Ethanolamine → HCID 69483303, compound

HRID 2364435Notes

Reaction equation

HRID 2364435 reaction equation
[CH:1]1([NH:4][C:5](=[O:32])[CH2:6][N:7]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([CH2:17][C:18]4[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=4)[CH:15]=3)[C:10]([OH:25])=[C:9]([C:26](OCC)=[O:27])[C:8]2=[O:31])[CH2:3][CH2:2]1.[CH2:33]([CH2:35][NH2:36])[OH:34]>>[CH:1]1([NH:4][C:5](=[O:32])[CH2:6][N:7]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([CH2:17][C:18]4[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=4)[CH:15]=3)[C:10]([OH:25])=[C:9]([C:26]([NH:36][CH2:35][CH2:33][OH:34])=[O:27])[C:8]2=[O:31])[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 700EthanolamineHCID 69482711HCID 69482711, compound

Product 1

HCID 69483303HCID 69483303, compound

Procedure

This compound was prepared from ethyl 1-[2-(cyclopropylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and ethanolamine employing methods similar to those described in Example 245. The crude material was triturated with a mixture of MeOH and 1N HCl to afford the product as a white solid: 1H NMR (d6-DMSO) δ 10.25 (1H, t, J=5 Hz), 8.54 (1H, s), 8.25 (1H, d, J=4 Hz), 7.74 (1H, s), 7.32 (2H, dd, J=8.5, 5.7 Hz), 7.11 (2H, t, J˜9 Hz), 4.92 (1H, br m), 4.80 (2H, s), 4.11 (2H, s), 3.54 (2H, t, J=5 Hz), 3.42 (2H, q, J˜5 Hz), 2.57 (1H, m), 0.59 (2H, m), 0.35 (2H, m); HRMS calcd for C23H23FN4O5+H+: 455.1731. Found: 455.1728.

Workup

  1. customThe crude material was triturated with a mixture of MeOH and 1N HCl

Sources & evidence

ORD record
ord-5de6ba1de9334c65a444c0959e7b1686
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

Loading…