Ethylamine → HCID 18668644, compound

HRID 2115319Notes

Reaction equation

HRID 2115319 reaction equation
CN(C(O[N:9]1N=N[C:11]2C=CC=C[C:10]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[Br:23][C:24]1[N:29]=[C:28]([C:30]([OH:32])=O)[CH:27]=[CH:26][CH:25]=1.C(N)C.CCN(C(C)C)C(C)C>CN(C=O)C.C1COCC1.C(OCC)(=O)C.O>[CH2:10]([NH:9][C:30]([C:28]1[CH:27]=[CH:26][CH:25]=[C:24]([Br:23])[N:29]=1)=[O:32])[CH3:11]

Participants

9

Reactant 4

HCID 6341EthylamineHCID 81531DiisopropylethylamineHCID 5939196-Bromopyridine-2-carboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 18668644HCID 18668644, compoundYield 96%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

TBTU (6.5 mmol) was added to a solution of 6-bromo-pyridine-2-carboxylic acid (5.0 mmol) in DMF (30 mL). A solution of ethylamine in THF (1.0 mol/L, 5.0 mL) and DIPEA (15.0 mmol) were added and the reaction mixture was stirred for 16 h. Water (100 mL) and ethyl acetate (100 mL) were added, the layers were separated, and the aqueous layer was extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with brine (100 mL), dried over Na2SO4, and concentrated in vacuo to give 1.1 g (4.8 mmol, 96%) of the desired amide as a yellow oil which was used without further purification.

Workup

  1. customthe layers were separated
  2. extractionthe aqueous layer was extracted with ethyl acetate (2×100 mL)
  3. washThe combined organic layers were washed with brine (100 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5cba870c2c0f48f59f167c54adc78640
Source dataset
uspto-grants-2008_10
Patent number
US07435815B2

Reaction notes

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