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

HRID 2065389Notes

Reaction equation

HRID 2065389 reaction equation
N#N.[Cl:3][C:4]1[CH:28]=[CH:27][CH:26]=[CH:25][C:5]=1[CH2:6][O:7][C:8](=[O:24])[NH:9][C:10]1[CH:11]=[N:12][N:13]([CH2:15][C:16]2[N:17]=[C:18]([CH:21]([OH:23])[CH3:22])[O:19][CH:20]=2)[CH:14]=1>C(C#N)(C)=O.O=[Mn]=O>[Cl:3][C:4]1[CH:28]=[CH:27][CH:26]=[CH:25][C:5]=1[CH2:6][O:7][C:8](=[O:24])[NH:9][C:10]1[CH:11]=[N:12][N:13]([CH2:15][C:16]2[N:17]=[C:18]([C:21](=[O:23])[CH3:22])[O:19][CH:20]=2)[CH:14]=1

Participants

5

Reactant 2

HCID 947NitrogenHCID 66928849{1-[2-(1-Hydroxy-ethyl)-oxazol-4-ylmethyl]-1H-pyrazol-4-yl}-carbamic acid 2-chloro-benzyl ester

Product 1

HCID 66928010[1-(2-Acetyl-oxazol-4-ylmethyl)-1H-pyrazol-4-yl]-carbamic acid 2-chloro-benzyl ester

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 694302-OxopropiononitrileSolvent

Conditions

Temperature
55 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of {1-[2-(1-hydroxy-ethyl)-oxazol-4-ylmethyl]-1H-pyrazol-4-yl}-carbamic acid 2-chloro-benzyl ester (211 mg, 0.56 mmol) in AcCN (5.0 mL) was treated at rt with MnO2 (270 mg, 2.80 mmol) and the reaction mixture was stirred at 55° C. for 3 h before being filtered through Celite. Purification of the residue by FC (2:1 to 1:2 hept-EA) gave the title compound as a pale yellow oil. TLC: rf (EA)=0.60. LC-MS-conditions 02: tR=0.94 min; [M+H]+=375.16.

Workup

  1. filtrationbefore being filtered through Celite
  2. customPurification of the residue by FC (2:1 to 1:2 hept-EA)

Sources & evidence

ORD record
ord-6d305a000351420489fb5c44e473ff9b
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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