4-Acetylbenzoic Acid → 4-{3E-[5-(4-Isobutyl-4H-[1,2,4]triazol-3-yl)-2,4-dimethoxy-phenyl]-acryloyl}-benzoic acid

HRID 10737노트

반응식

HRID 10737 반응식
[C:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH2:13]([N:17]1[CH:21]=[N:20][N:19]=[C:18]1[C:22]1[C:23]([O:32][CH3:33])=[CH:24][C:25]([O:30][CH3:31])=[C:26]([CH:29]=1)[CH:27]=O)[CH:14]([CH3:16])[CH3:15].C[O-].[Li+]>CN(C)C=O>[CH2:13]([N:17]1[CH:21]=[N:20][N:19]=[C:18]1[C:22]1[C:23]([O:32][CH3:33])=[CH:24][C:25]([O:30][CH3:31])=[C:26](/[CH:27]=[CH:2]/[C:1]([C:4]2[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=2)=[O:3])[CH:29]=1)[CH:14]([CH3:16])[CH3:15]

참가 물질

5

반응물 3

HCID 114704-Acetylbenzoic AcidHCID 4177230Lithium methanolate2회HCID 219810255-(4-isobutyl-4H-[1,2,4]triazol-3-yl)-2,4-dimethoxy-benzaldehyde

생성물 1

HCID 103882544-{3E-[5-(4-Isobutyl-4H-[1,2,4]triazol-3-yl)-2,4-dimethoxy-phenyl]-acryloyl}-benzoic acid

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 4-acetyl-benzoic acid (0.12 g, 0.75 mmol) and 5-(4-isobutyl-4H-[1,2,4]triazol-3-yl)-2,4-dimethoxy-benzaldehyde (Ex-109E, 0.24 g, 0.83 mmol) in N,N-dimethylformamide (6 mL) was added lithium methoxide (1.0M in methanol, 3.0 mL, 3.0 mmol). The solution was allowed to stir overnight and additional lithium methoxide (0.11 g, 2.8 mmol). The reaction was quenched with water after 20 hours. The aqueous solution was washed ethyl acetate, acidified to pH 4. The precipitate was filtered, washed with ethanol and dried in vacuo to afford the title compound as a light yellow solid: m.p.>240° C. (dec.). 1H NMR (DMSO-d6) δ 8.59 (s, 1H), 8.18 (d, J=7.9 Hz, 2H), 8.07 (s, 1H), 8.04–8.01 (m, 3H), 7.85 (d, J=15.7 Hz, 1H), 6.84 (s, 1H), 4.06 (s, 3H), 3.92 (s, 3H), 3.66 (d, J=7.2 Hz, 2H), 1.87–1.74 (m, 1H), 0.72 (d, J=6.7 Hz, 6H). MS m/z=436 ([M+H]+, 100%).

후처리

  1. customThe reaction was quenched with water after 20 hours
  2. washThe aqueous solution was washed ethyl acetate
  3. filtrationThe precipitate was filtered
  4. washwashed with ethanol
  5. customdried in vacuo

출처 및 근거

ORD 기록
ord-b7a1710fbe634762b2d90eac36d3d924
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094801B2

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