Benzoic acid, 2-(chlorosulfonyl)-, methyl ester → HCID 58924311, compound

HRID 252211Notes

Reaction equation

HRID 252211 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:9])[CH:6]=[N:7][CH:8]=1.Cl[S:11]([C:14]1[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17])(=[O:13])=[O:12]>N1C=CC=CC=1.C([O-])(O)=O.[Na+]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][S:11]([C:14]2[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=2[C:16]([O:18][CH3:19])=[O:17])(=[O:13])=[O:12])[CH:6]=[N:7][CH:8]=1

Participants

5

Reactant 2

HCID 117830Benzoic acid, 2-(chlorosulfonyl)-, methyl esterHCID 127035955-Methoxypyridin-3-ylamine

Product 1

HCID 58924311HCID 58924311, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 5-methoxypyridin-3-amine (1 eq) in pyridine (0.4 M) was added methyl 2-(chlorosulfonyl)benzoate (1 eq) and the mixture was stirred overnight at room temperature. The mixture was diluted with saturated aqueous NaHCO3 and extracted with CH2Cl2. The organic layer was dried over Na2SO4, filtered and concentrated. The crude residue was purified by flash chromatography (0-8% MeOH/CH2Cl2) to give afford the title compound. 1H NMR (400 MHz, DMSO-D6) δ ppm 10.56-10.66 (m, 1H) 8.55-8.61 (m, 1H) 7.95-8.01 (m, 1H) 7.86-7.94 (m, 1H) 7.67-7.73 (m, 2H) 7.34-7.40 (m, 1H) 7.02 (s, 1H) 3.83 (s, 3H) 3.73 (s, 3H).

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue was purified by flash chromatography (0-8% MeOH/CH2Cl2)
  6. customto give

Sources & evidence

ORD record
ord-3996083006da4ce48dcc487bdfabd1c3
Source dataset
uspto-grants-2011_01
Patent number
US07868026B2

Reaction notes

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