3-(2-Azidoethyl)thiophene → HCID 178479121, compound

HRID 384161Notes

Reaction equation

HRID 384161 reaction equation
[ClH:1].[CH2:2]([C:5]1[N:6]=[C:7]([NH2:10])[NH:8][CH:9]=1)[C:3]#[CH:4].[N:11]([CH2:14][CH2:15][C:16]1[CH:20]=[CH:19][S:18][CH:17]=1)=[N+:12]=[N-:13]>>[ClH:1].[S:18]1[CH:19]=[CH:20][C:16]([CH2:15][CH2:14][N:11]2[CH:4]=[C:3]([CH2:2][C:5]3[N:6]=[C:7]([NH2:10])[NH:8][CH:9]=3)[N:13]=[N:12]2)=[CH:17]1

Participants

3

Reactant 2

HCID 219249973-(2-Azidoethyl)thiopheneHCID 178439632HCID 178439632, compound

Product 1

HCID 178479121HCID 178479121, compoundYield 60%

Procedure

4-Prop-2-ynyl-1H-imidazol-2-ylamine hydrochloride (0.101 g, 0.641 mmol was reacted with 3-(2-Azido-ethyl)-thiophene (0.118 g, 0.769 mmol) following the general procedure for click reactions outlined above to produce 4-[1-(2-Thiophen-3-yl-ethyl)-1H [1,2,3]triazol-4-ylmethyl]-1H-imidazol-2-ylamine hydrochloride (0.119 g, 60%) of a pale yellow solid. 1H NMR (300 MHz, CD3OD) δ 7.42 (s, 1H), δ 7.19 (t, 1H), δ 6.90 (s, 1H), □ 6.78 (d, 1H), δ 6.09 (s, 1H), δ 4.47 (t, 2H), δ 3.67 (s, 2H), δ 3.09 (t, 2H) ppm; 13C; (75 MHz, CD3OD) δ 151.2, 145.7, 137.7, 130.5, 127.8, 125.8, 122.9, 121.9, 110.3, 50.798, 30.7, 23.3 ppm; HRMS (ESI) calcd for C12H14N6S (M+) 274.1001, found 274.1007.

Sources & evidence

ORD record
ord-d04ead8f5eb34714bdb6584c69d3e4c2
Source dataset
uspto-grants-2013_02
Patent number
US08367713B2

Reaction notes

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