Sodium hydride → HCID 11785343, compound

HRID 1951234Notes

Reaction equation

HRID 1951234 reaction equation
[H-].[Na+].[N:3]1([CH2:9][CH2:10][OH:11])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[CH2:12]([C:14]1[O:18][C:17]([CH2:19][CH2:20][NH:21][C:22]([NH:24][C:25]2[S:26][C:27]([C:31]3[CH:36]=[C:35]([CH3:37])[N:34]=[C:33](S(C)=O)[N:32]=3)=[C:28]([CH3:30])[N:29]=2)=[O:23])=[N:16][CH:15]=1)[CH3:13]>>[CH2:12]([C:14]1[O:18][C:17]([CH2:19][CH2:20][NH:21][C:22]([NH:24][C:25]2[S:26][C:27]([C:31]3[CH:36]=[C:35]([CH3:37])[N:34]=[C:33]([O:11][CH2:10][CH2:9][N:3]4[CH2:8][CH2:7][O:6][CH2:5][CH2:4]4)[N:32]=3)=[C:28]([CH3:30])[N:29]=2)=[O:23])=[N:16][CH:15]=1)[CH3:13]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 611632-MorpholinoethanolHCID 11281950HCID 11281950, compound

Product 1

HCID 11785343HCID 11785343, compound

Conditions

Temperature
70 °C

Procedure

Sodium hydride (0.020 mg, 0.50 mmol) is added to a stirred solution of 2-morpholin-4-yl-ethanol (0.084 ml, 0.69 mmol) and 1-[2-(5-ethyl-oxazol-2-yl)-ethyl]-3-[5-(2-methanesulfinyl-6-methyl-pyrimidin-4-yl)-4-methyl-thiazol-2-yl]-urea (Example 40) (0.10 g, 0.23 mmol). The reaction is heated at 70° C. for 8 hours then allowed to cool and filtered. The filtrate is evaporated and the residue is dissolved in DCM (50 ml) and washed with water (3×50 ml). The product is extracted into 1M HCl and the aqueous phase is washed with DCM. The aqueous phase is then basified with aq. NaOH and the product is re-extracted into DCM. After drying (MgSO4) the solvent is removed to give the titled compound.

Workup

  1. temperatureto cool
  2. filtrationfiltered
  3. customThe filtrate is evaporated
  4. dissolutionthe residue is dissolved in DCM (50 ml)
  5. washwashed with water (3×50 ml)
  6. extractionThe product is extracted into 1M HCl
  7. washthe aqueous phase is washed with DCM
  8. extractionthe product is re-extracted into DCM
  9. dry with materialAfter drying (MgSO4) the solvent
  10. customis removed

Sources & evidence

ORD record
ord-1709c21181b74440b74a64850905ddf8
Source dataset
uspto-grants-2013_03
Patent number
US08404684B2

Reaction notes

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