2-azidomethyl-5,6-dimethyl-1H-benzimidazole → HCID 178422306, compound

HRID 384162Notes

Reaction equation

HRID 384162 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[NH:19][C:18]2[CH:20]=[C:21]([CH3:25])[C:22]([CH3:24])=[CH:23][C:17]=2[N:16]=1)=[N+:12]=[N-:13]>>[ClH:1].[ClH:1].[CH3:24][C:22]1[C:21]([CH3:25])=[CH:20][C:18]2[NH:19][C:15]([CH2:14][N:11]3[CH:4]=[C:3]([CH2:2][C:5]4[N:6]=[C:7]([NH2:10])[NH:8][CH:9]=4)[N:13]=[N:12]3)=[N:16][C:17]=2[CH:23]=1

Participants

3

Reactant 2

HCID 579143202-azidomethyl-5,6-dimethyl-1H-benzimidazoleHCID 178439632HCID 178439632, compound

Product 1

HCID 178422306HCID 178422306, compoundYield 49.7%

Procedure

4-Prop-2-ynyl-1H-imidazol-2-ylamine hydrochloride (0.047 g, 0.295 mmol) was reacted with 2-azidomethyl-5,6-dimethyl-1H-benzimidazole (0.071 g, 0.354 mmol) following the general procedure for click reactions outlined above to produce 4-[1-(5,6 Dimethyl-1H-benzoimidazol-2-ylmethyl)-1H-[1,2,3]triazol-4-ylmethyl]-1H-imidazol-2-ylamine dihydrochloride (0.029 g, 25%) of a yellow solid. 1H NMR (300 MHz, CD3OD) δ 8.09 (s, 1H), δ 7.45 (s, 2H), δ 6.52 (s, 1H), δ 6.08 (s, 2H), δ 3.93 (s, 2H), δ 2.35 (s, 6H) ppm; 13C (75 MHz, CD3OD) δ 142.2, 136.9, 136.6, 124.5, 124.3, 113.8, 113.4, 110.0, 100.4, 85.8, 80.6, 75.3, 74.1, 45.0, 20.9, 19.28 ppm; HRMS (ESI) calcd for C16H18N8 (M+) 323.1727, found 323.1734.

Sources & evidence

ORD record
ord-7c6bb55e1ad546918fb88c4ae2a0f20c
Source dataset
uspto-grants-2013_02
Patent number
US08367713B2

Reaction notes

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