Nitrogen → HCID 86690320, compound

HRID 1521900Notes

Reaction equation

HRID 1521900 reaction equation
Br[C:2]1[C:3]([NH2:22])=[N:4][C:5]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[N:7]=1.N#N.C(N(CC)CC)C.[C:32]([OH:40])(=[O:39])[CH2:33][CH2:34][CH2:35][CH2:36][C:37]#[CH:38]>O1CCOCC1.C(Cl)Cl.[Cu]I.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[NH2:22][C:3]1[C:2]([C:38]#[C:37][CH2:36][CH2:35][CH2:34][CH2:33][C:32]([OH:40])=[O:39])=[N:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=[C:5]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)[N:4]=1

Participants

9

Reactant 4

HCID 947NitrogenHCID 8471TriethylamineHCID 43779506-Heptynoic acidHCID 86690308HCID 86690308, compound

Product 1

HCID 86690320HCID 86690320, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418807HCID 178418807, compoundCatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

3-Bromo-5,6-di-p-tolylpyrazin-2-amine (Example 1, step 3)(200 mg, 0.565 mmol) in anhydrous dioxane (10 ml), degassed with N2 was treated with triethylamine (0.708 ml, 5.08 mmol), hept-6-ynoic acid (0.179 ml, 1.129 mmol), copper(I) iodide (32.3 mg, 0.169 mmol) and PdCl2(dppf)-CH2Cl2-adduct (46.1 mg, 0.056 mmol). The reaction mixture was stirred at room temperature for 16 hours. The resulting mixture was diluted with DCM (10 ml) and dry loaded onto silica. Purification by chromatography on silica eluting with 0-100% EtOAc in iso-hexane followed by 20% MeOH in EtOAc afforded the titled compound;

Workup

  1. customdry
  2. customPurification by chromatography on silica eluting with 0-100% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-e89f450387274348b8b774600311f6a3
Source dataset
uspto-grants-2015_07
Patent number
US09073932B2

Reaction notes

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