Diisopropylethylamine → 5-Bromo-4-[4-(5-methyl-isoxazol-3-ylmethyl)-piperazin-1-yl]-3-nitro-pyridin-2-ylamine

HRID 416805노트

반응식

HRID 416805 반응식
C(O[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:19]=[C:18]([CH3:20])[O:17][N:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[NH2:21][C:22]1[C:27]([N+:28]([O-:30])=[O:29])=C(Cl)[C:25]([Br:32])=[CH:24][N:23]=1.C(N(C(C)C)CC)(C)C>ClCCl.C(O)(C(F)(F)F)=O.C(O)(C)C>[Br:32][C:25]1[C:6]([N:8]2[CH2:9][CH2:10][N:11]([CH2:14][C:15]3[CH:19]=[C:18]([CH3:20])[O:17][N:16]=3)[CH2:12][CH2:13]2)=[C:27]([N+:28]([O-:30])=[O:29])[C:22]([NH2:21])=[N:23][CH:24]=1

참가 물질

7

반응물 3

HCID 81531DiisopropylethylamineHCID 454802365-Bromo-4-chloro-3-nitropyridin-2-amineHCID 46867019HCID 46867019, 화합물

생성물 1

HCID 468687835-Bromo-4-[4-(5-methyl-isoxazol-3-ylmethyl)-piperazin-1-yl]-3-nitro-pyridin-2-ylamine

시약·촉매·용매 3

HCID 3776Isopropanol용매2회HCID 6344Dichloromethane용매HCID 6422Trifluoroacetic acid용매

반응 조건

온도
45 °C

실험 절차

A solution of 4-(5-methyl-isoxazol-3-ylmethyl)-piperazine-1-carboxylic acid tert-butyl ester (0.200 g, 0.71 mmol) in dichloromethane (6 ml) and TFA (8 ml) was stirred at room temperature for 2 h then concentrated in vacuo, and the resulting residue was dried in vacuo. This material (supposedly 0.70 mmol) was dissolved in isopropanol (13 ml) and to this solution 2-amino-5-bromo-4-chloro-3-nitropyridine (0.157 g, 0.63 mmol) was added followed by diisopropylethylamine (0.65 ml, 3.70 mmol). The reaction mixture was stirred at 45° C. for 20 h, then allowed to cool to room temperature and diluted with isopropanol (5 ml). The resulting orange solid was collected by filtration, washed with isopropanol (2×5 ml), diethyl ether (3×5 ml), and dried (0.170 g, 60%); 1H-NMR (500 MHz, DMSO-d6) 2.38 (s, 3H, isoxazole 5-CH3), 2.53 (br s, 4H, piperazine N(CH2)2), 3.05 (br s, 4H, piperazine N(CH2)2), 3.55 (s, 2H, NCH2 isoxazole), 6.21 (s, 1H, isoxazole 4-H), 6.97 (s, 2H, NH2), 8.16 (s, 1H, pyridine 6-H);

후처리

  1. concentrationthen concentrated in vacuo
  2. customthe resulting residue was dried in vacuo
  3. additionwas added
  4. temperatureto cool to room temperature
  5. filtrationThe resulting orange solid was collected by filtration
  6. washwashed with isopropanol (2×5 ml), diethyl ether (3×5 ml)
  7. customdried (0.170 g, 60%)

출처 및 근거

ORD 기록
ord-fd92bc2e87a14bfca6ad08282a5f2a63
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088761B2

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