Potassium Hydroxide → HCID 58054397, compound

HRID 1892908Notes

Reaction equation

HRID 1892908 reaction equation
[OH-].[K+].[CH3:3][O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[C:7]([NH2:14])=[N:8][NH:9]2.ClC1SC(S(N(S(C2SC(Cl)=CC=2)(=O)=O)C2C3C(=CC=CC=3OC)N(C(OC(C)(C)C)=O)N=2)(=O)=O)=CC=1.Cl[CH2:53][C:54]1[CH:59]=[CH:58][C:57]([O:60][CH3:61])=[C:56]([O:62][CH3:63])[CH:55]=1>CS(C)=O.O>[CH3:63][O:62][C:56]1[CH:55]=[C:54]([CH2:53][N:9]2[C:10]3[C:6](=[C:5]([O:4][CH3:3])[CH:13]=[CH:12][CH:11]=3)[C:7]([NH2:14])=[N:8]2)[CH:59]=[CH:58][C:57]=1[O:60][CH3:61]

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 81740Veratryl chlorideHCID 185260534-Methoxy-1H-indazol-3-amineHCID 580544561,1-dimethylethyl 3-{bis[(5-chloro-2-thienyl)sulfonyl]amino}-4-(methyloxy)-1H-indazole-1-carboxylate

Product 1

HCID 58054397HCID 58054397, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Powdered KOH (0.494 g, 8.80 mmol) was dissolved in DMSO (20 mL) under nitrogen and 4-(methyloxy)-1H-indazol-3-amine (for a preparation see Intermediate 1) (0.653 g, 4 mmol) was added. The mixture was stirred for 15 min to give a deep red solution. 4-(Chloromethyl)-1,2-bis(methyloxy)benzene (0.896 g, 4.80 mmol) was added in one portion and the mixture was stirred for 2 h. The mixture was added to water (150 mL) and extracted with dichloromethane (3×50 mL). The dried (Na2SO4) extract was evaporated and the residue was triturated with diethyl ether (3×3 mL) to give the title compound (1.05 g, 84%) as an orange solid. LCMS (System B) RT=1.42 min, ES+ve m/z 314 (M+H)+.

Workup

  1. additionwas added
  2. customto give a deep red solution
  3. stirringthe mixture was stirred for 2 h
  4. extractionextracted with dichloromethane (3×50 mL)
  5. dry with materialThe dried (Na2SO4)
  6. extractionextract
  7. customwas evaporated
  8. customthe residue was triturated with diethyl ether (3×3 mL)

Sources & evidence

ORD record
ord-ad9e3683469b4b529f5c2afe25b19f41
Source dataset
uspto-grants-2013_08
Patent number
US08507543B2

Reaction notes

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