Boron trifluoride etherate → HCID 21919258, compound

HRID 1244379Notes

Reaction equation

HRID 1244379 reaction equation
I.CS[C:4]([C:6]1[S:7][C:8]2[C:14]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:13][CH:12]=[C:11]([O:21][CH3:22])[C:9]=2[N:10]=1)=[NH:5].[CH2:23]([N:30]1[CH2:35][CH2:34][C:33](OCC)(OCC)[CH:32]([NH2:42])[CH2:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.B(F)(F)F.CCOCC>O1CCCC1>[CH2:23]([N:30]1[CH2:35][CH2:34][C:33]2[N:5]=[C:4]([C:6]3[S:7][C:8]4[C:14]([N:15]5[CH2:20][CH2:19][O:18][CH2:17][CH2:16]5)=[CH:13][CH:12]=[C:11]([O:21][CH3:22])[C:9]=4[N:10]=3)[NH:42][C:32]=2[CH2:31]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 217299351-Benzyl-4,4-diethoxypiperidin-3-amineHCID 691840724-Methoxy-7-morpholin-4-yl-benzothiazole-2-carboximidothioic acid methyl ester hydroiodide

Product 1

HCID 21919258HCID 21919258, compoundYield 1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 0.04 g 4-methoxy-7-morpholin-4-yl-benzothiazole-2-carboximidothioic acid methyl ester hydroiodide in 1.8 ml tetrahydrofurane were added 0.1 g 1-benzyl-4,4-diethoxy-piperidin-3-ylamine in 1.8 ml tetrahydrofurane and the mixture was stirred at room temperature for 16 hours. Then 0.015 ml boron trifluoride etherate was added and the solvent was distilled off under vacuum. Again 0.015 ml boron trifluoride etherate was added and the mixture was dissolved in 1.5 ml dimethylformamide and heated for 15 minutes at 125° C. The solvent was distilled off and the residue was dissolved in dichloromethane and extracted with water. The organic layer was dried with sodium sulfate, filtered and the solvent was evaporated. Chromatography on silicagel with ethylacatate/heptane 1:1 to 2:1 yielded 0.4 mg (1%) 5-benzyl-2-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine as an amorphous solid; m/e=462 (M+H+).

Workup

  1. distillationthe solvent was distilled off under vacuum
  2. additionAgain 0.015 ml boron trifluoride etherate was added
  3. dissolutionthe mixture was dissolved in 1.5 ml dimethylformamide
  4. temperatureheated for 15 minutes at 125° C
  5. distillationThe solvent was distilled off
  6. dissolutionthe residue was dissolved in dichloromethane
  7. extractionextracted with water
  8. dry with materialThe organic layer was dried with sodium sulfate
  9. filtrationfiltered
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-11fac07d95c64a1cb1b38980ef5e47fc
Source dataset
uspto-grants-2006_10
Patent number
US07122545B2

Reaction notes

Loading…