Methyl isothiocyanate → HCID 178481693, compound

HRID 341201Notes

Reaction equation

HRID 341201 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)[NH2:2].[CH3:29][N:30]=[C:31]=[S:32]>CCO>[SH:32][C:31]1[N:30]([CH3:29])[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

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 59320927HCID 59320927, compound

Product 1

HCID 178481693HCID 178481693, compoundYield 31.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °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 (200 mg, 0.51 mmol) and methyl isothiocyanate (37 mg, 0.57 mmol) were dissolved in EtOH (6 ml) and heated at 70° C. overnight. The reaction mixture was allowed to cool, 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 (72 mg). MS: [M+H]+=448.

Workup

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

Sources & evidence

ORD record
ord-c46c2759241443a5b28b3bcaf494f179
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

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