Iodoethane → HCID 178464527, compound

HRID 853128Notes

Reaction equation

HRID 853128 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]([C@H:16]1[CH2:21][CH2:20][C@H:19]([NH:22][S:23]([C:26]2[N:27]=[C:28]([CH3:32])[N:29]([CH3:31])[CH:30]=2)(=[O:25])=[O:24])[CH2:18][CH2:17]1)([O:8][Si:9]([CH2:14][CH3:15])([CH2:12][CH3:13])[CH2:10][CH3:11])[C:4]([F:7])([F:6])[F:5].[CH2:35]1CCN2C(=NCCC2)C[CH2:36]1.C(I)C.[NH4+].[Cl-]>CN(C=O)C.CCOCC>[CH2:35]([N:22]([C@H:19]1[CH2:18][CH2:17][C@H:16]([C:3]([O:8][Si:9]([CH2:14][CH3:15])([CH2:10][CH3:11])[CH2:12][CH3:13])([C:4]([F:7])([F:6])[F:5])[C:2]([F:1])([F:33])[F:34])[CH2:21][CH2:20]1)[S:23]([C:26]1[N:27]=[C:28]([CH3:32])[N:29]([CH3:31])[CH:30]=1)(=[O:25])=[O:24])[CH3:36]

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 25517Ammonium ChlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178477577HCID 178477577, compound

Product 1

HCID 178464527HCID 178464527, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 150 mg (0.28 mmol) of trans 1,2-dimethyl-1H-imidazole-4-sulfonic acid [4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-cyclohexyl]-amide (example 9.1) in 1 mL of DMF was treated with 0.66 mL (0.44 mmol) of DBU, stirred for 15 min and treated with 0.9 mL (0.58 mmol) of ethyliodide. The mixture was stirred at 60° C. for 4 hrs and distributed between a saturated aqueous solution of NH4Cl and Et2O. Drying of the combined organic phases over Na2SO4 and evaporation of the solvent gave 150 mg (95%) of trans 1,2-dimethyl-1H-imidazole-4-sulfonic acid ethyl-[4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-cyclohexyl]-amide as a light yellow liquid, MS: 566 (M+H)+.

Workup

  1. stirringThe mixture was stirred at 60° C. for 4 hrs
  2. dry with materialDrying of the combined organic phases over Na2SO4 and evaporation of the solvent

Sources & evidence

ORD record
ord-fd1896526bd54d258c27b3e1771dff96
Source dataset
uspto-grants-2007_08
Patent number
US07253282B2

Reaction notes

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