Sodium Bicarbonate → 2,4-dichloro-N-{4-formyl-5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-pyridin-2-yl}-benzenesulfonamide

HRID 1984609Notes

Reaction equation

HRID 1984609 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[S:15]([NH:18][C:19]1[CH:20]=[C:21]([C:28]([S:31][C:32]2[CH:37]=[CH:36][C:35]([S:38]([N:41]3[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]3)(=[O:40])=[O:39])=[CH:34][CH:33]=2)=[CH:29][N:30]=1)[C:22](N(OC)C)=[O:23])(=[O:17])=[O:16].C([O-])(O)=O.[Na+]>C1COCC1.Cl>[Cl:7][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[S:15]([NH:18][C:19]1[CH:20]=[C:21]([CH:22]=[O:23])[C:28]([S:31][C:32]2[CH:33]=[CH:34][C:35]([S:38]([N:41]3[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]3)(=[O:40])=[O:39])=[CH:36][CH:37]=2)=[CH:29][N:30]=1)(=[O:17])=[O:16]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydrideHCID 577181912-(2,4-dichloro-benzenesulfonylamino)-N-methoxy-N-methyl-5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-isonicotinamide

Product 1

HCID 577182462,4-dichloro-N-{4-formyl-5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-pyridin-2-yl}-benzenesulfonamideYield 39%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (216 mg, 5.7 mmol) was added to a stirred solution of 2-(2,4-dichloro-benzenesulfonylamino)-N-methoxy-N-methyl-5-[4-(piperidine-1-sulfonyl) -phenylsulfanyl]-isonicotinamide (368 mg, 0.57 mmol) in THF (30 ml) and the reaction stirred for 90 minutes at room temperature. IN HCl solution (10 ml) was added cautiously and following 10 minutes of stirring NaHCO3 solution (40 ml) was added. The aqueous solution was extracted with ethyl acetate (2×40 ml), the combined extracts dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash column chromatography using ethyl acetate 2/3 hexane as eluent to afford 2,4-dichloro-N-{4-formyl-5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-pyridin-2-yl}-benzenesulfonamide as a yellow oil (130 mg, 39%). 1H NMR (CDCl3); 10.25 (1H, s, COH); 8.53 (1H, s, py); 8.17 (1H, d, Ar); 7.57 (2H, d, Ar); 7.51 (1H, s, Ar); 7.42 (2H, m, py and Ar); 7.21 (2H, d, Ar); 2.89 (4H, m, 2×CH2N pip); 1.55 (4H, m, 2×CH2 pip); 1.34 (2H, m, CH2 pip).

Workup

  1. additionwas added
  2. extractionThe aqueous solution was extracted with ethyl acetate (2×40 ml)
  3. dry with materialthe combined extracts dried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-449e64e3f3934fb4b54ca8d36bb02162
Source dataset
uspto-grants-2009_06
Patent number
US07544702B2

Reaction notes

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