Hydrochloric Acid → 2-(3-{[6-Amino-5-(trifluoroacetyl)pyridin-2-yl]amino}piperidin-1-yl)-6-(2,4-dichlorophenyl)pyridine-3-carboxylic acid hydrochloride

HRID 1183010Notes

Reaction equation

HRID 1183010 reaction equation
Cl.[NH2:2][C:3]1[N:8]=[C:7]([NH:9][CH:10]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]3[C:21]([C:22]([O:24]C)=[O:23])=[CH:20][CH:19]=[C:18]([C:26]4[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=4[Cl:33])[N:17]=3)[CH2:11]2)[CH:6]=[CH:5][C:4]=1[C:34](=[O:39])[C:35]([F:38])([F:37])[F:36].O.[OH-].[Na+].Cl>COCCOC>[ClH:32].[NH2:2][C:3]1[N:8]=[C:7]([NH:9][CH:10]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]3[C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=[C:18]([C:26]4[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=4[Cl:33])[N:17]=3)[CH2:11]2)[CH:6]=[CH:5][C:4]=1[C:34](=[O:39])[C:35]([F:38])([F:37])[F:36]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 86656325HCID 86656325, compound

Product 1

HCID 866563262-(3-{[6-Amino-5-(trifluoroacetyl)pyridin-2-yl]amino}piperidin-1-yl)-6-(2,4-dichlorophenyl)pyridine-3-carboxylic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

220 mg (0.36 mmol) of methyl 2-(3-{[6-amino-5-(trifluoroacetyl)pyridin-2-yl]amino}piperidin-1-yl)-6-(2,4-dichlorophenyl)pyridine-3-carboxylate hydrochloride (Example 8) were dissolved in 10 ml of 1,2-dimethoxyethane, and 4.4 ml of water were added. Then 43 mg (1.1 mmol) of sodium hydroxide were added and the mixture was stirred at RT for 30 min. For workup, 35 ml of 2 N hydrochloric acid were added and the precipitate which formed was filtered off with suction. 180 mg (75% of theory) of the product were obtained in solid form.

Workup

  1. customthe precipitate which formed
  2. filtrationwas filtered off with suction
  3. custom180 mg (75% of theory) of the product were obtained in solid form

Sources & evidence

ORD record
ord-177458e0d7e949e399161b4291c244bb
Source dataset
uspto-grants-2014_03
Patent number
US08664246B2

Reaction notes

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