Cesium carbonate → HCID 178521212, compound

HRID 1433144Notes

Reaction equation

HRID 1433144 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[C:12]([N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)=[CH:11][NH:10][N:9]=2)[C:5]([OH:19])=[CH:4][C:3]=1[OH:20].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:28][CH2:29][OH:30]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[C:12]([N:13]3[CH2:18][CH2:17][N:16]([CH2:28][CH2:29][OH:30])[CH2:15][CH2:14]3)=[CH:11][NH:10][N:9]=2)[C:5]([OH:19])=[CH:4][C:3]=1[OH:20]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 108982-BromoethanolHCID 178516588HCID 178516588, compound

Product 1

HCID 178521212HCID 178521212, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-chloro-6-(4-piperazin-1-yl-1H-pyrazol-3-yl)-benzene-1,3-diol (43 mg, 0.146 mmol), cesium carbonate (48 mg, 0.146 mmol), 2-bromoethanol (0.025 ml, 0.35 mmol) and dimethylformamide (1 ml) was stirred at room temperature for 3 days. The mixture was evaporated to dryness and applied to a bond elute cartridge (5 g) with dichloromethane:methanol (49:1), then eluting with dichloromethane followed by dichloromethane:ethanol:ammonia (50:8:1 then 20:8:1) gave 4-chloro-6-{4-[4-(2-hydroxy-ethyl)-piperazin-1-yl]-1H-pyrazol-3-yl}-benzene-1,3-diol as a white solid (10 mg)

Workup

  1. customThe mixture was evaporated to dryness
  2. washelute cartridge (5 g) with dichloromethane:methanol (49:1)
  3. washeluting with dichloromethane

Sources & evidence

ORD record
ord-0cafba38849b43f099770f17673951e9
Source dataset
uspto-grants-2009_11
Patent number
US07612201B2

Reaction notes

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