HCID 58382109, compound → HCID 58382290, compound

HRID 1628084Notes

Reaction equation

HRID 1628084 reaction equation
[S:1]([N:11]1[C:15]2=[N:16][CH:17]=[C:18]([C:20]#[N:21])[N:19]=[C:14]2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([Mg]Br)=[CH:26][CH:25]=1>C1COCC1>[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([C:20]([C:18]2[N:19]=[C:14]3[CH:13]=[CH:12][N:11]([S:1]([C:4]4[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=4)(=[O:2])=[O:3])[C:15]3=[N:16][CH:17]=2)=[NH:21])=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 58382109HCID 58382109, compoundHCID 178491912HCID 178491912, compound

Product 1

HCID 58382290HCID 58382290, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 5-tosyl-5H-pyrrolo[2,3-b]pyrazine-2-carbonitrile (0.500 g, 1.68 mmol) in anhydrous THF (3.35 mL) was added molecular sieves (4A, beads, 8-12 mesh, 0.643 g). The mixture was stirred at rt for about 40 min. A solution of (4-methoxyphenyl)magnesium bromide (0.5 M in THF, 4.12 mL, 2.01 mmol,) was added dropwise over about 3 min. The mixture was stirred at rt for about 2 h. The mixture was concentrated in vacuo to give (4-methoxyphenyl)(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanimine which was assumed to be quantitative and used immediately in the next step: LC/MS (Table 2, Method b) Rt=2.25 min; MS m/z: 407 (M+H)+.

Workup

  1. stirringThe mixture was stirred at rt for about 2 h
  2. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-fe887e8fc3444269bc615131e5a5935a
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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