Ethanolamine → 1-Cyclopropyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 2364531Notes

Reaction equation

HRID 2364531 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[N:9][CH:10]=[C:11]([CH2:14][C:15]4[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=4)[CH:12]=3)[C:7]([OH:22])=[C:6]([C:23](OCC)=[O:24])[C:5]2=[O:28])[CH2:3][CH2:2]1.[NH2:29][CH2:30][CH2:31][OH:32]>C(O)C>[CH:1]1([N:4]2[C:13]3[C:8](=[N:9][CH:10]=[C:11]([CH2:14][C:15]4[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=4)[CH:12]=3)[C:7]([OH:22])=[C:6]([C:23]([NH:29][CH2:30][CH2:31][OH:32])=[O:24])[C:5]2=[O:28])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 69481040HCID 69481040, compound

Product 1

HCID 694828091-Cyclopropyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamideYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 1-cyclopropyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (24 mg, 0.06 mmol) and 2-aminoethanol (0.05 mL) in ethanol (1 mL) was heated in a microwave for 20 minutes. The reaction mixture was concentrated in vacuo and the residue taken up in water. The solution was acidified with 1 N HCl to a final pH˜4. The precipitate was filtered through a Teflon filter and the solids collected. This material was azeotroped with methanol to provide the title compound (16 mg, 64%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 10.38 (s, 1 H), 8.54 (s, 1 H), 7.80 (s, 1 H), 7.17 (m, 2 H), 7.03 (m, 2 H), 4.13 (s, 2 H), 3.84 (m, 2 H), 3.62 (m, 2 H), 2.82 (m, 1 H), 1.23 (m, 2 H), 0.76 (m, 2 H); HRMS m/z calcd for C21H21N3O4F (M+H)+ 398.1517, found 398.1512.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. filtrationThe precipitate was filtered through a Teflon
  3. filtrationfilter
  4. customthe solids collected
  5. customThis material was azeotroped with methanol

Sources & evidence

ORD record
ord-fe7e4875e23740f8824049fc7d59f1bf
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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