Tetrahydrofuran → HCID 86731277, compound

HRID 2277213Notes

Reaction equation

HRID 2277213 reaction equation
[N:1]([CH:4]([CH3:28])[CH2:5][O:6][CH:7]1[CH2:27][C:11]2[N:12]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH:23]4[CH2:25][CH2:24]4)=[C:17]([F:26])[CH:16]=3)[O:14][C:10]=2[CH2:9][CH2:8]1)=[N+]=[N-].C1C[O:32][CH2:31][CH2:30]1>[C].[Pd]>[CH:23]1([CH2:22][O:21][C:18]2[CH:19]=[CH:20][C:15]([C:13]3[O:14][C:10]4[CH2:9][CH2:8][CH:7]([O:6][CH2:5][CH:4]([NH:1][C:31](=[O:32])[CH3:30])[CH3:28])[CH2:27][C:11]=4[N:12]=3)=[CH:16][C:17]=2[F:26])[CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 86731278HCID 86731278, compound

Product 1

HCID 86731277HCID 86731277, compound

Reagents, catalysts & solvents 1

HCID 178418390HCID 178418390, compoundCatalyst

Procedure

A mixture of 5-(2-azidopropoxy)-2-(4-(cyclopropylmethoxy)-3-fluorophenyl)-4,5,6,7-tetrahydro-1,3-benzoxazole (3.08 g), 10% palladium-carbon (containing water (50%), 500 mg) and THF (10 mL) was stirred at room temperature for 10 min under a hydrogen atmosphere. The catalyst was removed by filtration, and the obtained filtrate was concentrated under reduced pressure. To the obtained residue were added pyridine (10 mL) and acetic anhydride (10 mL), and the mixture was stirred at room temperature for 10 min. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate/methanol) to give the title compound (2.80 g).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe obtained filtrate was concentrated under reduced pressure
  3. additionTo the obtained residue were added pyridine (10 mL) and acetic anhydride (10 mL)
  4. stirringthe mixture was stirred at room temperature for 10 min
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate/methanol)

Sources & evidence

ORD record
ord-b6e23c645f90481399332d01c5c986b6
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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