2-Iodoxybenzoic acid → HCID 53245743, compound

HRID 2170874Notes

Reaction equation

HRID 2170874 reaction equation
[OH:1][CH:2]([C:31]([NH:33][O:34][CH3:35])=[O:32])[CH:3]([NH:11][C:12](=[O:30])[C:13]1[CH:18]=[CH:17][CH:16]=[N:15][C:14]=1[N:19]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N:20]1)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.I(C1C=CC=CC=1C(O)=O)(=O)=O.C([O-])(O)=O.[Na+]>CS(C)=O.ClCCl.O.CO>[CH3:35][O:34][NH:33][C:31](=[O:32])[C:2](=[O:1])[CH:3]([NH:11][C:12](=[O:30])[C:13]1[CH:18]=[CH:17][CH:16]=[N:15][C:14]=1[N:19]1[CH:23]=[CH:22][C:21]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[N:20]1)[CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

8

Reactant 3

HCID 1087942-Iodoxybenzoic acid3×HCID 516892Sodium BicarbonateHCID 86654643HCID 86654643, compound

Product 1

HCID 53245743HCID 53245743, compoundYield 95.4%

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-(3-hydroxy-4-(methoxyamino)-4-oxo-1-phenylbutan-2-yl)-2-(3-phenyl-1H-pyrazol-1-yl)nicotinamide (2000 mg, 4.24 mmol) in DMSO (25 ml) at 20° C. 2-iodoxybenzoic acid (IBX) (3959 mg, 6.36 mmol) was added. More IBX (400 mg, 0.643 mmol) was added 2 times over an interval of 2 h, the mixture was stirred overnight, another 500 mg of IBX were added and stirring was continued. After the reaction was completed (tlc: CH2Cl2+5% (v/v) methanol) 100 ml of a saturated solution of NaHCO3 was added dropwise, 200 ml of water and 200 ml of dichloromethane were then added and the precipitate was filtered off with suction. The dichloromethane layer was dried, filtered and concentrated to give 1.9 g of a yellowish amorphous solid, which was crystallized from ethyl acetate and dried in vacuo to give 1.1 g of the title compound. ESI-MS [M+H]+: 470.2

Workup

  1. customat 20° C
  2. stirringstirring
  3. additionwas added dropwise
  4. filtrationthe precipitate was filtered off with suction
  5. dry with materialThe dichloromethane layer was dried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9a8c6cb1faf74d0fb7ed22ce882103c1
Source dataset
uspto-grants-2015_06
Patent number
US09051304B2

Reaction notes

Loading…