HCID 66621374, compound → HCID 66620732, compound

HRID 415256Notes

Reaction equation

HRID 415256 reaction equation
[C:1]([C:4]1[C:12]2[O:11][C:10]([CH:13]3[CH2:18][CH2:17][N:16](C(OCC4C=CC=CC=4)=O)[CH2:15][CH2:14]3)=[N:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])[NH2:2].[H][H]>CO.[Pd]>[NH:16]1[CH2:17][CH2:18][CH:13]([C:10]2[O:11][C:12]3[C:4]([C:1]([NH2:2])=[O:3])=[CH:5][CH:6]=[CH:7][C:8]=3[N:9]=2)[CH2:14][CH2:15]1

Participants

5

Reactant 2

HCID 66621374HCID 66621374, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66620732HCID 66620732, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl 4-(7-carbamoylbenzo[d]oxazol-2-yl)piperidine-1-carboxylate (98 mg, 0.26 mmol), 10% Pd/C (20 mg) in methanol (30 ml) was stirred at room temperature over 1 atm hydrogen for 2 hr. The mixture was filtered, and evaporated under reduced pressure. The residue was purified by pre-HPLC. 21 mg of 2-(piperidin-4-yl)benzo[d]oxazole-7-carboxamide as a solid was obtained, yield 33%. LCMS (ESI) m/z: 246 (M+1)+. 1H-NMR (400 MHz, DMSO-d6): δ 1.24 (brs, 1H), 1.71-1.74 (m, 2H), 2.03-2.06 (d, J=12 Hz, 2H), 2.64 (t, 2H), 3.01-3.04 (t, 2H), 3.14 (t, 1H), 7.41 (t, J=7.2 Hz, 1H), 7.72 (d, J=7.2 Hz, 1H), 7.72 (brs, 1H), 7.78 (brs, 1H), 7.85 (d, J=7.2 Hz, 1H).

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated under reduced pressure
  3. customThe residue was purified by pre-HPLC

Sources & evidence

ORD record
ord-d26aad2f07eb4fb99f65259c5e4e6af5
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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