Sodium Bicarbonate → HCID 178453911, compound

HRID 2042402Notes

Reaction equation

HRID 2042402 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][O:32][C:28]=3[CH:27]=[CH:26][N:25]=2)[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.C([O-])(O)=O.[Na+]>ClCCCl.CO>[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][O: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 3

HCID 516892Sodium BicarbonateHCID 27948084-(Piperazin-1-yl)furo[3,2-c]pyridineHCID 178453924HCID 178453924, compound

Product 1

HCID 178453911HCID 178453911, compoundYield 52.9%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolvent

Procedure

trans-[4-(2-oxo-ethyl)-cyclohexyl]-carbamic acid tert-butyl ester [CAS-Nr. 215790-29-7] (4.1 g, 17 mmol) was added to a solution under N2 of commercially available 4-piperazine-1-yl-furo[3,2-c]pyridine [CAS-Nr. 81078-84-4] (3.1 g, 15 mmol) in 1,2-dichloroethane (40 ml) and MeOH (0.5 ml). The resulting yellow solution was stirred 8 h at room temperature before addition of Na(AcO)3BH (4.9 g, 23 mmol). Stirring was continued at room temperature for 18 h. The reaction mixture was poured on sat. aq. NaHCO3 sol. (130 ml) and the product was extracted with EtOAc (3×100 ml). The combined organic layers were washed with H2O (130 ml) and brine (100 ml). After drying (MgSO4) the solvent was evaporated and the product was purified by flash chromatography on silica gel (CH2Cl2/MeOH, 100:0 to 95:5) to yield trans-{4-[2-(4-furo[3,2-c]pyridin-4-yl-piperazin-1-yl)-ethyl]-cyclohexyl}-carbamic acid tert-butyl ester as white crystals (3.4 g, 52%), MS (ISP) m/z=429.4 [(M+H)+].

Workup

  1. extractionthe product was extracted with EtOAc (3×100 ml)
  2. washThe combined organic layers were washed with H2O (130 ml) and brine (100 ml)
  3. dry with materialAfter drying (MgSO4) the solvent
  4. customwas evaporated
  5. customthe product was purified by flash chromatography on silica gel (CH2Cl2/MeOH, 100:0 to 95:5)

Sources & evidence

ORD record
ord-c4e0b99ae2ed4ad9a69df450d3720ed2
Source dataset
uspto-grants-2013_11
Patent number
US08586579B2

Reaction notes

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