Ethanolamine → HCID 69482163, compound

HRID 2364227Notes

Reaction equation

HRID 2364227 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.[CH2:35]([CH2:37][NH2:38])[OH:36]>>[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:38][CH2:37][CH2:35][OH:36])=[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 700EthanolamineHCID 69480365HCID 69480365, compound

Product 1

HCID 69482163HCID 69482163, 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 ethanolamine 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 10.32 (1H, m), 8.56 (1H, s), 7.16 (2H, dd, J=9, 6 Hz), 7.03 (2H, t, J=9 Hz), 6.97 (1H, s), 4.93 (2H, s), 4.11 (2H, s), 3.83 (2H, t, J=5 Hz), 3.62 (2H, q, J=5 Hz), 3.50 (2H, t, J=6 Hz), 3.44 (2H, t, J=5 Hz), 1.69-1.58 (6H, m); HRMS calcd for C25H27FN4O5+H+: 483.2044. Found: 483.2060.

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-8309d22832b14827bcba328c9c8755fa
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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