Triethylamine → Tert-butyl {4-[(7-bromo-3-nitroquinolin-4-ylamino)methyl]benzyl}carbamate

HRID 9489

反応式

HRID 9489 の反応式
[C:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][NH2:17])=[CH:12][CH:11]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Br:18][C:19]1[CH:28]=[C:27]2[C:22]([C:23](Cl)=[C:24]([N+:29]([O-:31])=[O:30])[CH:25]=[N:26]2)=[CH:21][CH:20]=1.C(N(CC)CC)C>ClCCl>[C:4]([O:3][C:1](=[O:2])[NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][NH:17][C:23]2[C:22]3[C:27](=[CH:28][C:19]([Br:18])=[CH:20][CH:21]=3)[N:26]=[CH:25][C:24]=2[N+:29]([O-:31])=[O:30])=[CH:12][CH:11]=1)([CH3:7])([CH3:6])[CH3:5]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 3354775tert-butyl N-{[4-(aminomethyl)phenyl]methyl}carbamateHCID 219843617-Bromo-4-chloro-3-nitroquinoline

生成物 1

HCID 21984421Tert-butyl {4-[(7-bromo-3-nitroquinolin-4-ylamino)methyl]benzyl}carbamate収率 93.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

1-(N-BOC-aminomethyl)-4-(aminomethyl)benzene (5.0 g, 21 mmol) in dichloromethane (50 mL) was added dropwise to a mixture of 7-bromo-4-chloro-3-nitroquinoline (5.81 g, 20 mmol) and triethylamine (5.63 mL) in dichloromethane (60 mL). The reaction was stirred for 16 hours and then washed sequentially with water and saturated aqueous sodium chloride. The organic fraction was dried over sodium sulfate, filtered and concentrated to provide a yellow crystalline solid. Recrystallization from 2-propanol yielded 9.1 g of tert-butyl{4-[(7-bromo-3-nitroquinolin-4-ylamino)methyl]benzyl}carbamate as a yellow powder.

後処理

  1. washwashed sequentially with water and saturated aqueous sodium chloride
  2. dry with materialThe organic fraction was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto provide a yellow crystalline solid
  6. customRecrystallization from 2-propanol

出典と根拠

ORDレコード
ord-e290789573584e50a29ba8fd5e830722
出典データセット
uspto-grants-2006_08
特許番号
US07091214B2

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