Hydrazine → 6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carbohydrazide

HRID 588151Notes

Reaction equation

HRID 588151 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8](Cl)=[O:9])[C:5]2[C:11]([O:33][CH3:34])=[N:12][N:13]([C:14]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:4]=2[CH:3]=1.[NH2:35][NH2:36]>C(#N)C>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([NH:35][NH2:36])=[O:9])[C:5]2[C:11]([O:33][CH3:34])=[N:12][N:13]([C:14]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 1182717656-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carbonyl chloride

Product 1

HCID 1182718816-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carbohydrazide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carbonyl chloride (240 mg, 0.491 mmol) was taken up in acetonitrile (4 ml). TEA (0.205 ml, 1.474 mmol) was added followed by the dropwise addition of hydrazine (0.046 ml, 1.474 mmol). The reaction was allowed to stir at rt overnight. The reaction mixture was concentrated in vacuo. The mixture was then resuspended in EtOAc and saturated NH4Cl was added. The products were extracted into EtOAc (3×) and the combined organics were washed with brine, dried over MgSO4, and concentrated in vacuo to give 6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carbohydrazide. The products were carried forward without further purification. MS: [M+H]+ m/z 484.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionsaturated NH4Cl was added
  3. extractionThe products were extracted into EtOAc (3×)
  4. washthe combined organics were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3db8a4fa2db344668a675398a70aa0f7
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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