2-(4-(Pyridin-2-yl)phenyl)benzo[d]oxazole-7-carboxamide → 2-(4-(Piperidin-2-yl)phenyl)benzo[d]oxazole-7-carboxamide

HRID 415278Notes

Reaction equation

HRID 415278 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:14][C:15]3[C:21]([C:22]([NH2:24])=[O:23])=[CH:20][CH:19]=[CH:18][C:16]=3[N:17]=2)=[CH:9][CH:8]=1.[H][H]>CO.O.[Pt](=O)=O>[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:14][C:15]3[C:21]([C:22]([NH2:24])=[O:23])=[CH:20][CH:19]=[CH:18][C:16]=3[N:17]=2)=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 468302832-(4-(Pyridin-2-yl)phenyl)benzo[d]oxazole-7-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 666207342-(4-(Piperidin-2-yl)phenyl)benzo[d]oxazole-7-carboxamideYield 7.3%

Reagents, catalysts & solvents 2

HCID 11139377Platinum dioxide monohydrateCatalystHCID 887MethanolSolvent

Procedure

2-(4-(Pyridin-2-yl)phenyl)benzo[d]oxazole-7-carboxamide (100 mg, 0.3 mmol) and platinum (IV) oxide monohydrate (55 mg) in methanol (20 mL) was purged with 20 atm of hydrogen at 50° C. for 24 h. Then the mixture was filtered and adjusted to pH=9. The solvent was removed in vacuum. The crude was purified by pre-HPLC. 7 mg of 2-(4-(piperidin-2-yl)phenyl)benzo[d]oxazole-7-carboxamide was obtained. Yield: 7%. 1H-NMR (400 MHz, DMSO-d6) δ 1.23 (s, 1H), 1.56-1.70 (m, 4H), 1.87 (brs, 2H), 2.88-2.91 (m, 1H), 4.02-4.04 (m, 1H); 7.48-7.52 (m, 1H); 7.72-7.74 (m, 2H); 7.82-7.98 (m, 4H); 8.30-8.32 (d, J=7.2 Hz, 2H); LC-MS (m/z) 316 (M+1)+.

Workup

  1. filtrationThen the mixture was filtered
  2. customThe solvent was removed in vacuum
  3. customThe crude was purified by pre-HPLC

Sources & evidence

ORD record
ord-3ca099e5698d418497ad60c1ef66a09b
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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