Methanimidamide, hydrochloride (1:1) → HCID 135464158, compound

HRID 1673914Notes

Reaction equation

HRID 1673914 reaction equation
Cl.[CH:2]([NH2:4])=[NH:3].C[O-].[Na+].CO.[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH:25]([C:30](=O)[CH2:31][CH2:32][CH3:33])[C:26](OC)=[O:27])=[CH:20][CH:19]=1)#[N:11]>CO.O1CCOCC1>[O:27]=[C:26]1[NH:4][CH:2]=[N:3][C:30]([CH2:31][CH2:32][CH3:33])=[C:25]1[CH2:24][C:21]1[CH:20]=[CH:19][C:18]([C:13]2[C:12]([C:10]#[N:11])=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 10313058Methanimidamide, hydrochloride (1:1)HCID 23694274Sodium methanolate methanolHCID 57460349HCID 57460349, compound

Product 1

HCID 135464158HCID 135464158, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To an ice-cooled mixture of formamidine hydrochloride (3.73 g) and methanol (25 mL) was added dropwise 28% sodium methoxide-methanol solution (13.7 mL), and a mixture of methyl 2-[(2′-cyanobiphenyl-4-yl)methyl]-3-oxohexanoate (5.90 g), 1,4-dioxane (18 mL) and methanol (25 mL) was added dropwise. The mixture was stirred at room temperature for 12 hr. The solvent of the reaction mixture was evaporated under reduced pressure. The residue was diluted with ethyl acetate, and the diluted solution was washed with 0.1 M aqueous hydrochloric acid solution, water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give crude crystals. The crude crystals were washed with diisopropyl ether to give the title compound as a colorless solid (3.40 g, 61%).

Workup

  1. additionwas added dropwise
  2. customThe solvent of the reaction mixture was evaporated under reduced pressure
  3. additionThe residue was diluted with ethyl acetate
  4. washthe diluted solution was washed with 0.1 M aqueous hydrochloric acid solution, water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customto give crude crystals
  8. washThe crude crystals were washed with diisopropyl ether

Sources & evidence

ORD record
ord-8c4887c9a831443b9e12217a0525c4b8
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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