Dimethyl Sulfoxide → HCID 57380313, compound

HRID 2174671Notes

Reaction equation

HRID 2174671 reaction equation
[OH:1][CH:2]([C:29]([NH:31][O:32][CH3:33])=[O:30])[CH:3]([NH:11][C:12](=[O:28])[C:13]1[CH:18]=[CH:17][CH:16]=[N:15][C:14]=1[N:19]1[CH:27]=[C:26]2[C:21]([CH:22]=[CH:23][CH:24]=[CH:25]2)=[N:20]1)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.CS(C)=O.IC1C=CC=CC=1C(O)=O.C([O-])(O)=O.[Na+]>ClCCl.O>[N:20]1[N:19]([C:14]2[N:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C:12]([NH:11][CH:3]([C:2](=[O:1])[C:29]([NH:31][O:32][CH3:33])=[O:30])[CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:28])[CH:27]=[C:26]2[C:21]=1[CH:22]=[CH:23][CH:24]=[CH:25]2

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 69412-Iodobenzoic acidHCID 516892Sodium BicarbonateHCID 86707231HCID 86707231, compound

Product 1

HCID 57380313HCID 57380313, compoundYield 92.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[3-hydroxy-4-(methoxyamino)-4-oxo-1-phenylbutan-2-yl]-2-(2H-indazol-2-yl)nicotinamide (1050 mg; 2.357 mmol) in DMSO (30 ml) 2-iodobenzoic acid (470 mg, 0.755 mmol) was added. After stirring for 4 hours at 30° C. additional 2-iodobenzoic acid (470 mg, 0.755 mmol) was added and stirring was continued for 3 hour at 30° C. and then overnight at room temperature. After cooling the reaction mixture to 15° C. a saturated aqueous solution of NaHCO3 (40 ml), water (40 ml) and dichloromethane (80 ml) were added. The organic layer was collected and the aqueous layer re-extracted twice with dichlormethane (CH2Cl2). The combined organic layers were then dried over MgSO4, filtered and concentrated to give 968 mg of a yellow-brown solid. Purification by chromatography over silica gel (eluent: CH2Cl2+0 to 10% (v/v) methanol) gave 800 mg of a raw product which was recrystallized from isopropanole yielding 456 mg of the title compound as a white solid.

Workup

  1. additionwas added
  2. customovernight
  3. customat room temperature
  4. additionwere added
  5. customThe organic layer was collected
  6. extractionthe aqueous layer re-extracted twice with dichlormethane (CH2Cl2)
  7. dry with materialThe combined organic layers were then dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-5e831dd6d241473e8f4aca261ea35b2b
Source dataset
uspto-grants-2015_06
Patent number
US09062027B2

Reaction notes

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