Ethanol → HCID 11594627, compound

HRID 536083Notes

Reaction equation

HRID 536083 reaction equation
C(OC([N:6]=[C:7]=[S:8])=O)C.C(O[C:12]([C:14]1[NH:15][CH:16]=[CH:17][C:18]=1[NH:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:28][CH3:29])[N:22]=1)=[O:13])C.CC[O-].[Na+].C(O)C>C(Cl)Cl>[CH2:28]([O:27][C:23]1[N:22]=[C:21]([CH2:20][N:19]2[C:18]3[CH:17]=[CH:16][NH:15][C:14]=3[C:12](=[O:13])[NH:6][C:7]2=[S:8])[CH:26]=[CH:25][CH:24]=1)[CH3:29]

Participants

6

Reactant 4

HCID 702EthanolHCID 85320Ethyl isothiocyanatoformateHCID 2723922Sodium ethoxide2×HCID 67068467HCID 67068467, compound

Product 1

HCID 11594627HCID 11594627, compoundYield 15.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethoxycarbonyl isothiocyanate (0.12 g, 0.90 mmol) was added to 3-[(6-ethoxy-pyridin-2-ylmethyl)-amino]-1H-pyrrole-2-carboxylic acid ethyl ester (0.24 g, 0.82 mmol) in CH2Cl2 (5 mL) and the solution was stirred at ambient temperature for 35 minutes. The solvent was evaporated and 0.4M NaOEt in ethanol (3 mL, 1.2 mmol) was added to the residue and the mixture was refluxed for 1 h. More NaOEt (0.4M in ethanol, 1.5 mL, 0.6 mmol) was added and the solution was refluxed for another 1.5 h. The solvent was evaporated, the residue was dissolved in water and the pH adjusted to neutral pH with 1M HCl. The resulting solid was collected, washed, and dried to give crude product. This material was purified by preparative HPLC to yield the title compound (38 mg, 15%) as a solid.

Workup

  1. customThe solvent was evaporated
  2. temperaturethe mixture was refluxed for 1 h
  3. temperaturethe solution was refluxed for another 1.5 h
  4. customThe solvent was evaporated
  5. dissolutionthe residue was dissolved in water
  6. customThe resulting solid was collected
  7. washwashed
  8. customdried
  9. customto give crude product
  10. customThis material was purified by preparative HPLC

Sources & evidence

ORD record
ord-312a073801954911b89b8e8f0e71c7de
Source dataset
uspto-grants-2014_10
Patent number
US08859568B2

Reaction notes

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