4-Pyridinemethanamine → HCID 23122053, compound

HRID 1713533Notes

Reaction equation

HRID 1713533 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.Cl[C:19](OC1C=CC([N+]([O-])=O)=CC=1)=[O:20].[C:31]1([C:37]2([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[CH:41]3[CH2:42][NH:43][CH2:44][CH2:45][N:40]3[C:39](=[O:46])[O:38]2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>O1CCCC1>[O:46]=[C:39]1[N:40]2[CH2:45][CH2:44][N:43]([C:19]([NH:1][CH2:2][C:3]3[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=3)=[O:20])[CH2:42][CH:41]2[C:37]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)[O:38]1

Participants

6

Reactant 4

HCID 773174-PyridinemethanamineHCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 231218811,1-Diphenyltetrahydro-1H-oxazolo[3,4-a]pyrazin-3(5H)-one

Product 1

HCID 23122053HCID 23122053, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4-(Aminomethyl)pyridine (0.50 g, 4.6 mmol) was dissolved in tetrahydrofuran (5 mL). With ice cooling, diisopropylethylamine (1.5 mL) and 4-nitrophenyl chloroformate (1.0 g, 5.0 mmol) were added thereto, and the mixture was stirred at 0° C. for 30 minutes. Next, hexahydro-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazin-3-one (0.15 g, 0.51 mmol) was added thereto, and the resulting mixture was stirred for 16 hours while elevating the temperature from 0° C. to room temperature. The reaction solution was concentrated under reduced pressure, an aqueous saturated sodium hydrogen carbonate solution was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution and water, and concentrated under reduced pressure. The residue was purified with amino silica gel column chromatography (ethyl acetate) and powder was formed from hexane to obtain the title compound (0.12 g, yield 56%).

Workup

  1. stirringthe resulting mixture was stirred for 16 hours
  2. customfrom 0° C. to room temperature
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. additionan aqueous saturated sodium hydrogen carbonate solution was added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution and water
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified with amino silica gel column chromatography (ethyl acetate)
  9. custompowder was formed from hexane

Sources & evidence

ORD record
ord-0a70541d019d478c9655a15d90f8e458
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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