Hydrochloric Acid → HCID 58011843, compound

HRID 660879Notes

Reaction equation

HRID 660879 reaction equation
[Br:1][C:2]1[N:3]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[F:15])[C:4](=[O:7])[NH:5][N:6]=1.Cl[CH2:17][C:18]([O:20][CH3:21])=[O:19].C(=O)([O-])[O-].[K+].[K+].Cl>C(#N)C.C(OCC)(=O)C>[CH3:21][O:20][C:18](=[O:19])[CH2:17][N:5]1[C:4](=[O:7])[N:3]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[F:15])[C:2]([Br:1])=[N:6]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7295Methyl chloroacetateHCID 11430Potassium CarbonateHCID 57455737HCID 57455737, compound

Product 1

HCID 58011843HCID 58011843, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

300 mg (1.1 mmol) of the compound from Example 135A are stirred under reflux for 2 hrs together with 150 mg (1.38 mmol) of methyl chloroacetate and 168 mg (1.21 mmol) of potassium carbonate in 10 ml acetonitrile. After cooling, the mixture is diluted with ethyl acetate and treated with 1 N hydrochloric acid. The organic phase is separated, washed with saturated sodium chloride solution, dried over sodium sulphate and freed of the volatile components on the rotary evaporator. The residue is dried under high vacuum. The product thus obtained (360 mg, purity ca. 73% by LC/MS) is used in the next synthetic step without further purification.

Workup

  1. temperatureAfter cooling
  2. customThe organic phase is separated
  3. washwashed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. customfreed of the volatile components on the rotary evaporator
  6. customThe residue is dried under high vacuum
  7. customThe product thus obtained (360 mg, purity ca. 73% by LC/MS)
  8. customis used in the next synthetic step without further purification

Sources & evidence

ORD record
ord-7c1f7d52aaee46559425e662cc2c087a
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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