Benzyl 4-(4-carbamoylbenzo[d]oxazol-2-yl)benzyl(methyl)carbamate → 2-(4-((Methylamino)methyl)phenyl)benzo[d]oxazole-4-carboxamide

HRID 415177Notes

Reaction equation

HRID 415177 reaction equation
[C:1]([C:4]1[C:9]2[N:10]=[C:11]([C:13]3[CH:31]=[CH:30][C:16]([CH2:17][N:18](C)[C:19](=O)OCC4C=CC=CC=4)=[CH:15][CH:14]=3)[O:12][C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])[NH2:2]>C1COCC1.[Pd]>[CH3:19][NH:18][CH2:17][C:16]1[CH:15]=[CH:14][C:13]([C:11]2[O:12][C:8]3[C:9](=[C:4]([C:1]([NH2:2])=[O:3])[CH:5]=[CH:6][CH:7]=3)[N:10]=2)=[CH:31][CH:30]=1

Participants

4

Reactant 1

HCID 66621310Benzyl 4-(4-carbamoylbenzo[d]oxazol-2-yl)benzyl(methyl)carbamate

Product 1

HCID 441952612-(4-((Methylamino)methyl)phenyl)benzo[d]oxazole-4-carboxamideYield 69.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Benzyl 4-(4-carbamoylbenzo[d]oxazol-2-yl)benzyl(methyl)carbamate (0.050 g, 0.12 mmol) was dissolved in THF (10 mL) and 10% Pd/C (5.0 mg) was added, Hydrogen was purged into the mixture, and the mixture was maintained at room temperature for 6 hr, then the Pd/C was filtered off and the filtrate was condensed to get 2-(4-((methylamino)methyl)phenyl)benzo[d]oxazole-4-carboxamide (0.0212 g, 69.6% yield). 1H-NMR (400 MHz, DMSO-d6) δ 2.59 (s, 3H), 4.24-4.26 (t, J=5.0 Hz, 1H), 7.56-7.60 (t, J=8.0 Hz, 1H), 7.80-7.82 (d, J=8.0 Hz, 2H), 8.00-8.07 (m, 3H), 8.38-8.40 (d, J=8.0 Hz, 2H), 8.49 (s, 1H), 9.39 (s, 2H); LC-MS (ESI) m/z 282 [M+1]+.

Workup

  1. customHydrogen was purged into the mixture
  2. filtrationthe Pd/C was filtered off
  3. customcondensed

Sources & evidence

ORD record
ord-0fa23cd364e84e90b0e81fc7193f43cc
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

Loading…