Ethanol → N-[(1S)-2-({5-[6-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]-1H-pyrazol-3-yl}oxy)-1-methylethyl]acetamide

HRID 1026224Notes

Reaction equation

HRID 1026224 reaction equation
C([N:8]1[C:12]([C:13]2[O:14][C:15]3[CH:21]=[C:20]([O:22][CH2:23][CH:24]4[CH2:26][CH2:25]4)[CH:19]=[CH:18][C:16]=3[N:17]=2)=[CH:11][C:10]([O:27][CH2:28][C@@H:29]([NH:31][C:32](=[O:34])[CH3:33])[CH3:30])=[N:9]1)C1C=CC=CC=1.C(O)C>[OH-].[OH-].[Pd+2].C1COCC1>[CH:24]1([CH2:23][O:22][C:20]2[CH:19]=[CH:18][C:16]3[N:17]=[C:13]([C:12]4[NH:8][N:9]=[C:10]([O:27][CH2:28][C@@H:29]([NH:31][C:32](=[O:34])[CH3:33])[CH3:30])[CH:11]=4)[O:14][C:15]=3[CH:21]=2)[CH2:25][CH2:26]1

Participants

5

Reactant 2

HCID 702EthanolHCID 67778187HCID 67778187, compound

Product 1

HCID 67777673N-[(1S)-2-({5-[6-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]-1H-pyrazol-3-yl}oxy)-1-methylethyl]acetamideYield 24.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Under a hydrogen atmosphere, a mixture of N-[(1S)-2-({1-benzyl-5-[6-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]-1H-pyrazol-3-yl}oxy)-1-methylethyl]acetamide (120 mg), 20% palladium hydroxide/carbon (containing water (50%), 60 mg), ethanol (5 mL) and THF (3 mL) was stirred at 50° C. for 4 hr. The catalyst was removed by filtration, and the obtained filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (23.4 mg).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe obtained filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-bb33dedafc3544a2af69efa787e0fd09
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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