Ethanol → HCID 52935321, compound

HRID 2075729Notes

Reaction equation

HRID 2075729 reaction equation
Cl[C:2]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][C:6]([S:18][C:19]3[CH:20]=[C:21]([C:25]([OH:30])([CH2:28][CH3:29])[CH2:26][CH3:27])[CH:22]=[CH:23][CH:24]=3)=[CH:7][CH:8]=2)[N:3]=1.[NH2:31][NH2:32].[CH3:33]CO>>[C:12]1([C:10]2[C:9]3[C:4](=[CH:5][C:6]([S:18][C:19]4[CH:20]=[C:21]([C:25]([OH:30])([CH2:28][CH3:29])[CH2:26][CH3:27])[CH:22]=[CH:23][CH:24]=4)=[CH:7][CH:8]=3)[N:3]3[CH:33]=[N:31][N:32]=[C:2]3[CH:11]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 9321HydrazineHCID 58257812HCID 58257812, compound

Product 1

HCID 52935321HCID 52935321, compound

Procedure

10n (200 mg, 0.46 mmol) was treated with anhydrous hydrazine (2 mL) in EtOH (2 mL) at 60° C. for 1 hour. The reaction was concentrated and diluted with CH2Cl2 and water. The organic layer was dried over MgSO4, filtered, and concentrated. The residue was then treated with ethyl orthoformate (2.5 mL) in EtOH (5 mL) at 65° C. overnight. The mixture was concentrated and diluted with EtOAc and water. The aqueous layer was extracted with EtOAc, and the combined organic layers were dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography to give the desired product, 10o. The hydrochloride salt was prepared by dissolving the product in CH2Cl2, adding 1N HCl in ether, and concentrating the mixture.

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with CH2Cl2 and water
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. additionThe residue was then treated with ethyl orthoformate (2.5 mL) in EtOH (5 mL) at 65° C. overnight
  7. concentrationThe mixture was concentrated
  8. additiondiluted with EtOAc and water
  9. extractionThe aqueous layer was extracted with EtOAc
  10. dry with materialthe combined organic layers were dried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-c37bf3871c3041139a385aea4591d6f8
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

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