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1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 54671227, compound

HRID 869046
Notes
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Reaction equation

HRID 869046 reaction equation
Br[C:2]1[C:3]([NH2:20])=[N:4][CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[N:7]=1.[C:21]([C:23]1[N:28]=[C:27]([NH2:29])[CH:26]=[CH:25][CH:24]=1)#[CH:22].C1CCN2C(=NCCC2)CC1>C(#N)C.[Pd]>[NH2:29][C:27]1[N:28]=[C:23]([C:21]#[C:22][C:2]2[C:3]([NH2:20])=[N:4][CH:5]=[C:6]([C:8]3[CH:13]=[CH:12][C:11]([S:14]([CH:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[CH:10][CH:9]=3)[N:7]=2)[CH:24]=[CH:25][CH:26]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 450797916-Ethynylpyridin-2-amineHCID 580843723-Bromo-5-(4-(isopropylsulfonyl)phenyl)pyrazin-2-amine

Product 1

HCID 54671227HCID 54671227, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst
HCID 6342
Acetonitrile
Solvent

Conditions

Temperature
100 °C

Procedure

3-bromo-5-(4-(isopropylsulfonyl)phenyl)pyrazin-2-amine (75 mg, 0.2105 mmol), 6-ethynylpyridin-2-amine (29.84 mg, 0.2526 mmol), Pd EnCat 30 (33.68 mg, 0.01347 mmol) and DBU (70.50 mg, 69.25 μL, 0.4631 mmol) were combined in acetonitrile (1.500 mL). The reaction mixture was heated at 100° C. under microwave conditions for 1.5 hours. After this time the solid residue was removed by filtration and the filtrate concentrated in vacuo. The residue was purified by column chromatography (ISCO Companion™, 12 g column, eluting with 0 to 100% EtOAc/Petroleum Ether to 10% MeOH/DCM) to give the titled product as a beige solid (21 mg, 26% Yield). 1H NMR (400.0 MHz, DMSO) δ 1.18 (d, 6H), 3.45 (sept, 1H), 6.20 (s, 2H), 6.52 (d, 1H), 7.06 (d, 1H), 7.07 (br s, 2H), 7.45 (dd, 1H), 7.90 (d, 2H), 8.25 (d, 2H) and 8.78 (s, 1H) ppm; MS (ES+) 394.1.

Workup

  1. customAfter this time the solid residue was removed by filtration
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe residue was purified by column chromatography (ISCO Companion™, 12 g column, eluting with 0 to 100% EtOAc/Petroleum Ether to 10% MeOH/DCM)

Sources & evidence

ORD record
ord-6991d3d164384fbd9565a982b34f6c2b
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08969356B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes