2-Methoxyethylamine → HCID 54681849, compound

HRID 2364178Notes

Reaction equation

[CH2:1]([C:8]1[CH:17]=[C:16]2[C:11]([C:12]([OH:28])=[C:13]([C:23](OCC)=[O:24])[C:14](=[O:22])[N:15]2[CH2:18][CH:19]2[CH2:21][CH2:20]2)=[N:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:29][O:30][CH2:31][CH2:32][NH2:33]>>[CH2:1]([C:8]1[CH:17]=[C:16]2[C:11]([C:12]([OH:28])=[C:13]([C:23]([NH:33][CH2:32][CH2:31][O:30][CH3:29])=[O:24])[C:14](=[O:22])[N:15]2[CH2:18][CH:19]2[CH2:20][CH2:21]2)=[N:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 80182-Methoxyethylamine

HCID 58882910HCID 58882910, compound

Product 1

HCID 54681849HCID 54681849, compound

Procedure

This compound was prepared from ethyl 7-benzyl-1-(cyclopropylmethyl)-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and 2-methoxyethylamine employing methods similar to those described in Example 5 and was obtained as an off-white solid: 1H NMR (CDCl3) δ 10.36 (1H, br t, J=5 Hz), 8.59 (1H, d, J=1.3 Hz), 7.46 (1H, s), 7.34 (2H, m), 7.26 (1H, m), 7.20 (2H, d, J=7 Hz), 4.16 (2H, s), 4.08 (2H, d, J=7 Hz), 3.64 (2H, q, J˜5 Hz), 3.58 (2H, t, J˜5 Hz), 3.40 (3H, s), 1.00 (1H, m), 0.46 (2H, m), 0.39 (2H, m); HRMS calcd for C23H25N3O4+H+: 408.1923. Found: 408.1914.

Workup

customwas obtained as an off-white solid

Sources & evidence

ORD record: ord-0070e440dd4b4cf995145443f2add392
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691991B2

Reaction notes

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