1,4-Dioxane hydrochloride → 2-(7-(aminomethyl)-1H-indol-1-yl)-1-(9-(pyridin-4-yl)-3,9-diazaspiro-[5.5]undecan-3-yl)ethanone

HRID 453919Notes

Reaction equation

HRID 453919 reaction equation
Cl.O1CCOCC1.[O:8]=[C:9]([N:29]1[CH2:34][CH2:33][C:32]2([CH2:39][CH2:38][N:37]([C:40]3[CH:45]=[CH:44][N:43]=[CH:42][CH:41]=3)[CH2:36][CH2:35]2)[CH2:31][CH2:30]1)[CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][C:18]=2[CH2:20][NH:21]C(=O)OC(C)(C)C)[CH:13]=[CH:12]1>O1CCOCC1>[NH2:21][CH2:20][C:18]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:19]=1[N:11]([CH2:10][C:9]([N:29]1[CH2:34][CH2:33][C:32]3([CH2:35][CH2:36][N:37]([C:40]4[CH:41]=[CH:42][N:43]=[CH:44][CH:45]=4)[CH2:38][CH2:39]3)[CH2:31][CH2:30]1)=[O:8])[CH:12]=[CH:13]2

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 59473707HCID 59473707, compound

Product 1

HCID 594736752-(7-(aminomethyl)-1H-indol-1-yl)-1-(9-(pyridin-4-yl)-3,9-diazaspiro-[5.5]undecan-3-yl)ethanoneYield 45%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Dioxane-HCl (6 ml) was added to a solution of tert-butyl (1-(2-oxo-2-(9-(pyridin-4-yl)-3,9-diazaspiro[5.5]undecan-3-yl)ethyl)-1H-indol-7-yl)methylcarbamate (600 mg, 1.16 mmol, 1.0 equiv.) in dioxane (6 ml), and the mixture was stirred for 1 h at RT. When the reaction was complete (TLC monitoring), the solvent was removed under vacuum and the residue was adjusted to a basic pH value with TEA and was concentrated again. The crude product was purified by column chromatography (Alox neutral; 5-10% MeOH/DCM), and the desired product was thus obtained in the form of a white solid.

Workup

  1. customthe solvent was removed under vacuum
  2. concentrationwas concentrated again
  3. customThe crude product was purified by column chromatography (Alox neutral; 5-10% MeOH/DCM)

Sources & evidence

ORD record
ord-32a1bb1840fd4fd3b2611a3924e472cb
Source dataset
uspto-grants-2013_07
Patent number
US08492559B2

Reaction notes

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