Bromoacetonitrile → HCID 59233033, compound

HRID 1925155Notes

Reaction equation

HRID 1925155 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH:11]([C:13]3[N:18]=[N:17][C:16]([NH2:19])=[CH:15][CH:14]=3)[CH3:12])=[N:9][N:10]=2)[CH:7]=1.Br[CH2:21][C:22]#[N:23].C([O-])(O)=O.[Na+]>CC(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH:11]([C:13]3[CH:14]=[CH:15][C:16]4[N:17]([CH:21]=[C:22]([NH2:23])[N:19]=4)[N:18]=3)[CH3:12])=[N:9][N:10]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 11534BromoacetonitrileHCID 516892Sodium BicarbonateHCID 59233098HCID 59233098, compound

Product 1

HCID 59233033HCID 59233033, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-(1-(6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)ethyl)pyridazin-3-amine (1.0 g, 3.13 mmol), 2-bromoacetonitrile (0.251 ml, 3.76 mmol) and NaHCO3 (0.053 g) in IPA (10 mL) was heated at 100° C. in a sealed tube for 2 hrs. The solid was filtered off, rinsed with IPA, and stripped to dryness via rotary evaporation. The resulting residue was purified by LCMS and lyophilized as a TFA salt to provide the title compound, 6-(1-(6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)ethyl)imidazo[1,2-b]pyridazin-2-amine 48G (0.62 mg, 1.73 mmol, 55%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.85 (d, J=7.07 Hz, 3 H) 5.17 (d, J=7.07 Hz, 1 H) 7.38-7.57 (m, 3 H) 7.80 (d, J=9.60 Hz, 1 H) 7.99 (d, J=9.09 Hz, 1 H) 8.78 (s, 1 H). ESI-MS:m/z 358.1 (M+H)+.

Workup

  1. filtrationThe solid was filtered off
  2. washrinsed with IPA
  3. customstripped to dryness via rotary evaporation
  4. customThe resulting residue was purified by LCMS

Sources & evidence

ORD record
ord-fabdb70245554696bdcd3f480a729a46
Source dataset
uspto-grants-2012_05
Patent number
US08178534B2

Reaction notes

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