HCID 66621653, compound → HCID 44181678, compound

HRID 415336Notes

Reaction equation

HRID 415336 reaction equation
[C:1]([C:4]1[C:12]2[O:11][C:10]([C:13]3[CH:32]=[CH:31][C:16]([CH2:17][CH2:18][N:19](C)[C:20](=O)OCC4C=CC=CC=4)=[CH:15][CH:14]=3)=[N:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])[NH2:2].[H][H]>CO.[Pd]>[CH3:20][NH:19][CH2:18][CH2:17][C:16]1[CH:31]=[CH:32][C:13]([C:10]2[O:11][C:12]3[C:4]([C:1]([NH2:2])=[O:3])=[CH:5][CH:6]=[CH:7][C:8]=3[N:9]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 66621653HCID 66621653, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 44181678HCID 44181678, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl 4-(7-carbamoylbenzo[d]oxazol-2-yl)phenethyl(methyl)carbamate (110 mg, 0.26 mmol), 10% Pd/C (20 mg) in methanol (20 ml) was stirred at room temperature over 1 atm hydrogen for 3 h. Then the mixture solution was filtered and the filtrate was evaporated under reduced pressure. The residue was purified by prep-HPLC to give 2-(4-(2-(methylamino)ethyl)phenyl)benzo[d]oxazole-7-carboxamide (20 mg, yield 26%). 1H-NMR (400 MHz, CD3OD) δ (ppm): 2.45 (s, 3H), 2.91-2.94 (m, 4H), 7.47-7.52 (m, 3 H), 7.88-7.92 (t, J=7.2 Hz, 2H), 8.26-8.28 (d, J=8.4 Hz, 2H). LC-MS (ESI) m/z: 296 (M+1)+.

Workup

  1. filtrationThen the mixture solution was filtered
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-8be5914b67e34068bfd1b95a96db46fd
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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