Dichloromethane → HCID 66659164, compound

HRID 2414913Notes

Reaction equation

HRID 2414913 reaction equation
C[CH:2]1[C@H:8]2[N:9]([CH3:10])[C@H:5]([CH2:6][CH2:7]2)[C:4](=[N:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:3]1.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28](Cl)=[O:29])=[CH:23][CH:22]=1.Cl[CH2:32]Cl>>[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28]([N:11]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([CH3:32])=[CH:17][CH:18]=2)[C:4]2[C@H:5]3[N:9]([CH3:10])[C@H:8]([CH2:7][CH2:6]3)[CH2:2][CH:3]=2)=[O:29])=[CH:23][CH:22]=1

Participants

4

Reactant 3

HCID 6344Dichloromethane2×HCID 27346884-Methoxyphenylacetyl chlorideHCID 68952808HCID 68952808, compound

Product 1

HCID 66659164HCID 66659164, compoundYield 18%

Procedure

47AKU-38 (242 mg, 1.0 mmol) was dissolved in 5 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 69 mg (18%) 47AKU-39. HCl-salt was prepared from 2M HCl/diethylether in dichloromethane/heptane. TLC (10% methanol in dichloromethane): Rf=0.4. HPLC-MS (Method A): M+=391.2 (UV/MS(%)=91/86).

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-41ada0d080fc498ba30bc40310b52c3d
Source dataset
uspto-grants-2004_11
Patent number
US06815458B2

Reaction notes

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