Hydrochloric Acid → HCID 86713677, compound

HRID 1257249Notes

Reaction equation

HRID 1257249 reaction equation
[Cl: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:1].[ClH:42].[Cl: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 715847301-(4-Chloro-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

Product 1

HCID 86713677HCID 86713677, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(4-chloro-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 in MeCN (4 mL) was treated with 0.1N HCl (1.77 mL, 0.177 mmol), frozen and lyophilized to afford 1-(4-chloro-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 (53 mg, 91% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.46 (s, 1H), 8.89 (s, 1H), 8.42 (s, 1H), 8.14 (d, J=8.6 Hz, 1H), 7.75 (s, 1H), 7.50 (m, 2H), 7.35-7.19 (m, 3H), 6.96 (s, 1H), 6.33 (s, 1H), 4.10 (q, J=7.0 Hz, 2H), 3.66-3.21 (m, 8H), 3.09-2.94 (br s, 2H), 2.86 (s, 3H), 2.68 (s, 3H), 1.16 (t, J=7.0 Hz, 3H); MS (ESI) m/z: 578.3 μM+H+.

Workup

  1. temperaturefrozen

Sources & evidence

ORD record
ord-cc2697e770014287926353ddefbd3512
Source dataset
uspto-grants-2013_06
Patent number
US08461179B1

Reaction notes

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