Dimethylformamide → HCID 118364837, compound

HRID 1478607Notes

Reaction equation

[NH2:1][C:2]1[C:3]([NH:9][CH2:10][C@H:11]2[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12]2)=[N:4][C:5]([Br:8])=[CH:6][N:7]=1.C[N:25](C=O)C>>[Br:8][C:5]1[N:4]=[C:3]2[N:9]([CH2:10][C@H:11]3[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12]3)[N:25]=[N:1][C:2]2=[N:7][CH:6]=1

Participants

Reactant 2

HCID 6228Dimethylformamide

HCID 118364866HCID 118364866, compound

Product 1

HCID 118364837HCID 118364837, compoundYield 62%

Conditions

Temperature: 70 °C

Procedure

(R)-tert-butyl 3-(((3-amino-6-bromopyrazine-2-yl)amino)methyl)piperidine-1-carboxylate (2.19 g, 5.70 mmol) was dissolved in DMF (15 ml), and then isoamylnitrile (0.92 ml, 6.84 mmol) was slowly dropped at 0° C. After that, the mixture was stirred at 70° C. for 1 hour. After the completion of the reaction, the reaction mixture was extracted with H2O, EA, and brine, followed by drying (Na2SO4), filtration, and concentration under reduced pressure, and the residue was purified by column chromatography (EA:Hex=1:8), to give (S)-tert-butyl 3-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)piperidine-1-carboxylate (1.39 g, 62%).

Workup

customAfter the completion of the reaction
extractionthe reaction mixture was extracted with H2O, EA, and brine
customby drying
filtration(Na2SO4), filtration, and concentration under reduced pressure
customthe residue was purified by column chromatography (EA:Hex=1:8)

Sources & evidence

ORD record: ord-225c0364a7334b0a8e6f3092820d79b4
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403831B2

Reaction notes

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