Cesium carbonate → HCID 90100619, compound

HRID 2207288Notes

Reaction equation

HRID 2207288 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][N:17]=[C:16]([N:20]4[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]4)[N:15]=3)[C:11]([OH:33])=[CH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[C:34]([O:38][C:39](=[O:58])[N:40]([S:46]([C:49]1[CH:54]=[C:53]([Cl:55])[C:52](F)=[CH:51][C:50]=1[F:57])(=[O:48])=[O:47])[C:41]1[N:42]=[CH:43][S:44][CH:45]=1)([CH3:37])([CH3:36])[CH3:35].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C)C=O>[C:34]([O:38][C:39]([N:40]([C:41]1[N:42]=[CH:43][S:44][CH:45]=1)[S:46]([C:49]1[C:50]([F:57])=[CH:51][C:52]([O:33][C:11]2[C:12]([C:14]3[CH:19]=[CH:18][N:17]=[C:16]([N:20]4[CH2:21][CH2:22][N:23]([C:26]([O:28][C:29]([CH3:30])([CH3:32])[CH3:31])=[O:27])[CH2:24][CH2:25]4)[N:15]=3)=[CH:13][C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)=[N:9][CH:10]=2)=[C:53]([Cl:55])[CH:54]=1)(=[O:48])=[O:47])=[O:58])([CH3:37])([CH3:35])[CH3:36]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 59436581Tert-butyl (5-chloro-2,4-difluorophenyl)sulfonyl(thiazol-4-yl)carbamateHCID 136623642HCID 136623642, compound

Product 1

HCID 90100619HCID 90100619, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10.0 mg (1.0 eq) of the obtained tert-butyl 4-(4-(2-(3-fluorophenyl)-5-hydroxypyridin-4-yl)pyrimidin-2-yl)piperazin-1-carboxylate and 9.1 mg (1.0 eq) of the obtained tert-butyl((5-chloro-2,4-difluorophenyl)sulfonyl)(thiazol-4-yl)carbamate were dissolved in 0.2 mL of N,N-dimethylformamide 0.2 mL, then 21.6 mg (3.0 eq) of Cs2CO3 was added thereto. The mixture was reacted at room temperature for 16 hours. The solvent was removed by concentrating under reduced pressure. The residue was separated by PLC (developing solvent, hexane:ethyl acetate=2:1) to obtain 10 mg of tert-butyl 4-(4-(5-(4-(N-(tert-butoxycarbonyl)-N-(thiazol-4-yl)sulfamoyl)-2-chloro-5-fluorophenoxy)-2-(3-fluorophenyl)pyridin-4-yl)pyrimidin-2-yl)piperazin-1-carboxylate.

Workup

  1. customThe mixture was reacted at room temperature for 16 hours
  2. customThe solvent was removed
  3. concentrationby concentrating under reduced pressure
  4. customThe residue was separated by PLC (developing solvent, hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-1f4e4b3dfaf340df93ff03d4c7011892
Source dataset
uspto-grants-2016_06
Patent number
US09376429B2

Reaction notes

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