Diisopropylethylamine → 4-{4-[2-(2,5-Dichloro-phenoxy)-5-fluoro-pyridine-3-carbonyl]-3,4-dihydro-2H-quinoxaline-1-carbonyl}-benzoic acid methyl ester

HRID 1877417

반응식

HRID 1877417 반응식
[Cl:1][C:2]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:3]=1[O:4][C:5]1[C:10]([C:11]([N:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][CH2:15][CH2:14]2)=[O:12])=[CH:9][C:8]([F:23])=[CH:7][N:6]=1.C(N(C(C)C)C(C)C)C.[CH3:38][O:39][C:40](=[O:50])[C:41]1[CH:46]=[CH:45][C:44]([C:47](Cl)=[O:48])=[CH:43][CH:42]=1>CN(C=O)C>[CH3:38][O:39][C:40](=[O:50])[C:41]1[CH:46]=[CH:45][C:44]([C:47]([N:16]2[C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:13]([C:11]([C:10]3[C:5]([O:4][C:3]4[CH:24]=[C:25]([Cl:28])[CH:26]=[CH:27][C:2]=4[Cl:1])=[N:6][CH:7]=[C:8]([F:23])[CH:9]=3)=[O:12])[CH2:14][CH2:15]2)=[O:48])=[CH:43][CH:42]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 81850Methyl 4-(chlorocarbonyl)benzoateHCID 59294514[2-(2,5-Dichloro-phenoxy)-5-fluoro-pyridin-3-yl]-(3,4-dihydro-2H-quinoxalin-1-yl)-methanone

생성물 1

HCID 673666084-{4-[2-(2,5-Dichloro-phenoxy)-5-fluoro-pyridine-3-carbonyl]-3,4-dihydro-2H-quinoxaline-1-carbonyl}-benzoic acid methyl ester수율 11%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
120 °C

실험 절차

To a solution of [2-(2,5-dichloro-phenoxy)-5-fluoro-pyridin-3-yl]-(3,4-dihydro-2H-quinoxalin-1-yl)-methanone (52.3 mg, 0.125 mmol, 1.0 equiv; Example 147) in anhydrous DMF (1 mL) was added N-ethyldiisopropylamine (65 mg, 85 μL, 0.5 mmol, 4.0 equiv; [CAS RN 7087-68-5]) and 4-chlorocarbonyl-benzoic acid methyl ester (29.8 mg, 0.15 mmol, 1.2 equiv; [CAS RN 7377-26-6]). The reaction mixture was heated by microwave irradiation to 120° C. for 15 min. Removal of the solvent mixture under reduced pressure and purification by preparative HPLC on reversed phase (Xterra® PrepMSC 18, 5 μm, 19×50 mm column equipped with a Gilson Liquid Handler 215 autosampler, two Rainin Dynamax® SD-300 pumps, a Sedex ELSD 75 lightscatter and a Dionex UVD 340S UV detector) eluting with a gradient of acetonitrile/water provided 7.8 mg (11%) of the title compound as a white powder. MS (ISP): 580.0 [M+H]+.

후처리

  1. customRemoval of the solvent mixture
  2. customunder reduced pressure and purification by preparative HPLC on reversed phase (Xterra® PrepMSC 18, 5 μm, 19×50 mm column
  3. customequipped with a Gilson Liquid Handler 215 autosampler, two Rainin Dynamax® SD-300 pumps
  4. washa Sedex ELSD 75 lightscatter and a Dionex UVD 340S UV detector) eluting with a gradient of acetonitrile/water

출처 및 근거

ORD 기록
ord-d19a03c1a71f46fb86a1e5dc3f497569
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08309734B2

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