Hydrazine hydrate (1:1) → HCID 20097485, compound

HRID 1769874Notes

Reaction equation

HRID 1769874 reaction equation
[C:1]1([C:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]([CH2:18][C:19]3[N:23]([C:24]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[N:22]=[N:21][N:20]=3)[C:10](=[O:43])[CH:9]([N:44]3C(=O)C4=CC=CC=C4C3=O)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.NN>O1CCCC1>[NH2:44][CH:9]1[N:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]([CH2:18][C:19]2[N:23]([C:24]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[N:22]=[N:21][N:20]=2)[C:10]1=[O:43]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 20097471HCID 20097471, compound

Product 1

HCID 20097485HCID 20097485, compoundYield 51.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (3RS)-1,3-dihydro-5-phenyl-3-phthalimido-1-[(1-trityl-1H-tetrazol -5-yl)methyl]-2H-1,4-benzodiazepin-2-one (128 g) in tetrahydrofuran (2.56 l) was added hydrazine monohydrate (10.43 ml ) at room temperature. The mixture was stirred at 60° C. for 4 hours and the resultant precipitate was filtered off. The filtrate and the washings were evaporated in vacuo and the residue was dissolved in dichloromethane. After the insoluble material was filtered off, the solvent was evaporated in vacuo and the residue was dissolved in ethyl acetate and washed with 1N-sodium hydroxide solution and subsequently with water. The organic layer was dried over magnesium sulfate and filtered, and the filtrate was evaporated in vacuo to about 300 ml. The residue was stirred at room temperature. The resulting precipitates were collected by filtration to give (3RS)-3-amino-1,3-dihydro-5-phenyl-1-[(1-trityl-1H-tetrazol-5-yl)methyl]-2H-1,4-benzodiazepin-2-one (53.6 g).

Workup

  1. filtrationthe resultant precipitate was filtered off
  2. customThe filtrate and the washings were evaporated in vacuo
  3. dissolutionthe residue was dissolved in dichloromethane
  4. filtrationAfter the insoluble material was filtered off
  5. customthe solvent was evaporated in vacuo
  6. dissolutionthe residue was dissolved in ethyl acetate
  7. washwashed with 1N-sodium hydroxide solution and subsequently with water
  8. dry with materialThe organic layer was dried over magnesium sulfate
  9. filtrationfiltered
  10. customthe filtrate was evaporated in vacuo to about 300 ml
  11. stirringThe residue was stirred at room temperature
  12. customThe resulting precipitates
  13. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-d2d3b18d099445ad88ca6f12957a5866
Source dataset
uspto-grants-1995_01
Patent number
US05382664

Reaction notes

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