Formaldehyde → 1-[4-Amino-7-(morpholin-4-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-6-yl]ethanol

HRID 1094863ノート

反応式

HRID 1094863 の反応式
[NH2:1][C:2]1[C:7]2=[CH:8][C:9]([CH:11]([OH:13])[CH3:12])=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1.[CH2:14]=O.O.[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>CC(O)=O>[NH2:1][C:2]1[C:7]2=[CH:8][C:9]([CH:11]([OH:13])[CH3:12])=[C:10]([CH2:14][N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[N:6]2[N:5]=[CH:4][N:3]=1

参加物

6

反応物 4

HCID 712FormaldehydeHCID 962WaterHCID 8083MorpholineHCID 552977291-{4-Aminopyrrolo[2,1-f][1,2,4]triazin-6-yl}ethan-1-ol

生成物 1

HCID 579552741-[4-Amino-7-(morpholin-4-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-6-yl]ethanol収率 67%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒2 回

反応条件

温度
60 °C

実験手順

To a solution of AcOH (70 mL) was added 1-(4-aminopyrrolo[2,1-f][1,2,4]triazin-6-yl)ethanol (611 mg, 3.43 mmol) followed by the addition of a 0.5 M solution of 37% formaldehyde in water (0.26 mL, 3.43 mmol) and morpholine (0.30 mL, 3.43 mmol) in AcOH (6.86 mL) was added. The reaction was heated to 60° C. for 1.5 h. The solution was allowed to cool to rt and was then evaporated via rotary evaporation chasing the remaining AcOH with toluene. The crude material was purified by column chromatography (85:15 v/v CH2Cl2-EtOAc) to afford 633 mg of the above compound (2.28 mmol, yield 67%). 1H-NMR (DMSO-d6) δ 7.79 (s, 1H), 7.57 (br s, 2H), 6.85 (s, 1H), 4.94 (m, 1H), 3.84 (m, 2H), 3.49 (m, 4H), 2.37 (m, 4H), 1.41 (d, J=6.6 Hz, 3H); MS [M+H]+=278.0; LCMS RT=1.01 min.

後処理

  1. additionwas added
  2. temperatureto cool to rt
  3. customwas then evaporated via rotary evaporation
  4. customThe crude material was purified by column chromatography (85:15 v/v CH2Cl2-EtOAc)

出典と根拠

ORDレコード
ord-ea0176e86bfd465db011dd7ec7fba5c8
出典データセット
uspto-grants-2012_03
特許番号
US08133995B2

反応ノート

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