Propanal → HCID 66620938, compound

HRID 415150Notes

Reaction equation

HRID 415150 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][NH: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]>CO.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][N:9]2[CH2:26][CH2:27][CH3:28])[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

5

Reactant 2

HCID 527PropanalHCID 66621049HCID 66621049, compound

Product 1

HCID 66620938HCID 66620938, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-(2-fluoro-4-(piperidin-2-yl)phenyl)benzo[d]oxazole-7-carboxamide (200 mg, 0.44 mmol), 10% Pd/C (100 mg) and propanal (10 ml, 4 mmol) in methanol (10 ml) was hydrogenated at room temperature for two days. The solution was filtered off and concentrated; the residue was purified by prep-HPLC to give 2-(2-fluoro-4-(1-propylpiperidin-2-yl)phenyl)benzo[d]oxazole-7-carboxamide (94 mg, yield 43%). 1H-NMR (400 MHz, CD3OD) δ (ppm): 0.80 (s, 3H), 1.60-1.77 (m, 3H), 1.97-2.13 (m, 5H), 2.86 (s, 2H), 3.18 (s, 1H), 3.78-3.80 (m, 1H), 4.39-4.413 (m, 1H), 7.302-7.43 (m, 1H), 7.50-7.70 (m, 3H), 7.92-7.93 (m, 2H), 8.39 (s, 1H); LC-MS (ESI) m/z: 382 (M+1)+.

Workup

  1. filtrationThe solution was filtered off
  2. concentrationconcentrated
  3. customthe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-d42dbeebc22e4d79b6eec29b5897c338
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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