Dimethylformamide → 5-[[bis(pyridin-3-ylmethyl)amino]methyl]-4-[(3,4-difluorophenyl)hydrazinylidene]pyrazol-3-amine

HRID 255012Notes

Reaction equation

HRID 255012 reaction equation
[NH2:1][CH2:2][C:3]1[C:4](=[N:9][NH:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[C:13]([F:18])[CH:12]=2)[C:5]([NH2:8])=[N:6][N:7]=1.C([N:21]([CH2:24][CH3:25])[CH2:22]C)C.Br[CH2:27][C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1.C(O[CH2:38][CH3:39])(=O)C.[CH3:40]N(C=O)C>>[N:30]1[CH:31]=[CH:32][CH:33]=[C:28]([CH2:27][N:1]([CH2:2][C:3]2[C:4](=[N:9][NH:10][C:11]3[CH:16]=[CH:15][C:14]([F:17])=[C:13]([F:18])[CH:12]=3)[C:5]([NH2:8])=[N:6][N:7]=2)[CH2:40][C:25]2[CH:24]=[N:21][CH:22]=[CH:38][CH:39]=2)[CH:29]=1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 2459343-(Bromomethyl)pyridineHCID 178510680HCID 178510680, compound

Product 1

HCID 1785091535-[[bis(pyridin-3-ylmethyl)amino]methyl]-4-[(3,4-difluorophenyl)hydrazinylidene]pyrazol-3-amine

Conditions

Temperature
76 °C

Procedure

A 2 mL suspension of 5-aminomethyl-4-[(3,4-difluorophenyl)hydrazono]-4H-pyrazol-3-ylamine (100 mg, 0.397 mmole) and triethylamine (120 μL, 0.86 mmole) was heated to 66° C. To this orange solution was added dropwise a solution of 3-bromomethylpyridine (110 mg, 0.43 mmole) in 1 mL of DMF. The reaction was stirred at 76° C. overnight, and then mixed with saline and ethyl acetate. The crude material was purified by prepreparative TLC (CH2Cl2:CH3OH=10:1) to yield 20 mg of the title compound as a yellow powder. MS (m/z, ES+): 435 (M+1, 73%), 94 (100%).

Workup

  1. customThe crude material was purified by prepreparative TLC (CH2Cl2:CH3OH=10:1)

Sources & evidence

ORD record
ord-331c19ffb241453e8e3908c313459706
Source dataset
uspto-grants-2011_01
Patent number
US07875728B2

Reaction notes

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