Acetic Anhydride → HCID 66725092, compound

HRID 559813Notes

Reaction equation

HRID 559813 reaction equation
[CH3:1][S:2]([C:5]1[CH:36]=[CH:35][C:8]([CH2:9][NH:10][C:11]([C:13]2[C:14](=[O:34])[N:15]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=3)[C:16]([CH3:23])=[C:17]([C:19](=[NH:22])[NH:20][OH:21])[CH:18]=2)=[O:12])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[C:37](OC(=O)C)(=O)[CH3:38]>C1(C)C=CC=CC=1>[CH3:1][S:2]([C:5]1[CH:36]=[CH:35][C:8]([CH2:9][NH:10][C:11]([C:13]2[C:14](=[O:34])[N:15]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:31])([F:33])[F:32])[CH:25]=3)[C:16]([CH3:23])=[C:17]([C:19]3[N:22]=[C:37]([CH3:38])[O:21][N:20]=3)[CH:18]=2)=[O:12])=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 178428723HCID 178428723, compound

Product 1

HCID 66725092HCID 66725092, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

5-(N-Hydroxycarbamimidoyl)-6-methyl-2-oxo-1-(3-trifluoromethyl-phenyl)-1,2-dihydro-pyridine-3-carboxylic acid 4-methanesulfonyl-benzylamide (0.011 g, 0.021 mmol), acetic anhydride (0.02 g, 0.195 mmol), toluene (2 ml) and a magnetic stirrer bar were placed in a vial. The vial was sealed and was heated (110° C.) with stirring for 5 h. LC-MS confirmed the consumption of the starting material and the formation of a product with the expected MW. Evaporation and purification on preparative HPLC gave the title compound (0.004 g, 35%) as a white solid after freeze-drying the pure fractions.

Workup

  1. customThe vial was sealed
  2. customthe consumption of the starting material
  3. customEvaporation and purification on preparative HPLC

Sources & evidence

ORD record
ord-0774f16f5b2e4879ad059e389c0b7902
Source dataset
uspto-grants-2011_11
Patent number
US08063073B2

Reaction notes

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