Cesium carbonate → HCID 66626238, compound

HRID 1950324Notes

Reaction equation

HRID 1950324 reaction equation
[CH2:1]([N:3]([C:13]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=1[CH:21]1[CH2:30][CH2:29][C:28]2[C:23](=[CH:24][CH:25]=[C:26]([O:31][CH3:32])[CH:27]=2)[CH2:22]1)[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)[CH3:2].[CH2:33]([O:40][C:41]([N:43]1[CH2:48][CH2:47][N:46]([C:49](=[O:52])[CH2:50]Cl)[CH2:45][CH2:44]1)=[O:42])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.[Cl-].[Na+].O>[CH2:33]([O:40][C:41]([N:43]1[CH2:44][CH2:45][N:46]([C:49](=[O:52])[CH2:50][O:11][C:8]2[CH:7]=[CH:6][C:5]([C:4](=[O:12])[N:3]([CH2:1][CH3:2])[C:13]3[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=3[CH:21]3[CH2:30][CH2:29][C:28]4[C:23](=[CH:24][CH:25]=[C:26]([O:31][CH3:32])[CH:27]=4)[CH2:22]3)=[CH:10][CH:9]=2)[CH2:47][CH2:48]1)=[O:42])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 54279882HCID 54279882, compoundHCID 57934373HCID 57934373, compound

Product 1

HCID 66626238HCID 66626238, compoundYield 137.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of N-ethyl-4-hydroxy-N-[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]benzamide (1.0 g) and 4-(2-chloroacetyl)piperazine-1-carboxylic acid benzyl ester (830 mg) in N,N-dimethylformamide (20 ml) was added cesium carbonate (1.0 g), and the solution was stirred for 1 hour at 60° C. To the reaction solution was added brine, the solution was extracted with ethyl acetate, then dried over anhydrous magnesium sulfate, and the solvent was evaporated in vacuo. The residue was purified by NH silica gel column chromatography (hexane-ethyl acetate-methanol system) to provide 4-{2-{4-{ethyl[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]carbamoyl}phenoxy}acetyl}piperazine-1-carboxylic acid benzyl ester (2.2 g). Synthesized from the total amount of this compound according to an analogous synthetic method to Example 22, N-ethyl-N-[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]-4-(2-oxo-2-piperazin-1-ylethoxy)benzamide (1.5 g) was used according to an analogous synthetic method to Example 160 to provide the title compound (300 mg).

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated in vacuo
  4. customThe residue was purified by NH silica gel column chromatography (hexane-ethyl acetate-methanol system)

Sources & evidence

ORD record
ord-c2e79248e7594491ad9f760e504782bc
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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