Acetamidine monohydrochloride → HCID 178432569, compound

HRID 49378Notes

Reaction equation

HRID 49378 reaction equation
Cl.[C:2]([NH2:5])(=[NH:4])[CH3:3].[CH2:6]([O:13][C:14](=[O:29])[NH:15][CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25](=O)[CH2:26]Br)=[CH:21][CH:20]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[O-]CC.[Na+]>C(O)C>[CH2:6]([O:13][C:14](=[O:29])[NH:15][CH2:16][CH2:17][O:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]2[N:4]=[C:2]([CH3:3])[NH:5][CH:26]=2)=[CH:23][CH:24]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 67170Acetamidine monohydrochlorideHCID 2723922Sodium ethoxideHCID 12986050Benzyl-[2-(4-bromoacetylphenoxy)-ethyl]-carbamate

Product 1

HCID 178432569HCID 178432569, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Acetamidine hydrochloride (112 mg, 1.18 mmol), benzyl-[2-(4-bromoacetyl-phenoxy)-ethyl]-carbamate (160 mg, 0.39 mmol), and sodium ethoxide (80.3 mg, 1.18 mmol) were combined in a round-bottomed flask, dissolved in ethanol, and heated to about 80° C. for about two hours. The reaction mixture was then allowed to cool to room temperature, and the resulting heterogenous mixture was filtered. The filtrate was then concentrated in vacuo to an oil which was purified by column chromatography (silica gel; 5% methanol/methylene chloride to 10% methanol/methylene chloride) to afford 92 mg (64% yield) of the desired product. LRMS ([M+H]+)=352.2.

Workup

  1. temperatureto cool to room temperature
  2. filtrationthe resulting heterogenous mixture was filtered
  3. concentrationThe filtrate was then concentrated in vacuo to an oil which
  4. customwas purified by column chromatography (silica gel; 5% methanol/methylene chloride to 10% methanol/methylene chloride)

Sources & evidence

ORD record
ord-fe29b5ff1a114e16a240a8f32959a868
Source dataset
uspto-grants-2004_03
Patent number
US06706743B2

Reaction notes

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