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

HRID 416813노트

반응식

HRID 416813 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]([Cl: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>[Cl: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 46867019HCID 46867019, 화합물HCID 468676602-Amino-4,5-dichloro-3-nitropyridine

생성물 1

HCID 578973065-Chloro-4-[4-(5-methyl-isoxazol-3-ylmethyl)-piperazin-1-yl]-3-nitro-pyridin-2-ylamine

시약·촉매·용매 3

HCID 3776Isopropanol용매2회HCID 6344Dichloromethane용매HCID 6422Trifluoroacetic acid용매

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온도
45 °C

실험 절차

A solution of 4-(5-methyl-isoxazol-3-ylmethyl)-piperazine-1-carboxylic acid tert-butyl ester (0.126 g, 0.45 mmol) in dichloromethane (3.7 ml) and TFA (5 ml) was stirred at room temperature for 1.5 h then concentrated in vacuo, and the resulting residue was dried in vacuo. Part of this material (estimated 0.15 mmol) was dissolved in isopropanol (3 ml) and to this solution 2-amino-4,5-dichloro-3-nitropyridine (0.031 g, 0.15 mmol) was added followed by diisopropylethylamine (0.15 ml, 0.80 mmol). The reaction mixture was stirred at 45° C. for 20 h, then allowed to cool to room temperature and diluted with isopropanol (3 ml). The resulting yellow precipitate was collected by filtration, washed with isopropanol (2×3 ml), diethyl ether (2×3 ml), and dried (0.038 g, 73%); 1H-NMR (500 MHz, DMSO-d6) 2.38 (s, 3H, isoxazole 5-CH3), 2.52 (br s 4H, piperazine N(CH2)2), 3.06 (br t, J=4.1 Hz, 4H, piperazine N(CH2)2), 3.56 (s, 2H, NCH2 isoxale), 6.21 (s, 1H, isoxazole 4-H), 6.96 (s, 2H, NH2), 8.06 (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 yellow precipitate was collected by filtration
  6. washwashed with isopropanol (2×3 ml), diethyl ether (2×3 ml)
  7. customdried (0.038 g, 73%)

출처 및 근거

ORD 기록
ord-18283aca5b754ad8beb306ac47341f71
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088761B2

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