Hydrochloric Acid → 2-(5-Chloro-2-fluoro-phenyl)-4-(6'-piperazin-1-yl-[3,3']bipyridinyl-5-yl)-[1,8]naphthyridine hydrochloride

HRID 1914958Notes

Reaction equation

HRID 1914958 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:19]=[CH:18][C:17]([C:20]3[CH:21]=[N:22][CH:23]=[C:24]([C:26]4[C:35]5[C:30](=[N:31][CH:32]=[CH:33][CH:34]=5)[N:29]=[C:28]([C:36]5[CH:41]=[C:40]([Cl:42])[CH:39]=[CH:38][C:37]=5[F:43])[CH:27]=4)[CH:25]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[ClH:42].[Cl:42][C:40]1[CH:39]=[CH:38][C:37]([F:43])=[C:36]([C:28]2[CH:27]=[C:26]([C:24]3[CH:25]=[C:20]([C:17]4[CH:18]=[N:19][C:14]([N:11]5[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]5)=[CH:15][CH:16]=4)[CH:21]=[N:22][CH:23]=3)[C:35]3[C:30](=[N:31][CH:32]=[CH:33][CH:34]=3)[N:29]=2)[CH:41]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 673648404-{5'-[2-(5-Chloro-2-fluoro-phenyl)-[1,8]naphthyridin-4-yl]-[3,3']bipyridinyl-6-yl}-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 673652172-(5-Chloro-2-fluoro-phenyl)-4-(6'-piperazin-1-yl-[3,3']bipyridinyl-5-yl)-[1,8]naphthyridine hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 438 mg (0.734 mmol) 4-{5′-[2-(5-Chloro-2-fluoro-phenyl)-[1,8]naphthyridin-4-yl]-[3,3′]bipyridinyl-6-yl}-piperazine-1-carboxylic acid tert-butyl ester in 5 ml dioxane was treated with 6 ml of a 4 N solution of hydrochlorid acid in dioxane. The mixture was stirred for 20 minutes at room temperature. The resulting precipitate was filtered off, washed with dioxane and dried under vacuum yielding 2-(5-chloro-2-fluoro-phenyl)-4-(6′-piperazin-1-yl-[3,3′]bipyridinyl-5-yl)-[1,8]naphthyridine hydrochloride as light yellow solid; HPLC-MS: 1.66 min, [M+H] 497.

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. washwashed with dioxane
  3. customdried under vacuum

Sources & evidence

ORD record
ord-d9dc4faa29414d67bb554e0ea9d787c2
Source dataset
uspto-grants-2013_12
Patent number
US08614226B2

Reaction notes

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