Triethylamine → N-[[5-amino-4-[(3,4-difluorophenyl)hydrazinylidene]pyrazol-3-yl]methyl]pyridine-3-carboxamide

HRID 255011Notes

Reaction equation

HRID 255011 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(CC)CC)C.[C:26](Cl)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[N:29][CH:28]=1.C(OCC)(=O)C>CN(C=O)C>[NH2:8][C:5]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:3]([CH2:2][NH:1][C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[N:29][CH:28]=2)=[N:7][N:6]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 82604Nicotinoyl chlorideHCID 178510680HCID 178510680, compound

Product 1

HCID 178509155N-[[5-amino-4-[(3,4-difluorophenyl)hydrazinylidene]pyrazol-3-yl]methyl]pyridine-3-carboxamideYield 34.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 5-aminomethyl-4-[(3,4-difluorophenyl)hydrazono]-4H-pyrazol-3-ylamine (245 mg, 0.97 mmole) and triethylamine (202 mg, 2 mmole) in 10 mL of anhydrous DMF was added nicotinoyl chloride (178 mg, 1.0 mmol) in 7 mL of anhydrous DMF. The reaction was stirred at ambient temperature for 1 hour, and then mixed with saline and ethyl acetate. The title compound was purified by column chromatography (CH2Cl2:CH3OH=13:1) to yield 119 mg of the title compound as a yellow powder. MS (m/z, ES−): 356 (M−1, 20%); 1H NMR (ppm, 400 MHz, DMSO-d6) □δ 11.86 (br s, 1H), 9.04 (brs, 1H), 9.01 (s, 1H), 8.67 (d, 1H), 8.19 (d, 1H), 7.71 (dd, 1H), 7.57 (m, 1H), 7.47 (m, 2H), 7.11 (br s, 2H), 4.69 (s, 2H).

Workup

  1. customThe title compound was purified by column chromatography (CH2Cl2:CH3OH=13:1)

Sources & evidence

ORD record
ord-f013aac9b63342538f4b990d1e3ef8d3
Source dataset
uspto-grants-2011_01
Patent number
US07875728B2

Reaction notes

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