Hydrochloric Acid → HCID 86713678, compound

HRID 1430540Notes

Reaction equation

HRID 1430540 reaction equation
[Br:1][C:2]1[C:7]([C:8]2[C:9](=[O:22])[N:10]([CH2:20][CH3:21])[C:11]3[C:16]([CH:17]=2)=[CH:15][N:14]=[C:13]([NH:18][CH3:19])[CH:12]=3)=[CH:6][C:5]([NH:23][C:24]([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([CH2:33][N:34]3[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36][CH2:35]3)[CH:28]=2)=[O:25])=[C:4]([F:41])[CH:3]=1.[ClH:42]>CC#N>[ClH:42].[ClH:42].[Br:1][C:2]1[C:7]([C:8]2[C:9](=[O:22])[N:10]([CH2:20][CH3:21])[C:11]3[C:16]([CH:17]=2)=[CH:15][N:14]=[C:13]([NH:18][CH3:19])[CH:12]=3)=[CH:6][C:5]([NH:23][C:24]([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([CH2:33][N:34]3[CH2:35][CH2:36][N:37]([CH3:40])[CH2:38][CH2:39]3)[CH:28]=2)=[O:25])=[C:4]([F:41])[CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71584754HCID 71584754, compound

Product 1

HCID 86713678HCID 86713678, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 1-(4-bromo-5-(1-ethyl-7-(methylamino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluorophenyl)-3-(3-((4-methylpiperazin-1-yl)methyl)phenyl)urea (55 mg, 0.088 mmol) in MeCN (4 mL) was treated with 0.1N HCl (1.81 mL, 0.181 mmol), frozen and lyophilized to afford 1-(4-bromo-5-(1-ethyl-7-(methylamino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluorophenyl)-3-(3-((4-methylpiperazin-1-yl)methyl)phenyl)urea dihydrochloride (60 mg, 93% yield). MS (ESI) m/z: 622.2 [M+H]+.

Workup

  1. temperaturefrozen

Sources & evidence

ORD record
ord-27aca01661b4471c9cf4f9b9a2f5ae4a
Source dataset
uspto-grants-2015_01
Patent number
US08940756B2

Reaction notes

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