1,8-Diazabicyclo(5.4.0)undec-7-ene → Ethyl 7-(4-fluorobenzyl)-4-hydroxy-2-oxo-1-[2-oxopyrrolidin-1-yl ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate

HRID 2364429Notes

Reaction equation

HRID 2364429 reaction equation
[CH2:1]([O:3][C:4](=[O:36])[CH2:5][C:6]([N:8]([CH2:28][CH2:29][N:30]1[CH2:34][CH2:33][CH2:32][C:31]1=[O:35])[C:9]1[C:10]([C:23]([O:25]CC)=O)=[N:11][CH:12]=[C:13]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH:14]=1)=[O:7])[CH3:2].C1CCN2C(=NCCC2)CC1>C(O)C>[F:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][C:13]2[CH:14]=[C:9]3[C:10]([C:23]([OH:25])=[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:36])[C:6](=[O:7])[N:8]3[CH2:28][CH2:29][N:30]3[CH2:34][CH2:33][CH2:32][C:31]3=[O:35])=[N:11][CH:12]=2)=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 69482032Ethyl 3-{[3-(ethyloxy)-3-oxopropanoyl][2-(2-oxo-1-pyrrolidinyl)ethyl]amino}-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate

Product 1

HCID 58882907Ethyl 7-(4-fluorobenzyl)-4-hydroxy-2-oxo-1-[2-oxopyrrolidin-1-yl ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 3-{[3-(ethyloxy)-3-oxopropanoyl][2-(2-oxo-1-pyrrolidinyl)ethyl]amino}-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate (1.80 g, 3.98 mmol) in ethanol (20 mL) was treated with DBU (1.53 mL, 10.3 mmol). After stirring under nitrogen for 20 min., the reaction was quenched with 1N HCl (7.8 mL) and evaporated in vacuo. Trituration with water and filtration provided the product as a white solid: 1H NMR (CDCl3) δ 8.50 (1H, d, J=1.4 Hz), 8.11 (1H, s), 7.26 (2H, m), 7.00 (2H, ddd, J˜9, 9, 2 Hz), 4.52 (2H, q, J=7 Hz), 4.33 (2H, br t, J˜7 Hz), 4.14 (2H, s), 3.52-3.44 (4H, m), 2.35 (2H, t, J=8 Hz), 2.00 (2H, m), 1.48 (3H, t, J=7 Hz); ES+ MS: 476 (M+Na+).

Workup

  1. customthe reaction was quenched with 1N HCl (7.8 mL)
  2. customevaporated in vacuo
  3. filtrationTrituration with water and filtration

Sources & evidence

ORD record
ord-dcd94c74b0464771ad50e23448d96a01
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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