3-Fluorobenzoyl chloride → HCID 22597435, compound

HRID 1760217Notes

Reaction equation

HRID 1760217 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].[Cl:11][C:12]1[CH:17]=[C:16]([NH:18][C:19]2[C:24]([NH2:25])=[C:23]([Cl:26])[N:22]=[CH:21][N:20]=2)[CH:15]=[CH:14][N:13]=1>N1C=CC=CC=1.O.C(OCC)(=O)C>[Cl:26][C:23]1[C:24]([NH:25][C:5](=[O:6])[C:4]2[CH:8]=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=2)=[C:19]([NH:18][C:16]2[CH:15]=[CH:14][N:13]=[C:12]([Cl:11])[CH:17]=2)[N:20]=[CH:21][N:22]=1

Participants

6

Reactant 2

HCID 743763-Fluorobenzoyl chlorideHCID 22597404HCID 22597404, compound

Product 1

HCID 22597435HCID 22597435, compoundYield 62.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Fluorobenzoyl chloride (1.3 mL, 10.7 mmol) was added dropwise to a suspension of N4-(2-chloro-4-pyridyl)-6-chloro-4,5-pyrimidine diamine (2.5 g, 9.8 mmol) in pyridine (50 mL) over 5 minutes in a nitrogen atmosphere at 0 to 5° C., and the mixture was stirred as such for 12 hours. The reaction solution was diluted with water and ethyl acetate (100 mL). The organic layer was washed with 1N hydrochloric acid (×1). After the 1N hydrochloric acid layer was extracted with ethyl acetate (×2), the combined organic layers were washed with a saturated aqueous sodium bicarbonate solution (×1), dried over anhydrous sodium sulfate and concentrated. The residue was suspended in diethyl ether, and the solid was collected by filtration and washed with diethyl ether, to give the title compound (2.3 g, 62%) as a colorless solid.

Workup

  1. washThe organic layer was washed with 1N hydrochloric acid (×1)
  2. extractionAfter the 1N hydrochloric acid layer was extracted with ethyl acetate (×2)
  3. washthe combined organic layers were washed with a saturated aqueous sodium bicarbonate solution (×1)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. filtrationthe solid was collected by filtration
  7. washwashed with diethyl ether

Sources & evidence

ORD record
ord-3df67411ee2a46cab9e7c7eca6e6119d
Source dataset
uspto-grants-2005_01
Patent number
US06841549B1

Reaction notes

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