Acetic Anhydride → 6-(4-Fluorobenzyl)-4-methoxy-1-[methyl(methylsulfonyl)amino]-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridin-3-yl acetate

HRID 1817310Notes

Reaction equation

[F:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[CH2:16][CH2:15][C:14]3[C:13]([N:17]([CH3:22])[S:18]([CH3:21])(=[O:20])=[O:19])=[N+:12]([O-])[CH:11]=[C:10]([O:24][CH3:25])[C:9]=3[C:8]2=[O:26])=[CH:4][CH:3]=1.[C:29]([O:32]C(=O)C)(=[O:31])[CH3:30]>>[C:29]([O:32][C:11]1[N:12]=[C:13]([N:17]([CH3:22])[S:18]([CH3:21])(=[O:20])=[O:19])[C:14]2[CH2:15][CH2:16][N:7]([CH2:6][C:5]3[CH:27]=[CH:28][C:2]([F:1])=[CH:3][CH:4]=3)[C:8](=[O:26])[C:9]=2[C:10]=1[O:24][CH3:25])(=[O:31])[CH3:30]

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 69058516N-[6-(4-Fluorobenzyl)-4-methoxy-2-oxido-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridin-1-yl]-N-methylmethanesulfonamide

Product 1

HCID 690609546-(4-Fluorobenzyl)-4-methoxy-1-[methyl(methylsulfonyl)amino]-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridin-3-yl acetate

Procedure

A solution of N-[6-(4-fluorobenzyl)-4-methoxy-2-oxido-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridin-1-yl]-N-methylmethanesulfonamide (0.36 g, 0.889 mmol) in acetic anhydride (10 mL) was heated to 110° C. for 3 hours, then evaporated to dryness to give the intermediate 6-(4-fluorobenzyl)-4-methoxy-1-[methyl(methylsulfonyl)amino]-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridin-3-yl acetate (ES MS (M+1)=452). The crude material was dissolved in methanol (6 mL) and treated with sodium methoxide (30% by weight in methanol, 0.5 mL, 2.6 mmol). After 1 hour, the product mixture was neutralized with 6 N HCl, then concentrated. The residue was partitioned between CHCl3 and 10% KHSO4. The organic extract was dried with Na2SO4, filtered, and concentrated under vacuum to provide the title compound.

Workup

customevaporated to dryness

Sources & evidence

ORD record: ord-b84f79a083354b9e8ef0397e1ff35f22
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07598264B2

Reaction notes

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