Hydrochloric Acid → 1-(1-((6-Cyclopropyl-2,4'-difluoro-3-isopropoxybiphenyl-4-yl)methyl)piperidin-4-yl)-3-methyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid hydrochloride

HRID 2272540Notes

Reaction equation

HRID 2272540 reaction equation
[CH:1]1([C:4]2[C:9]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)=[C:8]([F:17])[C:7]([O:18][CH:19]([CH3:21])[CH3:20])=[C:6]([CH2:22][N:23]3[CH2:28][CH2:27][CH:26]([N:29]4[CH:34]=[CH:33][C:32]([C:35]([OH:37])=[O:36])=[C:31]([CH3:38])[C:30]4=[O:39])[CH2:25][CH2:24]3)[CH:5]=2)[CH2:3][CH2:2]1.[ClH:40].C(OC(C)C)(C)C>C(O)(C)C>[ClH:40].[CH:1]1([C:4]2[C:9]([C:10]3[CH:11]=[CH:12][C:13]([F:16])=[CH:14][CH:15]=3)=[C:8]([F:17])[C:7]([O:18][CH:19]([CH3:21])[CH3:20])=[C:6]([CH2:22][N:23]3[CH2:24][CH2:25][CH:26]([N:29]4[CH:34]=[CH:33][C:32]([C:35]([OH:37])=[O:36])=[C:31]([CH3:38])[C:30]4=[O:39])[CH2:27][CH2:28]3)[CH:5]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7914Diisopropyl EtherHCID 917546701-(1-((6-Cyclopropyl-2,4'-difluoro-3-isopropoxybiphenyl-4-yl)methyl)piperidin-4-yl)-3-methyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid

Product 1

HCID 1180374431-(1-((6-Cyclopropyl-2,4'-difluoro-3-isopropoxybiphenyl-4-yl)methyl)piperidin-4-yl)-3-methyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

1-(1-((6-Cyclopropyl-2,4′-difluoro-3-isopropoxybiphenyl-4-yl)methyl)piperidin-4-yl)-3-methyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid (15.0 g) was dissolved in isopropanol (150 mL) at 60 C. The mixture was cooled to room temperature. 2M hydrogen chloride (isopropanol solution, 21.0 mL) was added to the mixture at room temperature. After being stirred at room temperature for 30 minutes, diisopropyl ether (300 mL) and crystalline seeds were added to the mixture. The mixture was stirred for 1 hour under nitrogen atmosphere. The precipitate was collected by filtration, washed with diisopropyl ether (150 mL) and heptane (100 mL), and then dried at 60 C to give the title compound (14.3 g).

Workup

  1. stirringThe mixture was stirred for 1 hour under nitrogen atmosphere
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with diisopropyl ether (150 mL) and heptane (100 mL)
  4. customdried at 60 C

Sources & evidence

ORD record
ord-6991ff720ee84373bd8f0f6f93e6bfdd
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

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