N-Boc-(R)-1-amino-2-propanol → (R)-4-(1-(1-aminopropan-2-yl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile

HRID 872800Notes

Reaction equation

HRID 872800 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[C@H:16]([CH3:26])[CH2:17][NH:18]C(=O)OC(C)(C)C>>[NH2:18][CH2:17][C@H: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)[CH3:26]

Participants

3

Reactant 2

HCID 12094522N-Boc-(R)-1-amino-2-propanolHCID 178509585HCID 178509585, compound

Product 1

HCID 67172099(R)-4-(1-(1-aminopropan-2-yl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile

Procedure

(R)-4-[1-(1-Aminopropan-2-yl)-1H-pyrazol-3-yl]-2-chlorobenzonitrile was prepared using the method of Example 34(c) starting from 2-chloro-4-(1H-pyrazol-3-yl)benzonitrile and (R)-tert-butyl 2-hydroxypropylcarbamate. 1H NMR (400 MHz, CDCl3): 1.24 (21-1, broad s), 1.54 (3H, d), 3.05 (1H, distorted dd), 3.17 (1H, distorted dd), 4.34 (1H, m), 6.61 (1H, d), 7.52 (1H, d), 7.66 (1H, d), 7.78 (1H, dd), 7.98 (1H, d).

Sources & evidence

ORD record
ord-534dce452b334fc7bb28a7221e85634b
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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