:13]3[CH2:15][CH2:14]3)=[O:17])[N:11]=2)[N:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 77637Cyclopropanecarbonyl chlorideHCID 86639817HCID 86639817, compound

Product 1

HCID 57386058N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxamideYield 77%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Compound 3C was synthesized according to a procedure analogous to that described in International Patent Publication No. WO 2008/06192 (Takeda Pharmaceutical Company Limited), which is incorporated by reference herein in its entirety. 6-Iodoimidazo[1,2-b]pyridazin-2-amine hydrochloride (4.45 g, 17.11 mmol) and cyclopropanecarbonyl chloride (1.35 mL, 18.82 mmol) were dissolved in DMA (85 mL) and stirred for 3 hours at ambient temperature. The reaction mixture was then poured into water (400 mL) resulting in the formation of a brown precipitate. The solid was filtered and dried under vacuum to give N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxamide (4.2 g, 77%). 1H NMR (400 MHz, DMSO-d6) δ=11.21 (s, 1 H), 8.26-8.17 (m, 1 H), 7.74 (d, J=9.3 Hz, 1 H), 7.49 (d, J=9.1 Hz, 1 H), 2.07-1.87 (m, 1 H), 0.97-0.77 (m, 4 H) ESI-MS:m/z 329.1 (M+H)+.

Workup

  1. customCompound 3C was synthesized
  2. customresulting in the formation of a brown precipitate
  3. filtrationThe solid was filtered
  4. customdried under vacuum

Sources & evidence

ORD record
ord-077a265e24f44625b7dc770363085f86
Source dataset
uspto-grants-2012_05
Patent number
US08178534B2

Reaction notes

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