Water → HCID 178432418, compound

HRID 536493Notes

Reaction equation

HRID 536493 reaction equation
Cl[C:2]1[N:9]=[C:8]([CH3:10])[C:7]([F:11])=[CH:6][C:3]=1[C:4]#[N:5].O.[NH2:13][NH2:14].C(N(C(C)C)CC)(C)C.O>C(O)CO.C(OCC)(=O)C>[F:11][C:7]1[CH:6]=[C:3]2[C:4]([NH2:5])=[N:14][NH:13][C:2]2=[N:9][C:8]=1[CH3:10]

Participants

7

Reactant 4

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 81531DiisopropylethylamineHCID 219283552-Chloro-5-fluoro-6-methylpyridine-3-carbonitrile

Product 1

HCID 178432418HCID 178432418, compound

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 8857Ethyl AcetateSolvent

Procedure

58 g (340.027 mmol) of 2-chloro-5-fluoro-6-methylnicotinonitrile (preparation described in WO2007/41052, example U-2, page 80) was put in 1,2-ethanediol (580 ml) and then hydrazine hydrate (24.813 ml) and 56.091 ml (340.027 mmol) of diisopropyl ethylamine were added. The reaction mixture was heated with stirring for 16 h to 80° C. and then for 66 h to 120° C. After cooling, water (2.5 l) and ethyl acetate (2.5 l) were added and it was filtered with suction. The solid obtained was dried. 28.4 g (47% of theor.) of the target compound was obtained.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureAfter cooling
  3. filtrationit was filtered with suction
  4. customThe solid obtained
  5. customwas dried
  6. custom28.4 g (47% of theor.) of the target compound was obtained

Sources & evidence

ORD record
ord-46d380f521344b89b61d1c4d5f3ef297
Source dataset
uspto-grants-2014_10
Patent number
US08859569B2

Reaction notes

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