Hydrazine hydrate (1:1) → HCID 136414045, compound

HRID 1622398Notes

Reaction equation

HRID 1622398 reaction equation
Cl([O-])(=O)(=O)=O.[CH2:6]([C:8]1[C:12]2[C:13]([F:17])=[CH:14][CH:15]=[CH:16][C:11]=2[S:10][C:9]=1[C:18]1[C:30]2[C:22](=[CH:23][C:24]3[NH:25][C:26](=[O:31])[O:27][C:28]=3[CH:29]=2)[CH:21]=[C:20]([CH3:32])[O+]=1)[CH3:7].C(C1C2C(F)=CC=CC=2SC=1C=O)C.O.[NH2:48][NH2:49]>CC(O)C>[CH2:6]([C:8]1[C:12]2[C:13]([F:17])=[CH:14][CH:15]=[CH:16][C:11]=2[S:10][C:9]=1[C:18]1[C:30]2[CH:29]=[C:28]3[O:27][C:26](=[O:31])[NH:25][C:24]3=[CH:23][C:22]=2[CH2:21][C:20]([CH3:32])=[N:49][N:48]=1)[CH3:7]

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 86670551HCID 86670551, compoundHCID 178435438HCID 178435438, compound

Product 1

HCID 136414045HCID 136414045, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a suspension of 5-(3-ethyl-4-fluoro-1-benzothien-2-yl)-7-methyl-2-oxo-1H,2H-isochromeno[6,7-d][1,3]oxazol-6-ium perchlorate (51 mmol) (obtained according to Steps A and B described in Example 1 using 3-ethyl-4-fluoro-1-benzothiophene-2-carbaldehyde instead of 2-naphthaldehyde) in 2-propanol (468 mL) there is added hydrazine hydrate (6.68 mL; 133 mmol), with vigorous stirring, at ambient temperature. The reaction mixture is stirred for 20 hours at ambient temperature. The crystals obtained are then filtered off and then stirred in warm water (1900 mL) for 30 minutes. After filtration and drying, the solid is purified by chromatography over a silica gel column (eluant: dichloromethane/acetonitrile) to yield the title product.

Workup

  1. customobtained
  2. customat ambient temperature
  3. customThe crystals obtained
  4. filtrationare then filtered off
  5. stirringstirred in warm water (1900 mL) for 30 minutes
  6. filtrationAfter filtration
  7. customdrying
  8. customthe solid is purified by chromatography over a silica gel column (eluant: dichloromethane/acetonitrile)

Sources & evidence

ORD record
ord-250ab37d99324039a190507166c38c6d
Source dataset
uspto-grants-2014_07
Patent number
US08778932B2

Reaction notes

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