(S)-(-)-N,alpha-Dimethylbenzylamine → (S)-ethyl 6-(methyl(1-phenylethyl)amino)-[1,2,4]triazolo[4,3-b]pyridazine-3-carboxylate

HRID 521577Notes

Reaction equation

HRID 521577 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:9][N:10]=2)[N:7]=1.[CH3:16][NH:17][C@H:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:19]>CC#N>[CH3:16][N:17]([C@H:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:19])[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:9][N:10]=2)[N:7]=1

Participants

4

Reactant 2

HCID 2060073(S)-(-)-N,alpha-DimethylbenzylamineHCID 11287584Ethyl 6-chloro-(1,2,4)triazolo(4,3-b)pyridazine-3-carboxylate

Product 1

HCID 117624621(S)-ethyl 6-(methyl(1-phenylethyl)amino)-[1,2,4]triazolo[4,3-b]pyridazine-3-carboxylateYield 32.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of ethyl 6-chloro-[1,2,4]triazolo[4,3-b]pyridazine-3-carboxylate (1.5 g, 6.6 mmol) and (S)-N-methyl-1-phenylethanamine (3.6 g, 26.4 mmol) in 20 mL of CH3CN was heated to reflux and stirred for 36 h. When cooled to room temperature, the reaction mixture was concentrated in vacuum, and the residue was purified by flash chromatography eluting with DCM/EA=5:1 to give product (S)-ethyl 6-(methyl(1-phenylethyl)amino)-[1,2,4]triazolo[4,3-b]pyridazine-3-carboxylate as a yellow oil (0.7 g, 32%). LRMS (M+H+) m/z: calcd 326.16; found 326. 1H NMR (300 MHz, CDCl3): δ 8.02-7.99 (d, J=9 Hz, 1H), 7.36-7.26 (m, 5H), 7.09-7.06 (d, J=9 Hz, 1H), 5.82-5.75 (q, 1H), 4.57-4.50 (q, 2H), 2.94 (s, 3H), 1.68-1.65 (d, 3H), 1.48-1.44 (t, 3H).

Workup

  1. temperatureto reflux
  2. concentrationthe reaction mixture was concentrated in vacuum
  3. customthe residue was purified by flash chromatography
  4. washeluting with DCM/EA=5:1

Sources & evidence

ORD record
ord-fccf11d3297a4e2e8d6444d07ac4285a
Source dataset
uspto-grants-2016_05
Patent number
US09328117B2

Reaction notes

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