2-(azidomethyl)-1H-benzo[d]imidazole → HCID 178478670, compound

HRID 2283546Notes

Reaction equation

HRID 2283546 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][C:16]1[NH:20][C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[N:17]=1)=[N+:13]=[N-:14]>>[ClH:1].[ClH:1].[NH:17]1[C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=[C:16]1[CH2:15][N:12]1[CH:5]=[C:4]([CH2:3][CH2:2][C:6]2[N:7]=[C:8]([NH2:11])[NH:9][CH:10]=2)[N:14]=[N:13]1

Participants

3

Reactant 2

HCID 155637102-(azidomethyl)-1H-benzo[d]imidazoleHCID 178441359HCID 178441359, compound

Product 1

HCID 178478670HCID 178478670, compoundYield 95.9%

Procedure

4-But-3-ynyl-1H-imidazol-2-ylamine hydrochloride (0.061 g, 0.361 mmol) was reacted with 2-azidomethyl-1-H-benzimidazole (0.075 g, 0.433 mmol) following the general procedure for click reactions outlined above to produce 4-{2-[1-(1H-Benzoimidazol-2-ylmethyl)-1H-[1,2,3]triazol-4-yl]-ethyl}-1H-imidazol-2-ylamine dihydrochloride (0.066 g, 48%) of a yellow solid. 1H NMR (300 MHz, CD3OD) δ 8.05 (s, 1H), δ 7.68 (m, 2H), δ 7.48 (m, 2H), δ 6.38 (s, 1H), δ 6.15 (s, 2H), δ 2.90 (t, 2H), δ 2.76 (t, 2H) ppm; 13C (75 MHz, CD3OD) δ 147.4, 146.9, 146.8, 131.3, 127.0, 126.4, 124.1, 114.1, 109.2, 44.7, 24.0, 23.9 ppm; HRMS (ESI) calcd for C15H17N8 (M+) 309.1570. Found 309.1572.

Sources & evidence

ORD record
ord-21085f216d194d7f9a59135093bded29
Source dataset
uspto-grants-2015_09
Patent number
US09145395B2

Reaction notes

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