Triethylamine → HCID 78076410, compound

HRID 2363216Notes

Reaction equation

HRID 2363216 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]([OH:15])=O)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:16][CH2:17][C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=1.C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C.Cl.[NH2:40][OH:41]>ClCCl.C(O)C>[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]([NH:23][CH2:22][C:21]2[CH:24]=[CH:25][C:18]([C:17](=[N:40][OH:41])[NH2:16])=[CH:19][CH:20]=2)=[O:15])[CH:10]=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 826084-(Aminomethyl)benzonitrileHCID 443297Hydroxyamine hydrochlorideHCID 64838761-Benzyl-1H-pyrazole-4-carboxylic acid

Product 1

HCID 78076410HCID 78076410, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

20.8 g of 1-benzylpyrazole-4-carboxylic acid was reacted with 1 equivalent of 4-(aminomethyl)benzonitrile, in the presence of 1.1 equivalents of oxalyl chloride, 3 equivalents of triethylamine in dichloromethane at room temperature for 3 h. The product was then reacted with hydroxylamine hydrochloride (3 equivalents) in ethanol at 80° C. for 3 h. The target compound (17.5 g) was obtained as a off-white powder following solvent removal by evaporation. Purity assessed by HPLC was 98.7%, and mass was verified by LC/MS/MS (predicted m+1=350.2, obtained m+1=350.2). 1H-NMR (DMSO): δ 4.39-4.40 (2H), 5.34 (2H), 5.76 (2H), 7.25-7.30 (4H), 7.34-7.36 (3H), 7.59-7.62 (2H), 7.91 (1H), 8.27 (1H), 8.63 (1H), 9.57 (1H).

Sources & evidence

ORD record
ord-699f605422a94c74bfdbe8d1a5e90a76
Source dataset
uspto-grants-2014_04
Patent number
US08691861B2

Reaction notes

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