Hydrazine hydrate (1:1) → 3-(2-(5-Bromo-3-phenoxypyridin-2-ylamino)thiazol-4-yl)propanehydrazide

HRID 335201Notes

Reaction equation

HRID 335201 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][CH2:15][C:16](OC)=[O:17])[N:13]=2)=[N:6][CH:7]=1.O.[NH2:28][NH2:29]>CCO>[Br:1][C:2]1[CH:3]=[C:4]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][CH2:15][C:16]([NH:28][NH2:29])=[O:17])[N:13]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86631509Methyl 3-(2-(5-bromo-3-phenoxypyridin-2-ylamino)thiazol-4-yl)propanoate

Product 1

HCID 866315133-(2-(5-Bromo-3-phenoxypyridin-2-ylamino)thiazol-4-yl)propanehydrazideYield 83.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

To a mixture of methyl 3-(2-(5-bromo-3-phenoxypyridin-2-ylamino)thiazol-4-yl)propanoate (1.00 g, 2.303 mmol) (Example 315) in 15 mL EtOH was added hydrazine monohydrate (8.835 mL, 11.51 mmol) and the mixture heated at 75° C. for 4 hours. The reaction was cooled to ambient temperature and quenched with water and the solids were filtered to give the title compound (0.831 g, 83.10% yield) as off white solids there were used without further purification.

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. customquenched with water
  3. filtrationthe solids were filtered

Sources & evidence

ORD record
ord-06e3c2b3198144e2ac0d7c9fce89c628
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

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