Benzyl azide → ethyl 2-(1-(cyclopropylmethyl)-1H-1,2,3-triazol-4-yl)-4-methylthiazole-5-carboxylate

HRID 2381808Notes

Reaction equation

[CH2:1]([N:8]=[N+:9]=[N-:10])[C:2]1[CH:7]=[CH:6]C=CC=1.N(CC1CC1)=[N+]=[N-].[C:18]([C:20]1[S:21][C:22]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:23]([CH3:25])[N:24]=1)#[CH:19]>>[CH:2]1([CH2:1][N:8]2[CH:19]=[C:18]([C:20]3[S:21][C:22]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:23]([CH3:25])[N:24]=3)[N:10]=[N:9]2)[CH2:7][CH2:6]1

Participants

Reactant 3

HCID 12152Benzyl azide

HCID 53235565(Azidomethyl)cyclopropane

HCID 59179676Ethyl 2-ethynyl-4-methylthiazole-5-carboxylate

Product 1

HCID 59179654ethyl 2-(1-(cyclopropylmethyl)-1H-1,2,3-triazol-4-yl)-4-methylthiazole-5-carboxylateYield 70%

Procedure

Following the procedure as described in Example 2, making variations as necessary to replace benzylazide with (azidomethyl)cyclopropane to react with ethyl 2-ethynyl-4-methylthiazole-5-carboxylate, the title compound was obtained as a white solid in 70% yield: 1H NMR (300 MHz, CDCl3) δ 8.21 (s, 1H), 4.39-4.19 (m, 4H), 2.69 (s, 3H), 1.38-1.19 (m, 4H), 0.74-0.64 (m, 2H), 0.48-0.37 (m, 2H); MS (ES+) m/z 293.3 (M+1).

Sources & evidence

ORD record: ord-01abe65f13734c8f8aebf8ad62525f2e
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258160B2

Reaction notes

Loading…