Tetrahydrofuran → 1-{3-[4-amino-8-(2-aminoethyl)-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propyl}pyrrolidin-2-one

HRID 244871노트

반응식

HRID 244871 반응식
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:24][CH2:25][O:26][CH3:27])[N:14]([CH2:15][CH2:16][CH2:17][N:18]3[CH2:22][CH2:21][CH2:20][C:19]3=[O:23])[C:10]=2[C:9]2[CH:8]=[C:7]([CH2:28][CH2:29][N:30]3C(=O)C4C(=CC=CC=4)C3=O)[CH:6]=[CH:5][C:4]=2[N:3]=1.O1CCCC1.O.NN>C(O)C>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:24][CH2:25][O:26][CH3:27])[N:14]([CH2:15][CH2:16][CH2:17][N:18]3[CH2:22][CH2:21][CH2:20][C:19]3=[O:23])[C:10]=2[C:9]2[CH:8]=[C:7]([CH2:28][CH2:29][NH2:30])[CH:6]=[CH:5][C:4]=2[N:3]=1

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 24654Hydrazine hydrate (1:1)2회HCID 690766432-(2-{4-amino-2-(2-methoxyethyl)-1-[3-(2-oxopyrrolidin-1-yl)propyl]-1H-imidazo[4,5-c]quinolin-8-yl}ethyl)-1H-isoindole-1,3(2H)dione

생성물 1

HCID 576572621-{3-[4-amino-8-(2-aminoethyl)-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propyl}pyrrolidin-2-one수율 38.6%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

2-(2-{4-Amino-2-(2-methoxyethyl)-1-[3-(2-oxopyrrolidin-1-yl)propyl]-1H-imidazo[4,5-c]quinolin-8-yl}ethyl)-1H-isoindole-1,3(2H)dione (2.2 g, 4.1 mmol) was dissolved in 2:1 ethanol:tetrahydrofuran (40 mL), combined with hydrazine hydrate (410 mg, 8.2 mmol) and heated at reflux temperature for three hours. Additional hydrazine hydrate (0.25 mL) was added and the solution was refluxed for an additional 1.5 hours. The reaction was cooled to ambient temperature, filtered and the filtrate concentrated under reduce pressure. Purification by chromatography using a HORIZON HPFC system (silica cartridge, eluting with a 0-40% CMA:chloroform gradient over 3.8 L) provided 650 mg of 1-{3-[4-amino-8-(2-aminoethyl)-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propyl}pyrrolidin-2-one as an off-white solid. MS (ESI) m/z 411 (M+H)+.

후처리

  1. temperatureheated
  2. temperatureat reflux temperature for three hours
  3. temperaturethe solution was refluxed for an additional 1.5 hours
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated
  6. customPurification by chromatography
  7. washeluting with a 0-40% CMA

출처 및 근거

ORD 기록
ord-c764cff3d85940a1b48fac4dbf64836d
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658666B2

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