1-Phenethylamine → HCID 54706739, compound

HRID 2364151Notes

Reaction equation

[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:9][N:10]=2)[NH:5][C:4](=[O:19])[C:3]=1[C:20](OCC)=[O:21].[CH3:25][CH:26]([NH2:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[CH:9][N:10]=2)[NH:5][C:4](=[O:19])[C:3]=1[C:20]([NH:33][CH:26]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH3:25])=[O:21]

Participants

Reactant 2

HCID 74081-Phenethylamine

HCID 54729996HCID 54729996, compound

Product 1

HCID 54706739HCID 54706739, compound

Procedure

This compound was prepared from ethyl 4-hydroxy-2-oxo-7-(phenylmethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxylate and α-methylbenzylamine employing methods similar to those described in Example 2 and was obtained as a white solid: 1H NMR (d6-DMSO) δ 12.40 (1H, br), 10.80 (1H, br), 8.35 (1H, br), 7.35-7.24 (1H, m), 5.14 (1H, m), 4.05 (2H, br s), 1.46 (3H, br); HRMS calcd for C24H21N3O3+H+: 400.1661. Found: 400.1670.

Workup

customwas obtained as a white solid

Sources & evidence

ORD record: ord-fe339a939eb24815aa7452668d0492c6
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691991B2

Reaction notes

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