3,3-Dimethylglutaric anhydride → 3,3-Dimethyl-4-(3-(3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl)-1,2,4-oxadiazol-5-yl)butanoic acid

HRID 585548Notes

Reaction equation

[OH:1]/[N:2]=[C:3](\[NH2:17])/[CH2:4][CH2:5][CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[CH2:13][CH2:12][CH2:11][NH:10][C:9]=2[N:8]=1.[CH3:18][C:19]1([CH3:27])[CH2:25][C:24](=O)[O:23][C:21](=[O:22])[CH2:20]1>O1CCOCC1>[CH3:18][C:19]([CH3:27])([CH2:25][C:24]1[O:1][N:2]=[C:3]([CH2:4][CH2:5][CH2:6][C:7]2[CH:16]=[CH:15][C:14]3[CH2:13][CH2:12][CH2:11][NH:10][C:9]=3[N:8]=2)[N:17]=1)[CH2:20][C:21]([OH:23])=[O:22]

Participants

Conditions

Temperature: 100 °C

Procedure

A stirred mixture of (1Z)-N′-hydroxy-4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butanimidamide (100 mg, WO 99/30709), 3,3-dimethylglutaric anhydride (80 mg, Aldrich) and 1,4-dioxane (2 mL, Aldrich) was heated to 100° C. for 16 hrs. The resulting mixture was purified by HPLC to provide the title compound as a gum. 1H (CD3OD) δ 1.12 (6H, s); 1.96 (2H, p); 2.14 (2H, p); 2.36 (2H, s); 2.80 (6H, m); 3.05 (2H, s); 3.50 (2H, t); 6.63 (1H, d); 7.57 (1H, d).

Workup

customThe resulting mixture was purified by HPLC

Sources & evidence

ORD record: ord-5c8082abd299465fa52121d77cc8009b
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06933304B2

Reaction notes

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