Sodium Methoxide → HCID 71271625, compound

HRID 510381Notes

Reaction equation

HRID 510381 reaction equation
Cl[C:2]1[N:7]2[N:8]=[CH:9][C:10]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[C:13]=3[CH3:22])=[C:6]2[N:5]=[C:4]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[CH:3]=1.[CH3:29][O-:30].[Na+]>CO>[CH3:29][O:30][C:2]1[N:7]2[N:8]=[CH:9][C:10]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[C:13]=3[CH3:22])=[C:6]2[N:5]=[C:4]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[CH:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 71527716HCID 71527716, compound

Product 1

HCID 71271625HCID 71271625, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 4-(7-chloro-3-(2-methyl-3-(trifluoromethyl)benzyl)pyrazolo[1,5-a]pyrimidin-5-yl)morpholine (181 mg, 0.44 mmol) in methanol (5 mL) stirred under nitrogen at 0° C. was added a 33% solution of sodium methoxide in dropwise. The reaction mixture was stirred at 40° C. for 1 hour. Solvent was removed in vacuo. The residue was dissolved with ethyl acetate (30 mL) and water (10 mL). Two layers were separated. Organic layer was dried and concentrated. The crude product was purified by reverse-phase HPLC to provide the titled compound. (15 mg, 8.4%); LC/MS: MS (ES+) m/e 407 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.39-2.47 (m, 3H) 3.60 (br. s., 2H) 3.61 (d, J=4.55 Hz, 2H) 3.65-3.73 (m, 4H).

Workup

  1. customSolvent was removed in vacuo
  2. dissolutionThe residue was dissolved with ethyl acetate (30 mL) and water (10 mL)
  3. customTwo layers were separated
  4. customOrganic layer was dried
  5. concentrationconcentrated
  6. customThe crude product was purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-af8b8140b6414c5fa29d76962023ab5c
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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