Potassium Carbonate → Tert-butyl {4-[(3-amino-7-bromoquinolin-4-ylamino)methyl]benzyl}carbamate

HRID 9490

反応式

HRID 9490 の反応式
C(=O)([O-])[O-].[K+].[K+].S(S([O-])=O)([O-])=O.[Na+].[Na+].[C:15]([O:19][C:20](=[O:45])[NH:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][NH:30][C:31]2[C:40]3[C:35](=[CH:36][C:37]([Br:41])=[CH:38][CH:39]=3)[N:34]=[CH:33][C:32]=2[N+:42]([O-])=O)=[CH:25][CH:24]=1)([CH3:18])([CH3:17])[CH3:16]>O.ClCCl.CC[N+]1C=CC(C2C=C[N+](CC)=CC=2)=CC=1.[Br-].[Br-]>[C:15]([O:19][C:20](=[O:45])[NH:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][NH:30][C:31]2[C:40]3[C:35](=[CH:36][C:37]([Br:41])=[CH:38][CH:39]=3)[N:34]=[CH:33][C:32]=2[NH2:42])=[CH:25][CH:24]=1)([CH3:18])([CH3:16])[CH3:17]

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 24489Sodium DithioniteHCID 21984421Tert-butyl {4-[(7-bromo-3-nitroquinolin-4-ylamino)methyl]benzyl}carbamate

生成物 1

HCID 21984367Tert-butyl {4-[(3-amino-7-bromoquinolin-4-ylamino)methyl]benzyl}carbamate収率 100.5%

試薬・触媒・溶媒 3

HCID 114742621,1'-Diethyl-4,4'-bipyridinium dibromide触媒HCID 962Water溶媒3 回HCID 6344Dichloromethane溶媒2 回

実験手順

Ethyl viologen dibromide (0.069 g, 0.18 mmol), potassium carbonate (12.76 g, 92 mmol) in water (55mL), and sodium hydrosulfite (11.25 g, 65 mmol) in water (55mL) were added sequentially to a solution of tert-butyl{4-[(7-bromo-3-nitroquinolin-4-ylamino)methyl]benzyl}carbamate (9.0 g, 18.5 mmol) in dichloromethane (110 mL). The resulting biphasic mixture was stirred for 20 hours. The reaction was diluted with water (600 mL) and dichloromethane (500 mL). The layers were separated and the aqueous fraction was extracted with dichloromethane. The organic fractions were combined and washed sequentially with water and saturated aqueous sodium chloride. The organic fraction was dried over sodium sulfate, filtered, and concentrated under reduced pressure to yield 8.5 g of tert-butyl{4-[(3-amino-7-bromoquinolin-4-ylamino)methyl]benzyl}carbamate as a yellow-brown amorphous solid.

後処理

  1. customThe layers were separated
  2. extractionthe aqueous fraction was extracted with dichloromethane
  3. washwashed sequentially with water and saturated aqueous sodium chloride
  4. dry with materialThe organic fraction was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-e14b4f690e7d423e92497dc07775b581
出典データセット
uspto-grants-2006_08
特許番号
US07091214B2

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