3-(2-Azidoethyl)thiophene → HCID 178479126, compound

HRID 529897Notes

Reaction equation

HRID 529897 reaction equation
[ClH:1].[CH2:2]([C:6]1[N:7]=[C:8]([NH2:11])[NH:9][CH:10]=1)[CH2:3][C:4]#[CH:5].[N:12]([CH2:15][CH2:16][C:17]1[CH:21]=[CH:20][S:19][CH:18]=1)=[N+:13]=[N-:14]>>[ClH:1].[S:19]1[CH:20]=[CH:21][C:17]([CH2:16][CH2:15][N:12]2[CH:5]=[C:4]([CH2:3][CH2:2][C:6]3[N:7]=[C:8]([NH2:11])[NH:9][CH:10]=3)[N:14]=[N:13]2)=[CH:18]1

Participants

3

Reactant 2

HCID 219249973-(2-Azidoethyl)thiopheneHCID 178441359HCID 178441359, compound

Product 1

HCID 178479126HCID 178479126, compoundYield 47.2%

Procedure

4-But-3-ynyl-1H-imidazol-2-ylamine hydrochloride (0.078 g, 0.45 mmol) was reacted with 3-(2-Azido-ethyl)-thiophene (0.083 g, 0.543 mmol) following the general procedure for click reactions outlined above to produce 4-{2-[1-(2-Thiophen-3-yl-ethyl)-1H-[1,2,3]triazol-4-yl]-ethyl}-1H-imidazol-2-ylamine hydrochloride (0.069 g, 47%) of a pale yellow oil. 1H NMR (300 MHz, CD3OD) δ 7.33 (s, 1H), δ 7.19 (dd, 1H), δ 6.85 (d, 1H), δ 6.72 (d, 1H), δ 6.06 (s, 1H), δ 4.45 (t, 2H), δ 3.08 (t, 2H), δ 2.79 (t, 2H), δ 2.59 (t, 2H), ppm 13C (75 MHz, CD3OD) δ 149.3, 147.0, 137.7, 132.1, 127.7, 125.8, 122.4, 121.9, 110.6, 50.8, 30.7, 26.6, 24.8 ppm; HRMS (ESI) calcd for C13H17N6S (M+) 289.1229. found 289.1231.

Sources & evidence

ORD record
ord-71a307e3932f47d9a4662b8d2d288c54
Source dataset
uspto-grants-2016_05
Patent number
US09351491B2

Reaction notes

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