Acetic Acid → HCID 22246119, compound

HRID 1839566Notes

Reaction equation

HRID 1839566 reaction equation
C1(COC([NH:11][CH2:12][CH2:13][C:14]2[O:15][C:16]([C:25]3[CH:30]=[CH:29][C:28]([S:31]([NH2:34])(=[O:33])=[O:32])=[CH:27][CH:26]=3)=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:18]=2)=O)C=CC=CC=1.C(O)(=O)C>CO.[Pd]>[NH2:11][CH2:12][CH2:13][C:14]1[O:15][C:16]([C:25]2[CH:30]=[CH:29][C:28]([S:31]([NH2:34])(=[O:33])=[O:32])=[CH:27][CH:26]=2)=[C:17]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:18]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 22246130HCID 22246130, compound

Product 1

HCID 22246119HCID 22246119, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-[2-[2-(N-phenylmethoxycarbonylamino)ethyl]-4-phenyl-oxazol-5-yl]benzenesulfonamide (Step 1) (0.75 g, 1.6 mmol) in MeOH (15 mL) containing acetic acid (0.1 mL) was treated with 10% Pd on carbon (0.35 g) and stirred under an atmosphere of hydrogen at 50 psi at room temperature for 2.5 h. The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure to afford a white powder which was purified by reverse-phase HPLC using a gradient of 10-90% CH3CN in H2O to afford 0.55 g of 4-[2-(2-aminoethyl)-4-phenyloxazol-5-yl]benzenesulfonamide as its trifluoroacetate salt: 1H NMR (CD3OD/300 MHz) δ 7.91 (d, 2H, J=7.9 Hz), 7.74 (m, 2H,), 7.63 (m, 2H), 7.44 (m, 3H), 3.49 (t, 2H, J=6.6 Hz), 3.33 (t, 2H, J=6.6 Hz). FABMS m/z =344 (M+H). HRMS calcd for C17H18N3O5S 344.1069. Found 344.1048.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto afford a white powder which
  4. customwas purified by reverse-phase

Sources & evidence

ORD record
ord-08475b4792d9446d8188ddf16bee796f
Source dataset
uspto-grants-2004_01
Patent number
US06677364B2

Reaction notes

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