Hydrochloric Acid → 6-(1-((2-Cyclopropyl-5-ethoxy-2',4'-difluorobiphenyl-4-yl)methyl)piperidin-4-yl)-5-oxo-2-propyl-5,6,7,8-tetrahydro-1,6-naphthyridine-3-carboxylic acid

HRID 531149Notes

Reaction equation

[CH:1]1([C:4]2[CH:9]=[C:8]([CH2:10][N:11]3[CH2:16][CH2:15][CH:14]([N:17]4[CH2:26][CH2:25][C:24]5[N:23]=[C:22]([CH2:27][CH2:28][CH3:29])[C:21]([C:30]([O:32]CC)=[O:31])=[CH:20][C:19]=5[C:18]4=[O:35])[CH2:13][CH2:12]3)[C:7]([O:36][CH2:37][CH3:38])=[CH:6][C:5]=2[C:39]2[CH:44]=[CH:43][C:42]([F:45])=[CH:41][C:40]=2[F:46])[CH2:3][CH2:2]1.C(O)C.[OH-].[Na+].Cl>C1COCC1.O>[CH:1]1([C:4]2[CH:9]=[C:8]([CH2:10][N:11]3[CH2:16][CH2:15][CH:14]([N:17]4[CH2:26][CH2:25][C:24]5[N:23]=[C:22]([CH2:27][CH2:28][CH3:29])[C:21]([C:30]([OH:32])=[O:31])=[CH:20][C:19]=5[C:18]4=[O:35])[CH2:13][CH2:12]3)[C:7]([O:36][CH2:37][CH3:38])=[CH:6][C:5]=2[C:39]2[CH:44]=[CH:43][C:42]([F:45])=[CH:41][C:40]=2[F:46])[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of ethyl 6-(1-((2-cyclopropyl-5-ethoxy-2′,4′-difluorobiphenyl-4-yl)methyl)piperidin-4-yl)-5-oxo-2-propyl-5,6,7,8-tetrahydro-1,6-naphthyridine-3-carboxylate (13.2 g) in THF (33 mL)-ethanol (33 mL) was added 2M aqueous sodium hydroxide solution (31.2 mL). The mixture was stirred for 1 hour at 50° C. The mixture was cooled to room temperature. 2M hydrochloric acid (31.2 mL) was added to the reaction mixture. Then water (62.5 mL) was added to the reaction mixture. After cooled to 0° C., the precipitate was collected by filtration, washed with water, dried by airstream to give the title compound (12.4 g).

Workup

temperatureThe mixture was cooled to room temperature
temperatureAfter cooled to 0° C.
filtrationthe precipitate was collected by filtration
washwashed with water
customdried by airstream

Sources & evidence

ORD record: ord-96ef4dd1e8a741cfa71fa3f50857e420
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353108B2

Reaction notes

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