Dimethylformamide → HCID 178472402, compound

HRID 2095653Notes

Reaction equation

HRID 2095653 reaction equation
[CH3:1][C:2]1[C:6]([I:7])=[C:5]([CH3:8])[NH:4][N:3]=1.[CH2:9]([O:11][C:12]([C@H:14]1[CH2:19][CH2:18][C@@H:17](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:16][CH2:15]1)=[O:13])[CH3:10].C([O-])([O-])=O.[K+].[K+].O1CCOCCOCCOCCOCCOCC1.CN(C=O)C>>[I:7][C:6]1[C:2]([CH3:1])=[N:3][N:4]([C@H:17]2[CH2:18][CH2:19][C@H:14]([C:12]([O:11][CH2:9][CH3:10])=[O:13])[CH2:15][CH2:16]2)[C:5]=1[CH3:8]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 971153,5-Dimethyl-4-iodo-1H-pyrazoleHCID 178472502HCID 178472502, compound

Product 1

HCID 178472402HCID 178472402, compound

Conditions

Temperature
80 °C

Procedure

A mixture of 3,5-dimethyl-4-iodopyrazole (300.0 mg, 1.351 mmol), cis-4-(toluene-4-sulfonyloxy)-cyclohexanecarboxylic acid ethyl ester (573.4 mg, 1.756 mmol), K2CO3 (373.5 mg, 2.702 mmol), 1,4,7,10,13,16-hexaoxacyclooctadecane (71.43 mg, 0.2702 mmol) and DMF (6 mL, 70 mmol) was heated to 80° C. overnight. The material was extracted with EtOAc, and washed with water (3×). The organic layer was dry-loaded onto silica gel for column chromatography, eluting with 10-20% EtOAc in hexanes. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a clear oil. MS (ES+): m/z=377.03 (100) [MH+]. HPLC: tR=3.74 min (polar—5 min, ZQ3).

Workup

  1. extractionThe material was extracted with EtOAc
  2. washwashed with water (3×)
  3. washeluting with 10-20% EtOAc in hexanes
  4. additionThe fractions containing the pure product
  5. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-71f0c1d7fd55455698e28c6ba0c13518
Source dataset
uspto-grants-2013_05
Patent number
US08445510B2

Reaction notes

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