2-azidomethyl-5,6-dimethyl-1H-benzimidazole → HCID 178422307, compound

HRID 529903Notes

Reaction equation

HRID 529903 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]=[C:22]([CH3:26])[C:23]([CH3:25])=[CH:24][C:18]=2[N:17]=1)=[N+:13]=[N-:14]>>[ClH:1].[ClH:1].[CH3:25][C:23]1[C:22]([CH3:26])=[CH:21][C:19]2[NH:20][C:16]([CH2:15][N:12]3[CH:5]=[C:4]([CH2:3][CH2:2][C:6]4[N:7]=[C:8]([NH2:11])[NH:9][CH:10]=4)[N:14]=[N:13]3)=[N:17][C:18]=2[CH:24]=1

Participants

3

Reactant 2

HCID 579143202-azidomethyl-5,6-dimethyl-1H-benzimidazoleHCID 178441359HCID 178441359, compound

Product 1

HCID 178422307HCID 178422307, compoundYield 117.6%

Procedure

4-But-3-ynyl-1H-imidazol-2-ylamine hydrochloride (0.0734 g, 0.432 mmol) was reacted with 2-azidomethyl-5,6-dimethyl-1H-benzimidazole (0.104 g, 0.518 mmol) following the general procedure for click reactions outlined above to produce 4-{2-[1-(5,6-Dimethyl-1Hbenzoimidazol-2-ylmethyl)-1H-[1,2,3]triazol-4-yl]-ethyl}-1H-imidazol-2-ylamine dihydrochloride (0.104 g, 59%) of a pale yellow solid. 1H NMR (300 MHz, CD3OD) δ 7.70 (s, 1H), δ 7.19 (s, 2H), δ 6.23 (s, 1H), δ 5.66 (s, 2H), δ 2.85 (t, 2H), δ 2.68 (t, 2H), □ 2.21 (s, 6H) ppm; 13C (75 MHz, CD3OD) δ 148.2, 147.0, 146.9, 132.3, 128.9, 122.8, 120.0, 115.1, 109.7, 100.4, 25.1, 24.4, 19.2 ppm; HRMS (ESI) calcd for C17H20N8 (M+) 337.1883. found 337.1886.

Sources & evidence

ORD record
ord-b11b2b568fe34407a36e769cbe85b986
Source dataset
uspto-grants-2016_05
Patent number
US09351491B2

Reaction notes

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