N-Boc-(R)-(+)-2-amino-1-butanol → (R)-4-(1-(2-aminobutyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile hydrochloride

HRID 872512Notes

Reaction equation

HRID 872512 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([C:10]2[NH:14][N:13]=[CH:12][CH:11]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].O[CH2:16][C@H:17]([NH:20]C(=O)OC(C)(C)C)[CH2:18][CH3:19]>>[ClH:1].[NH2:20][C@H:17]([CH2:18][CH3:19])[CH2:16][N:13]1[CH:12]=[CH:11][C:10]([C:8]2[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([Cl:1])[CH:9]=2)=[N:14]1

Participants

3

Reactant 2

HCID 11435422N-Boc-(R)-(+)-2-amino-1-butanolHCID 671701022-chloro-4-(1H-pyrazol-3-yl)benzonitrile

Product 1

HCID 70656035(R)-4-(1-(2-aminobutyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile hydrochlorideYield 54.2%

Procedure

The Mitsunobu reaction was conducted as described in Example 3(c) using 2-chloro-4-(1H-pyrazol-5-yl)benzonitrile (0.60 g, 2.95 mmol) and (R)-tert-butyl 1-hydroxybutan-2-ylcarbamate (0.61 g, 3.24 mmol) as starting materials. 0.249 g (31%) of the title compound was obtained after workup. 1H-NMR (400 MHz; d6-DMSO): δ 0.91 (t, 3H), 1.22 (d, 3H), 3.33 (broad s, NH2HCl overlapping with water) 3.99 (dd, 1H), 4.12 (dd, 1H), 4.44-4.86 (m, 1H), 6.97 (d, 1H), 7.86 (d, 1H), 7.92-7.99 (m, 2H), 8.11 (d, 1H).

Workup

  1. customThe Mitsunobu reaction

Sources & evidence

ORD record
ord-128a2e508b5a4b93a742f7254a6400c0
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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