1,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamate → (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-nitrobenzonitrile

HRID 872648Notes

Reaction equation

HRID 872648 reaction equation
[N+:1]([C:4]1[CH:11]=[C:10]([C:12]2[NH:16][N:15]=[CH:14][CH:13]=2)[CH:9]=[CH:8][C:5]=1[C:6]#[N:7])([O-:3])=[O:2].O[CH2:18][C@@H:19]([NH:21]C(=O)OC(C)(C)C)[CH3:20]>>[NH2:21][C@@H:19]([CH3:20])[CH2:18][N:15]1[CH:14]=[CH:13][C:12]([C:10]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([N+:1]([O-:3])=[O:2])[CH:11]=2)=[N:16]1

Participants

3

Reactant 2

HCID 70231031,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamateHCID 671687892-nitro-4-(1H-pyrazol-5-yl)benzonitrile

Product 1

HCID 70656286(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-nitrobenzonitrileYield 71%

Procedure

(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-nitrobenzonitrile was prepared using the method of Example 34(c) starting from 2-nitro-4-(1H-pyrazol-5-yl)benzonitrile (2.0 g, 9.34 mmol) and (S)-tert-butyl 1-hydroxypropan-2-ylcarbamate (1.6 g, 9.13 mmol). Yield 71.0%. H-NMR (400 MHz; DMSO-d6): 0.98 (d, 3H), 3.23-3.33 (m, 1H), 4.01-4.12 (m, 2H), 7.08 (d, 1H), 7.90 (d, 1H), 8.19 (d, 1H), 8.34 (dd, 1H), 8.69 (d, HA).

Sources & evidence

ORD record
ord-b1e7dc91b9c84bf4ad37cab39fab4fcb
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

Loading…