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

HRID 353655

Reaction equation

HRID 353655 reaction equation
ClC(Cl)(Cl)COC([C:7]1[N:11]([C:12]2[CH:13]=[CH:14][C:15]([CH3:18])=[N:16][CH:17]=2)[N:10]=[C:9]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:8]=1N)=O.[NH2:26][C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:30]([O:37][CH2:38][C:39]2[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=2)=[CH:29][CH:28]=1.C([N:48]([CH:51](C)C)CC)(C)C.CS(C)=[O:56]>C(OCC)(=O)C>[C:19]([C:9]1[CH:8]=[C:7]([NH:48][C:51]([NH:26][C:27]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:30]([O:37][CH2:38][C:39]3[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=3)=[CH:29][CH:28]=2)=[O:56])[N:11]([C:12]2[CH:13]=[CH:14][C:15]([CH3:18])=[N:16][CH:17]=2)[N:10]=1)([CH3:20])([CH3:21])[CH3:22]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 159085354-(4-Pyridinylmethoxy)-1-naphthalenamineHCID 699124795-(2,2,2-Trichloroethoxycarbonyl)-amino3-t-butyl-1-(2-methylpyridin-5-yl)pyrazole

Product 1

HCID 99578531-[3-tert-butyl-1-(2-methylpyridin-5-yl)-1H-pyrazol-5-yl]-3-[4-(pyridin-4-yl-methoxy)naphthalen-1-yl]-urea

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-(2,2,2-trichloroethoxycarbonyl)-amino3-t-butyl-1-(2-methylpyridin-5-yl)pyrazole (26 mmol), 1-amino-4-(pyridin-4-ylmethoxy)naphthalene (26 mmol), diisopropylethylamine (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-6784645309ac4a51986ed40890f486f6
Source dataset
uspto-grants-2004_06
Patent number
US06753426B2

Linked notes

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