Cyclohexanecarbonyl chloride → (R)-(4-(4-chlorophthalazin-1-yl)-3-methylpiperazin-1-yl)(cyclohexyl)methanone

HRID 1689968Notes

Reaction equation

HRID 1689968 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][CH2:14][C@H:13]2[CH3:18])=[N:4][N:3]=1.[CH:19]1([C:25](Cl)=[O:26])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]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[CH2:17][CH2:16][N:15]([C:25]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[O:26])[CH2:14][C@H:13]2[CH3:18])=[N:4][N:3]=1

Participants

6

Reactant 2

HCID 75938Cyclohexanecarbonyl chlorideHCID 57581473(R)-1-chloro-4-(2-methylpiperazin-1-yl)phthalazine

Product 1

HCID 57581516(R)-(4-(4-chlorophthalazin-1-yl)-3-methylpiperazin-1-yl)(cyclohexyl)methanone

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 81531DiisopropylethylamineSolvent

Procedure

(R)-1-chloro-4-(2-methylpiperazin-1-yl)phthalazine (JK-2, 752 mg, 2.86 mmol) was dissolved in DMF (8 mL) and N,N-diisopropylethylamine (1.5 mL). Cyclohexanecarbonyl chloride (0.498 mL, 3.72 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/0-75% ethyl acetate gave an off-white foam. MS (M+H)+=373.1.

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-37c7b19d745947ea99785547781d23c8
Source dataset
uspto-grants-2012_04
Patent number
US08153633B2

Reaction notes

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