Acetonitrile → HCID 22244621, compound

HRID 891107Notes

Reaction equation

HRID 891107 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:5]([CH3:13])[N:4]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][NH:22][C:23](=[O:31])OC3C=CC=CC=3)=[CH:16][CH:15]=2)[N:3]=1.[OH:32][C:33]1[CH:38]=[CH:37][C:36]([S:39]([NH2:42])(=[O:41])=[O:40])=[CH:35][CH:34]=1.C(#N)C.CCCCCCC=CCCC>ClCCl>[CH3:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:5]([CH3:13])[N:4]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][NH:22][C:23]([NH:42][S:39]([C:36]3[CH:35]=[CH:34][C:33]([OH:32])=[CH:38][CH:37]=3)(=[O:40])=[O:41])=[O:31])=[CH:16][CH:15]=2)[N:3]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 74093p-HydroxybenzenesulfonamideHCID 136496Undec-4-eneHCID 22244550Phenyl 2-[4-(3,5-dimethyl-4-phenyl-1H-pyrazol-1-yl)phenyl]ethylcarbamate

Product 1

HCID 22244621HCID 22244621, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of phenyl 2-[4-(3,5-dimethyl-4-phenyl-1H-pyrazol-1-yl)phenyl]ethylcarbamate (step 1 of Example 22, 100 mg, 0.24 mmol), 4-hydroxybenzenesulfonamide (42 mg, 0.24 mmol), acetonitrile (3 mL) and 1,8-[5.4.0]-7-undecene (36 μL, 0.24 mmol) was stirred at room temperature for 16 h. The mixture was diluted with dichloromethane, and washed with 1 M hydrochloric acid and sat. NaHCO3 aq. The organic fraction was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by TLC with dichloromethane/methanol (10:1) to afford 89 mg (74%) of the title compound as white solids: 1H-NMR [CDCl3/CD3OD(4:1)] δ 7.73-7.68 (2H, m), 7.48-7.23 (9H, m), 6.88-6.83 (2H, m), 3.47 (2H, t, J=6.7 Hz), 2.84 (2H, t, J=6.7 Hz), 2.33 (3H, s), 2.26 (3H, s).

Workup

  1. washwashed with 1 M hydrochloric acid and sat. NaHCO3 aq. The organic fraction
  2. dry with materialwas dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by TLC with dichloromethane/methanol (10:1)

Sources & evidence

ORD record
ord-5072083ba70c449490023f339366b3fc
Source dataset
uspto-grants-2006_02
Patent number
US07001917B2

Reaction notes

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