Hydrochloric Acid → HCID 86713681, compound

HRID 1430544Notes

Reaction equation

HRID 1430544 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-f71c1918835e445bb563b7a4f30e685a
Source dataset
uspto-grants-2015_01
Patent number
US08940756B2

Reaction notes

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