Benzofuran-2-carboxylic acid → HCID 58418129, compound

HRID 588507Notes

Reaction equation

HRID 588507 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]([OH:12])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[NH2:38][C@@H:39]([C:41]1[CH:45]=[C:44]([C:46]([O:48][CH2:49][CH3:50])=[O:47])[O:43][N:42]=1)[CH3:40]>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:38][C@@H:39]([C:41]1[CH:45]=[C:44]([C:46]([O:48][CH2:49][CH3:50])=[O:47])[O:43][N:42]=1)[CH3:40])=[O:12]

Participants

5

Reactant 3

HCID 10331Benzofuran-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86657337HCID 86657337, compound

Product 1

HCID 58418129HCID 58418129, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 2-dram vial containing benzofuran-2-carboxylic acid (0.0243 g, 0.150 mmol) was added HATU (0.057 g, 0.150 mmol.) in DMF (1.0 mL), and TEA (0.120 mL, 0.858 mmol). After shaking at rt for 30 min, (R)-ethyl 3-(1-aminoethyl)isoxazole-5-carboxylate hydrochloride (0.032 g, 0.143 mmol) was added. The mixture was shaken at rt for 16 h. The solvent was evaporated. To the residue was added water (1.0 mL) and DCE (3 mL). After separation, the aqueous layer was extracted with DCE (3 mL). The combined organic phases were concentrated to give (R)-ethyl 3-(1-(benzofuran-2-carboxamido)ethyl)isoxazole-5-carboxylate as a solid residue.

Workup

  1. stirringThe mixture was shaken at rt for 16 h
  2. customThe solvent was evaporated
  3. additionTo the residue was added water (1.0 mL) and DCE (3 mL)
  4. customAfter separation
  5. extractionthe aqueous layer was extracted with DCE (3 mL)
  6. concentrationThe combined organic phases were concentrated

Sources & evidence

ORD record
ord-591aa97df01541a7adafb0725bfe6495
Source dataset
uspto-grants-2016_01
Patent number
US09227951B2

Reaction notes

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