Acetamidine monohydrochloride → HCID 136348387, compound

HRID 869595Notes

Reaction equation

HRID 869595 reaction equation
[C:1](/[C:3](=[C:5]1/[C:6]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:7]=2[O:8][CH2:9][C:10]2[CH:15]=[C:14]([CH2:16][CH:17]([C:23](=O)[CH2:24][CH2:25][CH3:26])[C:18]([O:20]CC)=O)[CH:13]=[CH:12][C:11]/1=2)/[CH3:4])#[N:2].Cl.[C:34](=[NH:37])([NH2:36])[CH3:35].CO.C[O-].[Na+]>CO>[F:32][C:29]1[CH:30]=[CH:31][C:6]2=[C:7]([CH:28]=1)[O:8][CH2:9][C:10]1[CH:15]=[C:14]([CH2:16][C:17]3[C:18](=[O:20])[NH:37][C:34]([CH3:35])=[N:36][C:23]=3[CH2:24][CH2:25][CH3:26])[CH:13]=[CH:12][C:11]=1/[C:5]/2=[C:3](/[CH3:4])\[C:1]#[N:2]

Participants

5

Reactant 3

HCID 67170Acetamidine monohydrochlorideHCID 23694274Sodium methanolate methanolHCID 86721445HCID 86721445, compound

Product 1

HCID 136348387HCID 136348387, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[step 2] (E)-ethyl 2-{[11-(1-cyanoethylidene)-3-fluoro-6,11-dihydrodibenzo[b,e]oxepin-8-yl]methyl}-3-oxohexanoate (1.18 g, 2.71 mmol) obtained in step 1 was dissolved in methanol (14 mL), acetimidamide hydrochloride (640 mg, 6.77 mmol) and 28% sodium methoxide methanol solution (1.83 mL, 9.48 mmol) were added, and the mixture was stirred at room temperature for 2 hr. The mixture was concentrated under reduced pressure, methanol was added to the obtained residue, and the precipitated crystals were collected by suction filtration to give (E)-2-{3-fluoro-8-[(2-methyl-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl)methyl]dibenzo[b,e]oxepin-11(6H)-ylidene}propanenitrile (960 mg, 82%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure, methanol
  2. additionwas added to the obtained residue
  3. filtrationthe precipitated crystals were collected by suction filtration

Sources & evidence

ORD record
ord-0b6f8fc3b4784b5cb5e338ba0a6ad1c0
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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