Triethylamine → HCID 25018892, compound

HRID 1878712Notes

Reaction equation

HRID 1878712 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([NH2:13])=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.[Br:14][C:15]1[CH:16]=[CH:17][C:18](=[O:25])[N:19]([CH2:21][C:22](O)=[O:23])[CH:20]=1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C([O-])(O)=O.[Na+]>CN(C=O)C.CCOC(C)=O>[Br:14][C:15]1[CH:16]=[CH:17][C:18](=[O:25])[N:19]([CH2:21][C:22]([NH:13][C:7]2[C:6]3[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[N:10]=[CH:9][CH:8]=2)=[O:23])[CH:20]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 167788012-(5-Bromo-2-oxopyridin-1(2H)-yl)acetic acidHCID 170398707-Methoxyquinolin-4-amine

Product 1

HCID 25018892HCID 25018892, compoundYield 12.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 7-methoxyquinolin-4-amine (0.275 g, 2 mmol) and 2-(5-bromo-2-oxopyridin-1(2H)-yl)acetic acid (0.273 g, 1 mmol) in 5 mL of DMF at rt was added triethylamine (0.2 ml, 2 mmol) followed by HATU (0.7 g, 2 mmol) solid. The reaction was then heated up to 40° C. for 8 hours and was cooled to rt and diluted with 60 mL of EtOAc and 30 mL of satd. NaHCO3 solution. The organic phase was separated, washed with 30 mL of brine and dried over Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (EtOAc to 10% MeOH/EtOAc) to give a white solid (0.05 g, 11% yield). MS (ESI pos. ion) m/z (MH+): 388.0. Calc'd Exact Mass for C17H14BrN3O3: 387.02.

Workup

  1. temperaturewas cooled to rt
  2. customThe organic phase was separated
  3. washwashed with 30 mL of brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by a silica gel column chromatography (EtOAc to 10% MeOH/EtOAc)

Sources & evidence

ORD record
ord-1d056b744fa448988d359847e6bcceb4
Source dataset
uspto-grants-2012_11
Patent number
US08314087B2

Reaction notes

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