2-Chloro-4-fluorobenzoyl chloride → HCID 58997395, compound

HRID 1716926Notes

Reaction equation

HRID 1716926 reaction equation
[CH2:1]([N:3]([CH:12]1[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]1)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[C:5]=1[F:11])[CH3:2].[Cl:19][C:20]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:21]=1[C:22](Cl)=[O:23]>O1CCOCC1.CO>[Cl:19][C:20]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:21]=1[C:22]([NH:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N:3]([CH2:1][CH3:2])[CH:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)[C:5]=1[F:11])=[O:23]

Participants

5

Reactant 2

HCID 27365462-Chloro-4-fluorobenzoyl chlorideHCID 58997293HCID 58997293, compound

Product 1

HCID 58997395HCID 58997395, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

Heat a mixture of N-ethyl-2-fluoro-N-(1-methyl-piperidin-4-yl)-benzene-1,3-diamine (Preparation 27) and 2-chloro-4-fluorobenzoyl chloride (23 mg) in 1,4-dioxane (5 mL) at reflux for 1 hour. Dilute with methanol (5 mL), load on a SCX column (10 g), wash with methanol, elute the product with 2M NH3 in methanol, evaporate to give the title compound: mass spectrum (electric spray) m/z=408 (M+1). Purify further by HPLC to give the di-trifluoroacetic acid salt.

Workup

  1. temperatureHeat
  2. temperatureat reflux for 1 hour
  3. washwash with methanol
  4. washelute the product with 2M NH3 in methanol
  5. customevaporate

Sources & evidence

ORD record
ord-9cec9db5372d42f1bfa97e24f5f3b819
Source dataset
uspto-grants-2010_09
Patent number
US07803813B2

Reaction notes

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