Potassium Carbonate → HCID 58266274, compound

HRID 2039689Notes

Reaction equation

HRID 2039689 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:13]([CH3:20])[N:12]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)[C:11](=[O:31])[NH:10]2)=[CH:5][CH:4]=1)#[N:2].Br[CH2:33][C:34]([O:36][CH3:37])=[O:35].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:13]([CH3:20])[N:12]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:28])([F:30])[F:29])[CH:22]=3)[C:11](=[O:31])[N:10]2[CH2:33][C:34]([O:36][CH3:37])=[O:35])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 57651319HCID 57651319, compound

Product 1

HCID 58266274HCID 58266274, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

500 mg (1.164 mmol) of the compound from Example 5A were stirred together with 220 mg (1.397 mmol) of methyl bromoacetate and 322 mg (2.329 mmol) of potassium carbonate in 20 ml of DMF at 60° C. overnight. The solid was then filtered off, the filtrate was concentrated on a rotary evaporator, the residue was dissolved in dichloromethane and this solution was washed three times with water. The organic phase was separated off, dried over sodium sulphate, filtered and concentrated. The crude product was purified by chromatography on silica gel (mobile phase toluene/ethyl acetate 3:1). This gave 419 mg (72% of theory) of the desired product.

Workup

  1. filtrationThe solid was then filtered off
  2. concentrationthe filtrate was concentrated on a rotary evaporator
  3. dissolutionthe residue was dissolved in dichloromethane
  4. washthis solution was washed three times with water
  5. customThe organic phase was separated off
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by chromatography on silica gel (mobile phase toluene/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-c9a8de4e8df3469d8ba1abce6418c0f7
Source dataset
uspto-grants-2013_11
Patent number
US08580800B2

Reaction notes

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