Sodium borohydride → HCID 86653007, compound

HRID 242105Notes

Reaction equation

HRID 242105 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2([C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH2:23][CH2:24][NH:25][S:26]([CH2:29][CH2:30][CH3:31])(=[O:28])=[O:27])[CH:20]=4)[CH2:15][CH2:14][N:13]=3)[CH2:11][CH2:10][CH2:9]2)[CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2([CH:12]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH2:23][CH2:24][NH:25][S:26]([CH2:29][CH2:30][CH3:31])(=[O:27])=[O:28])[CH:20]=4)[CH2:15][CH2:14][NH:13]3)[CH2:9][CH2:10][CH2:11]2)[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86653006HCID 86653006, compound

Product 1

HCID 86653007HCID 86653007, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-[2-({1-[1-(6-Chloropyridin-2-yl)cyclobutyl]-3,4-dihydroisoquinolin-7-yl}oxy)ethyl]propane-1-sulfonamide (36 mg, 0.78 mmol) was dissolved in methanol (1 ml). Sodiumborohydride (12 mg, 0.31 mmol) was added and stirring was continued at room temperature over night. The solvent was evaporated in vacuo and the residue partitioned between dichloromethane and 1N aqueous sodium hydroxide solution. The layers were separated and the organic layer was dried (MgSO4) and concentrated in vacuo. The crude product was used for the next step without further purification. Yield: 9 mg.

Workup

  1. waitwas continued at room temperature over night
  2. customThe solvent was evaporated in vacuo
  3. customthe residue partitioned between dichloromethane and 1N aqueous sodium hydroxide solution
  4. customThe layers were separated
  5. dry with materialthe organic layer was dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude product was used for the next step without further purification

Sources & evidence

ORD record
ord-667cd085baa24d44ba289116fdbf151d
Source dataset
uspto-grants-2014_02
Patent number
US08653100B2

Reaction notes

Loading…