N-Boc-DL-valinol → 4-(1-(2-amino-3-methylbutyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile

HRID 872494Notes

Reaction equation

HRID 872494 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([C:10]2[CH:14]=[CH:13][NH:12][N:11]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].O[CH2:16][CH:17]([NH:21]C(=O)OC(C)(C)C)[CH:18]([CH3:20])[CH3:19]>>[NH2:21][CH:17]([CH:18]([CH3:20])[CH3:19])[CH2:16][N:12]1[CH:13]=[CH:14][C:10]([C:8]2[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([Cl:1])[CH:9]=2)=[N:11]1

Participants

3

Reactant 2

HCID 545981N-Boc-DL-valinolHCID 178509585HCID 178509585, compound

Product 1

HCID 671726234-(1-(2-amino-3-methylbutyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrileYield 22%

Procedure

The title compound was prepared using the method of Example 34(c) starting from 2-chloro-4-(1H-pyrazol-3-yl)benzonitrile (0.2 g; 0.98 mmol) and tert-butyl 1-hydroxy-3-methylbutan-2-ylcarbamate (0.22 g; m 1.09 mmol). Yield 22%. 1H-NMR (400 MHz; CDCl3): δ 1.02 (m, 6H), 1.71 (m, 1H), 3.14 (m, 1H), 3.95 (m, 1H), 4.27 (m, 1H), 6.61 (d, 1H), 7.51 (d, 1H), 7.66 (d, 1H), 7.77 (dd, 1H), 7.97 (s, 1H).

Sources & evidence

ORD record
ord-ec7415b229a944ef80350757041b3d74
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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