HCID 68696511, compound → HCID 68693934, compound

HRID 1990875Notes

Reaction equation

HRID 1990875 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([NH:12][C:13]2[O:14][C:15]3[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][C:16]=3[N:17]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[H][H]>C(O)C.[Pd]>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH2:8][CH:9]([NH:12][C:13]2[O:14][C:15]3[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][C:16]=3[N:17]=2)[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 68696511HCID 68696511, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68693934HCID 68693934, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 4-(5-nitro-benzooxazol-2-ylamino)-piperidine-1-carboxylic acid ethyl ester (2.0 g, 5.98 mmol, 1.0 equiv; intermediate L/step 3 (4-(5-nitro-benzooxazol-2-ylamino)-piperidine-1-carboxylic acid ethyl ester)) in ethanol (90 mL) was added palladium on activated charcoal 10% (0.2 g, 0.19 mmol, 0.03 equiv) and the reaction vessel filled with hydrogen (3.5 bar). After stirring at 40° C. for 18 h, the reaction mixture was filtered over celite, concentrated under reduced pressure and the residue purified with column chromatography on silica eluting with ethyl acetate/hexane (2:1) containing 5% methanol to yield 1.8 g (99%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 1.25 (t, J=7.1 Hz, 3H), 1.44-1.54 (m, 2H), 2.07-2.10 (m, 2H), 2.92-3.01 (m, 2H), 3.72 (br s, 1H), 3.88 (br s, 1H), 4.10 (br s, 1H), 4.14 (q, J=7.1 Hz, 2H), 6.33 (dd, J=8.4 Hz, J=2.2 Hz, 1H), 6.61 (br d, J=4.6 Hz, 1H), 6.67 (d, J=2.2 Hz, 1H), 6.97 (d, J=8.4 Hz, 1H). 13C NMR (75 MHz, CDCl3): δ 14.61, 32.13, 42.29, 50.18, 61.37, 102.92, 107.98, 108.53, 142.04, 143.49, 143.80, 155.46, 162.14. MS (ISP): 305.4 [M+H]+.

Workup

  1. filtrationthe reaction mixture was filtered over celite
  2. concentrationconcentrated under reduced pressure
  3. customthe residue purified with column chromatography on silica eluting with ethyl acetate/hexane (2:1)
  4. additioncontaining 5% methanol

Sources & evidence

ORD record
ord-81109d48ada149d6bc7217620891b436
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

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