2-Furanpropionic acid → N-[2-(2-Cyclopentyl-4,6-dioxo-tetrahydro-pyran-2-yl)-ethyl]-3-furan-2-yl-propionamide

HRID 1453330Notes

Reaction equation

HRID 1453330 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1([CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[O:9][C:8](=[O:10])[CH2:7][C:6](=[O:11])[CH2:5]1.[O:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[CH2:22][CH2:23][C:24](O)=[O:25].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH:12]1([C:4]2([CH2:3][CH2:2][NH:1][C:24](=[O:25])[CH2:23][CH2:22][C:18]3[O:17][CH:21]=[CH:20][CH:19]=3)[CH2:5][C:6](=[O:11])[CH2:7][C:8](=[O:10])[O:9]2)[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 702862-Furanpropionic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68867536HCID 68867536, compound

Product 1

HCID 58762596N-[2-(2-Cyclopentyl-4,6-dioxo-tetrahydro-pyran-2-yl)-ethyl]-3-furan-2-yl-propionamideYield 19%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-(2-Amino-ethyl)-6-cyclopentyl-dihydro-pyran-2,4-dione (90 mg, 0.4 mmol) from Step 5 below, TEA (0.22 mL, 1.6 mmol), 3-furan-2-yl-propionic acid (67 mg, 0.48 mmol) and HATU (182 mg, 0.48 mmol) in DMF (2 mL) was stirred at room temperature overnight. The reaction was purified directly by preparatory HPLC to yield the desired product (26 mg, 19% yield). 1H NMR (CDCl3) δ: 1.27-3.47 (m, 21H), 6.94 (s, 1H), 6.19 (s, 1H), 7.22 (s, 1H). MS (ESI): 346 (M−H).

Workup

  1. customThe reaction was purified directly by preparatory HPLC

Sources & evidence

ORD record
ord-56f0552bfe2043ceaa8a6df38f704ffa
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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