2-Methoxyethylamine → HCID 54683968, compound

HRID 2364184Notes

Reaction equation

[CH2:1]([C:8]1[CH:17]=[C:16]2[C:11]([C:12]([OH:30])=[C:13]([C:25](OCC)=[O:26])[C:14](=[O:24])[N:15]2[CH2:18][C:19]2[S:20][CH:21]=[CH:22][N:23]=2)=[N:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:31][O:32][CH2:33][CH2:34][NH2:35]>>[CH2:1]([C:8]1[CH:17]=[C:16]2[C:11]([C:12]([OH:30])=[C:13]([C:25]([NH:35][CH2:34][CH2:33][O:32][CH3:31])=[O:26])[C:14](=[O:24])[N:15]2[CH2:18][C:19]2[S:20][CH:21]=[CH:22][N:23]=2)=[N:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 80182-Methoxyethylamine

HCID 58882970HCID 58882970, compound

Product 1

HCID 54683968HCID 54683968, compound

Procedure

This compound was prepared from ethyl 7-benzyl-4-hydroxy-2-oxo-1-(1,3-thiazol-2-ylmethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxylate and 2-methoxyethylamine employing methods similar to those described in Example 5 and was obtained as a white solid: 1H NMR (d6-DMSO) δ 10.21 (1H, t, J=5 Hz), 8.56 (1H, s), 8.12 (1H, s), 7.69 (1H, d, J=3.2 Hz), 7.67 (1H, d, J=3.2 Hz) 7.28-7.22 (4H, m), 7.18 (1H, t, J=7 Hz), 5.78 (2H, s), 4.09 (2H, s), 3.56-3.48 (4H, m), 3.28 (3H, s); HRMS calcd for C23H22N4O4S+H+: 451.1440. Found: 451.1428.

Workup

customwas obtained as a white solid

Sources & evidence

ORD record: ord-e65a6941044443fa8af167eaaea38367
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691991B2

Reaction notes

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