Pyridine → HCID 67246058, compound

HRID 2425056Notes

Reaction equation

HRID 2425056 reaction equation
[O-]C#[N:3].[Na+].N1C=CC=CC=1.[CH3:11][C:12]1[CH:13]=[C:14]([S:18](Cl)(=[O:20])=[O:19])[CH:15]=[CH:16][CH:17]=1.C([O:26][C:27]([NH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][NH2:36])=O)(C)(C)C>C(#N)C>[NH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][NH:29][C:27]([NH:3][S:18]([C:14]1[CH:15]=[CH:16][CH:17]=[C:12]([CH3:11])[CH:13]=1)(=[O:20])=[O:19])=[O:26]

Participants

6

Reactant 4

HCID 1049PyridineHCID 517096Sodium CyanateHCID 2733170N-BOC-1,6-diaminohexaneHCID 27345953-Methylbenzenesulphonyl chloride

Product 1

HCID 67246058HCID 67246058, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a suspension of 0.47 sodium cyanate in 20 ml acetonitrile was added 0.42 g pyridine and 0.95 g m-methylphenylsulfonylchloride and the mixture was agitated in an ultrasound bath under argon for ca 1 h. The resulting suspension was added to a solution of 0.500 g N-mono-tert.butyloxycarbonylhexamethylenediamine in 10 ml acetonitrile and the mixture was stirred at room temperature for 2 h. The solvent was evaporated and the residue was partitioned between dichlormethane and 1N sodium hydroxide. The phases were separated and the aqueous phase was acidified by addition of citric acid and extracted with dichloromethane. The second organic phase was washed with half concentrated brine and purified by chromatography on silica gel with heptane:ethyl acetate=1:1. The product fractions were collected and evaporated. The residue was taken up in 5 ml trifluoro acetic acid and kept at room temperature for 4 h. The solvent was evaporated and the residue was taken up in methanol and purified by chromatography on silica gel with a gradient of dichloromethane:methanol:ammonia=19:1:0.1 to 7:3:0.2. The product fractions were concentrated under aspirator vacuum whereby crystallisation occurred. The product was recrystallized from methanol to yield 0.180 g of the title compound as white crystals melting at 186.7-187.4° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 h
  2. customThe solvent was evaporated
  3. customthe residue was partitioned between dichlormethane and 1N sodium hydroxide
  4. customThe phases were separated
  5. additionthe aqueous phase was acidified by addition of citric acid
  6. extractionextracted with dichloromethane
  7. washThe second organic phase was washed with half concentrated brine
  8. custompurified by chromatography on silica gel with heptane
  9. customThe product fractions were collected
  10. customevaporated
  11. customThe solvent was evaporated
  12. custompurified by chromatography on silica gel with a gradient of dichloromethane
  13. concentrationThe product fractions were concentrated under aspirator vacuum whereby crystallisation
  14. customThe product was recrystallized from methanol

Sources & evidence

ORD record
ord-07d96e79ac8748e5a48ce475d50ddedd
Source dataset
uspto-grants-2011_06
Patent number
US07964633B2

Reaction notes

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