Chloroform → HCID 70155363, compound

HRID 2257840Notes

Reaction equation

HRID 2257840 reaction equation
[CH2:1]([C@:3]1([OH:41])[C:38]2[CH:37]=[C:36]3[N:9]([CH2:10][C:11]4[C:12]3=[N:13][C:14]3[CH:15]=[CH:16][C:17]([F:35])=[C:18]5[CH:23]([N:24]6C(=O)C7C(=CC=CC=7)C6=O)[CH2:22][CH2:21][C:20]=4[C:19]=35)[C:8](=[O:39])[C:7]=2[CH2:6][O:5][C:4]1=[O:40])[CH3:2].O.NN.C(Cl)(Cl)[Cl:46]>CO>[ClH:46].[NH2:24][CH:23]1[C:18]2[C:19]3[C:20](=[C:11]4[CH2:10][N:9]5[C:36](=[CH:37][C:38]6[C@:3]([CH2:1][CH3:2])([OH:41])[C:4](=[O:40])[O:5][CH2:6][C:7]=6[C:8]5=[O:39])[C:12]4=[N:13][C:14]=3[CH:15]=[CH:16][C:17]=2[F:35])[CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 24654Hydrazine hydrate (1:1)HCID 70155248HCID 70155248, compound

Product 1

HCID 70155363HCID 70155363, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

120 mg of the compound prepared in (11) above was dissolved in a mixed solvent of 7 ml of chloroform and 5 ml of methanol. After the addition of 0.7 ml of hydrazine monohydrate, the mixture was heated under reflux for 1 hour. The reaction mixture was concentrated to dryness and to the residue was added 7 ml of 4N hydrochloric acid, and the mixture was heated under reflux for 1 hour. After concentration to dryness, 10 ml of water to the residue to remove the insoluble substances by filtration. The filtrate was purified in the same manner as in Example 7 to obtain 32 mg of Isomer A and 20 mg of Isomer B of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. concentrationThe reaction mixture was concentrated to dryness and to the residue
  4. additionwas added 7 ml of 4N hydrochloric acid
  5. temperaturethe mixture was heated
  6. temperatureunder reflux for 1 hour
  7. concentrationAfter concentration to dryness, 10 ml of water to the residue
  8. customto remove the insoluble substances
  9. filtrationby filtration
  10. customThe filtrate was purified in the same manner as in Example 7

Sources & evidence

ORD record
ord-5f351ff8dca74e7badd943fda16f6936
Source dataset
uspto-grants-1997_08
Patent number
US05658920

Reaction notes

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