1,8-Diazabicyclo(5.4.0)undec-7-ene → tert-Butyl {2-[(5-cyanopyridin-2-yl)thio]ethyl}carbamate

HRID 2389756Notes

Reaction equation

HRID 2389756 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][N:3]=1.[SH:10][CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17].N12CCCN=C1CCCCC2>CN(C=O)C.O>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([S:10][CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[N:3][CH:4]=1)#[N:9]

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 3017761N-(tert-butoxycarbonyl)-2-aminoethanethiolHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 59313027tert-Butyl {2-[(5-cyanopyridin-2-yl)thio]ethyl}carbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-Chloro-5-cyanopyridine (500 mg, 3.6 mmol), tert-butyl (2-mercaptoethyl)carbamate (426 mg, 2.4 mmol) and 1,8-diazabicyclo(5.4.0)undec-7-ene (549 mg, 3.6 mmol) are dissolved in DMF (5 ml) and stirred at RT under argon for 12 h. The reaction mixture is diluted with water (100 ml) and extracted with ethyl acetate (3×75 ml). The combined organic phases are washed with saturated aqueous sodium chloride solution, dried over magnesium sulphate and concentrated. After removal of the solvent, the residue is purified by preparative RP-HPLC (gradient of eluent: water/acetonitrile 90:10 to 10:90). 612 mg (91% of theory) of the product are obtained as a solid.

Workup

  1. extractionextracted with ethyl acetate (3×75 ml)
  2. washThe combined organic phases are washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated
  5. customAfter removal of the solvent
  6. customthe residue is purified by preparative RP-HPLC (gradient of eluent: water/acetonitrile 90:10 to 10:90)
  7. custom612 mg (91% of theory) of the product are obtained as a solid

Sources & evidence

ORD record
ord-d83be4cae71c4cd98ed06de31c4e6aaa
Source dataset
uspto-grants-2012_09
Patent number
US08273752B2

Reaction notes

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