Propanal → 2-(2-Fluoro-4-(1-propylpiperidin-4-yl)phenyl)benzo[d]oxazole-7-carboxamide

HRID 415347Notes

Reaction equation

HRID 415347 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:5]=[CH:4][C:3]=1[C:14]1[O:15][C:16]2[C:22]([C:23]([NH2:25])=[O:24])=[CH:21][CH:20]=[CH:19][C:17]=2[N:18]=1.[CH:26](=O)[CH2:27][CH3:28].[H][H]>CO.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([CH:8]2[CH2:9][CH2:10][N:11]([CH2:26][CH2:27][CH3:28])[CH2:12][CH2:13]2)[CH:5]=[CH:4][C:3]=1[C:14]1[O:15][C:16]2[C:22]([C:23]([NH2:25])=[O:24])=[CH:21][CH:20]=[CH:19][C:17]=2[N:18]=1

Participants

6

Reactant 3

HCID 527PropanalHCID 441815622-(2-Fluoro-4-(piperidin-4-yl)phenyl)benzo[d]oxazole-7-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 441815612-(2-Fluoro-4-(1-propylpiperidin-4-yl)phenyl)benzo[d]oxazole-7-carboxamideYield 10%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-(2-fluoro-4-(piperidin-4-yl)phenyl)benzo[d]oxazole-7-carboxamide (70 mg, 0.2 mmol), 10% Pd/C (30 mg) and propanal (5 mL, 2 mmol) in methanol (10 mL) was purged with hydrogen at room temperature for 2 days. The resulting solution was filtered and the filtrate was concentrated, the residue was purified by prep-HPLC to obtain 2-(2-fluoro-4-(1-propylpiperidin-4-yl)phenyl)benzo[d]oxazole-7-carboxamide (7.4 mg, yield 10%). 1H-NMR (400 MHz, CD3OD) δ (ppm): 1.03-1.08 (m, 3H), 1.80-1.86 (m, 2H), 2.01-2.04 (m, 2H), 2.20-2.24 (m, 2H), 3.07-3.18 (m, 5H), 3.72-3.75 (m, 2H), 7.32-7.37 (m, 2H), 7.52-7.56 (t, J=7.6 Hz, 1H), 7.94-7.97 (t, J=7.6 Hz, 2H), 8.30-8.34 (t, J=7.6 Hz, 1H); LC-MS (ESI) m/z: 382 (M+1)+.

Workup

  1. filtrationThe resulting solution was filtered
  2. concentrationthe filtrate was concentrated
  3. customthe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-012c0a67e28c4b57a745dcab611d867e
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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