Cesium carbonate → HCID 178426062, compound

HRID 1893375Notes

Reaction equation

HRID 1893375 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]3[C:10]([CH2:11][NH:12][CH2:13][C:4]=2[CH:3]=1)=[N:9][N:8]=[C:7]3[C@H:14]1[CH2:19][CH2:18][C@H:17]([C:20]2[CH:24]=[C:23]([CH3:25])[O:22][N:21]=2)[CH2:16][CH2:15]1.C(=O)([O-])[O-].[Cs+].[Cs+].FC(F)(F)S(O[CH2:40][CH:41]([F:43])[F:42])(=O)=O>C(#N)C>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]3[C:10]([CH2:11][N:12]([CH2:40][CH:41]([F:43])[F:42])[CH2:13][C:4]=2[CH:3]=1)=[N:9][N:8]=[C:7]3[C@H:14]1[CH2:15][CH2:16][C@H:17]([C:20]2[CH:24]=[C:23]([CH3:25])[O:22][N:21]=2)[CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27740892,2-Difluoroethyl trifluoromethanesulfonateHCID 178426061HCID 178426061, compound

Product 1

HCID 178426062HCID 178426062, compoundYield 22.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of trans-8-chloro-1-[4-(5-methyl-isoxazol-3-yl)-cyclohexyl]-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzo[e]azulene (50.0 mg, 0.130 mmol), cesium carbonate (84.9 mg, 0.261 mmol) and 2,2-difluoroethyl trifluoromethanesulfonate (41.8 mg, 0.195 mmol) in acetonitrile (1.3 ml) was heated at 70° C. for 20 h. After cooling to room temperature the reaction mixture was partitioned between 1 M aqueous sodium hydroxide solution (2 ml) and ethyl acetate (5 ml). The layers were separated. The aqueous layer was extracted with three 5-ml portions of ethyl acetate. The combined organic layers were concentrated in vacuo. Preparative RP-HPLC with water (0.05% formic acid)/methanol as eluent gave the title compound (13 mg, 21%) as off-white solid. MS m/e: 448 ([M+H]+).

Workup

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. customwas partitioned between 1 M aqueous sodium hydroxide solution (2 ml) and ethyl acetate (5 ml)
  3. customThe layers were separated
  4. extractionThe aqueous layer was extracted with three 5-ml portions of ethyl acetate
  5. concentrationThe combined organic layers were concentrated in vacuo

Sources & evidence

ORD record
ord-5ef3a3d84b084f9e96e3a211c4b5ace3
Source dataset
uspto-grants-2013_08
Patent number
US08513238B2

Reaction notes

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