Cesium carbonate → HCID 69481098, compound

HRID 2364263Notes

Reaction equation

HRID 2364263 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:10]=[C:11]([NH:20][C:21](=O)[C:22](F)(F)F)[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:13][CH:14]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].ICC[N:36]1[CH2:41][CH2:40][CH2:39][CH2:38][S:37]1(=[O:43])=[O:42]>CN(C)C=O.C1(C)C=CC=CC=1>[O:42]=[S:37]1(=[O:43])[CH2:38][CH2:39][CH2:40][CH2:41][N:36]1[CH2:22][CH2:21][NH:20][C:11]1[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:13][CH:14]=[C:9]([CH2:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH:10]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonate2×HCID 69482774HCID 69482774, compound2×HCID 86612778HCID 86612778, compound

Product 1

HCID 69481098HCID 69481098, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl 5-[(4-fluorophenyl)methyl]-3-[(trifluoroacetyl)amino]-2-pyridinecarboxylate (304 mg, 0.821 mmol) in N,N-dimethylformamide (3 mL) was added cesium carbonate (535 mg, 1.64 mmol) and 2-(2-iodoethyl)tetrahydro-2H-1,2-thiazine 1,1-dioxide (356 mg, 1.23 mmol), respectively. The reaction mixture was stirred at 80° C. for 5 hours. Additional cesium carbonate (535 mg, 1.64 mmol) and 2-(2-iodoethyl)tetrahydro-2H-1,2-thiazine 1,1-dioxide (356 mg, 1.23 mmol) were added and the reaction mixture was stirred overnight at 80° C. The reaction mixture was cooled and diluted with toluene. The organic layer was washed with water and brine, then dried over sodium sulfate. Filtration and concentration, followed by flash chromatography (0 to 5%, methanol in dichloromethane) to provide ethyl 3-{[2-(1,1-dioxidotetrahydro-2H-1,2-thiazin-2-yl)ethyl]amino}-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate, which was slightly contaminated and taken on to the next step.

Workup

  1. stirringthe reaction mixture was stirred overnight at 80° C
  2. temperatureThe reaction mixture was cooled
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-47f5dc23a09f4cddab871f8e2283073a
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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