Hydrazine hydrate (1:1) → HCID 19081234, compound

HRID 963474Notes

Reaction equation

HRID 963474 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH2:10][N:11]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[C:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[F:28])=[N:14][CH:13]([N:29]3C(=O)C4=CC=CC=C4C3=O)[C:12]2=[O:40])=[CH:2]1.O.NN>O1CCCC1>[NH2:29][CH:13]1[N:14]=[C:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[F:28])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N:11]([CH2:10][C:3]2[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[S:1][CH:2]=2)[C:12]1=[O:40]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 19081289HCID 19081289, compound

Product 1

HCID 19081234HCID 19081234, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3RS)-1-(benzothiophen-3-yl)methyl-2,3-dihydro-5-(2-fluorophenyl)-3-phtalimido-1H-1,4-benzodiazepin-2-one (0.980 g) in tetrahydrofuran (10 ml) was added dropwise hydrazine monohydrate (0.109 g) under stirring at ambient temperature. The mixture was stirred for 1 hour at the same temperature and refluxed under stirring for 2 hours. The reaction mixture was allowed to stand to ambient temperature. The resultant precipitates were filtered off and washed with tetrahydrofuran. The filtrate and washing were combined and concentrated in vacuo to afford a crude product. The crude product was purified by column chromatography on silica gel with an eluent of chloroform and methanol to afford (3RS)-3-amino-1-(benzothiophen-3-yl)methyl-2,3-dihydro-5-(2-fluorophenyl)-1H-1,4-benzodiazepin-2-one.

Workup

  1. stirringThe mixture was stirred for 1 hour at the same temperature
  2. temperaturerefluxed
  3. stirringunder stirring for 2 hours
  4. customto stand to ambient temperature
  5. customThe resultant precipitates
  6. filtrationwere filtered off
  7. washwashed with tetrahydrofuran
  8. washThe filtrate and washing
  9. concentrationconcentrated in vacuo
  10. customto afford a crude product
  11. customThe crude product was purified by column chromatography on silica gel with an eluent of chloroform and methanol

Sources & evidence

ORD record
ord-d5ed8241ee194e11a2448869cad8550c
Source dataset
uspto-grants-1998_06
Patent number
US05763437

Reaction notes

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