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

HRID 1984610Notes

Reaction equation

HRID 1984610 reaction equation
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.[Cl:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[S:14]([NH:17][C:18]1[CH:23]=[C:22]([CH:24]=[O:25])[C:21]([S:26][C:27]2[CH:32]=[CH:31][C:30]([S:33]([N:36]3[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]3)(=[O:35])=[O:34])=[CH:29][CH:28]=2)=[CH:20][N:19]=1)(=[O:16])=[O:15]>C1COCC1>[Cl:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[S:14]([NH:17][C:18]1[CH:23]=[C:22]([CH:24]([CH:1]2[CH2:3][CH2:2]2)[OH:25])[C:21]([S:26][C:27]2[CH:28]=[CH:29][C:30]([S:33]([N:36]3[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]3)(=[O:35])=[O:34])=[CH:31][CH:32]=2)=[CH:20][N:19]=1)(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 577182462,4-dichloro-N-{4-formyl-5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-pyridin-2-yl}-benzenesulfonamideHCID 178418630HCID 178418630, compound

Product 1

HCID 577182332,4-dichloro-N-{4-(cyclopropyl-hydroxy-methyl)-5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-pyridin-2-yl}-benzenesulfonamideYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of cyclopropylmagnesium bromide (0.5 M, 1.55 ml, 0.78 mmol) was added to a stirred solution of 2,4-dichloro-N-{4-formyl-5-[4-(piperidine-1-sulfonyl) -phenylsulfanyl]-pyridin-2-yl}-benzenesulfonamide (130 mg, 0.22 mmol) in THF (15 ml) and the mixture stirred for 2 hours. The reaction was concentrated under reduced pressure onto silica and the residue purified by flash column chromatography using ethyl acetate 1/1 hexane as eluent to afford 2,4-dichloro-N-{4-(cyclopropyl-hydroxy-methyl)-5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-pyridin-2-yl}-benzenesulfonamide as a green foam (74 mg, 54 %). 1H NMR (CDCl3): 8.40 (1H, s, py); 8.18 (1H, d, Ar); 7.51 (3H, m, py and Ar); 7.39 (1H, s, py); 7.34 (1H, d, Ar); 7.06 (2H, d, Ar); 4.50 (1H, d, CHOH); 2.89 (4H, m, 2×CH2N pip); 1.54 (4H, m, 2×CH2 pip); 1.34 (2H, m, CH2 pip); 0.97 (1H, m, CH cprop); 0.39 (4H, m, 2×CH2 cprop).

Workup

  1. concentrationThe reaction was concentrated under reduced pressure onto silica
  2. customthe residue purified by flash column chromatography

Sources & evidence

ORD record
ord-8dc9af8929fe48c492340651dfedaabb
Source dataset
uspto-grants-2009_06
Patent number
US07544702B2

Reaction notes

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