Hydrochloric Acid → HCID 117992183, compound

HRID 530990Notes

Reaction equation

[OH-].[Na+].CO.[CH:5]1([C:8]2[C:17]([C:18]([O:20]C)=[O:19])=[CH:16][C:15]3[C:14](=[O:22])[N:13]([CH:23]4[CH2:28][CH2:27][N:26]([CH2:29][C:30]5[C:35]([O:36][CH2:37][CH3:38])=[CH:34][C:33]([C:39]6[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=6)=[C:32]([CH:46]6[CH2:48][CH2:47]6)[CH:31]=5)[CH2:25][CH2:24]4)[CH2:12][CH2:11][C:10]=3[N:9]=2)[CH2:7][CH2:6]1.Cl>C(OCC)(=O)C.C1COCC1>[CH:5]1([C:8]2[C:17]([C:18]([OH:20])=[O:19])=[CH:16][C:15]3[C:14](=[O:22])[N:13]([CH:23]4[CH2:24][CH2:25][N:26]([CH2:29][C:30]5[C:35]([O:36][CH2:37][CH3:38])=[CH:34][C:33]([C:39]6[CH:40]=[CH:41][C:42]([F:45])=[CH:43][CH:44]=6)=[C:32]([CH:46]6[CH2:47][CH2:48]6)[CH:31]=5)[CH2:27][CH2:28]4)[CH2:12][CH2:11][C:10]=3[N:9]=2)[CH2:6][CH2:7]1

Participants

Conditions

Temperature: 50 °C

Procedure

A 2 M aqueous sodium hydroxide solution (1.50 mL) was added at room temperature to a methanol (2 mL)-THF (2 mL) solution of methyl 2-cyclopropyl-6-(1-((2-cyclopropyl-5-ethoxy-4′-fluorobiphenyl-4-yl)methyl)piperidin-4-yl)-5-oxo-5,6,7,8-tetrahydro-1,6-naphthyridine-3-carboxylate (480 mg), and the mixture was stirred at 50° C. for 1 hour. The reaction mixture was neutralized with hydrochloric acid at room temperature. Then, ethyl acetate was added thereto, and the mixture was concentrated. The deposited solid was collected by filtration and washed with diethyl ether. The obtained solid was recrystallized (ethanol/hexane) to obtain the title compound (320 mg).

Workup

concentrationthe mixture was concentrated
filtrationThe deposited solid was collected by filtration
washwashed with diethyl ether
customThe obtained solid was recrystallized (ethanol/hexane)

Sources & evidence

ORD record: ord-607a665c5e114e82ba29b4102a882d08
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353108B2

Reaction notes

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