Nitrogen → HCID 22291568, compound

HRID 968135Notes

Reaction equation

HRID 968135 reaction equation
ClC1C=CC=CC=1C(NC1C=CC2CCC3C(C(N)=O)=[N:15][N:16]([C:18]4[CH:23]=[CH:22][C:21]([S:24]([CH:27]([CH3:29])[CH3:28])(=[O:26])=[O:25])=[CH:20][CH:19]=4)C=3C=2C=1)=O.N#N.NN>C(O)C>[CH:27]([S:24]([C:21]1[CH:22]=[CH:23][C:18]([NH:16][NH2:15])=[CH:19][CH:20]=1)(=[O:26])=[O:25])([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 947NitrogenHCID 9321Hydrazine2×HCID 222919678-[(2-Chlorobenzoyl)amino]-4,5-dihydro-1-[4-[(1-methylethyl)sulfonyl]phenyl]-1H-benz[g]indazole-3-carboxamide

Product 1

HCID 22291568HCID 22291568, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product of step 1 (640 mg, 3.15 mmol) was dissolved in absolute ethanol (12 mL), the system was flushed with N2 and hydrazine (404 mg, 12.6 mmol) was added and the reaction refluxed overnight. HPLC showed 78% product and 21% starting material. To drive the reaction to completion 2 equivalents of additional hydrazine was added and reaction was refluxed for additional 5 hours, at this time HPLC indicated 95% product. The reaction mixture was concentrated and the residue was stirred with water. A white solid, 390 mg (58%) was isolated. HPLC indicated 86% product and 14% starting material. The aqueous phase was extracted with ethyl acetate (3×50 mL). The organic phase was dried over MgSO4, and concentrated to yield 258 mg (38%) of 1-[4-(isopropylsulfonyl)phenyl]hydrazine with 99% purity. MH+=215. The 390 mg was re-dissolved in 10 mL ethanol and treated once more with additional hydrazine to obtain additional product with the desired purity.

Workup

  1. additionwas added
  2. temperaturethe reaction refluxed overnight
  3. additionwas added
  4. customreaction
  5. temperaturewas refluxed for additional 5 hours, at this time HPLC
  6. concentrationThe reaction mixture was concentrated
  7. customA white solid, 390 mg (58%) was isolated
  8. extractionThe aqueous phase was extracted with ethyl acetate (3×50 mL)
  9. dry with materialThe organic phase was dried over MgSO4
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-f1a893f064b24a1fb419ab8d351d467a
Source dataset
uspto-grants-2005_10
Patent number
US06956052B2

Reaction notes

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