2-Aminopropanol → HCID 69481503, compound

HRID 2364289Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([CH2:18][C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)[CH:16]=3)[C:11]([OH:26])=[C:10]([C:27](OCC)=[O:28])[C:9]2=[O:32])=[CH:4][CH:3]=1.[NH2:33][CH:34]([CH3:37])[CH2:35][OH:36]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([CH2:18][C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)[CH:16]=3)[C:11]([OH:26])=[C:10]([C:27]([NH:33][CH:34]([CH3:37])[CH2:35][OH:36])=[O:28])[C:9]2=[O:32])=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 51262-Aminopropanol

HCID 59799019Ethyl 1-(4-fluorophenyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 69481503HCID 69481503, compoundYield 44%

Procedure

In a similar manner to that described in example 196, from ethyl 1-(4-fluorophenyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (20 mg, 0.043 mmol) and 2-amino-1-propanol (0.05 mL), was prepared 1-(4-fluorophenyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxy-1-methylethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (8.8 mg, 44% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.06 (d, J=7.6 Hz, 1 H), 8.53 (s, 1 H), 7.31-7.27 (m, 2 H), 7.22-7.18 (m, 2 H), 7.03-6.93 (m, 4 H), 6.71 (s, 1 H), 4.29 (m, 1 H), 3.95 (s, 2 H), 3.73 (dd, J=10.8, 4 Hz, 1 H), 3.62 (dd, J=10.8, 6.4 Hz, 1 H), 1.26 (d, J=6.8 Hz, 3 H); MS m/z 466 (M+1).

Sources & evidence

ORD record: ord-b755251cfcdd4e77b6aef3b6db03422b
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691991B2

Reaction notes

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