Aminoacetaldehyde dimethyl acetal → HCID 57344531, compound

HRID 2401385Notes

Reaction equation

HRID 2401385 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[C:25]([CH3:26])=[C:24]([CH3:27])[S:23][C:10]=3[C:11]3[C:21]([CH3:22])=[N:20][O:19][C:12]=3[C@H:13]([CH2:15][C:16](=S)[NH2:17])[N:14]=2)=[CH:4][CH:3]=1.CO[CH:30](OC)[CH2:31][NH2:32]>CC#N.Cl[Hg]Cl>[NH:32]1[CH:31]=[CH:30][N:17]=[C:16]1[CH2:15][C@H:13]1[C:12]2[O:19][N:20]=[C:21]([CH3:22])[C:11]=2[C:10]2[S:23][C:24]([CH3:27])=[C:25]([CH3:26])[C:9]=2[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[N:14]1

Participants

5

Reactant 2

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 86666723HCID 86666723, compound

Product 1

HCID 57344531HCID 57344531, compoundYield 6.2%

Reagents, catalysts & solvents 2

HCID 24085Mercuric ChlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-((6S)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-isoxazolo[5,4-c]thieno[2,3-e]azepin-6-yl)ethanethioamide (0.080 g, 0.19 mmol) and 2,2-dimethoxyethanamine (0.200 g, 1.90 mmol) in CH3CN (5 mL) was added HgCl2 (0.515 g, 1.90 mmol). The mixture was refluxed overnight. The reaction mixture was filtered, concentrated in vacuo and the residue was purified by column chromatography (silica-gel, petroleum:ethyl acetate=2:1) to give (6S)-6-((1H-imidazol-2-yl)methyl)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-isoxazolo[5,4-c]thieno[2,3-e]azepine as a yellow solid (0.005 g, 6.2% yield): 1H NMR (300 MHz, DMSO-d6) δ 8.26 (br, 1H), 7.42 (d, J=4.8 Hz, 2H), 7.24 (d, J=4.8 Hz, 2H), 6.82 (d, J=1.2 Hz, 2H), 4.40-4.30 (m, 1H), 3.84-3.74 (m, 2H), 2.50 (s, 3H), 2.42 (s, 3H), 1.64 (s, 3H); LC/MS m/z 423 [M+H]+.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated in vacuo
  4. customthe residue was purified by column chromatography (silica-gel, petroleum:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-ac88aae5835941e59384b158423c3fa2
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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