Hydrazine → HCID 178486416, compound

HRID 2112544Notes

Reaction equation

HRID 2112544 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([CH3:21])[C:17]([O:19][CH3:20])=[CH:18][C:13]=2[NH:12][C:11](=S)[CH2:10][N:9]=1.C(OC(OCC)[N:27]([CH3:29])C)C.[NH2:33]N>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([CH3:21])[C:17]([O:19][CH3:20])=[CH:18][C:13]=2[N:12]=[C:11]2[NH:33][NH:27][CH:29]=[C:10]2[N:9]=1

Participants

4

Reactant 3

HCID 9321HydrazineHCID 70913Dimethylformamide diethylacetalHCID 576423175-(2-chlorophenyl)-1,3-dihydro-8-methoxy-7-methyl-2H-1,4-benzodiazepin-2-thione

Product 1

HCID 178486416HCID 178486416, compound

Procedure

5-(2-chlorophenyl)-1,2-dihydro-8-methoxy-7-methyl-pyrazolo[3,4-b][1,4]benzodiazepine (XXIIz) was prepared by reacting 0.003 moles of 5-(2-chlorophenyl)-1,3-dihydro-8-methoxy-7-methyl-2H-1,4-benzodiazepin-2-thione (IIz) with 1,1-diethoxy-N,N-dimethyl-methanamine and then hydrazine in a manner analogous to Example 90. Recrystallization from ethyl acetate-methanol provided 5-(2-chlorophenyl)-1,2-dihydro-8-methoxy-7-methyl-pyrazolo[3,4-b][1,4]benzodiazepine as a light red solid, mp 275-276° C.

Workup

  1. custom5-(2-chlorophenyl)-1,2-dihydro-8-methoxy-7-methyl-pyrazolo[3,4-b][1,4]benzodiazepine (XXIIz) was prepared
  2. customRecrystallization from ethyl acetate-methanol

Sources & evidence

ORD record
ord-c71a3c6586ad41eb8fe5f7a938d3e65d
Source dataset
uspto-grants-2009_04
Patent number
US07524840B2

Reaction notes

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