Hydrochloric Acid → HCID 44181679, compound

HRID 415321Notes

Reaction equation

HRID 415321 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].Cl>CO.[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

6

Reactant 3

HCID 313Hydrochloric AcidHCID 46847386HCID 46847386, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 44181679HCID 44181679, compoundYield 48.7%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

2-(4-(Pyridin-3-yl)phenyl)benzo[d]oxazole-7-carboxamide (550 mg, 1.66 mmol) and platinum (IV) oxide (110 mg) in methanol (100 ml) was hydrogenated under 20 atm of hydrogen at 50° C. for 24 h. Then the mixture was filtered and adjusted 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. 260 mg of 2-(4-(piperidin-3-yl)phenyl)benzo[d]oxazole-7-carboxamide was obtained. Yield: 47%. 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 (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-3e6d5d573fd74bb8b9b02e1d202e2d04
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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