Triethylamine → HCID 178496565、化合物

HRID 1640304

反応式

HRID 1640304 の反応式
[CH3:1][O:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([CH2:9][N:10]2[C:15](=[O:16])[CH2:14][NH:13][C:12]3[N:17]=[CH:18][C:19]([C:21]4[C:22]([CH3:29])=[CH:23][C:24]([C:27]#[N:28])=[N:25][CH:26]=4)=[N:20][C:11]2=3)[CH2:5][CH2:4]1.CO[C@H]1CC[C@H](C[N:39]2[C:44]3=[N:45]C([Sn](C)(C)C)=CN=C3NCC2=O)CC1.BrC1C(C)=CC(C#N)=NC=1.C(N(CC)CC)C.CC1C(P(C2C(C)=CC=CC=2)C2C(C)=CC=CC=2)=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CN(C)C=O>[CH3:1][O:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([CH2:9][N:10]2[C:11]3=[N:20][C:19]([C:21]4[CH:26]=[N:25][C:24]([C:27]5[N:45]=[CH:44][NH:39][N:28]=5)=[CH:23][C:22]=4[CH3:29])=[CH:18][N:17]=[C:12]3[NH:13][CH2:14][C:15]2=[O:16])[CH2:5][CH2:4]1

参加物

8

反応物 5

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 533954685-Bromo-4-methylpyridine-2-carbonitrileHCID 178496566HCID 178496566、化合物HCID 178496569HCID 178496569、化合物

生成物 1

HCID 178496565HCID 178496565、化合物収率 94%

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

5-(8-(((trans)-4-Methoxycyclohexyl)methyl)-7-oxo-5,6,7,8-tetrahydropyrazino[2,3-b]pyrazin-2-yl)-4-methylpicolinonitrile. 1-(((trans)-4-Methoxycyclohexyl)methyl)-7-(trimethylstannyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one (0.721 g, 1.64 mmol), 5-bromo-4-methylpicolinonitrile (0.323 g, 1.64 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.150 g, 0.164 mmol), triethylamine (0.687 mL, 4.93 mmol), tri-ortho-toylphosphine (0.100 g, 0.328 mmol) and dimethylformamide (8 mL) were combined in a sealed reaction vessel. Nitrogen was bubbled through the reaction for 5 min and reaction was heated at 100° C. for 3 h. Reaction is filtered, concentrated and purified by silica gel column chromatography (0-80% ethyl acetate in hexanes). Fractions were combined and concentrated to afford the crude title compound used directly for next step (0.607 g, 1.55 mmol, 94% yield). MS (ESI) m/z 393.5 [M+1]+.

後処理

  1. customNitrogen was bubbled through the reaction for 5 min
  2. customreaction
  3. customReaction
  4. filtrationis filtered
  5. concentrationconcentrated
  6. custompurified by silica gel column chromatography (0-80% ethyl acetate in hexanes)
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-fc6d8ba153e744d0bad23981defe8a17
出典データセット
uspto-grants-2012_02
特許番号
US08110578B2

関連ノート

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