2,4-Difluorophenyl isocyanate → N-[4-(2-chlorophenyl)-2-ethylthieno[2,3-b]pyridin-5-yl]-N'-(2,4-difluorophenyl)urea

HRID 1657219Notes

Reaction equation

HRID 1657219 reaction equation
[NH2:1][C:2]1[C:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])=[C:4]2[CH:10]=[C:9]([CH2:11][CH3:12])[S:8][C:5]2=[N:6][CH:7]=1.[F:20][C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1[N:28]=[C:29]=[O:30]>O1CCCC1>[Cl:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:3]1[C:2]([NH:1][C:29]([NH:28][C:22]2[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:21]=2[F:20])=[O:30])=[CH:7][N:6]=[C:5]2[S:8][C:9]([CH2:11][CH3:12])=[CH:10][C:4]=12

Participants

4

Reactant 2

HCID 5932582,4-Difluorophenyl isocyanateHCID 197871805-Amino-4-(2-chlorophenyl)-2-ethylthieno[2,3-b]pyridine

Product 1

HCID 9889640N-[4-(2-chlorophenyl)-2-ethylthieno[2,3-b]pyridin-5-yl]-N'-(2,4-difluorophenyl)ureaYield 93.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-amino-4-(2-chlorophenyl)-2-ethylthieno[2,3-b]pyridine (288 mg) in tetrahydrofuran (3 ml) was added 2,4-difluorophenyl isocyanate (0.13 ml) and the mixture was stirred at room temperature for 18 hours, and then the solvent was distilled off. To the residue was added isopropyl ether to obtain N-[4-(2-chlorophenyl)-2-ethylthieno[2,3-b]pyridin-5-yl]-N'-(2,4-difluorophenyl)urea as crystals (416 mg, 93.9 %). Colorless prisms were obtained by recrystallization from acetone-hexane, mp: 217°-218° C.

Workup

  1. distillationthe solvent was distilled off
  2. additionTo the residue was added isopropyl ether

Sources & evidence

ORD record
ord-b192eb97969f4c4e9ef803e89ab51ffc
Source dataset
uspto-grants-1993_10
Patent number
US05256782

Reaction notes

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