Benzenesulfonyl chloride → HCID 57581525, compound

HRID 1689972Notes

Reaction equation

HRID 1689972 reaction equation
[CH3:1][C@@H:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:10][N:9]=2)[CH2:3]1.[C:24]1([S:30](Cl)(=[O:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C.C(N(CC)C(C)C)(C)C.C(OCC)(=O)C>[CH3:1][C@@H:2]1[N:7]([S:30]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:32])=[O:31])[CH2:6][CH2:5][N:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:10][N:9]=2)[CH2:3]1

Participants

6

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 57581519HCID 57581519, compound

Product 1

HCID 57581525HCID 57581525, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 81531DiisopropylethylamineSolvent

Procedure

Compound 67 was prepared as described in general Method F. (S)-1-(3-methylpiperazin-1-yl)-4-phenylphthalazine (JK-8) (150 mg, 0.493 mmol) was dissolved in DMF (3 mL) and N,N-diisopropylethylamine (0.400 mL). Benzenesulfonyl chloride (104 mg, 0.591 mmol) was added and the reaction stirred at rt for 18 hours. The reaction was taken up in ethyl acetate (75 mL) and washed with aqueous K2CO3 (10%), water, and saturated sodium chloride. The organics were dried (MgSO4) and evaporated to give a brown oil. Chromatography over silica gel with a gradient of hexanes/0-70% ethyl acetate gave 67 as an off-white solid. MS (M+H)+=445.2

Workup

  1. customCompound 67 was prepared
  2. washwashed with aqueous K2CO3 (10%), water, and saturated sodium chloride
  3. dry with materialThe organics were dried (MgSO4)
  4. customevaporated
  5. customto give a brown oil

Sources & evidence

ORD record
ord-83a16d00d7434777bf3acc95cf341240
Source dataset
uspto-grants-2012_04
Patent number
US08153633B2

Reaction notes

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