Ethyl 3-(oxan-4-yl)-3-oxopropanoate → HCID 178515695, compound

HRID 510375Notes

Reaction equation

HRID 510375 reaction equation
OC(C(F)(F)F)=O.[Cl:8][C:9]1[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:16][C:17]1[C:18]([NH2:26])=[N:19][NH:20][C:21]=1[C:22]([F:25])([F:24])[F:23].O=[C:28]([CH:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1)[CH2:29][C:30](OCC)=[O:31]>C(O)(=O)C>[Cl:8][C:9]1[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:16][C:17]1[C:21]([C:22]([F:25])([F:23])[F:24])=[N:20][N:19]2[C:30]([OH:31])=[CH:29][C:28]([CH:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)=[N:26][C:18]=12

Participants

4

Reactant 2

HCID 23144053Ethyl 3-(oxan-4-yl)-3-oxopropanoateHCID 86724870HCID 86724870, compound

Product 1

HCID 178515695HCID 178515695, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a suspension of 4-[(2,3-dichlorophenyl)methyl]-5-(trifluoromethyl)-1H-pyrazol-3-amine TFA salt (201 mg, 0.48 mmol) in acetic acid (2 mL) was added ethyl 3-oxo-3-(tetrahydro-2H-pyran-4-yl)propanoate (100 mg, 0.50 mmol). The reaction vessel was sealed, stirred and irradiated (microwave) at 140° C. for 40 minutes. The reaction mixture was cooled and diluted with acetic acid (5 mL). It was stood still overnight. The precipitate was collected, washed with acetic acid (2 mL), then with cooled methanol (2 mL) and dried to give crude product. The crude material was purified by reverse-phase HPLC to provide titled compound. (16 mg, 7.5%); LC/MS: MS (ES+) m/e 446 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.75-1.77 (m, 4H) 2.82 (s, 1H) 3.38-3.41 (m, 2H) 3.96 (dd, J=10.99, 2.91 Hz, 2H) 4.21 (s, 2H) 5.84 (s, 1H) 6.77-6.83 (m, 1H) 7.25 (t, J=7.96 Hz, 1H) 7.54 (dd, J=7.96, 1.39 Hz, 1H) 12.22 (s, 1H).

Workup

  1. customThe reaction vessel was sealed
  2. customirradiated (microwave) at 140° C. for 40 minutes
  3. temperatureThe reaction mixture was cooled
  4. customThe precipitate was collected
  5. washwashed with acetic acid (2 mL)
  6. dry with materialwith cooled methanol (2 mL) and dried
  7. customto give crude product
  8. customThe crude material was purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-af7e6ec1fc234a9aa47a3ef3c9056657
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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