Hydrogen chloride-ethyl acetate → 5-Fluoro-1-methyl-1H-indole-2-sulfonic acid (2-methanesulfonyl-4-piperidin-4-yl-phenyl)-amide hydrochloride

HRID 1693130Notes

Reaction equation

HRID 1693130 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][S:21]([C:24]3[N:25]([CH3:34])[C:26]4[C:31]([CH:32]=3)=[CH:30][C:29]([F:33])=[CH:28][CH:27]=4)(=[O:23])=[O:22])=[C:16]([S:35]([CH3:38])(=[O:37])=[O:36])[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:39].C(OCC)(=O)C>CCOCC>[ClH:39].[CH3:38][S:35]([C:16]1[CH:15]=[C:14]([CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:19]=[CH:18][C:17]=1[NH:20][S:21]([C:24]1[N:25]([CH3:34])[C:26]2[C:31]([CH:32]=1)=[CH:30][C:29]([F:33])=[CH:28][CH:27]=2)(=[O:22])=[O:23])(=[O:37])=[O:36]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 597599644-[4-(5-Fluoro-1-methyl-1H-indole-2-sulfonylamino)-3-methanesulfonyl-phenyl]piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 249670395-Fluoro-1-methyl-1H-indole-2-sulfonic acid (2-methanesulfonyl-4-piperidin-4-yl-phenyl)-amide hydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 4-[4-(5-fluoro-1-methyl-1H-indole-2-sulfonylamino)-3-methanesulfonyl-phenyl]-piperidine-1-carboxylic acid tert-butyl ester (0.019 g) was treated with 2.5 N HCl/ethyl acetate (2.5 ml). The reaction mixture was stirred at rt for 3 h, then ether (20 ml) was added. The precipitate was collected, washed with ether and dried under high vacuum over P2O5 to produce the title compound (0.014 g) as an off-white amorphous powder. MS (ISN): 464.0 (M−H)−

Workup

  1. customThe precipitate was collected
  2. washwashed with ether
  3. dry with materialdried under high vacuum over P2O5

Sources & evidence

ORD record
ord-502df8c6ead4455bb40016696d5a237d
Source dataset
uspto-grants-2012_04
Patent number
US08158655B2

Reaction notes

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