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

HRID 510375노트

반응식

HRID 510375 반응식
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

참가 물질

4

반응물 2

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

생성물 1

HCID 178515695HCID 178515695, 화합물

시약·촉매·용매 1

HCID 176Acetic Acid용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-af7e6ec1fc234a9aa47a3ef3c9056657
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096605B2

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