Acetic Acid → Methyl 4-[4-[(4-chlorophenyl)amino]-3-(4-methylpiperazin-1-yl)-4-oxobutyl]benzoate

HRID 1919894

Reaction equation

O=[CH:2][CH2:3][CH2:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]#[C-:23])=[CH:18][CH:17]=1.[CH3:24][N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.CC(O)=[O:33]>C(O)C(F)(F)F.CO>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:33])[CH:2]([N:28]2[CH2:29][CH2:30][N:25]([CH3:24])[CH2:26][CH2:27]2)[CH2:3][CH2:4][C:5]2[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=2)=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Methyl 4-(3-oxopropyl)benzoate (43.5 mg, 0.226 mmol), 4-chlorophenyl isocyanide (43.5 mg, 0.316 mmol), N-methylpiperazine (40.0 μL, 0.36 mmol) and AcOH (20.0 μL, 0.36 mmol) were dissolved in 100 μL of trifluoroethanol and heated at 50° C. for 3 hours. The reaction mixture was diluted with 2 mL of methanol and purified by reversed phase HPLC to afford the desired product. MS cal'd 430.2 (MH+), exp 430.1 (MH+).

Workup

custompurified by reversed phase HPLC

Sources & evidence

ORD record: ord-819eceeeada54589bf12a9cbdce3df7a
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08168658B2

Linked notes

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