2-Methylbenzaldehyde → [4-(5-Ethyl-3-pyridin-3-yl-pyrazol-1-yl)phenyl]-(2-methylbenzyl)amine

HRID 1634119Notes

Reaction equation

HRID 1634119 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH2:13][CH3:14])=[CH:11][C:10]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)=[N:9]2)=[CH:4][CH:3]=1.[C:21]1([CH3:29])[C:22]([CH:27]=O)=[CH:23][CH:24]=[CH:25][CH:26]=1.C([BH3-])#N.[Na+]>CC(O)=O.CO>[CH2:13]([C:12]1[N:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][CH2:29][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH3:27])=[CH:3][CH:4]=2)[N:9]=[C:10]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH:11]=1)[CH3:14]

Participants

5

Reactant 3

HCID 107222-MethylbenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 186770941-(4-Aminophenyl)-3-(3-pyridyl)-5-ethylpyrazole

Product 1

HCID 9842224[4-(5-Ethyl-3-pyridin-3-yl-pyrazol-1-yl)phenyl]-(2-methylbenzyl)amine

Reagents, catalysts & solvents 1

HCID 10129899Acetic acid methanolSolvent

Procedure

To a stirred solution of 1-(4-aminophenyl)-3-(3-pyridyl)-5-ethylpyrazole (300 mg, 1.14 mmol) and o-tolualdehyde (260 mg, 2.25 mmol) in 5% HOAc/MeOH (6 mL) at room temperature under argon, sodium cyanoborohydride (200 mg, 3.18 mmol) was added. The reaction mixture was stirred at room temperature for 4 h and then concentrated, diluted with water, extracted into ethyl acetate, washed with brine. The residue obtained on concentration was chromatographed on silica gel (eluant, gradient of 25-50% EtOAc in hexane) to provide the title compound as an oil that solidified on trituration with ether/petroleum ether (97 mg, 23%), m.p. 117-9° C. NMR (CDCl3, 400 MHz): 9.1 (s, 1H); 8.5 (br, 1H); 8.1 (br, 1H); 7.4-7.2 (overlapping m, 7H), 6.7 (d,2H), 6.5 (s, 1H), 4.4 (s, 2H), 4.1 (br, 1H), 2.7 (q, 2H), 2.4 (s, 3H), 1.3 (t, 3H).

Workup

  1. concentrationconcentrated
  2. additiondiluted with water
  3. extractionextracted into ethyl acetate
  4. washwashed with brine
  5. customThe residue obtained on concentration
  6. customwas chromatographed on silica gel (eluant, gradient of 25-50% EtOAc in hexane)

Sources & evidence

ORD record
ord-2945e84d3ecf4c8f852312f62af01a87
Source dataset
uspto-grants-2003_01
Patent number
US06506747B1

Reaction notes

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