Diisopropylethylamine → HCID 24797797、化合物

HRID 1803928ノート

反応式

HRID 1803928 の反応式
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=2)[N:3]=1.CCN(C(C)C)C(C)C.[NH2:25][CH2:26][CH2:27][CH2:28][N:29]1[CH2:34][CH2:33][N:32]([C:35](=[O:37])[CH3:36])[CH2:31][CH2:30]1>C1COCC1>[Cl:15][C:11]1[CH:10]=[C:9]([NH:8][C:4]2[N:3]=[C:2]([NH:25][CH2:26][CH2:27][CH2:28][N:29]3[CH2:30][CH2:31][N:32]([C:35](=[O:37])[CH3:36])[CH2:33][CH2:34]3)[CH:7]=[CH:6][N:5]=2)[CH:14]=[CH:13][CH:12]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 167925911-(4-(3-Aminopropyl)piperazin-1-yl)ethanoneHCID 590282434-chloro-N-(3-chlorophenyl)pyrimidin-2-amine

生成物 1

HCID 24797797HCID 24797797、化合物収率 10%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To 4-chloro-N-(3-chlorophenyl)pyrimidin-2-amine (0.5 g, 2.09 mmol) in THF (13 mL) is added DIPEA (0.73 mL, 4.18 mmol) followed by 1-(4-(3-aminopropyl)-piperazin-1-yl)ethanone, 22, (0.77 g, 4.18 mmol). The resulting mixture is refluxed for 12 hours after which the reaction mixture is cooled to room temperature and the solvent removed in vacuo. To the resulting residue is added water (50 mL) and the solution is washed with EtOAc (3×100 mL). The combined organic layers are dried (MgSO4) and concentrated in vacuo. The residue which is obtained is purified over silica (10% MeOH in CH2Cl2) to afford 0.173 g (10% yield) of the desired compound. 1H NMR (DMSO-d6, 300 MHz) δ1.67-1.75 (m, 2H), 1.97 (s, 3H), 2.27-2.40 (m, 6H), 3.37-3.42 (m, 6H), 5.96 (d, J=6.0 Hz, 1H), 6.87 (d, J=8.1 Hz, 1H), 7.21 (t, J=8.1 Hz, 1H), 7.28 (bs, 1H), 7.58 (d, J=7.2 Hz, 1H), 7.80 (bs, 1H), 8.13 (bs, 1H), 9.19 (s, 1H). MS (ESI, pos. ion) m/z: 389 (M+1). HRMS calcd for C19H25ClN6O, 389.1857 m/z (M+H)+; observed 389.1851 m/z.

後処理

  1. temperatureThe resulting mixture is refluxed for 12 hours after which the reaction mixture
  2. customthe solvent removed in vacuo
  3. additionTo the resulting residue is added water (50 mL)
  4. washthe solution is washed with EtOAc (3×100 mL)
  5. dry with materialThe combined organic layers are dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue which is obtained
  8. customis purified over silica (10% MeOH in CH2Cl2)

出典と根拠

ORDレコード
ord-d63b3ff852064f49bf1dc941cb1fef9f
出典データセット
uspto-grants-2013_01
特許番号
US08354407B2

反応ノート

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