Hydrochloric Acid → HCID 66915720, compound

HRID 2356969Notes

Reaction equation

HRID 2356969 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([N:24]4[C:28](=[O:29])[C:27]([CH3:31])([CH3:30])[N:26]([CH2:32][C:33]5[C:42]6[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=6)[N:36]=[CH:35][CH:34]=5)[C:25]4=[O:43])[CH:22]=3)[C:17]([CH3:45])([CH3:44])[CH2:16]2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>CO>[CH3:44][C:17]1([CH3:45])[C:18]2[C:23](=[CH:22][C:21]([N:24]3[C:28](=[O:29])[C:27]([CH3:30])([CH3:31])[N:26]([CH2:32][C:33]4[C:42]5[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=5)[N:36]=[CH:35][CH:34]=4)[C:25]3=[O:43])=[CH:20][CH:19]=2)[N:15]([CH2:14][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH2:16]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66915902HCID 66915902, compound

Product 1

HCID 66915720HCID 66915720, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 25 mg 4-[6-(4,4-dimethyl-2,5-dioxo-3-quinolin-4-ylmethyl-imidazolidin-1-yl)-3,3-dimethyl-2,3-dihydro-indol-1-ylmethyl]-piperidine-1-carboxylic acid tert-butyl ester in 2 ml of a 8 N solution of hydrochloric acid in methanol was stirred for 1 hour at room temperature. After removal of the solvent under reduced pressure the residue was purified by preparative HPLC (C18 reverse phase column, elution with a water/acetonitrile gradient with 0.1% trifluoroacetic acid). Lyophilization of the combined fractions containing the product yielded a white solid, that was partitioned between 2 ml of a satured aqueous solution of sodium hydrogen carbonate and 2 ml ethyl acetate. The organic layer was dried over sodium sulfate. After filtration the solvent was removed under reduced pressure. The residue was dissolved in a mixture of 1 ml acetonitrile and 2 ml water. After addition of 0.01 ml of a 1 N solution of hydrochloric acid the resulting solution was lyophilized to yield a white foam. The product was obtained as its hydrochloric salt.

Workup

  1. customAfter removal of the solvent under reduced pressure the residue
  2. customwas purified by preparative HPLC (
  3. washC18 reverse phase column, elution with a water/acetonitrile gradient with 0.1% trifluoroacetic acid)
  4. additionLyophilization of the combined fractions containing the product
  5. customyielded a white solid, that
  6. customwas partitioned between 2 ml of a satured aqueous solution of sodium hydrogen carbonate and 2 ml ethyl acetate
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. filtrationAfter filtration the solvent
  9. customwas removed under reduced pressure
  10. dissolutionThe residue was dissolved in a mixture of 1 ml acetonitrile and 2 ml water
  11. additionAfter addition of 0.01 ml of a 1 N solution of hydrochloric acid the resulting solution
  12. customto yield a white foam
  13. customThe product was obtained as its hydrochloric salt

Sources & evidence

ORD record
ord-71a70fa165454ed0abd57a131ca1abd5
Source dataset
uspto-grants-2010_07
Patent number
US07759379B2

Reaction notes

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