4-(Piperazin-1-yl)furo[3,2-c]pyridine → HCID 178474979, compound

HRID 2042410Notes

Reaction equation

HRID 2042410 reaction equation
[N:1]1([C:7]2[C:12]3[CH:13]=[CH:14][O:15][C:11]=3[CH:10]=[CH:9][N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.O=[CH:17][CH2:18][C@H:19]1[CH2:24][CH2:23][C@H:22]([NH:25][C:26](=[O:28])[CH3:27])[CH2:21][CH2:20]1>ClCCCl.CO>[O:15]1[C:11]2[CH:10]=[CH:9][N:8]=[C:7]([N:1]3[CH2:2][CH2:3][N:4]([CH2:17][CH2:18][C@H:19]4[CH2:24][CH2:23][C@H:22]([NH:25][C:26](=[O:28])[CH3:27])[CH2:21][CH2:20]4)[CH2:5][CH2:6]3)[C:12]=2[CH:13]=[CH:14]1

Participants

5

Reactant 2

HCID 27948084-(Piperazin-1-yl)furo[3,2-c]pyridineHCID 178474986HCID 178474986, compound

Product 1

HCID 178474979HCID 178474979, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 111,2-DichloroethaneSolvent

Procedure

To a solution under N2 of commercially available 4-piperazine-1-yl-furo[3,2-c]pyridine [CAS-Nr. 81078-84-4] (125 mg, 0.62 mmol) in 1,2-dichloroethane (1.25 ml) were added trans-N-[4-(2-oxo-ethyl)-cyclohexyl]-acetamide [CAS-Nr. 946599-01-5, WO 2007/093540] (124 mg, 0.68 mmol) and 3 drops of MeOH. The resulting yellow solution was stirred 18 h at room temperature before addition of Na(AcO)3BH (196 mg, 0.92 mmol). After stirring 18 h at room temperature the reaction mixture was partitioned between sat. aq. NaHCO3 sol. (50 ml) and EtOAc (50 ml). The aqueous layer was extracted with more EtOAc (2×25 ml). The combined organic layers were washed with H2O (40 ml) and brine (40 ml) and dried over MgSO4. After evaporation of the solvent, the crude product (yellow crystals) was purified by flash chromatography on silica gel (CH2Cl2/MeOH, 100:0 to 95:5) to yield the title compound as light yellow crystals (95 mg, 42%), MS (ISP) m/z=371.2 [(M+H)+].

Workup

  1. customwas partitioned between sat. aq. NaHCO3 sol. (50 ml) and EtOAc (50 ml)
  2. extractionThe aqueous layer was extracted with more EtOAc (2×25 ml)
  3. washThe combined organic layers were washed with H2O (40 ml) and brine (40 ml)
  4. dry with materialdried over MgSO4
  5. customAfter evaporation of the solvent
  6. customthe crude product (yellow crystals) was purified by flash chromatography on silica gel (CH2Cl2/MeOH, 100:0 to 95:5)

Sources & evidence

ORD record
ord-579be3c86eb445e4b69d06235a69e541
Source dataset
uspto-grants-2013_11
Patent number
US08586579B2

Reaction notes

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