Hydrazine hydrate (1:1) → HCID 178473791, compound

HRID 2261685Notes

Reaction equation

HRID 2261685 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10](OS(C2C=CC(C)=CC=2)(=O)=O)=[C:11]([C:14]2[S:15][C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[N:18]=2)[C:12]#[N:13])[CH2:6][CH2:5]1)(=O)[CH3:2].[OH2:34].[NH2:35][NH2:36]>CO>[NH2:13][C:12]1[NH:36][N:35]=[C:10]([CH:7]2[CH2:8][CH2:9][N:4]([C:1](=[O:34])[CH3:2])[CH2:5][CH2:6]2)[C:11]=1[C:14]1[S:15][C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[N:18]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86608764HCID 86608764, compound

Product 1

HCID 178473791HCID 178473791, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of the above prepared toluene-4-sulfonic acid 1-(1-acetylpiperidin-4-yl)-2-benzothiazol-2-yl-2-cyanovinyl ester (140 mg, 0.29 mmol) and hydrazine hydrate (25 mg, 0.5 mmol) in methanol was refluxed overnight. The solvent was evaporated and the residue was purified by flash column chromatography eluting with CH2Cl2:MeOH=20:1 to yield 54 mg (55%) of 1-[4-(5-amino-4-benzothiazol-2-yl-1H-pyrazol-3-yl)-piperidin-1-yl]-ethanone. MS (ES+): 342.1 (M+1, 100%).

Workup

  1. additionA mixture of the
  2. temperaturewas refluxed overnight
  3. customThe solvent was evaporated
  4. customthe residue was purified by flash column chromatography
  5. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-6604d0053f4c4fef80d27dbe0c72ef31
Source dataset
uspto-grants-2010_12
Patent number
US07847101B2

Reaction notes

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