Morpholine → 9-(1-hydroxy-2-morpholinoethyl)-6-(4-methoxybenzyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one

HRID 926125

反応式

HRID 926125 の反応式
[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]([CH2:7][N:8]2[C:13]3[N:14]=[CH:15][C:16]([CH:18]4[CH2:20][O:19]4)=[CH:17][C:12]=3[C:11]3=[N:21][CH:22]=[N:23][N:10]3[C:9]2=[O:24])=[CH:5][CH:4]=1.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>>[OH:19][CH:18]([C:16]1[CH:15]=[N:14][C:13]2[N:8]([CH2:7][C:6]3[CH:25]=[CH:26][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[C:9](=[O:24])[N:10]3[N:23]=[CH:22][N:21]=[C:11]3[C:12]=2[CH:17]=1)[CH2:20][N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1

参加物

3

反応物 2

HCID 8083MorpholineHCID 1181150326-(4-Methoxybenzyl)-9-(oxiran-2-yl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one

生成物 1

HCID 727063249-(1-hydroxy-2-morpholinoethyl)-6-(4-methoxybenzyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one収率 26%

実験手順

6-(4-Methoxybenzyl)-9-(oxiran-2-yl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one (118 mg, 0.337 mmol) was treated with morpholine (0.50 mL) and stirred for 16 h at room temperature. The mixture was concentrated under vacuum, re-dissolved in DMSO, and filtered. Purification (HPLC, elution with 20 to 80% acetonitrile in water) afforded the title compound (63 mg, 26%) as the TFA salt as a white powder. 1H NMR (400 MHz, CDCl3) δ 3.11 (br s, 4H), 3.26 (dd, J=13.30, 2.89 Hz, 1H), 3.35 (dd, J=13.30, 10.67 Hz, 1H), 3.76 (s, 3H), 4.12 (br s, 4H), 5.65-5.71 (m, 1H), 5.73 (s, 2H), 6.82 (d, J=8.78 Hz, 2H), 7.58 (d, J=8.66 Hz, 2H), 8.35 (s, 1H), 8.69 (d, J=2.26 Hz, 1H), 8.90 (d, J=2.26 Hz, 1H). [M+H]=437.2.

後処理

  1. concentrationThe mixture was concentrated under vacuum
  2. dissolutionre-dissolved in DMSO
  3. filtrationfiltered
  4. customPurification (HPLC, elution with 20 to 80% acetonitrile in water)

出典と根拠

ORDレコード
ord-02e836163d4148588b132358c328e06b
出典データセット
uspto-grants-2016_03
特許番号
US09284335B2

関連ノート

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