1,8-Diazabicyclo(5.4.0)undec-7-ene → 3-(4-Cyclopropyl-5-pyridin-4-yl-4H-[1,2,4]triazol-3-yl)-2-methyl-acrylic acid ethyl ester

HRID 732099

반응식

HRID 732099 반응식
[CH:1]1([N:4]2[C:8]([C:9]3[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=3)=[N:7][N:6]=[C:5]2[CH2:15]O)[CH2:3][CH2:2]1.[CH2:17]([O:19][C:20](=[O:31])[CH:21](P(OCC)(OCC)=O)[CH3:22])[CH3:18].C1CCN2C(=NCCC2)CC1>C(#N)C.O=[Mn]=O>[CH2:17]([O:19][C:20](=[O:31])[C:21]([CH3:22])=[CH:15][C:5]1[N:4]([CH:1]2[CH2:2][CH2:3]2)[C:8]([C:9]2[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=2)=[N:7][N:6]=1)[CH3:18]

참가 물질

6

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 107155Triethyl 2-phosphonopropionateHCID 57837966(4-cyclopropyl-5-pyridin-4-yl-4H-[1,2,4]triazol-3-yl)-methanol

생성물 1

HCID 670709853-(4-Cyclopropyl-5-pyridin-4-yl-4H-[1,2,4]triazol-3-yl)-2-methyl-acrylic acid ethyl ester

시약·촉매·용매 2

HCID 14801Manganese dioxide촉매HCID 6342Acetonitrile용매

반응 조건

온도
80 °C

실험 절차

(4-cyclopropyl-5-pyridin-4-yl-4H-[1,2,4]triazol-3-yl)-methanol (6.8 g, 31.4 mmol) was mixed with MnO2 (40 g, 0.46 mol) in acetonitrile at r.t. for 2 hours and then heated at 80° C. for another 30 min. The reaction mixture was filtered through celite. The filtrate was mixed with 2-(diethoxy-phosphoryl)-propionic acid ethyl ester (12.35 g, 51.8 mmol) and DBU (7.17 g, 47 mmol) at 80 to 90° C. for 4 h. The reaction mixture was concentrated, dissolved in EA and washed with water and brine. The organic layer was dried, concentrated and triturated with hex. to give the title compound in 5.76 g (61%) yield. 1H-NMR: 8.78(d, 2H), 7.78 (d, 2H), 7.67 (s, 1H), 4.32 (q, 2H), 3.43 (m, 1H), 2.53 (s, 3H), 1.38 (t, 3H), 1.24 (m, 2H) and 0.73 (m, 2H).

후처리

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationThe reaction mixture was concentrated
  3. dissolutiondissolved in EA
  4. washwashed with water and brine
  5. customThe organic layer was dried
  6. concentrationconcentrated
  7. customtriturated with hex

출처 및 근거

ORD 기록
ord-17e9a081f4dc407bb38662c6b8452b97
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585881B2

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