HCID 67363289, compound → 2-(5-chloro-2-fluoro-phenyl)-4-[5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-3-yl]-[1,8]naphthyridine dihydrochloride

HRID 1914944Notes

Reaction equation

HRID 1914944 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH:18]=[C:17]([C:19]3[CH:20]=[N:21][CH:22]=[C:23]([C:25]4[C:34]5[C:29](=[N:30][CH:31]=[CH:32][CH:33]=5)[N:28]=[C:27]([C:35]5[CH:40]=[C:39]([Cl:41])[CH:38]=[CH:37][C:36]=5[F:42])[CH:26]=4)[CH:24]=3)[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=O)(C)(C)C>Cl.O1CCOCC1.CO>[ClH:41].[ClH:41].[Cl:41][C:39]1[CH:38]=[CH:37][C:36]([F:42])=[C:35]([C:27]2[CH:26]=[C:25]([C:23]3[CH:22]=[N:21][CH:20]=[C:19]([C:17]4[CH:16]=[N:15][N:14]([CH:11]5[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]5)[CH:18]=4)[CH:24]=3)[C:34]3[C:29](=[N:30][CH:31]=[CH:32][CH:33]=3)[N:28]=2)[CH:40]=1

Participants

5

Reactant 1

HCID 67363289HCID 67363289, compound

Product 1

HCID 533280612-(5-chloro-2-fluoro-phenyl)-4-[5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-3-yl]-[1,8]naphthyridine dihydrochloride

Reagents, catalysts & solvents 3

HCID 887MethanolCatalystHCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A slurry of 155 mg (0.265 mmol) 4-(4-{5-[2-(5-chloro-2-fluoro-phenyl)-[1,8]naphthyridin-4-yl]-pyridin-3-yl}-pyrazol-1-yl)-piperidine-1-carboxylic acid tert-butyl-ester in 1.5 ml 4 N HCl in dioxane was treated with 1 drop of methanol. The solution thus formed was left for 3 hours at room temperature and subsequently evaporated. The residue was treated with tert-butyl-methyl-ether and the solid was filtered off. The residue was dissolved in water and lyophilized yielding 2-(5-chloro-2-fluoro-phenyl)-4-[5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-3-yl]-[1,8]naphthyridine dihydrochloride als colourless lyophilisate; HPLC-MS: 1.65 min, [M+H] 485.

Workup

  1. customThe solution thus formed
  2. customsubsequently evaporated
  3. additionThe residue was treated with tert-butyl-methyl-ether
  4. filtrationthe solid was filtered off
  5. dissolutionThe residue was dissolved in water

Sources & evidence

ORD record
ord-41a54855bb234d8e97299e4d5a34694f
Source dataset
uspto-grants-2013_12
Patent number
US08614226B2

Reaction notes

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