Triethylamine → N-[3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]-5-(dimethylamino)naphthalene-1-sulfonamide

HRID 2180290Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2180290
C(N(CC)CC)C.[NH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:24]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:17]=[C:16]([NH2:25])[C:15]=2[N:14]=[C:13]1[CH2:26][CH2:27][CH2:28][CH3:29].[CH3:30][N:31]([CH3:46])[C:32]1[CH:41]=[CH:40][CH:39]=[C:38]2[C:33]=1[CH:34]=[CH:35][CH:36]=[C:37]2[S:42](Cl)(=[O:44])=[O:43].C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O.O>[NH2:25][C:16]1[C:15]2[N:14]=[C:13]([CH2:26][CH2:27][CH2:28][CH3:29])[N:12]([CH2:11][CH2:10][CH2:9][NH:8][S:42]([C:37]3[C:38]4[C:33](=[C:32]([N:31]([CH3:46])[CH3:30])[CH:41]=[CH:40][CH:39]=4)[CH:34]=[CH:35][CH:36]=3)(=[O:44])=[O:43])[C:24]=2[C:23]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N:17]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 11801Dansyl chlorideHCID 223444131-(3-aminopropyl)-2-butyl-1H-imidazo[4,5-c]quinolin-4-amine

Produkt 1

HCID 10459670N-[3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]-5-(dimethylamino)naphthalene-1-sulfonamideAusbeute 65,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel2×

Versuchsvorschrift

Under a nitrogen atmosphere triethylamine (765 mg, 7.56 mmol) was added to a solution of 1-(3-aminopropyl)-2-butyl-1H-imidazo[4,5-c]quinolin-4-amine (1.5 g, 5.04 mmol) in 1-methyl-2-pyrrolidinone (75 mL). A solution of 5-dimethylamino-1-naphthalenesulfonyl chloride (1.5 g, 5.55 mmol) in 1-methyl-2-pyrrolidinone was added. The reaction was monitored by HPLC. The reaction mixture was combined with water (500 mL) and the pH was adjusted to 10 with solid potassium carbonate. The resulting yellow precipitate was isolated by filtration, rinsed with water and then purified by column chromatography (silica gel eluting with 1-5% methanol in chloroform). The purified material was recrystallized from acetonitrile to provide 1.76 g of N-[3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]-5-(dimethylamino)naphthalene-1-sulfonamide as a solid, m.p. 216.5-217.5° C. Analysis: Calculated for C29H34N6O2S: % C, 65.64; % H, 6.46; % N, 15.84; Found: % C, 65.52; % H, 6.44; % N, 15.90.

Aufarbeitung

  1. customThe resulting yellow precipitate was isolated by filtration
  2. washrinsed with water
  3. custompurified by column chromatography (silica gel eluting with 1-5% methanol in chloroform)
  4. customThe purified material was recrystallized from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-a9ea08fbdd6a4e668a35066b93f14558
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06888000B2

Notizen zur Reaktion

Wird geladen…