Triethylamine → HCID 10008660, compound

HRID 1785163Notes

Reaction equation

HRID 1785163 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([C:11]#[C:12][CH2:13][O:14][CH:15]([CH3:17])[CH3:16])[C:5]2[O:6][CH2:7][O:8][C:4]=2[C:3]=1[NH:18][C:19]1[C:28]2[C:23](=[CH:24][C:25]([O:31][CH2:32][CH2:33][CH2:34]Cl)=[C:26]([O:29][CH3:30])[CH:27]=2)[N:22]=[CH:21][N:20]=1.C(N(CC)CC)C.[CH3:43][N:44]1[CH2:49][CH2:48][NH:47][CH2:46][C:45]1=[O:50]>COCCO>[Cl:1][C:2]1[CH:10]=[C:9]([C:11]#[C:12][CH2:13][O:14][CH:15]([CH3:17])[CH3:16])[C:5]2[O:6][CH2:7][O:8][C:4]=2[C:3]=1[NH:18][C:19]1[C:28]2[C:23](=[CH:24][C:25]([O:31][CH2:32][CH2:33][CH2:34][N:47]3[CH2:48][CH2:49][N:44]([CH3:43])[C:45](=[O:50])[CH2:46]3)=[C:26]([O:29][CH3:30])[CH:27]=2)[N:22]=[CH:21][N:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 43990421-Methylpiperazin-2-oneHCID 68880555HCID 68880555, compound

Product 1

HCID 10008660HCID 10008660, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A mixture of N-[5-chloro-7-(3-isopropoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-yl]-7-(3-chloropropoxy)-6-methoxyquinazolin-4-amine (0.22 g, 0.43 mmol), triethylamine (0.29 ml, 2.13 mmol), 1-methylpiperazin-2-one (0.24 g, 2.13 mmol) in 2-methoxyethanol (3 ml) was heated to 80 C for 12 hours and then at 100 C for 7 hours. The solvent was removed under reduced pressure and the residue was partitioned between dichloromethane and water. The organic layer was separated, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by flash chromatography on silica eluting with a mixture of 2-8% methanol in dichloromethane to give the product as an light orange solid (0.129 g, 51%). NMR Spectrum: (DMSOd6) 1.18 (d, 6H), 1.98 (m, 2H), 2.52 (t, 2H under DMSO), 2.72 (t, 2H), 2.88 (s, 3H), 3.04 (s, 2H), 3.34 (t, 2H under H2O), 3.83 (m, 1H), 3.97 (s, 3H), 4.22 (t, 2H), 4.42 (s, 2H), 6.17 (s, 2H), 7.15 (s, 1H), 7.21 (s, 1H), 7.83 (s, 1H), 8.34 (s, 1H), 9.52 (s, 1H). Mass Spectrum: M+H+ 596 and M+H− 594.

Workup

  1. temperaturewas heated to 80 C for 12 hours
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was partitioned between dichloromethane and water
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica eluting with a mixture of 2-8% methanol in dichloromethane

Sources & evidence

ORD record
ord-d394345ceffc4175918a2082bca6edb8
Source dataset
uspto-grants-2009_03
Patent number
US07504408B2

Reaction notes

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