Benzoyl chloride → HCID 57581494, compound

HRID 1689967Notes

Reaction equation

HRID 1689967 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][C@H:16]([CH3:18])[NH:15][CH2:14][C@@H:13]2[CH3:19])=[N:4][N:3]=1.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C=O)C.C(N(CC)C(C)C)(C)C.C(OCC)(=O)C>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([N:12]2[C@@H:13]([CH3:19])[CH2:14][N:15]([C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:27])[C@@H:16]([CH3:18])[CH2:17]2)=[N:4][N:3]=1

Participants

6

Reactant 2

HCID 7412Benzoyl chlorideHCID 57581543HCID 57581543, compound

Product 1

HCID 57581494HCID 57581494, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 81531DiisopropylethylamineSolvent

Procedure

1-chloro-4-((2S,5S)-2,5-dimethylpiperazin-1-yl)phthalazine (496 mg, 1.79 mmol) was dissolved in DMF (5 mL) and N,N-diisopropylethylamine (0.5 mL). Benzoyl chloride (0.23 mL, 2.02 mmol) was added and the mixture stirred at rt for 16 hours. The reaction was taken up in ethyl acetate (80 mL) and washed with aqueous K2CO3 (10%), water, and saturated sodium chloride. The organics were dried (MgSO4) and evaporated to give a yellow oil. Chromatography over silica gel with a gradient of hexanes/0-70% ethyl acetate gave off-white foam. MS (M+H)+=381.0.

Workup

  1. washwashed with aqueous K2CO3 (10%), water, and saturated sodium chloride
  2. dry with materialThe organics were dried (MgSO4)
  3. customevaporated
  4. customto give a yellow oil

Sources & evidence

ORD record
ord-767a527856814ffab9d4544b893375ad
Source dataset
uspto-grants-2012_04
Patent number
US08153633B2

Reaction notes

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