Pentanal → HCID 44181560, compound

HRID 415348Notes

Reaction equation

HRID 415348 reaction equation
[C:1]([C:4]1[C:12]2[O:11][C:10]([CH:13]3[CH2:18][CH2:17][N:16]([C:19](OCC4C=CC=CC=4)=O)[CH2:15][CH2:14]3)=[N:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])[NH2:2].[CH:29](=O)[CH2:30][CH2:31][CH2:32]C.[H][H]>CO.[Pd]>[CH2:19]([N:16]1[CH2:15][CH2:14][CH: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)[CH2:18][CH2:17]1)[CH2:29][CH2:30][CH2:31][CH3:32]

Participants

6

Reactant 3

HCID 8063PentanalHCID 66621374HCID 66621374, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 44181560HCID 44181560, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of compound benzyl 4-(7-carbamoylbenzo[d]oxazol-2-yl)piperidine-1-carboxylate (400 mg, 1.1 mmol), Pd/C (10% wt, 40 mg), pentanal (114 mg, 1.6 mmol) in anhydrous methanol (15 mL) was purged with hydrogen at room temperature for 12 hr. The mixture was filtered and the filtrate was concentrated to give the crude product. The crude product was purified by pre-HPLC to give the compound 2-(1-pentylpiperidin-4-yl)benzo[d]oxazol-7-carboxamide (44 mg, yield 14%). 1H-NMR (400 MHz, CDCl3) δ (ppm): 0.91-0.97 (m, 3H), 1.25-1.37 (m, 4H), 1.50-1.57 (m, 2H), 2.03-2.21 (m, 6H), 2.36-2.40 (m, 2H), 3.00-3.06 (m, 3H), 6.11 (s, 1H); 6.99 (s, 1H), 7.85-7.87 (t, 1H), 7.87-8.06 (m, 1H), 8.08 (dd, 1H); LC-MS (ESI) m/z: 316 (M+1)+.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customto give the crude product
  4. customThe crude product was purified by pre-HPLC

Sources & evidence

ORD record
ord-8d4ebcd3f28d44e2be9bf504028ed12b
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

Loading…