3-Pyridinemethanamine → HCID 178527132, compound

HRID 580875Notes

Reaction equation

HRID 580875 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]2[S:6](=[O:17])(=[O:16])[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[C:9](=S)[NH:10][C:4]=2[CH:3]=1.[NH2:20][CH2:21][C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1>C(OCCO)C>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]2[S:6](=[O:17])(=[O:16])[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[C:9]([NH:20][CH2:21][C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)=[N:10][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 310183-Pyridinemethanamine2×HCID 53986186HCID 53986186, compound

Product 1

HCID 178527132HCID 178527132, compound

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A solution of 0.46 g (1.5 mmol) of 8-chloro-5,5-dioxo-dibenzo[b,f]-1,4-thiazepin-11(10H)-thione in 15 mL of 2-ethoxyethanol was treated with 0.3 mL (3.0 mmol) of 3-(aminomethyl)pyridine and heated at reflux overnight. An additional 0.4 mL of 3-(aminomethyl)pyridine was added and the refluxing continued another night. The solvent was removed under reduced pressure and the residue taken up in EtOAc and washed three times with H2O, then saturated NaHCO3 solution and saturated NaCl solution. Drying over MgSO4 and removal of the solvent under reduced pressure left the crude product. Chromatography on silica gel, eluting with CHCl3 /MeOH (97/3) followed by precipitating the product from acetone with H2O gave an amorphous tan solid. The structure was confirmed by NMR and mass spectroscopy. (m+H)+ =384.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. waitthe refluxing continued another night
  4. customThe solvent was removed under reduced pressure
  5. washwashed three times with H2O
  6. dry with materialDrying over MgSO4 and removal of the solvent under reduced pressure
  7. waitleft the crude product
  8. washChromatography on silica gel, eluting with CHCl3 /MeOH (97/3)
  9. customby precipitating the product from acetone with H2O
  10. customgave an amorphous tan solid

Sources & evidence

ORD record
ord-633526d0f577479ab20f2fb4a88dfc3b
Source dataset
uspto-grants-1999_07
Patent number
US05919780

Reaction notes

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