Diisopropylethylamine → HCID 59700605, compound

HRID 902024Notes

Reaction equation

HRID 902024 reaction equation
[I-].[NH2:2][N+:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)C(C)C)(C)C.[Cl:18][C:19]1[N:24]=[C:23]([C:25](=O)[CH2:26][C:27]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[N:30]=[CH:29][CH:28]=2)[CH:22]=[CH:21][CH:20]=1>C(O)C>[Cl:18][C:19]1[N:24]=[C:23]([C:25]2[C:26]([C:27]3[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]=[CH:29][CH:28]=3)=[C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][N:3]3[N:2]=2)[CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2733704Pyridinium, 1-amino-, iodide (1:1)HCID 21992663HCID 21992663, compound

Product 1

HCID 59700605HCID 59700605, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

Add 1-aminopyridinium iodide (780 mg, 3.53 mmol), N,N-diisopropylethylamine (0.62 mL, 3.53 mmol), 1-(6-chloro-pyridin-2-yl)-2-quinolin-4-yl-ethanone (500 mg, 1.77 mmol), and ethanol (8 mL) to a sealed tube apparatus. The sealed vessel is heated at 110° C. for 5 hours. After cooling, the crude is concentrated in vacuo. Purification by flash column chromatography (Silica Gel, 25-40% acetone/hexanes) provides the title compound 119 mg (19%) as an orange solid.

Workup

  1. temperatureAfter cooling
  2. concentrationthe crude is concentrated in vacuo
  3. customPurification by flash column chromatography (Silica Gel, 25-40% acetone/hexanes)

Sources & evidence

ORD record
ord-4aa5bfcba0244271bc6ed9ee9b57fe79
Source dataset
uspto-grants-2008_04
Patent number
US07365066B2

Reaction notes

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