Sodium Hydroxide → HCID 68556947, compound

HRID 1931118Notes

Reaction equation

HRID 1931118 reaction equation
[OH-].[Na+].[C:3]([C:7]1[N:11]([CH3:12])[N:10]([CH2:13][CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)/[C:9](=[N:19]/C(=O)C(F)(F)F)/[CH:8]=1)([CH3:6])([CH3:5])[CH3:4]>O.CO>[C:3]([C:7]1[N:11]([CH3:12])[N:10]([CH2:13][CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18]2)[C:9](=[NH:19])[CH:8]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178480297HCID 178480297, compound

Product 1

HCID 68556947HCID 68556947, compoundYield 97.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A solution of sodium hydroxide (1.7 g, 41.5 mmol) in water (2 mL) was added to a solution of Example 127D (2.75 g, 8.3 mmol) in MeOH (10 mL) and the mixture stirred at 50° C. for 3 hours. After cooling to ambient temperature, the mixture was concentrated under reduced pressure and the residue was partitioned between dichloromethane and water. The aqueous phase was extracted with dichloromethane (3×10 mL). The combined organic extracts were concentrated and the residue crystallized from MeOH and EtOAc to afford the title compound (1.9 g, 8.1 mmol, 97% yield). 1H NMR (300 MHz, Methanol-d4) δ ppm 1.23-1.37 (m, 2H), 1.41 (s, 9H), 1.53-1.64 (m, 2H), 1.64-1.78 (m, 4H), 2.17-2.44 (m, 1H), 3.34 (s, 1H), 3.80 (s, 3H), 4.12 (d, J=7.5 Hz, 2H), 5.75 (s, 1H); MS (ESI+) m/z 236 [M+H]+.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customthe residue was partitioned between dichloromethane and water
  4. extractionThe aqueous phase was extracted with dichloromethane (3×10 mL)
  5. concentrationThe combined organic extracts were concentrated
  6. customthe residue crystallized from MeOH and EtOAc

Sources & evidence

ORD record
ord-11a049e12dc04e42a7aa1840d0aadf8f
Source dataset
uspto-grants-2012_05
Patent number
US08188135B2

Reaction notes

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