Methanesulfonamide → N-[3-(4-Iodo-2-methyl-phenylamino)-pyridine-4-carbonyl]methanesulfonamide

HRID 218969Notes

Reaction equation

HRID 218969 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:17]=[N:16][CH:15]=[CH:14][C:10]=2[C:11](O)=[O:12])=[C:4]([CH3:18])[CH:3]=1.[CH3:19][S:20]([NH2:23])(=[O:22])=[O:21].C1CCN2C(=NCCC2)CC1>C1COCC1>[I:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:17]=[N:16][CH:15]=[CH:14][C:10]=2[C:11]([NH:23][S:20]([CH3:19])(=[O:22])=[O:21])=[O:12])=[C:4]([CH3:18])[CH:3]=1

Participants

5

Reactant 3

HCID 72879MethanesulfonamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 576496173-[(2-Methyl-4-iodophenyl)amino]isonicotinic acid

Product 1

HCID 57649648N-[3-(4-Iodo-2-methyl-phenylamino)-pyridine-4-carbonyl]methanesulfonamideYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

3-[(4-Iodo-2-methylphenyl)amino]isonicotinic acid (example 3) (50 mg, 0.141 mmol) was dissolved in 4 ml dry THF followed by the addition of 1,1″-carbonyldiimidazole (CDI) (0.311 mmol, 50 mg), methanesulfonamide (0.169 mmol, 16.1 mg) and DBU (0.169 mmol, 26 mg). The mixture was stirred for 16 h at 40° C. and the volatiles were removed in vacuo. The crude material was purified by preparative HPLC to give 20.3 mg (47 μmol; 33% yield) of pure desired product. LC-MS (method III): rt=2.74 min; m/z [M+H]+ 432.

Workup

  1. customthe volatiles were removed in vacuo
  2. customThe crude material was purified by preparative HPLC

Sources & evidence

ORD record
ord-5ea81e94d85e4ded9724ba9c98d5a950
Source dataset
uspto-grants-2012_06
Patent number
US08198457B2

Reaction notes

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