Ammonia → HCID 22291565, compound

HRID 968099Notes

Reaction equation

HRID 968099 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 C19H16N4O3.0.75 H2O (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-8dba19335a6c4063b20070ed3bef8dcb
Source dataset
uspto-grants-2005_10
Patent number
US06956052B2

Reaction notes

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