2-(2-Fluoro-4-(pyridin-4-yl)phenyl)benzo[d]oxazole-7-carboxamide → 2-(2-Fluoro-4-(piperidin-4-yl)phenyl)benzo[d]oxazole-7-carboxamide

HRID 415346Notes

Reaction equation

HRID 415346 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH: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.[H][H]>CO.[Pt](=O)=O>[F:1][C:2]1[CH:7]=[C:6]([CH:8]2[CH2:9][CH2:10][NH:11][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

5

Reactant 2

HCID 441816742-(2-Fluoro-4-(pyridin-4-yl)phenyl)benzo[d]oxazole-7-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 441815622-(2-Fluoro-4-(piperidin-4-yl)phenyl)benzo[d]oxazole-7-carboxamideYield 32.7%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

2-(2-Fluoro-4-(pyridin-4-yl)phenyl)benzo[d]oxazole-7-carboxamide (300 mg, 0.9 mmol) and platinum (IV) oxide (150 mg) in methanol (20 mL) was purged with hydrogen (2.5 MPa) at 45° C. for two days. Then the mixture was filtered and the filtrate was concentrated. The crude was purified by prep-HPLC to obtain 2-(2-fluoro-4-(piperidin-4-yl)phenyl)benzo[d]oxazole-7-carboxamide (100 mg, yield 32%). 1H-NMR (400 MHz, CD3OD) δ (ppm): 1.93-2.03 (m, 2H), 2.15-2.18 (m, 2H), 2.94-3.20 (m, 3H), 3.52-3.55 (m, 2H), 7.32-7.37 (m, 2H), 7.51-7.55 (t, J=7.6 Hz, 1H), 7.93-7.95 (t, J=7.6 Hz, 2H), 8.29-8.33 (t, J=7.6 Hz, 1H); LC-MS (ESI) m/z: 340 (M+1)+.

Workup

  1. filtrationThen the mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe crude was purified by prep-HPLC

Sources & evidence

ORD record
ord-0ac781267aa6407d9325b9ad1f0acc67
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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