Iodoethane → HCID 86700239, compound

HRID 879432Notes

Reaction equation

HRID 879432 reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:32]([CH3:33])=[CH:31][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([N:25]4[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]4)[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:34]1[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:48][CH3:49]>CN(C=O)C.C(OCC)(=O)C>[C:1]([O:5][C@@H:6]([C:12]1[C:32]([CH3:33])=[CH:31][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([N:25]4[CH2:26][CH2:27][N:28]([CH2:48][CH3:49])[CH2:29][CH2:30]4)[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:34]1[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 6340Iodoethane3×HCID 10796Cesium carbonateHCID 86700238HCID 86700238, compound

Product 1

HCID 86700239HCID 86700239, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of crude (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-(piperazin-1-yl)pyridin-4-yl)benzo[d]thiazol-6-yl)acetate (˜0.144 mmol) in DMF (1.5 mL) was added cesium carbonate (0.094 g, 0.288 mmol), followed by iodoethane (12.6 μL, 0.158 mmol). Reaction mixture was stirred for 1 h, then more iodoethane (5 μL) was added and reaction mixture stirred for 2 h. LC/MS showed incomplete reaction, so more iodoethane (5 μL) was added and reaction mixture stirred overnight. Reaction mixture was diluted with ethyl acetate, washed with 5% lithium chloride solution (2×), brine, dried (MgSO4), filtered, concentrated and purified by CombiFlash (0 to 10% MeOH/CH2Cl2) to give product. LCMS-ESI+: calc'd for C33H40ClN4O3S: 607.2 (M+H+); Found: 607.3 (M+H+).

Workup

  1. customReaction mixture
  2. customreaction mixture
  3. stirringstirred for 2 h
  4. customreaction
  5. customreaction mixture
  6. stirringstirred overnight
  7. customReaction mixture
  8. washwashed with 5% lithium chloride solution (2×), brine
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. custompurified by CombiFlash (0 to 10% MeOH/CH2Cl2)
  13. customto give product

Sources & evidence

ORD record
ord-944951b4850f407ab4490a3d2670b286
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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