HCID 46847386, compound → HCID 44181679, compound

HRID 415283Notes

Reaction equation

HRID 415283 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[O:14][C:15]4[C:21]([C:22]([NH2:24])=[O:23])=[CH:20][CH:19]=[CH:18][C:16]=4[N:17]=3)=[CH:9][CH:8]=2)[CH:2]=1.[H][H]>CO.O.[Pt](=O)=O>[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[O:14][C:15]4[C:21]([C:22]([NH2:24])=[O:23])=[CH:20][CH:19]=[CH:18][C:16]=4[N:17]=3)=[CH:9][CH:8]=2)[CH2:2]1

Participants

5

Reactant 2

HCID 46847386HCID 46847386, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 44181679HCID 44181679, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 11139377Platinum dioxide monohydrateCatalystHCID 887MethanolSolvent

Procedure

2-(4-(Pyridin-3-yl)phenyl)benzo[d]oxazole-7-carboxamide (100 mg, 0.35 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. 11 mg of 2-(4-(piperidin-3-yl)phenyl)benzo[d]oxazole-7-carboxamide was obtained, yield: 11%. 1H-NMR (400 MHz, DMSO-d6) δ 1.45 (s, 3H), 1.74-1.77 (m, 2H), 1.89-1.96 (m, 2H), 2.87-2.90 (m, 1H), 3.06-3.09 (m, 2H), 7.85-7.90 (brs, 2H), 7.94-7.96 (d, J=8.0 Hz, 2H), 8.26-8.28 (d, J=8.2 Hz, 2H); LC-MS (ESI) 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-b31c22ebeebe4926971bca28991c9c00
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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