Hydrochloric Acid → HCID 86713681, compound

HRID 1257254Notes

Reaction equation

HRID 1257254 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([NH:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:11])=[CH:4][C:3]=1[C:19]1[C:20](=[O:36])[N:21]([CH:33]([CH3:35])[CH3:34])[C:22]2[C:27]([CH:28]=1)=[CH:26][N:25]=[C:24]([NH:29][C:30](=[O:32])[CH3:31])[CH:23]=2.Cl.CCOCC>CC#N>[ClH:1].[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([NH:9][C:10]([NH:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:11])=[CH:4][C:3]=1[C:19]1[C:20](=[O:36])[N:21]([CH:33]([CH3:34])[CH3:35])[C:22]2[C:27]([CH:28]=1)=[CH:26][N:25]=[C:24]([NH:29][C:30](=[O:32])[CH3:31])[CH:23]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 71584757HCID 71584757, compound

Product 1

HCID 86713681HCID 86713681, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of N-(3-(2-chloro-4-fluoro-5-(3-phenylureido)phenyl)-1-isopropyl-2-oxo-1,2-dihydro-1,6-naphthyridin-7-yl)acetamide (33 mg, 0.065 mmol) in MeCN (3 mL) was treated with 0.1N HCl (0.650 mL, 0.065 mmol), frozen and lyophilized. The material was treated with Et2O, the solid collected via filtration and dried to afford N-(3-(2-chloro-4-fluoro-5-(3-phenylureido)phenyl)-1-isopropyl-2-oxo-1,2-dihydro-1,6-naphthyridin-7-yl)acetamide hydrochloride (17 mg, 47% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.82 (s, 1H), 9.16 (s, 1H), 8.75 (s, 1H), 8.69 (s, 1H), 8.53 (s, 1H), 8.22 (d, J=8.6 Hz, 1H), 7.93 (s, 1H), 7.56 (d, J=11.0 Hz, 1H), 7.42 (d, J=8.0 Hz, 2H), 7.26 (t, J=7.7 Hz, 2H), 6.97 (t, J=7.3 Hz, 1H), 3.71 (m, 1H), 2.15 (s, 3H), 1.56 (d, J=7.0 Hz, 6H); MS (ESI) m/z: 508.2 [M+H]+.

Workup

  1. temperaturefrozen
  2. filtrationthe solid collected via filtration
  3. customdried

Sources & evidence

ORD record
ord-cbd95f70bde04551bb52f11f942d9e93
Source dataset
uspto-grants-2013_06
Patent number
US08461179B1

Reaction notes

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