tert-Butyl 2-(3-(4-cyano-3-nitrophenyl)-1H-pyrazol-1-yl)ethylcarbamate → 4-(1-(2-aminoethyl)-1H-pyrazol-3-yl)-2-nitrobenzonitrile

HRID 872500Notes

Reaction equation

HRID 872500 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:13]=[CH:12][N:11]([CH2:14][CH2:15][NH:16]C(=O)OC(C)(C)C)[N:10]=2)=[CH:5][C:4]=1[N+:24]([O-:26])=[O:25])#[N:2]>C(Cl)Cl>[NH2:16][CH2:15][CH2:14][N:11]1[CH:12]=[CH:13][C:9]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[C:4]([N+:24]([O-:26])=[O:25])[CH:5]=2)=[N:10]1

Participants

3

Reactant 1

HCID 67172190tert-Butyl 2-(3-(4-cyano-3-nitrophenyl)-1H-pyrazol-1-yl)ethylcarbamate

Product 1

HCID 671725774-(1-(2-aminoethyl)-1H-pyrazol-3-yl)-2-nitrobenzonitrileYield 105.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(3-(4-cyano-3-nitrophenyl)-1H-pyrazol-1-yl)-ethylcarbamate (0.92 g) in DCM (3 ml) 17% HCl-ethanol solution (10 ml) was added and the mixture was stirred at RT until disappearance of the starting material. The precipitate was filtrated, washed with diethylether and dried to give 0.70 g of the product as HCl-salt. 1H-NMR (400 MHz; d6-DMSO): δ 3.31 (m, 2H), 4.50 (t, 7.12 (d, 1H), 7.99 (d, 1H), 8.19 (d, 1H), 8.27-8.35 (m, 3H), 8.37 (dd, 1H), 8.73 (d, 1H).

Workup

  1. filtrationThe precipitate was filtrated
  2. washwashed with diethylether
  3. customdried

Sources & evidence

ORD record
ord-d297d3fe9aac46edac3356dc063f1dfd
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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