Diisopropylethylamine → HCID 24797797, compound

HRID 1803928Notes

Reaction equation

HRID 1803928 reaction equation
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

Participants

5

Reactant 3

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

Product 1

HCID 24797797HCID 24797797, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-d63b3ff852064f49bf1dc941cb1fef9f
Source dataset
uspto-grants-2013_01
Patent number
US08354407B2

Reaction notes

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