Hydrochloric Acid → HCID 117992091, compound

HRID 531059Notes

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]([CH2:31][CH2:32][CH3:33])[C:25]([C:34]([O:36]C)=[O:35])=[CH:24][C:23]=5[C:22]4=[O:38])[CH2:17][CH2:16]3)[CH:11]=[C:10]([O:39][CH2:40][CH3:41])[C:9]=2[C:42]2[CH:47]=[CH:46][C:45]([F:48])=[C:44]([F:49])[CH:43]=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]([CH2:31][CH2:32][CH3:33])[C:25]([C:34]([OH:36])=[O:35])=[CH:24][C:23]=5[C:22]4=[O:38])[CH2:17][CH2:16]3)[CH:11]=[C:10]([O:39][CH2:40][CH3:41])[C:9]=2[C:42]2[CH:47]=[CH:46][C:45]([F:48])=[C:44]([F:49])[CH:43]=2)[CH2:6][CH2:7]1

Participants

Conditions

Temperature: 60 °C

Procedure

A 2 M aqueous sodium hydroxide solution (1.50 mL) was added at room temperature to methanol (5 mL)-THF (5 mL) solution of methyl 6-(1-((2-cyclopropyl-6-ethoxy-3′,4′-difluorobiphenyl-4-yl)methyl)piperidin-4-yl)-5-oxo-2-propyl-5,6,7,8-tetrahydro-1,6-naphthyridine-3-carboxylate (580 mg), and the mixture was stirred at 60° C. for 30 minutes. 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 (487 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-baa46d095b1c47619228682cba8b3dc1
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353108B2

Reaction notes

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