Cesium carbonate → 4-[[[2-[[(2,3-Difluorophenyl)methyl]thio]-6-ethoxy-4-pyrimidinyl]amino]sulfonyl]-1-piperazinecarboxylic acid-1,1-dimethylethyl ester

HRID 2388749Notes

Reaction equation

HRID 2388749 reaction equation
[CH3:1][C:2]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:14]([NH2:17])(=[O:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])[CH3:3].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:25]1[CH:30]=[C:29]([O:31][CH2:32][CH3:33])[N:28]=[C:27]([S:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([F:42])[C:37]=2[F:43])[N:26]=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]>[CH3:4][C:2]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:14]([NH:17][C:25]2[CH:30]=[C:29]([O:31][CH2:32][CH3:33])[N:28]=[C:27]([S:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([F:42])[C:37]=3[F:43])[N:26]=2)(=[O:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:1])[CH3:3]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 53628347tert-Butyl 4-sulfamoylpiperazine-1-carboxylateHCID 866198724-Chloro-2-[[(2,3-difluorophenyl)methyl]thio)-6-ethoxy-pyrimidine2×

Product 1

HCID 536283464-[[[2-[[(2,3-Difluorophenyl)methyl]thio]-6-ethoxy-4-pyrimidinyl]amino]sulfonyl]-1-piperazinecarboxylic acid-1,1-dimethylethyl ester

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 4-(aminosulfonyl)-1-piperazinecarboxylic acid-1,1-dimethylethyl ester (the product from step i) (0.29 g), tris(dibenzylideneacetone)dipalladium (0) (67 mg), 2-dicyclohexylphosphiiao-2′,4′,6′-tri-isopropyl-1,1′-biphenyl (XPHOS) (35 mg), cesium carbonate (0.36 g) and 4-chloro-2-[[(2,3-difluorophenyl)methyl]thio]-6-ethoxy-pyrimidine (the product from example 14, step i) (0.23 g) in dioxane (5 mL). Purification was by column chromatography on silica using EtOAc/isohexane (1:9 to 1:3 gradient) as eluent to give the subtitle compound as a yellow oil. Yield: 0.25 g

Workup

  1. customThe subtitle compound was prepared
  2. customPurification

Sources & evidence

ORD record
ord-5ef3700037514f27a153234bb3658f9d
Source dataset
uspto-grants-2012_09
Patent number
US08269002B2

Reaction notes

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