Methylamine → N-methyl-5-[2-(2-[2,2,2-trifluoroethyl]guanidino)thiazol-4-yl]valeramide

HRID 543780Notes

Reaction equation

HRID 543780 reaction equation
[F:1][C:2]([F:22])([F:21])[CH2:3][N:4]=[C:5]([NH2:20])[NH:6][C:7]1[S:8][CH:9]=[C:10]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18]C)=O)[N:11]=1.[CH3:23][NH2:24]>>[CH3:23][NH:24][C:16](=[O:18])[CH2:15][CH2:14][CH2:13][CH2:12][C:10]1[N:11]=[C:7]([NH:6][C:5]([NH2:20])=[N:4][CH2:3][C:2]([F:1])([F:22])[F:21])[S:8][CH:9]=1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 20202828HCID 20202828, compound

Product 1

HCID 20202817N-methyl-5-[2-(2-[2,2,2-trifluoroethyl]guanidino)thiazol-4-yl]valeramideYield 85%

Procedure

A mixture of methyl 5-[2-(2-[2,2,2-trifluoroethyl]guanidino)thiazol-4-yl]valerate (0.4 g.) and ethanolic methylamine (33% w/v, 60 ml.) was allowed to stand at room temperature for 2 days. The mixture was then evaporated to dryness and the residue recrystallised from EtOAc/ether to give N-methyl-5-[2-(2-[2,2,2-trifluoroethyl]guanidino)thiazol-4-yl]valeramide (yield 85%), m.p. 122°-126°.

Workup

  1. customThe mixture was then evaporated to dryness
  2. customthe residue recrystallised from EtOAc/ether

Sources & evidence

ORD record
ord-47590d2358444724ab9cc73c5b4eaddf
Source dataset
uspto-grants-1984_05
Patent number
US04447441

Reaction notes

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