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

HRID 1914959Notes

Reaction equation

Cl.[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([F:37])=[C:7]([C:9]2[CH:18]=[C:17]([C:19]3[CH:20]=[C:21]([C:25]4[CH:26]=[N:27][C:28]([N:31]5[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]5)=[CH:29][CH:30]=4)[CH:22]=[N:23][CH:24]=3)[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10]=2)[CH:8]=1.[CH2:38]=O.[OH-].[Na+]>C(O)=O>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([F:37])=[C:7]([C:9]2[CH:18]=[C:17]([C:19]3[CH:20]=[C:21]([C:25]4[CH:26]=[N:27][C:28]([N:31]5[CH2:36][CH2:35][N:34]([CH3:38])[CH2:33][CH2:32]5)=[CH:29][CH:30]=4)[CH:22]=[N:23][CH:24]=3)[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10]=2)[CH:8]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 180 mg (0.34 mmol) 2-(5-chloro-2-fluoro-phenyl)-4-(6′-piperazin-1-yl-[3,3′]bipyridinyl-5-yl)-[1,8]naphthyridine hydrochloride in 1.5 ml formic acid was treated with 80 μl (1.01 mmol) 35% aqueous formaldehyde solution and heated to 80° C. The reaction mixture was stirred at this temperature for 2 hours. The volume of the reaction mixture was reduced under vacuum and the residue made strongly alkaline with 2 N NaOH. The resulting precipitate was filtered off, washed with water and dried yielding 2-(5-chloro-2-fluoro-phenyl)-4-[6′-(4-methyl-piperazin-1-yl)-[3,3′]bipyridinyl-5-yl]-[1,8]naphthyridine as gray-green solid; HPLC-MS: 1.55 min, [M+H] 511.

Workup

filtrationThe resulting precipitate was filtered off
washwashed with water
customdried

Sources & evidence

ORD record: ord-b3736402ca324b65bed914762dc0c334
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08614226B2

Reaction notes

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