Acetic Acid → HCID 178453912, compound

HRID 2042404Notes

Reaction equation

HRID 2042404 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][CH:15]=O)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[N:18]1([C:24]2[C:29]3[CH:30]=[CH:31][S:32][C:28]=3[CH:27]=[CH:26][N:25]=2)[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.CC(O)=O.C([O-])(O)=O.[Na+]>ClCCCl>[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][CH2:15][N:21]2[CH2:22][CH2:23][N:18]([C:24]3[C:29]4[CH:30]=[CH:31][S:32][C:28]=4[CH:27]=[CH:26][N:25]=3)[CH2:19][CH2:20]2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 109660274-(Piperazin-1-yl)thieno[3,2-c]pyridineHCID 178453924HCID 178453924, compound

Product 1

HCID 178453912HCID 178453912, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

trans-[4-(2-oxo-ethyl)-cyclohexyl]-carbamic acid tert-butyl ester [CAS-Nr. 215790-29-7] (1.0 g, 4 mmol) was added to a solution under N2 of commercially available 4-piperazine-1-yl-thieno[3,2-c]pyridine [CAS-Nr. 106261-27-2] (0.85 g, 4 mmol) in 1,2-dichloroethane (45 ml) and AcOH (0.22 ml, 4 mmol). The resulting reaction mixture was stirred 8 h at room temperature before addition of Na(AcO)3BH (1.2 g, 6 mmol). Stirring was continued over night at room temperature. Sat. aq. NaHCO3 sol. was added and the product was extracted with EtOAc (2×). The combined organic layers were washed with H2O and brine. After drying (MgSO4) the solvent was evaporated and the product was purified by flash chromatography on silica gel (CH2Cl2/MeOH, 100:0 to 90:10) to yield trans-{4-[2-(4-thieno[3,2-c]pyridin-4-yl-piperazin-1-yl)-ethyl]-cyclohexyl}-carbamic acid tert-butyl ester as a light yellow solid (1.2 g, 72%), MS (ISP) m/z=445.3 [(M+H)+].

Workup

  1. customThe resulting reaction mixture
  2. waitwas continued over night at room temperature
  3. extractionthe product was extracted with EtOAc (2×)
  4. washThe combined organic layers were washed with H2O and brine
  5. dry with materialAfter drying (MgSO4) the solvent
  6. customwas evaporated
  7. customthe product was purified by flash chromatography on silica gel (CH2Cl2/MeOH, 100:0 to 90:10)

Sources & evidence

ORD record
ord-376ab6342ae54c34a29a6ea0289ab0a1
Source dataset
uspto-grants-2013_11
Patent number
US08586579B2

Reaction notes

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