Pyridine, 3-(4-aminopyrazol-1-yl)- → HCID 67499148, compound

HRID 1484724Notes

Reaction equation

HRID 1484724 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH:11]=[C:10]([NH2:12])[CH:9]=[N:8]2)[CH:2]=1.[F:13][C:14]([F:22])([F:21])[CH2:15][CH:16]([CH3:20])[C:17](O)=[O:18].Cl.CN(C)CCCN=C=NCC>ClC(Cl)C>[F:13][C:14]([F:22])([F:21])[CH2:15][CH:16]([CH3:20])[C:17]([NH:12][C:10]1[CH:9]=[N:8][N:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH:11]=1)=[O:18]

Participants

5

Reactant 3

HCID 206682Pyridine, 3-(4-aminopyrazol-1-yl)-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27755364,4,4-Trifluoro-2-methylbutanoic acid

Product 1

HCID 67499148HCID 67499148, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 1-(pyridin-3-yl)-1H-pyrazol-4-amine (0.150 g, 0.93 mmol) in dichloroethane (1.8 ml) was added 4,4,4-trifluoro-2-methylbutanoic acid (0.14 g, 0.93 mmol) and 4-N,N-dimethylaminopyridine (0.23 g, 1.87 mmol) followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.36 g, 1.87 mmol). The reaction stirred at room temperature overnight. The reaction mixture was concentrated and the crude product was purified by silica gel chromatography eluting with 0-5% MeOH/dichloromethane to give a white solid (0.15 g, 55%); mp 140-145° C.; 1H NMR (400 MHz, CDCl3) δ 9.00 (d, J=2.4 Hz, 1H), 8.62-8.47 (m, 2H), 8.01 (ddd, J=8.3, 2.7, 1.5 Hz, 1H), 7.68 (s, 1H), 7.53 (bs, 1H), 7.40 (ddd, J=8.3, 4.8, 0.6 Hz, 1H), 2.92-2.61 (m, 2H), 2.32-2.05 (m, 1H), 1.38 (d, J=6.6 Hz, 3H); ESIMS m/z 300 ([M+2]).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe crude product was purified by silica gel chromatography
  3. washeluting with 0-5% MeOH/dichloromethane

Sources & evidence

ORD record
ord-6caad2164245453eb39d0ef1ad5828fa
Source dataset
uspto-grants-2016_08
Patent number
US09422278B2

Reaction notes

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