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

HRID 1818173

Reaktionsgleichung

Reaktionsgleichung von HRID 1818173
[CH3:1][O:2][C:3]1[CH:36]=[CH:35][C:6]([CH2:7][CH:8]([S:31]([NH2:34])(=[O:33])=[O:32])[CH2:9][CH2:10][CH2:11][N:12]2[C:24]3[C:23]4[CH:22]=[CH:21][C:20](Br)=[CH:19][C:18]=4[N:17]=[C:16]([NH2:26])[C:15]=3[N:14]=[C:13]2[CH2:27][O:28][CH2:29][CH3:30])=[CH:5][CH:4]=1.[N:37]1[CH:42]=[CH:41][CH:40]=[C:39](B(O)O)[CH:38]=1>>[CH3:1][O:2][C:3]1[CH:36]=[CH:35][C:6]([CH2:7][CH:8]([S:31]([NH2:34])(=[O:33])=[O:32])[CH2:9][CH2:10][CH2:11][N:12]2[C:24]3[C:23]4[CH:22]=[CH:21][C:20]([C:39]5[CH:38]=[N:37][CH:42]=[CH:41][CH:40]=5)=[CH:19][C:18]=4[N:17]=[C:16]([NH2:26])[C:15]=3[N:14]=[C:13]2[CH2:27][O:28][CH2:29][CH3:30])=[CH:5][CH:4]=1

Komponenten

3

Edukt 2

HCID 27343783-Pyridinylboronic acid2×HCID 688199064-Methoxybenzyl 4-(4-amino-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butane-1-sulfonamide

Produkt 1

HCID 688190684-methoxybenzyl 4-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]butane-1-sulfonamideAusbeute 53,9 %

Versuchsvorschrift

4-Methoxybenzyl 4-(4-amino-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butane-1-sulfonamide (1.16 g, 2.0 mmol) and pyridine-3-boronic acid (0.30 g, 2.4 mmol) were coupled according to the method described in Part J of Example 1. The reaction was heated at reflux for 14 hours, at which time additional pyridine-3-boronic acid (0.3 equivalent) was added and the reaction was heated for an additional five hours. The work-up procedure used in Part F of Examples 125-135 was followed. The crude product was purified by column chromatography on silica gel (eluting with chloroform:CMA in a gradient from 100:0 to 80:20) and then triturated with methanol, isolated by filtration, and dried for 20 hours under high vacuum at 140° C. to provide 0.62 g of 4-methoxybenzyl 4-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]butane-1-sulfonamide as a beige powder, mp 230-231.5° C.

Aufarbeitung

  1. temperatureThe reaction was heated
  2. additionwas added
  3. temperaturethe reaction was heated for an additional five hours
  4. customThe crude product was purified by column chromatography on silica gel (
  5. washeluting with chloroform
  6. customCMA in a gradient from 100:0 to 80:20) and then triturated with methanol
  7. customisolated by filtration
  8. customdried for 20 hours under high vacuum at 140° C.

Quellen und Nachweise

ORD-Eintrag
ord-65bd41ad1ef64ca08d4aa3c3f68aed7b
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07598382B2

Verknüpfte Notizen

Wird geladen…