Cesium carbonate → HCID 59558819, compound

HRID 1959036Notes

Reaction equation

HRID 1959036 reaction equation
[S:1]([NH2:5])([NH2:4])(=[O:3])=[O:2].C1(P([CH:34]2[CH2:39][CH2:38]CCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:47]1[CH:52]=[C:51]([O:53][CH3:54])[N:50]=[C:49]([S:55][CH2:56][C:57]2[CH:62]=[CH:61][CH:60]=[C:59]([F:63])[C:58]=2[F:64])[N:48]=1.O1[CH2:70][CH2:69]OCC1>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:64][C:58]1[C:59]([F:63])=[CH:60][CH:61]=[CH:62][C:57]=1[CH2:56][S:55][C:49]1[N:48]=[C:47]([NH:4][S:1]([N:5]2[CH2:70][CH2:69][N:50]([CH2:34][CH2:39][CH2:38][N:48]([CH3:49])[CH3:47])[CH2:51][CH2:52]2)(=[O:3])=[O:2])[CH:52]=[C:51]([O:53][CH3:54])[N:50]=1

Participants

7

Reactant 5

HCID 10796Cesium carbonateHCID 312751,4-Dioxane2×HCID 82267SulfamideHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 866198774-Chloro-2-([(2,3-difluorophenyl)methyl]thio]-6-methoxypyrimidine2×

Product 1

HCID 59558819HCID 59558819, compound

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

The title compound was prepared according to the procedure outlined in example 81 using a mixture of N,N-dimethyl-3-piperazi-1-ylpropan-1-amine (0.51 g), sulfamide (0.29 g) and dioxane (20 mL). Followed by tris(dibenzylideneacetone)dipalladium (0) (92 mg), 2-dicyclohexylphosphino-2′,4′,6′-tri-isopropyl-1,1′-biphenyl (XPHOS) (67 mg), cesium carbonate (0.49 g), 4-Chloro-2-[[(2,3-difluorophenyl)methyl]thio]-6-methoxypyrimidine (the product of example 35 step i) (0.30 g) and dioxane (10 mL). Purification was by reverse phase HPLC (symmetry as the stationary phase and TFA/acetonitrile as the mobile phase) then titurated with Toluene, MeOH followed by DCM to give the title compound as a white solid.

Workup

  1. customThe title compound was prepared
  2. customPurification

Sources & evidence

ORD record
ord-816aa941c1e54365972dabaf494490df
Source dataset
uspto-grants-2013_04
Patent number
US08410123B2

Reaction notes

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