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

HRID 9387

反応式

HRID 9387 の反応式
S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+].[C:15]([O:19][C:20](=[O:41])[NH:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27]1[C:36]2[C:31](=[CH:32][C:33]([Br:37])=[CH:34][CH:35]=2)[N:30]=[CH:29][C:28]=1[N+:38]([O-])=O)([CH3:18])([CH3:17])[CH3:16]>O.ClCCl.[Br-].[Br-].C([N+]1C=CC(C2C=C[N+](CC)=CC=2)=CC=1)C>[C:15]([O:19][C:20](=[O:41])[NH:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27]1[C:36]2[C:31](=[CH:32][C:33]([Br:37])=[CH:34][CH:35]=2)[N:30]=[CH:29][C:28]=1[NH2:38])([CH3:18])([CH3:16])[CH3:17]

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 24489Sodium DithioniteHCID 21984414Tert-butyl [4-(7-bromo-3-nitroquinolin-4-ylamino)butyl]carbamate

生成物 1

HCID 21984174Tert-butyl [4-(3-amino-7-bromoquinolin-4-ylamino)butyl]carbamate収率 99%

試薬・触媒・溶媒 3

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

実験手順

A solution of sodium hydrosulfite (43.35 g, 249 mmol) and potassium carbonate (38.28 g, 277 mmol) in water (300 mL) was added to a mixture of tert-butyl[4-(7-bromo-3-nitroquinolin-4-ylamino)butyl]carbamate (24.3 g, 55.3 mmol) and 1,1′-diethyl-4,4′-bipyridinium dibromide (1.03 g, 2.76 mmol) in dichloromethane (368 mL) and water (40 mL), and the reaction was stirred overnight at ambient temperature. The reaction mixture was filtered through a layer of CELITE filter aid. The aqueous filtrate was extracted with dichloromethane, and the combined organic fractions were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 22.4 g of tert-butyl[4-(3-amino-7-bromoquinolin-4-ylamino)butyl]carbamate as a brown powder.

後処理

  1. filtrationThe reaction mixture was filtered through a layer of CELITE
  2. filtrationfilter aid
  3. extractionThe aqueous filtrate was extracted with dichloromethane
  4. dry with materialthe combined organic fractions were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-ab593658aea3483d87d1ad57cc97e475
出典データセット
uspto-grants-2006_08
特許番号
US07091214B2

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