Sodium Hydroxide → HCID 68556947, compound

HRID 536755Notes

Reaction equation

HRID 536755 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-461fb77ac2a149aabca3d8af6546c749
Source dataset
uspto-grants-2014_10
Patent number
US08859596B2

Reaction notes

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