Cesium carbonate → ethyl (2R)-2-({6-[({5-[(tert-butylamino)carbonyl]-2-furyl}sulfonyl)amino]-2-[(2,3-difluorobenzyl)thio]pyrimidin-4-yl}oxy)propanoate

HRID 2388799Notes

Reaction equation

HRID 2388799 reaction equation
[NH2:1][S:2]([C:5]1[O:9][C:8]([C:10]([NH:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:7][CH:6]=1)(=[O:4])=[O:3].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+].[CH2:57]([O:59][C:60](=[O:81])[C@H:61]([O:63][C:64]1[CH:69]=[C:68](Cl)[N:67]=[C:66]([S:71][CH2:72][C:73]2[CH:78]=[CH:77][CH:76]=[C:75]([F:79])[C:74]=2[F:80])[N:65]=1)[CH3:62])[CH3:58]>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]>[C:13]([NH:12][C:10]([C:8]1[O:9][C:5]([S:2]([NH:1][C:68]2[N:67]=[C:66]([S:71][CH2:72][C:73]3[CH:78]=[CH:77][CH:76]=[C:75]([F:79])[C:74]=3[F:80])[N:65]=[C:64]([O:63][C@H:61]([CH3:62])[C:60]([O:59][CH2:57][CH3:58])=[O:81])[CH:69]=2)(=[O:4])=[O:3])=[CH:6][CH:7]=1)=[O:11])([CH3:16])([CH3:15])[CH3:14]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 473234015-(aminosulfonyl)-N-(tert-butyl)-2-furamideHCID 866198702-[[6-chloro-2-[[(2,3-difluorophenyl)methyl]thio]-4-pyrimidinyl]oxy](2R)-propanoic acid ethyl ester

Product 1

HCID 53628366ethyl (2R)-2-({6-[({5-[(tert-butylamino)carbonyl]-2-furyl}sulfonyl)amino]-2-[(2,3-difluorobenzyl)thio]pyrimidin-4-yl}oxy)propanoate

Reagents, catalysts & solvents 2

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

Procedure

The subtitle compound was prepared according to the procedure outlined in example 1 step (iv) using a mixture of 5-(aminosulfonyl)-N-(tert-butyl)-2-furamide (0.25 g), tris(dibenzylideneacetone)dipalladium (0) (58 mg), 2-dicyclohexylphosphino-2′,4′,6′-tri-isopropyl-1,1′-biphenyl (XPHOS) (30 mg), cesium carbonate (0.65 g) and 2-[[6-chloro-2-[[(2,3-difluorophenyl)methyl]thio]-4-pyrimidinyl]oxy]-(2R)-propanoic acid ethyl ester (product of Example 11 step i) (0.26 g) in dioxane (1.0 mL). Purification was trituration with Et2O to give the subtitle compound as a white solid. Yield: 0.25 g

Workup

  1. customThe subtitle compound was prepared
  2. customPurification

Sources & evidence

ORD record
ord-86d7c492ec9f450ba378f51343aa42c2
Source dataset
uspto-grants-2012_09
Patent number
US08269002B2

Reaction notes

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