Hydrochloric Acid → HCID 66621183, compound

HRID 415299Notes

Reaction equation

HRID 415299 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([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:2]=1.[H][H].Cl>CO.O.[Pt](=O)=O>[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([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)[CH2:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 66621094HCID 66621094, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66621183HCID 66621183, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 11139377Platinum dioxide monohydrateCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-(3-(Pyridin-3-yl)phenyl)benzo[d]oxazole-7-carboxamide (110 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 chromatography (dichlormethane/methanol=9:1) to give the solid. The solid was acidified by hydrochloride acid and wash with ethyl acetate. The solvent was removed in vacuum. 11 mg of 2-(3-(piperidin-3-yl)phenyl)benzo[d]oxazole-7-carboxamide was obtained, yield: 10%. 1H-NMR (400 MHz, CD3OD) δ 1.93-1.97 (m, 2H), 2.12-2.14 (m, 2H), 3.07-3.27 (m, 3H), 3.51 (t, 2H), 7.53 (t, 1H); 7.60-7.63 (m, 2H), 7.91 (d, J=6.4 Hz, 1H); 7.94 (d, J=6.4 Hz, 1H); 8.26-8.29 (d, J=3.2 Hz, 1H). LC-MS (ESI) m/z: 321 (M+1)+.

Workup

  1. filtrationThen the mixture was filtered
  2. customThe solvent was removed in vacuum
  3. customThe crude was purified by chromatography (dichlormethane/methanol=9:1)
  4. customto give the solid
  5. washwash with ethyl acetate
  6. customThe solvent was removed in vacuum

Sources & evidence

ORD record
ord-da68974dccf543e5afd193d252bcf782
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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