Hydrochloric Acid → HCID 59233061, compound

HRID 1925181Notes

Reaction equation

HRID 1925181 reaction equation
[N:1]1[N:2]=[C:3]([S:10][C:11]2[CH:12]=[CH:13][C:14]3[N:15]([CH:17]=[C:18]([NH:20]C(=O)OC(C)(C)C)[N:19]=3)[N:16]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.Cl.C(O)(C(F)(F)F)=O>O1CCOCC1>[N:1]1[N:2]=[C:3]([S:10][C:11]2[CH:12]=[CH:13][C:14]3[N:15]([CH:17]=[C:18]([NH2:20])[N:19]=3)[N:16]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 66634119tert-Butyl 6-([1,2,4]triazolo[4,3-a]pyridin-3-ylthio)imidazo[1,2-b]pyridazin-2-ylcarbamate

Product 1

HCID 59233061HCID 59233061, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of tert-butyl 6-([1,2,4]triazolo[4,3-a]pyridin-3-ylthio)imidazo[1,2-b]pyridazin-2-ylcarbamate (300 mg, 0.78 mmol) in dioxane (5 ml) was treated with 4M HCl in dioxane (5 ml) at 80° C. for 1 hr. The mixture was concentrated and purified by LCMS to give the title compound, 6-([1,2,4]triazolo[4,3-a]pyridin-3-ylthio)imidazo[1,2-b]pyridazin-2-amine (201 mg, 68% yield) as the TFA salt. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.00 (d, J=9.35 Hz, 1 H) 7.16 (t, J=6.44 Hz, 1 H) 7.22 (s, 1 H) 7.54-7.65 (m, 1 H) 7.73 (d, J=9.35 Hz, 1 H) 8.00 (d, J=9.09 Hz, 1 H) 8.47 (d, J=6.82 Hz, 1 H). ESI-MS:m/z 284.2 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by LCMS

Sources & evidence

ORD record
ord-436e24d69ec14d9f87dc61a114914856
Source dataset
uspto-grants-2012_05
Patent number
US08178534B2

Reaction notes

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