Sodium Hydroxide → HCID 59865659, compound

HRID 2064501Notes

Reaction equation

HRID 2064501 reaction equation
[C:1]([C:5]1[N:9]([CH3:10])[N:8]([CH2:11][CH:12]2[CH2:14][CH2:13]2)/[C:7](=[N:15]/C(=O)C(F)(F)F)/[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([C:5]1[N:9]([CH3:10])[N:8]([CH2:11][CH:12]2[CH2:13][CH2:14]2)[C:7](=[NH:15])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178480296HCID 178480296, compound

Product 1

HCID 59865659HCID 59865659, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of Example 9E (8.7 g, 28.8 mmol) and 6 N NaOH aqueous (20 mL) in MeOH (100 mL) was stirred at 50° C. overnight, cooled to room temperature, and concentrated under reduced pressure. The residue was diluted with water and extracted with CH2Cl2 (3×100 mL). The combined organic extracts were washed with brine and concentrated to provide 5.3 g (89%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.37-0.44 (m, 2H), 0.47-0.54 (m, 2H), 1.07-1.20 (m, 1H), 1.29-1.36 (m, 9H), 3.78 (s, 3H), 4.10 (d, J=6.74 Hz, 2H), 5.60 (s, 1H), 7.19 (s, 1H); MS (+DCI) m/z 208 [M+H]+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was diluted with water
  3. extractionextracted with CH2Cl2 (3×100 mL)
  4. washThe combined organic extracts were washed with brine
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f0df307fa22b4e148a5fbcf068285ddb
Source dataset
uspto-grants-2012_10
Patent number
US08288428B2

Reaction notes

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