Cesium carbonate → HCID 178505858, compound

HRID 452543Notes

Reaction equation

HRID 452543 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][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[C:25]([F:26])=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:16][CH2:15]1.C(=O)([O-])[O-].[Cs+].[Cs+].FC(F)(F)S(O[CH2:41][CH:42]([F:44])[F:43])(=O)=O>C(#N)C>[Cl:1][C:2]1[CH:28]=[CH:27][C:5]2[N:6]3[C:10]([CH2:11][N:12]([CH2:41][CH:42]([F:44])[F:43])[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[C:25]([F:26])=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27740892,2-Difluoroethyl trifluoromethanesulfonateHCID 178505857HCID 178505857, compound

Product 1

HCID 178505858HCID 178505858, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of trans-8-chloro-1-[4-(3-fluoro-pyridin-2-yl)-cyclohexyl]-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzo[e]azulene (50.0 mg, 0.126 mmol), cesium carbonate (81.9 mg, 0.251 mmol) and 2,2-difluoroethyl trifluoromethanesulfonate (53.8 mg, 0.251 mmol) in acetonitrile (0.6 ml) was stirred at room temperature for 20 h. The reaction mixture was partitioned between a water-brine mixture (1:1) (2 ml) and ethyl acetate (5 ml). The layers were separated. The aqueous layer was extracted with two 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 (24 mg, 37%) as off-white solid. MS m/e: 462 ([M+H]+)

Workup

  1. customThe reaction mixture was partitioned between a water-brine mixture (1:1) (2 ml) and ethyl acetate (5 ml)
  2. customThe layers were separated
  3. extractionThe aqueous layer was extracted with two 5-ml portions of ethyl acetate
  4. concentrationThe combined organic layers were concentrated in vacuo

Sources & evidence

ORD record
ord-c7b8830af5494185b34f2f925ef5c5a4
Source dataset
uspto-grants-2013_07
Patent number
US08492376B2

Reaction notes

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