Hydrochloric Acid → (3-amino-1H-indazol-5-yl)(3,5-difluorophenyl)Methanone

HRID 571890Notes

Reaction equation

HRID 571890 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([F:19])[CH:18]=1)[C:5]([C:7]1[CH:8]=[CH:9][C:10](F)=[C:11]([CH:14]=1)[C:12]#[N:13])=[O:6].O.[NH2:21][NH2:22].Cl>O1CCCC1>[NH2:13][C:12]1[C:11]2[C:10](=[CH:9][CH:8]=[C:7]([C:5]([C:4]3[CH:3]=[C:2]([F:1])[CH:18]=[C:17]([F:19])[CH:16]=3)=[O:6])[CH:14]=2)[NH:22][N:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 686714725-(3,5-Difluorobenzoyl)-2-fluorobenzonitrile

Product 1

HCID 68670985(3-amino-1H-indazol-5-yl)(3,5-difluorophenyl)Methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-(3,5-difluoro-benzoyl)-2-fluoro-benzonitrile (2.05 g, 7.84 mmol) and hydrazine hydrate (0.73 mL, 15.7 mmol) in dry tetrahydrofuran (100 mL) was stirred at room temperature for 2 hours. The reaction mixture was treated with 37% hydrochloric acid (1.3 mL, 15.7 mmol) for 30 min and then the volatiles were partially evaporated. The reaction mixture was then diluted with water (100 mL) and aqueous NH3 was added to reach neutral pH. The resulting solid was filtered, washed thoroughly with water and dried under vacuum at 60° C. The title compound was obtained as yellow solid (1.75 g, 80% yield).

Workup

  1. customthe volatiles were partially evaporated
  2. additionThe reaction mixture was then diluted with water (100 mL) and aqueous NH3
  3. additionwas added
  4. filtrationThe resulting solid was filtered
  5. washwashed thoroughly with water
  6. customdried under vacuum at 60° C

Sources & evidence

ORD record
ord-544918fa10994e45b4600d647724d283
Source dataset
uspto-grants-2015_05
Patent number
US09029356B2

Reaction notes

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