Diisopropylethylamine → 1-Acetyl-N-(3-(N-(4-(benzofuran-2-yl)thiazol-2-yl)thiophene-2-carboxamido)propyl)piperidine-4-carboxamide
Reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]([C:13]1[S:14][CH:15]=[C:16]([C:18]2[O:19][C:20]3[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=3[CH:22]=2)[N:17]=1)[C:6]([C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)=[O:7].C(N(CC)C(C)C)(C)C.[C:36]([N:39]1[CH2:47][CH2:46][CH:42]([C:43](Cl)=[O:44])[CH2:41][CH2:40]1)(=[O:38])[CH3:37]>C(Cl)(Cl)Cl>[C:36]([N:39]1[CH2:40][CH2:41][CH:42]([C:43]([NH:1][CH2:2][CH2:3][CH2:4][N:5]([C:13]2[S:14][CH:15]=[C:16]([C:18]3[O:19][C:20]4[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=4[CH:22]=3)[N:17]=2)[C:6]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)=[O:7])=[O:44])[CH2:46][CH2:47]1)(=[O:38])[CH3:37]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of the amine prepared above (77 mg, 0.2 mmol) and N,N-diisopropylethylamine (139 μL, 0.8 mmol) was dissolved in chloroform (2 mL), and a portion of the solution (200 μL, 0.02 mmol) was added to a solution of 1-acetyl-isonipecotoyl chloride (7.6 mg, 0.04 mmol) in chloroform (200 μL). The reaction mixture was maintained at room temperature overnight.). The reaction mixture was maintained at room temperature overnight, then concentrated in vacuo. The resulting residue was dissolved in DMSO (200 μL) and subjected to HPLC purification (Method Z) to provide the title compound (4.5 mg) as a yellowish solid. LC/MS (ESI) m/z 537.1 [M+H]. HPLC retention time (Method C)=3.44 min.
Workup
- temperatureThe reaction mixture was maintained at room temperature overnight
- concentrationconcentrated in vacuo
- dissolutionThe resulting residue was dissolved in DMSO (200 μL)
- customsubjected to HPLC purification (Method Z)
Sources & evidence
- ORD record
- ord-ef07601b67f04e449d4f7c661541689b
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07795290B2
Reaction notes
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