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

HRID 9489

반응식

HRID 9489 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e290789573584e50a29ba8fd5e830722
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091214B2

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