Triethylamine → HCID 178516733, compound

HRID 2361219Notes

Reaction equation

O1CCCCC1[N:7]1[CH:11]=[N:10][C:9]([C:12]2[N:17]=[CH:16][C:15]([C:18]3[N:19]=[C:20]4[N:27]([CH:28]5[CH2:33][CH2:32][O:31][CH2:30][CH2:29]5)[CH2:26][C:25](=[O:34])[NH:24][C:21]4=[N:22][CH:23]=3)=[CH:14][CH:13]=2)=[N:8]1.BrC1C=CC(C2N=CN(C3CCCCO3)N=2)=NC=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>[NH:7]1[CH:11]=[N:10][C:9]([C:12]2[N:17]=[CH:16][C:15]([C:18]3[N:19]=[C:20]4[N:27]([CH:28]5[CH2:29][CH2:30][O:31][CH2:32][CH2:33]5)[CH2:26][C:25](=[O:34])[NH:24][C:21]4=[N:22][CH:23]=3)=[CH:14][CH:13]=2)=[N:8]1

Participants

Conditions

Temperature: 95 °C

Procedure

6-(6-(1-(Tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl)pyridin-3-yl)-4-(tetrahydro-2H-pyran-4-yl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one. A mixture of 4-(tetrahydro-2H-pyran-4-yl)-6-(trimethylstannyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(111)-one (1 equiv), 5-bromo-2-(1-(tetrahydro-2H-pyran-2-yl)-1H -1,2,4-triazol-3-yl)pyridine (1.2 equiv), tris(dibenzylideneacetone)dipalladium (0.1 equiv), tri-o-tolylphosphine (0.2 equiv), triethylamine (3 equiv) and N,N-dimethylformamide was heated at 95° C. for 3 h under nitrogen. Concentration and chromatography purification give the desired product in 39% yield. MS (ESI) m/z 463.1 [M+1]+.

Workup

concentrationConcentration and chromatography purification

Sources & evidence

ORD record: ord-357db8a92bc442c3b3a6a737d50d25b6
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08686135B2

Reaction notes

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