N-Boc-(R)-(+)-2-amino-1-butanol → (R)-4-(1-(2-aminobutyl)-1H-pyrazol-3-yl)-2-chloro-3-methylbenzonitrile
Reaction equation
[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([C:11]2[CH:15]=[CH:14][NH:13][N:12]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].O[CH2:17][C@H:18]([NH:21]C(=O)OC(C)(C)C)[CH2:19][CH3:20]>>[NH2:21][C@H:18]([CH2:19][CH3:20])[CH2:17][N:13]1[CH:14]=[CH:15][C:11]([C:8]2[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([Cl:1])[C:9]=2[CH3:10])=[N:12]1Participants
3
Procedure
(R)-4-(1-(2-aminobutyl)-1H-pyrazol-3-yl)-2-chloro-3-methylbenzonitrile was prepared using the method of Example 99 starting from 2-chloro-3-methyl-4-(1H-pyrazol-3-yl)benzonitrile (2.0 g, 9.19 mmol) and (R)-tert-butyl 1-hydroxybutan-2-ylcarbamate (3.48 g, 18.38 mmol). Yield 56.5%. m/z [288.8+1].
Sources & evidence
- ORD record
- ord-c2dca2f69c76493081a1c73790b756e2
- Source dataset
- uspto-grants-2015_03