1,2-Dichloroethane → HCID 118023955, compound

HRID 2171813Notes

Reaction equation

HRID 2171813 reaction equation
[CH:1]1([C:7]2[S:26][C:10]3[N:11]=[C:12]([CH3:25])[N:13]=[C:14]([CH2:15][N:16]4[C:21](=[O:22])[CH:20]5[CH2:23][CH2:24][CH:17]4[CH2:18][NH:19]5)[C:9]=3[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N1(CO)C2C=CC=C[C:30]=2N=N1.[Cl:38]CCCl.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>O>[ClH:38].[CH:1]1([C:7]2[S:26][C:10]3[N:11]=[C:12]([CH3:25])[N:13]=[C:14]([CH2:15][N:16]4[C:21](=[O:22])[CH:20]5[CH2:23][CH2:24][CH:17]4[CH2:18][N:19]5[CH3:30])[C:9]=3[CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 2241691H-Benzotriazole-1-methanolHCID 5049666Sodium triacetoxyborohydrideHCID 118023935HCID 118023935, compound

Product 1

HCID 118023955HCID 118023955, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-[(6-cyclohexyl-2-methylthieno[2,3-d]pyrimidin-4-yl)methyl]-2,5-diazabicyclo[2.2.2]octan-3-one (67 mg), 1H-benzotriazole-1-methanol (54 mg), and DCE was added NaBH(OAc)3 (115 mg) at room temperature, followed by stirring at the same temperature for 5 hours. To the reaction mixture was added water, followed by extraction with EtOAc. The organic layer was washed with brine, dried over Na2SO4, and then concentrated under reduced pressure. The residue was purified by basic silica gel column (hexane/EtOAc) and the obtained purified product was dissolved in EtOAc. An excess amount of 4 M HCl/EtOAc was added thereto, followed by concentration under reduced pressure. To the residue was added Et2O, followed by stirring, and the precipitate was collected by filtration to obtain 2-[(6-cyclohexyl-2-methylthieno[2,3-d]pyrimidin-4-yl)methyl]-5-methyl-2,5-diazabicyclo[2.2.2]octan-3-one hydrochloride (57 mg).

Workup

  1. extractionfollowed by extraction with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by basic silica gel column (hexane/EtOAc)
  6. customthe obtained purified product
  7. dissolutionwas dissolved in EtOAc
  8. additionAn excess amount of 4 M HCl/EtOAc was added
  9. concentrationfollowed by concentration under reduced pressure
  10. additionTo the residue was added Et2O
  11. stirringby stirring
  12. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-a374e7aa34b14f028f6f0e2b5a70a4a7
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

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