Ammonia → 4-[6-(2-[2,2,2-Trifluoroethyl]guanidino)pyrid-2-ylthio]butyramide

HRID 543790Notes

Reaction equation

HRID 543790 reaction equation
[F:1][C:2]([F:22])([F:21])[CH2:3][N:4]=[C:5]([NH2:20])[NH:6][C:7]1[N:12]=[C:11]([S:13][CH2:14][CH2:15][CH2:16][C:17](O)=[O:18])[CH:10]=[CH:9][CH:8]=1.C([N:25](CC)CC)C.C(OC(Cl)=O)C(C)C.N>CN(C=O)C.CCO>[F:1][C:2]([F:22])([F:21])[CH2:3][N:4]=[C:5]([NH2:20])[NH:6][C:7]1[N:12]=[C:11]([S:13][CH2:14][CH2:15][CH2:16][C:17]([NH2:25])=[O:18])[CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 202028384-[6-(2-[2,2,2-Trifluoroethyl]guanidino)pyrid-2-ylthio]butyric acid

Product 1

HCID 138838044-[6-(2-[2,2,2-Trifluoroethyl]guanidino)pyrid-2-ylthio]butyramide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-[6-(2-[2,2,2-trifluoroethyl]guanidino)pyrid-2-ylthio]butyric acid (84 mg.) and triethylamine (0.2 ml.) in DMF (5 ml.) was stirred at 0° while isobutylchloroformate (68 mg.) was added. The solution was kept at 0° for 0.5 hours, treated with a saturated solution of ammonia in EtOH (1 ml.) and then stirred at room temperature for 18 hours. The solution was evaporated to dryness and the residue partitioned between N aqueous HCl and EtOAc. The aqueous phase was basified with 10 N aqueous NaOH and extracted with EtOAc, and the extract was dried and evaporated to dryness to give 4-[6-(2-[2,2,2-trifluoroethyl]guanidino)pyrid-2-ylthio]butyramide (60 mg.) which was crystallised as the hydrogen maleate salt from acetone, m.p. 138°-141°.

Workup

  1. additionwas added
  2. customThe solution was evaporated to dryness
  3. customthe residue partitioned between N aqueous HCl and EtOAc
  4. extractionextracted with EtOAc
  5. customthe extract was dried
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-4bad583de3054ede90db2712ee5f9399
Source dataset
uspto-grants-1984_05
Patent number
US04447441

Reaction notes

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