Sodium Bicarbonate → HCID 57942210, compound

HRID 419178Notes

Reaction equation

HRID 419178 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C:15]2[C:16]([C:22]([C:24]3[CH:29]=[CH:28][N:27]=[C:26]([N:30]=CN(C)C)[CH:25]=3)=[O:23])=[N:17][CH:18]=[C:19]([CH3:21])[CH:20]=2)COC)(=[O:10])=[O:9])=[CH:4][C:3]=1[C:35]([F:38])([F:37])[F:36].C([O-])(O)=O.[Na+]>OS(O)(=O)=O.C(O)(C(F)(F)F)=O.O>[NH2:30][C:26]1[CH:25]=[C:24]([C:22]([C:16]2[C:15]([NH:11][S:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:35]([F:37])([F:38])[F:36])[CH:4]=3)(=[O:10])=[O:9])=[CH:20][C:19]([CH3:21])=[CH:18][N:17]=2)=[O:23])[CH:29]=[CH:28][N:27]=1

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 57942560HCID 57942560, compound

Product 1

HCID 57942210HCID 57942210, compoundYield 63.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 4-chloro-N-{2-[2-(dimethylamino-methyleneamino)-pyridine-4-carbonyl]-5-methyl-pyridin-3-yl}-N-methoxymethyl-3-trifluoromethyl-benzene sulfonamide (23 mg, mmol) in 5% H2SO4 in TFA (4 mL) and water (1 mL) was stirred at 50° C. for 2 days. The reaction mixture was cooled to room temperature, diluted with water (5 mL) and treated with saturated aqueous NaHCO3 solution slowly till pH 7-8. The mixture was extracted with EtOAc (2×25 mL), dried (anhydrous Na2SO4) and concentrated. The obtained residue was column purified (SiO2, 10% MeOH—CH2Cl2) to afford N-[2-(2-amino-pyridine-4-carbonyl)-5-methyl-pyridin-3-yl]-4-chloro-3-trifluoro methyl-benzenesulfonamide (12 mg) in 63% yield. 1H NMR (400 MHz, CDCl3) δ10.75 (s, 1H), 8.24 (s, 1H), 8.18 (m, 1H), 8.07 (dd, 1H), 7.95 (d, 1H), 7.75 (d, 1H), 7.63 (d, 1H), 7.15 (s, 1H), 6.95 (d, 1H), 2.25 (s, 3H); ESMS m/z (relative intensity): 471.0 (M+H)+ (100).

Workup

  1. extractionThe mixture was extracted with EtOAc (2×25 mL)
  2. dry with materialdried (anhydrous Na2SO4)
  3. concentrationconcentrated
  4. custompurified (SiO2, 10% MeOH—CH2Cl2)

Sources & evidence

ORD record
ord-efb08627ba914dc3817b51c5ec901c4b
Source dataset
uspto-grants-2012_01
Patent number
US08093247B2

Reaction notes

Loading…