4-Methoxyphenylacetyl chloride → HCID 23512960, compound

HRID 2414911Notes

Reaction equation

HRID 2414911 reaction equation
[CH3:1][CH:2]([NH:9][CH:10]1[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][C:26](Cl)=[O:27])=[CH:21][CH:20]=1>ClCCl>[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][C:26]([N:9]([CH:2]([CH3:1])[C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)=[O:27])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 27346884-Methoxyphenylacetyl chlorideHCID 3153429HCID 3153429, compound

Product 1

HCID 23512960HCID 23512960, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

47AKU-36 (218 mg, 1.0 mmol) was dissolved in 10 ml dichloromethane and placed in 50 ml flask. 4-Methoxyphenylacetyl chloride (185 mg, 1.2 mmol) in 10 ml dichloromethane was added. After 16 hrs magnetic stirring the reaction mixture was concentrated on Rotavapor (40° C.). Crude product was purified by flash chromatography (0-10% methanol in dichloromethane) giving 256 mg (70%) 47AKU-37. HCl-salt was prepared from 2M HCl/diethylether in dichloromethane/heptane. TLC (10% methanol in dichloromethane): Rf=0.5. HPLC-MS (Method A): M+=367.3 (UV/MS(%)=100/99).

Workup

  1. customplaced in 50 ml flask
  2. concentrationwas concentrated on Rotavapor (40° C.)
  3. customCrude product was purified by flash chromatography (0-10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-9dc05c89b3cb4d2dbf2efb671ee642b7
Source dataset
uspto-grants-2004_11
Patent number
US06815458B2

Reaction notes

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