Cyclopentane-1,1-diacetic anhydride → 2-(1-((3-(3-(5,6,7,8-Tetrahydro-1,8-naphthyridin-2-yl)propyl)-1,2,4-oxadiazol-5-yl)methyl)cyclopentyl)acetic acid

HRID 585549Notes

Reaction equation

HRID 585549 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.[CH2:18]1[CH2:22][C:21]2([CH2:29][C:27](=O)[O:26][C:24](=[O:25])[CH2:23]2)[CH2:20][CH2:19]1>O1CCOCC1>[N:8]1[C:9]2[NH:10][CH2:11][CH2:12][CH2:13][C:14]=2[CH:15]=[CH:16][C:7]=1[CH2:6][CH2:5][CH2:4][C:3]1[N:17]=[C:27]([CH2:29][C:21]2([CH2:23][C:24]([OH:26])=[O:25])[CH2:22][CH2:18][CH2:19][CH2:20]2)[O:1][N:2]=1

Participants

4

Reactant 2

HCID 79743Cyclopentane-1,1-diacetic anhydrideHCID 21927918HCID 21927918, compound

Product 1

HCID 102286622-(1-((3-(3-(5,6,7,8-Tetrahydro-1,8-naphthyridin-2-yl)propyl)-1,2,4-oxadiazol-5-yl)methyl)cyclopentyl)acetic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

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-tetramethyleneglutaric 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 1.68 (8H, m); 1.95 (2H, p); 2.13 (2H, p); 2.45 (2H, s); 2.80 (6H, m); 3.15 (2H, s); 3.50 (2H, t); 6.63 (1H, d);

Workup

  1. customThe resulting mixture was purified by HPLC

Sources & evidence

ORD record
ord-f568cfa78e8149bf8283e03730012bae
Source dataset
uspto-grants-2005_08
Patent number
US06933304B2

Reaction notes

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