HCID 9918695, compound → HCID 178450365, compound

HRID 727246Notes

Reaction equation

HRID 727246 reaction equation
[CH2:1]([O:5][C:6]1[N:11]=[C:10]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]3[N:27]=[N:28][N:29](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:30]=3)=[CH:16][CH:15]=2)=[O:13])[C:9]([C:50]([O:52][CH2:53][CH3:54])=[O:51])=[CH:8][C:7]=1[C:55]([O:57][CH2:58][CH3:59])=[O:56])[CH2:2][CH2:3][CH3:4]>Cl.CO.O>[CH2:1]([O:5][C:6]1[N:11]=[C:10]([C:12]([C:14]2[CH:15]=[CH:16][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]3[NH:30][N:29]=[N:28][N:27]=3)=[CH:18][CH:19]=2)=[O:13])[C:9]([C:50]([O:52][CH2:53][CH3:54])=[O:51])=[CH:8][C:7]=1[C:55]([O:57][CH2:58][CH3:59])=[O:56])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 1

HCID 9918695HCID 9918695, compound

Product 1

HCID 178450365HCID 178450365, compoundYield 84.6%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

One drop of concentrated hydrochloric acid is added to a solution of 30 mg (0.04 mmol) of the compound from Example 1 in 2 ml of methanol and the mixture is stirred at 20° C. for 3 hours. The reaction mixture is diluted with water and washed three times with ethyl acetate, the combined organic phases are washed with water and sodium chloride solution, dried over sodium sulphate and concentrated and the residue is chromatographed over 25 g of silica gel using methylene chloride/methanol 10:1 to give 15.9 mg of the title compound.

Workup

  1. washwashed three times with ethyl acetate
  2. washthe combined organic phases are washed with water and sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated
  5. customthe residue is chromatographed over 25 g of silica gel

Sources & evidence

ORD record
ord-7c1c049ccf604d759afdc1c72bf269f9
Source dataset
uspto-grants-1998_01
Patent number
US05712296

Reaction notes

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