5-(tert-Butoxycarbonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylic acid → HCID 18377301, compound

HRID 2301118Notes

Reaction equation

HRID 2301118 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[S:14][C:15]([C:17]([OH:19])=O)=[CH:16][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O1CCCC1.[CH3:25][NH:26][CH3:27]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[S:14][C:15]([C:17](=[O:19])[N:26]([CH3:27])[CH3:25])=[CH:16][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 177503995-(tert-Butoxycarbonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylic acidHCID 22320367Dimethylamine tetrahydrofuran

Product 1

HCID 18377301HCID 18377301, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-t-Butoxycarbonyl-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine-2-carboxylic acid (570 mg, 2.0 mmol) was dissolved in anhydrous tetrahydrofuran (10 ml), and the solution was mixed with 1,1-carbonyldiimidazole (320 mg, 2.0 mmol) and stirred at room temperature for 1 hour. The reaction solution was mixed with dimethylamine tetrahydrofuran solution (2.0 M, 4.0 ml, 2.0 mmol) and the stirring was continued for 15 hours. The solvent was removed by evaporation from the reaction solution under a reduced pressure, and the residue was mixed with ethyl acetate and washed with water, hydrochloric acid (1 N), sodium hydroxide aqueous solution (1 N) and saturated brine. The organic layer was dried with anhydrous sodium sulfate, and the solvent was removed by evaporation under a reduced pressure to obtain 470 mg (1.5 mmol, 77% in yield) of the title compound.

Workup

  1. waitthe stirring was continued for 15 hours
  2. customThe solvent was removed by evaporation from the reaction solution under a reduced pressure
  3. additionthe residue was mixed with ethyl acetate
  4. washwashed with water, hydrochloric acid (1 N), sodium hydroxide aqueous solution (1 N) and saturated brine
  5. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  6. customthe solvent was removed by evaporation under a reduced pressure
  7. customto obtain

Sources & evidence

ORD record
ord-a64fdd2e028b4dbb9e84484e848fac3e
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

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