Lithium hydroxide, monohydrate → HCID 58431368, compound

HRID 1617412Notes

Reaction equation

HRID 1617412 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]>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

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67390745HCID 67390745, compound

Product 1

HCID 58431368HCID 58431368, compound

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. Yield: 0.030 g (100%); LC-MS: 230.1 (M+H)+. 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).

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)
  6. customto afford product as a white solid

Sources & evidence

ORD record
ord-383b55eda5f04ace99a08d7e9c58e35c
Source dataset
uspto-grants-2014_07
Patent number
US08765734B2

Reaction notes

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