Sodium borohydride → HCID 57845311, compound

HRID 734843Notes

Reaction equation

HRID 734843 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]([C:16]#[C:17][C:18]3[CH:19]=[CH:20][C:21]([O:27][CH2:28][CH2:29][N:30]4[CH2:35][CH2:34][CH:33]([CH3:36])[CH2:32][CH2:31]4)=[C:22]([C:24](=[O:26])[CH3:25])[CH:23]=3)=[N:14][CH:15]=2)=[CH:6][CH:5]=1>O.CCO>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]([C:16]#[C:17][C:18]3[CH:19]=[CH:20][C:21]([O:27][CH2:28][CH2:29][N:30]4[CH2:31][CH2:32][CH:33]([CH3:36])[CH2:34][CH2:35]4)=[C:22]([CH:24]([OH:26])[CH3:25])[CH:23]=3)=[N:14][CH:15]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 11648530HCID 11648530, compound

Product 1

HCID 57845311HCID 57845311, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 30 mg (0.74 mmol) of sodium borohydride in 3 mL of water was added to a solution of 0.32 g (0.68 mmol) of 1-{5-[5-(4-chlorophenyl)pyridin-2-ylethynyl]-2-[2-(4-methylpiperidin-1-yl)ethoxy]phenyl}ethanone (Example 13.1) in 8 mL of EtOH and the mixture was stirred for 30 minutes at 50° C. The reaction mixture was evaporated down in vacuo, and the residue was stirred for 5 minutes with 4 mL of 1N aqueous HCl, diluted with EtOAc, and neutralized with saturated aqueous sodium bicarbonate solution. The phases were separated and the aqueous phase was extracted with EtOAc. The combined organic extracts were dried over magnesium sulfate and evaporated down in vacuo. The residue was triturated with acetonitrile and a little EtOAc, the precipitate was filtered off, and dried in the air. Yield: 100 mg (31% of theoretical); C29H31ClN2O2 (M=475.021); calc.: molpeak (M+H)+: 475/477 (Cl); found: molpeak (M+H)+: 475/477 (Cl); HPLC-MS: 5.20 minutes (method A).

Workup

  1. customThe reaction mixture was evaporated down in vacuo
  2. stirringthe residue was stirred for 5 minutes with 4 mL of 1N aqueous HCl
  3. additiondiluted with EtOAc
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with EtOAc
  6. dry with materialThe combined organic extracts were dried over magnesium sulfate
  7. customevaporated down in vacuo
  8. customThe residue was triturated with acetonitrile
  9. filtrationa little EtOAc, the precipitate was filtered off
  10. customdried in the air
  11. custom5.20 minutes (method A)

Sources & evidence

ORD record
ord-44a712ffbf2942318455f83d8ee2563b
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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