Ethyl 3-(oxan-4-yl)-3-oxopropanoate → HCID 178437906, compound

HRID 510386Notes

Reaction equation

HRID 510386 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][C:10]1[C:11]([CH2:16][CH3:17])=[N:12][NH:13][C:14]=1[NH2:15].O=[C:19]([CH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1)[CH2:20][C:21](OCC)=[O:22]>C(O)(=O)C>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][C:10]1[C:11]([CH2:16][CH3:17])=[N:12][N:13]2[C:21]([OH:22])=[CH:20][C:19]([CH:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[N:15][C:14]=12

Participants

4

Reactant 2

HCID 23144053Ethyl 3-(oxan-4-yl)-3-oxopropanoateHCID 178438049HCID 178438049, compound

Product 1

HCID 178437906HCID 178437906, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a suspension of 4-[(2,3-dichlorophenyl)methyl]-3-ethyl-1H-pyrazol-5-amine (257 mg, 0.95 mmol) in acetic acid (2 mL) was added ethyl 3-oxo-3-(tetrahydro-2H-pyran-4-yl)propanoate (200, 1.0 mmol). The reaction vessel was sealed, stirred and irradiated (microwave) at 140° C. for 40 minutes. Reaction mixture was cooled and diluted with acetic acid (2 mL). It was stood still overnight. The precipitate was collected, washed with acetic acid (1 mL), then with methanol (2 mL×2) and dried to afford expected compound. (288 mg, 71%); LC/MS: MS (ES+) m/e 406 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.06 (t, J=7.45 Hz, 3H) 1.76 (br. s., 4H) 1.91 (s, 3H) 2.45 (q, J=7.41 Hz, 2H) 3.39 (br. s., 2H) 4.07 (s, 2H) 5.56 (s, 1H) 6.87 (s, 1H) 7.25 (s, 1H) 7.51 (s, 1H).

Workup

  1. customThe reaction vessel was sealed
  2. customirradiated (microwave) at 140° C. for 40 minutes
  3. customReaction mixture
  4. temperaturewas cooled
  5. customThe precipitate was collected
  6. washwashed with acetic acid (1 mL)
  7. dry with materialwith methanol (2 mL×2) and dried

Sources & evidence

ORD record
ord-2991a33743284fb68305aa5824ed1b27
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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