tert-Butyl N-(2-((methylsulfonyl)oxy)ethyl)carbamate → 5-(1-(2-aminoethyl)-1H-pyrazol-3-yl)-2-nitrobenzonitrile

HRID 872485Notes

Reaction equation

HRID 872485 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:9]([C:12]2[NH:16][N:15]=[CH:14][CH:13]=2)=[CH:8][C:5]=1[C:6]#[N:7])([O-:3])=[O:2].CS(O[CH2:22][CH2:23][NH:24]C(OC(C)(C)C)=O)(=O)=O>>[NH2:24][CH2:23][CH2:22][N:15]1[CH:14]=[CH:13][C:12]([C:9]2[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[C:5]([CH:8]=2)[C:6]#[N:7])=[N:16]1

Participants

3

Reactant 2

HCID 22605302tert-Butyl N-(2-((methylsulfonyl)oxy)ethyl)carbamateHCID 671711062-nitro-5-(1H-pyrazol-5-yl)benzonitrile

Product 1

HCID 671716215-(1-(2-aminoethyl)-1H-pyrazol-3-yl)-2-nitrobenzonitrile

Procedure

The title compound was prepared from 2-nitro-5-(1H-pyrazol-5-yl)benzonitrile (1.00 g) and 2-(tert-butoxycarbonylamino)ethyl methanesulfonate (1.45 g) using the method of Example 37(c). Yield 0.32 g (as HCl-salt). 1H-NMR (400 MHz; d6-DMSO): δ 3.34 (t, 2H), 4.50 (t, 2H), 7.15 (d, 1H), 7.99 (d, 1H), 8.21 (br s, 2H), 8.39 (dd, 1H), 8.45 (d, 1H), 8.61 (d, 1H).

Sources & evidence

ORD record
ord-24191a8299d34356a056db4791455fd9
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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