Hydrazine → HCID 178434380, compound

HRID 1508006Notes

Reaction equation

HRID 1508006 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[N:18][C:17]([C:20](=O)[CH3:21])=[C:16](Cl)[N:15]=2)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:25][NH2:26]>CC(O)C.O>[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:15]=[C:16]3[NH:25][N:26]=[C:20]([CH3:21])[C:17]3=[N:18][CH:19]=2)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 9321HydrazineHCID 86678951HCID 86678951, compound

Product 1

HCID 178434380HCID 178434380, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
120 °C

Procedure

[4-(5-Acetyl-6-chloro-pyrazin-2-yl)-phenyl]-carbamic acid tert-butyl ester (2.18 g) was suspended in a mixture of 21 ml iPrOH and 21 ml 35% hydrazine in water at RT and heated to 120° C. by microwave irradiation for 20 min under stirring in a sealed vessel. The reaction mixture was left to cool to RT, quenched with a saturated aqueous sodium bicarbonate solution (10 ml) and extracted with EtOAc (3×30 ml). The combined organic phases were dried over sodium sulfate, filtered and evaporated to afford the crude product. Purification by trituration in boiling EtOAc and subsequent filtration afforded [4-(3-methyl-1H-pyrazolo[3,4-b]pyrazin-6-yl)-phenyl]-carbamic acid tert-butyl ester as a yellow solid. Yield: 1.42 g (70%).

Workup

  1. waitThe reaction mixture was left
  2. temperatureto cool to RT
  3. customquenched with a saturated aqueous sodium bicarbonate solution (10 ml)
  4. extractionextracted with EtOAc (3×30 ml)
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto afford the crude product
  9. customPurification by trituration
  10. filtrationEtOAc and subsequent filtration

Sources & evidence

ORD record
ord-03b816a94f244a51a7dbd13f8744a76e
Source dataset
uspto-grants-2015_12
Patent number
US09221828B2

Reaction notes

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