2,5-Dimethoxybenzenemethanamine → HCID 86606904, compound

HRID 1364546Notes

Reaction equation

HRID 1364546 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][CH:3]=1.[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:14]=1[CH2:15][NH2:16].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)C(C)C)(C)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:14]=1[CH2:15][NH:16][C:8]([C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([Br:1])[N:7]=1)=[O:10]

Participants

7

Reactant 5

HCID 186522,5-DimethoxybenzenemethanamineHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 5939196-Bromopyridine-2-carboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 86606904HCID 86606904, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 6-bromopicolinic acid (1.01 g, 5.0 mmol) and 2,5-dimethoxybenzylamine (753 μL, 5.0 mmol) in DMF (10 mL) was added TBTU (1.77 g, 5.5 mmol), followed by N,N-diisopropylethylamine (871 μL, 5.0 mmol). The mixture was stirred at room temperature for 2 hours. After addition of saturated NaHCO3, the mixture was extracted with ethyl acetate. The organic phase was washed with brine (×3), dried (MgSO4), filtered and concentrated. It was triturated with CH3CN to provide the titled compound as white solid (1.05 g, 57%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic phase was washed with brine (×3)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customIt was triturated with CH3CN

Sources & evidence

ORD record
ord-18033024cc424142bf4593ee7e19bfe7
Source dataset
uspto-grants-2011_02
Patent number
US07888374B2

Reaction notes

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