(3-Azido-2-methylpropenyl)-benzene → HCID 178438933, compound

HRID 384183Notes

Reaction equation

HRID 384183 reaction equation
[ClH:1].[CH2:2]([C:9]1[N:10]=[C:11]([NH2:14])[NH:12][CH:13]=1)[CH2:3][CH2:4][CH2:5][CH2:6][C:7]#[CH:8].[N:15]([CH2:18][C:19]([CH3:27])=[CH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[N+:16]=[N-:17]>>[ClH:1].[CH3:27][C:19](=[CH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:18][N:15]1[CH:8]=[C:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:9]2[N:10]=[C:11]([NH2:14])[NH:12][CH:13]=2)[N:17]=[N:16]1

Participants

3

Reactant 2

HCID 76639733(3-Azido-2-methylpropenyl)-benzeneHCID 178442541HCID 178442541, compound

Product 1

HCID 178438933HCID 178438933, compoundYield 65%

Procedure

4-Hept-6-ynyl-1H-imidazol-2-ylamine hydrochloride (0.060 g, 0.281 mmol) was reacted with (3-Azido-2-methyl-propenyl)-benzene (0.058 g, 0.336 mmol) following the general procedure for click reactions outlined above to produce 4-{5-[1-(2-Methyl-3-phenyl-allyl)-1H-[1,2,3]triazol-4-yl]-pentyl}-1H-imidazol-2-ylamine hydrochloride (0.064 g, 65%) as a pale yellow solid. 1H NMR (300 MHz, CD3OD) δ 8.23 (s, 1H), δ 6.93-6.83 (m, 5H), δ 6.38 (s, 1H), δ 6.08 (s, 1H), δ 4.93 (s, 2H), δ 2.51 (t, 2H), δ 2.09 (t, 2H), δ 1.43 (s, 3H), δ 1.41 (m, 2H), δ 1.25 (m, 2H), δ 1.05 (m, 2H) ppm; 13C (75 MHz, CD3OD) δ 147.7, 144.8, 136.3, 132.8, 129.8, 128.9, 128.6, 128.5, 128.2, 127.6, 127.5, 127.0, 108.5, 61.3, 28.0, 27.6, 27.5, 24.0, 22.9, 14.7 ppm; HRMS (ESI) calcd for C20H27N6 (M+) 351.2291, found 351.2291.

Sources & evidence

ORD record
ord-3b024b6dc0024e52890eb5bbd40794c9
Source dataset
uspto-grants-2013_02
Patent number
US08367713B2

Reaction notes

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