Hydrazine hydrate (1:1) → HCID 19081154, compound

HRID 963473Notes

Reaction equation

HRID 963473 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([CH2:19][C:20]2[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][N:21]=2)[C:11](=[O:27])[CH:10]([N:28]2C(=O)C3=CC=CC=C3C2=O)[N:9]=1.O.NN>O1CCCC1>[NH2:28][CH:10]1[N:9]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([CH2:19][C:20]2[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][N:21]=2)[C:11]1=[O:27]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 19081220(3RS)-2,3-dihydro-5-(2-fluorophenyl)-1-(3-methylpyridin-2-yl)methyl-3-phtalimido-1H-1,4-benzodiazepin-2-one

Product 1

HCID 19081154HCID 19081154, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (3RS)-2,3-dihydro-5-(2-fluorophenyl)-1-(3-methylpyridin-2-yl)methyl-3-phtalimido-1H-1,4-benzodiazepin-2-one (1.24 g) in tetrahydrofuran (30 ml) was treated with a solution of hydrazine monohydrate (0.129 g) in tetrahydrofuran (5 ml) under stirring for 3 hours at room temperature and followed at 70° C. for 1 hour. The reaction mixture was allowed to cool to room temperature. The resultant precipitates were filtered off by suction and the filtrate was concentrated in vacuo. The residue was taken up with ethyl acetate and extracted with 1N aqueous hydrochloric acid. The aqueous layer was alkalined with sodium bicarbonate and extracted with chloroform twice. The extracts were dried over sodium sulfate, filtered and concentrated in vacuo to give (3RS)-3-amino-2,3-dihydro-5-(2-fluorophenyl)-1-(3-methylpyridin-2-yl)methyl-1H-1,4-benzodiazepin-2-one (0.87 g), which was used in a following reaction step without further purification.

Workup

  1. waitfollowed at 70° C. for 1 hour
  2. temperatureto cool to room temperature
  3. customThe resultant precipitates
  4. filtrationwere filtered off by suction
  5. concentrationthe filtrate was concentrated in vacuo
  6. extractionextracted with 1N aqueous hydrochloric acid
  7. extractionextracted with chloroform twice
  8. dry with materialThe extracts were dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c93660ccbc544441809d042c66d8c726
Source dataset
uspto-grants-1998_06
Patent number
US05763437

Reaction notes

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