Benzyl 2-(7-carbamoylbenzo[d]oxazol-2-yl)pyrrolidine-1-carboxylate → 2-(Pyrrolidin-2-yl)benzo[d]oxazole-7-carboxamide

HRID 415251Notes

Reaction equation

HRID 415251 reaction equation
[C:1]([C:4]1[C:12]2[O:11][C:10]([CH:13]3[CH2:17][CH2:16][CH2:15][N:14]3C(OCC3C=CC=CC=3)=O)=[N:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])[NH2:2].[H][H]>CO.[Pd]>[NH:14]1[CH2:15][CH2:16][CH2:17][CH:13]1[C:10]1[O:11][C:12]2[C:4]([C:1]([NH2:2])=[O:3])=[CH:5][CH:6]=[CH:7][C:8]=2[N:9]=1

Participants

5

Reactant 2

HCID 66621188Benzyl 2-(7-carbamoylbenzo[d]oxazol-2-yl)pyrrolidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 441810272-(Pyrrolidin-2-yl)benzo[d]oxazole-7-carboxamideYield 13.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl 2-(7-carbamoylbenzo[d]oxazol-2-yl)pyrrolidine-1-carboxylate (68 mg, 0.19 mmol), 10% Pd/C (20 mg) in methanol (30 ml) was stirred at room temperature over 1 atm hydrogen for 2 hr. Then the mixture solution was filtered and the filtrate was evaporated under reduced pressure. The residue was purified by pre-HPLC to give 6 mg of 2-(pyrrolidin-2-yl)benzo[d]oxazole-7-carboxamide. Yield 13%. LC-MS (ESI) m/z: 232 (M+1)+. 1H-NMR (400 MHz, CDCl3): δ 1.24 (brs, 1H), 1.97 (m, 2H), 2.21 (m, 1H), 2.35 (m, 1H), 3.12 (m, 1H), 3.22 (m, 1H), 4.58 (m, 1H), 5.99 (brs, 1H), 7.03 (brs, 1H), 7.43-7.47 (t, J=8 Hz, 1H), 7.85-7.87 (d, J=8 Hz 1H), 8.08-8.09 (d, J=7.6 Hz, 1H).

Workup

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

Sources & evidence

ORD record
ord-10bfd39bac1149d685250adc72a434fe
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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