Dimethyl Sulfoxide → HCID 21090460, compound

HRID 350851Notes

Reaction equation

HRID 350851 reaction equation
CS(C)=O.[CH3:5][C:6]([O:9][C:10]([NH:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)=[O:11])([CH3:8])[CH3:7].[F:19][C:20]1[CH:27]=[C:26](F)[CH:25]=[CH:24][C:21]=1[C:22]#[N:23].C(=O)([O-])[O-].[K+].[K+]>O>[C:22]([C:21]1[CH:24]=[CH:25][C:26]([N:16]2[CH2:15][CH2:14][CH:13]([NH:12][C:10](=[O:11])[O:9][C:6]([CH3:5])([CH3:7])[CH3:8])[CH2:18][CH2:17]2)=[CH:27][C:20]=1[F:19])#[N:23]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 775452,4-DifluorobenzonitrileHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 21090460HCID 21090460, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A DMSO (25 mL, 0.1 M) solution containing 4-N—BOC-aminopiperidine (500 mg, 2.5 mmol, 1.0 eq), 2,4-difluorobenzonitrile (348 mg, 2.5 mmol, 1.0 eq), and potassium carbonate (691 mg, 5.0 mmol, 2.0 eq) was heated to 100° C. for 18 h. The resulting mixture was cooled to RT, poured in H2O (ca 50 mL), and extracted (3×) with EtOAc. The combined extracts were washed (2×) with H2O, dried over MgSO4, and concentrated in vacuo. The resulting solid was purified via flash chromatography using 1:1 hexanes/EtOAc as the mobile phase. Isolated 530 mg (1.66 mmol, 66% yield).

Workup

  1. temperatureThe resulting mixture was cooled to RT
  2. extractionextracted (3×) with EtOAc
  3. washThe combined extracts were washed (2×) with H2O
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting solid was purified via flash chromatography
  7. customIsolated 530 mg (1.66 mmol, 66% yield)

Sources & evidence

ORD record
ord-5a2d26a4923949b7835ccb4e4916aee7
Source dataset
uspto-grants-2007_02
Patent number
US07183290B2

Reaction notes

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