Diisopropylethylamine → N-(2-{3-[(2R)-2-((2R)-2-hydroxy-2-pyridin-3-ylethylamino)propyl]-1H-indol-7-yloxy}acetyl)methanesulfonamide

HRID 1351932Notes

Reaction equation

HRID 1351932 reaction equation
[NH2:1][C@H:2]([CH3:22])[CH2:3][C:4]1[C:12]2[C:7](=[C:8]([O:13][CH2:14][C:15]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])=[O:16])[CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.FC(F)(F)C([O-])=O.[N:30]1[CH:35]=[CH:34][CH:33]=[C:32]([C@@H:36]2[CH2:38][O:37]2)[CH:31]=1.CCN(C(C)C)C(C)C>C(#N)C>[OH:37][C@H:36]([C:32]1[CH:31]=[N:30][CH:35]=[CH:34][CH:33]=1)[CH2:38][NH:1][C@H:2]([CH3:22])[CH2:3][C:4]1[C:12]2[C:7](=[C:8]([O:13][CH2:14][C:15]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])=[O:16])[CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 84468TrifluoroacetateHCID 13319559(S)-3-Oxiranyl-pyridineHCID 69456022(R)-N-{2-[3-(2-aminopropyl)-1H-indol-7-yloxy]-acetyl}methanesulfonamide

Product 1

HCID 69712472N-(2-{3-[(2R)-2-((2R)-2-hydroxy-2-pyridin-3-ylethylamino)propyl]-1H-indol-7-yloxy}acetyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of (R)—N-{2-[3-(2-aminopropyl)-1H-indol-7-yloxy]-acetyl}methanesulfonamide.trifluoroacetate (40 mg, 0.091 mmol), (R)-(pyridin-3-yl)oxirane (48 mg, 0.36 mmol) and iPr2NEt (24 μL, 0.137 mmol) in acetonitrile (1 mL) is refluxed for 3 hours. After cooling, the mixture is concentrated and purified by preparative reversed phase HPLC (trifluoroacetic acid/water/acetonitrile) to give the desired N-(2-{3-[(2R)-2-((2R)-2-hydroxy-2-pyridin-3-ylethylamino)propyl]-1H-indol-7-yloxy}acetyl)methanesulfonamide.2 trifluoroacetate (3 mg, yield: 3%).

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture is concentrated
  3. custompurified by preparative reversed phase HPLC (trifluoroacetic acid/water/acetonitrile)

Sources & evidence

ORD record
ord-a447bf8daa8f42e1b7b3a9c9676a3f12
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

Loading…