Hydrochloric Acid → HCID 117992279, compound

HRID 530982Notes

Reaction equation

[OH-].[Na+].CO.[CH:5]1([C:8]2[CH:13]=[C:12]([CH2:14][N:15]3[CH2:20][CH2:19][CH:18]([N:21]4[CH2:30][CH2:29][C:28]5[N:27]=[C:26]([CH3:31])[C:25]([C:32]([O:34]C)=[O:33])=[CH:24][C:23]=5[C:22]4=[O:36])[CH2:17][CH2:16]3)[CH:11]=[C:10]([O:37][CH2:38][CH3:39])[C:9]=2[C:40]2[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=2)[CH2:7][CH2:6]1.Cl>C(OCC)(=O)C.C1COCC1>[CH:5]1([C:8]2[CH:13]=[C:12]([CH2:14][N:15]3[CH2:20][CH2:19][CH:18]([N:21]4[CH2:30][CH2:29][C:28]5[N:27]=[C:26]([CH3:31])[C:25]([C:32]([OH:34])=[O:33])=[CH:24][C:23]=5[C:22]4=[O:36])[CH2:17][CH2:16]3)[CH:11]=[C:10]([O:37][CH2:38][CH3:39])[C:9]=2[C:40]2[CH:41]=[CH:42][C:43]([F:46])=[CH:44][CH:45]=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 6-(1-((2-cyclopropyl-6-ethoxy-4′-fluorobiphenyl-4-yl)methyl)piperidin-4-yl)-2-methyl-5-oxo-5,6,7,8-tetrahydro-1,6-naphthyridine-3-carboxylate (770 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 solvent was distilled off under reduced pressure. The deposited solid was collected by filtration and washed with diethyl ether. The obtained solid was recrystallized (DMSO/ethanol/hexane) to obtain the title compound (221 mg).

Workup

distillationthe solvent was distilled off under reduced pressure
filtrationThe deposited solid was collected by filtration
washwashed with diethyl ether
customThe obtained solid was recrystallized (DMSO/ethanol/hexane)

Sources & evidence

ORD record: ord-f02cba65213244f8a432f92fa64791a4
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353108B2

Reaction notes

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