Sodium hydride → HCID 86761178, compound

HRID 1714825Notes

Reaction equation

HRID 1714825 reaction equation
[H-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][CH2:7][N:8]1[C:13]2[CH:14]=[C:15]([CH2:18][O:19][CH:20]3[CH2:25][N:24]([S:26]([C:29]4[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=4)(=[O:28])=[O:27])[CH2:23][CH:22]([OH:36])[CH:21]3[C:37]3[CH:42]=[CH:41][C:40]([O:43][C:44]4[CH:54]=[CH:53][C:47]5[N:48]([CH3:52])[CH2:49][CH2:50][O:51][C:46]=5[CH:45]=4)=[CH:39][CH:38]=3)[CH:16]=[CH:17][C:12]=2[O:11][CH2:10][CH2:9]1.C1(C)C=CC(S(O[CH2:65][CH2:66][N:67]([CH3:78])[S:68]([C:71]2[CH:76]=[CH:75][C:74]([CH3:77])=[CH:73][CH:72]=2)(=[O:70])=[O:69])(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH3:3][O:4][CH2:5][CH2:6][CH2:7][N:8]1[C:13]2[CH:14]=[C:15]([CH2:18][O:19][CH:20]3[CH2:25][N:24]([S:26]([C:29]4[CH:30]=[CH:31][C:32]([CH3:35])=[CH:33][CH:34]=4)(=[O:27])=[O:28])[CH2:23][CH:22]([O:36][CH2:65][CH2:66][N:67]([CH3:78])[S:68]([C:71]4[CH:76]=[CH:75][C:74]([CH3:77])=[CH:73][CH:72]=4)(=[O:70])=[O:69])[CH:21]3[C:37]3[CH:42]=[CH:41][C:40]([O:43][C:44]4[CH:54]=[CH:53][C:47]5[N:48]([CH3:52])[CH2:49][CH2:50][O:51][C:46]=5[CH:45]=4)=[CH:39][CH:38]=3)[CH:16]=[CH:17][C:12]=2[O:11][CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 101216p-Toluenesulfonamide, N-(2-hydroxyethyl)-N-methyl-, p-toluenesulfonateHCID 516892Sodium BicarbonateHCID 68574628HCID 68574628, compound

Product 1

HCID 86761178HCID 86761178, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

95 mg of sodium hydride dispersion (60%) are added to a solution of 145 mg of 5-[4-(3-methoxypropyl)3,4 -dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-4-[4-(4-methyl-3,4-dihydro-2 H-benzo[1,4]oxazin-7-yloxy)phenyl]-1-(toluene-4-sulphonyl)piperidin-3-ol and 740 mg of 2-[methyl(toluene-4 -sulphonyl)amino]ethyl toluene-4-sulphonate in 5 ml of tetrahydrofuran while stirring at room temperature. The reaction mixture is stirred at 45° C. for 72 hours. The mixture is poured into 1M aqueous sodium bicarbonate solution (5 ml) and extracted with tert-butyl methyl ether (2×50 ml). The organic phases are washed successively with water (2×10 ml) and brine (1×10 ml), dried with sodium sulphate and evaporated. The title compound is obtained from the residue by flash chromatography (SiO2 60F). Rf=0.08 (EtOAc/heptane 1:1); Rt=5.83.

Workup

  1. stirringThe reaction mixture is stirred at 45° C. for 72 hours
  2. extractionextracted with tert-butyl methyl ether (2×50 ml)
  3. washThe organic phases are washed successively with water (2×10 ml) and brine (1×10 ml)
  4. dry with materialdried with sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-72a02e35fd06424f977fce91a86c9f54
Source dataset
uspto-grants-2010_09
Patent number
US07799779B2

Reaction notes

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