Boron trifluoride etherate → 2-(4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-3,4,6,7-tetrahydro-imidazo[4,5-c]pyridine-5-carboxylic acid tert-butyl ester

HRID 1244372Notes

Reaction equation

HRID 1244372 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].[C:23]([O:27][C:28]([N:30]1[CH2:35][CH2:34][C:33](OCC)(OCC)[CH:32]([NH2:42])[CH2:31]1)=[O:29])([CH3:26])([CH3:25])[CH3:24].B(F)(F)F.CCOCC>O1CCCC1>[C:23]([O:27][C:28]([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)=[O:29])([CH3:26])([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 53249937tert-Butyl 3-amino-4,4-diethoxypiperidine-1-carboxylateHCID 691840724-Methoxy-7-morpholin-4-yl-benzothiazole-2-carboximidothioic acid methyl ester hydroiodide

Product 1

HCID 111556662-(4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-3,4,6,7-tetrahydro-imidazo[4,5-c]pyridine-5-carboxylic acid tert-butyl esterYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 0.50 g 4-methoxy-7-morpholin-4-yl-benzothiazole-2-carboximidothioic acid methyl ester hydroiodide in 33 ml tetrahydrofurane was added 1.34 g 3-amino-4,4-diethoxy-piperidine-1-carboxylic acid tert-butyl ester and the mixture was stirred at room temperature for two days. Then 0.2 ml boron trifluoride etherate was added and the solvent was distilled off under vacuum. Again 0.2 ml boron trifluoride etherate was added and the mixture was dissolved in 30 ml dimethylformamide and heated for 10 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/hexane 1:1 followed by chromatography on aluminiumoxide with ethylacatate/hexane 1:1 yielded 0.18 g (35%) 2-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-3,4,6,7-tetrahydro-imidazo[4,5-c]pyridine-5-carboxylic acid tert-butyl ester as an amorphous solid; m/e=472 (M+H+).

Workup

  1. distillationthe solvent was distilled off under vacuum
  2. additionAgain 0.2 ml boron trifluoride etherate was added
  3. dissolutionthe mixture was dissolved in 30 ml dimethylformamide
  4. temperatureheated for 10 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-6d4b2724d2e14cc28e8d1f2dfbc1c04c
Source dataset
uspto-grants-2006_10
Patent number
US07122545B2

Reaction notes

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