Methanol → HCID 24855569, compound

HRID 912716Notes

Reaction equation

HRID 912716 reaction equation
C(O[C:4]([N:6]=[C:7]=[S:8])=[O:5])C.[N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([CH2:19][NH:20][C:21]2(C(N)=O)[CH2:25][NH:24][CH:23]=[N:22]2)=[CH:11][CH:10]=1.CO>ClCCl>[N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([CH2:19][N:20]2[C:21]3[N:22]=[CH:23][NH:24][C:25]=3[C:4](=[O:5])[NH:6][C:7]2=[S:8])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 85320Ethyl isothiocyanatoformateHCID 178513791HCID 178513791, compound

Product 1

HCID 24855569HCID 24855569, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethoxycarbonyl isothiocyanate (0.5 ml, 4.18 mmol) was added to a solution of 4-[(quinolin-4-ylmethyl)amino]-1H-imidazole-4-carboxamide (0.93 g, crude material from Example 24(a)) dissolved in anhydrous dichloromethane (10 mL) and methanol (5 mL) mixture. After o.n. (over night) at r.t., the solution was concentrated in vacuo and the residue was dissolved in 1N NaOH solution (30 mL) and refluxed for 3.5 h. After cooling to r.t., the pH was adjusted to ˜6.5 with 2 N HCl. The solid that formed was collected by filtration and dried generating 0.35 g of crude material. A portion of the solid (150 mg) was purified by preparative HPLC, and the solid obtained was washed with dichloromethane and ether, generating 25.9 mg (9% yield over two steps) of the title compound.

Workup

  1. concentration(over night) at r.t., the solution was concentrated in vacuo
  2. dissolutionthe residue was dissolved in 1N NaOH solution (30 mL)
  3. temperaturerefluxed for 3.5 h
  4. customThe solid that formed
  5. filtrationwas collected by filtration
  6. customdried
  7. customA portion of the solid (150 mg) was purified by preparative HPLC
  8. customthe solid obtained
  9. washwas washed with dichloromethane and ether

Sources & evidence

ORD record
ord-82918e7a3dd943e09d673d0dac75d14e
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Reaction notes

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