4-methoxybenzyl 4-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]butane-1-sulfonamide → 4-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]butane-1-sulfonamide

HRID 1818174노트

반응식

HRID 1818174 반응식
COC1C=CC(C[CH:8]([S:36]([NH2:39])(=[O:38])=[O:37])[CH2:9][CH2:10][CH2:11][N:12]2[C:24]3[C:23]4[CH:22]=[CH:21][C:20]([C:25]5[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=5)=[CH:19][C:18]=4[N:17]=[C:16]([NH2:31])[C:15]=3[N:14]=[C:13]2[CH2:32][O:33][CH2:34][CH3:35])=CC=1>FC(F)(F)C(O)=O>[NH2:31][C:16]1[C:15]2[N:14]=[C:13]([CH2:32][O:33][CH2:34][CH3:35])[N:12]([CH2:11][CH2:10][CH2:9][CH2:8][S:36]([NH2:39])(=[O:38])=[O:37])[C:24]=2[C:23]2[CH:22]=[CH:21][C:20]([C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)=[CH:19][C:18]=2[N:17]=1

참가 물질

3

반응물 1

HCID 688190684-methoxybenzyl 4-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]butane-1-sulfonamide

생성물 1

HCID 219840384-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]butane-1-sulfonamide수율 77.5%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

A solution of 4-methoxybenzyl 4-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]butane-1-sulfonamide (0.50 g, 0.88 mmol) in trifluoroacetic acid (5 mL) was stirred at ambient temperature for four hours and then concentrated under reduced pressure. The residue was dissolved in methanol and concentrated under reduced pressure; this process was repeated three times. The residue was then suspended in water, and 2 M aqueous sodium hydroxide was added to adjust to pH 7. The mixture was stirred for 30 minutes, and the resulting solid was isolated by filtration, washed with water, and purified by HPFC (eluting with chloroform:CMA in a gradient from 100:0 to 30:70). The purified product was dried overnight under high vacuum at 80° C. to provide 0.31 g of 4-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]butane-1-sulfonamide as tan needles, mp 250-251.5° C.

후처리

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in methanol
  3. concentrationconcentrated under reduced pressure
  4. addition2 M aqueous sodium hydroxide was added
  5. customthe resulting solid was isolated by filtration
  6. washwashed with water
  7. custompurified by HPFC (
  8. washeluting with chloroform
  9. customThe purified product was dried overnight under high vacuum at 80° C.

출처 및 근거

ORD 기록
ord-2b17de9dc4cd4ae8a49d0443624a223f
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07598382B2

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