Cesium carbonate → HCID 67287332, compound

HRID 922017Notes

Reaction equation

HRID 922017 reaction equation
Cl[C:2]1[N:7]=[C:6]([S:8][CH2:9][CH3:10])[C:5]([C:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)=[O:12])=[C:4]([CH3:22])[CH:3]=1.[CH3:23][O:24][CH:25]1[CH2:28][NH:27][CH2:26]1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1>[CH2:9]([S:8][C:6]1[C:5]([C:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)=[O:12])=[C:4]([CH3:22])[CH:3]=[C:2]([N:27]2[CH2:28][CH:25]([O:24][CH3:23])[CH2:26]2)[N:7]=1)[CH3:10]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 134019963-MethoxyazetidineHCID 866643146-chloro-2-ethylsulfanyl-N-[(3-fluorophenyl)-methyl]-4-methyl-pyridine-3-carboxylic acid amide

Product 1

HCID 67287332HCID 67287332, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 410 mg (1.2 mmol) 6-chloro-2-ethylsulfanyl-N-[(3-fluorophenyl)-methyl]-4-methyl-pyridine-3-carboxylic acid amide (synthesis is described in section b) of example 2), 125 mg (1.0 mmol) 3-methoxy-azetidine and 824 mg (2.53 mmol) Cs2CO3 in 1,4-dioxane (7 ml) was heated at 110° C. for 24 h. Subsequently the RM was concentrated in vacuo. The residue obtained was partitioned between water and EtOAc. The organic layer was separated, dried over MgSO4 and concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 3:1) provided 122 mg (0.31 mmol, 31%) 2-ethylsulfanyl-N-[(3-fluorophenyl)-methyl]-6-(3-methoxy-azetidin-1-yl)-4-methyl-pyridine-3-carboxylic acid amide (example 6). [M+H]+ 390.2.

Workup

  1. concentrationSubsequently the RM was concentrated in vacuo
  2. customThe residue obtained
  3. customwas partitioned between water and EtOAc
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by CC (hexane/EtOAc 3:1)

Sources & evidence

ORD record
ord-5a6c2c37032d46148fefffc2bebd394d
Source dataset
uspto-grants-2016_03
Patent number
US09278103B2

Reaction notes

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