Water → HCID 86663799, compound

HRID 2370608Notes

Reaction equation

HRID 2370608 reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH3:46])[C:8](=[O:9])[N:7]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=2)[C:6](=[O:24])[N:5]1[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][S:34]([CH2:36][CH2:37][CH2:38][C:39]([F:45])([F:44])[C:40]([F:43])([F:42])[F:41])=[O:35].[CH3:47]I.O>CN(C=O)C>[CH3:3][C:4]1([CH3:46])[C:8](=[O:9])[N:7]([C:10]2[CH:15]=[CH:14][C:13]([N:16]([CH3:47])[C:17](=[O:19])[CH3:18])=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=2)[C:6](=[O:24])[N:5]1[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][S:34]([CH2:36][CH2:37][CH2:38][C:39]([F:45])([F:44])[C:40]([F:41])([F:42])[F:43])=[O:35]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodide2×HCID 24758Sodium hydride2×HCID 46944260HCID 46944260, compound

Product 1

HCID 86663799HCID 86663799, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

NaH (to 60%) (6 mg, 0.16 mmole) is added under argon to a solution of N-[4-(4,4-dimethyl-2,5-dioxo-3-{9-[(4,4,5,5,5-pentafluoropentyl)sulphinyl]-nonyl}imidazolidin-1-yl)-2 (trifluoromethyl)phenyl]acetamide (100 mg, 0.15 mmole) (prepared according to Example 18) in anhydrous DMF (2 ml). A release of gas accompanies the change in colour of the reaction medium. Stirring is maintained for 1 hour at 23° C. before adding methyl iodide (10 μl, 0.16 mmole). After reaction for 1 hour the same quantity of sodium hydride and methyl iodide as previously are added, then the reaction mixture is again stirred for 3 hours at 23° C. The reaction medium is poured into water (25 ml) and extracted with AcOEt (2×25 ml). The organic phases are combined and washed successively with water (25 ml) and salt water (25 ml). After drying over Na2SO4, the organic solution is filtered and concentrated under vacuum. The evaporation residue is purified on a silica column (eluent: CH2Cl2/MeOH: 95/5 to 90/10). The expected compound is obtained in the form of a colourless oil with a yield of 72% (72 mg).

Workup

  1. additionas previously are added
  2. stirringthe reaction mixture is again stirred for 3 hours at 23° C
  3. extractionextracted with AcOEt (2×25 ml)
  4. washwashed successively with water (25 ml) and salt water (25 ml)
  5. dry with materialAfter drying over Na2SO4
  6. filtrationthe organic solution is filtered
  7. concentrationconcentrated under vacuum
  8. customThe evaporation residue is purified on a silica column (eluent: CH2Cl2/MeOH: 95/5 to 90/10)

Sources & evidence

ORD record
ord-93c02975f0d94db2b356664dd52f1fa5
Source dataset
uspto-grants-2014_04
Patent number
US08710091B2

Reaction notes

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