Hydrochloric Acid → Methyl 5-(4-[2-(2,2,2-trifluoroethyl)guanidino]pyrimid-2-yloxy)valerimidate

HRID 2291325Notes

Reaction equation

HRID 2291325 reaction equation
[F:1][C:2]([F:22])([F:21])[CH2:3][N:4]=[C:5]([NH2:20])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]#[N:19])[N:8]=1.Cl.[CH3:24][OH:25]>C(Cl)(Cl)Cl>[F:22][C:2]([F:1])([F:21])[CH2:3][N:4]=[C:5]([NH2:20])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[NH:19])[O:25][CH3:24])[N:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 212797715-[4-(2-[2,2,2-Trifluoroethyl]guanidino)pyrimid-2-yloxy]valeronitrile

Product 1

HCID 21279807Methyl 5-(4-[2-(2,2,2-trifluoroethyl)guanidino]pyrimid-2-yloxy)valerimidate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The above nitrile (3 g.) was dissolved in dry chloroform (40 ml.) and MeOH (20 ml.), cooled to 0° and saturated with hydrogen chloride gas. The mixture was kept at 0° for 60 hours then volatile material was evaporated in vacuo. The residue was shaken with cold aqueous potassium carbonate solution (50 ml.) and extracted with chloroform (3×50 ml.). The combined extracts were dried (MgSO4) and evaporated in vacuo to give methyl 5-[4-(2-[2,2,2-trifluoroethyl]guanidino)pyrimid-2-yloxy]valerimidate as a gum which was used without further purification.

Workup

  1. customvolatile material was evaporated in vacuo
  2. extractionextracted with chloroform (3×50 ml.)
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-9ecd0941fe1f48719588c65f86ad1840
Source dataset
uspto-grants-1989_01
Patent number
US04795755

Reaction notes

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