Triethylamine → HCID 178512733, compound

HRID 1529166Notes

Reaction equation

HRID 1529166 reaction equation
[CH:1]1([CH2:6][N:7]2[C:11]3=[N:12][CH:13]=[C:14]([F:16])[CH:15]=[C:10]3[C:9]([C:17](=[NH:19])[NH2:18])=[N:8]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C([N:22](CC)CC)C.O.NN>C(O)C>[CH:1]1([CH2:6][N:7]2[C:11]3=[N:12][CH:13]=[C:14]([F:16])[CH:15]=[C:10]3[C:9]([C:17](=[NH:18])[NH:19][NH2:22])=[N:8]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 867151701-(cyclopentylmethyl)-5-fluoro-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide

Product 1

HCID 178512733HCID 178512733, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

1.400 g (5.358 mmol) of 1-(cyclopentylmethyl)-5-fluoro-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide were initially charged in 26 ml of ethanol, and the mixture was cooled to 0° C. 2.169 g (21.431 mmol) of triethylamine and 335 mg (5.358 mmol) of 80% strength hydrazine hydrate were added, and the mixture was stirred at room temperature for 18 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 sulfate, concentrated on a rotary evaporator and dried under high vacuum. This gave 1.070 g (purity 77%, 56% of theory) of the target compound.

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 sulfate
  4. concentrationconcentrated on a rotary evaporator
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-990a9959b1614be9b0fdbfab52575296
Source dataset
uspto-grants-2015_07
Patent number
US09090610B2

Reaction notes

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