Triethylamine → HCID 68882463, compound

HRID 1785154Notes

Reaction equation

HRID 1785154 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11]([NH:17][C:18]3[C:26]4[O:25][CH2:24][O:23][C:22]=4[C:21]([C:27]#[C:28][CH2:29][O:30][CH3:31])=[CH:20][C:19]=3[Cl:32])=[N:12][CH:13]=[N:14]2)=[CH:9][C:8]=1[O:33][CH3:34].C(N(CC)CC)C.[C:42]([N:45]1[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]1)(=[O:44])[CH3:43].COC(O)C>>[C:42]([N:45]1[CH2:50][CH2:49][N:48]([CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]2[CH:16]=[C:15]3[C:10]([C:11]([NH:17][C:18]4[C:26]5[O:25][CH2:24][O:23][C:22]=5[C:21]([C:27]#[C:28][CH2:29][O:30][CH3:31])=[CH:20][C:19]=4[Cl:32])=[N:12][CH:13]=[N:14]3)=[CH:9][C:8]=2[O:33][CH3:34])[CH2:47][CH2:46]1)(=[O:44])[CH3:43]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 837951-AcetylpiperazineHCID 30156371-MethoxyethanolHCID 68881822HCID 68881822, compound

Product 1

HCID 68882463HCID 68882463, compoundYield 17.2%

Procedure

A mixture of 7-(4-chlorobutoxy)-N-[5-chloro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-yl]-6-methoxyquinazolin-4-amine (0.23 g, 0.4 mmol), triethylamine (0.22 ml, 1.6 mmol), N-acetyl piperazine (0.205 g, 1.6 mmol) in 2 methoxyethanol (2 ml) was heated to 80 C for 12 hours and then at 100 C for 7 hours. The solvent was evaporated under reduced pressure and the residue was partitioned between ethyl acetate and water. The organic layer was separated, dried over magnesium sulfate and evaporated under reduced pressure. Flash chromatography on silica eluting with a mixture of 2-10% methanol in dichloromethane gave the product as a light orange solid (0.041 g, 17%). NMR Spectrum: (DMSOd6 at 373k+d4 acetic acid) 1.73 (m, 2H), 1.88 (m, 2H), 1.98 (s, 3H), 2.67 (t, 4H), 3.09 (t, 2H), 3.37 (s, 3H), 3.55 (t, 4H), 3.96 (s, 3H), 4.18 (t, 2H), 4.32 (s, 2H), 6.09 (s, 2H), 7.05 (s, 1H), 7.21 (s, 1H), 7.80 (s, 1H), 8.25 (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 evaporated under reduced pressure
  3. customthe residue was partitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. additionFlash chromatography on silica eluting with a mixture of 2-10% methanol in dichloromethane

Sources & evidence

ORD record
ord-2c20b06201a341cb95c1c560d9998edb
Source dataset
uspto-grants-2009_03
Patent number
US07504408B2

Reaction notes

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