Semicarbazide hydrochloride → [(E)-[2-fluoro-4-[5-[(4S)-4-(5-fluoro-2-pyridinyl)-2-oxo-1,3-oxazolidin-3-yl]pyrazolo[1,5-a]pyrimidin-3-yl]phenyl]methylideneamino]urea

HRID 539133Notes

Reaction equation

HRID 539133 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([C:10]2[CH:11]=[N:12][N:13]3[CH:18]=[CH:17][C:16]([N:19]4[C@@H:23]([C:24]5[CH:29]=[CH:28][C:27]([F:30])=[CH:26][N:25]=5)[CH2:22][O:21][C:20]4=[O:31])=[N:15][C:14]=23)[CH:7]=[CH:6][C:3]=1[CH:4]=O.C([O-])(=O)C.[K+].Cl.[NH:38]([C:40]([NH2:42])=[O:41])[NH2:39]>CCO.CO>[F:1][C:2]1[CH:9]=[C:8]([C:10]2[CH:11]=[N:12][N:13]3[CH:18]=[CH:17][C:16]([N:19]4[C@@H:23]([C:24]5[CH:29]=[CH:28][C:27]([F:30])=[CH:26][N:25]=5)[CH2:22][O:21][C:20]4=[O:31])=[N:15][C:14]=23)[CH:7]=[CH:6][C:3]=1/[CH:4]=[N:39]/[NH:38][C:40]([NH2:42])=[O:41]

Participants

5

Reactant 3

HCID 11236Semicarbazide hydrochlorideHCID 517044Potassium AcetateHCID 86667831HCID 86667831, compound

Product 1

HCID 87243681[(E)-[2-fluoro-4-[5-[(4S)-4-(5-fluoro-2-pyridinyl)-2-oxo-1,3-oxazolidin-3-yl]pyrazolo[1,5-a]pyrimidin-3-yl]phenyl]methylideneamino]ureaYield 39%

Reagents, catalysts & solvents 1

HCID 18681192Ethanol, mixt. with methanolSolvent

Procedure

A solution of (S)-2-fluoro-4-(5-(4-(5-fluoropyridin-2-yl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)b enzaldehyde (0.370 g, 0.878 mmol), potassium acetate (0.0948 g, 0.966 mmol) and hydrazinecarboxamide hydrochloride (0.108 g, 0.966 mmol) in 3:1 EtOH/MeOH (6 mL) was stirred at ambient temperature overnight. The solvents were evaporated under vacuum. The residue was purified by preparative TLC (10% MeOH in DCM) to give (S,E)-2-(2-fluoro-4-(5-(4-(5-fluoropyridin-2-yl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzylidene)hydrazinecarboxamide (0.164 g, 39% yield) as a yellow powder.

Workup

  1. customThe solvents were evaporated under vacuum
  2. customThe residue was purified by preparative TLC (10% MeOH in DCM)

Sources & evidence

ORD record
ord-cb7226a54f524792943222cb7a5f6233
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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