Triethylamine → HCID 178496566, compound

HRID 1047232

Reaction equation

HRID 1047232 reaction equation
[CH3:1][O:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([CH2:9][N:10]2[C:15]3=[N:16][C:17]([Sn](C)(C)C)=[CH:18][N:19]=[C:14]3[NH:13][CH2:12][C:11]2=[O:24])[CH2:5][CH2:4]1.Br[C:26]1[C:27]([CH3:34])=[CH:28][C:29]([C:32]#[N:33])=[N:30][CH:31]=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](=[O:24])[CH2:12][NH:13][C:14]3[N:19]=[CH:18][C:17]([C:26]4[C:27]([CH3:34])=[CH:28][C:29]([C:32]#[N:33])=[N:30][CH:31]=4)=[N:16][C:15]2=3)[CH2:5][CH2:4]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 533954685-Bromo-4-methylpyridine-2-carbonitrileHCID 178496569HCID 178496569, compound

Product 1

HCID 178496566HCID 178496566, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-1fbd9a1e59ff4e0895d50c309f4f4119
Source dataset
uspto-grants-2013_10
Patent number
US08569494B2

Linked notes

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