HCID 58088119, compound → HCID 58088113, compound

HRID 1875876Notes

Reaction equation

HRID 1875876 reaction equation
Br[C:2]1[N:7]=[C:6]([NH:8][C:9]2[O:10][C:11]3([CH2:19][N:20]=2)[CH:16]2[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]2)[CH2:12]3)[CH:5]=[CH:4][CH:3]=1>CO.[Pd]>[N:7]1[CH:2]=[CH:3][CH:4]=[CH:5][C:6]=1[NH:8][C:9]1[O:10][C:11]2([CH2:19][N:20]=1)[CH:16]1[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]1)[CH2:12]2

Participants

4

Reactant 1

HCID 58088119HCID 58088119, compound

Product 1

HCID 58088113HCID 58088113, compoundYield 18.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To N-(6-bromopyridin-2-yl)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octan]-2-amine (291 mg, 0.86 mmol) in methanol (20 mL) was hydrogenated over 10% palladium on carbon (23 mg) in the Parr apparatus for 2 hours. The catalyst was removed by filtration and the filtrated concentrated in vacuo. The residue was purified by column chromatography (0.7% ammonium hydroxide/6.3% methanol/93% chloroform) to give racemic N-(pyridin-2-yl)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octan]-2-amine (41.3 mg, 0.16 mmol, 18.6 5 yield). 1H NMR (500 MHz, MeOD) δ ppm 8.13-8.33 (m, 1H), 7.57-7.72 (m, 1H), 6.83-7.04 (m, 2H), 3.97 (d, J=10.07 Hz, 1H), 3.66 (d, J=10.07 Hz, 1H), 3.18-3.27 (m, 1H), 3.03-3.14 (m, 1H), 2.94 (t, J=7.63 Hz, 2H), 2.70-2.90 (m, 2H), 2.06-2.24 (m, 2H), 1.57-1.87 (m, 3H). MS (LC/MS) R.T.=1.76; [M+H]+=259.25.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrated concentrated in vacuo
  3. customThe residue was purified by column chromatography (0.7% ammonium hydroxide/6.3% methanol/93% chloroform)

Sources & evidence

ORD record
ord-cc729ebcbb9c438baa54ea1c6e955c30
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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