Triethylamine → 5-Nitro-1H-pyrazole 3-cyclopropylmethylcarboxamide

HRID 1630408Notes

Reaction equation

HRID 1630408 reaction equation
[N+:1]([C:4]1[NH:8][N:7]=[C:6](C(O)=O)[CH:5]=1)([O-:3])=[O:2].C[N:13]([C:15]([O:19]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.Cl.N[CH2:45][CH:46]1[CH2:48][CH2:47]1>CN(C=O)C>[N+:1]([C:4]1[NH:8][N:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:46]1[CH:48]([CH2:47][C:15]([NH2:13])=[O:19])[CH2:45]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 81671(Cyclopropylmethyl)ammonium chlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 862226845-Nitro-1H-pyrazole-3-carboxylic acid

Product 1

HCID 1317316995-Nitro-1H-pyrazole 3-cyclopropylmethylcarboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7.5 g of 5-nitro-1H-pyrazole-3-carboxylic acid were dissolved in 70 ml of DMF. 19.9 g of HATU and 9.6 g of triethylamine are added at RT and, after stirring for 10 minutes, 5.1 g of aminomethylcyclopropane hydrochloride are added, and the mixture is stirred at RT overnight. After aqueous workup, the crude product is purified by column chromatography (silica gel, methanol:DCM=1:30).

Workup

  1. stirringthe mixture is stirred at RT overnight
  2. customAfter aqueous workup, the crude product is purified by column chromatography (silica gel, methanol:DCM=1:30)

Sources & evidence

ORD record
ord-14de56f77c564579bc2accc5f05d4b58
Source dataset
uspto-grants-2014_07
Patent number
US08791133B2

Reaction notes

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