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

HRID 1095464

반응식

HRID 1095464 반응식
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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 86600928Tetrakis palladium triphenylphosphine촉매HCID 312751,4-Dioxane용매

반응 조건

온도
90 °C

실험 절차

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, 1H, J=9.6). LCMS: Rt 2.63 min (90.4%), m/z (APCI) 299 (M+H)+.

후처리

  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

출처 및 근거

ORD 기록
ord-56e83e31b847458a863f42b481f7ec1c
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08138193B2

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