p-Toluenesulfonic acid → HCID 86643500, compound

HRID 659958Notes

Reaction equation

HRID 659958 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[F:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([C:22]2[CH:27]=[CH:26][N:25]=[C:24]([S:28][CH3:29])[N:23]=2)=O)=[CH:15][CH:14]=1.[NH2:30][C:31]1[C:32]([Cl:37])=[N:33][CH:34]=[CH:35][CH:36]=1.O.C1(C)C=CC=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.CCCCCC>[Cl:37][C:32]1[C:31]([N:30]=[C:20]([C:22]2[CH:27]=[CH:26][N:25]=[C:24]([S:28][CH3:29])[N:23]=2)[CH2:19][C:16]2[CH:17]=[CH:18][C:13]([F:12])=[CH:14][CH:15]=2)=[CH:36][CH:35]=[CH:34][N:33]=1

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 805282-Chloro-3-pyridylamineHCID 22272177Toluene waterHCID 68430510HCID 68430510, compound

Product 1

HCID 86643500HCID 86643500, compoundYield 49.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A mixture of p-toluenesulfonic acid (10 mg), 2-(4-Fluoro-phenyl)-1-(2-methylthio-pyrimidin-4-yl)-ethanone (200 mg, 0.76 mmoles) and 3-amino-2-chloropyridine (90 mg, 0.7 mmoles) in 3 mL of toluene was refluxed overnight with a Dean-Stark removal of water/toluene azeotrope. The reaction mixture was further concentrated, the brown residue suspended in an ethyl acetate/hexane mixture (9/1) and filtered. The solid was solubilised in ethyl acetate and purified by chromatography on silica gel (ethylacetate/hexane 1/1) to give 130 mg of (2-Chloro-pyridin-3-yl)-[2-(4-fluoro-phenyl)-1-(2-methylthio-pyrimidin-4-yl)-ethylidene]-amine as a brown oil.

Workup

  1. filtrationfiltered
  2. custompurified by chromatography on silica gel (ethylacetate/hexane 1/1)

Sources & evidence

ORD record
ord-a07094c3b3514f33a195038242b7295b
Source dataset
uspto-grants-2011_12
Patent number
US08084395B2

Reaction notes

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