Hydrochloric Acid → HCID 178422983, compound

HRID 510392Notes

Reaction equation

HRID 510392 reaction equation
[NH2:1][C:2]1[NH:6][NH:5][C:4](=[O:7])[C:3]=1[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[C:10]=1[CH3:19].O=[C:21]([CH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1)[CH2:22][C:23](OCC)=[O:24].Cl.O1CCOCC1>C(O)C>[CH3:19][C:10]1[C:11]([C:15]([F:17])([F:18])[F:16])=[CH:12][CH:13]=[CH:14][C:9]=1[CH2:8][C:3]1[C:4]([OH:7])=[N:5][N:6]2[C:23]([OH:24])=[CH:22][C:21]([CH:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[N:1][C:2]=12

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 23144053Ethyl 3-(oxan-4-yl)-3-oxopropanoateHCID 71270705HCID 71270705, compound

Product 1

HCID 178422983HCID 178422983, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 5-amino-4-{[2-methyl-3-(trifluoromethyl)phenyl]methyl}-1,2-dihydro-3H-pyrazol-3-one (136 mg, 0.5 mmol) in ethanol (1 mL) were added ethyl 3-oxo-3-(tetrahydro-2H-pyran-4-yl)propanoate (100 mg, 0.5 mmol) and 4 M HCl solution in dioxane (25 uL, 0.1 mmol). The reaction mixture was irradiated (microwave) at 110° C. for 30 minutes. Reaction was cooled down. The precipitate was collected by filtration. It was washed with acetic acid (1 mL), then methanol (1 mL) and dried. The titled compound was obtained. (52 mg, 25%); LC/MS: MS (ES+) m/e 408 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.69 (dd, J=12.51, 4.17 Hz, 1H) 1.73-1.80 (m, 3H) 2.46 (s, 3H) 2.72 (s, 1H) 3.34-3.45 (m, 2H) 3.83 (s, 2H) 3.93 (br. s., 2H) 5.51 (s, 1H) 7.15 (d, J=7.58 Hz, 1H) 7.29 (t, J=7.71 Hz, 1H) 7.54 (d, J=8.34 Hz, 1H) 11.46 (s, 1H).

Workup

  1. customThe reaction mixture was irradiated (microwave) at 110° C. for 30 minutes
  2. customReaction
  3. temperaturewas cooled down
  4. filtrationThe precipitate was collected by filtration
  5. washIt was washed with acetic acid (1 mL)
  6. dry with materialmethanol (1 mL) and dried

Sources & evidence

ORD record
ord-6be408137cd446d8b9b24981ff164de5
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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