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

HRID 521577

反応式

HRID 521577 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-fccf11d3297a4e2e8d6444d07ac4285a
出典データセット
uspto-grants-2016_05
特許番号
US09328117B2

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