Iodoacetamide → HCID 13883831, compound

HRID 543770Notes

Reaction equation

HRID 543770 reaction equation
C(O)(=O)/C=C\C(O)=O.[F:9][C:10]([F:28])([F:27])[CH2:11][N:12]=[C:13]([NH2:26])[NH:14][C:15]1[CH:20]=[CH:19][N:18]=[C:17]([S:21][CH2:22][CH2:23][CH2:24][SH:25])[N:16]=1.C[O-].[Na+].I[CH2:33][C:34]([NH2:36])=[O:35]>CO>[F:28][C:10]([F:9])([F:27])[CH2:11][N:12]=[C:13]([NH2:26])[NH:14][C:15]1[CH:20]=[CH:19][N:18]=[C:17]([S:21][CH2:22][CH2:23][CH2:24][S:25][CH2:33][C:34]([NH2:36])=[O:35])[N:16]=1

Participants

5

Reactant 3

HCID 3727IodoacetamideHCID 10942334Sodium MethoxideHCID 86739394HCID 86739394, compound

Product 1

HCID 13883831HCID 13883831, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-[4-(2-[2,2,2-trifluoroethyl]guanidino)pyrimid-2-ylthio]propanethiol hydrogen maleate (147 mg.) and sodium methoxide (70 mg.) in MeOH was treated with 2-iodoacetamide (123 mg.) and the solution stirred at room temperature for 24 hours and then evaporated to dryness. The residue was partitioned between water and EtOAc, and the EtOAc phase was dried and evaporated to dryness. The residue was purified by preparative tlc on silica gel using EtOAc/MeOH/concentrated aqueous ammonia (s.g. 0.880) 6:1:0.5 v/v/v as developing solvent to give 2-[3-(4-[2-(2,2,2-trifluoroethyl)guanidino]pyrimid-2-ylthio)propylthio]acetamide as a gum (50 mg.) which was crystallised as the hydrogen maleate salt (m.p. 168°-170°) from EtOAc.

Workup

  1. customevaporated to dryness
  2. customThe residue was partitioned between water and EtOAc
  3. dry with materialthe EtOAc phase was dried
  4. customevaporated to dryness
  5. customThe residue was purified by preparative tlc on silica gel

Sources & evidence

ORD record
ord-83c8e16fe39140a6a14e401a4f71072c
Source dataset
uspto-grants-1984_05
Patent number
US04447441

Reaction notes

Loading…