Triethylamine → (2-Methyl-4-(4-phenylphthalazin-1-yl)piperazin-1-yl)(thiophen-2-yl)methanone

HRID 1689941Notes

Reaction equation

HRID 1689941 reaction equation
[CH3:1][CH: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(N(CC)CC)C.[S:31]1[CH:35]=[CH:34][CH:33]=[C:32]1[C:36](Cl)=[O:37]>ClCCl.C(OCC)(=O)C>[CH3:1][CH:2]1[CH2:3][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)[CH2:5][CH2:6][N:7]1[C:36]([C:32]1[S:31][CH:35]=[CH:34][CH:33]=1)=[O:37]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 789282-Thiophenecarbonyl chlorideHCID 575814991-(3-Methylpiperazin-1-yl)-4-phenylphthalazine

Product 1

HCID 25152617(2-Methyl-4-(4-phenylphthalazin-1-yl)piperazin-1-yl)(thiophen-2-yl)methanone

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(3-methylpiperazin-1-yl)-4-phenylphthalazine BSL-2 (200 mg, 0.58 mmol) in 10 mL dichloromethane was added triethylamine (0.23 mL, 1.6 mmol, 3 eq) and thiophene-2-carbonyl chloride (0.095 mL, 0.88 mmol, 1.5 eq). After 2 h, the reaction was diluted with ethyl acetate and washed with sat. NaHCO3, water, and brine. The organic layer was dried over MgSO4, filtered, and concentrated. Purification by column chromatography afforded (2-methyl-4-(4-phenylphthalazin-1-yl)piperazin-1-yl)(thiophen-2-yl)methanone, 1. MS (M+H)+=415.1.

Workup

  1. washwashed with sat. NaHCO3, water, and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by column chromatography

Sources & evidence

ORD record
ord-20ec7b1da29048a69e91a5bf087dc141
Source dataset
uspto-grants-2012_04
Patent number
US08153633B2

Reaction notes

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