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Dichloromethane → 1-ethyl-N-(4-methyl-3-(1-methyl-5-morpholino-6-oxo-1,6-dihydropyridin-3-yl)phenyl)-6-oxo-5-(trifluoromethyl)-1,6-dihydropyridine-3-carboxamide

HRID 594081
ノート
印刷プレビュー

反応式

HRID 594081 の反応式
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:22])=[C:6]([C:8]2[CH:9]=[C:10]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[C:11](=[O:15])[N:12]([CH3:14])[CH:13]=2)[CH:7]=1.Br[C:24]1[CH:25]=[C:26]([C:33]([F:36])([F:35])[F:34])[C:27](=[O:32])[N:28]([CH2:30][CH3:31])[CH:29]=1.C(Cl)Cl.C1CCN2C(=NCCC2)CC1.C1C[O:54][CH2:53]C1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:30]([N:28]1[C:27](=[O:32])[C:26]([C:33]([F:36])([F:35])[F:34])=[CH:25][C:24]([C:53]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH3:22])=[C:6]([C:8]3[CH:9]=[C:10]([N:16]4[CH2:17][CH2:18][O:19][CH2:20][CH2:21]4)[C:11](=[O:15])[N:12]([CH3:14])[CH:13]=3)[CH:7]=2)=[O:54])=[CH:29]1)[CH3:31]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 6344DichloromethaneHCID 8028TetrahydrofuranHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 904081725-(5-amino-2-methylphenyl)-1-methyl-3-morpholinopyridin-2(1H)-oneHCID 904088165-bromo-1-ethyl-3-(trifluoromethyl)pyridin-2(1H)-one

生成物 1

HCID 90407968
1-ethyl-N-(4-methyl-3-(1-methyl-5-morpholino-6-oxo-1,6-dihydropyridin-3-yl)phenyl)-6-oxo-5-(trifluoromethyl)-1,6-dihydropyridine-3-carboxamide
収率 15%

試薬・触媒・溶媒 1

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒

反応条件

温度
150 °C

実験手順

In a microwave tube was added 5-(5-amino-2-methylphenyl)-1-methyl-3-morpholinopyridin-2(1H)-one (1.0 equiv.), 5-bromo-1-ethyl-3-(trifluoromethyl)pyridin-2(1H)-one (2.0 equiv.), PdCl2(dppf).CH2Cl2 adduct (0.1 equiv.), Mo(CO)6 (1.0 equiv.), and THF (0.3 M). The mixture was capped and stirred while DBU (3.0 equiv.) was added, fizzing occurred and the tube was subsequently heated in the microwave at 150° C. for 15 min at which time LCMS indicated full conversion to product (M+H=517). The reaction was filtered, concentrated, and purified via preparative HPLC to yield 1-ethyl-N-(4-methyl-3-(1-methyl-5-morpholino-6-oxo-1,6-dihydropyridin-3-yl)phenyl)-6-oxo-5-(trifluoromethyl)-1,6-dihydropyridine-3-carboxamide (15% yield). 1H NMR (400 MHz, <cd3od>) δ ppm 1.42 (t, J=7.24 Hz, 3H) 2.30 (s, 3H) 3.08-3.21 (m, 4H) 3.64 (s, 3H) 3.80-3.92 (m, 4H) 4.16 (q, J=7.04 Hz, 2H) 6.93 (d, J=1.96 Hz, 1H) 7.28 (d, J=8.22 Hz, 1H) 7.34 (d, J=1.96 Hz, 1H) 7.47-7.60 (m, 2H) 8.48 (d, J=1.96 Hz, 1H) 8.70 (d, J=2.35 Hz, 1H). LCMS (m/z) (M+H)=517.1, Rt=0.81 min.

後処理

  1. customThe mixture was capped
  2. additionwas added
  3. filtrationThe reaction was filtered
  4. concentrationconcentrated
  5. custompurified via preparative HPLC

出典と根拠

ORDレコード
ord-093ccda7c42841e9a60c93ac406176a5
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09242969B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート