Dimethylamine, hydrochloride → HCID 16722303, compound

HRID 1983177Notes

Reaction equation

HRID 1983177 reaction equation
Cl[C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]1[O:17][C:16]([C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[CH:20][C:19]=2[O:30][CH3:31])=[N:15][N:14]=1.Cl.[CH3:33][NH:34][CH3:35].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O>[CH3:31][O:30][C:19]1[CH:20]=[C:21]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[CH:22]=[CH:23][C:18]=1[C:16]1[O:17][C:13]([C:3]2[C:4]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[N:5][O:6][C:2]=2[N:34]([CH3:35])[CH3:33])=[N:14][N:15]=1

Participants

6

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 16723117HCID 16723117, compound

Product 1

HCID 16722303HCID 16722303, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a suspension of 4-{4-[5-(5-chloro-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazol-2yl]-3-methoxy-phenyl}-morpholine (100 mg, 0.23 mmol) in DMSO (1 mL) was added dimethylamine hydrochloride (93 mg, 1.14 mmol) and potassium carbonate (158 mg, 1.14 mmol). The reaction mixture was stirred for 2 h at ambient temperature. It was diluted with water (5 mL) and the resulting suspension was stirred for 15 min at this temperature. Filtration and washing with water (5 mL) and tert-butylmethylether (5 mL) afforded the title compound (80 mg, 78%) which was obtained as an off-white solid. MS: m/e=448.2 [M+H]+.

Workup

  1. stirringthe resulting suspension was stirred for 15 min at this temperature
  2. filtrationFiltration
  3. washwashing with water (5 mL) and tert-butylmethylether (5 mL)

Sources & evidence

ORD record
ord-5daefebfb9bc4089b5ff471f816a8828
Source dataset
uspto-grants-2009_06
Patent number
US07541372B2

Reaction notes

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