Dimethylamine → HCID 22313995, compound

HRID 270463Notes

Reaction equation

HRID 270463 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH:13]=[CH:14][C:15]([O:17][CH2:18][C:19](=O)[CH3:20])=[CH:16][C:11]=3[S:10][N:9]=2)=[CH:4][CH:3]=1.[CH3:22][NH:23][CH3:24].[BH3-]C#N.[Na+].C([O-])(O)=O.[Na+]>C1COCC1.C(O)C.CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4].CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH:13]=[CH:14][C:15]([O:17][CH2:18][CH:19]([N:23]([CH3:24])[CH3:22])[CH3:20])=[CH:16][C:11]=3[S:10][N:9]=2)=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 674DimethylamineHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 22313976HCID 22313976, compound

Product 1

HCID 22313995HCID 22313995, compound

Reagents, catalysts & solvents 4

HCID 11026Titanium isopropoxideCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

74 mg (0.20 mmol) 1-[3-(4-Bromo-phenyl)-benzo[d]isothiazol-6-yloxy]-propan-2-one were treated with 133 μM 2M (0.17 mmol) dimethylamine in THF and 60 μM (0.20 mmol) tetraisopropyl orthotitanate. The solution was stirred at RT for 3.5 h. The mixture was diluted with 2 ml ethanol and 15 mg (0.2 mmol) NaCNBH3 were added, and stirring was continued over night. NaHCO3 and EtOAc were added, the inorganic phase extracted with EtOAc. The organic phases were washed with water and brine, dried over Na2SO4 and evaporated. Column chromatography with CH2Cl2:MeOH 9:1 gave {2-[3-(4-Bromo-phenyl)-benzo[d]isothiazol-6-yloxy]-1-methyl-ethyl}-dimethyl-amine as colorless oil, MS: 391 (MH+, 1Br).

Workup

  1. additionwere added
  2. stirringstirring
  3. waitwas continued over night
  4. extractionthe inorganic phase extracted with EtOAc
  5. washThe organic phases were washed with water and brine
  6. dry with materialdried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-4a8d1a2e06b7489eade04b522a4c2cf2
Source dataset
uspto-grants-2008_11
Patent number
US07449483B2

Reaction notes

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