Cesium carbonate → HCID 57126714, compound

HRID 842792Notes

Reaction equation

HRID 842792 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][CH:12]([NH:15][CH2:16][CH2:17][NH:18][C:19]([N:21]2[C@@H:25]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[C:28]([F:33])[CH:27]=3)[CH2:24][O:23][C:22]2=[O:34])=[O:20])[CH2:11][CH2:10]1)#[N:2].C(=O)([O-])[O-].[Cs+].[Cs+].[F:41][C:42]([F:46])([F:45])[CH2:43]I>C(#N)C.ClCCl.O>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][CH:12]([N:15]([CH2:43][C:42]([F:46])([F:45])[F:41])[CH2:16][CH2:17][NH:18][C:19]([N:21]2[C@@H:25]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[C:28]([F:33])[CH:27]=3)[CH2:24][O:23][C:22]2=[O:34])=[O:20])[CH2:11][CH2:10]1)#[N:2]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 677091,1,1-Trifluoro-2-iodoethaneHCID 57174532HCID 57174532, compound

Product 1

HCID 57126714HCID 57126714, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 18 (36 mg, 0.076 mmol) and cesium carbonate (50 mg, 0.153 mmol) in acetonitrile (100 mL) was treated with 2,2,2-trifluoroethyliodide (21.3 mg, 0.101 mmol) at room temperature. The resulting mixture was stirred at room temperature overnight. The mixture was diluted with dichloromethane and water and the aqueous layer was extracted with two additional portions of dichloromethane. The combined organic extracts were concentrated under reduced pressure and purified by PCTLC (SiO2, 4 mm, 1% NH4OEt-1% NH4OEt-10% EtOH-90% CHCl3) to afford the title compound (49) which was converted to the hydrochloride salt after treatment with EtOAc/HCl.

Workup

  1. extractionthe aqueous layer was extracted with two additional portions of dichloromethane
  2. concentrationThe combined organic extracts were concentrated under reduced pressure
  3. custompurified by PCTLC (SiO2, 4 mm, 1% NH4OEt-1% NH4OEt-10% EtOH-90% CHCl3)

Sources & evidence

ORD record
ord-36dae0ea45834ca7be9c899641ac5ca0
Source dataset
uspto-grants-2002_04
Patent number
US06376503B1

Reaction notes

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