Potassium Carbonate → HCID 178519759, compound

HRID 2103685Notes

Reaction equation

HRID 2103685 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:5]2[N:6]=[C:7]([C@@H:9]3[CH2:12][C@H:11](O)[CH2:10]3)[S:8][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[NH:37]1[CH2:42][CH2:41][CH:40]([CH2:43][OH:44])[CH2:39][CH2:38]1>ClCCl>[Br:1][C:2]1[CH:15]=[CH:14][C:5]2[N:6]=[C:7]([C@H:9]3[CH2:12][C@H:11]([N:37]4[CH2:42][CH2:41][CH:40]([CH2:43][OH:44])[CH2:39][CH2:38]4)[CH2:10]3)[S:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 11430Potassium Carbonate2×HCID 67749Trifluoromethanesulfonic anhydrideHCID 4207714-PiperidinemethanolHCID 178521623HCID 178521623, compound

Product 1

HCID 178519759HCID 178519759, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of Example 1D (0.177 mmole) was dissolved in anhydrous dichloromethane (2 ml). Potassium carbonate (50 mg, 0.362 mmole) was added followed by trifluoromethanesulfonic anhydride (40 μl, 0.238 mmole). The mixture was allowed to stir at room temperature for 2 hours, then another portion of potassium carbonate (100 mg, 0.724 mmole) was added, followed by 4-piperidinemethanol (61 mg, 0.530 mmole). The resulting mixture was stirred at room temperature overnight. It was then quenched with water, and extracted three times with dichloromethane. The organic layers were combined, washed with brine, dried over sodium sulfate, and concentrated. The crude product was purified by column chromatography (0.3% ammonium hydroxide and 3% methanol in dichloromethane) to give 29 mg (43%) of title compound. 1H NMR (500 MHz, CDCl3) δ ppm 7.98 (d, J=1.83 Hz, 1H) 7.83 (d, J=8.54 Hz, 1H) 7.56 (dd, J=8.54, 1.83 Hz, 1H) 3.74-3.86 (m, 1H) 3.52 (d, J=6.10 Hz, 2H) 3.08-3.19 (m, 1H) 2.95 (d, J=10.68 Hz, 2H) 2.51-2.62 (m, 4H) 1.79 (d, J=10.68 Hz, 4H) 1.48-1.59 (m, 2H) 1.25-1.38 (m, 2H). MS: (M+H)+=381/383.

Workup

  1. stirringThe resulting mixture was stirred at room temperature overnight
  2. customIt was then quenched with water
  3. extractionextracted three times with dichloromethane
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography (0.3% ammonium hydroxide and 3% methanol in dichloromethane)

Sources & evidence

ORD record
ord-44f862197d5145ce9b1bd68ef5371836
Source dataset
uspto-grants-2009_08
Patent number
US07576110B2

Reaction notes

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