Hydrochloric Acid → n-[1-{[4-(Aminomethyl)phenyl]methyl}-4-(methyloxy)-1h-indazol-3-yl]-5-chloro-2-thiophenesulfonamide formate salt

HRID 1892911Notes

Reaction equation

HRID 1892911 reaction equation
CC([N:5]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]2[C:25]3[C:20](=[C:21]([O:26][CH3:27])[CH:22]=[CH:23][CH:24]=3)[C:19]([NH:28][S:29]([C:32]3[S:33][C:34]([Cl:37])=[CH:35][CH:36]=3)(=[O:31])=[O:30])=[N:18]2)=[CH:12][CH:11]=1)[C:6](=[O:8])[O-:7])(C)C.Cl>ClCCl>[CH:6]([OH:8])=[O:7].[NH2:5][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][N:17]2[C:25]3[C:20](=[C:21]([O:26][CH3:27])[CH:22]=[CH:23][CH:24]=3)[C:19]([NH:28][S:29]([C:32]3[S:33][C:34]([Cl:37])=[CH:35][CH:36]=3)(=[O:31])=[O:30])=[N:18]2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 86661402HCID 86661402, compound

Product 1

HCID 66632574n-[1-{[4-(Aminomethyl)phenyl]methyl}-4-(methyloxy)-1h-indazol-3-yl]-5-chloro-2-thiophenesulfonamide formate saltYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl[(4-{[3-{[(5-chloro-2-thienyl)sulfonyl]amino}-4-(methyloxy)-1H-indazol-1-yl]methyl}phenyl)methyl]carbamate (for a preparation see Intermediate 29) (92 mg, 0.16 mmol) in dichloromethane (3 mL) was added dropwise hydrogen chloride (0.041 mL, 0.163 mmol). The resulting mixture was stirred at room temperature for 4 h, and then additional portion of hydrogen chloride (0.041 mL, 0.163 mmol) was added dropwise and the mixture was stirred at room temperature overnight. The solvents were then evaporated in a nitrogen blowdown unit. The residue was dissolved in 1:1 MeOH-DMSO (1 mL) and purified by Mass Directed AutoPrep (supelcosil ABZ+Plus column) eluting with solvents NB (A: Water+0.1% Formic acid, B: MeCN:Water 95:5+0.05% Formic acid). The solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus to give the title compound (69 mg, 83%). LCMS (System E) RT=2.10 min, ES+ve m/z 463/465 (M+H)+.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. customThe solvents were then evaporated in a nitrogen
  3. dissolutionThe residue was dissolved in 1:1 MeOH-DMSO (1 mL)
  4. custompurified by Mass Directed AutoPrep (supelcosil ABZ+Plus column)
  5. washeluting with solvents NB (A: Water+0.1% Formic acid, B
  6. customThe solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus

Sources & evidence

ORD record
ord-908fa2a0fa91463ba7ba52e025986e30
Source dataset
uspto-grants-2013_08
Patent number
US08507543B2

Reaction notes

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