tert-Butyl 4-(4-aminophenyl)piperazine-1-carboxylate → 4-{-4-[5-Bromo-4-(cyclohexyl-phenyl-amino)-pyrimidin-2-ylamino]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester

HRID 875946ノート

反応式

HRID 875946 の反応式
[Br:1][C:2]1[C:3]([N:9]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:4][C:5](Cl)=[N:6][CH:7]=1.[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][N:32]([C:35]2[CH:40]=[CH:39][C:38]([NH2:41])=[CH:37][CH:36]=2)[CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23]>O1CCOCC1.C(OCC)(=O)C>[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][N:32]([C:35]2[CH:36]=[CH:37][C:38]([NH:41][C:5]3[N:4]=[C:3]([N:9]([CH:16]4[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]4)[C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=4)[C:2]([Br:1])=[CH:7][N:6]=3)=[CH:39][CH:40]=2)[CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:23])[CH3:24]

参加物

5

反応物 2

HCID 11011301tert-Butyl 4-(4-aminophenyl)piperazine-1-carboxylateHCID 58299589(5-Bromo-2-chloro-pyrimidin-4-yl)-cyclohexyl-phenyl-amine

生成物 1

HCID 672353454-{-4-[5-Bromo-4-(cyclohexyl-phenyl-amino)-pyrimidin-2-ylamino]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester収率 33%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

Compound 37 (0.42 g, 1.15 mmol) and 4-(4-amino-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (0.64 g, 2.30 mmol) were dissolved in dioxane (2 mL), and this mixture was heated at 100° C. for 24 hours. The reaction was cooled to room temperature and diluted with ethyl acetate. This mixture was washed with water and brine. The organic layer was dried with sodium sulfate and purified by flash chromatography (ethyl acetate/hexane) to give compound 38 as a yellow solid (0.23 g, 33%). 1H NMR (500 MHz, DMSO-d6) δ ppm 9.18 (1 H, s), 7.97 (1 H, s), 7.55 (2 H, d, J=10 Hz), 7.37 (2 H, m), 7.31 (1 H, m), 7.12 (2 H, m), 6.89 (2 H, d, J=10 Hz), 4.68 (1 H, m), 3.44 (4 H, m), 3.00 (4 H, m), 1.91 (2 H, d, J=10 Hz), 1.72 (2 H, d, J=10 Hz), 1.57 (1 H, d, J=10 Hz), 1.41 (9 H, s), 1.35 (2 H, m), 1.14 (2 H, m), 0.92 (1 H, m); LCMS-ESI (POS), M/Z, M+1: Found 609.2, Calculated 607.2/609.2.

後処理

  1. temperatureThe reaction was cooled to room temperature
  2. washThis mixture was washed with water and brine
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. custompurified by flash chromatography (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-2926333a45894bf986b9876534fe27cf
出典データセット
uspto-grants-2015_03
特許番号
US08980903B2

反応ノート

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