Chloroform → HCID 70155363, compound

HRID 355957Notes

Reaction equation

HRID 355957 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-ff5e6aa53d84464ab1d2ac9d8bedfb8d
Source dataset
uspto-grants-1998_11
Patent number
US05834476

Reaction notes

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