Cesium carbonate → HCID 178484081, compound

HRID 491771Notes

Reaction equation

HRID 491771 reaction equation
[CH3:1][N:2]([CH3:32])[C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([NH:11][C:12]2[C:16]3[CH:17]=[CH:18][C:19]([OH:21])=[CH:20][C:15]=3[O:14][C:13]=2[C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][N:26]=2)=[O:23])=[O:10])[CH2:5][CH2:4]1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42]>CN(C)C=O.O>[C:44]([O:43][C:41]([CH2:40][O:21][C:19]1[CH:18]=[CH:17][C:16]2[C:12]([NH:11][C:9]([C@H:6]3[CH2:5][CH2:4][C@H:3]([N:2]([CH3:32])[CH3:1])[CH2:8][CH2:7]3)=[O:10])=[C:13]([C:22]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][N:26]=3)=[O:23])[O:14][C:15]=2[CH:20]=1)=[O:42])([CH3:47])([CH3:46])[CH3:45]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 178484079HCID 178484079, compound

Product 1

HCID 178484081HCID 178484081, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Trans-3-[4-(dimethylamino)cyclohexylcarbonylamino]-6-hydroxy-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide (90 mg) obtained in Example 151 is dissolved in N,N-dimethylformamide (2 ml), and thereto are added cesium carbonate (110 mg) and t-butyl bromoacetate (35.5 μl). The mixture is stirred at room temperature for 12 hours, and further stirred at 50° C. for 2.5 hours. The reaction solution is allowed to stand for cooling, and diluted with water, and extracted with ethyl acetate. The organic layer is concentrated under reduced pressure, and the resulting residue is purified by NH-silica gel column chromatography (eluent: hexane/ethyl acetate=1/1, then ethyl acetate) to give the title compound (21 mg).

Workup

  1. stirringfurther stirred at 50° C. for 2.5 hours
  2. temperaturefor cooling
  3. extractionextracted with ethyl acetate
  4. concentrationThe organic layer is concentrated under reduced pressure
  5. customthe resulting residue is purified by NH-silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-493c126411774c1f8eebae57acaeb103
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

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