HCID 18958728, compound → HCID 178441529, compound

HRID 1708436Notes

Reaction equation

HRID 1708436 reaction equation
[CH2:1]([C:5]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]3[N:28](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:27]=[N:26][N:25]=3)=[CH:14][CH:13]=2)[C:9](=[O:48])[N:8]2[N:49]=[CH:50][CH:51]=[C:7]2[N:6]=1)[CH2:2][CH2:3][CH3:4]>CC(C)=O.O.CO.Cl>[CH2:1]([C:5]1[N:10]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]3[NH:28][N:27]=[N:26][N:25]=3)=[CH:16][CH:17]=2)[C:9](=[O:48])[N:8]2[N:49]=[CH:50][CH:51]=[C:7]2[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 1

HCID 18958728HCID 18958728, compound

Product 1

HCID 178441529HCID 178441529, compoundYield 67.2%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolventHCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

A solution of 700 mg of the product of Example 16 in 200 ml of 9:1 acetone-water, 50 ml of methyl alcohol and 2 drops of 5% HCl is refluxed for 16 hours. The reaction mixture is concentrated in vacuo to a residue which is extracted with 3:1 chloroform-methanol. The chloroform layer is dried with anhydrous Na2SO4, filtered and concentrated to a residue which is purified by column chromatography on silica gel by elution with 90% ethyl acetate-hexanes to give 300 mg of the desired product as a solid. M+H=426.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo to a residue which
  2. extractionis extracted with 3:1 chloroform-methanol
  3. dry with materialThe chloroform layer is dried with anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to a residue which
  6. customis purified by column chromatography on silica gel by elution with 90% ethyl acetate-hexanes

Sources & evidence

ORD record
ord-2d7157e4edae445b9e08fe4453f9ed8e
Source dataset
uspto-grants-1994_10
Patent number
US05358947

Reaction notes

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