Butyl isocyanate → N-Butyl-N'-(3-phenylimidazo[1,2-a]pyrazin-8-yl)urea

HRID 1371371Notes

Reaction equation

HRID 1371371 reaction equation
[C:1]1([C:7]2[N:11]3[CH:12]=[CH:13][N:14]=[C:15]([NH2:16])[C:10]3=[N:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:17]([N:21]=[C:22]=[O:23])[CH2:18][CH2:19][CH3:20]>C(Cl)Cl.CN(C=O)C.C1COCC1.CCOC(C)=O>[CH2:17]([NH:21][C:22]([NH:16][C:15]1[C:10]2[N:11]([C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:8][N:9]=2)[CH:12]=[CH:13][N:14]=1)=[O:23])[CH2:18][CH2:19][CH3:20]

Participants

7

Reactant 2

HCID 8110Butyl isocyanateHCID 113901833-phenyl-imidazo[1,2-a]pyrazin-8-ylamine

Product 1

HCID 21070839N-Butyl-N'-(3-phenylimidazo[1,2-a]pyrazin-8-yl)ureaYield 36%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 3-phenyl-imidazo[1,2-a]pyrazin-8-ylamine (Example 11) (28 mg, 0.133 mmol) in DCM (0.5 ml), DMF (1 ml) and THF (0.5 ml) was added butyl isocyanate (0.03 ml, 2 eq.). The mixture was heated at 60° C. for 8 hr. After cooling to rt, the mixture was diluted with EtOAc. The organic layer was washed with brine, dried and concentrated. The residue was purified on a silica gel column to give 15 mg (yield 36%) of the title compound.

Workup

  1. temperatureAfter cooling to rt
  2. washThe organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-2a3014effe5d4e01841e7290d250bd91
Source dataset
uspto-grants-2007_01
Patent number
US07157460B2

Reaction notes

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