1-(4-methoxybenzyl)-7-(3-(4-isopropylpiperazin-1-yl)azetidin-1-yl)-1,5-naphthyridin-2(1H)-one → 7-(3-(4-isopropylpiperazin-1-yl)azetidin-1-yl)-1,5-naphthyridin-2(1H)-one

HRID 2199890ノート

反応式

HRID 2199890 の反応式
COC1C=CC(C[N:8]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([N:18]4[CH2:21][CH:20]([N:22]5[CH2:27][CH2:26][N:25]([CH:28]([CH3:30])[CH3:29])[CH2:24][CH2:23]5)[CH2:19]4)[CH:16]=3)[CH:11]=[CH:10][C:9]2=[O:31])=CC=1>C(O)(C(F)(F)F)=O>[CH:28]([N:25]1[CH2:26][CH2:27][N:22]([CH:20]2[CH2:19][N:18]([C:15]3[CH:16]=[C:17]4[C:12]([CH:11]=[CH:10][C:9](=[O:31])[NH:8]4)=[N:13][CH:14]=3)[CH2:21]2)[CH2:23][CH2:24]1)([CH3:30])[CH3:29]

参加物

3

反応物 1

HCID 679930501-(4-methoxybenzyl)-7-(3-(4-isopropylpiperazin-1-yl)azetidin-1-yl)-1,5-naphthyridin-2(1H)-one

生成物 1

HCID 679930417-(3-(4-isopropylpiperazin-1-yl)azetidin-1-yl)-1,5-naphthyridin-2(1H)-one収率 95.7%

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

1-(4-methoxybenzyl)-7-(3-(4-isopropylpiperazin-1-yl)azetidin-1-yl)-1,5-naphthyridin-2(1H)-one (C-8) (5.6 g, 12.5 mmol, 1.0 eq) was dissolved in TFA (100 mL) and the resulting mixture was stirred at reflux for 16 h. The reaction was complete based on TLC analysis. The mixture was cooled to RT and concentrated in vacuo to remove TFA. The resulting suspension was diluted with water (200 mL) and neutralized with sodium carbonate to adjust the pH value to 8-9 while keeping the temperature below 0° C. The resulting mixture was stirred at RT for 30 min. The solid was collected by filtration, rinsed with water (2×50 mL) and dried in vacuo to afford the desired product 7-(3-(4-isopropylpiperazin-1-yl)azetidin-1-yl)-1,5-naphthyridin-2(1H)-one (C-9) (3.91 g, 95.7% yield) as a white solid. ESI-MS m/z: 328.2 [M+H]+.

後処理

  1. temperatureat reflux for 16 h
  2. concentrationconcentrated in vacuo
  3. customto remove TFA
  4. additionThe resulting suspension was diluted with water (200 mL)
  5. customthe temperature below 0° C
  6. stirringThe resulting mixture was stirred at RT for 30 min
  7. filtrationThe solid was collected by filtration
  8. washrinsed with water (2×50 mL)
  9. customdried in vacuo

出典と根拠

ORDレコード
ord-fb695990b3924b0e8a29e516ba12ea46
出典データセット
uspto-grants-2016_06
特許番号
US09359352B2

反応ノート

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