Cesium carbonate → N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-(1,1-dimethylethoxy)-4-pyrimidinyl]-1-azetidinesulfonamide

HRID 2388752Notes

Reaction equation

HRID 2388752 reaction equation
[N:1]1([S:5]([NH2:8])(=[O:7])=[O:6])[CH2:4][CH2:3][CH2:2]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:50]1[CH:55]=[C:54]([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])[N:53]=[C:52]([S:61][CH2:62][C:63]2[CH:68]=[CH:67][CH:66]=[C:65]([F:69])[C:64]=2[F:70])[N:51]=1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:70][C:64]1[C:65]([F:69])=[CH:66][CH:67]=[CH:68][C:63]=1[CH2:62][S:61][C:52]1[N:51]=[C:50]([NH:8][S:5]([N:1]2[CH2:4][CH2:3][CH2:2]2)(=[O:7])=[O:6])[CH:55]=[C:54]([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])[N:53]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 450805661-AzetidinesulfonamideHCID 866198744-Chloro-2-[[(2,3-difluorophenyl)methyl]thio]-6-(1,1-dimethylethoxy)-pyrimidine

Product 1

HCID 59558746N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-(1,1-dimethylethoxy)-4-pyrimidinyl]-1-azetidinesulfonamide

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

The title compound was prepared according to the procedure outlined in example 1 step iv) using a mixture of azetidine-1-sulfonamide (prepared according to patent WO 2004/011443, 0.16 g), tris(dibenzylideneacetone)dipalladium (0) (70 mg), 2-dicyclohexylphosphino-2′,4′,6′-tri-isopropyl-1,1′-biphenyl (XPHOS) (36 mg), cesium carbonate (0.37 g) and 4-chloro-2-[[(2,3-difluorophenyl)methyl]thio]-6-(1,1-dimethylethoxy)-pyrimidine (the product from step i) (0.26 g) in dioxane (6 mL). Purification was by column chromatography on silica gel using EtOAc/isohexane (1:9 to 2:8 gradient) as eluent to give the title compound as a white solid.

Workup

  1. customThe title compound was prepared
  2. customPurification

Sources & evidence

ORD record
ord-d3cd56a624ad42b4b8bbed4d02236c64
Source dataset
uspto-grants-2012_09
Patent number
US08269002B2

Reaction notes

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