Hydrazine → HCID 178437995, compound

HRID 2074486Notes

Reaction equation

HRID 2074486 reaction equation
F[C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=O)=[CH:4][C:3]=1[C:11](=O)[CH2:12][CH3:13].[NH2:15][NH2:16].O=P(Cl)(Cl)Cl.[NH2:22][NH:23][C:24]([NH2:26])=[S:25]>>[CH2:12]([C:11]1[C:3]2[C:2](=[CH:10][CH:9]=[C:5]([C:6]3[S:25][C:24]([NH2:26])=[N:23][N:22]=3)[CH:4]=2)[NH:16][N:15]=1)[CH3:13]

Participants

5

Reactant 4

HCID 9321HydrazineHCID 24813Phosphorus oxychlorideHCID 2723789ThiosemicarbazideHCID 59694496HCID 59694496, compound

Product 1

HCID 178437995HCID 178437995, compound

Procedure

4-Fluoro-3-propionylbenzoic acid was synthesized by treating the commercial available 3-bromo-4-fluorobenzoic acid with 1-ethoxyprop-1-ene (6 equivalents), palladium acetate (0.03 equivalents), 1,3-Bis-(diphenylphosphino)-propane (0.06 equivalents) and potassium carbonate (1.2 equivalents) in DMF and water under microwave at 130° C. for 3 hours following with an acid treatment. 3-Ethyl-1H-indazole-5-carboxylic acid was obtained by treating 4-Fluoro-3-propionylbenzoic acid with hydrazine under microwave at 160° C. for half an hour. 5-(3-ethyl-1H-indazol-5-yl)-1,3,4-thiadiazol-2-amine was prepared in a manner similar to that shown in scheme 3 with POCl3 and thiosemicarbazide. MS (API-ES) m/z (%): 246 (100%, M++1).

Sources & evidence

ORD record
ord-20dc3504ab09426bb3afc805866c0408
Source dataset
uspto-grants-2011_04
Patent number
US07919514B2

Reaction notes

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