2,4-Difluorophenyl isocyanate → N-[4-(2-chlorophenyl)-7,8-dihydro-6H-cyclopenta[g]quinolin-3-yl]-N'-(2,4-difluorophenyl)urea

HRID 258028Notes

Reaction equation

HRID 258028 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18])=[CH:9][C:8]1[CH2:19][CH2:20][CH2:21][C:7]=1[CH:6]=2.[F:22][C:23]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=1[N:30]=[C:31]=[O:32]>O1CCCC1>[Cl:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:11]1[C:10]2[C:5](=[CH:6][C:7]3[CH2:21][CH2:20][CH2:19][C:8]=3[CH:9]=2)[N:4]=[CH:3][C:2]=1[NH:1][C:31]([NH:30][C:24]1[CH:25]=[CH:26][C:27]([F:29])=[CH:28][C:23]=1[F:22])=[O:32]

Participants

4

Reactant 2

HCID 5932582,4-Difluorophenyl isocyanateHCID 152316043-amino-4-(2-chlorophenyl)-7,8-dihydro-6H-cyclopenta[g]quinoline

Product 1

HCID 9933440N-[4-(2-chlorophenyl)-7,8-dihydro-6H-cyclopenta[g]quinolin-3-yl]-N'-(2,4-difluorophenyl)urea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-amino-4-(2-chlorophenyl)-7,8-dihydro-6H-cyclopenta[g]quinoline (2.5 g) in tetrahydrofuran (25 ml) was added 2,4-difluorophenyl isocyanate (1.2 ml) dropwise and the mixture was stirred for 5 hours at room temperature. The solvent was then distilled off to give crystals of N-[4-(2-chlorophenyl)-7,8-dihydro-6H-cyclopenta[g]quinolin-3-yl]-N'-(2,4-difluorophenyl)urea. The crystals were collected by filtration and washed with isopropyl ether (3.42 g, 89.8%). Recrystallization from acetic acid-water gave colorless needles, m.p. 247°-248° C.

Workup

  1. distillationThe solvent was then distilled off

Sources & evidence

ORD record
ord-ef09ae006fd34a93947762a6dfbc9824
Source dataset
uspto-grants-1993_11
Patent number
US05264454

Reaction notes

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