Ethoxyethylamine → HCID 69482724, compound

HRID 2364253Notes

Reaction equation

HRID 2364253 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:33])=[C:14]([C:28](OCC)=[O:29])[C:15](=[O:27])[N:16]3[CH2:19][C:20](=[O:26])[N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[CH2:34]([O:36][CH2:37][CH2:38][NH2:39])[CH3:35]>>[CH2:34]([O:36][CH2:37][CH2:38][NH:39][C:28]([C:14]1[C:15](=[O:27])[N:16]([CH2:19][C:20](=[O:26])[N:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)[C:17]2[C:12]([C:13]=1[OH:33])=[N:11][CH:10]=[C:9]([CH2:8][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[CH:18]=2)=[O:29])[CH3:35]

Participants

3

Reactant 2

HCID 66970EthoxyethylamineHCID 58882934HCID 58882934, compound

Product 1

HCID 69482724HCID 69482724, compound

Procedure

This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-l -[2-oxo-2-(1-pyrrolidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate and 2-ethoxyethylamine 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), 8.53 (1H, d, J=1 Hz), 7.15 (2H, dd, J=8.6, 5.5 Hz), 7.08 (1H, s), 7.02 (2H, m), 4.87 (2H, s), 4.11 (2H, s), 3.61 (4H, m), 3.59-3.44 (6H, m), 2.04 (2H, m, J=7 Hz), 1.89 (2H, m, J=7 Hz), 1.22 (3H, t, J=7 Hz); HRMS calcd for C26H29FN4O5+H+: 497.2200. Found: 497.2190.

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-06ef8b06678a4937b4a735f5ede24549
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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