Cesium carbonate → 2-Amino-N-{2-[(2,3-difluorobenzyl)thio]-6-methoxypyrimidin-4-yl}-4-methyl-1,3-thiazole-5-sulfonamide

HRID 1024930Notes

Reaction equation

HRID 1024930 reaction equation
[NH2:1][C:2]1[S:3][C:4]([S:8]([NH2:11])(=[O:10])=[O:9])=[C:5]([CH3:7])[N:6]=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:53]1[CH:58]=[C:57]([O:59][CH3:60])[N:56]=[C:55]([S:61][CH2:62][C:63]2[CH:68]=[CH:67][CH:66]=[C:65]([F:69])[C:64]=2[F:70])[N:54]=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]>[NH2:1][C:2]1[S:3][C:4]([S:8]([NH:11][C:53]2[CH:58]=[C:57]([O:59][CH3:60])[N:56]=[C:55]([S:61][CH2:62][C:63]3[CH:68]=[CH:67][CH:66]=[C:65]([F:69])[C:64]=3[F:70])[N:54]=2)(=[O:10])=[O:9])=[C:5]([CH3:7])[N:6]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 186932442-Amino-4-methyl-1,3-thiazole-5-sulfonamideHCID 866198774-Chloro-2-([(2,3-difluorophenyl)methyl]thio]-6-methoxypyrimidine2×

Product 1

HCID 595587902-Amino-N-{2-[(2,3-difluorobenzyl)thio]-6-methoxypyrimidin-4-yl}-4-methyl-1,3-thiazole-5-sulfonamide

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 2-amino-4-methyl-1,3-thiazole-5-sulfonamide (0.23 g), tris(dibenzylideneacetone)dipalladium (0) (73 mg), 2-dicyclohexylphosphino-2′,4′,6′-tri-isopropyl-1,1′-biphenyl (XPHOS) (38 mg), cesium carbonate (0.39 g) and 4-Chloro-2-[[(2,3-difluorophenyl)methyl]thio]-6-methoxypyrimidine (the product of Example 35, step i) (0.24 g) in dioxane (6 ml). The crude material was purified by column chromatography using EtOAc/isohexane (2:8 to 4.5:5.5 gradient) as eluent and trituration with Et2O to give the title compound as a beige solid. Yield: 0.15 g.

Workup

  1. customThe title compound was prepared
  2. customThe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-238feb2c47da456aa895d28cca82d005
Source dataset
uspto-grants-2014_05
Patent number
US08722883B2

Reaction notes

Loading…