Hydrochloric Acid → HCID 86640853, compound

HRID 1913193Notes

Reaction equation

HRID 1913193 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](/[C:8](=[CH:14]/[N:15](C)C)/[C:9]([O:11]CC)=O)[CH:5]=[N:6][CH:7]=1.[NH:18]([C:20]1[N:25]=[CH:24][C:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[CH:22][CH:21]=1)N.C1(C)C=CC(S(O)(=O)=O)=CC=1.[ClH:44]>C(O)C.O1CCOCC1>[ClH:44].[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9](=[O:11])[N:18]([C:20]3[N:25]=[CH:24][C:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[CH:22][CH:21]=3)[NH:15][CH:14]=2)[CH:5]=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 45089857Tert-butyl 6-hydrazinylpyridine-3-carboxylateHCID 59186962HCID 59186962, compound

Product 1

HCID 86640853HCID 86640853, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

500 mg (1.7 mmol) of the compound from Example 9A and 350 mg (1.7 mmol) of the compound from Example 15A are dissolved in 2 ml of ethanol, and 58 mg (0.3 mmol) of p-toluenesulfonic acid are added. The mixture is heated under reflux for 24 h and then cooled to RT, and 0.5 ml of a 4 N solution of hydrogen chloride in dioxane is added. The mixture is stirred at RT for 30 min. The precipitate is filtered off, washed with ethanol and diethyl ether and dried under high vacuum.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 24 h
  3. filtrationThe precipitate is filtered off
  4. washwashed with ethanol and diethyl ether
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-9f549ee497b245979354475d077235bd
Source dataset
uspto-grants-2013_12
Patent number
US08609698B2

Reaction notes

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