Hydrazine hydrate (1:1) → [6-(1-Methyl-1H-pyrazol-4-yl)-pyrrolo[3,2-b]pyridin-1-yl]-acetic acid hydrazide

HRID 655265Notes

Reaction equation

HRID 655265 reaction equation
C(O[C:4](=[O:21])[CH2:5][N:6]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([C:15]3[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=3)[CH:13]=2)[CH:8]=[CH:7]1)C.O.[NH2:23][NH2:24]>C(O)C>[CH3:20][N:18]1[CH:19]=[C:15]([C:12]2[CH:13]=[C:14]3[N:6]([CH2:5][C:4]([NH:23][NH2:24])=[O:21])[CH:7]=[CH:8][C:9]3=[N:10][CH:11]=2)[CH:16]=[N:17]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 68704641[6-(1-Methyl-1H-pyrazol-4-yl)-pyrrolo[3,2-b]pyridin-1-yl]-acetic acid ethyl ester

Product 1

HCID 59320263[6-(1-Methyl-1H-pyrazol-4-yl)-pyrrolo[3,2-b]pyridin-1-yl]-acetic acid hydrazideYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

[6-(1-Methyl-1H-pyrazol-4-yl)-pyrrolo[3,2-b]pyridin-1-yl]-acetic acid ethyl ester (122 mg, 0.42 mmol) was dissolved in ethanol (1 mL) and hydrazine hydrate (500 uL). The solution was heated to reflux for 1 hour. Next the solution was concentrated down under vacuum and redissolved in a minimal amount of hot methanol. The product crystallized and was a collected by filtration to afford the title compound (114.8 mg, 99% yield). MS m/z=271 [M+H+]+

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 1 hour
  3. concentrationNext the solution was concentrated down under vacuum
  4. dissolutionredissolved in a minimal amount of hot methanol
  5. customThe product crystallized
  6. filtrationa collected by filtration

Sources & evidence

ORD record
ord-c66f8ba4bfa04c5aaea82443fbc9aa15
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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