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

HRID 416813ノート

反応式

HRID 416813 の反応式
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

参加物

7

反応物 3

HCID 81531DiisopropylethylamineHCID 46867019HCID 46867019、化合物HCID 468676602-Amino-4,5-dichloro-3-nitropyridine

生成物 1

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

試薬・触媒・溶媒 3

HCID 3776Isopropanol溶媒2 回HCID 6344Dichloromethane溶媒HCID 6422Trifluoroacetic acid溶媒

反応条件

温度
45 °C

実験手順

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);

後処理

  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%)

出典と根拠

ORDレコード
ord-18283aca5b754ad8beb306ac47341f71
出典データセット
uspto-grants-2012_01
特許番号
US08088761B2

反応ノート

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