Water → HCID 178420788, compound

HRID 580872Notes

Reaction equation

HRID 580872 reaction equation
[N:1]1[C:6]2[NH:7][C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[NH:10][C:11](=S)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[NH2:17][CH2:18][C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1.O>C(OCCO)C>[N:1]1[C:6]2[NH:7][C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[N:10]=[C:11]([NH:17][CH2:18][C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 310183-PyridinemethanamineHCID 53892560HCID 53892560, compound

Product 1

HCID 178420788HCID 178420788, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A solution of 0.5 g (2.2 mmol) of 6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepin-5-thione [(European Published Patent Application EP-393,604); C.A. 114, 143455] in 10 mL 2-ethoxyethanol was treated with 0.24 mL (10.8 mmol) of 3-(aminomethyl)pyridine and heated at reflux for 2 days. The mixture was poured into H2O and extracted with EtOAc. The EtOAc was 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 a gradient of CH2Cl2 /hexane (90/10) to CH2Cl2 /MeOH (94/6) gave 0.35 g (53% yield) of the product as a yellow solid, mp 192-194° C. The structure was confirmed by NMR and mass spectroscopy. (m+H)+ =302.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 days
  3. extractionextracted with EtOAc
  4. washThe EtOAc was washed three times with H2O
  5. dry with materialDrying over MgSO4 and removal of the solvent under reduced pressure
  6. waitleft the crude product
  7. washChromatography on silica gel, eluting with a gradient of CH2Cl2 /hexane (90/10) to CH2Cl2 /MeOH (94/6)

Sources & evidence

ORD record
ord-fec6ecb5de774059a5ae9c6fc5e9d84d
Source dataset
uspto-grants-1999_07
Patent number
US05919780

Reaction notes

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