2-(Chloromethyl)quinoline hydrochloride → N-[1-(2-quinolinylmethyl)-1H-pyrazol-3-yl]acetamide

HRID 522611Notes

Reaction equation

HRID 522611 reaction equation
O[C:2]1[C:3]([CH2:8][N:9]2[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:17])[CH3:16])=[N:10]2)=[N:4][CH:5]=[CH:6][CH:7]=1.Cl.Cl[CH2:20][C:21]1[CH:30]=[CH:29]C2C(=CC=CC=2)N=1>>[N:4]1[C:5]2[C:6](=[CH:20][CH:21]=[CH:30][CH:29]=2)[CH:7]=[CH:2][C:3]=1[CH2:8][N:9]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:17])[CH3:16])=[N:10]1

Participants

3

Reactant 2

HCID 30838232-(Chloromethyl)quinoline hydrochlorideHCID 86691609N-{1-[(3-hydroxy-2-pyridinyl)methyl]-1H-pyrazol-3-yl}acetamide

Product 1

HCID 86691610N-[1-(2-quinolinylmethyl)-1H-pyrazol-3-yl]acetamide

Procedure

Title compound was prepared by a method analogous to that described for Intermediate 41 using Intermediate 1 (150 mg, 1.199 mmol), replacing 2-(Bromomethyl)-3-pyridinol hydrobromide with 2-(chloromethyl)quinoline hydrochloride (ALDRICH). Title compound was obtained (90 mg, 0.338 mmol, 28.2% yield). 1H NMR (300 MHz, CDCl3) δ ppm: 8.10 (d, 1H), 8.07 (d, 1H), 7.79 (d, 1H), 7.74 (m, 1H), 7.55 (m, 1H), 7.46 (d, 1H), 7.07 (d, 1H), 6.76 (d, 1H), 5.49 (s, 2H), br s 2.14 (s, 3H). [ES+MS] m/z 267 (MH+).

Workup

  1. customTitle compound was prepared by a method analogous to

Sources & evidence

ORD record
ord-6435b94a1eff4a5d87a754b0d41e0a3a
Source dataset
uspto-grants-2016_05
Patent number
US09334265B2

Reaction notes

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