1-Acetylpiperazine → HCID 68881623, compound

HRID 1785109Notes

Reaction equation

HRID 1785109 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.[C:35]([N:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1)(=[O:37])[CH3:36]>COCCO>[C:35]([N:38]1[CH2:43][CH2:42][N:41]([CH2:33][CH2:32][CH2:31][O:30][C:24]2[CH:23]=[C:22]3[C:27]([C:18]([NH:17][C:3]4[C:4]5[O:8][CH2:7][O:6][C:5]=5[C:9]([C:11]#[C:12][CH2:13][CH2:14][O:15][CH3:16])=[CH:10][C:2]=4[Cl:1])=[N:19][CH:20]=[N:21]3)=[CH:26][C:25]=2[O:28][CH3:29])[CH2:40][CH2:39]1)(=[O:37])[CH3:36]

Participants

4

Reactant 2

HCID 837951-AcetylpiperazineHCID 68882290HCID 68882290, compound

Product 1

HCID 68881623HCID 68881623, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

N-[5-Chloro-7-(4-methoxybut-1-yn-1-yl)-1,3-benzodioxol-4-yl]-7-(3-chloropropoxy)-6-methoxyquinazolin-4-amine (192 mg, 0.38 mmol) and 1-acetylpiperazine (244 mg, 1.9 mmol) in 2-methoxyethanol (4 ml) were stirred and heated at 100° for 12 hr. then quenched in water and extracted with dichloromethane. The combined extracts were washed with saturated brine, dried over magnesium sulphate and evaporated to an orange oil. This was then purified by column chromatography on silica using increasing concentrations of methanol in dichloromethane as eluent. There was thus obtained the title compound (187 mg, 82%) as a pale yellow solid; NMR Spectrum:(DMSOd6) 1.98 (quintet, 2H), 1.99 (s, 3H), 2.33 (m, 2H), 2.40 (m, 2H), 2.48 (t, 2H), 2.72 (t, 2H), 3.31 (s, 3H), 3.43 (m, 4H), 3.53 (t, 2H), 3.93 (s, 3H), 4.21 (t, 2H), 6.13 (s, 2H), 7.07 (s, 1H), 7.18 (s, 1H), 7.81 (s, 1H), 8.32 (s, 1H), 9.50 (s, 1H); Mass Spectrum: M+H+ 596/598.

Workup

  1. temperatureheated at 100° for 12 hr
  2. customthen quenched in water
  3. extractionextracted with dichloromethane
  4. washThe combined extracts were washed with saturated brine
  5. dry with materialdried over magnesium sulphate
  6. customevaporated to an orange oil
  7. customThis was then purified by column chromatography on silica using
  8. temperatureincreasing concentrations of methanol in dichloromethane as eluent

Sources & evidence

ORD record
ord-6491e3b2764442018e042adba2734313
Source dataset
uspto-grants-2009_03
Patent number
US07504408B2

Reaction notes

Loading…