Ammonia → HCID 22291565, compound

HRID 457303Notes

Reaction equation

HRID 457303 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([N:10]3[C:18]4[C:17]5[CH:19]=[C:20]([NH:23]C(C6C(Cl)=NC=CC=6)=O)[CH:21]=[CH:22][C:16]=5[CH2:15][CH2:14][C:13]=4[C:12]([C:33]([NH2:35])=[O:34])=[N:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.N>C(O)C>[NH2:23][C:20]1[CH:21]=[CH:22][C:16]2[CH2:15][CH2:14][C:13]3[C:12]([C:33]([NH2:35])=[O:34])=[N:11][N:10]([C:8]4[CH:7]=[CH:6][C:5]5[O:1][CH2:2][O:3][C:4]=5[CH:9]=4)[C:18]=3[C:17]=2[CH:19]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 10117126HCID 10117126, compound

Product 1

HCID 22291565HCID 22291565, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

The title product of Step 3 was dissolved in anhydrous ethanol and then an approximately equal volume of liquid ammonia was added. The resulting mixture was sealed in a pressure vessel and then stirred overnight at 100° C. After cooling, the mixture was concentrated. The residue was taken up in dichloromethane-methanol and chromatographed over silica gel using ethyl acetate as eluent to give the title compound, 890 mg, as an oil which crystallized on standing. Anal. for C19H16N4O3.0.75H2O (MW 361.87): Calc'd.: C, 63.06; H, 4.46, N, 15.48. Found: C, 63.24; H, 4.70, N, 14.58.

Workup

  1. customThe resulting mixture was sealed in a pressure vessel
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated
  4. customchromatographed over silica gel

Sources & evidence

ORD record
ord-5e8785ac5c6848dab44b749158134c72
Source dataset
uspto-grants-2007_03
Patent number
US07186743B2

Reaction notes

Loading…