Dimethylformamide → (6,4'-Dimethoxy-biphenyl-3-ylmethyl)-(1-quinolin-8-yl-ethyl)-amine

HRID 460146Notes

Reaction equation

HRID 460146 reaction equation
[C:1]1(=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11](O)=O)[NH:2]1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)[C:26]2[N:27]=[CH:28][CH:29]=[CH:30][C:25]=2N=N1.Cl.CN[O:42][CH3:43].CN(C)[CH:46]=[O:47]>>[CH3:46][O:47][C:7]1[C:8]([C:5]2[CH:10]=[CH:9][C:8]([O:42][CH3:43])=[CH:7][CH:6]=2)=[CH:9][C:10]([CH2:1][NH:2][CH:3]([C:11]2[CH:4]=[CH:3][CH:11]=[C:25]3[C:26]=2[N:27]=[CH:28][CH:29]=[CH:30]3)[CH3:4])=[CH:5][CH:6]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 2800011-Oxo-1,2-dihydroisoquinoline-3-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 22391354(6,4'-Dimethoxy-biphenyl-3-ylmethyl)-(1-quinolin-8-yl-ethyl)-amine

Procedure

To the solution of 1-isoquinolonecarboxylic acid (1.73 g, 10 mmol, Aldrich) in anhydrous N,N-dimethylformamide (30 mL) were added N,N-diisopropylethylaime (5.29 g, 40 mmol, Aldrich), O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (7.6 g, 20 mmol, PerSeptive Biosystems GmbH), N,O-dimethylhyroxylamine hydrochloride (1.8 g, 20 mmol, Aldrich) subsequently at room temperature. The reaction solution was allowed to stir for overnight at room temperature. The N,N-Dimethylformamide was removed via vacuo and the resulting residue was diluted in ethyl acetate (50 mL). After being was washed by saturate aqueous sodium bicarbonate (50 mL) and brine (50 mL), the organic portion was dried over anhydrous magnesium sulfate and concentrated. The title compound was purified by column chromatography (silica gel, ethyl acetate) in form as yellow syrup in 94% yield (2.04 g, 9.4 mmol).

Workup

  1. customThe N,N-Dimethylformamide was removed via vacuo
  2. additionthe resulting residue was diluted in ethyl acetate (50 mL)
  3. washAfter being was washed
  4. concentrationby saturate aqueous sodium bicarbonate (50 mL) and brine (50 mL)
  5. dry with materialthe organic portion was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe title compound was purified by column chromatography (silica gel, ethyl acetate) in form as yellow syrup in 94% yield (2.04 g, 9.4 mmol)

Sources & evidence

ORD record
ord-d34b694d6cac45c7ada7cab39a3404ba
Source dataset
uspto-grants-2007_03
Patent number
US07196102B2

Reaction notes

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