Methanol → HCID 24855565, compound

HRID 912711Notes

Reaction equation

HRID 912711 reaction equation
C(O[C:4]([N:6]=[C:7]=[S:8])=[O:5])C.[N:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][O:16][CH:17]([CH3:28])[CH2:18][NH:19][C:20]1[N:21]=[CH:22][NH:23][C:24]=1C(N)=O.CO>ClCCl>[N:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][O:16][CH:17]([CH3:28])[CH2:18][N:19]1[C:20]2[N:21]=[CH:22][NH:23][C:24]=2[C:4](=[O:5])[NH:6][C:7]1=[S:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 85320Ethyl isothiocyanatoformate2×HCID 67416134HCID 67416134, compound

Product 1

HCID 24855565HCID 24855565, compoundYield 9.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

Ethoxycarbonyl isothiocyanate (0.246 mL, 2.18 mmol) was added to a suspension of 4-{[2-(pyridin-2-ylmethoxy)propyl]amino}-1H-imidazole-5-carboxamide (0.500 g, 1.82 mmol, obtained from Example 20(c)) in dichloromethane (10 mL). After 0.5 h, methanol (2 mL) was added. The solvent was removed in vacuo and acetone (5 mL) and another portion of ethoxycarbonyl isothiocyanate (0.246 mL, 2.18 mmol) were added. After o.n. stirring, the reaction was concentrated in vacuo. To the residue was added 1 N NaOH (10 mL) and the resulting solution was heated for 4 h at 100° C. After cooling to r.t., 2 N HCl was added until pH˜6. The mixture was concentrated in vacuo. The product was purified by preparative HPLC resulting in 54.3 mg (9% yield) of the title compound.

Workup

  1. customThe solvent was removed in vacuo and acetone (5 mL)
  2. concentrationthe reaction was concentrated in vacuo
  3. additionTo the residue was added 1 N NaOH (10 mL)
  4. temperatureAfter cooling to r.t.
  5. addition2 N HCl was added until pH˜6
  6. concentrationThe mixture was concentrated in vacuo
  7. customThe product was purified by preparative HPLC

Sources & evidence

ORD record
ord-0daf6077ae1f462a8aeade7331dbde54
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Reaction notes

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