Potassium Carbonate → HCID 67381275, compound

HRID 2409420Notes

Reaction equation

HRID 2409420 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]2[NH:7][C:8](=[O:16])[C:9]3[CH2:10][CH2:11][CH2:12][N:13]([CH3:15])[C:14]=3[C:5]=2[CH:4]=1.[Cl:19]CCl.B(Br)(Br)Br.C(=O)(O)[O-].[Na+].C(=O)([O-])[O-].[K+].[K+].[Cl:37]C[CH2:39][N:40]1[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1>ClCCl>[ClH:19].[ClH:37].[CH3:15][N:13]1[C:14]2[C:5]3[CH:4]=[C:3]([O:2][CH2:1][CH2:39][N:40]4[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]4)[CH:18]=[CH:17][C:6]=3[NH:7][C:8](=[O:16])[C:9]=2[CH2:10][CH2:11][CH2:12]1

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 748271-(2-Chloroethyl)piperidineHCID 516892Sodium BicarbonateHCID 22277759Boron tribromide dichloromethaneHCID 58424886HCID 58424886, compound

Product 1

HCID 67381275HCID 67381275, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound (50 mg, 0.20 mmol) prepared in step 2 was dissolved in dichloromethane (3 ml), added with 1 M boron tribromide dichloromethane solution (0.61 ml, 0.61 mmol) at 0° C. The resulting mixture was stirred for 18 hours at room temperature and poured into cold sodium bicarbonate aqueous solution. The mixture was extracted with ethyl acetate, dried over anhydrous sodium sulfate and concentrated to dryness. And then, the residue was dissolved in N,N-dimethylformamide (10 ml), added with potassium carbonate (72 mg, 0.52 mmol) and 1-(2-chloroethyl)piperidine (48 mg, 0.26 mmol). The resulting mixture was stirred for 18 hours at 90° C. and cooled to room temperature. The mixture was extracted with chloroform, dried over anhydrous sodium sulfate, and concentrated to dryness. The residue was purified by flash column chromatography (chloroform:methanol=7:1) to obtain the title compound (24.7 mg, yield: 34%, white solid). The obtained compound (23 mg, 0.067 mmol) was reacted in the same manner as in step 5 of Example 5 to obtain the title compound (21 mg, yield: 73%, yellow solid).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated to dryness
  4. dissolutionAnd then, the residue was dissolved in N,N-dimethylformamide (10 ml)
  5. stirringThe resulting mixture was stirred for 18 hours at 90° C.
  6. temperaturecooled to room temperature
  7. extractionThe mixture was extracted with chloroform
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated to dryness
  10. customThe residue was purified by flash column chromatography (chloroform:methanol=7:1)

Sources & evidence

ORD record
ord-b195b484492d40efa10e9fedd6a9f912
Source dataset
uspto-grants-2014_08
Patent number
US08815891B2

Reaction notes

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