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

HRID 2180290ノート

反応式

HRID 2180290 の反応式
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

参加物

7

反応物 4

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

生成物 1

HCID 10459670N-[3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]-5-(dimethylamino)naphthalene-1-sulfonamide収率 65.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 13387N-methyl-2-pyrrolidone溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a9ea08fbdd6a4e668a35066b93f14558
出典データセット
uspto-grants-2005_05
特許番号
US06888000B2

反応ノート

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