Tetrahydrofuran → HCID 178482551, compound

HRID 493709Notes

Reaction equation

HRID 493709 reaction equation
[CH3:1][N:2]1[C:6]([CH2:7][N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[CH:5][S:4]/[C:3]/1=[N:21]\[CH3:22].C([Li])CCC.CCCCCC.[Cl-].[NH4+].C1C[O:39][CH2:38]C1>CN(C=O)C>[CH:38]([C:5]1[S:4]/[C:3](=[N:21]\[CH3:22])/[N:2]([CH3:1])[C:6]=1[CH2:7][N:8]1[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH2:12][CH2:13]1)=[O:39]

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 8058HexaneHCID 25517Ammonium ChlorideHCID 178418339ButyllithiumHCID 178482546HCID 178482546, compound

Product 1

HCID 178482551HCID 178482551, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyl 4-(((2Z)-3-methyl-2-methylimino-2,3-dihydro-1,3-thiazol-4-yl)methyl)piperazine-1-carboxylate (1.0 g) obtained in Example 11a) was dissolved in THF (20 mL), n-butyllithium (4.6 mL; a 1.6 M hexane solution) was added thereto at −70° C., and the mixture was mixed for 30 minutes. To the reaction solution was added DMF (1.0 mL), mixed at −70° C. for 1 hour, and then an aqueous ammonium chloride solution was added thereto at 0° C. The mixture was extracted with ethyl acetate, and the extract was dried over anhydrous magnesium sulfate. The solvent was distilled off to give the title compound (1.1 g) as a pale brown oily matter.

Workup

  1. additionat −70° C., and the mixture was mixed for 30 minutes
  2. additionmixed at −70° C. for 1 hour
  3. customat 0° C
  4. extractionThe mixture was extracted with ethyl acetate
  5. dry with materialthe extract was dried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-0f568a2f55794714bf1adc51b66a8301
Source dataset
uspto-grants-2009_05
Patent number
US07534887B2

Reaction notes

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