3-Iodobenzene-1-sulfonamide → 3-(4-{[6-(benzyl{(2R)-2-[4-(benzyloxy)-3-(formylamino)phenyl]-2-hydroxyethyl}amino)hexyl]oxy}but-1-ynyl)benzenesulfonamide

HRID 1825308Notes

Reaction equation

HRID 1825308 reaction equation
[CH2:1]([N:8]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][O:35][CH2:36][CH2:37][C:38]#[CH:39])[CH2:9][C@@H:10]([C:12]1[CH:13]=[CH:14][C:15]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:16]([NH:18][CH:19]=[O:20])[CH:17]=1)[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[C:41]1[CH:42]=[C:43]([S:47]([NH2:50])(=[O:49])=[O:48])[CH:44]=[CH:45][CH:46]=1>C(#N)C.C(N(CC)CC)C.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([N:8]([CH2:9][C@@H:10]([C:12]1[CH:13]=[CH:14][C:15]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[C:16]([NH:18][CH:19]=[O:20])[CH:17]=1)[OH:11])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][O:35][CH2:36][CH2:37][C:38]#[C:39][C:41]1[CH:42]=[C:43]([S:47]([NH2:50])(=[O:49])=[O:48])[CH:44]=[CH:45][CH:46]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 112198063-Iodobenzene-1-sulfonamideHCID 114439305-((1R)-2-{Benzyl[6-(but-3-ynyloxy)hexyl]amino}-1-hydroxyethyl)-2-(benzyloxy)phenylformamide

Product 1

HCID 426256683-(4-{[6-(benzyl{(2R)-2-[4-(benzyloxy)-3-(formylamino)phenyl]-2-hydroxyethyl}amino)hexyl]oxy}but-1-ynyl)benzenesulfonamideYield 51%

Reagents, catalysts & solvents 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

A stirred solution of 5-((1R)-2-{benzyl[6-(but-3-ynyloxy)hexyl]amino}-1-hydroxyethyl)-2-(benzyloxy)phenylformamide (500 mg) and 3-iodobenzenesulfonamide (340 mg) in acetonitrile (10 ml) and triethylamine (10 ml) with cuprous iodide (50 mg) and bis(triphenylphosphine) palladium dichloride (100 mg) was stirred at ambient temperature under nitrogen for 2 h. The mixture was evaporated in vacuo and the residue was purified by chromatography on Biotage (40 g) cartridge eluting with light petroleum 40-600/ethyl acetate (9:1) to give the title compound (330 mg). LCMS RT=3.04 min.

Workup

  1. customThe mixture was evaporated in vacuo
  2. customthe residue was purified by chromatography on Biotage (40 g) cartridge
  3. washeluting with light petroleum 40-600/ethyl acetate (9:1)

Sources & evidence

ORD record
ord-8825e80b97cf4326870742731f622316
Source dataset
uspto-grants-2006_05
Patent number
US07045658B2

Reaction notes

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