Triethylamine → HCID 178432648、化合物

HRID 454341ノート

反応式

HRID 454341 の反応式
[CH:1]([N:4]1[C:9]2=[N:10][C:11]([C:14]3[C:15]([CH3:31])=[N:16][C:17]([C:20]4[N:24](C5CCCCO5)[CH:23]=[N:22][N:21]=4)=[CH:18][CH:19]=3)=[CH:12][N:13]=[C:8]2[NH:7][CH2:6][C:5]1=[O:32])([CH3:3])[CH3:2].BrC1C(C)=NC(C2N=CN(C3CCCCO3)N=2)=CC=1.C(N1C2=NC([Sn](C)(C)C)=CN=C2NCC1=O)(C)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CN(C)C=O>[CH:1]([N:4]1[C:9]2=[N:10][C:11]([C:14]3[C:15]([CH3:31])=[N:16][C:17]([C:20]4[NH:24][CH:23]=[N:22][N:21]=4)=[CH:18][CH:19]=3)=[CH:12][N:13]=[C:8]2[NH:7][CH2:6][C:5]1=[O:32])([CH3:3])[CH3:2]

参加物

8

反応物 5

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 582983093-bromo-2-methyl-6-(1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl)pyridineHCID 666075961-Isopropyl-7-(2-methyl-6-(4-(tetrahydro-2H-pyran-2-yl)-4H-1,2,4-triazol-3-yl)pyridin-3-yl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-oneHCID 666080081-Isopropyl-7-(trimethylstannyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one

生成物 1

HCID 178432648HCID 178432648、化合物収率 66.7%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

1-Isopropyl-7-(2-methyl-6-(4-(tetrahydro-2H-pyran-2-yl)-4H-1,2,4-triazol-3-yl)pyridin-3-yl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one. To a flask was added 3-Bromo-2-methyl-6-(1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl)pyridine (0.446 g, 1.380 mmol), 1-isopropyl-7-(trimethylstannyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one (0.490 g, 1.380 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.139 g, 0.152 mmol), tri-o-tolylphosphine (0.092 g, 0.304 mmol), triethylamine (0.577 mL, 4.14 mmol) and N,N-dimethylformamide (3 mL). Nitrogen gas was bubbled through the reaction mixture for 5 min and the mixture was heated to 100° C. for 1 h. After cooling to rt, the reaction mixture was filtered through Celite, rinsed with methanol and concentrated to dryness. The resulting residue was purified by silica gel flash column chromatography (0-80% ethyl acetate in hexanes, followed by 0-10% methanol in dichloromethane) to yield the desired product (0.40 g, 0.921 mmol, 66.7% yield). MS (ESI) m/z 435.5 [M+1]+.

後処理

  1. customNitrogen gas was bubbled through the reaction mixture for 5 min
  2. temperatureAfter cooling to rt
  3. filtrationthe reaction mixture was filtered through Celite
  4. washrinsed with methanol
  5. concentrationconcentrated to dryness
  6. customThe resulting residue was purified by silica gel flash column chromatography (0-80% ethyl acetate in hexanes, followed by 0-10% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-cb9fb7787b6a4ef098c6398343c80405
出典データセット
uspto-grants-2013_07
特許番号
US08492381B2

反応ノート

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