2-Phenylglutaric anhydride → 2-phenyl-4-{3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl}butanoic Acid

HRID 1243515Notes

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.[C:18]1([CH:24]2[CH2:30][CH2:29][C:28](=O)[O:27][C:25]2=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O1CCOCC1>[C:18]1([CH:24]([CH2:30][CH2:29][C:28]2[O:1][N:2]=[C:3]([CH2:4][CH2:5][CH2:6][C:7]3[CH:16]=[CH:15][C:14]4[CH2:13][CH2:12][CH2:11][NH:10][C:9]=4[N:8]=3)[N:17]=2)[C:25]([OH:27])=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

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), 2-phenylglutaric anhydride (80 mg, Aldrich) and 1,4-dioxane (2 mL, Aldrich) was heated to 100° C. for 16 hrs. The resulting solution was purified by HPLC to provide the title compound as a gum. 1H (CD3OD) δ 1.93 (2H, p); 2.12 (2H, m); 2.18–2.37 (2H, comp. band); 2.42–2.55 (1H, comp. band); 2.74–2.90 (7H, comp. band); 3.48 (2H, t); 3.66/4.38 (1H, t); 6.60/6.62 (1H, d); 7.23–7.39 (5H, comp. band); 7.51/7.55 (1H, d).

Workup

customThe resulting solution was purified by HPLC

Sources & evidence

ORD record: ord-761d4f30aea04dd6be195c2c11975ee1
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07119098B2

Reaction notes

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