Hydrochloric Acid → HCID 58431368, compound

HRID 1426324Notes

Reaction equation

HRID 1426324 reaction equation
O.[OH-].[Li+].[F:4][CH:5]([F:20])[C:6]1[CH:7]=[C:8]([CH:13]=[C:14]([CH2:16][N:17]([CH3:19])[CH3:18])[CH:15]=1)[C:9]([O:11]C)=[O:10].Cl>O.O1CCCC1>[F:4][CH:5]([F:20])[C:6]1[CH:7]=[C:8]([CH:13]=[C:14]([CH2:16][N:17]([CH3:18])[CH3:19])[CH:15]=1)[C:9]([OH:11])=[O:10]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 67390745HCID 67390745, compound

Product 1

HCID 58431368HCID 58431368, compoundYield 100.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide, monohydrate (65.2 mg, 1.55 mmol) in water (0.7 mL) was added to a solution of methyl 3-(difluoromethyl)-5-[(dimethylamino)methyl]benzoate (45 mg, 0.13 mmol, from Step C) in tetrahydrofuran (2 mL). Upon stirring for 3.5 hours, the mixture was treated with 1N HCl to adjust the pH to 7, then THF was removed by rotary evaporation. Acetonitrile was added to make a 1:1 ACN:water mixture, the mixture was filtered, and the filtrate was purified via preparative HPLC-MS (C18 eluting with a gradient of MeCN/H2O containing 0.15% NH4OH) to afford product as a white solid (0.030 g, 100%). 1H NMR (300 MHz, DMSO-d6): δ 7.95 (s, 2H), 7.50 (s, 1H), 7.05 (t, 1H), 3.44 (s, 2H), 2.15 (s, 6H); LCMS (M+H)+: 230.1.

Workup

  1. customTHF was removed by rotary evaporation
  2. additionAcetonitrile was added
  3. filtrationwater mixture, the mixture was filtered
  4. customthe filtrate was purified via preparative HPLC-MS (C18
  5. washeluting with a gradient of MeCN/H2O containing 0.15% NH4OH)

Sources & evidence

ORD record
ord-0cf4191434364f3499deac35cff117e9
Source dataset
uspto-grants-2015_01
Patent number
US08933085B2

Reaction notes

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