Dimethyl Sulfoxide → 1-[3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl]-3-[4-(2-pyridin-4-yl-ethenyl)naphthalen-1-yl]-urea

HRID 2182014Notes

Reaction equation

HRID 2182014 reaction equation
ClC(Cl)(Cl)C[O:4][C:5]([NH:7][C:8]1[N:12]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[N:11]=[C:10]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:9]=1)=O.[NH2:26][C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:30]([CH:37]=[CH:38][C:39]2[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=2)=[CH:29][CH:28]=1.C(N(C(C)C)CC)(C)C.CS(C)=O>C(OCC)(=O)C>[C:20]([C:10]1[CH:9]=[C:8]([NH:7][C:5]([NH:26][C:27]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:30]([CH:37]=[CH:38][C:39]3[CH:40]=[CH:41][N:42]=[CH:43][CH:44]=3)=[CH:29][CH:28]=2)=[O:4])[N:12]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[N:11]=1)([CH3:23])([CH3:21])[CH3:22]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 99310942,2,2-Trichloroethyl 3-tert-butyl-1-P-tolyl-1H-pyrazol-5-ylcarbamateHCID 696931651-Amino4-(2-pyridin-4-yl-ethenyl)naphthalene

Product 1

HCID 541515051-[3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl]-3-[4-(2-pyridin-4-yl-ethenyl)naphthalen-1-yl]-urea

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-(2,2,2-trichloroethoxycarbonyl)amino-3-t-butyl-1-p-tolylpyrazole (26 mmol), 1-amino-4-(2-pyridin-4-yl-ethenyl)naphthalene (26 mmol), diisopropylethylamine (3.2 g, 25 mmol) and DMSO (75 mL) is heated to 55-90° C. and held for 2-8 h. To this solution, ethyl acetate (100 mL) is added. The organic layer is washed with brine (4×50 mL), and dried over MgSO4. The solvent is removed under reduced pressure, and residue is crystallized from a suitable solvent such as acetonitrile (50 mL) at 0° C. The product is collected by filtration and recrystallized from a suitable solvent such as isopropanol and dried in vacuum to constant weight.

Workup

  1. washThe organic layer is washed with brine (4×50 mL)
  2. dry with materialdried over MgSO4
  3. customThe solvent is removed under reduced pressure, and residue
  4. customis crystallized from a suitable solvent such as acetonitrile (50 mL) at 0° C
  5. filtrationThe product is collected by filtration
  6. customrecrystallized from a suitable solvent such as isopropanol
  7. customdried in vacuum to constant weight

Sources & evidence

ORD record
ord-3cae7696aa5b459f87cf0bc25e39c553
Source dataset
uspto-grants-2005_05
Patent number
US06894173B2

Reaction notes

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