3-(Azidomethyl)furan → HCID 178479119, compound

HRID 2283533Notes

Reaction equation

HRID 2283533 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][C:15]1[CH:19]=[CH:18][O:17][CH:16]=1)=[N+:12]=[N-:13]>>[ClH:1].[O:17]1[CH:18]=[CH:19][C: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:16]1

Participants

3

Reactant 2

HCID 230684473-(Azidomethyl)furanHCID 178439632HCID 178439632, compound

Product 1

HCID 178479119HCID 178479119, compoundYield 43%

Procedure

4-Prop-2-ynyl-1H-imidazol-2-ylamine hydrochloride (0.101 g, 0.639 mmol) was reacted with 3-azidomethyl-furan (0.094 g, 0.767 mmol) following the general procedure for click reactions outlined above to produce 4-(1-Furan-3-ylmethyl-1H-[1,2,3]triazol-4-ylmethyl)-1H-imidazol-2-ylamine hydrochloride (0.077 g, 43%) of a pale yellow solid. 1H NMR (300 MHz, CD3OD) δ 8.12 (s, 1H), δ 7.60 (s, 1H), δ 7.38 (s, 1H), δ 6.53 (s, 1H), δ 6.37 (s, 1H), δ 5.46 (s, 2H), δ 3.95 (s, 2H) ppm; 13C NMR (75 MHz, CD3OD) δ 146.1, 145.3, 144.1, 141.0, 123.3, 123.1, 110.3, 110.2, 109.9, 51.3, 19.9 ppm; HRMS (ESI) calcd for C11H12N6O (M+) 244.1145. Found 244.1145.

Sources & evidence

ORD record
ord-788478042d334926853daae3a529f060
Source dataset
uspto-grants-2015_09
Patent number
US09145395B2

Reaction notes

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