Hydrochloric Acid → HCID 23112237, compound

HRID 731964Notes

Reaction equation

HRID 731964 reaction equation
[CH3:1][N:2]1[C:7]2[CH:8]=[C:9]([NH:12][C:13]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[C:17]([CH2:27][N:28]4[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]4)[CH:16]=3)=[O:14])[CH:10]=[CH:11][C:6]=2S[CH2:4][C:3]1=[O:34].[Cl:35]C1C=CC=C(C(OO)=O)C=1.[S:46]([O-:49])(O)=[O:47].[Na+].Cl>CN(C)C(=O)C.C(OCC)(=O)C.O>[ClH:35].[CH3:1][N:2]1[C:7]2[CH:8]=[C:9]([NH:12][C:13]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)=[C:17]([CH2:27][N:28]4[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]4)[CH:16]=3)=[O:14])[CH:10]=[CH:11][C:6]=2[S:46](=[O:49])(=[O:47])[CH2:4][C:3]1=[O:34]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 70297m-Chloroperbenzoic acidHCID 23112248HCID 23112248, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 23112237HCID 23112237, compoundYield 23.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent2×HCID 31374DimethylacetamideSolvent

Procedure

In 5 ml of N,N-dimethylacetamide was dissolved 230 mg of N-(4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzothiazin-6-yl)-2-(piperidin-1-ylmethyl)biphenyl-4-carboxamide, and then 252 mg of m-chloroperbenzoic acid was added under ice cooling, followed by 24 hours of stirring at room temperature. To the reaction solution was added 5 ml of water and 1016 mg of sodium hydrogen sulfite as two divided portions, followed by 2 hours of stirring at room temperature. Water was added to the reaction system, the organic layer was extracted with ethyl acetate and dried over anhydrous sodium sulfate, and the solvent was removed by evaporation. The obtained residue was purified by silica gel column chromatography (chloroform:methanol:aqueous ammonia) to obtain a yellow oil. It was dissolved in 5 ml of ethyl acetate and then 1 ml of a 4M ethyl acetate solution of hydrochloric acid was added thereto. The solvent was removed by evaporation and the resulting solid was recrystallized from ethanol to obtain 61 mg of N-(4-methyl-1,1-dioxo-3-oxo-3,4-dihydro-2H-1,4-benzothiazin-6-yl)-2-(piperidin-1-ylmethyl)biphenyl-4-carboxamide hydrochloride as a white powder.

Workup

  1. waitfollowed by 2 hours
  2. stirringof stirring at room temperature
  3. extractionthe organic layer was extracted with ethyl acetate
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was removed by evaporation
  6. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol:aqueous ammonia)
  7. customto obtain a yellow oil
  8. customThe solvent was removed by evaporation
  9. customthe resulting solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-d5bc4fa456374aa496d85dccdac8209b
Source dataset
uspto-grants-2009_09
Patent number
US07585878B2

Reaction notes

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