Triethylamine → HCID 9983704, compound

HRID 971155Notes

Reaction equation

HRID 971155 reaction equation
[NH:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][C:18]4[C:21]([C:32]([F:35])([F:34])[F:33])=[N:22][N:23]([C:24]5[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=5)[C:17]=4[C:16]3=[O:36])=[CH:11][CH:10]=2)[CH2:8][CH2:7]1.[O-][Mn](=O)(=O)=O.[K+].[CH3:43]CN(CC)CC.CO.C(Cl)Cl>O1CCOCC1.CO>[CH3:31][O:30][C:27]1[CH:28]=[CH:29][C:24]([N:23]2[C:17]3[C:16](=[O:36])[N:15]([C:12]4[CH:11]=[CH:10][C:9]([C:6]5([C:2]6[N:1]([CH3:43])[CH:5]=[CH:4][N:3]=6)[CH2:7][CH2:8]5)=[CH:14][CH:13]=4)[CH2:20][CH2:19][C:18]=3[C:21]([C:32]([F:33])([F:34])[F:35])=[N:22]2)=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 516875Potassium PermanganateHCID 21226129Dichloromethane methanolHCID 44581664HCID 44581664, compound

Product 1

HCID 9983704HCID 9983704, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

The product from Example 144 (0.08 g, 0.18 mmol) was dissolved in 1,4-dioxane (2.0 mL) and KMnO4 (spatula tip) was added. The reaction was heated to 80° C. for 12 h at rt. The reaction was filtered, concentrated, and purified via flash chromatography (silica, 100% EtOAc then 0.5% Et3N:10% MeOH/CH2Cl2 then 100% MeOH) to yield the title compound (0.06 g, yield: 72%). 1H NMR δ 7.44 (d, J=9.1 Hz, 2H), 7.24 (d, J=8.7 Hz, 2H), 6.98 (m, 4H), 4.07 (dd, J=2.9, 3.7 Hz, 2H), 3.81 (s, 3H), 3.48 (s, 2H), 3.12 (t, J=6.2 Hz, 2H), 1.44 (m, 2H), 1.21 (t, J=7.3 Hz, 2H) ppm.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. custompurified via flash chromatography (silica, 100% EtOAc

Sources & evidence

ORD record
ord-361ac7695139419aaf218662d40a857c
Source dataset
uspto-grants-2007_12
Patent number
US07312214B2

Reaction notes

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