Methyl iodide → HCID 59321125, compound

HRID 341217Notes

Reaction equation

HRID 341217 reaction equation
[NH:1]([C:3]([C:5]1[CH:10]=[CH:9][N:8]2[C:11]([C:14]3[CH:15]=[C:16]([NH:20][C:21]([NH:23][CH2:24][C:25]([F:28])([F:27])[F:26])=[O:22])[CH:17]=[CH:18][CH:19]=3)=[CH:12][N:13]=[C:7]2[CH:6]=1)=[O:4])[NH2:2].[OH-].[K+].[C:31](=[S:33])=S.[CH3:34]I>CCO>[CH3:34][S:33][C:31]1[O:4][C:3]([C:5]2[CH:10]=[CH:9][N:8]3[C:11]([C:14]4[CH:15]=[C:16]([NH:20][C:21]([NH:23][CH2:24][C:25]([F:28])([F:27])[F:26])=[O:22])[CH:17]=[CH:18][CH:19]=4)=[CH:12][N:13]=[C:7]3[CH:6]=2)=[N:1][N:2]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 59320927HCID 59320927, compound

Product 1

HCID 59321125HCID 59321125, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 1-[3-(7-Hydrazinocarbonyl-imidazo[1,2-a]pyridin-3-yl)-phenyl]-3-(2,2,2-trifluoro-ethyl)-urea (120 mg, 0.30 mmol) and KOH (20 mg, 0.36 mmol) in EtOH (4 ml) was added carbon disulfide (241, 0.36 mmol). The reaction mixture was heated at 65° C. for 3 h. Methyl iodide (200, excess) was added and the reaction mixture heated at 65° C. for 1 h. The mixture was then cooled, placed in an ice bath upon which a precipitate was formed. The solid was filtered off, washed with EtOAc and Et2O, then dried to afford the title compound (89 mg). MS: [M+H]+=449.

Workup

  1. temperaturethe reaction mixture heated at 65° C. for 1 h
  2. temperatureThe mixture was then cooled
  3. customplaced in an ice bath upon which
  4. customa precipitate was formed
  5. filtrationThe solid was filtered off
  6. washwashed with EtOAc and Et2O
  7. customdried

Sources & evidence

ORD record
ord-3bf921fc6b394a9c8e5b1345c8344ed9
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

Loading…