Triethylamine → HCID 178496584, compound

HRID 1640313Notes

Reaction equation

HRID 1640313 reaction equation
[CH3:1][O:2][C@@H:3]1[CH2:8][CH2:7][C@H:6]([N:9]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([C:19]4[C:20]([CH3:36])=[N:21][C:22]([C:25]5[N:29](C6CCCCO6)[CH:28]=[N:27][N:26]=5)=[CH:23][CH:24]=4)[N:17]=3)[NH:12][C:11](=[O:37])[CH2:10]2)[CH2:5][CH2:4]1.CO[C@@H]1CC[C@H](N2C3C(=NC=C([Sn](C)(C)C)N=3)NC(=O)C2)CC1.BrC1C(C)=NC(C2N=CN(C3CCCCO3)N=2)=CC=1.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>[CH3:1][O:2][C@@H:3]1[CH2:8][CH2:7][C@H:6]([N:9]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([C:19]4[C:20]([CH3:36])=[N:21][C:22]([C:25]5[NH:29][CH:28]=[N:27][N:26]=5)=[CH:23][CH:24]=4)[N:17]=3)[NH:12][C:11](=[O:37])[CH2:10]2)[CH2:5][CH2:4]1

Participants

8

Reactant 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 178496583HCID 178496583, compoundHCID 178496585HCID 178496585, compound

Product 1

HCID 178496584HCID 178496584, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

4-((cis)-4-Methoxycyclohexyl)-6-(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. 4-((cis)-4-Methoxycyclohexyl)-6-(trimethylstannyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one 0.292 g, 0.687 mmol), 3-bromo-2-methyl-6-(1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl)pyridine (0.244 g, 0.756 mmol), tris(dibenzylideneacetone)dipalladium (0.063 g, 0.069 mmol), tri-o-tolylphosphine (0.042 g, 0.137 mmol), triethylamine (0.287 mL, 2.061 mmol) and dimethylformamide (5.0 mL) were combined in a screw capped flask and heated to 95° C. for 1 h. The solution was condensed under reduced pressure and purified using Biotage chromatography (0-80% ethyl acetate in hexanes followed by 0-10% methanol in ethyl acetate) to afford the title compound (0.279 g, 0.687 mmol, 80% yield). MS (ESI) m/z 505.6 [M+1]+.

Workup

  1. customcapped flask
  2. customcondensed under reduced pressure
  3. custompurified

Sources & evidence

ORD record
ord-62b3d7f74f0647608b9a22945ac204c6
Source dataset
uspto-grants-2012_02
Patent number
US08110578B2

Reaction notes

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