Diisopropylethylamine → HCID 46202078, compound

HRID 1643475Notes

Reaction equation

HRID 1643475 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]2[CH2:19][CH2:20][CH2:21][S:22](Cl)(=[O:24])=[O:23])(=[O:12])=[O:11])=[C:5]([CH3:26])[CH:4]=1.[N:27]1[CH:32]=[CH:31][C:30]([N:33]2[CH2:38][CH2:37][C:36]3([CH2:43][CH2:42][NH:41][CH2:40][CH2:39]3)[CH2:35][CH2:34]2)=[CH:29][CH:28]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]2[CH2:19][CH2:20][CH2:21][S:22]([N:41]2[CH2:40][CH2:39][C:36]3([CH2:37][CH2:38][N:33]([C:30]4[CH:31]=[CH:32][N:27]=[CH:28][CH:29]=4)[CH2:34][CH2:35]3)[CH2:43][CH2:42]2)(=[O:24])=[O:23])(=[O:12])=[O:11])=[C:5]([CH3:26])[CH:4]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 159408113-(Pyridin-4-yl)-3,9-diazaspiro[5.5]undecaneHCID 59367806HCID 59367806, compound

Product 1

HCID 46202078HCID 46202078, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(1-(4-Methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)propane-1-sulfonyl chloride (1.3 mmol, 1 eq) in MC (5 ml) was added to a solution of 3-(pyridin-4-yl)-3,9-diazaspiro[5.5]undecane (1.56 mmol, 1.2 eq) and DIPEA (5.2 eq) at 0° C. and the mixture was stirred for 30 min. The reaction mixture was subsequently warmed to room temperature and stirred for 12 h. The reaction mixture was diluted with methylene chloride and washed with water and sat. sodium chloride solution. The organic phase was dried (Na2SO4) and concentrated in vacuo. The crude product obtained in this way was purified by column chromatography (silica gel). Yield: 0.4 g (50%). MS, Rt=3.8 min, m/z=614.9 [MH]+.

Workup

  1. stirringstirred for 12 h
  2. washwashed with water and sat. sodium chloride solution
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f563ede432ac410195a25a22715fb698
Source dataset
uspto-grants-2012_02
Patent number
US08119805B2

Reaction notes

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