Ethyl 3-(oxan-4-yl)-3-oxopropanoate → HCID 178515695、化合物

HRID 510375ノート

反応式

HRID 510375 の反応式
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

参加物

4

反応物 2

HCID 23144053Ethyl 3-(oxan-4-yl)-3-oxopropanoateHCID 86724870HCID 86724870、化合物

生成物 1

HCID 178515695HCID 178515695、化合物

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-af7e6ec1fc234a9aa47a3ef3c9056657
出典データセット
uspto-grants-2015_08
特許番号
US09096605B2

反応ノート

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