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 2199890노트

반응식

HRID 2199890 반응식
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]

참가 물질

3

반응물 1

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

생성물 1

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

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-fb695990b3924b0e8a29e516ba12ea46
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09359352B2

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