Methanol → 6-(difluoro(6-(1-methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methyl)imidazo[1,2-b]pyridazin-2-amine

HRID 1925164Notes

Reaction equation

HRID 1925164 reaction equation
[F:1][C:2]([F:33])([C:18]1[N:22]2[CH:23]=[C:24]([C:27]3[CH:28]=[N:29][N:30]([CH3:32])[CH:31]=3)[CH:25]=[CH:26][C:21]2=[N:20][N:19]=1)[C:3]1[CH:4]=[CH:5][C:6]2[N:7]([CH:9]=[C:10]([NH:12]C(C3CC3)=O)[N:11]=2)[N:8]=1.CO.O>Cl>[F:33][C:2]([F:1])([C:18]1[N:22]2[CH:23]=[C:24]([C:27]3[CH:28]=[N:29][N:30]([CH3:32])[CH:31]=3)[CH:25]=[CH:26][C:21]2=[N:20][N:19]=1)[C:3]1[CH:4]=[CH:5][C:6]2[N:7]([CH:9]=[C:10]([NH2:12])[N:11]=2)[N:8]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 962WaterHCID 56593558N-(6-(Difluoro(6-(1-methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methyl)imidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxamide

Product 1

HCID 592330706-(difluoro(6-(1-methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methyl)imidazo[1,2-b]pyridazin-2-amineYield 35.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 45 (100 mg) in 3N HCl:50% MeOH:water was heated at 50° C. for 3 hrs. The reaction was concentrated and purified by preparative LCMS to provide the title compound, 6-(difluoro(6-(1-methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methyl)imidazo[1,2-b]pyridazin-2-amine (30 mg) as the TFA salt. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.89 (s, 3 H) 7.46 (br. s., 1 H) 7.51-7.58 (m, 1 H) 7.90 (dd, J=9.47, 1.39 Hz, 1 H) 7.93-7.99 (m, 1 H) 8.04 (d, J=9.60 Hz, 1 H) 8.08 (s, 1 H) 8.39-8.43 (m, 2 H) 8.67 (s, 1 H). ESI-MS:m/z 382.2 (M+H)+.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-7daed9ac3efc4b308c7b3f155028616a
Source dataset
uspto-grants-2012_05
Patent number
US08178534B2

Reaction notes

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