Hydrazine hydrate (1:1) → HCID 178439341, compound

HRID 381318Notes

Reaction equation

HRID 381318 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([C:26]3[C:34]4[C:29](=[CH:30][C:31]([C:35]([NH2:37])=O)=[CH:32][CH:33]=4)[N:28]([CH3:38])[CH:27]=3)[C:11]([NH:13][S:14]([C:17]3[CH:22]=[CH:21][C:20]([CH:23]([CH3:25])[CH3:24])=[CH:19][CH:18]=3)(=[O:16])=[O:15])=[O:12])=[CH:9][C:4]=2[O:3][CH2:2]1.O.[NH2:40]N.COC(OC)[N:45]([CH3:47])C>>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([C:26]3[C:34]4[C:29](=[CH:30][C:31]([C:35]5[NH:37][CH:47]=[N:45][N:40]=5)=[CH:32][CH:33]=4)[N:28]([CH3:38])[CH:27]=3)[C:11]([NH:13][S:14]([C:17]3[CH:22]=[CH:21][C:20]([CH:23]([CH3:24])[CH3:25])=[CH:19][CH:18]=3)(=[O:15])=[O:16])=[O:12])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 78373Dimethylformamide dimethyl acetalHCID 22467235HCID 22467235, compound

Product 1

HCID 178439341HCID 178439341, compound

Procedure

Dimethylformamide dimethylacetal (10 ml) was added to 3-{1-(1,3-benzodioxol-5-yl)-2-[(4-isopropylphenyl)sulfonamido]-2-oxoethyl}-1-methyl-1H-6-indolecarboxamide (the compound of Example 28, 180 mg, 0.36 mmol) and the slurry was heated at reflux for 48 h. The solvent was removed in vacuo and the residue redissolved in glacial acetic acid (8 ml). Hydrazine hydrate (12 mg, 4.68 mmol) was added and the solution heated at reflux for 24 h. After cooling the crude product was extracted from brine (50 ml) with ethyl acetate (2×50 ml). The organic layers were dried (MgSO4) and concentrated. Flash column chromatography (elution with 96% dichloromethane/4% methanol) gave the desired product as a pale yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 48 h
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue redissolved in glacial acetic acid (8 ml)
  5. temperaturethe solution heated
  6. temperatureat reflux for 24 h
  7. extractionwas extracted from brine (50 ml) with ethyl acetate (2×50 ml)
  8. dry with materialThe organic layers were dried (MgSO4)
  9. concentrationconcentrated
  10. washFlash column chromatography (elution with 96% dichloromethane/4% methanol)

Sources & evidence

ORD record
ord-abd8aaf57a6147c89a5b6dd94e821bed
Source dataset
uspto-grants-2001_10
Patent number
US06306852B1

Reaction notes

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