Hydrochloric Acid → 2-(2,4-Dichloro-benzenesulfonylamino)-5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-isonicotinic acid

HRID 1366855Notes

Reaction equation

HRID 1366855 reaction equation
C([O:6][C:7](=[O:42])[C:8]1[C:13]([S:14][C:15]2[CH:20]=[CH:19][C:18]([S:21]([N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)(=[O:23])=[O:22])=[CH:17][CH:16]=2)=[CH:12][N:11]=[C:10]([NH:30][S:31]([C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][C:35]=2[Cl:41])(=[O:33])=[O:32])[CH:9]=1)CCCC.O.[OH-].[Li+].Cl>C1COCC1.O>[Cl:41][C:35]1[CH:36]=[C:37]([Cl:40])[CH:38]=[CH:39][C:34]=1[S:31]([NH:30][C:10]1[CH:9]=[C:8]([C:13]([S:14][C:15]2[CH:16]=[CH:17][C:18]([S:21]([N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)(=[O:23])=[O:22])=[CH:19][CH:20]=2)=[CH:12][N:11]=1)[C:7]([OH:42])=[O:6])(=[O:33])=[O:32]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 57718221HCID 57718221, compound

Product 1

HCID 577182032-(2,4-Dichloro-benzenesulfonylamino)-5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-isonicotinic acidYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(2,4-dichloro-benzenesulfonylamino)-5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-isonicotinic acid pentyl ester (217 mg, 0.32 mmol) and lithium hydroxide monohydrate (54 mg, 1.3 mmol) in THF (15 ml) and water (15 ml) was stirred at 30° C. overnight. The reaction was diluted with water (25 ml), acidified to pH 1 with 1N HCl and extracted with ethyl acetate (2×30 ml). The combined extracts were dried (MgSO4) and concentrated under reduced pressure to give 2-(2,4-dichloro-benzenesulfonylamino)-5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-isonicotinic acid as a yellow solid (173 mg, 90%). 1H NMR (CDCl3): 8.06 (1 H, d, Ar); 7.96 (1 H, s, Ar); 7.82 (1 H, s, py); 7.67 (3 H, m, py and Ar); 7.39 (3 H, m, Ar); 2.94 (4 H, m, 2×CH2N pip); 1.56 (4 H, m, 2×CH2 pip); 1.39 (2 H, m, CH2 pip).

Workup

  1. extractionextracted with ethyl acetate (2×30 ml)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-55ba92c58ebe4bccabae61cb9dd1b72f
Source dataset
uspto-grants-2011_02
Patent number
US07893077B2

Reaction notes

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