(R)-3-Aminotetrahydrofuran → 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-[2-(2-oxo-1-piperidinyl)ethyl]-N-[(3R)-tetrahydro-3-furanyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 2364511Notes

Reaction equation

HRID 2364511 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:34])=[C:14]([C:29](OCC)=[O:30])[C:15](=[O:28])[N:16]3[CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][C:22]3=[O:27])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[O:35]1[CH2:39][CH2:38][C@@H:37]([NH2:40])[CH2:36]1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:34])=[C:14]([C:29]([NH:40][C@@H:37]4[CH2:38][CH2:39][O:35][CH2:36]4)=[O:30])[C:15](=[O:28])[N:16]3[CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][C:22]3=[O:27])=[N:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 10996958(R)-3-AminotetrahydrofuranHCID 69482570Ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-[2-(2-oxo-1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 694815017-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-[2-(2-oxo-1-piperidinyl)ethyl]-N-[(3R)-tetrahydro-3-furanyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide

Procedure

This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-[2-(2-oxo-1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate and (3R)-tetrahydro-3-furanamine using methods similar to Example 563 to provide an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.54-1.65 (m, 4 H), 1.88 (d, J=8.42 Hz, 1 H), 2.04 (t, J=5.69 Hz, 2 H), 2.23-2.32 (m, 1 H), 3.25-3.30 (m, 2 H), 3.45-3.54 (m, 2 H), 3.65 (dd, J=9.16, 2.84 Hz, 1 H), 3.72-3.88 (m, 3 H), 4.17 (s, 2 H), 4.39 (t, J=7.16 Hz, 2 H), 4.55 (s, 1 H), 7.11-7.17 (m, 2 H), 7.38-7.43 (m, 2 H), 8.23 (s, 1 H), 8.58 (d, J=1.47 Hz, 1 H), 10.50 (d, J=7.16 Hz, 1 H), 16.83 (s, 1 H); ES+ MS: 509 (M+H+).

Workup

  1. customto provide an off-white solid

Sources & evidence

ORD record
ord-1417dc9ee19f4a8e9c5f64b458b70fb6
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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