HCID 118185271, compound → HCID 118185270, compound

HRID 928683Notes

Reaction equation

HRID 928683 reaction equation
[O:1]1[CH2:4][CH:3]([N:5]2[CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([N:17]([C:25]4[C:26]5[N:27]([CH:44]=[CH:45][N:46]=5)[CH:28]=[C:29]([Sn](CCCC)(CCCC)CCCC)[N:30]=4)[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:13][CH:12]=3)[CH2:7][CH2:6]2)[CH2:2]1.[C:47]([O:51][C:52]([N:54]([C:63]([O:65][C:66]([CH3:69])([CH3:68])[CH3:67])=[O:64])[C:55]1[C:60]([Cl:61])=[N:59][CH:58]=[C:57](Br)[N:56]=1)=[O:53])([CH3:50])([CH3:49])[CH3:48]>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:47]([O:51][C:52]([N:54]([C:55]1[C:60]([Cl:61])=[N:59][CH:58]=[C:57]([C:29]2[N:30]=[C:25]([N:17]([C:18]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:24])[C:14]3[CH:15]=[CH:16][C:11]([N:8]4[CH2:7][CH2:6][N:5]([CH:3]5[CH2:2][O:1][CH2:4]5)[CH2:10][CH2:9]4)=[CH:12][CH:13]=3)[C:26]3[N:27]([CH:44]=[CH:45][N:46]=3)[CH:28]=2)[N:56]=1)[C:63](=[O:64])[O:65][C:66]([CH3:69])([CH3:68])[CH3:67])=[O:53])([CH3:50])([CH3:49])[CH3:48]

Participants

5

Reactant 2

HCID 118185271HCID 118185271, compoundHCID 131735062HCID 131735062, compound

Product 1

HCID 118185270HCID 118185270, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 4-(4-(Oxetan-3-yl)piperazin-1-yl)phenyl(6-(tributylstannyl)imidazo[1,2-a]pyrazin-8-yl)carbamate V (1000 mg, 1.4 mmol), 2-Bis(tert-butoxycarbonyl)amino-6-bromo-3-chloropyrazine XI (552 mg, 1.35 mmol), and PdCl2(PPh3)2 (142.77 mg, 0.20 mmol), in 1,4-Dioxane (11.27 ml) was irridated in the microwave for 20 min at 140° C. The reaction was absorbed onto celite and eluted off a 40 g Gold Isco column using 0-10-100% (30% MeOH/DCM) over 20 column volumes. Fractions 34-39 were collected and concentrated. According to NMR, the title compound XII was identified and isolated.

Workup

  1. customThe reaction was absorbed onto celite
  2. washeluted off a 40 g Gold Isco column
  3. customFractions 34-39 were collected
  4. concentrationconcentrated
  5. customisolated

Sources & evidence

ORD record
ord-bf7a6b8f00764e0ea0122f53cbc31379
Source dataset
uspto-grants-2016_03
Patent number
US09290505B2

Reaction notes

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