3-Chloro-4-fluorophenylhydrazine hydrochloride → 1-(3-Chloro-4-fluorophenyl)-5-(5-methoxypyridin-3-yl)-1H-pyrazole-3-carboxylic acid

HRID 930040Notes

Reaction equation

HRID 930040 reaction equation
[Li].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:10]([O-])=[CH:11][C:12](=O)[C:13]([O:15]CC)=[O:14])[CH:7]=[N:8][CH:9]=1.ClC1C=C(C2N(C3C=CC=CN=3)N=C(C(O)=O)C=2)C=C(F)C=1.Cl.[Cl:43][C:44]1[CH:45]=[C:46]([NH:51][NH2:52])[CH:47]=[CH:48][C:49]=1[F:50]>>[Cl:43][C:44]1[CH:45]=[C:46]([N:51]2[C:10]([C:6]3[CH:7]=[N:8][CH:9]=[C:4]([O:3][CH3:2])[CH:5]=3)=[CH:11][C:12]([C:13]([OH:15])=[O:14])=[N:52]2)[CH:47]=[CH:48][C:49]=1[F:50]

Participants

4

Reactant 3

HCID 441817773-Chloro-4-fluorophenylhydrazine hydrochlorideHCID 896025755-(3-Chloro-5-fluorophenyl)-1-(pyridin-2-yl)-1H-pyrazole-3-carboxylic acidHCID 131735141Lithium 1-(5-methoxypyridin-3-yl)-4-ethoxy-3,4-dioxobut-1-en-1-olate

Product 1

HCID 896024571-(3-Chloro-4-fluorophenyl)-5-(5-methoxypyridin-3-yl)-1H-pyrazole-3-carboxylic acid

Procedure

600 mg (1.33 mmol) of the compound of Example 16A is reacted analogously to the synthesis of the compound of Example 20A with 288 mg (1.46 mmol) of 3-chloro-4-fluorophenylhydrazine hydrochloride. After hydrolysis, the entire reaction mixture is reduced to the dry state i. vac. 712 mg (37% purity, 57% of theory) of the title compound, which is used without further purification, is obtained.

Workup

  1. customAfter hydrolysis
  2. customthe entire reaction mixture
  3. custom712 mg (37% purity, 57% of theory) of the title compound, which is used without further purification
  4. customis obtained

Sources & evidence

ORD record
ord-cd47ee6726794e81a15e818508a708a7
Source dataset
uspto-grants-2016_03
Patent number
US09296720B2

Reaction notes

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