Dimethylformamide → 4-[6-(2-[2,2,2-Trifluoroethyl]guanidino)pyrid-2-ylthio]butyric acid

HRID 978410Notes

Reaction equation

HRID 978410 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([S:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])[CH:5]=[CH:4][CH:3]=1.[F:15][C:16]([F:22])([F:21])[CH2:17][N:18]=[C:19]=S.C[N:24](C=O)C>>[F:15][C:16]([F:22])([F:21])[CH2:17][N:18]=[C:19]([NH2:24])[NH:1][C:2]1[N:7]=[C:6]([S:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 138837771,1,1-Trifluoro-2-isothiocyanatoethaneHCID 20202807HCID 20202807, compound

Product 1

HCID 202028384-[6-(2-[2,2,2-Trifluoroethyl]guanidino)pyrid-2-ylthio]butyric acid

Procedure

A mixture of 4-(6-aminopyrid-2-ylthio)butyric acid (0.21 g.) DMF (3 ml.) and 2,2,2-trifluoroethylisothiocyanate (0.15 g.) was left at room temperature for 18 hours and then evaporated to dryness. A solution of the residue in methanolic ammonia was treated with yellow mercuric oxide (0.43 g.) and the mixture stirred at room temperature for 1 hour. The mixture was filtered and the filtrate evaporated to dryness and the residue treated with 2N aqueous NaOH (5 ml.) and then filtered. The filtrate was acidified with HOAc and the precipitate collected to give 4-[6-(2-[2,2,2-trifluoroethyl]guanidino)pyrid-2-ylthio]butyric acid (0.17 g.) which was used without further purification.

Workup

  1. customevaporated to dryness
  2. additionA solution of the residue in methanolic ammonia was treated with yellow mercuric oxide (0.43 g.)
  3. filtrationThe mixture was filtered
  4. customthe filtrate evaporated to dryness
  5. additionthe residue treated with 2N aqueous NaOH (5 ml.)
  6. filtrationfiltered
  7. customthe precipitate collected

Sources & evidence

ORD record
ord-eef503f714f44aa48fdf737b7e5c439a
Source dataset
uspto-grants-1987_05
Patent number
US04665073

Reaction notes

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