Cesium carbonate → HCID 59558836, compound

HRID 1024978Notes

Reaction equation

HRID 1024978 reaction equation
[CH2:1]1[CH2:11]O[C:3](=[N+:4]2[CH2:9][CH2:8][N-:7][CH2:6][CH2:5]2)[CH2:2]1.[S:12]([NH2:16])(N)(=[O:14])=[O:13].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.[C:51](=O)([O-])[O-:52].[Cs+].[Cs+].Cl[C:58]1[CH:63]=[C:62]([O:64][CH3:65])[N:61]=[C:60]([S:66][CH2:67][C:68]2[CH:73]=[CH:72][CH:71]=[C:70]([F:74])[C:69]=2[F:75])[N:59]=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[F:75][C:69]1[C:70]([F:74])=[CH:71][CH:72]=[CH:73][C:68]=1[CH2:67][S:66][C:60]1[N:59]=[C:58]([NH:16][S:12]([N:7]2[CH2:6][CH2:5][N:4]([CH2:3][CH:2]3[CH2:1][CH2:11][CH2:51][O:52]3)[CH2:9][CH2:8]2)(=[O:14])=[O:13])[CH:63]=[C:62]([O:64][CH3:65])[N:61]=1

Participants

8

Reactant 5

HCID 10796Cesium carbonateHCID 82267SulfamideHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 53628394HCID 53628394, compoundHCID 866198774-Chloro-2-([(2,3-difluorophenyl)methyl]thio]-6-methoxypyrimidine2×

Product 1

HCID 59558836HCID 59558836, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent2×

Procedure

The title compound was prepared according to the procedure outlined in example 81 using a mixture of 1-(tetrahydrofuran-2-yl)-1-piperazine (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. Yield: 0.15 g

Workup

  1. customThe title compound was prepared
  2. customPurification

Sources & evidence

ORD record
ord-9cfacbdaeaed4efebdd9a1fb29419a12
Source dataset
uspto-grants-2014_05
Patent number
US08722883B2

Reaction notes

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