Hydrochloric Acid → HCID 178474531, compound

HRID 554647Notes

Reaction equation

HRID 554647 reaction equation
C1CCCCC=1.O1CCCC1.B.[CH2:13]([N:20]([CH2:24][C:25]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:26]=1[C:35]1[C:36]([O:43]C)=[N:37][CH:38]=[C:39]([C:41]#[CH:42])[CH:40]=1)[C:21](=[O:23])[CH3:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH-:45].[Na+].[OH:47]O.Cl>C1COCC1.CO>[C:21]([N:20]([CH2:24][C:25]1[CH:30]=[C:29]([C:31]([F:32])([F:33])[F:34])[CH:28]=[CH:27][C:26]=1[C:35]1[CH:40]=[C:39]([CH2:41][C:42]([OH:47])=[O:45])[CH:38]=[N:37][C:36]=1[OH:43])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:23])[CH3:22]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 8079CyclohexeneHCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 86640542N-Benzyl-N-[2-(5-ethynyl-2-methoxy-pyridin-3-yl)-5-trifluoromethyl-benzyl]-acetamide

Product 1

HCID 178474531HCID 178474531, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To cyclohexene (0.20 mL, 1.98 mmol) at room temperature was added borane tetrahydrofuran complex (1M in THF; 1.01 mL, 1.01 mmol), and the reaction was stirred for 45 minutes. N-Benzyl-N-[2-(5-ethynyl-2-methoxy-pyridin-3-yl)-5-trifluoromethyl-benzyl]-acetamide (0.126 g, 0.29 mmol) in THF (2 mL) was added dropwise, and the reaction was stirred for 2 hours at room temperature. The mixture was cooled to 0° C., and MeOH (1 mL) and 1N aqueous NaOH (1.01 mL, 1.01 mmol) were added, followed by hydrogen peroxide (30%; 0.31 mL, 3.00 mmol), and the reaction was stirred for 1 hour at 0° C. The mixture was acidified with 1N aqueous HCl and extracted with EtOAc, and the combined organic layers were dried, filtered, and concentrated. The residue was purified by preparative HPLC to give (5-{2-[(N-Acetyl-N-benzyl-amino)-methyl]-4-trifluoromethyl-phenyl}-6-hydroxy-pyridin-3-yl)-acetic acid.

Workup

  1. stirringthe reaction was stirred for 2 hours at room temperature
  2. stirringthe reaction was stirred for 1 hour at 0° C
  3. extractionextracted with EtOAc
  4. customthe combined organic layers were dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-b64b1b78bde446c1a970ae2f4fd9107a
Source dataset
uspto-grants-2011_11
Patent number
US08049015B2

Reaction notes

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