Hydrochloric Acid → HCID 86713675, compound

HRID 1257247Notes

Reaction equation

HRID 1257247 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[C:9](=[O:23])[N:10]([CH:20]([CH3:22])[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:24][C:25]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=2)=[O:26])=[C:4]([F:35])[CH:3]=1.Cl>CC#N>[ClH:1].[Cl:1][C:2]1[C:7]([C:8]2[C:9](=[O:23])[N:10]([CH:20]([CH3:22])[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:24][C:25]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=2)=[O:26])=[C:4]([F:35])[CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71584728HCID 71584728, compound

Product 1

HCID 86713675HCID 86713675, compoundYield 169.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(4-chloro-2-fluoro-5-(1-isopropyl-7-(methylamino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)phenyl)-3-(3-fluorophenyl)urea (22 mg, 0.042 mmol) in MeCN (1.5 mL) was treated with 0.1N HCl (464 μL, 0.046 mmol), frozen and lyophilized to afford 1-(4-chloro-2-fluoro-5-(1-isopropyl-7-(methylamino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)phenyl)-3-(3-fluorophenyl)urea hydrochloride (19 mg, 84% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.58 (s, 1H), 8.90 (s, 1H), 8.50 (s, 1H), 8.18 (d, J=8.6 Hz, 1H), 7.83 (s, 1H), 7.56 (d, J=10.9 Hz, 1H), 7.50-7.38 (m, 2H), 7.32-7.25 (m, 1H), 7.07 (dd, J=8.2, 1.9 Hz, 1H), 6.82-6.73 (m, 2H), 5.12 (m, 1H), 2.96 (s, 3H), 1.52 (d, J=6.9 Hz, 6H); MS (ESI) m/z: 498.2 [M+H]+.

Workup

  1. temperaturefrozen

Sources & evidence

ORD record
ord-f6e92cc9f7e44d9299ee48b199e704ab
Source dataset
uspto-grants-2013_06
Patent number
US08461179B1

Reaction notes

Loading…