Guanidine Hydrochloride → HCID 178494668, compound

HRID 2117756Notes

Reaction equation

HRID 2117756 reaction equation
CN(C)[CH:3]=[CH:4][C:5]([C:7]1[NH:11][C:10]([CH2:12][O:13][CH3:14])=[N:9][C:8]=1[C:15]([O:18][CH3:19])([CH3:17])[CH3:16])=O.Cl.[NH2:22][C:23]([NH2:25])=[NH:24].C[O-].[Na+]>C(O)CCC>[NH2:24][C:23]1[N:25]=[C:5]([C:7]2[NH:11][C:10]([CH2:12][O:13][CH3:14])=[N:9][C:8]=2[C:15]([O:18][CH3:19])([CH3:17])[CH3:16])[CH:4]=[CH:3][N:22]=1

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 10942334Sodium MethoxideHCID 178494669HCID 178494669, compound

Product 1

HCID 178494668HCID 178494668, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

5-(3-Dimethylaminoprop-2-en-1-oyl)-1-methoxyisopropyl-2-methoxymethylimidazole (Method 56; 3.13, 11.1 mmol) and guanidine hydrochloride (2.65 g, 27.8 mmol) were suspended in 1-butanol (20 ml). Sodium methoxide (2.4 g, 44 mmol) was added in one portion and the mixture heated under reflux, under an atmosphere of nitrogen, for 18 hours. The volatiles were removed by evaporation. Water (50 ml) was added and extracted EtOAc (3×50 ml). The organic layers were combined and dried with Chemelut CE1010 and the solvent evaporated in vacuo. The residue was purified by flash silica chromatography eluting with DCM:MeOH (100:0 increasing in polarity to 95:5) to give the title compound as an orange solid (1.86 g, 60%). NMR: 1.43 (d, 3H), 3.16 (s, 3H), 3.24 (s, 3H), 3.63 (m, 1H), 3.89 (m, 1H), 4.50 (q, 2H), 5.26 (m, 1H), 6.57 (s, 2H), 6.80 (d, 1H), 7.40 (s, 1H), 8.21 (d, 1H); m/z 278.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux, under an atmosphere of nitrogen, for 18 hours
  3. customThe volatiles were removed by evaporation
  4. additionWater (50 ml) was added
  5. extractionextracted EtOAc (3×50 ml)
  6. dry with materialdried with Chemelut CE1010
  7. customthe solvent evaporated in vacuo
  8. customThe residue was purified by flash silica chromatography
  9. washeluting with DCM:MeOH (100:0 increasing in polarity to 95:5)

Sources & evidence

ORD record
ord-9b93e17b15db496cb04b2e827237c41c
Source dataset
uspto-grants-2008_10
Patent number
US07442697B2

Reaction notes

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