Potassium Carbonate → HCID 58764244, compound

HRID 2387163Notes

Reaction equation

HRID 2387163 reaction equation
[CH2:1]1[CH2:7][O:6][CH2:5][CH2:4][NH:3][CH2:2]1.Cl.Cl[C:10]1[N:14]([CH3:15])[N:13]=[C:12]([CH3:16])[C:11]=1[CH:17]=[O:18].CN(P(N(C)C)(N(C)C)=O)C.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:15][N:14]1[C:10]([N:3]2[CH2:2][CH2:1][CH2:7][O:6][CH2:5][CH2:4]2)=[C:11]([CH:17]=[O:18])[C:12]([CH3:16])=[N:13]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 12679HexamethylphosphoramideHCID 27773975-Chloro-1,3-dimethylpyrazole-4-carboxaldehydeHCID 230902141,4-Oxazepane hydrochloride

Product 1

HCID 58764244HCID 58764244, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Homomorpholine hydrochloride (28.2 g, 200 mol) was added to a mixture of 5-chloro-1,3-dimethyl-1H-pyrazole-4-carbaldehyde (21.68 g, 0.1368 mol, Example B(45), Step 2), HMPA (30 mL), water (50 mL), and potassium carbonate (59 g, 0.6 mol) at constant stirring and room temperature. The reaction mixture was heated at 80° C. for 50 h, diluted with water, and extracted with ethyl acetate (3×100 mL). The organic extracts were washed with water to weakly alkaline pH and dried with sodium sulfate. The product was purified chromatographically using hexane/ethyl acetate mixture as eluent to afford the title product (18.7 g, 61%). Satisfactory C,H,N-analysis was obtained. 1H NMR (400 MHz, DMSO-d6): δ 1.91 (m, 2H), 2.27 (s, 3H), 3.33 (m, 4H, overlap with H2O peak), 3.62 (s, 3H), 3.72 (m, 2H), 3.81 (m, 2H), 9.83 (s, 1H). LC/MS (API-ES) calcd for C11H17N3O2: 223.13, found (M+H+): 224.1 m/z.

Workup

  1. temperatureThe reaction mixture was heated at 80° C. for 50 h
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. washThe organic extracts were washed with water to weakly alkaline pH
  4. dry with materialdried with sodium sulfate
  5. customThe product was purified chromatographically using hexane/ethyl acetate mixture as eluent

Sources & evidence

ORD record
ord-6006186395b240adb1c887f804e5559f
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

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