Sodium Hydroxide → HCID 69481024, compound

HRID 2364484Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:28])=[C:14]([C:21]([NH:23][C@@H:24]([CH3:27])[CH2:25][OH:26])=[O:22])[C:15](=[O:20])[N:16]3[CH3:19])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[OH-].[Na+:30]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([O-:28])=[C:14]([C:21]([NH:23][C@@H:24]([CH3:27])[CH2:25][OH:26])=[O:22])[C:15](=[O:20])[N:16]3[CH3:19])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[Na+:30]

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 69481025HCID 69481025, compound

Product 1

HCID 69481024HCID 69481024, compoundYield 72%

Procedure

In a manner similar to that described in example 474, from 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[(1S)-2-hydroxy-1-methylethyl]-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (436 mg, 1.13 mmol described in example 359) and sodium hydroxide (1.08 mL of a 1 N solution) was prepared sodium 7-[(4-fluorophenyl)methyl]-3-({[(1S)-2-hydroxy-1-methylethyl]amino}carbonyl)-l -methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-4-olate (331 mg, 72% yield) as a white solid. 1H NMR (DMSO-d6) δ 10.41 (d, J=7.2 Hz, 1 H), 8.16 (s, 1 H), 7.59 (s, 1 H), 7.33-7.29 (m, 2 H), 7.11-7.07 (m, 2 H), 4.79 (m, 1 H), 3.93 (m, 1 H), 3.41 (m, 1 H), 3.28 (s, 3 H), 3.24 (m, 1 H), 1.03 (d, J=6.8 Hz, 3 H); MS m/z 386 (M+1).

Sources & evidence

ORD record: ord-9daba08a00bb4fc19c87d13ac7077cef
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691991B2

Reaction notes

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