Diisopropylethylamine → N-(3-(3-oxo-3,4-dihydropyrido[2,3-b]pyrazin-8-yloxy)phenyl)-3-(trifluoro-methoxy)benzamide

HRID 1403052Notes

Reaction equation

HRID 1403052 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[O:5][C:6]1[C:15]2[N:14]=[CH:13][C:12](=[O:16])[NH:11][C:10]=2[N:9]=[CH:8][CH:7]=1.C(N(C(C)C)CC)(C)C.[F:29][C:30]([F:42])([F:41])[O:31][C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][CH:40]=1)[C:35](Cl)=[O:36]>C1COCC1>[O:16]=[C:12]1[NH:11][C:10]2[N:9]=[CH:8][CH:7]=[C:6]([O:5][C:4]3[CH:3]=[C:2]([NH:1][C:35](=[O:36])[C:34]4[CH:38]=[CH:39][CH:40]=[C:32]([O:31][C:30]([F:29])([F:41])[F:42])[CH:33]=4)[CH:19]=[CH:18][CH:17]=3)[C:15]=2[N:14]=[CH:13]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5228543-(Trifluoromethoxy)benzoyl chlorideHCID 469015938-(3-aminophenoxy)pyrido[2,3-b]pyrazin-3(4H)-one

Product 1

HCID 44133722N-(3-(3-oxo-3,4-dihydropyrido[2,3-b]pyrazin-8-yloxy)phenyl)-3-(trifluoro-methoxy)benzamideYield 60.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Method G1: 8-(3-aminophenoxy)pyrido[2,3-b]pyrazin-3(4H)-one (43 mg, 0.169 mmol) and diisopropylethylamine (44 μL, 0.254 mmol) were mixed in dry THF (5.0 mL) and 3-trifluoromethoxybenzoyl chloride (57 mg, 0.254 mmol) was added. This mixture was heated to reflux for 17 h. After cooling at RT, the solvent was removed in vacuo. The obtained oily residue was dissolved in DCM and washed with water and dried over MgSO4. After evaporation of DCM, the residue was retaken in Et2O, triturated and filtered off to afford the title compound as a white solid (45 mg, 60%).

Workup

  1. temperatureThis mixture was heated
  2. temperatureto reflux for 17 h
  3. customthe solvent was removed in vacuo
  4. dissolutionThe obtained oily residue was dissolved in DCM
  5. washwashed with water
  6. dry with materialdried over MgSO4
  7. customAfter evaporation of DCM
  8. customtriturated
  9. filtrationfiltered off

Sources & evidence

ORD record
ord-fab4da9dee8e41ff8155b2a4426776c4
Source dataset
uspto-grants-2014_12
Patent number
US08912191B2

Reaction notes

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