Methylhydrazine → HCID 445990, compound

HRID 342223Notes

Reaction equation

HRID 342223 reaction equation
[CH3:1][NH:2][NH2:3].C(=O)([O-])[O-].[K+].[K+].[CH2:10]([N:13]([CH3:36])[CH2:14]/[CH:15]=[CH:16]/[CH2:17][O:18][C:19]1[C:24]([F:25])=[CH:23][C:22]([C:26]([C:28]2[CH:33]=[CH:32][C:31]([Br:34])=[CH:30][CH:29]=2)=O)=[C:21](F)[CH:20]=1)[CH:11]=[CH2:12]>CC(N(C)C)=O>[CH2:10]([N:13]([CH2:14]/[CH:15]=[CH:16]/[CH2:17][O:18][C:19]1[CH:20]=[C:21]2[C:22]([C:26]([C:28]3[CH:33]=[CH:32][C:31]([Br:34])=[CH:30][CH:29]=3)=[N:3][N:2]2[CH3:1])=[CH:23][C:24]=1[F:25])[CH3:36])[CH:11]=[CH2:12]

Participants

5

Reactant 3

HCID 6061MethylhydrazineHCID 11430Potassium CarbonateHCID 18434106HCID 18434106, compound

Product 1

HCID 445990HCID 445990, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

A mixture of 0.53 ml of methyl hydrazine and 0.17 g of potassium carbonate is stirred in 5 ml of DMA at room temperature. After the addition of 0.44 g of (E)-[4-[4-(allyl-methyl-amino)-but-2-enyloxy]-2,5-difluoro-phenyl]-(4-bromo-phenyl)-methanone in 5 ml of DMA the mixture is boiled at 120° C. After filtration the filtrate is concentrated at 80° C./0.3 Torr, taken up in methylene chloride, filtered over sodium sulphate and concentrated. The residue consisting of the title compound is dissolved in ether/hexane, treated with 0.11 g of fumaric acid and stirred. After filtration and drying there is obtained 0.41 g of (E)-allyl-[4-[3-(4-bromo-phenyl)-5-fluoro-1-methyl-1H-indazol-6-yloxy]-but-2-enyl]-methyl-amine.fumarate, m.p. 135°-137° C.

Workup

  1. filtrationAfter filtration the filtrate
  2. concentrationis concentrated at 80° C./0.3 Torr
  3. filtrationfiltered over sodium sulphate
  4. concentrationconcentrated
  5. dissolutionis dissolved in ether/hexane
  6. additiontreated with 0.11 g of fumaric acid
  7. filtrationAfter filtration
  8. customdrying there

Sources & evidence

ORD record
ord-b7b9546a7d3846fca7b5e60862bc89c8
Source dataset
uspto-grants-1999_01
Patent number
US05856503

Reaction notes

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