(R)-2-[3-(2-aminopropyl)-1H-indol-7-yloxy]-N,N-diethyl-acetamide → N,N-diethyl-2-{3-[(2R)-2-((2R)-2-hydroxy-2-pyridin-3-ylethylamino)propyl]-1H-indol-7-yloxy}-acetamide

HRID 1351920Notes

Reaction equation

HRID 1351920 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C@@H:7]2[CH2:9][O:8]2)[CH:2]=1.[NH2:10][C@H:11]([CH3:31])[CH2:12][C:13]1[C:21]2[C:16](=[C:17]([O:22][CH2:23][C:24]([N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])=[O:25])[CH:18]=[CH:19][CH:20]=2)[NH:15][CH:14]=1>O.C(O)C>[CH2:29]([N:26]([CH2:27][CH3:28])[C:24](=[O:25])[CH2:23][O:22][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]2[C:16]=1[NH:15][CH:14]=[C:13]2[CH2:12][C@H:11]([NH:10][CH2:9][C@H:7]([OH:8])[C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[CH3:31])[CH3:30]

Participants

5

Reactant 2

HCID 10968695(R)-2-[3-(2-aminopropyl)-1H-indol-7-yloxy]-N,N-diethyl-acetamideHCID 13319559(S)-3-Oxiranyl-pyridine

Product 1

HCID 69459174N,N-diethyl-2-{3-[(2R)-2-((2R)-2-hydroxy-2-pyridin-3-ylethylamino)propyl]-1H-indol-7-yloxy}-acetamideYield 21%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of (R)-(pyridin-3-yl)oxirane (97 mg, 0.80 mmol) and (R)-2-[3-(2-aminopropyl)-1H-indol-7-yloxy]-N,N-diethylacetamide (243 mg, 0.80 mmol) in water (0.8 mL) and ethanol (8 mL) is refluxed for 5 hours. After concentrated, the resulting residue is purified by preparative TLC (SiO2, 20×20 cm, 0.5 mm, iPrOH/saturated ammonia solution in chloroform=1/10) to give the desired N,N-diethyl-2-{3-[(2R)-2-((2R)-2-hydroxy-2-pyridin-3-ylethylamino)propyl]-1H-indol-7-yloxy}-acetamide (70 mg, yield: 21%).

Workup

  1. concentrationAfter concentrated
  2. customthe resulting residue is purified by preparative TLC (SiO2, 20×20 cm, 0.5 mm, iPrOH/saturated ammonia solution in chloroform=1/10)

Sources & evidence

ORD record
ord-4b13d74cde1b4070b2a9733be96fde97
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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