5-Methylthiophene-2-sulfonyl chloride → 4-[(4-(Methyloxy)-3-{[(5-methyl-2-thienyl)sulfonyl]amino}-1H-indazol-1-yl)methyl]benzamide

HRID 1892965Notes

Reaction equation

HRID 1892965 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:22]=[CH:21][C:17]([C:18]([NH2:20])=[O:19])=[CH:16][CH:15]=2)[N:3]=1.[CH3:23][C:24]1[S:28][C:27]([S:29](Cl)(=[O:31])=[O:30])=[CH:26][CH:25]=1>N1C=CC=CC=1>[CH3:12][O:11][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[C:2]([NH:1][S:29]([C:27]1[S:28][C:24]([CH3:23])=[CH:25][CH:26]=1)(=[O:31])=[O:30])=[N:3][N:4]2[CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:18]([NH2:20])=[O:19])=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 124001125-Methylthiophene-2-sulfonyl chlorideHCID 58054524HCID 58054524, compound

Product 1

HCID 594560464-[(4-(Methyloxy)-3-{[(5-methyl-2-thienyl)sulfonyl]amino}-1H-indazol-1-yl)methyl]benzamideYield 14%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 4-{[3-amino-4-(methyloxy)-1H-indazol-1-yl]methyl}benzamide (32.4 mg, 0.2 mmol) in pyridine 3.6 mL) was added to 5-methyl-thiophenesulfonyl chloride (for a preparation see Intermediate 32) (0.30 mmol). The reaction mixture was shaken briefly and allowed to stand for 3 h at 21° C. prior to concentration by blowdown. The residue was dissolved in 1:1 MeOH-DMSO (0.6 mL) and purified by Mass Directed AutoPrep on Xbridge column using Acetonitrile Water with an ammonium carbonate modifier (Method C). The solvent was evaporated in vacuo using the Genevac to give the title compound (12.5 mg, 14%). LCMS (System A) RT=0.86 min, ES+ve m/z 457 (M+H)+.

Workup

  1. concentrationto concentration by blowdown
  2. dissolutionThe residue was dissolved in 1:1 MeOH-DMSO (0.6 mL)
  3. custompurified by Mass Directed AutoPrep on Xbridge column
  4. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-adb7ebd703dc4449848fad4a110970c1
Source dataset
uspto-grants-2013_08
Patent number
US08507543B2

Reaction notes

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