Dimethyl Sulfide → 1-(3-Pyridin-2-yl-imidazo[1,2-b]pyridazin-2-yl)-ethylamine

HRID 2036658Notes

Reaction equation

HRID 2036658 reaction equation
C(OC(=O)[NH:10][CH:11]([C:13]1[N:14]=[C:15]2[CH:20]=[CH:19][CH:18]=[N:17][N:16]2[C:21]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1)[CH3:12])C1C=CC=CC=1.CSC>C(O)(C(F)(F)F)=O>[N:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:21]1[N:16]2[N:17]=[CH:18][CH:19]=[CH:20][C:15]2=[N:14][C:13]=1[CH:11]([NH2:10])[CH3:12]

Participants

4

Reactant 2

HCID 1068Dimethyl SulfideHCID 67431406[1-(3-Pyridin-2-yl-imidazo[1,2-b]pyridazin-2-yl)-ethyl]-carbamic acid benzyl ester

Product 1

HCID 674336131-(3-Pyridin-2-yl-imidazo[1,2-b]pyridazin-2-yl)-ethylamineYield 117.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The mixture of [1-(3-pyridin-2-yl-imidazo[1,2-b]pyridazin-2-yl)-ethyl]-carbamic acid benzyl ester (600 mg, 1.6 mmol) and dimethylsulfide (1.2 mL) in TFA (7.5 mL)) was stirred at rt overnight. The mixture was concentrated in vacuo. The residue was dissolved in EtOAc. The organic layer was washed with satd. sodium bicarbonate solution, dried over sodium sulfate, filtered and concentrated in vacuo to provide 1-(3-pyridin-2-yl-imidazo[1,2-b]pyridazin-2-yl)-ethylamine (450 mg): LC-MS (ESI) m/z 240.0 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc
  3. washThe organic layer was washed with satd
  4. dry with materialsodium bicarbonate solution, dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f97399b8b3f74a4b98bbb4d6110aaced
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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