Methanol → 6-(N-(1,2,4-thiadiazol-5-yl)sulfamoyl)-1-naphthoic acid

HRID 1473353Notes

Reaction equation

HRID 1473353 reaction equation
COC1C=C(OC)C=CC=1C[N:6]([C:24]1[S:28][N:27]=[CH:26][N:25]=1)[S:7]([C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[C:16]([C:20]([O:22]C)=[O:21])=[CH:15][CH:14]=[CH:13]2)(=[O:9])=[O:8].C(O)(C(F)(F)F)=O.CO.[OH-].[Li+]>C(Cl)Cl.C1COCC1.O>[S:28]1[C:24]([NH:6][S:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[C:16]([C:20]([OH:22])=[O:21])=[CH:15][CH:14]=[CH:13]3)(=[O:8])=[O:9])=[N:25][CH:26]=[N:27]1

Participants

8

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 6422Trifluoroacetic acidHCID 86687402methyl 6-(N-(2,4-dimethoxybenzyl)-N-(1,2,4-thiadiazol-5-yl)sulfamoyl)-1-naphthoate

Product 1

HCID 866874036-(N-(1,2,4-thiadiazol-5-yl)sulfamoyl)-1-naphthoic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 6-(N-(2,4-dimethoxybenzyl)-N-(1,2,4-thiadiazol-5-yl)sulfamoyl)-1-naphthoate (7.10 g, 14.21 mmol) was dissolved in 100 mL of DCM and TFA (10.95 ml, 142 mmol) was added. The reaction was stirred for 30 minutes at room temperature. The material was concentrated, dissolved in methanol, and re-concentrated to afford a light yellow solid. The solid was dissolved in THF (47.4 ml), methanol (47.4 ml), and water (47.4 ml). Lithium hydroxide (1.021 g, 42.6 mmol) was added and the reaction was stirred overnight at room temperature. The reaction was concentrated and dissolved in concentrated HCl solution. The solution was stirred for 5 minutes and filtered. The resulting white solid was washed with water, dried under a nitrogen blanket, and collected to afford 6-(N-(1,2,4-thiadiazol-5-yl)sulfamoyl)-1-naphthoic acid (Intermediate MM) as an off-white solid. m/z (ESI) 336.2 (M+H)+.

Workup

  1. concentrationThe material was concentrated
  2. dissolutiondissolved in methanol
  3. concentrationre-concentrated
  4. customto afford a light yellow solid
  5. stirringthe reaction was stirred overnight at room temperature
  6. concentrationThe reaction was concentrated
  7. dissolutiondissolved in concentrated HCl solution
  8. stirringThe solution was stirred for 5 minutes
  9. filtrationfiltered
  10. washThe resulting white solid was washed with water
  11. customdried under a nitrogen blanket
  12. customcollected

Sources & evidence

ORD record
ord-9e4420919db242b09f1944c977050cf9
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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