Triethylamine → HCID 178432596, compound

HRID 570535Notes

Reaction equation

HRID 570535 reaction equation
[F:1][C:2]1[C:21]([F:22])=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([CH3:14])=[N:12][CH:13]=[C:8]2[C:7]([C:15](=[NH:17])[NH2:16])=[N:6]1.C([N:25](CC)CC)C.O.NN>C(O)C>[F:1][C:2]1[C:21]([F:22])=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([CH3:14])=[N:12][CH:13]=[C:8]2[C:7]([C:15](=[NH:16])[NH:17][NH2:25])=[N:6]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 866921001-(2,3-Difluorobenzyl)-6-methyl-1H-pyrazolo[3,4-d]pyrimidine-3-carboximidamide

Product 1

HCID 178432596HCID 178432596, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Under an argon atmosphere, 440 mg (1.237 mmol, purity 85%) of 1-(2,3-difluorobenzyl)-6-methyl-1H-pyrazolo[3,4-d]pyrimidine-3-carboximidamide were initially charged in 6 ml of ethanol and cooled to 0° C. 500 mg (4.49 mmol) of triethylamine and 85 mg (1.361 mmol) of 80% hydrazine hydrate were added, and the mixture was stirred at room temperature for 72 h. The mixture was concentrated on a rotary evaporator, taken up in ethyl acetate and washed three times with saturated aqueous sodium chloride solution. The organic phase was dried over sodium sulphate, concentrated on a rotary evaporator and dried under high vacuum. 421 mg (purity 84%, 90% of theory) of the target compound were obtained.

Workup

  1. concentrationThe mixture was concentrated on a rotary evaporator
  2. washwashed three times with saturated aqueous sodium chloride solution
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. concentrationconcentrated on a rotary evaporator
  5. customdried under high vacuum
  6. custom421 mg (purity 84%, 90% of theory) of the target compound were obtained

Sources & evidence

ORD record
ord-812f5fc7612e4eefb56266be4b22b418
Source dataset
uspto-grants-2015_05
Patent number
US09023849B2

Reaction notes

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