Guanidine Hydrochloride → HCID 178478827, compound

HRID 1699390Notes

Reaction equation

HRID 1699390 reaction equation
C([O:3][C:4]([C:6]1[C:16]2[O:15][CH2:14][CH2:13][C:12]([C:17]([O:19]CC)=O)=[CH:11][C:10]=2[CH:9]=[CH:8][CH:7]=1)=O)C.[ClH:22].[NH2:23][C:24]([NH2:26])=[NH:25].C[O-].[Na+]>CN(C)C=O.CO>[ClH:22].[ClH:22].[NH:25]([C:4]([C:6]1[C:16]2[O:15][CH2:14][CH2:13][C:12]([C:17]([NH:25][C:24]([NH2:26])=[NH:23])=[O:19])=[CH:11][C:10]=2[CH:9]=[CH:8][CH:7]=1)=[O:3])[C:24]([NH2:26])=[NH:23]

Participants

6

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 10942334Sodium MethoxideHCID 18319635HCID 18319635, compound

Product 1

HCID 178478827HCID 178478827, compoundYield 34.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of ethyl 2,3-dihydro-9-ethoxycarbonyl-1-benzoxepin-4-carboxylate (0.10 g) and guanidine hydrochloride (0.33 g) in N,N-dimethylformamide (2 ml) was added 28% sodium methoxide in methanol (0.66 ml) at room temperature. After the mixture was stirred at room temperature overnight, it was purified by column chromatography on silica gel using a mixture of chloroform and methanol (30:1 to 4:1). The fractions containing objective compound was collected and evaporated in vacuo. The residue was treated with methanol and 4N hydrogen chloride in 1,4-dioxane, and the solvent was evaporated in vacuo. The residue was triturated with ethanol to give (2,3-dihydro-9-guanidinocarbonyl-1-benzoxepin-4-carbonyl)guanidine dihydrochloride (46 mg).

Workup

  1. customit was purified by column chromatography on silica gel using
  2. additiona mixture of chloroform and methanol (30:1 to 4:1)
  3. additionThe fractions containing objective compound
  4. customwas collected
  5. customevaporated in vacuo
  6. additionThe residue was treated with methanol and 4N hydrogen chloride in 1,4-dioxane
  7. customthe solvent was evaporated in vacuo
  8. customThe residue was triturated with ethanol

Sources & evidence

ORD record
ord-312653dee409460bb7bf4445006ca242
Source dataset
uspto-grants-2002_02
Patent number
US06346527B1

Reaction notes

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