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

HRID 407347Notes

Reaction equation

HRID 407347 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-437a4f309a444028a4109a084dab1501
Source dataset
uspto-grants-2014_06
Patent number
US08754233B2

Reaction notes

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