1-Hydroxybenzotriazole → Ethyl 3-[(3-oxo-6-pyridin-4-yl-2,3-dihydropyridazine-4-carbonyl)amino]propionate

HRID 970179

Reaction equation

HRID 970179 reaction equation
ON1C2C=CC=CC=2N=N1.Cl.[CH2:12]([O:14][C:15](=[O:19])[CH2:16][CH2:17][NH2:18])[CH3:13].C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[O:53]=[C:54]1[C:59]([C:60](O)=[O:61])=[CH:58][C:57]([C:63]2[CH:68]=[CH:67][N:66]=[CH:65][CH:64]=2)=[N:56][NH:55]1>CN(C)C=O>[O:53]=[C:54]1[C:59]([C:60]([NH:18][CH2:17][CH2:16][C:15]([O:14][CH2:12][CH3:13])=[O:19])=[O:61])=[CH:58][C:57]([C:63]2[CH:68]=[CH:67][N:66]=[CH:65][CH:64]=2)=[N:56][NH:55]1

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 127902383-Oxo-6-(pyridin-4-yl)-2,3-dihydropyridazine-4-carboxylic acid

Product 1

HCID 10313657Ethyl 3-[(3-oxo-6-pyridin-4-yl-2,3-dihydropyridazine-4-carbonyl)amino]propionateYield 32.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
19 °C

Procedure

0.733 g of 1-hydroxybenzotriazole, 0.833 g of β-alanine ethyl ester hydrochloride, 0.96 cm3 of N,N-diisopropylethylamine and 2.06 g of O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate were successively added to 0.94 g of 3-oxo-6-pyridin-4-yl-2,3-dihydropyridazine-4-carboxylic acid dissolved in 100 cm3 of N,N-dimethylformamide. The reaction medium was stirred for 12 hours at 19° C. The solvent was evaporated off under reduced pressure (2 kPa; 55° C.). The solid residue was triturated in 20 cm3 of dichloromethane, suction-filtered and oven-dried under reduced pressure (10 kPa; 20° C.). After purification by chromatography on silica gel (particle size 40-63 μm, under an argon pressure of 150 kPa) eluting with dichloromethane, 0.45 g of ethyl 3-[(3-oxo-6-pyridin-4-yl-2,3-dihydropyridazine-4-carbonyl)amino]propionate was obtained in the form of a white solid melting at 180° C.

Workup

  1. customThe solvent was evaporated off under reduced pressure (2 kPa; 55° C.)
  2. customThe solid residue was triturated in 20 cm3 of dichloromethane
  3. filtrationsuction-filtered
  4. customoven-dried under reduced pressure (10 kPa; 20° C.)
  5. customAfter purification by chromatography on silica gel (particle size 40-63 μm
  6. washunder an argon pressure of 150 kPa) eluting with dichloromethane

Sources & evidence

ORD record
ord-b4855d0d9f7847fab242bfcd36fd2200
Source dataset
uspto-grants-2007_12
Patent number
US07309701B2

Linked notes

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