1-Bromopropane → HCID 23135147, compound

HRID 475508Notes

Reaction equation

HRID 475508 reaction equation
[CH2:1]([N:8]1[C:12]2[CH2:13][CH:14]([OH:16])[CH2:15][C:11]=2[C:10]([C:17]#[N:18])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:21](Br)[CH2:22][CH3:23]>CN(C=O)C>[CH2:1]([N:8]1[C:12]2[CH2:13][CH:14]([O:16][CH2:21][CH2:22][CH3:23])[CH2:15][C:11]=2[C:10]([C:17]#[N:18])=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 78401-Bromopropane2×HCID 24758Sodium hydride2×HCID 23135152HCID 23135152, compound

Product 1

HCID 23135147HCID 23135147, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-benzyl-5-hydroxy-1,4,5,6-tetrahydrocyclo-penta[c]pyrazole-3-carbonitrile-(see Example 9.7, 30 mg, 0.125 mmol) in anhydrous DMF (2 mL) was added sodium hydride (6 mg, 0.15 mmol, 60% dispersion in oil). After stirring for 3 minutes propyl bromide was added (14 μL, 0.15 mmol) and the resulting mixture stirred for an hour. At the end of this time sodium hydride (6 mg, 0.15 mmol, 60% dispersion in oil) and propyl bromide were added. After 30 minutes the reaction was quenched by adding saturated NH4Cl (3 mL). The resulting mixture was extracted with ethyl acetate, washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by PTLC (SiO2) using 15% ethyl acetate-hexanes to give the desired product.

Workup

  1. additionwas added (14 μL, 0.15 mmol)
  2. customAfter 30 minutes the reaction was quenched
  3. additionby adding saturated NH4Cl (3 mL)
  4. extractionThe resulting mixture was extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by PTLC (SiO2)

Sources & evidence

ORD record
ord-b0167e9b8d71404b8c680b40fc9b32ce
Source dataset
uspto-grants-2014_01
Patent number
US08637555B2

Reaction notes

Loading…