Sodium Carbonate → 4-(8-(Cyclobutylamino)-[1,2,4]triazolo[1,5-a]pyrazin-5-yl)furan-2-carboxamide

HRID 1093961

反応式

HRID 1093961 の反応式
Br[C:2]1[N:7]2[N:8]=[CH:9][N:10]=[C:6]2[C:5]([NH:11][CH:12]2[CH2:15][CH2:14][CH2:13]2)=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:24]2[CH:25]=[C:26]([C:29]([NH2:31])=[O:30])[O:27][CH:28]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd].[Pd].[Pd].[Pd].O1CCOCC1>[CH:12]1([NH:11][C:5]2[C:6]3[N:7]([N:8]=[CH:9][N:10]=3)[C:2]([C:24]3[CH:25]=[C:26]([C:29]([NH2:31])=[O:30])[O:27][CH:28]=3)=[CH:3][N:4]=2)[CH2:15][CH2:14][CH2:13]1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 575899904-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carboxamideHCID 576995005-bromo-N-cyclobutyl-[1,2,4]triazolo[1,5-a]pyrazin-8-amine

生成物 1

HCID 251153794-(8-(Cyclobutylamino)-[1,2,4]triazolo[1,5-a]pyrazin-5-yl)furan-2-carboxamide収率 91.1%

試薬・触媒・溶媒 2

HCID 86600928Tetrakis palladium triphenylphosphine触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

The product of Step 1 (900 mg, 3.35 mmol), Intermediate 5 (4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-furan-2-carboxylic acid amide, 1.8 g, 4.02 mmol), tetrakis palladium triphenylphosphine (970 mg, 0.84 mmol), sodium carbonate solution (1.5 M, 18 mL, 26.8 mmol) and dioxane (20 mL) are combined in a flask. The mixture is degassed with nitrogen for 10 min then sealed and heated at 90° C. for 18 h. The reaction mixture is cooled and the precipitate collected by filtration. The precipitate is washed with 2% methanol: dichloromethane (2 mL) to give the title compound as a white solid (910 mg, 91%). 1H-NMR (400 MHz, d6-DMSO) =1.74-1.76 (m, 2H), 2.22-2.26 (m, 2H), 2.32 (brs, 2H), 4.70 (brd, 1H, J=7.6), 7.58 (s, 1H), 7.86 (s, 1H), 7.97 (s, 1H), 8.12 (s, 1H), 8.35 (d, 1H, J=7.2), 8.69 (d, 11H, J=9.6). LCMS: Rt 2.63 min (90.4%), m/z (APCI) 299 (M+H)+.

後処理

  1. customThe mixture is degassed with nitrogen for 10 min
  2. customthen sealed
  3. temperatureThe reaction mixture is cooled
  4. filtrationthe precipitate collected by filtration
  5. washThe precipitate is washed with 2% methanol

出典と根拠

ORDレコード
ord-5fe68fceb45e4aa9983e0f7c82f52b11
出典データセット
uspto-grants-2012_03
特許番号
US08133895B2

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