Nitrogen → [1-(5-Formyl-furan-2-ylmethyl)-1H-pyrazol-4-yl]-carbamic acid 2-chloro-benzyl ester

HRID 2064914Notes

Reaction equation

HRID 2064914 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[O:17][C:18]([CH2:21][OH:22])=[CH: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[O:17][C:18]([CH:21]=[O:22])=[CH:19][CH:20]=2)[CH:14]=1

Participants

5

Reactant 2

HCID 947NitrogenHCID 66928887[1-(5-Hydroxymethyl-furan-2-ylmethyl)-1H-pyrazol-4-yl]-carbamic acid 2-chloro-benzyl ester

Product 1

HCID 86650886[1-(5-Formyl-furan-2-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-(5-hydroxymethyl-furan-2-ylmethyl)-1H-pyrazol-4-yl]-carbamic acid 2-chloro-benzyl ester (300 mg, 0.83 mmol) in AcCN (8.0 mL) was treated at rt with MnO2 (400 mg, 4.15 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 yellow oil. LC-MS-conditions 02: tR=0.90 min; [M+H]+=360.28. 1H NMR (400 MHz, CDCl3) δ 5.32 (s, 5H), 6.47 (s, 1H), 6.64 (s, 1H), 7.20 (s, 1H), 7.30 (s, 1H), 7.37-7.45 (m, 1H), 7.45 (s, 2H), 7.79 (s, 1H), 9.63 (s, 1H).

Workup

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

Sources & evidence

ORD record
ord-b4025f58d27e40f6a96fe585b57d928f
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

Loading…