Hydrochloric Acid → 2-(3-(Piperidin-4-yl)phenyl)benzo[d]oxazole-7-carboxamide

HRID 415305Notes

Reaction equation

HRID 415305 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:8]=[C:9]([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:10]=[CH:11][CH:12]=2)=[CH:3][CH:2]=1.[H][H].Cl>CO.O.[Pt](=O)=O>[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:8]=[C:9]([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:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 666209992-(3-(Pyridin-4-yl)phenyl)benzo[d]oxazole-7-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 666213882-(3-(Piperidin-4-yl)phenyl)benzo[d]oxazole-7-carboxamideYield 21.3%

Reagents, catalysts & solvents 2

HCID 11139377Platinum dioxide monohydrateCatalystHCID 887MethanolSolvent

Procedure

2-(3-(Pyridin-4-yl)phenyl)benzo[d]oxazole-7-carboxamide (110 mg, 0.35 mmol) and platinum (IV) oxide monohydrate in methanol 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 chromatography (dichloromethane:methanol=9:1) to give the solid. The solid was acidified by hydrochloride acid. 24 mg 2-(3-(piperidin-4-yl)phenyl)benzo[d]oxazole-7-carboxamide was obtained, yield: 21%. 1HNMR (400 MHz, DMSO-d6): δ 1.96 (m, 5H), 3.03 (m, 4H), 7.51 (m, 2H), 7.62 (t, 1H), 7.81 (d, J=6.4 Hz, 1H), 7.83 (brs, 1H), 7.94 (brs, 1H), 7.97 (d, J=6.4 Hz, 1H), 8.14 (s, 1H), 8.19 (d, J=6.4 Hz, 1H), 8.85 (brs, 1H), 9.02 (brs, 1H). LC-MS (ESI) m/z: 322 (M+1)+.

Workup

  1. filtrationThen the mixture was filtered
  2. customThe solvent was removed in vacuum
  3. customThe crude was purified by chromatography (dichloromethane:methanol=9:1)
  4. customto give the solid

Sources & evidence

ORD record
ord-03cc4a8d2ac149e4b1c5b55cd122259e
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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