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

HRID 2171495Notes

Reaction equation

HRID 2171495 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-49a670d241704327aeffff80001168eb
Source dataset
uspto-grants-2015_06
Patent number
US09051323B2

Reaction notes

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