2-Methoxyethylamine → HCID 69480203, compound

HRID 2364223Notes

Reaction equation

HRID 2364223 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][C:20](=[O:27])[N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[CH3:35][O:36][CH2:37][CH2:38][NH2:39]>>[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:39][CH2:38][CH2:37][O:36][CH3:35])=[O:30])[C:15](=[O:28])[N:16]3[CH2:19][C:20](=[O:27])[N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 80182-MethoxyethylamineHCID 69480365HCID 69480365, compound

Product 1

HCID 69480203HCID 69480203, compound

Procedure

This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-[2-oxo-2-(1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate and 2-methoxyethylamine employing methods similar to those those described in Example 9 and was purified by reverse phase preparative HPLC (C-18 stationary phase; 10-100% CH3CN/water/0.1% formic acid mobile phase). The product was obtained as a white solid: 1H NMR (CDCl3) δ 10.18 (1H, br m), 8.55 (1H, s), 7.15 (2H, dd, J=9, 5 Hz), 7.02 (2H, t, J=9 Hz), 6.96 (1H, s), 4.94 (2H, s), 4.11 (2H, s), 3.63 (2H, q, J=5 Hz), 3.56 (2H, t, J=5 Hz), 3.50 (2H, t, J=5 Hz), 3.44 (2H, t, J=5 Hz), 3.39 (3H, s), 1.68 (2H, m), 1.60-1.50 (4H, m); HRMS calcd for C26H29FN4O5+H+: 497.2200. Found: 497.2183.

Workup

  1. customwas purified by reverse phase preparative HPLC (C-18 stationary phase; 10-100% CH3CN/water/0.1% formic acid mobile phase)
  2. customThe product was obtained as a white solid

Sources & evidence

ORD record
ord-a7fa89a800be4e6899af2476c36fd7f5
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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