Tetrahydrofuran → HCID 86731284, compound

HRID 2277218Notes

Reaction equation

HRID 2277218 reaction equation
[N:1]([CH:4]([CH3:28])[CH2:5][O:6][CH:7]1[CH2:27][CH2:26][C:10]2[N:11]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH:22]4[CH2:24][CH2:23]4)=[C:16]([F:25])[CH:15]=3)[O:13][C:9]=2[CH2:8]1)=[N+]=[N-].C1C[O:32][CH2:31][CH2:30]1>[C].[Pd]>[CH:22]1([CH2:21][O:20][C:17]2[CH:18]=[CH:19][C:14]([C:12]3[O:13][C:9]4[CH2:8][CH:7]([O:6][CH2:5][CH:4]([NH:1][C:31](=[O:32])[CH3:30])[CH3:28])[CH2:27][CH2:26][C:10]=4[N:11]=3)=[CH:15][C:16]=2[F:25])[CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 86731285HCID 86731285, compound

Product 1

HCID 86731284HCID 86731284, compound

Reagents, catalysts & solvents 1

HCID 178418390HCID 178418390, compoundCatalyst

Procedure

A mixture of 6-(2-azidopropoxy)-2-(4-(cyclopropylmethoxy)-3-fluorophenyl)-4,5,6,7-tetrahydro-1,3-benzoxazole (870 mg), 10% palladium-carbon (containing water (50%), 800 mg) and THF (10 mL) was stirred at room temperature for 10 min. 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 (725 mg).

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-3c3cb0733b404adaa3595f97dd01823a
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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