Cesium carbonate → N-{5-[({2-[(2,3-Difluorobenzyl)thio]-6-methoxypyrimidin-4-yl)amino)sulfonyl]-4-methyl-1,3-thiazol-2-yl]acetamide

HRID 1958983Notes

Reaction equation

HRID 1958983 reaction equation
[NH2:1][S:2]([C:5]1[S:9][C:8]([NH:10][C:11](=[O:13])[CH3:12])=[N:7][C:6]=1[CH3:14])(=[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+].Cl[C:56]1[CH:61]=[C:60]([O:62][CH3:63])[N:59]=[C:58]([S:64][CH2:65][C:66]2[CH:71]=[CH:70][CH:69]=[C:68]([F:72])[C:67]=2[F:73])[N:57]=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:73][C:67]1[C:68]([F:72])=[CH:69][CH:70]=[CH:71][C:66]=1[CH2:65][S:64][C:58]1[N:57]=[C:56]([NH:1][S:2]([C:5]2[S:9][C:8]([NH:10][C:11](=[O:13])[CH3:12])=[N:7][C:6]=2[CH3:14])(=[O:3])=[O:4])[CH:61]=[C:60]([O:62][CH3:63])[N:59]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 3244062N-(4-methyl-5-sulfamoylthiazol-2-yl)acetamideHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 866198774-Chloro-2-([(2,3-difluorophenyl)methyl]thio]-6-methoxypyrimidine2×

Product 1

HCID 59558795N-{5-[({2-[(2,3-Difluorobenzyl)thio]-6-methoxypyrimidin-4-yl)amino)sulfonyl]-4-methyl-1,3-thiazol-2-yl]acetamide

Reagents, catalysts & solvents 2

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

Procedure

The title compound was prepared according to the procedure outlined in example 1 step (iv) using a mixture of N-[5-(aminosulfonyl)-4-methyl-1,3-thiazol-2-yl]acetamide (0.25 g), tris(dibenzylideneacetone)dipalladium (0) (64 mg), 2-dicyclohexylphosphino-2′,4′,6′-tri-isopropyl-1,1′-biphenyl (XPHOS) (33 mg), cesium carbonate (0.69 g) and 4-Chloro-2-[[(2,3-difluorophenyl)methyl]thio]-6-methoxypyrimidine (the product of Example 35, step i) (0.21 g) in dioxane (6 ml). The crude material was purified by column chromatography using EtOAc/isohexane (2.5:7.5 to 4:6 gradient) as eluent to give the title compound as a pale yellow solid. Yield: 85 mg.

Workup

  1. customThe title compound was prepared
  2. customThe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-3fb379252a074c3885b224e69eaec31e
Source dataset
uspto-grants-2013_04
Patent number
US08410123B2

Reaction notes

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