6-Chloro-3-methyl-(1,2,4)triazolo(4,3-b)pyridazine → (R)-N,3-dimethyl-N-(1-phenylethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-amine

HRID 521558

反応式

HRID 521558 の反応式
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH3:11])=[N:9][N:10]=2)[N:7]=1.[CH3:12][NH:13][C@@H:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:15]>CN1C(=O)CCC1>[CH3:12][N:13]([C@@H:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:15])[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH3:11])=[N:9][N:10]=2)[N:7]=1

参加物

4

反応物 2

HCID 9113876-Chloro-3-methyl-(1,2,4)triazolo(4,3-b)pyridazineHCID 2060888(R)-(+)-N-Methyl-1-phenylethylamine

生成物 1

HCID 71115945(R)-N,3-dimethyl-N-(1-phenylethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-amine

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
200 °C

実験手順

6-Chloro-3-methyl-[1,2,4]triazolo[4,3-b]pyridazine (150 mg, 0.890 mmol; commercially available or prepared according to patent WO2006/039325A2), (R)-N-methyl-1-phenylethanamine (481 mg, 3.56 mmol; available from Aldrich) and anhydrous NMP (1 mL) were charged into a microwave tube equipped with a magnetic stirbar. After the vessel was sealed, the mixture was heated at 200° C. for 60 min using microwave irradiation. The reaction was purified by normal phase (gradient of 0% to 20% MeOH in CH2Cl2 as eluent) and by reverse phase chromatography before being lyophilized to give the (R)-N,3-dimethyl-N-(1-phenylethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-amine (Compound 3) as an off-white solid (115 mg; 48% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.01 (d, J=10.1 Hz, 1H), 7.23-7.41 (m, 6H), 5.71 (q, J=6.8 Hz, 1H), 2.83 (s, 3H), 2.54 (s, 3H), 1.58 (d, J=7.1 Hz, 3H). LRMS [M+H]+: 268 m/z.

後処理

  1. customcommercially available or prepared
  2. additionwere charged into a microwave tube
  3. customequipped with a magnetic stirbar
  4. customAfter the vessel was sealed
  5. custommicrowave irradiation
  6. customThe reaction was purified by normal phase (gradient of 0% to 20% MeOH in CH2Cl2 as eluent) and by reverse phase chromatography

出典と根拠

ORDレコード
ord-cf99951de9604c2f82f7761afb03f0cb
出典データセット
uspto-grants-2016_05
特許番号
US09328117B2

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