2-(Azidomethyl)furan → HCID 178479136, compound

HRID 529906Notes

Reaction equation

HRID 529906 reaction equation
[ClH:1].[CH2:2]([C:7]1[N:8]=[C:9]([NH2:12])[NH:10][CH:11]=1)[CH2:3][CH2:4][C:5]#[CH:6].[N:13]([CH2:16][C:17]1[O:18][CH:19]=[CH:20][CH:21]=1)=[N+:14]=[N-:15]>>[ClH:1].[O:18]1[CH:19]=[CH:20][CH:21]=[C:17]1[CH2:16][N:13]1[CH:6]=[C:5]([CH2:4][CH2:3][CH2:2][C:7]2[N:8]=[C:9]([NH2:12])[NH:10][CH:11]=2)[N:15]=[N:14]1

Participants

3

Reactant 2

HCID 233157982-(Azidomethyl)furanHCID 1784422514-Pent-4-ynyl-1H-imidazol-2-ylamine hydrochloride

Product 1

HCID 178479136HCID 178479136, compoundYield 50%

Procedure

4-Pent-4-ynyl-1H-imidazol-2-ylamine hydrochloride (0.093 g, 0.500 mmol) was reacted with 2-azidomethyl-furan (0.074 g, 0.601 mmol) following the general procedure for click reactions outlined above to produce 4-[3-(1-Furan-2-ylmethyl-1H-[1,2,3]triazol-4-yl)-propyl]-1Himidazol-2-ylamine hydrochloride (0.075, 50%) as a pale yellow solid. 1H NMR (300 MHz, DMSO) δ 7.85 (s, 1H), δ 7.65 (s, 1H), δ 6.70 (s, 2H), δ 6.64 (s, 1H), δ 6.52 (t, 1H), δ 6.46 (s, 1H), δ 5.58 (s, 2H), δ 2.61 (t, 2H), δ 2.41 (t, 2H), δ 1.82 (m, 2H) ppm; 13C NMR (75 MHz, DMSO) δ 163.6, 149.4, 147.9, 147.4, 144.3, 128.5, 122.6, 111.5, 110.3, 109.9, 46.3, 28.4, 24.9 ppm; HRMS (ESI) calcd for C13H16N6O (M+) 272.1458. found 272.1460.

Sources & evidence

ORD record
ord-78932496497945779aaf1cbed8814eb8
Source dataset
uspto-grants-2016_05
Patent number
US09351491B2

Reaction notes

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