Hydrochloric Acid → HCID 66621492, compound

HRID 415288Notes

Reaction equation

HRID 415288 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([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: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: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)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 46847387HCID 46847387, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66621492HCID 66621492, compoundYield 3.3%

Reagents, catalysts & solvents 2

HCID 11139377Platinum dioxide monohydrateCatalystHCID 887MethanolSolvent

Procedure

2-(4-(Pyridin-4-yl)phenyl)benzo[d]oxazole-7-carboxamide (135 mg, 0.43 mmol) and platinum (IV) oxide monohydrate (70 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 chromatography (dichloromethane:methanol=8:1) to give the solid. The solid was acidified by hydrochloride acid. 4.6 mg of 2-(4-(piperidin-4-yl)phenyl)benzo[d]oxazole-7-carboxamide was obtained. Yield: 3%. 1H-NMR (400 MHz, CD3OD-d4) δ 1.89 (m, 2H), 2.03 (m, 2H), 2.95 (m, 1H), 3.09-3.12 (m, 2H), 3.43-3.46 (m, 2H), 7.40-7.46 (m, 3H), 7.81 (t, J=8.4 Hz, 2H), 8.21 (d, J=8.0 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 chromatography (dichloromethane:methanol=8:1)
  4. customto give the solid

Sources & evidence

ORD record
ord-bc809061fcd14d37835390c77d2654ff
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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