O-(Tetrahydropyran-2-yl)hydroxylamine → HCID 58418151, compound

HRID 588509Notes

Reaction equation

HRID 588509 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][C@@H:13]([C:15]1[CH:19]=[C:18]([C:20]([OH:22])=O)[O:17][N:16]=1)[CH3:14])=[O:11].CN(C([O:30][N:31]1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.O1CCCCC1ON>CN(C=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][C@@H:13]([C:15]1[CH:19]=[C:18]([C:20]([NH:31][OH:30])=[O:22])[O:17][N:16]=1)[CH3:14])=[O:11]

Participants

5

Reactant 3

HCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58418192HCID 58418192, compound

Product 1

HCID 58418151HCID 58418151, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To the crude (R)-3-(1-(benzofuran-2-carboxamido)ethyl)isoxazole-5-carboxylic acid in a microwave vial was added HATU (0.0544 g, 0.143 mmol), TEA (0.087 g, 0.858 mmol) in DMF (1.0 mL), followed by O-(tetrahydropyran-2-yl)hydroxylamine (0.0335 g, 0.286 mmol) in DMF (1.0 mL). The mixture was shaken at rt for 16 h, then the solvent was evaporated. To the residue was added THF (2.0 mL) and hydrochloric acid (0.0715 mL, 4.0 M in 1,4-dioxane). After shaking at rt for 1 h, the solvent was evaporated. To the residue was added DMSO (1.2 mL). After filtration, the solution was purified by prep-HPLC to give ((R)-3-(1-(benzofuran-2-carboxamido)ethyl)-N-hydroxyisoxazole-5-carboxamide. LC-MS: (FA) ES+ 347.

Workup

  1. customthe solvent was evaporated
  2. additionTo the residue was added THF (2.0 mL) and hydrochloric acid (0.0715 mL, 4.0 M in 1,4-dioxane)
  3. stirringAfter shaking at rt for 1 h
  4. customthe solvent was evaporated
  5. additionTo the residue was added DMSO (1.2 mL)
  6. filtrationAfter filtration
  7. customthe solution was purified by prep-HPLC

Sources & evidence

ORD record
ord-3a7da671ac62496cbc4f4c0b48013c96
Source dataset
uspto-grants-2016_01
Patent number
US09227951B2

Reaction notes

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