Dichloromethane → HCID 59487293, compound

HRID 1925546Notes

Reaction equation

HRID 1925546 reaction equation
[CH:1]12[CH2:29][CH:4]([CH:5]([CH2:7][NH:8][C:9]([C:11]3[C:12]([S:17][CH2:18][CH2:19][C:20]([C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)=[O:21])=[N:13][CH:14]=[CH:15][CH:16]=3)=[O:10])[CH2:6]1)[CH2:3][CH2:2]2.[BH4-].[Na+].C(Cl)Cl.CCCCCC.CC(=O)OCC>CO>[CH:1]12[CH2:29][CH:4]([CH:5]([CH2:7][NH:8][C:9]([C:11]3[C:12]([S:17][CH2:18][CH2:19][CH:20]([C:22]4[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=4)[OH:21])=[N:13][CH:14]=[CH:15][CH:16]=3)=[O:10])[CH2:6]1)[CH2:3][CH2:2]2

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 21226206Ethyl acetate hexaneHCID 46909316HCID 46909316, compound2×

Product 1

HCID 59487293HCID 59487293, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 400 mg (0.97 mmol) of N-(5-bicyclo[2.2.1]heptanyl-methyl)-2-[[3-(4-fluorophenyl)-3-oxo-propyl]sulfanyl]-pyridine-3-carboxylic acid amide (exemplary compound 43) in MeOH (10 ml) was cooled to 0° C., and 18 mg (0.49 mmol) of NaBH4 were added in portions. Stirring was then carried out for 2 h at 0° C. and for 1 h at RT. The reaction solution was then poured onto ice-water and extraction with DCM was carried out. The organic phase was dried over MgSO4, filtered and concentrated in vacuo. CC (hexane/EA 2:1→1:1) of the residue yielded 180 mg (0.43 mmol, 45%) of N-(5-bicyclo[2.2.1]heptanyl-methyl)-2-[[3-(4-fluorophenyl)-3-hydroxy-propyl]sulfanyl]-pyridine-3-carboxylic acid amide. MS: m/z 415.2 [m+H]+.

Workup

  1. dry with materialThe organic phase was dried over MgSO4
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4c67c47e6bbb4ccab52108be92fbc916
Source dataset
uspto-grants-2012_05
Patent number
US08178684B2

Reaction notes

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