Triethylamine → HCID 25018891, compound

HRID 1878711Notes

Reaction equation

HRID 1878711 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.[O:14]=[C:15]1[CH:20]=[CH:19][C:18]([C:21]2[S:22][CH:23]=[CH:24][CH:25]=2)=[CH:17][N:16]1[CH2:26][C:27](O)=[O:28].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>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([NH:13][C:27](=[O:28])[CH2:26][N:16]3[CH:17]=[C:18]([C:21]4[S:22][CH:23]=[CH:24][CH:25]=4)[CH:19]=[CH:20][C:15]3=[O:14])=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=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 170398707-Methoxyquinolin-4-amineHCID 69232126HCID 69232126, compound

Product 1

HCID 25018891HCID 25018891, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 7-methoxyquinolin-4-amine (0.13 g, 0.77 mmol) and 2-(2-oxo-5-(thiophen-2-yl)pyridin-1(2H)-yl)acetic acid (0.15 g, 0.64 mmol) in 5 mL of DMF at rt was added triethylamine (0.13 ml, 0.96 mmol) followed by HATU (0.44 g, 1.1 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 (aq.) 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 white (0.10 g, 40% yield). MS (ESI pos. ion) m/z (MH+): 392.1. Calc'd Exact Mass for C21H17N3O3S: 391.1.

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)
  7. customto give white (0.10 g, 40% yield)

Sources & evidence

ORD record
ord-8068c09aeffa4a9ca24a751cb3432bbf
Source dataset
uspto-grants-2012_11
Patent number
US08314087B2

Reaction notes

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