Cesium carbonate → HCID 86761619, compound

HRID 2388867Notes

Reaction equation

HRID 2388867 reaction equation
C(OC(=O)N[C@H]1CCN(S(N)(=O)=O)C1)(C)(C)C.[CH2:18]([O:22][C:23](=[O:34])[NH:24][C@H:25]1[CH2:29][CH2:28][N:27]([S:30]([NH2:33])(=[O:32])=[O:31])[CH2:26]1)[CH2:19][CH2:20][CH3:21].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:76]1[CH:81]=[C:80]([O:82][CH3:83])[N:79]=[C:78]([S:84][CH2:85][C:86]2[CH:91]=[CH:90][CH:89]=[C:88]([F:92])[C:87]=2[F:93])[N:77]=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:93][C:87]1[C:88]([F:92])=[CH:89][CH:90]=[CH:91][C:86]=1[CH2:85][S:84][C:78]1[N:77]=[C:76]([NH:33][S:30]([N:27]2[CH2:28][CH2:29][C@H:25]([NH:24][C:23](=[O:34])[O:22][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:26]2)(=[O:31])=[O:32])[CH:81]=[C:80]([O:82][CH3:83])[N:79]=1

Participants

8

Reactant 5

HCID 10796Cesium carbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 53628401HCID 53628401, compoundHCID 866198774-Chloro-2-([(2,3-difluorophenyl)methyl]thio]-6-methoxypyrimidine2×HCID 131729953HCID 131729953, compound

Product 1

HCID 86761619HCID 86761619, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

A mixture of tert-butyl[(3S)-1-(aminosulfonyl)pyrrolidin-3-yl]carbamate (the product from step i), 0.525 g), tris(dibenzylideneacetone)dipalladium (0) (50 mg), 2-dicyclohexylphosphino-2′,4′,6′-tri-isopropyl-1,1′-biphenyl (XPHOS) (50 mg), cesium carbonate (0.429 g) and 4-Chloro-2-[[(2,3-difluorophenyl)methyl]thio]-6-methoxypyrimidine ((the product from example 35 step i), 0.400 g) in dioxane (20 ml) was heated at reflux in a microwave at 100° C., 300 W, open vessel with cooling for 40 mins. The reaction mixture was then reduced in vacuo and the residue separated between DCM (150 ml) and H2O (150 ml). The organics were separated and the aqueous layer was re-extracted with DCM (2×150 ml). Organics were combined, dried (MgSO4) and reduced in vacuo to give the subtitle compound as a yellow solid. Yield: 0.75 g

Workup

  1. temperaturewas heated
  2. temperature300 W, open vessel with cooling for 40 mins
  3. customthe residue separated between DCM (150 ml) and H2O (150 ml)
  4. customThe organics were separated
  5. extractionthe aqueous layer was re-extracted with DCM (2×150 ml)
  6. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-3d2cd958b5e64f5dafafeb5c01d00e07
Source dataset
uspto-grants-2012_09
Patent number
US08269002B2

Reaction notes

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