Methoxyisopropylamine → 7-[(4-Fluorophenyl)methyl]-4-hydroxy-N-[1-methyl-2-(methyloxy)ethyl]-2-oxo-1-[2-(2-oxo-1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 2364496Notes

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.[CH3:35][O:36][CH2:37][CH:38]([NH2:40])[CH3:39]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:34])=[C:14]([C:29]([NH:40][CH:38]([CH3:39])[CH2:37][O:36][CH3:35])=[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:6][CH:7]=1

Participants

Reactant 2

HCID 123458Methoxyisopropylamine

HCID 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 694827087-[(4-Fluorophenyl)methyl]-4-hydroxy-N-[1-methyl-2-(methyloxy)ethyl]-2-oxo-1-[2-(2-oxo-1-piperidinyl)ethyl]-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 1-(methyloxy)-2-propanamine using methods similar to Example 563 to provide a white solid: 1H NMR (CDCl3) δ 10.17 (1H, d, J=8 Hz), 8.54 (1H, s), 8.27 (1H, s), 7.23 (2H, dd, J=5, 8 Hz), 6.98 (2H, t, J=8 Hz), 4.31-4.43 (3H, m), 4.15 (2H, s), 3.53 (2H, b), 3.47 (2H, d, J=5 Hz), 3.40 (3H, s), 3.36 (2H, b), 2.35 (2H, b), 1.75 (4H, b), 1.30 (3H, d, J=7 Hz); ES+ MS: 511 (M+H+).

Workup

customto provide a white solid

Sources & evidence

ORD record: ord-33c6a31369cc4a999569bfd64d4bd8cc
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691991B2

Reaction notes

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