Hydrazine hydrate (1:1) → HCID 9907490, compound

HRID 1838393Notes

Reaction equation

HRID 1838393 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:17]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[C:8]2=[N:9][CH:10]=[C:11]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:12]=[C:7]2[CH:6]=1)=O.O.[NH2:27][NH2:28]>C(O)C>[F:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][N:17]2[C:8]3=[N:9][CH:10]=[C:11]([S:13]([CH3:16])(=[O:14])=[O:15])[CH:12]=[C:7]3[CH:6]=[C:5]2[C:3]2[O:2][CH:1]=[N:27][N:28]=2)=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)3×HCID 68444621HCID 68444621, compound

Product 1

HCID 9907490HCID 9907490, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-(4-fluorobenzyl)-5-methanesulfonyl-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid methyl ester obtained in Example 33 (5) (0.3 g) in ethanol (9 ml), hydrazine monohydrate (0.22 g) was added at 15 to 30° C. and the mixture was heated under reflux for 6 hours, followed by further addition of hydrazine monohydrate (0.11 g), and the mixture was heated under reflux for 4 hours. Furthermore, hydrazine monohydrate (0.11 g) was added to the mixture, followed by heating under reflux for 16 hours. The reaction solution was concentrated under reduced pressure. To the resulting crude product was added orthoformic acid triethyl ester (25 ml) and the mixture was heated under reflux for 18 hours. The reaction solution was separated using silica gel column chromatography (ethyl acetate:hexane=1:1) to obtain 220 mg of the desired product.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 6 hours
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 4 hours
  5. temperatureby heating
  6. temperatureunder reflux for 16 hours
  7. concentrationThe reaction solution was concentrated under reduced pressure
  8. additionTo the resulting crude product was added orthoformic acid triethyl ester (25 ml)
  9. temperaturethe mixture was heated
  10. temperatureunder reflux for 18 hours
  11. customThe reaction solution was separated

Sources & evidence

ORD record
ord-74f4a587d72b4f919255b8d29cf2e165
Source dataset
uspto-grants-2004_01
Patent number
US06673797B1

Reaction notes

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