Thionyl Chloride → HCID 16069053, compound

HRID 2059813Notes

Reaction equation

HRID 2059813 reaction equation
[CH:1]([N:4]([CH:25]([CH3:27])[CH3:26])[C:5](=[O:24])[CH:6]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:8][C:9]([NH2:11])=O)([CH3:3])[CH3:2].O=S(Cl)Cl>CN(C=O)C>[C:9]([CH2:8][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:6]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[C:5]([N:4]([CH:25]([CH3:27])[CH3:26])[CH:1]([CH3:3])[CH3:2])=[O:24])#[N:11]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 57692750HCID 57692750, compound

Product 1

HCID 16069053HCID 16069053, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N1,N1-diisopropyl-3-phenyl-2-pyridin-3-ylpentanediamide (90 mg, 0.245 mmol) in 1 mL DMF was added SOCl2 (0.5 mL) and heated at 90 C for 45 min. Concentrated (azeotroped 2× from benzene) and purified by r.p. HPLC. Desired fractions from HPLC were combined and the product was isolated as free base. White solid, single diastereomer.

Workup

  1. temperatureheated at 90 C for 45 min
  2. concentrationConcentrated
  3. custom(azeotroped 2× from benzene)
  4. custompurified by r.p
  5. customthe product was isolated as free base

Sources & evidence

ORD record
ord-4b295cbafecc4ab9ae880cfdcdb9ad47
Source dataset
uspto-grants-2012_10
Patent number
US08278317B2

Reaction notes

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