Tetrahydrofuran → HCID 19787200, compound

HRID 1885198Notes

Reaction equation

HRID 1885198 reaction equation
C(O)C.Cl.[NH2:5][C:6]1[C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])=[C:8]2[CH:14]=[C:13]([Cl:15])[S:12][C:9]2=[N:10][CH:11]=1.O1CCCC1.[F:28][C:29]1[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:30]=1[N:36]=[C:37]=[O:38]>C(N(CC)CC)C>[Cl:15][C:13]1[S:12][C:9]2=[N:10][CH:11]=[C:6]([NH:5][C:37]([NH:36][C:30]3[CH:31]=[CH:32][C:33]([F:35])=[CH:34][C:29]=3[F:28])=[O:38])[C:7]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[CH3:22])=[C:8]2[CH:14]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 5932582,4-Difluorophenyl isocyanateHCID 19787197HCID 19787197, compound

Product 1

HCID 19787200HCID 19787200, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a mixture of 5-amino-2-chloro-4-(2-methylphenyl)thieno[2,3-b]pyridine hydrochloride ethanol solvate (160 mg) and tetrahydrofuran (3 ml) were added dropwise triethylamine (0.07 ml) and 2,4-difluorophenyl isocyanate (0.12 ml). The mixture was stirred at room temperature for 5 hours and the solvent was distilled off. Water was added to the residue and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over MgSO4 and the solvent was distilled off. To the residue was added isopropyl ether to obtain N-[2-chloro-4-(2-methylphenyl)thieno[2,3-b]pyridin-5-yl]-N'-[2,4-difluorophenyl)urea (133 mg, 68.9%) as crystals. crystals were recrystallized from ethanol to obtain colorless prisms, mp; 225°-226° C.

Workup

  1. distillationthe solvent was distilled off
  2. additionWater was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over MgSO4
  6. distillationthe solvent was distilled off
  7. additionTo the residue was added isopropyl ether

Sources & evidence

ORD record
ord-9fea3760fb404e188ad13d59ae893bef
Source dataset
uspto-grants-1992_09
Patent number
US05143919

Reaction notes

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