(2S)-5-oxooxolane-2-carboxylic acid → N-[2-(4-Amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethyl]-5-oxotetrahydro-2-furancarboxamide

HRID 497789

반응식

HRID 497789 반응식
[O:1]=[C:2]1[O:6][C@H:5]([C:7]([OH:9])=O)[CH2:4][CH2:3]1.[NH2:10][C:11]1[C:20]2[N:21]=[C:22]([CH2:27][CH2:28][CH2:29][CH3:30])[N:23]([CH2:24][CH2:25][NH2:26])[C:19]=2[C:18]2[N:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:12]=1.Cl.CON(OC)CCCN=C=NCC>ClCCl>[NH2:10][C:11]1[C:20]2[N:21]=[C:22]([CH2:27][CH2:28][CH2:29][CH3:30])[N:23]([CH2:24][CH2:25][NH:26][C:7]([CH:5]3[CH2:4][CH2:3][C:2](=[O:1])[O:6]3)=[O:9])[C:19]=2[C:18]2[N:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:12]=1

참가 물질

5

반응물 3

HCID 636468(2S)-5-oxooxolane-2-carboxylic acidHCID 219460272-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethaneamineHCID 219844591-(3-Dimethoxyaminopropyl)-3-ethylcarbodiimide hydrochloride

생성물 1

HCID 22172717N-[2-(4-Amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethyl]-5-oxotetrahydro-2-furancarboxamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

A solution of (S)-(+)-5-oxo-2-tetrahydrofurancarboxylic acid (0.23 g, 1.7 mmole in anhydrous dichloromethane (30 mL) was slowly added to a solution of 2-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethaneamine (0.5 g, 1.7 mmol) in anhydrous dichloromethane (100 mL). The reaction mixture was stirred at ambient temperature for 30 minutes and then a solution of 1-[3-(dimethoxyamino)propyl]-3-ethylcarbodiimide hydrochloride (0.37 g, 1.9 mmol) in anhydrous dichloromethane (50 mL) was added dropwise. The reaction mixture was stirred at ambient temperature overnight and then filtered to remove solids. The filtrate was washed twice with 10% sodium hydroxide and then with brine, dried, and then concentrated under vacuum to provide 0.3 g of crude product. This material was purified by column chromatography (silica gel eluting with dichloromethane) followed by recrystallization from acetonitrile to provide 0.1 g of N-[2-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethyl]-5-oxotetrahydro-2-furancarboxamide as a white powder, m.p. 153-154° C. Analysis: Calculated for C20H24N6O3: %C, 60.59; %H, 6.10; %N, 21.19; Found: %C, 60.34; %H, 6.14; %N, 21.13. HRMS (EI) calcd for C20H24N6O3 (M+) 396.1909 found 396.1905.

후처리

  1. stirringThe reaction mixture was stirred at ambient temperature overnight
  2. filtrationfiltered
  3. customto remove solids
  4. washThe filtrate was washed twice with 10% sodium hydroxide
  5. dry with materialwith brine, dried
  6. concentrationconcentrated under vacuum
  7. customto provide 0.3 g of crude product
  8. customThis material was purified by column chromatography (silica gel eluting with dichloromethane)
  9. customfollowed by recrystallization from acetonitrile

출처 및 근거

ORD 기록
ord-6dbd3d7481604983acb8a505757c4a96
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06949646B2

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