1-Piperazinecarboxaldehyde → HCID 11757976, compound

HRID 1785122Notes

Reaction equation

HRID 1785122 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([C:11]#[C:12][CH2:13][CH2:14][O:15][CH3:16])[C:5]2[O:6][CH2:7][O:8][C:4]=2[C:3]=1[NH:17][C:18]1[C:27]2[C:22](=[CH:23][C:24]([O:30][CH2:31][CH2:32][CH2:33]Cl)=[C:25]([O:28][CH3:29])[CH:26]=2)[N:21]=[CH:20][N:19]=1.[CH:35]([N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1)=[O:36]>COCCO>[Cl:1][C:2]1[CH:10]=[C:9]([C:11]#[C:12][CH2:13][CH2:14][O:15][CH3:16])[C:5]2[O:6][CH2:7][O:8][C:4]=2[C:3]=1[NH:17][C:18]1[C:27]2[C:22](=[CH:23][C:24]([O:30][CH2:31][CH2:32][CH2:33][N:40]3[CH2:41][CH2:42][N:37]([CH:35]=[O:36])[CH2:38][CH2:39]3)=[C:25]([O:28][CH3:29])[CH:26]=2)[N:21]=[CH:20][N:19]=1

Participants

4

Reactant 2

HCID 821911-PiperazinecarboxaldehydeHCID 68882290HCID 68882290, compound

Product 1

HCID 11757976HCID 11757976, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

This was prepared using the method described in example 13 using N-[5-chloro-7-(4-methoxybut-1-yn-1-yl)-1,3-benzodioxol-4-yl]-7-(3-chloropropoxy)-6-methoxyquinazolin-4-amine (200 mg, 0.40 mmol) and 1-formylpiperazine (226 mg, 1.98 mmol) in 2-methoxyethanol (4 ml). The crude product was purified by column chromatography on silica using increasing concentrations of methanol in dichloromethane as eluent. There was thus obtained the title compound (148 mg, 64%) as a pale brown solid; NMR Spectum:(DMSOd6) 1.96 (quintet, 2H), 2.36 (m, 2H), 2.41 (m, 2H), 2.50 (t, 2H), 2.71 (t, 2H), 3.31 (s, 3H), 3.39 (m, 4H), 3.52 (t, 2H), 3.93 (s, 3H), 4.20 (t, 2H), 6.14 (s, 2H), 7.07 (s, 1H), 7.20 (s, 1H), 7.82 (s, 1H), 8.00 (s, 1H), 8.32 (s, 1H), 9.48 (s, 1H); Mass Spectrum: M+H+ 582/584.

Workup

  1. customThis was prepared
  2. customThe crude product was purified by column chromatography on silica using
  3. temperatureincreasing concentrations of methanol in dichloromethane as eluent

Sources & evidence

ORD record
ord-386a9cd81d134e42be1324060dfa8a44
Source dataset
uspto-grants-2009_03
Patent number
US07504408B2

Reaction notes

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