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 509635ノート

反応式

HRID 509635 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-593aaf6220284984a0c582f342a42b29
出典データセット
uspto-grants-2015_08
特許番号
US09096590B2

反応ノート

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