Dimethyl Sulfoxide → 3-{[3-{[(5-Bromo-2-thienyl)sulfonyl]amino}-4-(methyloxy)-1H-indazol-1-yl]methyl}benzamide

HRID 1892952Notes

Reaction equation

HRID 1892952 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:11][CH3:12])[N:4]([CH2:13][C:14]2[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=2)[C:17]([NH2:19])=[O:18])[N:3]=1.[Br:23][C:24]1[S:28][C:27]([S:29](Cl)(=[O:31])=[O:30])=[CH:26][CH:25]=1.CS(C)=O>N1C=CC=CC=1>[Br:23][C:24]1[S:28][C:27]([S:29]([NH:1][C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][C:9]=3[O:11][CH3:12])[N:4]([CH2:13][C:14]3[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=3)[C:17]([NH2:19])=[O:18])[N:3]=2)(=[O:31])=[O:30])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 27339245-Bromothiophene-2-sulfonyl chlorideHCID 580544693-{[3-Amino-4-(methyloxy)-1H-indazol-1-yl]methyl}benzamide

Product 1

HCID 594560623-{[3-{[(5-Bromo-2-thienyl)sulfonyl]amino}-4-(methyloxy)-1H-indazol-1-yl]methyl}benzamideYield 12%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-{[3-Amino-4-(methyloxy)-1H-indazol-1-yl]methyl}benzamide (for a preparation see Intermediate 12) (22 mg, 0.07 mmol) was dissolved in pyridine (1.6 mL) and added to 5-bromo-2-thiophenesulfonyl chloride (27 mg, 0.1 mmol). The reaction mixture was shaken at room temperature for 5 min and then stood overnight at room temperature. DMSO (0.2 mL) was added to the reaction mixture and purified by MDAP on Atlantis column using Acetonitrile Water with a Formic acid modifier. The solvent was evaporated in vacuo using the Genevac to give the title compound (4.6 mg, 12%) LCMS (System A) RT=1.04 min, ES+ve m/z 521/523 (M+H)+.

Workup

  1. waitstood overnight at room temperature
  2. custompurified by MDAP on Atlantis column
  3. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-35f68ec473f147e085a35db3408bf397
Source dataset
uspto-grants-2013_08
Patent number
US08507543B2

Reaction notes

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