Triethylamine → 5-amino-1-methyl-N-[2-(tritylamino)ethyl]-1H-pyrazole-4-carboxamide

HRID 459650

Reaction equation

HRID 459650 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[C:8]([OH:10])=O.[NH2:11][CH2:12][CH2:13][NH:14][C:15]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC>C(Cl)(Cl)Cl>[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[C:8]([NH:11][CH2:12][CH2:13][NH:14][C:15]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:10]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 3133425-amino-1-methyl-1H-pyrazole-4-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2794294N-tritylethylenediamine

Product 1

HCID 184423955-amino-1-methyl-N-[2-(tritylamino)ethyl]-1H-pyrazole-4-carboxamideYield 53.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 5-amino-1-methyl-1H-pyrazole-4-carboxylic acid (7.1 g), N-(2-aminoethyl)tritylamine (15.1 g) and triethylamine (10.1 g) in chloroform (200 ml) was added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (9.6 g), and the mixture was stirred at room temperature for 16 hours. The reaction mixture was washed successively with 10% aqueous citric acid solution, brine and saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was triturated with ethyl acetate and dried in vacuo to give 5-amino-1-methyl-N-[2-(tritylamino)ethyl]-1H-pyrazole-4-carboxamide (11.4 g) as a solid.

Workup

  1. washThe reaction mixture was washed successively with 10% aqueous citric acid solution, brine and saturated aqueous sodium hydrogencarbonate solution
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with ethyl acetate
  6. customdried in vacuo

Sources & evidence

ORD record
ord-812a5b8ee45345569b5df881917c8b58
Source dataset
uspto-grants-2007_03
Patent number
US07192943B2

Linked notes

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