(S)-3-Oxiranyl-pyridine → 4-[5-(3-Cyclopentyl-propyl)-[1,2,4]oxadiazol-3-yl]-N-{4-[2-((R)-2-hydroxy-2-pyridin-3-yl-ethylamino)-ethyl]-phenyl}-benzenesulfonamide

HRID 1736428Notes

Reaction equation

HRID 1736428 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[N:24]=[C:23]([CH2:25][CH2:26][CH2:27][CH:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)[O:22][N:21]=3)=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:6][CH:5]=1.[N:33]1[CH:38]=[CH:37][CH:36]=[C:35]([C@@H:39]2[CH2:41][O:40]2)[CH:34]=1>CO>[OH:40][C@H:39]([C:35]1[CH:34]=[N:33][CH:38]=[CH:37][CH:36]=1)[CH2:41][NH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[N:24]=[C:23]([CH2:25][CH2:26][CH2:27][CH:28]4[CH2:29][CH2:30][CH2:31][CH2:32]4)[O:22][N:21]=3)=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 13319559(S)-3-Oxiranyl-pyridineHCID 19420583N-[4-(2-aminoethyl)phenyl]-4-[5-(3-cyclopentylpropyl)-[1,2,4]-oxadiazol-3-yl]benzensulfonamide

Product 1

HCID 120431564-[5-(3-Cyclopentyl-propyl)-[1,2,4]oxadiazol-3-yl]-N-{4-[2-((R)-2-hydroxy-2-pyridin-3-yl-ethylamino)-ethyl]-phenyl}-benzenesulfonamideYield 15%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of amine from Example 29 (0.053 g, 0.117 mmol) in dry methanol (30.0 ml) was added 3-pyridine epoxide from Example 16 (0.021 g, 0.175 mmol). The resulting solution was refluxed overnight. After concentration, the residue was purified by silica gel chromatography (13% methanol in methylene chloride) to give 0.01 g (15%) of the title compound: 1H NMR (400 MHz, CD3OD) δ8.52 (d, 1H, J=1.9 Hz), 8.42 (dd, 1H, J=1.5, 4.8 Hz), 8.13 (d, 2H, J=8.6 Hz), 7.85 (m, 3H), 7.40 (dd, 1H, J=4.8, 7.8 Hz), 7.10 (d, 1H, J=8.6 Hz), 7.03 (d, 2H, J=8.6 Hz), 4.81 (dd, 1H, J=4.9, 8.1 Hz), 2.96 (t, 2H, J=7.5 Hz), 2.93-2.70 (m, 6H), 1.90-1.72 (m, 5H), 1.68-2.48 (m, 4H), 1.42 (m, 2H), 1.11 (m, 2H).

Workup

  1. temperatureThe resulting solution was refluxed overnight
  2. concentrationAfter concentration
  3. customthe residue was purified by silica gel chromatography (13% methanol in methylene chloride)

Sources & evidence

ORD record
ord-74f0ee0b56f34d1db5a46d8a06b7a066
Source dataset
uspto-grants-1996_07
Patent number
US05541197

Reaction notes

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