Diisopropylethylamine → N-(2-(benzofuran-3-yl)ethyl)-5-(3-fluorobenzyl)isoxazole-3-carboxamide

HRID 58697Notes

Reaction equation

HRID 58697 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][C:6]1[O:10][N:9]=[C:8]([C:11]([OH:13])=O)[CH:7]=1.[O:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[C:19]([CH2:26][CH2:27][NH2:28])=[CH:18]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C>[O:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[C:19]([CH2:26][CH2:27][NH:28][C:11]([C:8]2[CH:7]=[C:6]([CH2:5][C:4]3[CH:14]=[CH:15][CH:16]=[C:2]([F:1])[CH:3]=3)[O:10][N:9]=2)=[O:13])=[CH:18]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 124208122-Benzo[b]furan-3-ylethylamineHCID 668321075-(3-Fluorobenzyl)isoxazole-3-carboxylic acid

Product 1

HCID 66831986N-(2-(benzofuran-3-yl)ethyl)-5-(3-fluorobenzyl)isoxazole-3-carboxamideYield 9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of the 5-(3-fluorobenzyl)isoxazole-3-carboxylic acid (0.057 g, 0.257 mmol), 2-(benzofuran-3-yl)ethanamine (0.042 g; 0.260 mmol), HATU (0.108 g; 0.285 mmol) and N,N-diisopropylethylamine (0.112 mL; 0.649 mmol) in DMF (3 mL), was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and sodium hydrogen sulfate, the organic layer was washed with sodium carbonate, brine, dried and concentrated under reduced pressure. The crude mixture was purified by preparative HPLC (method 2) to yield 0.008 g (9%) of the title compound as a white solid.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and sodium hydrogen sulfate
  2. washthe organic layer was washed with sodium carbonate, brine
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe crude mixture was purified by preparative HPLC (method 2)

Sources & evidence

ORD record
ord-cc5359c9b1594e5a8cfb81fada5fb9f8
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Reaction notes

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