Carbon Disulfide → HCID 59320941, compound

HRID 341216Notes

Reaction equation

HRID 341216 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)=[S:32]>CCO>[S:32]=[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][NH:2]1

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 59320927HCID 59320927, compound

Product 1

HCID 59320941HCID 59320941, compoundYield 52.9%

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, cooled and then placed in an ice bath upon which a precipitate was formed. The solid was filtered off, wash with EtOAc and Et2O, then dried to afford the title compound (69 mg). MS: [M+H]+=435.

Workup

  1. temperaturecooled
  2. customplaced in an ice bath upon which
  3. customa precipitate was formed
  4. filtrationThe solid was filtered off
  5. washwash with EtOAc and Et2O
  6. customdried

Sources & evidence

ORD record
ord-0943051215644c4593deb0c22f05b841
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

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