Nitrogen → [1-(2-Formyl-thiazol-4-ylmethyl)-1H-pyrazol-4-yl]-carbamic acid 2-chloro-benzyl ester

HRID 2065024Notes

Reaction equation

HRID 2065024 reaction equation
N#N.[Cl:3][C:4]1[CH:27]=[CH:26][CH:25]=[CH:24][C:5]=1[CH2:6][O:7][C:8](=[O:23])[NH:9][C:10]1[CH:11]=[N:12][N:13]([CH2:15][C:16]2[N:17]=[C:18]([CH2:21][OH:22])[S:19][CH:20]=2)[CH:14]=1>C(C#N)(C)=O.O=[Mn]=O>[Cl:3][C:4]1[CH:27]=[CH:26][CH:25]=[CH:24][C:5]=1[CH2:6][O:7][C:8](=[O:23])[NH:9][C:10]1[CH:11]=[N:12][N:13]([CH2:15][C:16]2[N:17]=[C:18]([CH:21]=[O:22])[S:19][CH:20]=2)[CH:14]=1

Participants

5

Reactant 2

HCID 947NitrogenHCID 66928453HCID 66928453, compound

Product 1

HCID 86650890[1-(2-Formyl-thiazol-4-ylmethyl)-1H-pyrazol-4-yl]-carbamic acid 2-chloro-benzyl ester

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 694302-OxopropiononitrileSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of [1-(2-hydroxymethyl-thiazol-4-ylmethyl)-1H-pyrazol-4-yl]-carbamic acid 2-chloro-benzyl ester (230 mg, 0.61 mmol) in AcCN (6.0 mL) was treated at rt with MnO2 (293 mg, 3.04 mmol). The reaction mixture was stirred at rt overnight before being filtered through Celite and the solvent was removed under reduced pressure to give the title compound as a white solid. LC-MS-conditions 02: tR=0.96 min; [M+H]+=377.08.

Workup

  1. filtrationbefore being filtered through Celite
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f1f2e7e1af204879ab0a7ee3d9fd6646
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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