Aniline → HCID 178512004, compound

HRID 2104803Notes

Reaction equation

HRID 2104803 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[C:13]([C:18]([F:21])([F:20])[F:19])[CH:14]=[CH:15][CH:16]=3)[N:11]=[CH:10][C:9]=2[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:23])[CH:5]=[CH:6][CH:7]=1.NC1C=CC=CC=1.[CH:37]1[N:41]=[CH:40][N:39]([C:42](N2C=NC=C2)=[NH:43])[CH:38]=1>C1COCC1>[C:22]([C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:8]=1[C:4]1[CH:3]=[C:2]([NH:1][C:42]([N:39]3[CH:38]=[CH:37][N:41]=[CH:40]3)=[NH:43])[CH:7]=[CH:6][CH:5]=1)=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([F:21])([F:19])[F:20])(=[O:23])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 11326798[4-(3-Aminophenyl)-8-(Trifluoromethyl)Quinolin-3-yl](Phenyl)MethanoneHCID 113556541-(1H-imidazole-1-carboximidoyl)-1H-imidazole

Product 1

HCID 178512004HCID 178512004, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To imidazole (65 mg, 9.760 mmol) in CH2Cl2 (10 ml) at room temperature under nitrogen atmosphere bromonitrile (500 mg, 4.71 mmol) was added. The resulting mixture was heated at reflux for 1 hr. Cooling to room temperature, filtration and concentration in vacuo to a volume of approximately 10 ml. The resulting pale liquor was let stand at 0° C. for 15 hrs. Filtration afforded a pale white powder for C-(di-imidazol-1-yl)-methyleneamine (210 mg, 28% yield). To [4-(3-amino-phenyl)-8-trifluoromethyl-quinolin-3-yl]-phenyl-methanone (132 mg, 3.389 mmol), aniline (213 mg, 2.347 mmol) and C-(di-imidazol-1-yl)-methyleneamine (420 mg, 2.608 mmol) in THF (20 mg) was heated at reflux for 2.5 hrs. Concentration in vacuo and RP-HPLC (gradient water:acetonitrile) afforded the title compound as a yellow powder (20 mg, 14% yield). MS (ESI) m/z 486.

Workup

  1. temperatureat reflux for 2.5 hrs
  2. concentrationConcentration in vacuo and RP-HPLC (gradient water:acetonitrile)

Sources & evidence

ORD record
ord-de46363854cf487bb31131d558d83f30
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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