2-Butynoic acid → N-(2-(6-(5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)pyridin-2-yloxy)ethyl)but-2-ynamide

HRID 1774666Notes

Reaction equation

HRID 1774666 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][O:5][C:6]1[N:11]=[C:10]([NH:12][C:13]2[C:14](=[O:21])[N:15]([CH3:20])[CH:16]=[C:17]([Br:19])[CH:18]=2)[CH:9]=[CH:8][CH:7]=1.[C:22](O)(=[O:26])[C:23]#[C:24][CH3:25].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CC(=O)OCC>[Br:19][C:17]1[CH:18]=[C:13]([NH:12][C:10]2[N:11]=[C:6]([O:5][CH2:4][CH2:3][NH:2][C:22](=[O:26])[C:23]#[C:24][CH3:25])[CH:7]=[CH:8][CH:9]=2)[C:14](=[O:21])[N:15]([CH3:20])[CH:16]=1

Participants

7

Reactant 4

HCID 685352-Butynoic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 1181168943-(6-(2-aminoethoxyl)pyridin-2-ylamino)-5-bromo-1-methylpyridin-2(1H)-one hydrochloride

Product 1

HCID 118116783N-(2-(6-(5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)pyridin-2-yloxy)ethyl)but-2-ynamideYield 74.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-(6-(2-aminoethoxyl)pyridin-2-ylamino)-5-bromo-1-methylpyridin-2(1H)-one hydrochloride 103a (1.0 g, 2.66 mmol), but-2-ynoic acid (268 mg, 3.19 mmol), HATU (1.21 g, 3.19 mmol) and DIPEA (1.14 mL, 6.65 mmol) in DMF (10 mL) was stirred at rt overnight. The reaction mixture was diluted with EA and washed with water. The organic layer was separated, dried over Na2SO4, filtered and concentrated. The residue was washed with PE/EA (2 mL/20 mL) and dried to give N-(2-(6-(5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)pyridin-2-yloxy)ethyl)but-2-ynamide 116a (800 mg, 74%) as light yellow solid. ESI-LCMS: m/z=404.9

Workup

  1. washwashed with water
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washThe residue was washed with PE/EA (2 mL/20 mL)
  7. customdried

Sources & evidence

ORD record
ord-4fbabcbbe0ed45eb96ddb76fc5a01103
Source dataset
uspto-grants-2016_02
Patent number
US09260415B2

Reaction notes

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