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

HRID 1094863노트

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HRID 1094863 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매2회

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온도
60 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ea0176e86bfd465db011dd7ec7fba5c8
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08133995B2

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