Ethyl Acetate → HCID 79016219, compound

HRID 551883Notes

Reaction equation

HRID 551883 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[Br:10][C:11]1[N:12]=[C:13](Br)[C:14]2[N:15]([CH:17]=[CH:18][N:19]=2)[CH:16]=1.C(OCC)(=O)C>CN(C=O)C>[Br:10][C:11]1[N:12]=[C:13]([NH:1][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)[C:14]2[N:15]([CH:17]=[CH:18][N:19]=2)[CH:16]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 133964-AminobenzonitrileHCID 150258436,8-Dibromoimidazo[1,2-a]pyrazine

Product 1

HCID 79016219HCID 79016219, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 4-aminobenzonitrile (220 mg; 1.89 mmol) and 6,8-dibromo-imidazo[1,2-a]pyrazine (500 mg; 1.81 mmol) is slurried in DMF (1 mL) and heated to 140° C. for 20 minutes. The reaction is allowed to cool, and when the bath reaches 75° C., ethyl acetate (40 mL) is added and the slurry is stirred to break up large solid lumps into fine powder. The powdered 4-(6-bromo-imidazo[1,2-a]pyrazin-8-ylamino)-benzonitrile is filtered, washed with diethyl ether (2×50 mL) and dried under vacuum to a fine orange/tan solid (600 mg).

Workup

  1. temperatureto cool
  2. customreaches 75° C.
  3. filtrationThe powdered 4-(6-bromo-imidazo[1,2-a]pyrazin-8-ylamino)-benzonitrile is filtered
  4. washwashed with diethyl ether (2×50 mL)
  5. dry with materialdried under vacuum to a fine orange/tan solid (600 mg)

Sources & evidence

ORD record
ord-79122d051946401fb5ef7300ff027bd8
Source dataset
uspto-grants-2011_05
Patent number
US07947835B2

Reaction notes

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