2-[-2-(5,8-Dimethyl[1,2,4]triazolo[1,5-a]pyrazin-2-yl)-vinyl]-5H-imidazo[2,1-a]isoindole → US8796304, 2-[2-(5,8-Bis(trideuteromethyl)-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)-ethyl]-5,5-dideutero-5H-imidazo[2,1-a]isoindole

HRID 1039341ノート

反応式

HRID 1039341 の反応式
[CH3:1][C:2]1[N:7]2[N:8]=[C:9]([CH:11]=[CH:12][C:13]3[N:14]=[C:15]4[C:23]5[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=5)[CH2:17][N:16]4[CH:24]=3)[N:10]=[C:6]2[C:5]([CH3:25])=[N:4][CH:3]=1>CO.[Pd]>[CH3:1][C:2]1[N:7]2[N:8]=[C:9]([CH2:11][CH2:12][C:13]3[N:14]=[C:15]4[C:23]5[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=5)[CH2:17][N:16]4[CH:24]=3)[N:10]=[C:6]2[C:5]([CH3:25])=[N:4][CH:3]=1

参加物

4

反応物 1

HCID 696708672-[-2-(5,8-Dimethyl[1,2,4]triazolo[1,5-a]pyrazin-2-yl)-vinyl]-5H-imidazo[2,1-a]isoindole

生成物 1

HCID 57331250US8796304, 2-[2-(5,8-Bis(trideuteromethyl)-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)-ethyl]-5,5-dideutero-5H-imidazo[2,1-a]isoindole収率 36.2%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

To a solution of 2-[-2-(5,8-Dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)-vinyl]-5H-imidazo[2,1-a]isoindole (139 mg, 0.423 mmol) in methanol (100 mL) was added 10% palladium on carbon (27 mg). A current of hydrogen gas was bubbled through, and the reaction was kept under an atmosphere of hydrogen overnight with stirring. After filtration the organics were evaporated onto silica gel (2 g). Chromatography (gradient elution; A:B 100:0 to 0:100, where A is ethyl acetate and B is 10% MeOH in ethyl acetate) afforded the title compound as a white solid (50.6 mg, 36%). 1H NMR (500 MHz, CDCl3): δ 7.86-7.82 (m, 2H), 7.46-7.42 (m, 2H), 7.33 (t, J=7.5 Hz, 1H), 7.02 (s, 1H), 4.84 (s, 2H), 3.44 (dd, J=8.9, 6.6 Hz, 2H), 3.33 (dd, J=8.9, 6.6 Hz, 2H), 2.91 (s, 3H), 2.73 (s, 3H). LC-MS: m/z=331.0 (MH+), tR=0.74 minutes.

後処理

  1. customA current of hydrogen gas was bubbled through, and the reaction
  2. filtrationAfter filtration the
  3. customorganics were evaporated onto silica gel (2 g)
  4. washChromatography (gradient elution

出典と根拠

ORDレコード
ord-dd8ca31e840841c19e88dab4ac5ddb7b
出典データセット
uspto-grants-2013_10
特許番号
US08552045B2

反応ノート

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