Diisopropylethylamine → HCID 86684126, compound

HRID 1024027Notes

Reaction equation

HRID 1024027 reaction equation
[Br:1][C:2]1[N:3]=[C:4](Br)[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1.C(N(C(C)C)CC)(C)C.[NH2:21][C:22]1[N:27]=[CH:26][C:25]([N:28]2[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]2)=[CH:24][CH:23]=1>CC(O)C>[Br:1][C:2]1[N:3]=[C:4]([NH:21][C:22]2[N:27]=[CH:26][C:25]([N:28]3[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]3)=[CH:24][CH:23]=2)[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 11737525tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylateHCID 150258436,8-Dibromoimidazo[1,2-a]pyrazine

Product 1

HCID 86684126HCID 86684126, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 6,8-dibromoimidazo[1,2-a]pyrazine (1.2 g, 4.3 mmol), diisopropylethylamine (1.1 g, 8 mmol), and tert-butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate (1 g, 3.5 mmol) in IPA (20 mL) was stirred at 130° C. under microwave irradiation for 1.5 h. The resulting suspension was filtered and the solid was washed with water and dried in vacuum to afford the crude product, which was further purified by silica gel chromatography eluting with CH2Cl2/MeOH (50:1) to afford 106a as a white solid (800 mg, 50%). MS: [M+H]+ 474.

Workup

  1. filtrationThe resulting suspension was filtered
  2. washthe solid was washed with water
  3. customdried in vacuum
  4. customto afford the crude product, which
  5. customwas further purified by silica gel chromatography
  6. washeluting with CH2Cl2/MeOH (50:1)

Sources & evidence

ORD record
ord-785c36aef1a8442e88cd85a06606f828
Source dataset
uspto-grants-2014_05
Patent number
US08722676B2

Reaction notes

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