Ethyl isothiocyanatoformate → HCID 24855568, compound

HRID 912714Notes

Reaction equation

HRID 912714 reaction equation
C(O[C:4]([N:6]=[C:7]=[S:8])=[O:5])C.[C:9]1([CH:15]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=2)[CH2:16][NH:17][C:18]2[N:19]=[CH:20][NH:21][C:22]=2C(N)=O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>ClCCl.CO>[C:9]1([CH:15]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=2)[CH2:16][N:17]2[C:18]3[N:19]=[CH:20][NH:21][C:22]=3[C:4](=[O:5])[NH:6][C:7]2=[S:8])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 85320Ethyl isothiocyanatoformateHCID 67414909HCID 67414909, compound

Product 1

HCID 24855568HCID 24855568, compoundYield 11.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

Ethoxycarbonyl isothiocyanate (0.12 mL, 0.99 mmol) was added to 4-[(2-phenyl-2-pyridin-2-ylethyl)amino]-1H-imidazole-5-carboxamide (0.28 g, 0.9 mmol, obtained from Example 23(a)) in dry dichloromethane (10 mL) and dry methanol (0.11 mL). The mixture was stirred for 5 h and then concentrated, redissolved in aqueous potassium hydroxide (1.2 N, 7 mL) and heated at 80° C. for 3 h. After cooling to r.t., pH was adjusted to 7 using hydrochloric acid (2 N). The mixture was filtered and the solid was purified using preparative HPLC, giving the title compound 36 mg (11% yield) as a solid.

Workup

  1. concentrationconcentrated
  2. dissolutionredissolved in aqueous potassium hydroxide (1.2 N, 7 mL)
  3. temperatureAfter cooling to r.t.
  4. filtrationThe mixture was filtered
  5. customthe solid was purified

Sources & evidence

ORD record
ord-108cdcf006b648349645352938a562a4
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Reaction notes

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