Water → HCID 68107426, compound

HRID 2403624Notes

Reaction equation

HRID 2403624 reaction equation
C[O:2][CH2:3][CH2:4][CH2:5][OH:6].[H-].[Na+].C([O:13][C:14]([NH:16][CH2:17][C:18]([N:20]([CH2:22][C:23]1[CH:24]=[C:25]([C:29]2[CH:30]=[N:31][C:32]([N:35]3[CH2:40][CH2:39][N:38]([C:41]([O:43][C:44]4C=CC([N+]([O-])=O)=C[CH:45]=4)=[O:42])[CH2:37][CH2:36]3)=[N:33][CH:34]=2)[CH:26]=[CH:27][CH:28]=1)[CH3:21])=[O:19])=[O:15])(C)(C)C.[OH2:53].C1[CH2:58][O:57][CH2:56]C1>>[C:3]([C@@H:4]([C@H:5]([C:14]([OH:15])=[O:13])[OH:6])[OH:57])([OH:2])=[O:53].[NH2:16][CH2:17][C:18]([N:20]([CH2:22][C:23]1[CH:24]=[C:25]([C:29]2[CH:30]=[N:31][C:32]([N:35]3[CH2:40][CH2:39][N:38]([C:41]([O:43][CH2:44][CH2:45][CH2:56][O:57][CH3:58])=[O:42])[CH2:37][CH2:36]3)=[N:33][CH:34]=2)[CH:26]=[CH:27][CH:28]=1)[CH3:21])=[O:19]

Participants

6

Reactant 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 741163-Methoxy-1-propanolHCID 68106230HCID 68106230, compound

Product 1

HCID 68107426HCID 68107426, compound

Procedure

3-Methoxypropan-1-ol (88 mg) was dissolved in THF (3 ml), and NaH (60 mg) was added thereto, followed by stirring at room temperature for 10 minutes. 4-Nitrophenyl 4-{5-[3-({[N-(tert-butoxycarbonyl)glycyl](methyl)amino}methyl)phenyl]pyrimidin-2-yl}piperazine-1-carboxylate (250 mg) was added thereto, followed by stirring at room temperature for 1 hour. To the reaction mixture was added water, followed by extraction with EtOAc. The organic layer was dried over Na2SO4 and the solvent was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/EtOAc). The product was dissolved in EtOH, and 4 M hydrogen chloride/EtOAc was added thereto, followed by stirring at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and then a saturated aqueous sodium hydrogen carbonate solution was added thereto, followed by extraction with CHCl3. The organic layer was dried over Na2SO4 and the solvent was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (CHCl3/MeOH). The obtained residue was dissolved in EtOH, and L-tartaric acid (26 mg) was added thereto, followed by stirring at room temperature overnight. The precipitated solid was collected by filtration to obtain 3-methoxypropyl 4-[5-(3-{[glycyl(methyl)amino]methyl}phenyl)pyrimidin-2-yl]piperazine-1-carboxylate L-tartrate (60 mg).

Workup

  1. stirringby stirring at room temperature for 1 hour
  2. extractionfollowed by extraction with EtOAc
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationthe solvent was concentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane/EtOAc)
  6. dissolutionThe product was dissolved in EtOH
  7. addition4 M hydrogen chloride/EtOAc was added
  8. stirringby stirring at room temperature overnight
  9. concentrationThe reaction mixture was concentrated under reduced pressure
  10. additiona saturated aqueous sodium hydrogen carbonate solution was added
  11. extractionfollowed by extraction with CHCl3
  12. dry with materialThe organic layer was dried over Na2SO4
  13. concentrationthe solvent was concentrated under reduced pressure
  14. customThe residue was purified by silica gel column chromatography (CHCl3/MeOH)
  15. dissolutionThe obtained residue was dissolved in EtOH
  16. additionL-tartaric acid (26 mg) was added
  17. stirringby stirring at room temperature overnight
  18. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-642ec63b464646ca8d7c9400f3ce14bc
Source dataset
uspto-grants-2014_08
Patent number
US08802679B2

Reaction notes

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