Hydrochloric Acid → HCID 59000908, compound

HRID 529172Notes

Reaction equation

HRID 529172 reaction equation
[CH2:1]([N:8]([CH2:10][C:11]1[C:19]2[C:18](=[O:20])[N:17]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[C:16](=[O:27])[N:15]([CH2:28][C:29]3[C:34]([F:35])=[CH:33][CH:32]=[CH:31][C:30]=3[F:36])[C:14]=2[S:13][C:12]=1[C:37]1[CH:42]=[CH:41][C:40]([NH:43][C:44]([NH:46][O:47][CH3:48])=[O:45])=[CH:39][CH:38]=1)C)C1C=CC=CC=1.Cl>C(O)C.[C].[Pd]>[F:36][C:30]1[CH:31]=[CH:32][CH:33]=[C:34]([F:35])[C:29]=1[CH2:28][N:15]1[C:14]2[S:13][C:12]([C:37]3[CH:42]=[CH:41][C:40]([NH:43][C:44]([NH:46][O:47][CH3:48])=[O:45])=[CH:39][CH:38]=3)=[C:11]([CH2:10][NH:8][CH3:1])[C:19]=2[C:18](=[O:20])[N:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[C:16]1=[O:27]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59000860HCID 59000860, compound

Product 1

HCID 59000908HCID 59000908, compoundYield 71.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of the compound obtained in Example 1 (1.59 g, 2.38 mmol) in ethanol (40 ml) were added 1N hydrochloric acid (7 ml) and 10% palladium-carbon (50% wet, 0.63 g), and the mixture was stirred vigorously under hydrogen atmosphere for 20 hours. The catalyst was removed, and the filtrate was neutralized with 1N sodium hydroxide solution. The solvent was distilled off. The residue was distributed between ethyl acetate and water, and the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the obtained powders were washed with diethyl ether to give the title compound (980 mg, 71%) as pale yellow powders.

Workup

  1. customThe catalyst was removed
  2. distillationThe solvent was distilled off
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off
  6. washthe obtained powders were washed with diethyl ether

Sources & evidence

ORD record
ord-aa4206ab2402434aa59a7176591df935
Source dataset
uspto-grants-2016_05
Patent number
US09346822B2

Reaction notes

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