2-Methoxyethylamine → HCID 58882975, compound

HRID 2364200Notes

Reaction equation

HRID 2364200 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]([N:22]([CH3:27])[CH2:23][CH2:24][O:25][CH3:26])=[O:21])=[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]([N:22]([CH3:27])[CH2:23][CH2:24][O:25][CH3:26])=[O:21])=[N:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 80182-MethoxyethylamineHCID 58882985HCID 58882985, compound

Product 1

HCID 58882975HCID 58882975, compound

Procedure

This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-(2-{methyl[2-(methyloxy)ethyl]amino}-2-oxoethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and 2-methoxyethylamine employing methods similar to 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 an off-white solid: 1H NMR (CDCl3) mixture of rotamers δ 10.20 (1H, br), 8.55 and 8.50 (1H, s), 7.34 and 7.10 (1H, s), 7.15-6.97 (4H, m), 5.21 and 4.98 (2H, s), 4.10 (2H, s), 3.64-3.41 (8H, m), 3.40 and 3.39 (3H, s), 3.34 and 3.32 (3H, s), 3.17 and 2.97 (3H, s); HRMS calcd for C25H29FN4O6+H+: 501.2149. Found: 501.2140.

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 an off-white solid

Sources & evidence

ORD record
ord-ba7ed62cd762420baf03f2ae8170d589
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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