Dimethyl Sulfoxide → HCID 58333635, compound

HRID 2066887Notes

Reaction equation

HRID 2066887 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([O:7][N:8]=[C:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][C:16]=3[F:25])[CH2:11][CH2:10]2)[CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.CS(C)=O.F[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][N:41]=1>CO>[N:1]1([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][N:41]=2)[CH2:6][CH2:5][CH:4]([O:7][N:8]=[C:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:22])=[O:23])=[CH:17][C:16]=3[F:25])[CH2:11][CH2:10]2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 97462-FluoropyridineHCID 81531DiisopropylethylamineHCID 866550221-(2-Fluoro-4-methanesulfonyl-phenyl)-piperidin-4-one O-piperidin-4-yl-oxime

Product 1

HCID 58333635HCID 58333635, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

30 mg of 63a (0.08 mmol), diisopropylethylamine (75 μL, 0.43 mmol), DMSO (0.3 mL) and 2-fluoropyridine (11.7 mg, 0.12 mmol) were combined and heated to 120° C. overnight. The mixture was diluted with methanol and purified on preparative HPLC to give 63-1: LC-MS 447.4 (MH+).

Workup

  1. custompurified on preparative HPLC
  2. customto give 63-1

Sources & evidence

ORD record
ord-6a750b79f7c04614a0a72fb0651e3e9c
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

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