Sodium Hydroxide → N-{1-[(2-methyl-1,3-thiazol-4-yl)methyl]-1H-pyrazol-3-yl}acetamide

HRID 522612Notes

Reaction equation

HRID 522612 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]C=1.Cl.ClCC1N=C(C)[S:24]C=1.[OH-].[Na+]>>[CH3:6][C:5]1[S:24][CH:2]=[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]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 27342034-(Chloromethyl)-2-methyl-1,3-thiazole--hydrogen chloride (1/1)2×HCID 86691609N-{1-[(3-hydroxy-2-pyridinyl)methyl]-1H-pyrazol-3-yl}acetamide

Product 1

HCID 86691611N-{1-[(2-methyl-1,3-thiazol-4-yl)methyl]-1H-pyrazol-3-yl}acetamide

Procedure

Title compound was prepared by a method analogous to that described for Intermediate 41, replacing the benzyl halide by 4-(chloromethyl)-2-methyl-1,3-thiazole hydrochloride (MAYBRIDGE). 4-(chloromethyl)-2-methyl-1,3-thiazole hydrochloride (MAYBRIDGE) was also liberated using NaOH (1N, aq) at room temperature. 1H NMR (300 MHz, DMSO-d6) ppm: 10.37 (s, 1H), 7.62-7.63 (m, 1H), 7.25 (s, 1H), 6.43-6.44 (m, 1H), 5.20 (s, 2H), 2.59 (s, 3H), 1.93 (s, 3H). [ES+MS] m/z 237 (MH+).

Workup

  1. customat room temperature

Sources & evidence

ORD record
ord-7a6fe0297cff402386d9315c088a271c
Source dataset
uspto-grants-2016_05
Patent number
US09334265B2

Reaction notes

Loading…