Ammonia → HCID 12680078, compound

HRID 566299Notes

Reaction equation

HRID 566299 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=S)[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[C:6]=2[CH:19]=1.[NH3:20].CO>O1CCCC1>[NH2:20][C:10]1[CH2:9][N:8]=[C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[C:6]2[CH:19]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=2[N:11]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 126123797-Bromo-5-(pyridin-2-yl)-1,3-dihydro-2H-1,4-benzodiazepine-2-thione

Product 1

HCID 12680078HCID 12680078, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

59.5 g of 7-bromo-5-(2-pyridyl)-3H-1,4-benzodiazepine-2(1H)-thione (J. B. Hester, jr., A. D. Rudzik & P.F . Von Voigtlander, J. Med. Chem., 1980,23, 392-402) in 800 ml of tetrahydrofuran were added to 1.0 l of 25% aqueous ammonia solution and 300 ml of methanol. The mixture was stirred at room temperature for 16 h., with the solution which formed being concentrated to about 500 ml in a vacuum. The crystals were filtered off, washed with water and dried. There were obtained 52 g of 2-amino-7-bromo-5-(2-pyridyl)-3H-1,4-benzodiazepine which was used without further purification for the next step. A sample recrystallized from dioxan melted at 213-215° C. (dec.).

Workup

  1. customformed
  2. concentrationbeing concentrated to about 500 ml in a vacuum
  3. filtrationThe crystals were filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-b52a0081cab6486f9bc194e057778828
Source dataset
uspto-grants-2001_01
Patent number
US06174881B1

Reaction notes

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