Pyridine → HCID 131730929, compound

HRID 2035295Notes

Reaction equation

HRID 2035295 reaction equation
O[C:2]([CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]1[C@@H:16]2[C@@H:11]([NH:12][C:13]([NH:15]2)=[O:14])[CH2:10][S:9]1)=[O:3].[NH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.[N:23]1C=CC=CC=1>S(Cl)(Cl)=O>[N:17]1([C@@:16]23[C@H:8]([CH2:7][CH2:6][CH2:5][CH2:4][C:2]([NH2:23])=[O:3])[S:9][CH2:10][C@@H:11]2[NH:12][C:13](=[O:14])[NH:15]3)[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 4837PiperazineHCID 171548Biotin

Product 1

HCID 131730929HCID 131730929, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent2×

Procedure

Biotin (0.34 g, 1.4 mmols) was dissolved in 8 mL of neat thionyl chloride. This reaction was allowed to proceed for 5 min before the reaction was placed under vacuum where excess thionyl chloride was removed. The resulting oil was resuspended in 10 mL of CH2Cl2 and dried down. This process was repeated three times in order to drive off excess thionyl chloride. A solution of piperazine (0.54 g, 6.3 mmols) dissolved in 30 mL of pyridine was added to the resulting oil. This solution was stirred overnight, concentrated and the resulting solid was triturated with 40 mL of MeOH. The MeOH soluble material was collected by filtration, concentrated, and triturated with 40 ml of CH2Cl2. The CH2Cl2 soluble material was collected by filtration, concentrated and chromatographed on a 1 cm silica column with 2:98 NH4OH:ethanol as the running solvent. Elution was monitored by TLC where the product displays an Rf of 0.80 with a 33:67 NH4OH:EtOH developing solution. The appropriate fractions were concentrated to give 42.9 mg of the piperazine biotinamide as a white solid in a 10% yield.

Workup

  1. customwas removed
  2. customdried down
  3. additionwas added to the resulting oil
  4. concentrationconcentrated
  5. customthe resulting solid was triturated with 40 mL of MeOH
  6. filtrationThe MeOH soluble material was collected by filtration
  7. concentrationconcentrated
  8. customtriturated with 40 ml of CH2Cl2
  9. filtrationThe CH2Cl2 soluble material was collected by filtration
  10. concentrationconcentrated
  11. customchromatographed on a 1 cm silica column with 2:98 NH4OH
  12. washElution
  13. concentrationThe appropriate fractions were concentrated

Sources & evidence

ORD record
ord-12a6ba47f0fb4e34b5aa8bf0f6bf5365
Source dataset
uspto-grants-2013_11
Patent number
US08574546B2

Reaction notes

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