HCID 66620506, compound → HCID 44181026, compound

HRID 415272Notes

Reaction equation

HRID 415272 reaction equation
[C:1]([C:4]1[C:12]2[O:11][C:10]([C:13]3([CH3:28])[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]>[CH3:28][C:13]1([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)[CH2:17][CH2:16][CH2:15][NH:14]1

Participants

5

Reactant 2

HCID 66620506HCID 66620506, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 44181026HCID 44181026, compoundYield 44.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl 2-(7-carbamoylbenzo[d]oxazol-2-yl)-2-methylpyrrolidine-1-carboxylate (144 mg, 0.37 mmol), 10% Pd/C (20 mg) in methanol (10 mL) was stirred at room temperature over 1 atm hydrogen for 3 h. Then the mixture was filtered and the filtrate was evaporated under reduced pressure. The residue was purified by flash chromatography. 40 mg of yellow oil of 2-(2-methylpyrrolidin-2-yl)benzo[d]oxazole-7-carboxamide was obtained, yield 43%. 1H-NMR (400 MHz, DMSO-d6): δ 1.58 (s, 3H), 1.76-1.87 (m, 3H), 2.47-2.49 (m, 1H), 2.86-2.91 (m, 1H), 2.97-3.02 (m, 1H), 7.41-7.44 (t, J=6.4 Hz, 1H), 7.69 (s, 1H), 7.74-7.76 (d, J=5.6 Hz, 1H), 7.82 (s, 1H), 8.85-8.87 (d, J=6.4 Hz, 1H). LC-MS (ESI) m/z: 246 (M+1)+.

Workup

  1. filtrationThen the mixture was filtered
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-3a02191ee8864d6c83a6e5ea4b57f9ff
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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