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 1024921Notes

Reaction equation

HRID 1024921 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].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:23]([O:25][C:26](=[O:47])[C@H:27]([O:29][C:30]1[CH:35]=[C:34](Cl)[N:33]=[C:32]([S:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([F:45])[C:40]=2[F:46])[N:31]=1)[CH3:28])[CH3:24]>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:34]2[N:33]=[C:32]([S:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[C:41]([F:45])[C:40]=3[F:46])[N:31]=[C:30]([O:29][C@H:27]([CH3:28])[C:26]([O:25][CH2:23][CH3:24])=[O:47])[CH:35]=2)(=[O:4])=[O:3])=[CH:6][CH:7]=1)=[O:11])([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 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′-diphenyl (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 (10 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-7fb8488b13d1485495029ec047123d28
Source dataset
uspto-grants-2014_05
Patent number
US08722883B2

Reaction notes

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