4-Pyridinemethanamine → HCID 54550615, compound

HRID 361588Notes

Reaction equation

HRID 361588 reaction equation
Cl[CH2:2][C:3]([N:5]1[C@@H:11]2[CH2:12][CH2:13][CH2:14][C@@H:10]2[C:9](=[O:15])[N:8]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24](OC3C=CC=CC=3)=[O:25])=[CH:19][CH:18]=2)[C:7]2[CH:33]=[CH:34][CH:35]=[CH:36][C:6]1=2)=[O:4].[NH2:37][CH2:38][C:39]1[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=1.[C:45]1(=[O:55])[NH:49][C:48](=[O:50])[C:47]2=[CH:51][CH:52]=[CH:53][CH:54]=[C:46]12.[K]>CN(C=O)C.C(OCC)(=O)C.O>[C:45]1(=[O:55])[N:49]([CH2:2][C:3]([N:5]2[C@@H:11]3[CH2:12][CH2:13][CH2:14][C@@H:10]3[C:9](=[O:15])[N:8]([CH2:16][C:17]3[CH:18]=[CH:19][C:20]([NH:23][C:24]([NH:37][CH2:38][C:39]4[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=4)=[O:25])=[CH:21][CH:22]=3)[C:7]3[CH:33]=[CH:34][CH:35]=[CH:36][C:6]2=3)=[O:4])[C:48](=[O:50])[C:47]2=[CH:51][CH:52]=[CH:53][CH:54]=[C:46]12

Participants

7

Reactant 3

HCID 773174-PyridinemethanamineHCID 24194345Phthalimide potassium saltHCID 67767539HCID 67767539, compound

Product 1

HCID 54550615HCID 54550615, compoundYield 17.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of (3aR*,10aS*)-4-(Chloroacetyl)-9-[4-(phenoxycarbonylamino)benzyl]-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one (151 mg, 0.3 mmol) in DMF (1.5 mL) was added 4-(aminomethyl)pyridine (30 μL, 0.3 mmol) and the mixture was stirred at room temperature for 44 hours. This reaction mixture was diluted with ethyl acetate and water, and the aqueous layer was extracted with 2 portions of ethyl acetate. The pooled organic layer was washed with water and saturated aqueous NaCl solution, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was dissolved in DMF (2 mL) and after addition of potassium phthalimide (55 mg, 0.3 mmol), the mixture was stirred at room temperature for 90 hours. This reaction mixture was diluted with water and ethyl acetate and the aqueous layer was separated. The organic layer was washed with water and saturated aqueous NaCl solution, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform-methanol=20:1) to provide 33 mg (yield 17%) of the title compound. Amorphous.

Workup

  1. extractionthe aqueous layer was extracted with 2 portions of ethyl acetate
  2. washThe pooled organic layer was washed with water and saturated aqueous NaCl solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in DMF (2 mL)
  7. stirringthe mixture was stirred at room temperature for 90 hours
  8. customthe aqueous layer was separated
  9. washThe organic layer was washed with water and saturated aqueous NaCl solution
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure
  13. customThe residue was purified by silica gel column chromatography (chloroform-methanol=20:1)

Sources & evidence

ORD record
ord-e70cfb56187e4db083a56e90cbfbc61a
Source dataset
uspto-grants-1999_02
Patent number
US05866567

Reaction notes

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