tert-butyl N-((2R)-1-hydroxypropan-2-yl)carbamate → (R)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile

HRID 872508Notes

Reaction equation

HRID 872508 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:19]C(=O)OC(C)(C)C)[CH3:18]>>[NH2:19][C@H:17]([CH3:18])[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 13200309tert-butyl N-((2R)-1-hydroxypropan-2-yl)carbamateHCID 671701022-chloro-4-(1H-pyrazol-3-yl)benzonitrile

Product 1

HCID 67171309(R)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrileYield 17%

Procedure

The title compound was prepared with the Mitsunobu reaction using the method of Example 3(c) starting from 2-chloro-4-(1H-pyrazol-5-yl)-benzonitrile (2.00 g, 9.82 mmol) and (R)-tert-butyl 1-hydroxypropan-2-ylcarbamate (1.893 g, 10.80 mmol). After Boc removal and workups 0.434 g (17%) of the title compound was obtained. 1H-NMR (400 MHz; d6-DMSO): δ 0.97 (d, 3H), 2.96 (m, 2H), 4.15 (m, 2H), 6.98 (d, 1H), 7.86 (d, 1H), 7.92-8.00 (m, 2H), 8.11 (d, 1H).

Workup

  1. customThe title compound was prepared with the Mitsunobu reaction
  2. customAfter Boc removal

Sources & evidence

ORD record
ord-5679c4ad3314433b89efd09170f77a85
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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