Water → Ethyl 6-(3-chloro-4-fluorobenzyl)-4-hydroxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate

HRID 2066570Notes

Reaction equation

HRID 2066570 reaction equation
C(O[C:6]1[O:10][C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:8][CH:7]=1)CCC.[Cl:16][C:17]1[CH:18]=[C:19]([CH:28]=[CH:29][C:30]=1[F:31])[CH2:20][N:21]1[CH2:26][CH2:25][CH:24]=[CH:23][C:22]1=[O:27].O>>[Cl:16][C:17]1[CH:18]=[C:19]([CH:28]=[CH:29][C:30]=1[F:31])[CH2:20][N:21]1[CH2:26][CH2:25][C:24]2[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:8][CH:7]=[C:6]([OH:10])[C:23]=2[C:22]1=[O:27]

Participants

4

Reactant 3

HCID 962WaterHCID 594556041-(3-Chloro-4-fluorobenzyl)-5,6-dihydropyridin-2(1H)-oneHCID 66996945Ethyl 5-butoxy-1,3-oxazole-2-carboxylate

Product 1

HCID 59455599Ethyl 6-(3-chloro-4-fluorobenzyl)-4-hydroxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate

Conditions

Temperature
130 °C

Procedure

A mixture of ethyl 5-butoxy-1,3-oxazole-2-carboxylate (44.5 g, 208.6 mmol), 1-(3-chloro-4-fluorobenzyl)-5,6-dihydropyridin-2(1H)-one (25 g, 104.3 mmol), and water (2.82 mL, 156.7 mmol) was heated in a sealed heavy walled vessel at 130° C. with stirring for 72 hours. Upon cooling, the product mixture solidified. The solid was triturated with diethyl ether and collected by filtration. The product was further purified by crystallization from boiling ethyl acetate.

Workup

  1. temperatureUpon cooling
  2. customThe solid was triturated with diethyl ether
  3. filtrationcollected by filtration
  4. customThe product was further purified by crystallization

Sources & evidence

ORD record
ord-277554e047304a99944c3685e83dcba1
Source dataset
uspto-grants-2012_10
Patent number
US08293731B2

Reaction notes

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