Benzoyl chloride → HCID 57581500, compound

HRID 1689953Notes

Reaction equation

HRID 1689953 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([N:12]2[CH2:17][CH2:16][NH:15][C@@H:14]([CH3:18])[CH2:13]2)=[N:4][N:3]=1.C(N(CC)CC)C.[C:26](Cl)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C([O-])(O)=O.[Na+]>ClCCl>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([N:12]2[CH2:17][CH2:16][N:15]([C:26]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:33])[C@@H:14]([CH3:18])[CH2:13]2)=[N:4][N:3]=1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 57581479HCID 57581479, compound

Product 1

HCID 57581500HCID 57581500, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-1-chloro-4-(3-methylpiperazin-1-yl)phthalazine (3.64 g, 13.9 mmol) was dissolved in dry dichloromethane (30 mL) and triethylamine (4.26 mL, 30.6 mmol). Benzoyl chloride (1.77 mL, 15.3 mmol) was added and stirred at rt for 1 hour. The reaction was added to saturated NaHCO3 (150 mL) and the aqueous layer was extracted with 3× dichloromethane. The combined organics were dried (MgSO4) and evaporated to give a yellow oil. Chromatography over silica gel with a gradient of hexanes/30-100% ethyl acetate gave an off-white solid. MS (M+H)+=367.1.

Workup

  1. extractionthe aqueous layer was extracted with 3× dichloromethane
  2. dry with materialThe combined organics were dried (MgSO4)
  3. customevaporated
  4. customto give a yellow oil

Sources & evidence

ORD record
ord-d54beb38cdb34e3591bf1094410af2d3
Source dataset
uspto-grants-2012_04
Patent number
US08153633B2

Reaction notes

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