Hydrochloric Acid → HCID 69182107, compound

HRID 2373232Notes

Reaction equation

HRID 2373232 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH:26]=O)=[C:10]([CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:11]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=3)=[C:6]2[CH:5]=[N:4]1)[CH3:2].[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.C([BH3-])#N.[Na+].Cl.[OH-].[Na+]>CCO.CC(O)=O>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:26][N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[C:10]([CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:11]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=3)=[C:6]2[CH:5]=[N:4]1)[CH3:2]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 86602412HCID 86602412, compound

Product 1

HCID 69182107HCID 69182107, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

To a mixture of ethyl 3-[1-ethyl-6-formyl-4-(5-methyl-3-pyridyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]propanoate (30 mg), morpholine (36 μl) and AcOH (0.1 ml) in EtOH (1 ml) was added sodium cyanoborohydride (15 mg) at room temperature and stirred at room temperature for 5 hours. The reaction mixture was acidified to pH 3 with HCl and stirred for 30 minutes. The solution was neutralized with aqueous NaOH and extracted with EtOAc (×3). The organic layer was combined, washed with brine and dried over MgSO4. The solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel(CHCl3-MeOH 97:3) to give ethyl 3-[1-ethyl-4-(5-methyl-3-pyridyl)-6-(4-morpholinylmethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]propanoate (35 mg) as an oil.

Workup

  1. stirringstirred for 30 minutes
  2. extractionextracted with EtOAc (×3)
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed under reduced pressure
  6. customThe residue was purified by flash column chromatography on silica gel(CHCl3-MeOH 97:3)

Sources & evidence

ORD record
ord-9f9a7057bc60451eab5eb1c88f41be5f
Source dataset
uspto-grants-2008_12
Patent number
US07459451B2

Reaction notes

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