1,4-Dioxane → HCID 136026810, compound

HRID 1718354Notes

Reaction equation

HRID 1718354 reaction equation
Cl.[C:2]([NH2:5])(=[NH:4])[CH3:3].C[O-].[Na+].[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH:24]([C:29](=O)[CH2:30][O:31][CH3:32])[C:25](OC)=[O:26])=[CH:19][CH:18]=1)#[N:10].O1CCOCC1>CO>[CH3:32][O:31][CH2:30][C:29]1[N:4]=[C:2]([CH3:3])[NH:5][C:25](=[O:26])[C:24]=1[CH2:23][C:20]1[CH:21]=[CH:22][C:17]([C:12]2[C:11]([C:9]#[N:10])=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 312751,4-DioxaneHCID 67170Acetamidine monohydrochlorideHCID 10942334Sodium MethoxideHCID 57460183HCID 57460183, compound

Product 1

HCID 136026810HCID 136026810, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of acetamidine hydrochloride (3.4 g) in methanol (30 mL) was added sodium methoxide (28% methanol solution, 10.3 g) at 0° C., a solution of methyl 2-[(2′-cyanobiphenyl-4-yl)methyl]-4-methoxy-3-oxobutanoate in methanol (60 mL)-1,4-dioxane (20 mL) was added, and the mixture was stirred at room temperature for 16 hr. The reaction mixture was concentrated, and water (50 mL) and 50% aqueous acetic acid solution were added to the residue and adjusted to pH 5. The obtained crystallized product was collected by filtration and washed with water to give the title compound as colorless crystals (5.27 g, 86%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater (50 mL) and 50% aqueous acetic acid solution were added to the residue
  3. customThe obtained crystallized product
  4. filtrationwas collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-dd633c26c4ab4a539f0ccee757121f15
Source dataset
uspto-grants-2010_09
Patent number
US07803940B2

Reaction notes

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