Ethyl 3-(oxan-4-yl)-3-oxopropanoate → HCID 178433774, compound

HRID 510368Notes

Reaction equation

HRID 510368 reaction equation
O=[C:2]([CH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)[CH2:3][C:4]([O:6]CC)=O.[CH3:15][C:16]1[C:20]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[C:23]=2[CH3:32])=[C:19]([NH2:33])[NH:18][N:17]=1>C(O)(=O)C>[CH3:15][C:16]1[C:20]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:30])([F:29])[F:31])[C:23]=2[CH3:32])=[C:19]2[NH:33][C:2]([CH:9]3[CH2:10][CH2:11][O:12][CH2:13][CH2:14]3)=[CH:3][C:4](=[O:6])[N:18]2[N:17]=1

Participants

4

Reactant 2

HCID 23144053Ethyl 3-(oxan-4-yl)-3-oxopropanoateHCID 1784346743-methyl-4-{[2-methyl-3-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-5-amine

Product 1

HCID 178433774HCID 178433774, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
140 °C

Procedure

To a suspension of ethyl 3-oxo-3-(tetrahydro-2H-pyran-4-yl)propanoate (0.78 mg, 3.90 mmol) in acetic acid was added 3-methyl-4-{[2-methyl-3-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-5-amine (1.0 g, 3.71 mmol) in microwave reaction vessel. It was sealed and heated with microwave reactor at 140° C. for 40 minutes. The reaction mixture was cooled, diluted with acetic acid (5 mL) and stood for overnight. Precipitate was observed, filtered. Solid was washed with acetic acid (2 mL) and cooled methanol (2 mL). Solid was dried. The titled compound was obtained and used in next step. (1.02 g, 68%) LC/MS: MS (ES+) m/e 406 (MH+).

Workup

  1. customin microwave reaction vessel
  2. customIt was sealed
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. washSolid was washed with acetic acid (2 mL)
  6. temperaturecooled methanol (2 mL)
  7. customSolid was dried

Sources & evidence

ORD record
ord-ce8cb09a0bbb4c82a1f4e845c8dd7ec0
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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