Acetic Acid → HCID 22246119, compound

HRID 890891Notes

Reaction equation

HRID 890891 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-eefa119240b24093b39723b2cb777253
Source dataset
uspto-grants-2006_02
Patent number
US06998415B2

Reaction notes

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