Water → N-Cyclopropyl-4-methoxy-2,6-dimethyl-N-(2-(6-(9-(pyridin-4-yl)-3,9-diazaspiro[5.5]undecan-3-yl)pyrimidin-4-yloxy)ethyl)benzenesulfonamide

HRID 2387955Notes

Reaction equation

HRID 2387955 reaction equation
[H-].[Na+].[CH:3]1([N:6]([CH2:20][CH2:21][OH:22])[S:7]([C:10]2[C:15]([CH3:16])=[CH:14][C:13]([O:17][CH3:18])=[CH:12][C:11]=2[CH3:19])(=[O:9])=[O:8])[CH2:5][CH2:4]1.Cl[C:24]1[N:29]=[CH:28][N:27]=[C:26]([N:30]2[CH2:35][CH2:34][C:33]3([CH2:40][CH2:39][N:38]([C:41]4[CH:46]=[CH:45][N:44]=[CH:43][CH:42]=4)[CH2:37][CH2:36]3)[CH2:32][CH2:31]2)[CH:25]=1.O>O1CCCC1.C(OCC)(=O)C>[CH:3]1([N:6]([CH2:20][CH2:21][O:22][C:24]2[CH:25]=[C:26]([N:30]3[CH2:31][CH2:32][C:33]4([CH2:36][CH2:37][N:38]([C:41]5[CH:42]=[CH:43][N:44]=[CH:45][CH:46]=5)[CH2:39][CH2:40]4)[CH2:34][CH2:35]3)[N:27]=[CH:28][N:29]=2)[S:7]([C:10]2[C:15]([CH3:16])=[CH:14][C:13]([O:17][CH3:18])=[CH:12][C:11]=2[CH3:19])(=[O:9])=[O:8])[CH2:4][CH2:5]1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 43577600N-Cyclopropyl-N-(2-hydroxyethyl)-4-methoxy-2,6-dimethylphenylsulfonamideHCID 59401695HCID 59401695, compound

Product 1

HCID 46207142N-Cyclopropyl-4-methoxy-2,6-dimethyl-N-(2-(6-(9-(pyridin-4-yl)-3,9-diazaspiro[5.5]undecan-3-yl)pyrimidin-4-yloxy)ethyl)benzenesulfonamideYield 7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of sodium hydride (7.28 mmol, 10 equiv.) in tetrahydrofuran (10 ml) there was added, at 0° C., N-cyclopropyl-N-(2-hydroxyethyl)-4-methoxy-2,6-dimethylphenylsulfonamide (C-10) (0.8 mmol, 1.1 equiv.), followed by 3-(6-chloro-pyrimidin-4-yl)-9-(pyridin-4-yl)-3,9-diazaspiro[5.5]undecane (0.73 mmol, 1 equiv.). The reaction mixture was stirrred overnight at room temperature; water was then added and the mixture was diluted with ethyl acetate. The organic phase was extracted with water and saturated sodium chloride solution, dried (Na2SO4) and concentrated in vacuo. The crude product was purified by column chromatography (Alox-neutral). Yield: 7%. Rt=3.4 min; m/z=607.5 [MH]+

Workup

  1. additionwas added, at 0° C.
  2. extractionThe organic phase was extracted with water and saturated sodium chloride solution
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by column chromatography (Alox-neutral)

Sources & evidence

ORD record
ord-fdc62f7b7c2544b5af25e2e6180443b7
Source dataset
uspto-grants-2012_09
Patent number
US08269000B2

Reaction notes

Loading…