Hydrochloric Acid → HCID 66614124, compound

HRID 510111Notes

Reaction equation

HRID 510111 reaction equation
[NH2:1][C:2]1[C:7]([N:8]([C:14]([O:16][CH3:17])=[O:15])[CH2:9][C:10](OC)=[O:11])=[C:6]([NH2:18])[N:5]=[C:4]([C:19]2[C:27]3[C:22](=[N:23][CH:24]=[CH:25][CH:26]=3)[N:21]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[F:35])[N:20]=2)[N:3]=1.[OH-].[Li+].Cl>C(O)C.O>[NH2:18][C:6]1[C:7]2[N:8]([C:14]([O:16][CH3:17])=[O:15])[CH2:9][C:10](=[O:11])[NH:1][C:2]=2[N:3]=[C:4]([C:19]2[C:27]3[C:22](=[N:23][CH:24]=[CH:25][CH:26]=3)[N:21]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[F:35])[N:20]=2)[N:5]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66614141HCID 66614141, compound

Product 1

HCID 66614124HCID 66614124, compoundYield 1.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

3.5 g (7.285 mmol) of the crude compound from example 55A were dissolved in ethanol (25 ml) and water (25 ml), and 174 mg (7.285 mmol) of lithium hydroxide were added. After stirring at RT for 30 min, the mixture was adjusted to pH=6 with dilute hydrochloric acid and extracted with ethyl acetate. After separation of the phases, the organic phase was washed with saturated aqueous sodium chloride solution and then dried with sodium sulfate, filtered and concentrated to dryness. The residue was slurried in acetonitrile and ethyl acetate, and insoluble constituents were filtered off. The filtrate was concentrated and the residue was purified by means of preparative HPLC (acetonitrile:water (+0.05% formic acid) gradient). 38 mg of the title compound were obtained (1% of theory).

Workup

  1. extractionextracted with ethyl acetate
  2. customAfter separation of the phases
  3. washthe organic phase was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. filtrationethyl acetate, and insoluble constituents were filtered off
  8. concentrationThe filtrate was concentrated
  9. customthe residue was purified by means of preparative HPLC (acetonitrile:water (+0.05% formic acid) gradient)

Sources & evidence

ORD record
ord-dbf21d7a46764913a54d67b14334e800
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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